GB1448996A - 1,2,4-triazole derivatives - Google Patents
1,2,4-triazole derivativesInfo
- Publication number
- GB1448996A GB1448996A GB5689273A GB5689273A GB1448996A GB 1448996 A GB1448996 A GB 1448996A GB 5689273 A GB5689273 A GB 5689273A GB 5689273 A GB5689273 A GB 5689273A GB 1448996 A GB1448996 A GB 1448996A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- prepared
- alkyl
- alkoxycarbonylisothiocyanate
- dec
- 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
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000000178 1,2,4-triazoles Chemical class 0.000 abstract 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 abstract 1
- JFYLDUJXNYTCSN-UHFFFAOYSA-N 2-methyl-3-prop-2-ynylsulfanyl-1h-1,2,4-triazol-5-one Chemical compound CN1N=C(O)N=C1SCC#C JFYLDUJXNYTCSN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 abstract 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004344 phenylpropyl group Chemical group 0.000 abstract 1
- 125000003367 polycyclic group Polymers 0.000 abstract 1
- RFAKLMBNSZNUNX-UHFFFAOYSA-N potassium;isothiocyanate Chemical compound [K+].[N-]=C=S RFAKLMBNSZNUNX-UHFFFAOYSA-N 0.000 abstract 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 abstract 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1448996 Triazole derivatives CIBA-GEIGY AG 7 Dec 1973 [8 Dec 1972] 56892/73 Headings C2C and C2P Novel 1,2,4-triazoles of formula where R is unsubstituted or substituted alkyl, alkenyl, phenyl, naphthyl, benzyl, phenylethyl, phenylpropyl or mono- or poly-cyclic cycloalkyl which can be bound by way of an alkylene bridge member, and also compounds in which R is H, are prepared by reacting a hydrazine RNHNH 2 or a salt thereof with an alkoxycarbonylisothiocyanate alkyl-O-CO-NCS and heating the resulting thiosemicarbazide of formula with or without isolation or by reacting the alkoxycarbonylisothiocyanate with a hydrazone RNHN = CR 1 R 2 to give a thiosemicarbazone of formula and heating this in aqueous medium. Ethoxycarbonylisothiocyanate is prepared from ethyl chloroformate and potassium isothiocyanate. Compounds of formula II in which R is CH 3 or isopropyl and alkyl is ethyl and of Formula III in which R 1 = R 2 = CH 3 and R = Et, isopropyl or phenyl are isolated. 1 - Methyl - 3 - hydroxy - 5 - propargyl - mercapto- 1,2,4-triazole is prepared from propargyl bromide and the corresponding mercaptotriazole, and is further reacted with (EtO) 2 P(S)Cl to give O,O - diethyl - O - (1 - methyl - 5 - propargylthio- 1,2,4-triazolyl-(3) thiophosphate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1789772A CH574428A5 (en) | 1972-12-08 | 1972-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1448996A true GB1448996A (en) | 1976-09-08 |
Family
ID=4428906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5689273A Expired GB1448996A (en) | 1972-12-08 | 1973-12-07 | 1,2,4-triazole derivatives |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4987675A (en) |
| BE (1) | BE878583Q (en) |
| CH (1) | CH574428A5 (en) |
| DE (1) | DE2360623A1 (en) |
| FR (1) | FR2209760B1 (en) |
| GB (1) | GB1448996A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4616004A (en) * | 1984-09-27 | 1986-10-07 | Chevron Research Company | 1-iodopropargyl-3,4-disubstituted-Δ2 -1,2,4-triazolidin-5-one fungicides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681374A (en) * | 1970-08-11 | 1972-08-01 | Asahi Chemical Ind | Synthetic nacreous triazole crystals and method for production thereof |
-
1972
- 1972-12-08 CH CH1789772A patent/CH574428A5/xx not_active IP Right Cessation
-
1973
- 1973-12-05 DE DE2360623A patent/DE2360623A1/en not_active Ceased
- 1973-12-06 JP JP48138543A patent/JPS4987675A/ja active Pending
- 1973-12-07 GB GB5689273A patent/GB1448996A/en not_active Expired
- 1973-12-07 FR FR7343688A patent/FR2209760B1/fr not_active Expired
-
1979
- 1979-09-04 BE BE0/197000A patent/BE878583Q/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2360623A1 (en) | 1974-06-12 |
| JPS4987675A (en) | 1974-08-22 |
| BE878583Q (en) | 1979-12-31 |
| FR2209760A1 (en) | 1974-07-05 |
| FR2209760B1 (en) | 1977-06-10 |
| CH574428A5 (en) | 1976-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |