DE1163828B - Verfahren zur Herstellung von Fluor-dichlormethansulfensaeureestern oder -amiden - Google Patents
Verfahren zur Herstellung von Fluor-dichlormethansulfensaeureestern oder -amidenInfo
- Publication number
- DE1163828B DE1163828B DEF35277A DEF0035277A DE1163828B DE 1163828 B DE1163828 B DE 1163828B DE F35277 A DEF35277 A DE F35277A DE F0035277 A DEF0035277 A DE F0035277A DE 1163828 B DE1163828 B DE 1163828B
- Authority
- DE
- Germany
- Prior art keywords
- radical
- amides
- dichloromethanesulfenic
- fluoro
- acid esters
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000001408 amides Chemical class 0.000 title claims description 4
- HFMYRCYWBSNXAI-UHFFFAOYSA-N dichloro-fluoro-hydroxysulfanylmethane Chemical class FC(SO)(Cl)Cl HFMYRCYWBSNXAI-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012991 xanthate Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- -1 heterocyclic Alcohols Chemical class 0.000 description 7
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical class CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/78—Sulfur atoms attached to a second hetero atom to a second sulphur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE624304D BE624304A (en, 2012) | 1961-11-03 | ||
| NL285032D NL285032A (en, 2012) | 1961-11-03 | ||
| DEF35277A DE1163828B (de) | 1961-11-03 | 1961-11-03 | Verfahren zur Herstellung von Fluor-dichlormethansulfensaeureestern oder -amiden |
| CH1208462A CH424760A (de) | 1961-11-03 | 1962-10-15 | Verfahren zur Herstellung von Derivaten der Fluor-dichlor-methansulfensäure |
| US231036A US3251850A (en) | 1961-11-03 | 1962-10-16 | Certain fluoro-dichloromethyldithiobenzazole compounds |
| DK468262AA DK108102C (da) | 1961-11-03 | 1962-10-30 | Middel til bekæmpelse af skadelige organismer og fremgangsmåde til fremstilling af fluormethansulfensyrederivater til anvendelse i midlet. |
| BR144293/62A BR6244293D0 (pt) | 1961-11-03 | 1962-10-31 | Processo para a producao de derivados organicos do acido fluor-di-cloro-metano-sulfenico e composicoes praguicidas nelas baseadas |
| GB41545/62A GB953688A (en) | 1961-11-03 | 1962-11-02 | Derivatives of fluoro-dichloro-methane sulphenic acid |
| FR914246A FR1339765A (fr) | 1961-11-03 | 1962-11-02 | Procédé de préparation de dérivés de l'acide fluorodichlorométhane-sulfénique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35277A DE1163828B (de) | 1961-11-03 | 1961-11-03 | Verfahren zur Herstellung von Fluor-dichlormethansulfensaeureestern oder -amiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1163828B true DE1163828B (de) | 1964-02-27 |
Family
ID=7095938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF35277A Pending DE1163828B (de) | 1961-11-03 | 1961-11-03 | Verfahren zur Herstellung von Fluor-dichlormethansulfensaeureestern oder -amiden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3251850A (en, 2012) |
| BE (1) | BE624304A (en, 2012) |
| BR (1) | BR6244293D0 (en, 2012) |
| CH (1) | CH424760A (en, 2012) |
| DE (1) | DE1163828B (en, 2012) |
| DK (1) | DK108102C (en, 2012) |
| GB (1) | GB953688A (en, 2012) |
| NL (1) | NL285032A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1238139B (de) * | 1964-04-11 | 1967-04-06 | Bayer Ag | Mikrobizide Mittel fuer Anstriche und Kunststoffueberzuege |
| US4438117A (en) | 1980-09-03 | 1984-03-20 | E. I. Du Pont De Nemours And Company | 2-Substituted thio-4,5-diarylpyrimidines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553777A (en) * | 1949-11-08 | 1951-05-22 | Standard Oil Dev Co | Parasiticidal compositions containing substituted dithiotrichloro methanes |
| US2862946A (en) * | 1956-04-02 | 1958-12-02 | Stauffer Chemical Co | Esters of sulfenic acids and their preparation |
| FR1241754A (fr) * | 1958-08-04 | 1960-09-23 | Du Pont | Procédé de fabrication de 2-(fluorométhylthio)-zoogénazols |
-
0
- BE BE624304D patent/BE624304A/xx unknown
- NL NL285032D patent/NL285032A/xx unknown
-
1961
- 1961-11-03 DE DEF35277A patent/DE1163828B/de active Pending
-
1962
- 1962-10-15 CH CH1208462A patent/CH424760A/de unknown
- 1962-10-16 US US231036A patent/US3251850A/en not_active Expired - Lifetime
- 1962-10-30 DK DK468262AA patent/DK108102C/da active
- 1962-10-31 BR BR144293/62A patent/BR6244293D0/pt unknown
- 1962-11-02 GB GB41545/62A patent/GB953688A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3251850A (en) | 1966-05-17 |
| NL285032A (en, 2012) | |
| GB953688A (en) | 1964-03-25 |
| DK108102C (da) | 1967-08-28 |
| BE624304A (en, 2012) | |
| CH424760A (de) | 1966-11-30 |
| BR6244293D0 (pt) | 1973-05-15 |
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