GB929216A - Process for the production of thiol-and thionothiol-phosphoric and -phosphinic acid esters - Google Patents
Process for the production of thiol-and thionothiol-phosphoric and -phosphinic acid estersInfo
- Publication number
- GB929216A GB929216A GB851461A GB851461A GB929216A GB 929216 A GB929216 A GB 929216A GB 851461 A GB851461 A GB 851461A GB 851461 A GB851461 A GB 851461A GB 929216 A GB929216 A GB 929216A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- carbon atoms
- alkyl
- radical
- oxygen
- 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.)
- Expired
Links
- -1 aromatic hydrocarbon radical Chemical group 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- 101100212791 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YBL068W-A gene Proteins 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-N carbonotrithioic acid Chemical class SC(S)=S HIZCIEIDIFGZSS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 150000003254 radicals Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters 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
- C07F9/28—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
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have 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
- C07F9/30—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
Abstract
Compounds of the formula RP(X)(R1)(SR2) in which R is an aliphatic or aromatic hydrocarbon radical, R1 is an aliphatic or aromatic hydrocarbon radical or an alkoxy radical, R2 is an alkyl, aralkyl or aryl radical which may be substituted and X is an oxygen or sulphur atom are obtained by reacting phosphorus compounds of the formula R.P(X)(R1)(Hal) wherein R, R1 and X are as defined above and Hal is halogen, e.g. Cl or Br, with salts of trithiocarbonic acid esters of the formula MeS.C(:S)SR2 wherein Me is an alkali metal, alkaline earth metal, ammonium or substituted ammonium ion and R2 is as defined above. The reaction is preferably carried out in an inert solvent or diluent, e.g. a lower aliphatic alcohol or ketone, benzene or toluene or mixture thereof. The reaction is normally carried out at between 20 DEG and 100 DEG C. The invention also comprises compounds of the general formula R1.P(X)(OR11)(SR12) in which R1 is an alkyl or alkenyl radical containing up to 4 carbon atoms, R11 and R12 are alkyl radicals containing up to 4 carbon atoms and X is an oxygen or sulphur atom. Several examples are given and the products have insecticidal properties (see Group VI).ALSO:An insecticidal composition comprises a solid or liquid diluent or carrier and a thiophosphoric ester of the formula R1.P(X)(OR11) (SR21), in which R1 is an alkyl or alkenyl, radical containing up to 4 carbon atoms, R11 and R21 are alkyl radicals containing up to 4 carbon atoms and X is an oxygen or sulphur atom (see Group IV (b)). Specified diluents or carriers are talc, chalk, bentonite, clay, water (if necessary with an emulsifier, e.g. benzyl hydroxy diphenyl polyglycol ether), alcohols, e.g. methanol or ethanol, ketones, e.g. acetone or methyl ethyl ketone, and liquid hydrocarbons. Known insecticides and/or fertilizers may also be present.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30719A DE1136334B (en) | 1960-03-09 | 1960-03-09 | Process for the production of thionothiol or thiolphosphonic and -phosphinic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB929216A true GB929216A (en) | 1963-06-19 |
Family
ID=7093886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB851461A Expired GB929216A (en) | 1960-03-09 | 1961-03-08 | Process for the production of thiol-and thionothiol-phosphoric and -phosphinic acid esters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE600872A (en) |
| CH (1) | CH381220A (en) |
| DE (1) | DE1136334B (en) |
| GB (1) | GB929216A (en) |
| NL (2) | NL136644C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11202008186RA (en) * | 2018-03-07 | 2020-09-29 | Forschungsverbund Berlin Ev | Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE835302C (en) * | 1950-02-23 | 1952-03-31 | Farbwerke Hoechst Vormals Meis | Process for the production of organic compounds containing phosphorus and sulfur |
| DE953795C (en) * | 1955-03-08 | 1956-12-06 | Bayer Ag | Process for the preparation of monothionopyrophoric acid tetraalkyl esters |
-
0
- BE BE600872D patent/BE600872A/xx unknown
- NL NL262130D patent/NL262130A/xx unknown
- NL NL136644D patent/NL136644C/xx active
-
1960
- 1960-03-09 DE DEF30719A patent/DE1136334B/en active Pending
-
1961
- 1961-03-01 CH CH248861A patent/CH381220A/en unknown
- 1961-03-08 GB GB851461A patent/GB929216A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL136644C (en) | |
| NL262130A (en) | |
| DE1136334B (en) | 1962-09-13 |
| CH381220A (en) | 1964-08-31 |
| BE600872A (en) |
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