GB882703A - Phosphonic acid esters - Google Patents
Phosphonic acid estersInfo
- Publication number
- GB882703A GB882703A GB3735/60A GB373560A GB882703A GB 882703 A GB882703 A GB 882703A GB 3735/60 A GB3735/60 A GB 3735/60A GB 373560 A GB373560 A GB 373560A GB 882703 A GB882703 A GB 882703A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vinyl
- acid
- reacting
- appropriate
- cooc2h5
- 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 1
- -1 alkyl radical Chemical group 0.000 abstract 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 150000001502 aryl halides Chemical class 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- MLSZIADXWDYFKM-UHFFFAOYSA-N 1-dichlorophosphorylethene Chemical class ClP(Cl)(=O)C=C MLSZIADXWDYFKM-UHFFFAOYSA-N 0.000 abstract 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 1
- 239000004606 Fillers/Extenders Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 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
- 239000011230 binding agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- QDOPBBLWIUQTAW-UHFFFAOYSA-N dichloro-ethenyl-sulfanylidene-$l^{5}-phosphane Chemical class ClP(Cl)(=S)C=C QDOPBBLWIUQTAW-UHFFFAOYSA-N 0.000 abstract 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F9/28—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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises vinyl phosphonic and -thiophosphonic acid esters of the formula: <FORM:0882703/IV (b)/1> wherein R1 is an alkyl radical containing up to 6 carbon atoms, R2 is a substituted alkyl or unsubstituted or substituted aralkyl or aryl radical and X and Y are oxygen or sulphur. They may be obtained by reacting appropriate vinyl phosphonic- or vinyl thionophosphonic acid alkyl ester chlorides with appropriate alcohols, phenols or mercaptans, or in the case of products in which X is oxygen and Y is sulphur by saponifying vinyl thionophosphonic acid alkyl ester chlorides with an alkali metal hydroxide and then reacting with appropriate substituted alkyl halides or with substituted or unsubstituted aralkyl or aryl halides, or in the case of products in which both X and Y are sulphur by reacting vinyl thionophosphonic acid alkyl ester chlorides with an alkali metal hydrogen sulphide to form an alkali metal salt of the corresponding vinyl thionothiolphosphonic acid alkyl ester and subsequently reacting the latter with appropriate substituted alkyl halides or aryl halides. The group YR2 in the formula may suitably be p-nitrophenoxy or R2 may be one of the following radicals.: <FORM:0882703/IV (b)/2> Several examples are given and the products have insecticidal properties (see Group VI). The vinyl phosphonic acid or vinyl thiophosphonic acid ester chlorides used as starting materials may be obtained by reacting vinyl phosphonic acid dichlorides with about the stoichiometric amount of the appropriate alcohols in the presence of acid binding agents especially tertiary amines or by reacting the corresponding vinyl thiophosphonic acid dichlorides with about stoichiometrical amounts of appropriate alcoholates, especially alkali metal alcoholates and detailed examples are given for the production of CH2=CHP(O)(OC2H5)Cl and the corresponding thiono compounds.ALSO:An insecticidal composition comprises an ester of the general formula CH2:CH.P(X)(OR1)(YR2) wherein R1 is an alkyl radical containing up to 6 carbon atoms, R2 is a substituted alkyl or unsubstituted or substituted aralkyl or aryl radical and X and Y are oxygen or sulphur (see Group IV (b)) together with an inert solid or liquid extender or diluent. Specified diluents are talc, chalk, bentonite, kieselguhr, and water preferably in combination with a suitable emulsifier and/or an organic solubilizer e.g. dimethyl formamide or acetone. The substituent R2 may be -CH2.S.C2H5, -CH2CH2.S.C2H5, -CH2.S.C6H5, -CH2.CH2N(C2H5)2, p-chlorophenylmercaptomethyl (or ethyl), p-chlorobenzyl, -CH2CN, -CH2CH2CN, -CH2-COOC2H5, -CH2CONH2, -CH (COOC2H5).CH2.COOC2H5, -CH(COOC2H5) CO.CH3, or <FORM:0882703/IV/1> Specified active ingredients also include those in which YR2 is p-nitrophenoxy.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF27638A DE1151503B (en) | 1959-02-04 | 1959-02-04 | Process for the production of phosphonic or thio or dithiophosphonic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB882703A true GB882703A (en) | 1961-11-15 |
Family
ID=7092537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3735/60A Expired GB882703A (en) | 1959-02-04 | 1960-02-02 | Phosphonic acid esters |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3029270A (en) |
| BE (1) | BE587271A (en) |
| CH (1) | CH399461A (en) |
| DE (1) | DE1151503B (en) |
| DK (1) | DK107849C (en) |
| GB (1) | GB882703A (en) |
| NL (2) | NL248000A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL261138A (en) * | 1960-02-13 | |||
| US3416912A (en) * | 1966-11-23 | 1968-12-17 | Chemagro Corp | Process of killing plants |
| US3481731A (en) * | 1967-01-27 | 1969-12-02 | Chemagro Corp | Alkoxy vinyl phosphono dithioates as herbicides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2765331A (en) * | 1952-02-29 | 1956-10-02 | Shell Dev | Esters of phosphorus acids and process for the preparation of the same |
| DE1023034B (en) * | 1956-05-24 | 1958-01-23 | Hoechst Ag | Process for the production of vinylphosphonic acid dichloride |
| DE1072245B (en) * | 1957-06-24 | 1959-12-31 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Process for the preparation of phosphonic acid O-alkyl thiol esters |
| NL229481A (en) * | 1957-07-17 |
-
0
- NL NL124866D patent/NL124866C/xx active
- NL NL248000D patent/NL248000A/xx unknown
- BE BE587271D patent/BE587271A/xx unknown
-
1959
- 1959-02-04 DE DEF27638A patent/DE1151503B/en active Pending
-
1960
- 1960-01-27 CH CH94760A patent/CH399461A/en unknown
- 1960-02-01 US US5626A patent/US3029270A/en not_active Expired - Lifetime
- 1960-02-02 GB GB3735/60A patent/GB882703A/en not_active Expired
- 1960-02-03 DK DK41560AA patent/DK107849C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DE1151503B (en) | 1963-07-18 |
| US3029270A (en) | 1962-04-10 |
| NL248000A (en) | 1900-01-01 |
| CH399461A (en) | 1965-09-30 |
| NL124866C (en) | 1900-01-01 |
| BE587271A (en) | 1900-01-01 |
| DK107849C (en) | 1967-07-10 |
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