DE1171427B - Verfahren zur Herstellung von Thiophosphor-, -phosphon- oder -phosphinsaeureestern bzw. -esteramiden - Google Patents
Verfahren zur Herstellung von Thiophosphor-, -phosphon- oder -phosphinsaeureestern bzw. -esteramidenInfo
- Publication number
- DE1171427B DE1171427B DEF36913A DEF0036913A DE1171427B DE 1171427 B DE1171427 B DE 1171427B DE F36913 A DEF36913 A DE F36913A DE F0036913 A DEF0036913 A DE F0036913A DE 1171427 B DE1171427 B DE 1171427B
- Authority
- DE
- Germany
- Prior art keywords
- minutes
- acid esters
- reaction
- acid
- ccl
- 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.)
- Granted
Links
- -1 ester amides Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title description 3
- 150000002148 esters Chemical class 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000255925 Diptera Species 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- SWYHWRRXAKMZLK-UHFFFAOYSA-N chloromethyl thiohypochlorite Chemical class ClCSCl SWYHWRRXAKMZLK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- QLQIPARPOAWVAC-UHFFFAOYSA-N (3-methylthiophen-2-yl)phosphonic acid Chemical compound CC=1C=CSC=1P(O)(O)=O QLQIPARPOAWVAC-UHFFFAOYSA-N 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
- 241000131102 Oryzaephilus Species 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JZVMQGJXQXMDHF-UHFFFAOYSA-N dibutoxy(methyl)phosphane Chemical compound CCCCOP(C)OCCCC JZVMQGJXQXMDHF-UHFFFAOYSA-N 0.000 description 1
- PVGXPSIJXXNWSR-UHFFFAOYSA-N difluoromethyl thiohypochlorite Chemical compound FC(F)SCl PVGXPSIJXXNWSR-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- UHRWQVZMGFDNCG-UHFFFAOYSA-N n-diethoxyphosphanyl-n-ethylethanamine Chemical compound CCOP(OCC)N(CC)CC UHRWQVZMGFDNCG-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- LDNCAOOMUMJYTN-UHFFFAOYSA-N phenyl-di(propan-2-yloxy)phosphane Chemical compound CC(C)OP(OC(C)C)C1=CC=CC=C1 LDNCAOOMUMJYTN-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 239000002023 wood Substances 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)]
- C07F9/44—Amides thereof
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl 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
- C07F9/28—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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
-
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE632757D BE632757A (US07217764-20070515-C00014.png) | 1962-05-26 | ||
| DEF36913A DE1171427B (de) | 1962-05-26 | 1962-05-26 | Verfahren zur Herstellung von Thiophosphor-, -phosphon- oder -phosphinsaeureestern bzw. -esteramiden |
| US282215A US3270095A (en) | 1962-05-26 | 1963-05-22 | Fluoro-chloro substituted phosphorus containing esters |
| GB20839/63A GB1012002A (en) | 1962-05-26 | 1963-05-24 | Phosphorus-containing esters |
| FR935996A FR1357398A (fr) | 1962-05-26 | 1963-05-25 | Compositions insecticides utilisables en agriculture et leur procédé de fabrication |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF36913A DE1171427B (de) | 1962-05-26 | 1962-05-26 | Verfahren zur Herstellung von Thiophosphor-, -phosphon- oder -phosphinsaeureestern bzw. -esteramiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1171427B true DE1171427B (de) | 1964-06-04 |
| DE1171427C2 DE1171427C2 (US07217764-20070515-C00014.png) | 1964-12-23 |
Family
ID=7096665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF36913A Granted DE1171427B (de) | 1962-05-26 | 1962-05-26 | Verfahren zur Herstellung von Thiophosphor-, -phosphon- oder -phosphinsaeureestern bzw. -esteramiden |
Country Status (5)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3391230A (en) * | 1964-10-07 | 1968-07-02 | Stauffer Chemical Co | Omicron, omicron-diethyl-s-trichloromethyl-phosphorodithioated |
| US3439092A (en) * | 1964-10-07 | 1969-04-15 | Stauffer Chemical Co | Control of fungi with o,o-diethyl-s-trichloromethylphosphorodithioate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2861092A (en) * | 1956-08-22 | 1958-11-18 | Eastman Kodak Co | S-trichloromethyl tetraalkylphosphorodiamidothiolates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2818364A (en) * | 1953-10-26 | 1957-12-31 | Monsanto Chemicals | Alkyl phosphite esters of perchloromethyl mercaptan and insecticidal compositions comprising the same |
| US2811543A (en) * | 1955-08-31 | 1957-10-29 | Eastman Kodak Co | Phosphorothiolates having insecticidal properties, and method of making same |
| US2931755A (en) * | 1958-04-11 | 1960-04-05 | Monsanto Chemicals | Omicron, omicron-dialkyl or omicron, omicron-bis (haloalkyl) s-dichloromethyl phosphorothioates |
-
0
- BE BE632757D patent/BE632757A/xx unknown
-
1962
- 1962-05-26 DE DEF36913A patent/DE1171427B/de active Granted
-
1963
- 1963-05-22 US US282215A patent/US3270095A/en not_active Expired - Lifetime
- 1963-05-24 GB GB20839/63A patent/GB1012002A/en not_active Expired
- 1963-05-25 FR FR935996A patent/FR1357398A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2861092A (en) * | 1956-08-22 | 1958-11-18 | Eastman Kodak Co | S-trichloromethyl tetraalkylphosphorodiamidothiolates |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1012002A (en) | 1965-12-01 |
| BE632757A (US07217764-20070515-C00014.png) | |
| US3270095A (en) | 1966-08-30 |
| DE1171427C2 (US07217764-20070515-C00014.png) | 1964-12-23 |
| FR1357398A (fr) | 1964-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1067016B (de) | Verfahren zur Her stellung von organischen Phosphorver bmdungen | |
| US3076009A (en) | Thiophosphoric acid esters and production | |
| DE1171427B (de) | Verfahren zur Herstellung von Thiophosphor-, -phosphon- oder -phosphinsaeureestern bzw. -esteramiden | |
| DE1138049B (de) | Verfahren zur Herstellung von Dithiophosphonsaeureestern | |
| DE1153747B (de) | Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureestern | |
| DE1183494B (de) | Verfahren zur Herstellung von Phosphor-, Phosphon- bzw. Thionophosphor-, -phosphonsaeureestern | |
| DE1206425B (de) | Verfahren zur Herstellung von Phosphorsaeureestern | |
| DE1140776B (de) | Schaedlingsbekaempfungsmittel | |
| DE1251745B (US07217764-20070515-C00014.png) | ||
| DE2743848A1 (de) | Verfahren und zusammensetzung fuer die bekaempfung von insekten und akariden | |
| DE1232151B (de) | Verfahren zur Herstellung von phosphorhaltigen Thiazolderivaten | |
| DE1153746B (de) | Verfahren zur Herstellung von Thiophosphor-(-phosphon, -phosphin)- bzw. Dithiophosphor-(-phosphon, -phosphin)-saeureestern | |
| DE1192202B (de) | Verfahren zur Herstellung von (Thiono) Phosphor-(on, in)-saeureestern | |
| DE1263748B (de) | Verfahren zur Herstellung von 2, 2-Dichlor-vinyl-phosphorsaeureestern | |
| DE1233852B (de) | Verfahren zur Herstellung von Phosphorverbindungen | |
| DE1210833B (de) | Verfahren zur Herstellung von Phosphonsaeuredialkylestern | |
| DE1193036B (de) | Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureestern | |
| DE1046062B (de) | Verfahren zur Herstellung von insecticid wirksamen Dialkyl-thionothiolphosphorsaeureestern | |
| DE1059444B (de) | Verfahren zur Herstellung von Thionophosphorsaeureestern | |
| DE1204667C2 (de) | Verfahren zur Herstellung von unsymmetrischen Thionothiolphorsphorsaeureestern | |
| AT253526B (de) | Verfahren zur Herstellung neuer Phosphorsäureester | |
| DE1198359B (de) | Verfahren zur Herstellung von Thionothiol-phosphor- (-phosphon, -phosphin)-saeureestern | |
| DE1238014B (de) | Verfahren zur Herstellung von Phosphorsaeureestern | |
| DE1917741B2 (de) | (thiono)phosphor(phosphon) -saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung | |
| DE1141277B (de) | Verfahren zur Herstellung von Phosphorsaeureestern |
