DE1238904B - Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)-saeureestern - Google Patents
Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)-saeureesternInfo
- Publication number
- DE1238904B DE1238904B DE1965F0046711 DEF0046711A DE1238904B DE 1238904 B DE1238904 B DE 1238904B DE 1965F0046711 DE1965F0046711 DE 1965F0046711 DE F0046711 A DEF0046711 A DE F0046711A DE 1238904 B DE1238904 B DE 1238904B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- phosphonic
- thiol
- oxy
- benzene
- 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 24
- 238000000034 method Methods 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000003573 thiols Chemical class 0.000 title description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 47
- 238000003756 stirring Methods 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000005457 ice water Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl radical Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NFIYTPYOYDDLGO-UHFFFAOYSA-N phosphoric acid;sodium Chemical compound [Na].OP(O)(O)=O NFIYTPYOYDDLGO-UHFFFAOYSA-N 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene 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
- C07F9/06—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
-
- 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
- C07F9/28—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)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965F0046711 DE1238904B (de) | 1965-07-24 | 1965-07-24 | Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)-saeureestern |
| CH546666A CH469741A (de) | 1965-07-24 | 1966-04-15 | Verfahren zur Herstellung von phosphorhaltigen Estern |
| IL2560466A IL25604A (en) | 1965-07-24 | 1966-04-19 | Phosphorus-containing esters and process for the preparation thereof |
| GB1791366A GB1081277A (en) | 1965-07-24 | 1966-04-25 | New phosphorus-containing esters and process for the preparation thereof |
| NL6607832A NL6607832A (forum.php) | 1965-07-24 | 1966-06-06 | |
| BE684453D BE684453A (forum.php) | 1965-07-24 | 1966-07-22 | |
| FR70480A FR1491595A (fr) | 1965-07-24 | 1966-07-22 | Procédé de fabrication d'esters d'acides thiol- ou thionothiolphosphoriques |
| ES0329429A ES329429A1 (es) | 1965-07-24 | 1966-07-23 | Procedimiento para la obtencion de esteres del acido tiol y tionotiolfosforico y fosfonico. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965F0046711 DE1238904B (de) | 1965-07-24 | 1965-07-24 | Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)-saeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1238904B true DE1238904B (de) | 1967-04-20 |
Family
ID=7101190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965F0046711 Pending DE1238904B (de) | 1965-07-24 | 1965-07-24 | Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)-saeureestern |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE684453A (forum.php) |
| CH (1) | CH469741A (forum.php) |
| DE (1) | DE1238904B (forum.php) |
| ES (1) | ES329429A1 (forum.php) |
| GB (1) | GB1081277A (forum.php) |
| IL (1) | IL25604A (forum.php) |
| NL (1) | NL6607832A (forum.php) |
-
1965
- 1965-07-24 DE DE1965F0046711 patent/DE1238904B/de active Pending
-
1966
- 1966-04-15 CH CH546666A patent/CH469741A/de unknown
- 1966-04-19 IL IL2560466A patent/IL25604A/en unknown
- 1966-04-25 GB GB1791366A patent/GB1081277A/en not_active Expired
- 1966-06-06 NL NL6607832A patent/NL6607832A/xx unknown
- 1966-07-22 BE BE684453D patent/BE684453A/xx unknown
- 1966-07-23 ES ES0329429A patent/ES329429A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL25604A (en) | 1969-11-30 |
| BE684453A (forum.php) | 1967-01-23 |
| ES329429A1 (es) | 1967-05-16 |
| CH469741A (de) | 1969-03-15 |
| GB1081277A (en) | 1967-08-31 |
| NL6607832A (forum.php) | 1967-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1201839B (de) | Verfahren zur Herstellung aliphatischer Cyansaeureester, die durch elektronen-anziehende Atome oder Gruppen substituiert sind | |
| DE1160440B (de) | Verfahren zur Herstellung von heterocyclischen Phosphor-, Phosphon-, Phosphin- bzw. Thionophosphor-, -phosphon-, -phosphinsaeureestern | |
| DE1238904B (de) | Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)-saeureestern | |
| DE1024509B (de) | Verfahren zur Herstellung von O, O-Dialkyl-thiol-phosphorsaeure- und -thiol-thiono-phsphorsaeureestern | |
| DE1058992B (de) | Verfahren zur Herstellung von Thiophosphonsaeureestern | |
| DE1238013B (de) | Verfahren zur Herstellung von Dithiolphosphorsaeureestern | |
| DE962612C (de) | Verfahren zur Herstellung von therapeutisch wertvollen 1-Phenyl-2, 3-dimethyl-pyrazolon-(5)-4-amido-dialkyl-(diaryl)-phosphinsaeuren bzw. -alkyl-phosphonsaeurealkylestern | |
| DE1141634B (de) | Verfahren zur Herstellung von Dithiolphosphorsaeureestern | |
| DE1942561B2 (de) | Pyrazolo-(thiono)-phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung und diese enthaltende mittel | |
| EP0271695B1 (de) | Verfahren zur Herstellung von Phosphin- oder Phosphonsäurechloriden | |
| DE1198359B (de) | Verfahren zur Herstellung von Thionothiol-phosphor- (-phosphon, -phosphin)-saeureestern | |
| AT233589B (de) | Verfahren zur Herstellung neuer organischer Phosphorverbindungen | |
| DE1192202B (de) | Verfahren zur Herstellung von (Thiono) Phosphor-(on, in)-saeureestern | |
| DE2222578C3 (de) | Verfahren zur Herstellung von O1O-Dialkyl-O-phenylthionophosphorsäureestern | |
| DE2044194C3 (de) | Benzisoxazolo(thiono)phosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| AT235859B (de) | Verfahren zur Herstellung von neuen, beispielsweise zur Schädlingsbekämpfung verwendbaren Phosphonsäureestern | |
| DE1206903B (de) | Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)saeureestern | |
| DE2163063A1 (de) | Dialkylthionophosphorsaeureester | |
| EP0022971A1 (de) | Verfahren zur Herstellung von 3-(2,2-Dichlor-vinyl)-2,2-dimethyl-cyclopropan-1-carbonsäure-derivaten | |
| DE1225168B (de) | Verfahren zur Herstellung von Benzolsulfonsaeurephenylestern | |
| DE1670899C3 (forum.php) | ||
| AT200157B (de) | Verfahren zur Herstellung von neuen Thiophosphorsäureestern | |
| DE1545790C (de) | Pyrazolo-pyrimidin-thionophosphorsäuren und Verfahren zu ihrer Herstellung | |
| DE1176653B (de) | Verfahren zur Herstellung von (Thiono) Phosphon-(-in-)-saeureestern | |
| DE1026323B (de) | Verfahren zur Herstellung von insekticid wirksamen O, O-Dialkyl-S-phenyl-thionothiolphosphorsaeureestern |