DE1127892B - Verfahren zur Herstellung von Thiophosphorsaeureestern - Google Patents
Verfahren zur Herstellung von ThiophosphorsaeureesternInfo
- Publication number
- DE1127892B DE1127892B DEF31173A DEF0031173A DE1127892B DE 1127892 B DE1127892 B DE 1127892B DE F31173 A DEF31173 A DE F31173A DE F0031173 A DEF0031173 A DE F0031173A DE 1127892 B DE1127892 B DE 1127892B
- Authority
- DE
- Germany
- Prior art keywords
- ester
- added
- hour
- heated
- sulfur
- 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 13
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 239000011593 sulfur Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 150000002148 esters Chemical class 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 21
- 241000700159 Rattus Species 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- 230000001988 toxicity Effects 0.000 description 19
- 231100000419 toxicity Toxicity 0.000 description 19
- 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 17
- 241001454295 Tetranychidae Species 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- 241001124076 Aphididae Species 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000003756 stirring Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- GWMWXFGQYATKBA-UHFFFAOYSA-N 4-methyl-2-sulfanylphenol Chemical compound CC1=CC=C(O)C(S)=C1 GWMWXFGQYATKBA-UHFFFAOYSA-N 0.000 description 3
- 206010004194 Bed bug infestation Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001414835 Cimicidae Species 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- 230000003151 ovacidal effect Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 241000239290 Araneae Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 nitroalkyl alcohols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- NUTVORGGYDQIDD-UHFFFAOYSA-N 1-ethylsulfanylethanol Chemical compound CCSC(C)O NUTVORGGYDQIDD-UHFFFAOYSA-N 0.000 description 1
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- DKTRZBWXGOPYIX-UHFFFAOYSA-N 3-chloro-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C(Cl)=C1 DKTRZBWXGOPYIX-UHFFFAOYSA-N 0.000 description 1
- VKALYYFVKBXHTF-UHFFFAOYSA-N 4-(methylsulfanyl)-m-cresol Chemical compound CSC1=CC=C(O)C=C1C VKALYYFVKBXHTF-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- NIAAGQAEVGMHPM-UHFFFAOYSA-N 4-methylbenzene-1,2-dithiol Chemical compound CC1=CC=C(S)C(S)=C1 NIAAGQAEVGMHPM-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 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
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
- G21F7/00—Shielded cells or rooms
- G21F7/005—Shielded passages through walls; Locks; Transferring devices between rooms
-
- 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
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/201—Esters of thiophosphorus acids
- C07F9/206—Esters of thiophosphorus acids containing P-halide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Physics & Mathematics (AREA)
- General Engineering & Computer Science (AREA)
- High Energy & Nuclear Physics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL264380D NL264380A (US20080094685A1-20080424-C00004.png) | 1960-05-06 | ||
BE603613D BE603613A (US20080094685A1-20080424-C00004.png) | 1960-05-06 | ||
DEF31173A DE1127892B (de) | 1960-05-06 | 1960-05-06 | Verfahren zur Herstellung von Thiophosphorsaeureestern |
CH480461A CH414597A (de) | 1960-05-06 | 1961-04-25 | Verfahren zur Herstellung von Thiophosphorsäureestern |
GB1590661A GB969029A (en) | 1960-05-06 | 1961-05-02 | Thiophosphoric acid esters |
FR860613A FR1295613A (fr) | 1960-05-06 | 1961-05-03 | Nouveaux esters thiophosphoriques et leur procédé de préparation |
FR868902A FR1301031A (fr) | 1960-05-06 | 1961-07-25 | Dispositif étanche d'introduction et d'extraction d'éléments dangereux, en particulier d'éléments radioactifs, dans des cellules de traitement |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF31173A DE1127892B (de) | 1960-05-06 | 1960-05-06 | Verfahren zur Herstellung von Thiophosphorsaeureestern |
DEF31899A DE1126382B (de) | 1960-08-17 | 1960-08-17 | Verfahren zur Herstellung von Thiophosphorsaeureestern |
DEF31992A DE1138041B (de) | 1960-08-29 | 1960-08-29 | Verfahren zur Herstellung von Thiophosphorsaeureestern |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1127892B true DE1127892B (de) | 1962-04-19 |
Family
ID=27210174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF31173A Pending DE1127892B (de) | 1960-05-06 | 1960-05-06 | Verfahren zur Herstellung von Thiophosphorsaeureestern |
Country Status (5)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2360548C3 (de) * | 1973-12-05 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | 2-Cyanophenyldithiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1023760B (de) * | 1956-06-29 | 1958-02-06 | Bayer Ag | Verfahren zur Herstellung von Nitroalkylthiophosphorsaeureestern |
DE1032247B (de) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
DE1044826B (de) * | 1956-12-21 | 1958-11-27 | Bayer Ag | Verfahren zur Herstellung von Dialkyl-thio?o-phosphorsaeureestern |
DE1050761B (de) * | 1956-12-21 | 1959-02-19 | Bayer Ag | Verfahren zur Herstellung von Thionophosphorsaeureestern |
DE1078117B (de) * | 1958-10-18 | 1960-03-24 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
-
0
- NL NL264380D patent/NL264380A/xx unknown
- BE BE603613D patent/BE603613A/xx unknown
-
1960
- 1960-05-06 DE DEF31173A patent/DE1127892B/de active Pending
-
1961
- 1961-04-25 CH CH480461A patent/CH414597A/de unknown
- 1961-05-02 GB GB1590661A patent/GB969029A/en not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1032247B (de) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
DE1023760B (de) * | 1956-06-29 | 1958-02-06 | Bayer Ag | Verfahren zur Herstellung von Nitroalkylthiophosphorsaeureestern |
DE1044826B (de) * | 1956-12-21 | 1958-11-27 | Bayer Ag | Verfahren zur Herstellung von Dialkyl-thio?o-phosphorsaeureestern |
DE1050761B (de) * | 1956-12-21 | 1959-02-19 | Bayer Ag | Verfahren zur Herstellung von Thionophosphorsaeureestern |
DE1078117B (de) * | 1958-10-18 | 1960-03-24 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
Also Published As
Publication number | Publication date |
---|---|
BE603613A (US20080094685A1-20080424-C00004.png) | |
NL264380A (US20080094685A1-20080424-C00004.png) | |
GB969029A (en) | 1964-09-09 |
CH414597A (de) | 1966-06-15 |
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