GB1330788A - Process for preparing unsaturated phosphorous esters - Google Patents
Process for preparing unsaturated phosphorous estersInfo
- Publication number
- GB1330788A GB1330788A GB1330788DA GB1330788A GB 1330788 A GB1330788 A GB 1330788A GB 1330788D A GB1330788D A GB 1330788DA GB 1330788 A GB1330788 A GB 1330788A
- Authority
- GB
- United Kingdom
- Prior art keywords
- halogen
- alkyl
- compounds
- march
- alkali metal
- 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
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- -1 C2P Vinyl phosphorus esters Chemical class 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 229910052727 yttrium Inorganic materials 0.000 abstract 2
- QKCHWPIGTZRBSC-UHFFFAOYSA-N 1,1,2-trichloro-2-dichlorophosphoryloxyethane Chemical compound ClC(Cl)C(Cl)OP(Cl)(Cl)=O QKCHWPIGTZRBSC-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 229940076134 benzene Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- TUNOZJCBRDQKLS-UHFFFAOYSA-N diethyl 1,2,2-trichloroethyl phosphate Chemical compound CCOP(=O)(OCC)OC(Cl)C(Cl)Cl TUNOZJCBRDQKLS-UHFFFAOYSA-N 0.000 abstract 1
- 229960004132 diethyl ether Drugs 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 150000003509 tertiary alcohols Chemical class 0.000 abstract 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-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
- 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
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
-
- 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
- C07F9/16—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
- C07F9/28—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)]
- C07F9/42—Halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1330788 Unsaturated phosphorus esters SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 1 March 1972 [3 March 1971] 5900/71 Heading C2P Vinyl phosphorus esters of the general formula wherein R 1 and R 2 are alkyl or aryl, R 3 , R 4 and R 5 are H, halogen or alkyl, X is O or S, and Y is a covalent bond or an O or S atom are obtained by dehydrohalogenating a phosphorus ester of the formula wherein one of A and B is H and the other is halogen using an alkali metal alkoxide, preferably one derived from a tertiary alcohol having up to 6 carbon atoms, e.g. potassium t-butoxide. The alkoxide suitably dissolved in an excess of the corresponding alkanol may be added slowly to the starting ester which is preferably dissolved in an organic solvent, e.g. benzene, diethylether or dimethylsulphoxide. Alternatively, an alkali metal hydroxide may be added to a solution of the starting ester in the appropriate alcohol. The reaction temperature is suitably maintained at 0-5‹ C. during the addition of the base, e.g. by use of external cooling. Compounds in which R 1 and R 2 are alkyl, R 3 is halogen, R 4 is H, R 5 is H or halogen, X is O or S and Y is an oxygen atom are stated to be novel and the invention includes such compounds per se. The novel compounds have pesticidals, especially insecticidal and acaricidal properties and may be used as active ingredients in pesticidal compositions of conventional type. 1,2,2 - Trichloroethylphosphorodichloridate is obtained by passing gaseous O 2 into a mixture of PCl 3 and trans 1,2-dichloroethylene at -10‹ to - 5‹ C. The product on reacting with ethanol under nitrogen at 0-5‹ C. yields diethyl 1,2,2- trichloroethyl phosphate. When the same product is reacted with P 2 S 5 at 150-170‹ C. under nitrogen followed by reaction with methanol, dimethyl 1,2,2-trichloroethyl phosphorothionate is obtained.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB590071 | 1971-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1330788A true GB1330788A (en) | 1973-09-19 |
Family
ID=9804737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1330788D Expired GB1330788A (en) | 1971-03-03 | 1972-03-01 | Process for preparing unsaturated phosphorous esters |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH537418A (en) |
| DE (1) | DE2209799C3 (en) |
| GB (1) | GB1330788A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4866045A (en) * | 1984-04-30 | 1989-09-12 | E. I. Du Pont Nemours And Company | Tetrachloroethyl phosphorothioate soil insecticide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6121349A (en) | 1984-06-30 | 1986-01-30 | 五十嵐 徹 | Unhulled rice or chaff housing bag |
-
1972
- 1972-03-01 DE DE19722209799 patent/DE2209799C3/en not_active Expired
- 1972-03-01 CH CH297072A patent/CH537418A/en not_active IP Right Cessation
- 1972-03-01 GB GB1330788D patent/GB1330788A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4866045A (en) * | 1984-04-30 | 1989-09-12 | E. I. Du Pont Nemours And Company | Tetrachloroethyl phosphorothioate soil insecticide |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2209799A1 (en) | 1972-09-21 |
| DE2209799B2 (en) | 1980-08-14 |
| CH537418A (en) | 1973-05-31 |
| DE2209799C3 (en) | 1981-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |