DE1057112B - Verfahren zur Herstellung von Thionophosphonsaeureestern - Google Patents
Verfahren zur Herstellung von ThionophosphonsaeureesternInfo
- Publication number
- DE1057112B DE1057112B DEF23321A DEF0023321A DE1057112B DE 1057112 B DE1057112 B DE 1057112B DE F23321 A DEF23321 A DE F23321A DE F0023321 A DEF0023321 A DE F0023321A DE 1057112 B DE1057112 B DE 1057112B
- Authority
- DE
- Germany
- Prior art keywords
- ecm
- water
- acid
- aphids
- mol
- 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
- 239000002253 acid Substances 0.000 title claims description 11
- 150000002148 esters Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 241001124076 Aphididae Species 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- -1 alkyl radical Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 241001454295 Tetranychidae Species 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 206010058667 Oral toxicity Diseases 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 231100000418 oral toxicity Toxicity 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 3
- 230000009885 systemic effect Effects 0.000 claims 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 2
- 235000011152 sodium sulphate Nutrition 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 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 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- WEQVLSZDHCLFPN-UHFFFAOYSA-N COP(C)(O)=S.Cl Chemical compound COP(C)(O)=S.Cl WEQVLSZDHCLFPN-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- WXJXBKBJAKPJRN-UHFFFAOYSA-N Methanephosphonothioic acid Chemical compound CP(O)(O)=S WXJXBKBJAKPJRN-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- SHHNZMWZZCIDHE-UHFFFAOYSA-N ethoxy-hydroxy-phenyl-sulfanylidene-lambda5-phosphane hydrochloride Chemical compound Cl.CCOP(O)(=S)C1=CC=CC=C1 SHHNZMWZZCIDHE-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- 241000256113 Culicidae Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000239290 Araneae Species 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241001300479 Macroptilium Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001918 phosphonic acid ester group Chemical group 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003512 tertiary amines 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE568698D BE568698A (US07816562-20101019-C00012.png) | 1957-06-24 | ||
| DEF23321A DE1057112B (de) | 1957-06-24 | 1957-06-24 | Verfahren zur Herstellung von Thionophosphonsaeureestern |
| CH6030758A CH376916A (de) | 1957-06-24 | 1958-06-06 | Verfahren zur Herstellung von Thionophosphonsäureestern |
| FR1198265D FR1198265A (fr) | 1957-06-24 | 1958-06-17 | Esters thionophosphoniques et procédé pour leur préparation |
| GB1990258A GB864632A (en) | 1957-06-24 | 1958-06-20 | Thionophosphonic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23321A DE1057112B (de) | 1957-06-24 | 1957-06-24 | Verfahren zur Herstellung von Thionophosphonsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1057112B true DE1057112B (de) | 1959-05-14 |
Family
ID=7090795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF23321A Pending DE1057112B (de) | 1957-06-24 | 1957-06-24 | Verfahren zur Herstellung von Thionophosphonsaeureestern |
Country Status (5)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1146884B (de) * | 1961-02-20 | 1963-04-11 | Bayer Ag | Verfahren zur Herstellung von (Thio)Phosphonsaeureestern |
| US3209019A (en) * | 1959-10-09 | 1965-09-28 | Bayer Ag | Thionophosphonic acid esters and process for their production |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE589122A (US07816562-20101019-C00012.png) * | 1959-03-28 | 1900-01-01 |
-
0
- BE BE568698D patent/BE568698A/xx unknown
-
1957
- 1957-06-24 DE DEF23321A patent/DE1057112B/de active Pending
-
1958
- 1958-06-06 CH CH6030758A patent/CH376916A/de unknown
- 1958-06-17 FR FR1198265D patent/FR1198265A/fr not_active Expired
- 1958-06-20 GB GB1990258A patent/GB864632A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3209019A (en) * | 1959-10-09 | 1965-09-28 | Bayer Ag | Thionophosphonic acid esters and process for their production |
| DE1146884B (de) * | 1961-02-20 | 1963-04-11 | Bayer Ag | Verfahren zur Herstellung von (Thio)Phosphonsaeureestern |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1198265A (fr) | 1959-12-07 |
| GB864632A (en) | 1961-04-06 |
| BE568698A (US07816562-20101019-C00012.png) | |
| CH376916A (de) | 1964-04-30 |
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