DE1115738B - Verfahren zur Herstellung von offenkettigen oder cyclischen Chinoxalino-2, 3-thiophosphorsaeureestern - Google Patents
Verfahren zur Herstellung von offenkettigen oder cyclischen Chinoxalino-2, 3-thiophosphorsaeureesternInfo
- Publication number
- DE1115738B DE1115738B DEF28877A DEF0028877A DE1115738B DE 1115738 B DE1115738 B DE 1115738B DE F28877 A DEF28877 A DE F28877A DE F0028877 A DEF0028877 A DE F0028877A DE 1115738 B DE1115738 B DE 1115738B
- Authority
- DE
- Germany
- Prior art keywords
- cyclic
- acid esters
- quinoxalino
- chain
- preparation
- 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
- 125000004122 cyclic group Chemical group 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- YFBUDXNMBTUSOC-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dithione Chemical class C1=CC=C2NC(=S)C(=S)NC2=C1 YFBUDXNMBTUSOC-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- -1 diester halides Chemical class 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WPIVYVMXORGSSY-UHFFFAOYSA-N 6-nitro-1,4-dihydroquinoxaline-2,3-dithione Chemical compound N1=C(S)C(S)=NC2=CC([N+](=O)[O-])=CC=C21 WPIVYVMXORGSSY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- ILXZMTJXXHNZJS-UHFFFAOYSA-N diethyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(=O)OCC ILXZMTJXXHNZJS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003449 sulfenic acid halides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
- C07F9/650994—Six-membered rings having the nitrogen atoms in the positions 1 and 4 condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
- C07F9/657127—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s) condensed with carbocyclic or heterocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE592836D BE592836A (US20110009641A1-20110113-C00256.png) | 1959-07-09 | ||
| NL253535D NL253535A (US20110009641A1-20110113-C00256.png) | 1959-07-09 | ||
| DEF28877A DE1115738B (de) | 1959-07-09 | 1959-07-09 | Verfahren zur Herstellung von offenkettigen oder cyclischen Chinoxalino-2, 3-thiophosphorsaeureestern |
| CH724360A CH390261A (de) | 1959-07-09 | 1960-06-27 | Verfahren zur Herstellung von Thiophosphorsäureestern |
| US41039A US3029237A (en) | 1959-07-09 | 1960-07-06 | Quinoxolinyl thiophosphoric acid esters |
| GB23840/60A GB894163A (en) | 1959-07-09 | 1960-07-07 | Thiophosphoric acid esters |
| FR832557A FR1262308A (fr) | 1959-07-09 | 1960-07-09 | Procédé de préparation d'esters thiophosphoriques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28877A DE1115738B (de) | 1959-07-09 | 1959-07-09 | Verfahren zur Herstellung von offenkettigen oder cyclischen Chinoxalino-2, 3-thiophosphorsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1115738B true DE1115738B (de) | 1961-10-26 |
Family
ID=7093068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28877A Pending DE1115738B (de) | 1959-07-09 | 1959-07-09 | Verfahren zur Herstellung von offenkettigen oder cyclischen Chinoxalino-2, 3-thiophosphorsaeureestern |
Country Status (7)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL291448A (US20110009641A1-20110113-C00256.png) * | 1962-04-12 | |||
| BE788358A (fr) * | 1971-09-04 | 1973-03-05 | Bayer Ag | Nouveaux esters de quinoxalyle d'acides (thiono)- phosphoriques(phosphoniques), leur procede de preparation et leur application comme insecticides et acaricides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE927270C (de) * | 1953-02-26 | 1955-05-02 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2919985A (en) * | 1958-08-15 | 1960-01-05 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsions |
-
0
- BE BE592836D patent/BE592836A/xx unknown
- NL NL253535D patent/NL253535A/xx unknown
-
1959
- 1959-07-09 DE DEF28877A patent/DE1115738B/de active Pending
-
1960
- 1960-06-27 CH CH724360A patent/CH390261A/de unknown
- 1960-07-06 US US41039A patent/US3029237A/en not_active Expired - Lifetime
- 1960-07-07 GB GB23840/60A patent/GB894163A/en not_active Expired
- 1960-07-09 FR FR832557A patent/FR1262308A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE927270C (de) * | 1953-02-26 | 1955-05-02 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
Also Published As
| Publication number | Publication date |
|---|---|
| US3029237A (en) | 1962-04-10 |
| FR1262308A (fr) | 1961-05-26 |
| GB894163A (en) | 1962-04-18 |
| CH390261A (de) | 1965-04-15 |
| NL253535A (US20110009641A1-20110113-C00256.png) | |
| BE592836A (US20110009641A1-20110113-C00256.png) |
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