DE957213C - Verfahren zur Herstellung von neuen Thiolthionophosphorsaeureestern - Google Patents
Verfahren zur Herstellung von neuen ThiolthionophosphorsaeureesternInfo
- Publication number
- DE957213C DE957213C DEG17346A DEG0017346A DE957213C DE 957213 C DE957213 C DE 957213C DE G17346 A DEG17346 A DE G17346A DE G0017346 A DEG0017346 A DE G0017346A DE 957213 C DE957213 C DE 957213C
- Authority
- DE
- Germany
- Prior art keywords
- thiolthionophosphoric
- acid
- general formula
- ester
- new
- 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
- 239000002253 acid Substances 0.000 title claims description 23
- 150000002148 esters Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- -1 halomethyl aryl sulfides Chemical class 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- KVLNFTDTHDZRGU-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethylsulfanyl)benzene Chemical compound ClCSC1=CC=C(Cl)C(Cl)=C1 KVLNFTDTHDZRGU-UHFFFAOYSA-N 0.000 description 2
- HNJZDPKMMZXSKT-UHFFFAOYSA-N 3,4-dichlorobenzenethiol Chemical compound SC1=CC=C(Cl)C(Cl)=C1 HNJZDPKMMZXSKT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JPFKCGVGTFHSML-UHFFFAOYSA-N 1,4-dichloro-2-[chloro-[chloro-(2,5-dichlorophenyl)methyl]sulfanylmethyl]benzene Chemical compound ClC1=C(C=C(C=C1)Cl)C(Cl)SC(C1=C(C=CC(=C1)Cl)Cl)Cl JPFKCGVGTFHSML-UHFFFAOYSA-N 0.000 description 1
- XPJUCMIJGVAEGF-UHFFFAOYSA-N 1-chloro-4-(chloromethylsulfanyl)benzene Chemical compound ClCSC1=CC=C(Cl)C=C1 XPJUCMIJGVAEGF-UHFFFAOYSA-N 0.000 description 1
- XYGABWOCCQZPKC-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethylsulfanyl)benzene Chemical compound ClC1=C(C=CC(=C1)Cl)SCCl XYGABWOCCQZPKC-UHFFFAOYSA-N 0.000 description 1
- MTKAJLNGIVXZIS-UHFFFAOYSA-N 3,4-dimethoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1OC MTKAJLNGIVXZIS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UQTQNISIZXSLCI-UHFFFAOYSA-N ClC1=C(C=C(C(=C1)Cl)Cl)SCCl Chemical compound ClC1=C(C=C(C(=C1)Cl)Cl)SCCl UQTQNISIZXSLCI-UHFFFAOYSA-N 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07F9/06—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH772213X | 1954-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE957213C true DE957213C (de) | 1957-01-31 |
Family
ID=4535504
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1048737D Pending DE1048737B (en, 2012) | 1954-06-10 | ||
| DEG17346A Expired DE957213C (de) | 1954-06-10 | 1955-06-09 | Verfahren zur Herstellung von neuen Thiolthionophosphorsaeureestern |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1048737D Pending DE1048737B (en, 2012) | 1954-06-10 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2891984A (en, 2012) |
| BE (1) | BE538871A (en, 2012) |
| CY (1) | CY166A (en, 2012) |
| DE (2) | DE957213C (en, 2012) |
| FR (1) | FR1132520A (en, 2012) |
| GB (1) | GB772213A (en, 2012) |
| MY (1) | MY5800037A (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1063157B (de) * | 1958-10-18 | 1959-08-13 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| DE1072619B (de) * | 1960-01-07 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung von Thiophosphorsäureestern | |
| DE1102150B (de) * | 1959-05-09 | 1961-03-16 | Bayer Ag | Verfahren zur Herstellung von Thiophosphon- oder -phosphinsaeure-estern |
| DE1116659B (de) * | 1958-11-18 | 1961-11-09 | Bayer Ag | Verfahren zur Herstellung von Fluorphenylmercaptomethylthiol- bzw. -dithiophosphon- oder phosphinsaeureestern |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060217A (en) * | 1957-10-25 | 1962-10-23 | Bayer Ag | Thiophosphoric acid esters |
| US2961458A (en) * | 1958-10-17 | 1960-11-22 | Bayer Ag | Phosphorus containing insecticidal compounds and a process for their production |
| DE1071696B (de) * | 1958-10-18 | 1959-12-24 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung von Thiophasphorsäureestern |
| NL256452A (en, 2012) * | 1959-10-02 | |||
| DE1154669B (de) * | 1960-06-10 | 1963-09-19 | Schering Ag | Mittel gegen Spinnmilben |
| NL289742A (en, 2012) * | 1962-03-05 | |||
| US3274299A (en) * | 1963-05-17 | 1966-09-20 | Stauffer Chemical Co | O, o-dialkyl nitrophenoxymethyl-phosphorothioates |
| DE1204667C2 (de) * | 1964-01-04 | 1973-01-25 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen Thionothiolphorsphorsaeureestern |
| US3462530A (en) * | 1964-06-12 | 1969-08-19 | Stauffer Chemical Co | S-chlorophenoxy-methyl,thio,dithio phosphonates or phosphates as insecticides and acaricides |
| IT1168166B (it) * | 1981-09-02 | 1987-05-20 | Montedison Spa | Composizioni acaricide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2266514A (en) * | 1938-09-09 | 1941-12-16 | American Cyanamid Co | Esters of dithiophosphoric acids |
| DE830509C (de) * | 1950-05-24 | 1952-02-04 | Bayer Ag | Verfahren zur Herstellung von neutralen Estern der Thiophosphorsaeure |
| US2609383A (en) * | 1950-09-30 | 1952-09-02 | Lubrizol Corp | Nitrobenzyl thiophosphate esters |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2586655A (en) * | 1948-03-26 | 1952-02-19 | American Cyanamid Co | S-alkoxymethyl-o, o'-dialkyldithiophosphates |
| IT479217A (en, 2012) * | 1949-10-11 | |||
| US2793224A (en) * | 1954-02-03 | 1957-05-21 | Stauffer Chemical Co | P-chlorophenyl-mercaptomethyl di-alkyl dithiophosphates and their use as insecticides |
-
0
- DE DENDAT1048737D patent/DE1048737B/de active Pending
- BE BE538871D patent/BE538871A/xx unknown
-
1955
- 1955-05-13 US US508297A patent/US2891984A/en not_active Expired - Lifetime
- 1955-06-08 GB GB16536/55A patent/GB772213A/en not_active Expired
- 1955-06-09 FR FR1132520D patent/FR1132520A/fr not_active Expired
- 1955-06-09 DE DEG17346A patent/DE957213C/de not_active Expired
-
1957
- 1957-11-21 CY CY16657A patent/CY166A/xx unknown
-
1958
- 1958-12-31 MY MY195837A patent/MY5800037A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2266514A (en) * | 1938-09-09 | 1941-12-16 | American Cyanamid Co | Esters of dithiophosphoric acids |
| DE830509C (de) * | 1950-05-24 | 1952-02-04 | Bayer Ag | Verfahren zur Herstellung von neutralen Estern der Thiophosphorsaeure |
| US2609383A (en) * | 1950-09-30 | 1952-09-02 | Lubrizol Corp | Nitrobenzyl thiophosphate esters |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1072619B (de) * | 1960-01-07 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung von Thiophosphorsäureestern | |
| DE1063157B (de) * | 1958-10-18 | 1959-08-13 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| DE1116659B (de) * | 1958-11-18 | 1961-11-09 | Bayer Ag | Verfahren zur Herstellung von Fluorphenylmercaptomethylthiol- bzw. -dithiophosphon- oder phosphinsaeureestern |
| DE1102150B (de) * | 1959-05-09 | 1961-03-16 | Bayer Ag | Verfahren zur Herstellung von Thiophosphon- oder -phosphinsaeure-estern |
Also Published As
| Publication number | Publication date |
|---|---|
| GB772213A (en) | 1957-04-10 |
| FR1132520A (fr) | 1957-03-12 |
| DE1048737B (en, 2012) | 1959-01-15 |
| MY5800037A (en) | 1958-12-31 |
| BE538871A (en, 2012) | |
| CY166A (en) | 1957-11-21 |
| US2891984A (en) | 1959-06-23 |
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