DK142752B - Analogifremgangsmåde til fremstilling af phosphonoureido- eller phosphonothioureidoarenforbindelser. - Google Patents
Analogifremgangsmåde til fremstilling af phosphonoureido- eller phosphonothioureidoarenforbindelser. Download PDFInfo
- Publication number
- DK142752B DK142752B DK290373AA DK290373A DK142752B DK 142752 B DK142752 B DK 142752B DK 290373A A DK290373A A DK 290373AA DK 290373 A DK290373 A DK 290373A DK 142752 B DK142752 B DK 142752B
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- general formula
- compounds
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- compound
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- 150000001875 compounds Chemical class 0.000 title claims description 68
- -1 Phosphonoureido Chemical group 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 17
- 150000002540 isothiocyanates Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- ADNODBYTFORIQQ-UHFFFAOYSA-N isocyanatophosphonic acid Chemical compound OP(O)(=O)N=C=O ADNODBYTFORIQQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 1
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- 229910052799 carbon Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
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- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical class S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 3
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
- ZACBJJDJJBGIDC-UHFFFAOYSA-N n-(sulfanylidenemethylidene)benzenesulfonamide Chemical class S=C=NS(=O)(=O)C1=CC=CC=C1 ZACBJJDJJBGIDC-UHFFFAOYSA-N 0.000 description 3
- 244000045947 parasite Species 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BSCBJDQIQBYMBT-UHFFFAOYSA-N 1-[ethoxy(isocyanato)phosphoryl]oxyethane Chemical compound CCOP(=O)(OCC)N=C=O BSCBJDQIQBYMBT-UHFFFAOYSA-N 0.000 description 2
- 241000244188 Ascaris suum Species 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
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- 241000242680 Schistosoma mansoni Species 0.000 description 2
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- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 2
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- 230000000378 dietary effect Effects 0.000 description 2
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 2
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- FNNCNKGXXMCXNR-UHFFFAOYSA-N isothiocyanatophosphonic acid Chemical class OP(O)(=O)N=C=S FNNCNKGXXMCXNR-UHFFFAOYSA-N 0.000 description 2
- VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KMJYFAKEXUMBGA-UHFFFAOYSA-N n-[amino(ethylamino)phosphoryl]ethanamine Chemical compound CCNP(N)(=O)NCC KMJYFAKEXUMBGA-UHFFFAOYSA-N 0.000 description 2
- XTBLDMQMUSHDEN-UHFFFAOYSA-N naphthalene-2,3-diamine Chemical compound C1=CC=C2C=C(N)C(N)=CC2=C1 XTBLDMQMUSHDEN-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
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- ZWYSLPOHOBPSLC-UHFFFAOYSA-N n-benzoyl-n'-phenylurea Chemical class C=1C=CC=CC=1NC(=O)NC(=O)C1=CC=CC=C1 ZWYSLPOHOBPSLC-UHFFFAOYSA-N 0.000 description 1
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- VPRFQZSTJXHBHL-UHFFFAOYSA-N phenanthrene-9,10-diamine Chemical compound C1=CC=C2C(N)=C(N)C3=CC=CC=C3C2=C1 VPRFQZSTJXHBHL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2487—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-C(=X) (X = O, S, Se; n = 0, 1)
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/16—Derivatives of isocyanic acid having isocyanate groups acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/32—Isothiocyanates having isothiocyanate groups acylated
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25942372A | 1972-05-26 | 1972-05-26 | |
| US25942372 | 1972-05-26 | ||
| US26337872A | 1972-06-05 | 1972-06-05 | |
| US26337872 | 1972-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK142752B true DK142752B (da) | 1981-01-12 |
Family
ID=26947293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK290373AA DK142752B (da) | 1972-05-26 | 1973-05-25 | Analogifremgangsmåde til fremstilling af phosphonoureido- eller phosphonothioureidoarenforbindelser. |
Country Status (20)
| Country | Link |
|---|---|
| AR (2) | AR207848A1 (ro) |
| AT (1) | AT326145B (ro) |
| AU (1) | AU474515B2 (ro) |
| BE (1) | BE800041A (ro) |
| CH (1) | CH574451A5 (ro) |
| CS (1) | CS193022B2 (ro) |
| DD (1) | DD105441A5 (ro) |
| DE (1) | DE2325036C3 (ro) |
| DK (1) | DK142752B (ro) |
| ES (1) | ES415199A1 (ro) |
| FR (1) | FR2187336A1 (ro) |
| HU (1) | HU169608B (ro) |
| IE (1) | IE37689B1 (ro) |
| IL (1) | IL42355A (ro) |
| IN (1) | IN139086B (ro) |
| LU (1) | LU67672A1 (ro) |
| NL (1) | NL7307291A (ro) |
| OA (1) | OA04407A (ro) |
| SE (1) | SE411758B (ro) |
| SU (1) | SU536755A3 (ro) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4086336A (en) * | 1972-05-26 | 1978-04-25 | Rohm And Haas Company | Phosphonothioureide anthelmintics |
| DE2841668A1 (de) * | 1978-09-25 | 1980-04-10 | Bayer Ag | Medikiertes tierfutter auf basis lebermehl |
| EP3668840A1 (en) | 2017-08-15 | 2020-06-24 | Inflazome Limited | Novel sulfonamide carboxamide compounds |
-
1973
- 1973-05-16 OA OA54909A patent/OA04407A/xx unknown
- 1973-05-17 DE DE2325036A patent/DE2325036C3/de not_active Expired
- 1973-05-24 SE SE7307360A patent/SE411758B/xx unknown
- 1973-05-24 NL NL7307291A patent/NL7307291A/xx not_active Application Discontinuation
- 1973-05-25 IL IL197342355A patent/IL42355A/en unknown
- 1973-05-25 AU AU56165/73A patent/AU474515B2/en not_active Expired
- 1973-05-25 ES ES415199A patent/ES415199A1/es not_active Expired
- 1973-05-25 LU LU67672A patent/LU67672A1/xx unknown
- 1973-05-25 BE BE131524A patent/BE800041A/xx unknown
- 1973-05-25 IN IN1229/CAL/73A patent/IN139086B/en unknown
- 1973-05-25 CS CS733805A patent/CS193022B2/cs unknown
- 1973-05-25 AR AR253139A patent/AR207848A1/es active
- 1973-05-25 IE IE844/73A patent/IE37689B1/xx unknown
- 1973-05-25 DK DK290373AA patent/DK142752B/da unknown
- 1973-05-25 DD DD171078A patent/DD105441A5/xx unknown
- 1973-05-25 AR AR248135A patent/AR207742A1/es active
- 1973-05-25 CH CH756973A patent/CH574451A5/xx not_active IP Right Cessation
- 1973-05-25 AT AT458873A patent/AT326145B/de not_active IP Right Cessation
- 1973-05-25 HU HURO733A patent/HU169608B/hu unknown
- 1973-05-25 FR FR7319183A patent/FR2187336A1/fr active Granted
- 1973-06-04 SU SU731926076A patent/SU536755A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| ES415199A1 (es) | 1976-06-01 |
| HU169608B (ro) | 1976-12-28 |
| CS193022B2 (en) | 1979-09-17 |
| IL42355A (en) | 1977-12-30 |
| DD105441A5 (ro) | 1974-04-20 |
| ATA458873A (de) | 1975-02-15 |
| LU67672A1 (ro) | 1973-12-04 |
| FR2187336B1 (ro) | 1977-01-28 |
| IE37689L (en) | 1973-12-05 |
| SU536755A3 (ru) | 1976-11-25 |
| DE2325036A1 (de) | 1974-01-03 |
| AR207742A1 (es) | 1976-10-29 |
| IL42355A0 (en) | 1973-07-30 |
| AR207848A1 (es) | 1976-11-08 |
| AU5616573A (en) | 1974-11-28 |
| AU474515B2 (en) | 1976-07-22 |
| DE2325036B2 (de) | 1980-03-13 |
| FR2187336A1 (en) | 1974-01-18 |
| NL7307291A (ro) | 1973-12-07 |
| OA04407A (fr) | 1980-02-29 |
| IE37689B1 (en) | 1977-09-14 |
| SE411758B (sv) | 1980-02-04 |
| CH574451A5 (ro) | 1976-04-15 |
| IN139086B (ro) | 1976-05-08 |
| AT326145B (de) | 1975-11-25 |
| BE800041A (fr) | 1973-11-26 |
| DE2325036C3 (de) | 1980-11-06 |
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