GB783697A - Organic phosphorus compounds - Google Patents
Organic phosphorus compoundsInfo
- Publication number
- GB783697A GB783697A GB29822/53A GB2982253A GB783697A GB 783697 A GB783697 A GB 783697A GB 29822/53 A GB29822/53 A GB 29822/53A GB 2982253 A GB2982253 A GB 2982253A GB 783697 A GB783697 A GB 783697A
- Authority
- GB
- United Kingdom
- Prior art keywords
- halogen
- phosphate
- unsubstituted
- diethyl
- dichlorovinyl
- 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
- 150000002903 organophosphorus compounds Chemical class 0.000 title 1
- -1 cycloalkylene radical Chemical class 0.000 abstract 12
- 125000003118 aryl group Chemical group 0.000 abstract 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 125000004104 aryloxy group Chemical group 0.000 abstract 5
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 3
- YTGSYRVSBPFKMQ-UHFFFAOYSA-N 2,2,2-tribromoacetaldehyde Chemical compound BrC(Br)(Br)C=O YTGSYRVSBPFKMQ-UHFFFAOYSA-N 0.000 abstract 2
- XIVPMNIFAAGBOY-UHFFFAOYSA-N 2,2-dibromoacetaldehyde Chemical compound BrC(Br)C=O XIVPMNIFAAGBOY-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 235000021317 phosphate Nutrition 0.000 abstract 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- YTBDRSHIUAJMQF-UHFFFAOYSA-N (2,2-dichloro-1-diethylphosphorylethenyl) dihydrogen phosphate Chemical compound CCP(=O)(CC)C(=C(Cl)Cl)OP(=O)(O)O YTBDRSHIUAJMQF-UHFFFAOYSA-N 0.000 abstract 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 abstract 1
- VHCWNORMONAZKG-UHFFFAOYSA-N 2-bromo-2,2-dichloroacetaldehyde Chemical compound ClC(Cl)(Br)C=O VHCWNORMONAZKG-UHFFFAOYSA-N 0.000 abstract 1
- GWZQTALMOBAZOL-UHFFFAOYSA-N 2-chloroethyl 2,2-dichloroethenyl methyl phosphate Chemical compound ClCCOP(=O)(OC)OC=C(Cl)Cl GWZQTALMOBAZOL-UHFFFAOYSA-N 0.000 abstract 1
- DAQVNQRAUIJSHT-UHFFFAOYSA-N 2-ethoxy-1,3,2-benzodioxaphosphole Chemical compound C1=CC=C2OP(OCC)OC2=C1 DAQVNQRAUIJSHT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- FBOPSFFWGHLLTB-UHFFFAOYSA-N 2-methoxy-1,3,2-dioxaphospholane Chemical compound COP1OCCO1 FBOPSFFWGHLLTB-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- RHTMZHTWXCIXLL-UHFFFAOYSA-N P(=O)(O)(O)O.ClC(=CC=C)Cl Chemical compound P(=O)(O)(O)O.ClC(=CC=C)Cl RHTMZHTWXCIXLL-UHFFFAOYSA-N 0.000 abstract 1
- MOWNHBRUGRWWNH-UHFFFAOYSA-N P(O)(O)=O.ClC(=CC1=C(C=CC=C1)C)Cl Chemical compound P(O)(O)=O.ClC(=CC1=C(C=CC=C1)C)Cl MOWNHBRUGRWWNH-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 1
- DKMDOBOUUAGJNY-AATRIKPKSA-N [(e)-2-chloroethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C=C\Cl DKMDOBOUUAGJNY-AATRIKPKSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 abstract 1
- LMZLQYYLELWCCW-UHFFFAOYSA-N dimethoxy(phenyl)phosphane Chemical compound COP(OC)C1=CC=CC=C1 LMZLQYYLELWCCW-UHFFFAOYSA-N 0.000 abstract 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl 2,2,2-trichloroacetate Chemical compound CCOC(=O)C(Cl)(Cl)Cl SJMLNDPIJZBEKY-UHFFFAOYSA-N 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 150000002825 nitriles Chemical group 0.000 abstract 1
- IBGCXOFOCKCBNQ-UHFFFAOYSA-N nitro cyanate Chemical compound [O-][N+](=O)OC#N IBGCXOFOCKCBNQ-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003564 thiocarbonyl compounds Chemical class 0.000 abstract 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 abstract 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous 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)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
- C07F9/657118—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s) non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
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
The invention comprises halogen-alkenyl esters of phosphorus of the general formula <FORM:0783697/IV (a)/1> in which Q is oxygen or sulphur, X is a halogen, R1 or R2 are unsubstituted or substituted alkyl, aryl, alkoxy or aryloxy groups, or jointly form an unsubstituted or substituted divalent alkylene dioxy or arylenedioxy radical, R3 and R4 are hydrogen, halogen, or carbalkoxy, or unsubstituted or substituted alkyl, aryl, alkoxy, aryloxy, alkylamino or alkylphosphoryl group or jointly an unsubstituted or substituted divalent alkylene or cycloalkylene radical, especially organic phosphates as above having at least one beta-halogen on the alkenyl radical, monothiophosphates as above having at least one beta-halogen on the alkenyl radical, phosphonates as above having at least one beta-halogen on the alkenyl radical, and phosphinates as above having at least one beta-halogen atom on the alkenyl radical. The above halogenalkenyl esters may be prepared by the reaction between an esterified phosphorus acid of the general formula <FORM:0783697/IV (a)/2> where R is a substituted or unsubstituted alkyl group and R1 and R2 have the above significance, with an alpha-polyhalogenated carbonyl or thiocarbonyl compound of the general formula <FORM:0783697/IV (a)/3> wherein Q, X, R3 and R4 have the above significance. Suitable substituents that R1, R2, R3 and R4 may bear are halogen, cyano, nitro, ether, carbethoxy, and diethylamino substituents. In examples: triethyl phosphite reacts with chloral to give diethyl 2 : 2-dichlorovinyl phosphate, with N : N-diethyl-trichloroacetamide to give diethyl-alpha-diethylamino-beta-beta-dichlorovinyl phosphate, with ethyl trichloroacetate to give diethyl a -ethoxy-beta-beta-dichlorovinyl phosphate, with 2 : 2 : 6-trichlorocyclohexanone, to give diethyl-2,2-dichlorocyclohexenyl - (1) phosphate, and with a polymer of thiochloral to give di-ethyl-S-2 : 2-dichlorovinyl monothiophosphate; chloral reacts with dimethylbenzene-phosphonite to give 2 : 2 - dichlorovinyl - methyl - benzene phosphonate, with ethylene methyl phosphite to give 2 : 2-dichlorovinyl ethylene phosphate and another product 2,2-dichlorovinyl 2-chloroethyl methyl phosphate, and with tris-2-chloroethylphosphite to give bis-2-chloroethyl 2 : 2-dichlorovinyl phosphate; bromal reacts with triethylphosphite to give 2 : 2-dibromovinyl diethyl phosphate; and triethyl phosphite reacts with trichloroacetyl chloride in two steps to form a phosphonate of the formula (C2H5O)2P(O)-C(O)CCl3 which then reacts with triethyl phosphite to form 1 - (diethylphosphoryl) - 2,2 - dichlorovinyl phosphate. In a table a large number of reactants and products obtainable therefrom are listed. Carbonyl reactants referred to in the table are chloral, bromal, dichloro- and dibromo - acetaldehyde, trichloroacetophenone, <FORM:0783697/IV (a)/4> <FORM:0783697/IV (a)/5> <FORM:0783697/IV (a)/6> and <FORM:0783697/IV (a)/7> Esterified phosphorus acids referred to in the table are trialkyl phosphites including those in which the alkyl groups contain alkoxy, nitro, dialkylamino, chloro, heterocyclic, carbalkoxy, acyloxy and nitrile substituents, tricyclohexyl phosphite, diaryl alkyl phosphites including those in which the aryl groups contain hydroxy, chloro and alkyl substituents, aryl dialkyl phosphites including those in which the aryl group contains a nitro substituent, alkylene alkyl phosphites including those in which the alkylene groups contain alkoxy, aryloxy, acyloxy, chloro, carbalkoxy, and alkyl substituents, ethyl o-phenylene phosphite, diethyl phenylphosphinate, diethyl propylphosphinate, and di-(methoxyethoxyethyl) phenylphosphinate.ALSO:Insecticidal, acaricidal, herbicidal and medicinal preparations contain a carrier and as the active ingredient a halogen-alkenyl ester of a pentavelent phosphorus acid having the general formula <FORM:0783697/VI/1> wherein Q represents oxygen or sulphur, X represents a halogen atom, R1 and R2 represent unsubstituted or substituted alkyl, aryl, alkoxy or aryloxy groups or R1 and R2 together form an unsubstituted or substituted divalent alkylenedioxy or arylenedioxy group, and R3 and R4 represent hydrogen or halogen atoms, or carbalkoxy, unsubstituted or substituted alkyl, aryl, alkoxy, aryloxy, alkylamino or alkylphosphoryl groups or R3 and R4 together form an unsubstituted or substituted divalent alkylene or cycloalkylene group. A typical compound of the above general formula is diethyl 2-chlorovinyl phosphate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US783697XA | 1952-10-29 | 1952-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB783697A true GB783697A (en) | 1957-09-25 |
Family
ID=22143613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29822/53A Expired GB783697A (en) | 1952-10-29 | 1953-10-28 | Organic phosphorus compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB783697A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3102842A (en) * | 1962-03-19 | 1963-09-03 | Shell Oil Co | Dialkyl alpha-(trihalophenyl)-beta-(halo)-vinyl phosphates |
| US3183258A (en) * | 1961-11-10 | 1965-05-11 | Sandoz Ag | Dialkyl 1-acylamino 2, 2-dichlorovinyl phosphates |
| US3184377A (en) * | 1961-12-12 | 1965-05-18 | Chemagro Corp | Method of killing nematodes with thiophosphates |
| DE1214681B (en) * | 1963-04-03 | 1966-04-21 | Shell Int Research | Process for the production of phosphonic acid esters |
| US3258507A (en) * | 1961-12-12 | 1966-06-28 | Chemagro Corp | Polychloroethyl dialkyl monothio-phosphates and process of preparing polyhaloethyl and trihalovinyl monothiophosphates |
-
1953
- 1953-10-28 GB GB29822/53A patent/GB783697A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3183258A (en) * | 1961-11-10 | 1965-05-11 | Sandoz Ag | Dialkyl 1-acylamino 2, 2-dichlorovinyl phosphates |
| US3184377A (en) * | 1961-12-12 | 1965-05-18 | Chemagro Corp | Method of killing nematodes with thiophosphates |
| US3258507A (en) * | 1961-12-12 | 1966-06-28 | Chemagro Corp | Polychloroethyl dialkyl monothio-phosphates and process of preparing polyhaloethyl and trihalovinyl monothiophosphates |
| US3102842A (en) * | 1962-03-19 | 1963-09-03 | Shell Oil Co | Dialkyl alpha-(trihalophenyl)-beta-(halo)-vinyl phosphates |
| DE1214681B (en) * | 1963-04-03 | 1966-04-21 | Shell Int Research | Process for the production of phosphonic acid esters |
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