IL41470A - The production of thionophosphoric and thionophosphonic acid esters - Google Patents
The production of thionophosphoric and thionophosphonic acid estersInfo
- Publication number
- IL41470A IL41470A IL41470A IL4147073A IL41470A IL 41470 A IL41470 A IL 41470A IL 41470 A IL41470 A IL 41470A IL 4147073 A IL4147073 A IL 4147073A IL 41470 A IL41470 A IL 41470A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- group
- compound
- lower alkyl
- alkyl group
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 238000005809 transesterification reaction Methods 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- BEWOQXVDCFTBAQ-UHFFFAOYSA-N P(OC1=CC=CC=C1)(OC1=CC=CC=C1)=S Chemical compound P(OC1=CC=CC=C1)(OC1=CC=CC=C1)=S BEWOQXVDCFTBAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- -1 alkali metal cation Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- YDOLGQNXROBHNZ-UHFFFAOYSA-N hydroxy-diphenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=S)(O)OC1=CC=CC=C1 YDOLGQNXROBHNZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 1
- 229940031826 phenolate Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- A01N57/06—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 containing aromatic radicals
-
- 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- 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
- C07F9/4084—Esters with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (27)
1. A process for the preparation of compounds the formula wherein R^ represents a lower alkyl group which may if desired be chlorine- substituted; a phenyl group which if desired be halogen or lower alkyl substituted; a group of formula R-0-, wherein R represents an alkyl group having from 1 to 12 carbon atoms which may if desired, be interrupted by an oxygen atom and/or be substitured - by- a group -of—formula --C00RA_ir(wherein..R. represents a lower alkyl group), or an alkenyl group having from 3 to 12 carbon atoms; represents a lower alkyl group; X and Y which may be the same or different, each represents a hydrogen, chlorine, bromine or iodine atom or a lower alkyl or nitro- group; and Z represents any group which may be represented by X or Y, a cyano or acetyl group, or a group of formula -S(0)nR" (wherein R" represents a lower alkyl group and n is 0, 1 or 2) which process comprises transesterifying a 41470/2 diphenyl thionophosphate or diphenylthionophosphonate of formula (wherein R^ X and Y and Z are as hereinbefore defined) with an alcohol or formula R20H (wherein R2 is as hereinbefore defined) in the presence of a strong base as a catalyst in an amount of about one mole per mole of the compound of formula VI and at a temperature not higher than ambient temperature, to form a compound of formula I.
2. A process as claimed in claim 1 wherein a compound of formula VI is used in which represents a lower alkyl group which may if desired be chlorine substituted, or a phenyl group which may if desired be halogen or lower alkyl substituted.
3. A process as claimed in claim 1 wherein a compound of formula VI is used in which represents a group of formula R-0- wherein R represents an alkyl group having from 1 to 12 carbon atoms which may if desired be interrupted by an oxygen atom and/or be substituted by a group of formula -C00R' (wherein R' represents a lower alkyl group), or an alkenyl group having from 3 to 12 carbon atoms .
4. A process as claimed in claim 2 wherein a compound of formula VI is used in which R, represents a methyl, ethyl, chloromethyl or phenyl group.
5. A process as claimed in claim 3 wherein a compound of formula VI is used in which represents a group of formula R-0- (in which R is an alkyl group containing from 1 to 8 carbon atoms).
6. A process as claimed in claim 5 wherein R is an alkyl group containing from 1 to 4 carbon atoms .
7. A process as claimed in any of the preceding claims wherein a compound of formula R2OH is used in which represents a methyl or ethyl group.
8. A process as claimed in claim 2 wherein a compound of formula R2OH is used in which R2 represents a methyl or ethyl group.
9. A process as claimed in claim 3 wherein a compound of formula ^s use<^ ^n which R2 represents a methyl or ethyl group.
10. A process as claimed in any of the preceding claims in which X, Y and Z occupy between them the 2-, A- and 5- positions of the phenol residue.
11. A process. as claimed in any of the preceding claims in which at least one of X, Y and Z represents a methyl group. 41470/2
12. A process as claimed in claim 2 wherein X, Y and Z are as defined in claim 10 or claim 11.
13. A process as claimed in claim 3 wherein X, Y and Z are as defined in claim 10 or claim 11.
14. A process as claimed in any of the preceding claims wherein the transesterification is effected in the presence of triethylamine as catalyst.
15. A process as claimed in any one of Claims 1 to 13, wherein the transesterification is effected in the presence of an alkali metal alcoholate of the alcohol of formula R20H.
16. A process as claimed in any.one of Claims. l_to 13, wherein the reaction is effected in the presence of an alkali metal hydroxide in water or in the alcohol R20H.
17. A process as claimed in any of the preceding claims in which the reesterification is performed at a^temperaturer-between -ambient- temperature_and_: about -10 °C.
18. A process as claimed in any of the preceding claims wherein the compound of formula VI is first prepared by reacting an acid chloride of formula S CI (wherein is as defined in claim 1) with a phenol or phenolate of formula 41470/2 wherein X, Y and Z are s defined in Claim 1 and represents a hydrogen atom or a monovalent cation.
19. ' A process as claimed in Claim 18, wherein a compound of formula IV is used in which M represents an alkali metal cation.
20. A process as claimed in Claim 18 or Claim 19, wherein a compound of formula IV is used in which is as defined in Claim 2.
21. A process as claimed in Claim 18 or Claim 19, wherein a compound of formula IV is used in which is as defined in Claim 3.
22. A process as claimed in Claim 1 substantially as described herein.
23. A process for the preparation of compounds as claimed in Claim 2 substantially as described in Examples 1 to 4.
24. A process for the preparation of compounds as claimed in Claim 3 substantially as described in Examples 5 and 6.
25. Compounds of formula I as defined in Claim 1, when prepared by a process as claimed in Claim 1.
26. Compounds of formula I as defined in Claim 1, wherein is as defined in Claim 2, when prepared by a process as claimed in Claim 2.
27. Compounds of formula I as defined in Claim 1 wherein 'R^ is as defined in Claim 3, when prepared by a process as claimed in Claim 3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722205565 DE2205565C3 (en) | 1972-02-07 | 1972-02-07 | Process for the preparation of O-alkyl-O-phenyl esters of thionophosphonic acids |
| DE19722222578 DE2222578C3 (en) | 1972-05-09 | 1972-05-09 | Process for the preparation of O1O-dialkyl-O-phenylthionophosphoric acid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41470A0 IL41470A0 (en) | 1973-04-30 |
| IL41470A true IL41470A (en) | 1976-07-30 |
Family
ID=25762679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41470A IL41470A (en) | 1972-02-07 | 1973-02-06 | The production of thionophosphoric and thionophosphonic acid esters |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5652913B2 (en) |
| AT (1) | AT321943B (en) |
| BE (1) | BE795039A (en) |
| CA (1) | CA1011754A (en) |
| CH (1) | CH576990A5 (en) |
| FR (1) | FR2177738B1 (en) |
| GB (1) | GB1400903A (en) |
| IL (1) | IL41470A (en) |
| IT (1) | IT977220B (en) |
| NL (1) | NL7301632A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607176A1 (en) * | 1976-02-21 | 1977-09-01 | Celamerck Gmbh & Co Kg | THIONO or THIONOTHIOL PHOSPHORUS AND THIONOPHOSPHONIC ACID ESTER |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272892A (en) * | 1963-03-04 | 1966-09-13 | Stauffer Chemical Co | Method of preparing organic phosphonates by transesterification |
-
1973
- 1973-01-29 AT AT73573A patent/AT321943B/en not_active IP Right Cessation
- 1973-02-06 BE BE795039D patent/BE795039A/en unknown
- 1973-02-06 JP JP1509373A patent/JPS5652913B2/ja not_active Expired
- 1973-02-06 IL IL41470A patent/IL41470A/en unknown
- 1973-02-06 CH CH165773A patent/CH576990A5/xx not_active IP Right Cessation
- 1973-02-06 IT IT48083/73A patent/IT977220B/en active
- 1973-02-06 NL NL7301632A patent/NL7301632A/xx not_active Application Discontinuation
- 1973-02-06 CA CA163,046A patent/CA1011754A/en not_active Expired
- 1973-02-07 GB GB607073A patent/GB1400903A/en not_active Expired
- 1973-02-07 FR FR7304355A patent/FR2177738B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL41470A0 (en) | 1973-04-30 |
| IT977220B (en) | 1974-09-10 |
| CH576990A5 (en) | 1976-06-30 |
| JPS5652913B2 (en) | 1981-12-15 |
| JPS4911859A (en) | 1974-02-01 |
| CA1011754A (en) | 1977-06-07 |
| NL7301632A (en) | 1973-08-09 |
| FR2177738A1 (en) | 1973-11-09 |
| GB1400903A (en) | 1975-07-16 |
| AT321943B (en) | 1975-04-25 |
| BE795039A (en) | 1973-08-06 |
| FR2177738B1 (en) | 1977-12-30 |
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