GB917085A - Phosphonic and thiophosphonic acid esters - Google Patents
Phosphonic and thiophosphonic acid estersInfo
- Publication number
- GB917085A GB917085A GB4236060A GB4236060A GB917085A GB 917085 A GB917085 A GB 917085A GB 4236060 A GB4236060 A GB 4236060A GB 4236060 A GB4236060 A GB 4236060A GB 917085 A GB917085 A GB 917085A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- c2h5sch2p
- acid
- halogen
- alkylmercaptoalkanephosphonic
- 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
- 239000002253 acid Substances 0.000 title abstract 7
- 150000002148 esters Chemical class 0.000 title abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 12
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 abstract 2
- 229960000956 coumarin Drugs 0.000 abstract 2
- 235000001671 coumarin Nutrition 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- 150000001298 alcohols Chemical class 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
- 239000011230 binding agent Substances 0.000 abstract 1
- -1 chalk Substances 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
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
- 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)
- 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)
Abstract
The invention comprises compounds of formula <FORM:0917085/IV (b)/1> where R and R1 are C1-4 alkyl, R2 is C1-4 alkylor phenyl-mercaptoalkyl, di(C1-4 alkyl(aminoalkyl, C1-4 alkyl- or di(C1-4 alkyl)-aminocarbonyl-C1-4-alkyl, phenyl substituted by halogen and/or nitro and/or C1-4 alkyl and/or C1-4 alkylmercapto, or a coumarin radical which may be substituted by halogen and/or C1-4 alkyl, Alk is C1-4 alkylene and X and Y are oxygen or sulphur. They may be prepared by hydrolysing an alkylmercaptoalkanephosphonic acid ester to the free acid, reacting this with a chlorinating agent, e.g. PCl5 or SOCl2, to the dichloride, reacting this with an alcohol to give the alkylmercaptoalkanephosphonic acid O-alkyl ester monochloride or with P2S5 to give the alkylmercaptoalkanethionophosphonic acid dichloride which is reacted with an alcohol to give the O-alkyl ester monochloride and reacting the alkylmercaptoalkanephosphonic or -thiophosphonic acid ester monochloride with an appropriate OH or SH compound in the presence of an acid binding agent. The products are insecticides (see Group VI). Intermediate compounds prepared in examples according to the above reaction scheme are C2H5SCH2P(O)(OH)2, C2H5SCH2P(O)Cl2, C2H5SCH2P(S)Cl2, C2H5SCH2P(S)(OC2H5)Cl, C2H5SCH2P(S)(OCH3)Cl, C2H5SCH2CH2P(S) (OCH3)Cl and C2H5SCH2P(O) (OC2H5)Cl.ALSO:Insecticidal compositions comprise organo-phosphorus compounds of formula <FORM:0917085/VI/1> where R and R1 are C1-4 alkyl, R2 is C1-4 alkyl- or phenyl-mercaptoalkyl, di(C1-4 alkyl) aminoalkyl, C1-4 alkyl- or di(C1-4 alkyl)-aminocarbonyl-C1-4-alkyl, phenyl substituted by halogen and/or nitro and/or C1-4 alkyl and/or C1-4 alkylmercapto, or a coumarin radical which may be substituted by halogen and/or C1-4 alkyl, Alk is C1-4 alkylene, and X and Y are oxygen or sulphur, together with a solid or liquid carrier e.g. talc, chalk, clay bentonite, alcohols such as methanol, ketones such as acetone or methyl ethyl ketone and liquid hydrocarbons. Known insecticides and/or fertilisers may also be present. Aqueous compositions may contain emulsifiers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4236060A GB917085A (en) | 1960-12-08 | 1960-12-08 | Phosphonic and thiophosphonic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4236060A GB917085A (en) | 1960-12-08 | 1960-12-08 | Phosphonic and thiophosphonic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB917085A true GB917085A (en) | 1963-01-30 |
Family
ID=10424072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4236060A Expired GB917085A (en) | 1960-12-08 | 1960-12-08 | Phosphonic and thiophosphonic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB917085A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019170710A2 (en) | 2018-03-07 | 2019-09-12 | Forschungsverbund Berlin E.V. | Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates |
-
1960
- 1960-12-08 GB GB4236060A patent/GB917085A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019170710A2 (en) | 2018-03-07 | 2019-09-12 | Forschungsverbund Berlin E.V. | Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB928704A (en) | Phosphoric, phosphonic and phosphinic acid esters and the thio analogues thereof | |
| GB806148A (en) | Phosphoric and phosphonic acid derivatives | |
| GB1007755A (en) | New organo-phosphorus esters and pesticidal compositions containing them | |
| GB917085A (en) | Phosphonic and thiophosphonic acid esters | |
| GB823732A (en) | Thiophosphoric acid esters | |
| GB898418A (en) | Thiophosphoric acid esters | |
| GB987378A (en) | Improvements in or relating to cyclic phosphorus-containing esters | |
| GB806638A (en) | Organic derivatives of phosphoric acid | |
| GB804141A (en) | Phosphorus-containing esters containing sulphone groups and a process for their production | |
| GB939946A (en) | Dithiophosphonic acid esters | |
| US3155709A (en) | Method of making hydrocarbylphosphonodithioic acids | |
| GB903795A (en) | Thiophosphonic acid esters | |
| ES444361A1 (en) | O-alkyl-o-(4-alkylpyrimidin(2)yl)-(thiono)-(thiol) phosphoric (phosphonic) acid esters and insecticidal, acaricidal and nematocidal compositions containing them | |
| GB863434A (en) | Phosphonic and thiophosphonic acid esters | |
| GB929099A (en) | Thiolo- and thiolothiono-phosphoric, phosphonic and phosphinic acid esters | |
| GB913229A (en) | Phosphonic thionophosphonic phosphinic and thionophosphinic acid esters of ª-- and ª--naphthols and processes for their production | |
| GB1232564A (en) | ||
| US3082240A (en) | Process for the production of phosphoric acid esters | |
| US3187035A (en) | O-chloroalkyl o-alkylmercaptoalkyl and o-chloroalkyl s-alkylmercaptoalkyl esters of alkyl phosphonic acids | |
| GB841671A (en) | Phosphonic acid esters | |
| GB904401A (en) | Substituted methylamides of o,o-dialkylthio- and o,o-dialkyldithiophosphorylacetic acids | |
| US3527849A (en) | Dithiophosphates and dithiophosphonates having an s-(tert.-butoxy carbonyl methyl) group | |
| US2523146A (en) | Process of preparing disulfide derivatives of thiophosphoric and thiophosphorous acid esters | |
| GB924044A (en) | Thiophosphorus acid esters | |
| GB917438A (en) | Process for the production of monothio- and dithiophosphoric and phosphonic acid esters |