GB847550A - Phosphonic acid esters - Google Patents
Phosphonic acid estersInfo
- Publication number
- GB847550A GB847550A GB2008558A GB2008558A GB847550A GB 847550 A GB847550 A GB 847550A GB 2008558 A GB2008558 A GB 2008558A GB 2008558 A GB2008558 A GB 2008558A GB 847550 A GB847550 A GB 847550A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- phenyl
- ester
- sulphur
- reacting
- 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
- 150000003008 phosphonic acid esters Chemical class 0.000 title abstract 2
- -1 e.g. Chemical group 0.000 abstract 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 239000005864 Sulphur Substances 0.000 abstract 4
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 4
- 229920002554 vinyl polymer Chemical group 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000005936 piperidyl group Chemical group 0.000 abstract 2
- UCCIWGKPAPDPCU-UHFFFAOYSA-N 1-diethoxyphosphoryl-2-methylprop-1-ene Chemical compound CCOP(=O)(OCC)C=C(C)C UCCIWGKPAPDPCU-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 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
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 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
- 239000000969 carrier Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- MQRWGDVNDJKTTC-UHFFFAOYSA-M potassium ethoxy-oxido-phenyl-sulfanylidene-lambda5-phosphane Chemical compound [K+].CCOP([O-])(=S)c1ccccc1 MQRWGDVNDJKTTC-UHFFFAOYSA-M 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000005504 styryl group Chemical group 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
- C07F9/4071—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)
- 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 phosphonic acid esters of the general formula: <FORM:0847550/IV(b)/1> wherein R is a cycloalkyl, vinyl substituted by a C1-C6 alkyl radical, phenyl substituted vinyl, or phenyl radical, R is a C1-C6 alkyl radical, R11 and R111 are C1-C6 alkyl radicals or phenyl radicals or may, together with the N atoms, form a heterocyclic ring, e.g., piperidyl or morpholyl, Alk is an alkylene radical and X and Y are sulphur or oxygen atoms at least one of them being a sulphur atom. The compound in which Y is sulphur may be activated by reacting the corresponding phosphonic or thiophosphonic ester chloride (R.P.(X) (OR1)Cl) with an appropriately substituted amino alkyl mercapton of the formula HS. Alk. (N (R11) (R111) preferably in the presence of an acid binding agent, e.g., an alkali metal alcoholate, and of an inert organic solvent. Compounds in which Y is oxygen may be obtained by reacting the above mentioned thiophosphonic acid ester chlorides with the appropriate substituted amino alkyl alcohol, preferably in the presence of an acid binding agent, or by first forming the corresponding substituted amino alkyl alcoholates (e.g. with metallic sodium) and then reacting these with the thiophosphonic acid ester chlorides, preferably in the presence of an inert organic solvent. Compounds in which X is oxygen and Y is sulphur may be prepared by reacting the appropriate thiophosphonic acid alkyl ester chlorides first with 2 molecular proportions of alkali metal hydroxide to form the corresponding thionophosphonic alkyl ester acids of the formula R.P.(S) (OR1) (OH) which react in their tautomeric form RP(O) (OR1) (SH) with appropriately substituted amino alkyl halides in the presence of the excess alkali metal hydroxide to form the products of the formula R P(O) (OR1) (S.Alky .N.R11,R111). Several examples are given examples for specified R- groups in the products being cyclohexyl, phenyl, styryl, isobutenyl and diisobutenyl respectively. The products have insecticidal properties (see Group VI). Isobutenyl phosphonic acid ethyl ester chloride (CH3)2C = CH.P(O) (OC2H5) Cl used as starting material is obtained by heating isobutenyl phosphonic acid diethyl ester to about 60 DEG -65 DEG C., and then reacting with phosgene at 65 DEG to 70 DEG C. Phenyl thionophosphonic acid ethyl ester potassium salt is obtained by dissolving the corresponding ester chloride in acetonitrile, adding water and then an aqueous solution of potassium hydroxide, allowing the temperature to rise to about 70 DEG C. and maintaining it for one hour.ALSO:An insecticidal composition comprises as active ingredient one or more phosphoric acid esters of the general formula: <FORM:0847550/VI/1> wherein R is a cycloalkyl, vinyl substituted by an alkyl radical containing 1 to 6 carbon atoms, phenyl substituted vinyl, or phenyl radical, R1 is an alkyl radical containing 1 to 6 carbon atoms, R11 and R111 are alkyl radicals containing 1 to 6 carbon atoms or phenyl radicals or may, together with the nitrogen atom form a heterocyclic ring e.g., piperidyl or morpholyl, Alk is an alkylene radical and X and Y are sulphur or oxygen atoms, at least one being a sulphur atom (see Group IV(b)) and a solid or liquid diluent or carrier. Specified carriers are talc, chalk, bentonite, clay, water (if necessary with an emulsifier), alcohols, ketones and liquid hydrocarbons. The active ingredient may be used in conjunction with one or more known insecticides and/or fertilizers. Suitable compositions are obtained by mixing the compounds: <FORM:0847550/VI/2> and <FORM:0847550/VI/3> with acetone, adding benzyl hydroxy diphenyl polyglycol ether as emulsifier and then diluting with water.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF23322A DE1058992B (en) | 1957-06-24 | 1957-06-24 | Process for the preparation of thiophosphonic acid esters |
DEF24304A DE1137012B (en) | 1957-06-24 | 1957-11-02 | Process for the production of phosphonic or thionophosphonic acid esters |
Publications (1)
Publication Number | Publication Date |
---|---|
GB847550A true GB847550A (en) | 1960-09-07 |
Family
ID=25974041
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2008558A Expired GB847550A (en) | 1957-06-24 | 1958-06-23 | Phosphonic acid esters |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE568845A (en) |
CH (1) | CH376917A (en) |
DE (2) | DE1058992B (en) |
FR (1) | FR1207524A (en) |
GB (1) | GB847550A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3215721A (en) * | 1959-12-23 | 1965-11-02 | Bayer Ag | 5-alkyl o-aminoalkyl esters of alkyl, aryl, and cyclohexyl dithiophosphonic acids |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE568845A (en) * | 1957-06-24 | |||
NL129033C (en) * | 1959-09-03 | 1900-01-01 | ||
US4012464A (en) * | 1965-09-24 | 1977-03-15 | The United States Of America As Represented By The Secretary Of The Army | S-(2-diisopropylamino-ethyl)O-ethyl methylphosphonothioate stabilized with soluble carbodiimides |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE845801C (en) * | 1949-05-30 | 1952-08-04 | Jan Marcel Didier Aron Samuel | Process for the preparation of orthophosphoric acid monoesters of tertiary amino alcohols |
BE568845A (en) * | 1957-06-24 |
-
0
- BE BE568845D patent/BE568845A/xx unknown
-
1957
- 1957-06-24 DE DEF23322A patent/DE1058992B/en active Pending
- 1957-11-02 DE DEF24304A patent/DE1137012B/en active Pending
-
1958
- 1958-06-10 CH CH6043058A patent/CH376917A/en unknown
- 1958-06-23 GB GB2008558A patent/GB847550A/en not_active Expired
- 1958-06-24 FR FR1207524D patent/FR1207524A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3215721A (en) * | 1959-12-23 | 1965-11-02 | Bayer Ag | 5-alkyl o-aminoalkyl esters of alkyl, aryl, and cyclohexyl dithiophosphonic acids |
Also Published As
Publication number | Publication date |
---|---|
DE1058992B (en) | 1959-06-11 |
DE1137012B (en) | 1962-09-27 |
FR1207524A (en) | 1960-02-17 |
BE568845A (en) | |
CH376917A (en) | 1964-04-30 |
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