GB846229A - New esters of o.o-dialkylphosphoric or o.o-dialkylthiono-phosphoric acids and the production of the same - Google Patents
New esters of o.o-dialkylphosphoric or o.o-dialkylthiono-phosphoric acids and the production of the sameInfo
- Publication number
- GB846229A GB846229A GB26/59A GB2659A GB846229A GB 846229 A GB846229 A GB 846229A GB 26/59 A GB26/59 A GB 26/59A GB 2659 A GB2659 A GB 2659A GB 846229 A GB846229 A GB 846229A
- Authority
- GB
- United Kingdom
- Prior art keywords
- production
- compounds
- reaction
- formula
- ch2sc2h5
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 150000002148 esters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 phenoxy, nitrophenoxy Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000005336 allyloxy group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 abstract 1
- DTPNHOJGFWFYOZ-UHFFFAOYSA-N N-cyclooctyl-2-phenoxypyrrolidin-1-amine Chemical compound O(C1=CC=CC=C1)C1N(CCC1)NC1CCCCCCC1 DTPNHOJGFWFYOZ-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- SRXOCFMDUSFFAK-UHFFFAOYSA-N dimethyl peroxide Chemical compound COOC SRXOCFMDUSFFAK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
-
- 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
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
-
- 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
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
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 the general formula:- <FORM:0846229/IV(b)/1> in which R and R1 are C1-C4 alkyl groups, X is an oxygen or sulphur atom and Y is C1-C4 alkoxy, allyloxy, phenoxy, nitrophenoxy, mono-or dialkylamino with 1 to 4 carbon atoms in the alkyl groups, cycloalkylamino, anilino, pyrrolidino, piperidino, C1-C4 alkylmercapto, C1-C4 alkyl sulphonyl, phenylmercapto or phenyl sulphonyl group. They may be obtained by reacting a compound of the formula (RO) (R1O) P(X) Hal in which Hal is a halogen atom, e.g. chlorine, bromine, or iodine, and R, R1 and X are as defined above with a 1-substituted butene-(3)-ol-(2) of the formula HO.CH.(CH2Y).CH =CH2 in which Y is as defined above. The reation may be carried out in the presence of an inert organic diluent, e.g. an aromatic, aliphatic or cycloaliphatic hydrocarbon or an aliphatic chlorohydrocarbon and it is advantageous to effect the reaction in the presence of an agent which binds hydrogen halide, e.g. pyridine, aniline, methylaniline, triethylamine, tripropylamine or other amine whose boiling point is above the reaction temperature or an alkali metal carbonate or bicarbonate. The reaction is preferably effected at about 10 to 130 DEG C. e.g. at 15 to 75 DEG C. Examples are given for the production of compounds in which R and R1 are each ethyl, X is S and Y is -NHC3H7, N(C2H5)2, SC2H5, p.NH.C6H5. p.SO2C6H5, SO2C2H5, phenoxy, cyclooctylamino, pyrrolidine, p.S.C6H5, ethoxy, allyloxy, and p.nitrophenoxy respectively. Examples are also given for the production of (CH3O)2P(S)O.CH(CH2SC2H5) CH=CH2 and the corresponding O,O- diisopropyl and O,O-dibutyl compounds, (CH3O)2 P(O)O CH(CH2.O. C6H5)CH=CH2, (iso C3H7O)2 P(S)OCH (CH2S.C6H5) CH=CH2, and (C2H5O)2 P(O)O CH(CH2SC2H5)CH=CH2. The products have insecticidal properties.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0047332 | 1958-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB846229A true GB846229A (en) | 1960-08-31 |
Family
ID=6968235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26/59A Expired GB846229A (en) | 1958-01-02 | 1959-01-01 | New esters of o.o-dialkylphosphoric or o.o-dialkylthiono-phosphoric acids and the production of the same |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2961457A (en) |
| CH (1) | CH377331A (en) |
| DE (1) | DE1072616B (en) |
| FR (1) | FR1220913A (en) |
| GB (1) | GB846229A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1173723B (en) * | 1960-09-21 | 1964-07-09 | Basf Ag | Preparations for the control of insects |
| US3151147A (en) * | 1961-10-12 | 1964-09-29 | Shell Oil Co | Omicron, omicron-dialkyl omicron-1-sulfonylvinyl and omicron, omicron-dialkyl omicron-1-sulfinylvinyl phosphates |
| US3206493A (en) * | 1961-08-21 | 1965-09-14 | Standard Oil Co | Preparation of o, o, s-triesters of monothiophosphoric acid |
| GB1054093A (en) * | 1963-06-17 | |||
| US3359203A (en) * | 1965-09-01 | 1967-12-19 | Exxon Research Engineering Co | Ashless dithiophosphoric acid derivatives |
| US4493817A (en) * | 1983-07-06 | 1985-01-15 | Teck Corporation | Process for recovering pyrochlore mineral containing niobium and tantalum |
| US6187723B1 (en) * | 1993-09-13 | 2001-02-13 | Exxon Research And Engineering Company | Lubricant composition containing antiwear additive combination |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2394829A (en) * | 1944-04-26 | 1946-02-12 | Shell Dev | Allyl-type phosphates and their preparation |
| US2536647A (en) * | 1948-03-06 | 1951-01-02 | Monsanto Chemicals | Process of preparing bis (beta-chlorethyl)-para-nitrophenyl thiophosphate |
| US2736726A (en) * | 1952-03-28 | 1956-02-28 | Geigy Ag J R | Basic phosphoric acid esters |
| CH318815A (en) * | 1953-04-24 | 1957-01-31 | Ciba Geigy | Process for the production of phosphorus-containing organic compounds |
| GB795340A (en) * | 1953-10-07 | 1958-05-21 | Sandoz Ltd | New insecticidal esters of dithiophosphoric acid |
| NL200075A (en) * | 1954-09-01 | |||
| US2865801A (en) * | 1956-04-06 | 1958-12-23 | Monsanto Chemicals | Propargyl phosphorothioates |
| NL98247C (en) * | 1956-04-27 |
-
0
- DE DENDAT1072616D patent/DE1072616B/en active Pending
-
1958
- 1958-12-22 CH CH6759658A patent/CH377331A/en unknown
- 1958-12-30 US US783671A patent/US2961457A/en not_active Expired - Lifetime
-
1959
- 1959-01-01 GB GB26/59A patent/GB846229A/en not_active Expired
- 1959-01-02 FR FR783188A patent/FR1220913A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1220913A (en) | 1960-05-30 |
| DE1072616B (en) | 1960-01-07 |
| US2961457A (en) | 1960-11-22 |
| CH377331A (en) | 1964-05-15 |
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