GB928611A - Process for the production of thiophosphonic acid esters and ester amides - Google Patents
Process for the production of thiophosphonic acid esters and ester amidesInfo
- Publication number
- GB928611A GB928611A GB790561A GB790561A GB928611A GB 928611 A GB928611 A GB 928611A GB 790561 A GB790561 A GB 790561A GB 790561 A GB790561 A GB 790561A GB 928611 A GB928611 A GB 928611A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thio
- sulphur
- stands
- formula
- 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
- -1 ester amides Chemical class 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- WSFJFIDCQBAQQZ-UHFFFAOYSA-N hydroxy(sulfido)phosphanium Chemical compound S[PH2]=O WSFJFIDCQBAQQZ-UHFFFAOYSA-N 0.000 abstract 3
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Chemical group 0.000 abstract 2
- 239000001301 oxygen Chemical group 0.000 abstract 2
- 125000004437 phosphorous atom Chemical group 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- OXJVPEPMGZHRJB-UHFFFAOYSA-N aminophosphinoamine Chemical compound NPN OXJVPEPMGZHRJB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- ZLRAAUUPULJGTL-UHFFFAOYSA-N diaminophosphinous acid Chemical compound NP(N)O ZLRAAUUPULJGTL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4883—Amides or esteramides thereof, e.g. RP(NR'2)2 or RP(XR')(NR''2) (X = O, S)
-
- 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
-
- 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
- C07F9/4015—Esters of acyclic unsaturated acids
-
- 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)]
- C07F9/44—Amides thereof
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)
Abstract
Compounds of formula <FORM:0928611/IV(a)/1> where R is an aliphatic or aromatic (including araliphatic) radical attached to the phosphorus atom by a direct carbon-phosphorus bond, A stands for <FORM:0928611/IV(a)/2> , R1 and R2 being C1-4 alkyl, or A stands for another -X-R3 group, X is sulphur or oxygen and -X-R3 is the residue of an alcohol, mercaptan, phenol, thiophenol, (thio)phosphoric acid diester, (thio)phosphonic acid monoester or (thio)phosphinic acid, are prepared by reacting a phosphonous acid diamide of formula <FORM:0928611/IV(a)/3> with an alcohol, phenol, mercaptan, thiophenol, (thio)phosphoric acid diester, (thio)phosphonic acid monoester or (thio)phosphinic acid at a temperature between about 50 and 150 DEG C., and subsequently reacting the intermediate so obtained with sulphur. The reaction may be carried out in an inert solvent or in an excess of the second reaction component. The reaction components may contain substituents, specifically halogen, alkoxy, alkylmercapto, nitro, cyano and amino. The products are pesticides (see Group VI). The following are prepared in examples <FORM:0928611/IV(a)/4> iso-C8H15 being <FORM:0928611/IV(a)/5>ALSO:Insecticidal compositions comprise, along with a solid or liquid carrier, an organo-phosphorus compound of formula <FORM:0928611/VI/1> where R is an aliphatic or aromatic (including araliphatic) radical attached to the phosphorus atom by a direct carbon-phosphorus bond, A stands for <FORM:0928611/VI/2> R1 and R2 being C1-4 alkyl, or A stands for another -X-R3 group, X is sulphur or oxygen, and -X-R3 is the residue of an alcohol, mercaptan, phenol, thiophenol, (thio)-phosphoric acid diester, (thio)phosphonic acid monoester, or (thio)phosphinic acid, which has been prepared by reacting a phosphorous acid diamide of formula R-P(NR1R2)2 with R3XH at about 50-150 DEG C. and subsequently reacting with sulphur (see Group IV (b)).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0030691 | 1960-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB928611A true GB928611A (en) | 1963-06-12 |
Family
ID=7093870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB790561A Expired GB928611A (en) | 1960-03-05 | 1961-03-03 | Process for the production of thiophosphonic acid esters and ester amides |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE600875A (en) |
| CH (1) | CH380718A (en) |
| GB (1) | GB928611A (en) |
| NL (1) | NL261975A (en) |
-
0
- NL NL261975D patent/NL261975A/xx unknown
- BE BE600875D patent/BE600875A/xx unknown
-
1961
- 1961-02-27 CH CH233261A patent/CH380718A/en unknown
- 1961-03-03 GB GB790561A patent/GB928611A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH380718A (en) | 1964-08-15 |
| NL261975A (en) | |
| BE600875A (en) |
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