CA1162557A - Method for making thiobiscarbamates - Google Patents
Method for making thiobiscarbamatesInfo
- Publication number
- CA1162557A CA1162557A CA000359569A CA359569A CA1162557A CA 1162557 A CA1162557 A CA 1162557A CA 000359569 A CA000359569 A CA 000359569A CA 359569 A CA359569 A CA 359569A CA 1162557 A CA1162557 A CA 1162557A
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- sulfur chloride
- methyl
- reacting
- base
- 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
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims abstract 9
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims abstract 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract 3
- 239000002904 solvent Substances 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 3
- 229910018105 SCl2 Inorganic materials 0.000 claims 3
- 101001135436 Urodacus yaschenkoi Antimicrobial peptide scorpine-like-2 Proteins 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 239000008096 xylene Substances 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
- WYCOXPGSSCZRRC-UHFFFAOYSA-N chloro thiohypochlorite Chemical compound S(Cl)Cl.S(Cl)Cl WYCOXPGSSCZRRC-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000005916 Methomyl Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 abstract 1
- -1 methomyl Chemical compound 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US070,535 | 1979-09-05 | ||
| US06/070,535 US4256655A (en) | 1979-09-05 | 1979-09-05 | Method for making thiobiscarbamates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1162557A true CA1162557A (en) | 1984-02-21 |
Family
ID=22095870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000359569A Expired CA1162557A (en) | 1979-09-05 | 1980-09-04 | Method for making thiobiscarbamates |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4256655A (OSRAM) |
| EP (1) | EP0025354B1 (OSRAM) |
| JP (1) | JPS633856B2 (OSRAM) |
| AU (1) | AU6390180A (OSRAM) |
| CA (1) | CA1162557A (OSRAM) |
| DE (1) | DE3065060D1 (OSRAM) |
| DK (1) | DK199981A (OSRAM) |
| HU (1) | HU183434B (OSRAM) |
| WO (1) | WO1981000713A1 (OSRAM) |
| ZA (1) | ZA805345B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3173912D1 (en) * | 1981-11-23 | 1986-04-03 | Union Carbide Corp | Method for making thiobiscarbamates |
| US4495093A (en) * | 1982-04-15 | 1985-01-22 | Union Carbide Corporation | Process for making thiobiscarbamates |
| CN108047106B (zh) * | 2017-12-26 | 2020-07-14 | 湖南海利常德农药化工有限公司 | 硫双灭多威的制备方法 |
| CN111054296A (zh) * | 2019-12-02 | 2020-04-24 | 河南金鹏化工有限公司 | 一种硫双威盐化反应连续化生产装置及工艺 |
| CN112778179B (zh) * | 2021-01-29 | 2022-11-04 | 湖南海利常德农药化工有限公司 | 一种硫双灭多威的合成方法 |
| CN114315672B (zh) * | 2021-12-14 | 2023-09-22 | 山东第一医科大学(山东省医学科学院) | 一种高灭多威转化率的硫双威合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2530439C2 (de) * | 1974-07-11 | 1983-03-03 | CIBA-GEIGY AG, 4002 Basel | Bis-[0-(1-Alkylthio-äthylimino)-N-methyl-carbaminsäure]-N,N'-sulfide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Schädlingsbekämpfungsmittel |
-
1979
- 1979-09-05 US US06/070,535 patent/US4256655A/en not_active Expired - Lifetime
-
1980
- 1980-08-28 ZA ZA00805345A patent/ZA805345B/xx unknown
- 1980-09-04 CA CA000359569A patent/CA1162557A/en not_active Expired
- 1980-09-04 WO PCT/US1980/001138 patent/WO1981000713A1/en not_active Ceased
- 1980-09-04 JP JP55502143A patent/JPS633856B2/ja not_active Expired
- 1980-09-04 HU HU801313A patent/HU183434B/hu unknown
- 1980-09-04 AU AU63901/80A patent/AU6390180A/en not_active Abandoned
- 1980-09-05 DE DE8080303138T patent/DE3065060D1/de not_active Expired
- 1980-09-05 EP EP80303138A patent/EP0025354B1/en not_active Expired
- 1980-10-21 US US06/199,382 patent/US4323516A/en not_active Expired - Lifetime
-
1981
- 1981-05-05 DK DK199981A patent/DK199981A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56501203A (OSRAM) | 1981-08-27 |
| US4256655A (en) | 1981-03-17 |
| JPS633856B2 (OSRAM) | 1988-01-26 |
| US4323516A (en) | 1982-04-06 |
| EP0025354B1 (en) | 1983-09-28 |
| AU6390180A (en) | 1981-03-31 |
| DE3065060D1 (en) | 1983-11-03 |
| EP0025354A3 (en) | 1981-07-15 |
| EP0025354A2 (en) | 1981-03-18 |
| WO1981000713A1 (en) | 1981-03-19 |
| HU183434B (en) | 1984-05-28 |
| DK199981A (da) | 1981-05-05 |
| ZA805345B (en) | 1981-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |