GB1571905A - N-arylsulphonyl carbamates - Google Patents
N-arylsulphonyl carbamates Download PDFInfo
- Publication number
- GB1571905A GB1571905A GB21016/79A GB2101679A GB1571905A GB 1571905 A GB1571905 A GB 1571905A GB 21016/79 A GB21016/79 A GB 21016/79A GB 2101679 A GB2101679 A GB 2101679A GB 1571905 A GB1571905 A GB 1571905A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- substituted
- bromo
- compound
- alkyl
- 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 24
- -1 chloro, bromo, methoxy Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 241000605281 Anaplasma phagocytophilum Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003815 herbicide antidote Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 description 1
- LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 1
- JGHDVROWMPBQSR-UHFFFAOYSA-N 4-chloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C=C1 JGHDVROWMPBQSR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 0.000 description 1
- GOIXTLOQOLARST-UHFFFAOYSA-N carbamoyl 3-but-1-ynyl-4-methylbenzenesulfonate Chemical compound CCC#CC1=CC(S(=O)(=O)OC(N)=O)=CC=C1C GOIXTLOQOLARST-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61911475A | 1975-10-02 | 1975-10-02 | |
| US05/721,721 US4230874A (en) | 1976-09-13 | 1976-09-13 | N-(Benzenesulfonyl) carbamates-herbicidal antidotes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1571905A true GB1571905A (en) | 1980-07-23 |
Family
ID=27088427
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21016/79A Expired GB1571905A (en) | 1975-10-02 | 1976-10-01 | N-arylsulphonyl carbamates |
| GB40797/76A Expired GB1571904A (en) | 1975-10-02 | 1976-10-01 | Use of n-arylsulphonyl carbamates as herbicide antidotes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40797/76A Expired GB1571904A (en) | 1975-10-02 | 1976-10-01 | Use of n-arylsulphonyl carbamates as herbicide antidotes |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5919533B2 (da) |
| AR (1) | AR217244A1 (da) |
| AU (1) | AU509009B2 (da) |
| BR (1) | BR7606642A (da) |
| CA (1) | CA1097649A (da) |
| CH (1) | CH629081A5 (da) |
| DD (1) | DD127619A5 (da) |
| DE (1) | DE2644504A1 (da) |
| DK (1) | DK442876A (da) |
| ES (1) | ES452285A1 (da) |
| FR (1) | FR2326414A1 (da) |
| GB (2) | GB1571905A (da) |
| GR (1) | GR65992B (da) |
| HU (1) | HU179643B (da) |
| IL (1) | IL50595A (da) |
| IN (1) | IN145026B (da) |
| IT (1) | IT1073910B (da) |
| MX (1) | MX5392E (da) |
| NL (1) | NL7610893A (da) |
| NZ (1) | NZ182204A (da) |
| PT (1) | PT65663B (da) |
| RO (1) | RO72913A (da) |
| TR (1) | TR19020A (da) |
| YU (2) | YU241876A (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2690918B1 (fr) * | 1992-05-06 | 2001-12-28 | Poudres & Explosifs Ste Nale | Utilisation d'un arylsulfonyluréthanne comme résine garnissante dans les vernis à ongles nitrocellulosiques. Nouveaux arylsulfonyluréthannes et nouveaux vernis à ongles nitrocellulosiques. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799760A (en) * | 1966-05-03 | 1974-03-26 | Monsanto Co | Method for inhibiting plant growth |
-
1976
- 1976-09-30 PT PT65663A patent/PT65663B/pt unknown
- 1976-10-01 DE DE19762644504 patent/DE2644504A1/de not_active Withdrawn
- 1976-10-01 AU AU18328/76A patent/AU509009B2/en not_active Ceased
- 1976-10-01 YU YU02418/76A patent/YU241876A/xx unknown
- 1976-10-01 IL IL50595A patent/IL50595A/xx unknown
- 1976-10-01 FR FR7629553A patent/FR2326414A1/fr active Granted
- 1976-10-01 GB GB21016/79A patent/GB1571905A/en not_active Expired
- 1976-10-01 TR TR19020A patent/TR19020A/xx unknown
- 1976-10-01 HU HU76SA2981A patent/HU179643B/hu unknown
- 1976-10-01 NZ NZ182204A patent/NZ182204A/xx unknown
- 1976-10-01 GR GR51819A patent/GR65992B/el unknown
- 1976-10-01 IT IT51532/76A patent/IT1073910B/it active
- 1976-10-01 NL NL7610893A patent/NL7610893A/xx not_active Application Discontinuation
- 1976-10-01 CA CA262,510A patent/CA1097649A/en not_active Expired
- 1976-10-01 GB GB40797/76A patent/GB1571904A/en not_active Expired
- 1976-10-01 DK DK442876A patent/DK442876A/da not_active Application Discontinuation
- 1976-10-02 RO RO7687889A patent/RO72913A/ro unknown
- 1976-10-02 DD DD195122A patent/DD127619A5/xx unknown
- 1976-10-02 JP JP51118906A patent/JPS5919533B2/ja not_active Expired
- 1976-10-04 IN IN1813/CAL/76A patent/IN145026B/en unknown
- 1976-10-04 CH CH1253676A patent/CH629081A5/de not_active IP Right Cessation
- 1976-10-04 AR AR264968A patent/AR217244A1/es active
- 1976-10-04 BR BR7606642A patent/BR7606642A/pt unknown
- 1976-10-04 MX MX764953U patent/MX5392E/es unknown
- 1976-10-09 ES ES452285A patent/ES452285A1/es not_active Expired
-
1982
- 1982-04-15 YU YU01306/82A patent/YU130682A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1097649A (en) | 1981-03-17 |
| AR217244A1 (es) | 1980-03-14 |
| JPS5919533B2 (ja) | 1984-05-07 |
| MX5392E (es) | 1983-07-08 |
| TR19020A (tr) | 1978-02-27 |
| AU1832876A (en) | 1978-04-06 |
| GR65992B (da) | 1981-01-13 |
| YU130682A (en) | 1983-01-21 |
| IN145026B (da) | 1978-08-12 |
| FR2326414A1 (fr) | 1977-04-29 |
| ES452285A1 (es) | 1978-03-01 |
| YU241876A (en) | 1983-02-28 |
| RO72913A (ro) | 1981-09-24 |
| PT65663A (fr) | 1976-10-01 |
| BR7606642A (pt) | 1977-11-16 |
| NL7610893A (nl) | 1977-04-05 |
| DE2644504A1 (de) | 1977-06-02 |
| NZ182204A (en) | 1979-07-11 |
| CH629081A5 (en) | 1982-04-15 |
| DD127619A5 (da) | 1977-10-05 |
| FR2326414B1 (da) | 1981-05-22 |
| IL50595A (en) | 1981-07-31 |
| DK442876A (da) | 1977-04-03 |
| AU509009B2 (en) | 1980-04-17 |
| IL50595A0 (en) | 1976-12-31 |
| PT65663B (fr) | 1978-04-11 |
| JPS5265247A (en) | 1977-05-30 |
| HU179643B (en) | 1982-11-29 |
| GB1571904A (en) | 1980-07-23 |
| IT1073910B (it) | 1985-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |