DE1153018B - Verfahren zur Herstellung von Phosphonyl-(thiono)-phosphon-(phosphin)saeureestern - Google Patents
Verfahren zur Herstellung von Phosphonyl-(thiono)-phosphon-(phosphin)saeureesternInfo
- Publication number
- DE1153018B DE1153018B DEF33962A DEF0033962A DE1153018B DE 1153018 B DE1153018 B DE 1153018B DE F33962 A DEF33962 A DE F33962A DE F0033962 A DEF0033962 A DE F0033962A DE 1153018 B DE1153018 B DE 1153018B
- Authority
- DE
- Germany
- Prior art keywords
- ccl
- thiono
- phosphonic
- acid
- phosphonyl
- 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
- 150000002148 esters Chemical class 0.000 title claims description 12
- 239000002253 acid Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 alkyl radicals Chemical class 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 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
- 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
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 5
- 241001124076 Aphididae Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241001454295 Tetranychidae Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229930045534 Me ester-Cyclohexaneundecanoic acid Natural products 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- UTKSCSIZULOYFC-UHFFFAOYSA-N ethoxy(phenyl)phosphinic acid hydrochloride Chemical compound Cl.CCOP(O)(=O)C1=CC=CC=C1 UTKSCSIZULOYFC-UHFFFAOYSA-N 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-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
- SCLFRABIDYGTAZ-UHFFFAOYSA-N methylphosphonic acid dichloride Chemical compound CP(Cl)(Cl)=O SCLFRABIDYGTAZ-UHFFFAOYSA-N 0.000 description 1
- 238000013365 molecular weight analysis method Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL133082D NL133082C (US07608600-20091027-C00054.png) | 1961-05-19 | ||
| NL278522D NL278522A (US07608600-20091027-C00054.png) | 1961-05-19 | ||
| GB936791D GB936791A (US07608600-20091027-C00054.png) | 1961-05-19 | ||
| BE617821D BE617821A (US07608600-20091027-C00054.png) | 1961-05-19 | ||
| DEF33962A DE1153018B (de) | 1961-05-19 | 1961-05-19 | Verfahren zur Herstellung von Phosphonyl-(thiono)-phosphon-(phosphin)saeureestern |
| CH535062A CH422776A (de) | 1961-05-19 | 1962-05-03 | Verfahren zur Herstellung von Phosphonyl-(thiono)phosphon(-in)säureestern |
| US194732A US3211772A (en) | 1961-05-19 | 1962-05-14 | Phosphonyl-(thiono) phosphonic (-phosphinic) acid esters and process for the production thereof |
| BR139110/62A BR6239110D0 (pt) | 1961-05-19 | 1962-05-17 | Processo para a fabricacao de esteres de acido fosfonil (tionos)fosfonico(fosfinico)e composicoes inseticidas baseadas nos mesmos |
| FR898244A FR1334983A (fr) | 1961-05-19 | 1962-05-21 | Esters phosphonyl-(thiono) phosphoniques ou phosphiniques et procédé pour les préparer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF33962A DE1153018B (de) | 1961-05-19 | 1961-05-19 | Verfahren zur Herstellung von Phosphonyl-(thiono)-phosphon-(phosphin)saeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1153018B true DE1153018B (de) | 1963-08-22 |
Family
ID=7095338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF33962A Pending DE1153018B (de) | 1961-05-19 | 1961-05-19 | Verfahren zur Herstellung von Phosphonyl-(thiono)-phosphon-(phosphin)saeureestern |
Country Status (7)
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE823293C (de) * | 1950-02-23 | 1951-12-03 | Farbwerke Hoechst Vormals Meis | Verfahren zur Herstellung organischer, chlorhaltiger Phosphorsaeureabkoemmlinge |
| US2668843A (en) * | 1953-04-21 | 1954-02-09 | Dow Chemical Co | O-(beta, beta, beta-trichlorotertiarybutyl) o-(2, 4, 5-trichlorophenyl) methanephosphonate |
| DE949948C (de) * | 1952-10-11 | 1956-09-27 | Bayer Ag | Verfahren zur Herstellung von halogenierten Phosphorsaeureestern |
| DE1002354B (de) * | 1951-09-25 | 1957-02-14 | Ciba Geigy | Verfahren zur Herstellung von neuen Halogen und Phosphor enthaltenden, organischen Verbindungen |
| US2956920A (en) * | 1958-09-16 | 1960-10-18 | Norddeutsche Affinerie | Dichloro vinyl phosphonic acid esters |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909559A (en) * | 1958-02-03 | 1959-10-20 | Union Carbide Corp | Polymeric phosphate esters and their production |
| US3014954A (en) * | 1959-06-16 | 1961-12-26 | Monsanto Chemicals | Polyphosphorus esters and method of preparing same |
| US3014956A (en) * | 1959-07-21 | 1961-12-26 | Monsanto Chemicals | Pentavalent phosphorus esters |
| US3020306A (en) * | 1959-09-22 | 1962-02-06 | Monsanto Chemicals | Phosphorus compounds |
-
0
- NL NL278522D patent/NL278522A/xx unknown
- GB GB936791D patent/GB936791A/en active Active
- NL NL133082D patent/NL133082C/xx active
- BE BE617821D patent/BE617821A/xx unknown
-
1961
- 1961-05-19 DE DEF33962A patent/DE1153018B/de active Pending
-
1962
- 1962-05-03 CH CH535062A patent/CH422776A/de unknown
- 1962-05-14 US US194732A patent/US3211772A/en not_active Expired - Lifetime
- 1962-05-17 BR BR139110/62A patent/BR6239110D0/pt unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE823293C (de) * | 1950-02-23 | 1951-12-03 | Farbwerke Hoechst Vormals Meis | Verfahren zur Herstellung organischer, chlorhaltiger Phosphorsaeureabkoemmlinge |
| DE1002354B (de) * | 1951-09-25 | 1957-02-14 | Ciba Geigy | Verfahren zur Herstellung von neuen Halogen und Phosphor enthaltenden, organischen Verbindungen |
| DE949948C (de) * | 1952-10-11 | 1956-09-27 | Bayer Ag | Verfahren zur Herstellung von halogenierten Phosphorsaeureestern |
| US2668843A (en) * | 1953-04-21 | 1954-02-09 | Dow Chemical Co | O-(beta, beta, beta-trichlorotertiarybutyl) o-(2, 4, 5-trichlorophenyl) methanephosphonate |
| US2956920A (en) * | 1958-09-16 | 1960-10-18 | Norddeutsche Affinerie | Dichloro vinyl phosphonic acid esters |
Also Published As
| Publication number | Publication date |
|---|---|
| NL278522A (US07608600-20091027-C00054.png) | |
| NL133082C (US07608600-20091027-C00054.png) | |
| US3211772A (en) | 1965-10-12 |
| CH422776A (de) | 1966-10-31 |
| BE617821A (US07608600-20091027-C00054.png) | |
| GB936791A (US07608600-20091027-C00054.png) | |
| BR6239110D0 (pt) | 1973-05-10 |
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