GB1494877A - Heterocyclic compounds and plant growth regulating compositions - Google Patents
Heterocyclic compounds and plant growth regulating compositionsInfo
- Publication number
- GB1494877A GB1494877A GB515/76A GB51576A GB1494877A GB 1494877 A GB1494877 A GB 1494877A GB 515/76 A GB515/76 A GB 515/76A GB 51576 A GB51576 A GB 51576A GB 1494877 A GB1494877 A GB 1494877A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compounds
- compound
- cor
- prepared
- 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
- 230000008635 plant growth Effects 0.000 title abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 230000001105 regulatory effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 13
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 abstract 2
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- -1 Diphenyl heterocyclic compounds Chemical class 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000031709 bromination Effects 0.000 abstract 2
- 238000005893 bromination reaction Methods 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical group C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 abstract 1
- ZUXBPGMQEGEWHI-UHFFFAOYSA-N 2-(2-bromoacetyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)CBr ZUXBPGMQEGEWHI-UHFFFAOYSA-N 0.000 abstract 1
- QDAWXRKTSATEOP-UHFFFAOYSA-N 2-acetylbenzoic acid Chemical compound CC(=O)C1=CC=CC=C1C(O)=O QDAWXRKTSATEOP-UHFFFAOYSA-N 0.000 abstract 1
- LUPHUKWXQVNVCX-UHFFFAOYSA-N 5-(2-methylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NN1 LUPHUKWXQVNVCX-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910001413 alkali metal ion Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000005594 diketone group Chemical group 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000008520 organization Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPC023575 | 1975-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1494877A true GB1494877A (en) | 1977-12-14 |
Family
ID=3766094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB515/76A Expired GB1494877A (en) | 1975-01-10 | 1976-01-07 | Heterocyclic compounds and plant growth regulating compositions |
Country Status (13)
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197405A (en) * | 1979-02-22 | 1980-04-08 | Monsanto Company | Thermolysis of 3'-(Aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one |
| US4208510A (en) * | 1978-12-20 | 1980-06-17 | Monsanto Company | Preparation of 3-aryl-isoxazol-5-yl benzoates |
| US4209629A (en) * | 1978-12-20 | 1980-06-24 | Monsanto Company | 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones |
| US4210762A (en) * | 1978-08-17 | 1980-07-01 | Monsanto Company | 2[5-(3-Trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl] benzoates |
| US4223154A (en) * | 1979-03-09 | 1980-09-16 | Monsanto Company | Preparation of 2-(3-aryl-5-isoxazol) benzoyl halide |
| US4230866A (en) * | 1979-05-17 | 1980-10-28 | Monsanto Company | Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof |
| US4268299A (en) * | 1978-08-17 | 1981-05-19 | Monsanto Company | Method and composition for plant growth regulation containing trifluoromethyl 1,3,4 oxadiazol benzoates |
| US4401457A (en) | 1980-06-18 | 1983-08-30 | Monsanto Company | 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as herbicides |
| JP2008515985A (ja) * | 2004-10-13 | 2008-05-15 | ピーティーシー セラピューティクス，インコーポレーテッド | ナンセンス抑制の化合物とその使用方法 |
| JP2011525534A (ja) * | 2008-06-24 | 2011-09-22 | アイアールエム・リミテッド・ライアビリティ・カンパニー | Ｇタンパク質共役受容体を調節するための化合物および方法 |
| CN114773330A (zh) * | 2022-05-24 | 2022-07-22 | 贵州医科大学 | 丁苯酞-噁/噻二唑类化合物及其制备方法和应用 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1579352A (en) * | 1977-05-06 | 1980-11-19 | Lepetit Spa | 3,5-disubstituted-1h-1,2,4-triazoles |
| US4135910A (en) | 1977-05-12 | 1979-01-23 | Monsanto Company | Oxadiazol-3-yl-benzoates as plant growth regulants |
| US4140515A (en) | 1977-05-12 | 1979-02-20 | Monsanto Company | Aryl-3-isoxazole benzoates as plant growth regulants and herbicides |
| US4229204A (en) * | 1978-12-04 | 1980-10-21 | Monsanto Company | Trifluoromethylphenyl isoxazolyl benzoates |
| DE3623302A1 (de) * | 1985-11-09 | 1987-05-14 | Bayer Ag | Nicotinsaeurederivate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1024971B (de) * | 1956-11-05 | 1958-02-27 | Bayer Ag | Verfahren zur Herstellung von 2,5-Diaryl-1,3,4-oxdiazolen |
| FR1368390A (fr) * | 1963-07-25 | 1964-07-31 | Basf Ag | Procédé pour la production de chlorures d'acides carboxyliques hétérocycliques et d'acides carboxyliques hétérocycliques |
-
1975
- 1975-01-10 AU AU10078/76A patent/AU497898B2/en not_active Expired
-
1976
- 1976-01-05 ZA ZA00760038A patent/ZA7638B/xx unknown
- 1976-01-06 NZ NZ179684A patent/NZ179684A/xx unknown
- 1976-01-07 IL IL48803A patent/IL48803A0/xx unknown
- 1976-01-07 GB GB515/76A patent/GB1494877A/en not_active Expired
- 1976-01-08 NL NL7600152A patent/NL7600152A/xx not_active Application Discontinuation
- 1976-01-09 IT IT19140/76A patent/IT1054759B/it active
- 1976-01-09 BE BE163425A patent/BE837454A/xx unknown
- 1976-01-09 FR FR7600526A patent/FR2332705A1/fr not_active Withdrawn
- 1976-01-09 DE DE19762600655 patent/DE2600655A1/de not_active Withdrawn
- 1976-01-12 CH CH29376A patent/CH603044A5/xx not_active IP Right Cessation
- 1976-01-12 CA CA243,584A patent/CA1066708A/en not_active Expired
- 1976-01-12 BR BR7600132A patent/BR7600132A/pt unknown
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268299A (en) * | 1978-08-17 | 1981-05-19 | Monsanto Company | Method and composition for plant growth regulation containing trifluoromethyl 1,3,4 oxadiazol benzoates |
| US4210762A (en) * | 1978-08-17 | 1980-07-01 | Monsanto Company | 2[5-(3-Trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl] benzoates |
| US4209629A (en) * | 1978-12-20 | 1980-06-24 | Monsanto Company | 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones |
| US4364768A (en) | 1978-12-20 | 1982-12-21 | Monsanto Company | 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as plant growth regulants |
| US4208510A (en) * | 1978-12-20 | 1980-06-17 | Monsanto Company | Preparation of 3-aryl-isoxazol-5-yl benzoates |
| US4197405A (en) * | 1979-02-22 | 1980-04-08 | Monsanto Company | Thermolysis of 3'-(Aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one |
| US4223154A (en) * | 1979-03-09 | 1980-09-16 | Monsanto Company | Preparation of 2-(3-aryl-5-isoxazol) benzoyl halide |
| US4230866A (en) * | 1979-05-17 | 1980-10-28 | Monsanto Company | Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof |
| US4401457A (en) | 1980-06-18 | 1983-08-30 | Monsanto Company | 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as herbicides |
| US9611230B2 (en) | 2004-10-13 | 2017-04-04 | Ptc Therapeutics, Inc. | 1,3,4-oxadiazole benzoic acid compounds and their use for nonsense suppression and the treatment of disease |
| JP2008515985A (ja) * | 2004-10-13 | 2008-05-15 | ピーティーシー セラピューティクス，インコーポレーテッド | ナンセンス抑制の化合物とその使用方法 |
| JP2011525534A (ja) * | 2008-06-24 | 2011-09-22 | アイアールエム・リミテッド・ライアビリティ・カンパニー | Ｇタンパク質共役受容体を調節するための化合物および方法 |
| CN114773330A (zh) * | 2022-05-24 | 2022-07-22 | 贵州医科大学 | 丁苯酞-噁/噻二唑类化合物及其制备方法和应用 |
| CN114773330B (zh) * | 2022-05-24 | 2024-03-15 | 贵州医科大学 | 丁苯酞-噁/噻二唑类化合物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ179684A (en) | 1978-04-03 |
| BR7600132A (pt) | 1976-08-03 |
| DE2600655A1 (de) | 1976-07-15 |
| CH603044A5 (enrdf_load_stackoverflow) | 1978-08-15 |
| IT1054759B (it) | 1981-11-30 |
| IL48803A0 (en) | 1976-03-31 |
| CA1066708A (en) | 1979-11-20 |
| ZA7638B (en) | 1976-12-29 |
| FR2332705A1 (fr) | 1977-06-24 |
| BE837454A (fr) | 1976-07-09 |
| NL7600152A (nl) | 1976-07-13 |
| AU1007876A (en) | 1977-07-14 |
| AU497898B2 (en) | 1979-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SP | Amendment (slips) printed | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |