DE1156070B - Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureestern - Google Patents
Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureesternInfo
- Publication number
- DE1156070B DE1156070B DEF35425A DEF0035425A DE1156070B DE 1156070 B DE1156070 B DE 1156070B DE F35425 A DEF35425 A DE F35425A DE F0035425 A DEF0035425 A DE F0035425A DE 1156070 B DE1156070 B DE 1156070B
- Authority
- DE
- Germany
- Prior art keywords
- phosphonic
- cyano
- ethyl
- phosphorus
- acid
- 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
- -1 phosphonic Chemical compound 0.000 title claims description 20
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 14
- 239000011574 phosphorus Substances 0.000 title claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title description 2
- 229910052717 sulfur Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 38
- 239000003921 oil Substances 0.000 description 22
- 125000004093 cyano group Chemical group *C#N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241001454295 Tetranychidae Species 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- HFVYUQVSWQURMK-UHFFFAOYSA-N (3-ethyl-1-sulfanylidenethiophen-2-yl)phosphonic acid Chemical compound C(C)C1=C(S(C=C1)=S)P(O)(=O)O HFVYUQVSWQURMK-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- WXJXBKBJAKPJRN-UHFFFAOYSA-N Methanephosphonothioic acid Chemical compound CP(O)(O)=S WXJXBKBJAKPJRN-UHFFFAOYSA-N 0.000 description 2
- ILRHGKSQOWBYCL-UHFFFAOYSA-N chloro-ethoxy-ethyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)CC ILRHGKSQOWBYCL-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- MYFKLQFBFSHBPA-UHFFFAOYSA-N 1-chloro-2-methylsulfanylethane Chemical compound CSCCCl MYFKLQFBFSHBPA-UHFFFAOYSA-N 0.000 description 1
- SNGPFRROGIZDOS-UHFFFAOYSA-N 2-(2-chloroethylsulfanyl)acetonitrile Chemical compound ClCCSCC#N SNGPFRROGIZDOS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- PYVGYUUJJSINHK-UHFFFAOYSA-N CCOP(C)(O)=O.Cl Chemical compound CCOP(C)(O)=O.Cl PYVGYUUJJSINHK-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 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
- 241001465754 Metazoa Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- UGOLAPHJCTVIEW-UHFFFAOYSA-N chloro-dimethyl-sulfanylidene-$l^{5}-phosphane Chemical compound CP(C)(Cl)=S UGOLAPHJCTVIEW-UHFFFAOYSA-N 0.000 description 1
- NAKDJXIEBCHXIZ-UHFFFAOYSA-N dihydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)C1=CC=CC=C1 NAKDJXIEBCHXIZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WFCLYEAZTHWNEH-UHFFFAOYSA-N ethylthiocyanate Chemical compound CCSC#N WFCLYEAZTHWNEH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DQIMSUZRBYLFOT-UHFFFAOYSA-N hydroxy-dimethyl-sulfanylidene-$l^{5}-phosphane Chemical compound CP(C)(O)=S DQIMSUZRBYLFOT-UHFFFAOYSA-N 0.000 description 1
- WFJZLXLYHXFBMW-UHFFFAOYSA-N hydroxy-dimethyl-sulfanylidene-lambda5-phosphane hydrochloride Chemical compound Cl.CP(C)(O)=S WFJZLXLYHXFBMW-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07F9/30—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
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric 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
- C07F9/1651—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
- C07F9/28—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)
- Life Sciences & Earth Sciences (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL286054D NL286054A (fi) | 1961-11-28 | ||
| BE625408D BE625408A (fi) | 1961-11-28 | ||
| DEF35425A DE1156070B (de) | 1961-11-28 | 1961-11-28 | Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureestern |
| CH1268162A CH422763A (de) | 1961-11-28 | 1962-10-29 | Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsäureestern |
| BR14484962A BR6244849D0 (pt) | 1961-11-28 | 1962-11-22 | Processo para a producao de esteres de acidos fosforicos fosfonicos fosfinicos respectivamente tiofosforicos tiofosfinicos e composicoes praguicidas baseadas nos mesmos |
| GB4499462A GB963624A (en) | 1961-11-28 | 1962-11-28 | Phosphorus-containing esters |
| FR916910A FR1347925A (fr) | 1961-11-28 | 1962-11-28 | Compositions insecticides et acaricides et leur procédé de préparation |
| AT932262A AT239803B (de) | 1961-11-28 | 1962-11-28 | Verfahren zur Herstellung von neuen, beispielsweise zur Schädlingsbekämpfung geeigneten Organophosphorverbindungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35425A DE1156070B (de) | 1961-11-28 | 1961-11-28 | Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1156070B true DE1156070B (de) | 1963-10-24 |
Family
ID=7095995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF35425A Pending DE1156070B (de) | 1961-11-28 | 1961-11-28 | Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureestern |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT239803B (fi) |
| BE (1) | BE625408A (fi) |
| BR (1) | BR6244849D0 (fi) |
| CH (1) | CH422763A (fi) |
| DE (1) | DE1156070B (fi) |
| GB (1) | GB963624A (fi) |
| NL (1) | NL286054A (fi) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1192202B (de) * | 1963-06-24 | 1965-05-06 | Bayer Ag | Verfahren zur Herstellung von (Thiono) Phosphor-(on, in)-saeureestern |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1024509B (de) * | 1956-03-03 | 1958-02-20 | Bayer Ag | Verfahren zur Herstellung von O, O-Dialkyl-thiol-phosphorsaeure- und -thiol-thiono-phsphorsaeureestern |
| DE1036846B (de) * | 1956-12-21 | 1958-08-21 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| DE1047776B (de) * | 1958-03-28 | 1958-12-31 | Bayer Ag | Verfahren zur Herstellung von Thionophosphorsaeureestern |
| DE1062237B (de) * | 1957-01-05 | 1959-07-30 | Bayer Ag | Verfahren zur Herstellung von O, O-Dialkylthiolphosphorsaeure- und -thiolthionophosphorsaeure-S-gamma-cyanallylestern |
| DE1109680B (de) * | 1957-06-24 | 1961-06-29 | Bayer Ag | Verfahren zur Herstellung von Alkylphosphonsaeure-O-alkyl-thiolestern |
-
0
- BE BE625408D patent/BE625408A/xx unknown
- NL NL286054D patent/NL286054A/xx unknown
-
1961
- 1961-11-28 DE DEF35425A patent/DE1156070B/de active Pending
-
1962
- 1962-10-29 CH CH1268162A patent/CH422763A/de unknown
- 1962-11-22 BR BR14484962A patent/BR6244849D0/pt unknown
- 1962-11-28 GB GB4499462A patent/GB963624A/en not_active Expired
- 1962-11-28 AT AT932262A patent/AT239803B/de active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1024509B (de) * | 1956-03-03 | 1958-02-20 | Bayer Ag | Verfahren zur Herstellung von O, O-Dialkyl-thiol-phosphorsaeure- und -thiol-thiono-phsphorsaeureestern |
| DE1036846B (de) * | 1956-12-21 | 1958-08-21 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| DE1062237B (de) * | 1957-01-05 | 1959-07-30 | Bayer Ag | Verfahren zur Herstellung von O, O-Dialkylthiolphosphorsaeure- und -thiolthionophosphorsaeure-S-gamma-cyanallylestern |
| DE1109680B (de) * | 1957-06-24 | 1961-06-29 | Bayer Ag | Verfahren zur Herstellung von Alkylphosphonsaeure-O-alkyl-thiolestern |
| DE1047776B (de) * | 1958-03-28 | 1958-12-31 | Bayer Ag | Verfahren zur Herstellung von Thionophosphorsaeureestern |
Also Published As
| Publication number | Publication date |
|---|---|
| GB963624A (en) | 1964-07-15 |
| NL286054A (fi) | |
| CH422763A (de) | 1966-10-31 |
| AT239803B (de) | 1965-04-26 |
| BE625408A (fi) | |
| BR6244849D0 (pt) | 1973-05-17 |
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