GB631549A - Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal properties - Google Patents
Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal propertiesInfo
- Publication number
- GB631549A GB631549A GB2786947A GB2786947A GB631549A GB 631549 A GB631549 A GB 631549A GB 2786947 A GB2786947 A GB 2786947A GB 2786947 A GB2786947 A GB 2786947A GB 631549 A GB631549 A GB 631549A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- dialkylamino
- hydrochloride
- manufacture
- insecticides
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 title 1
- 230000000749 insecticidal effect Effects 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 abstract 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2433—Compounds containing the structure N-P(=X)n-X-acyl, N-P(=X)n-X-heteroatom, N-P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/245—Compounds containing the structure N-P(=X)n-X-acyl, N-P(=X)n-X-heteroatom, N-P(=X)n-X-CN (X = O, S, Se; n = 0, 1) containing the structure N-P(=X)n-X-P (X = O, S, Se; n = 0, 1)
-
- 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
-
- 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
- C07F9/22—Amides of acids of phosphorus
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
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)
- Crystallography & Structural Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Bis - (bis - dialkylamino) - phosphorous anhydrides, of the general formula <FORM:0631549/IV (b)/1> (wherein R represents alkyl, preferably containing not more than 8 carbon atoms), are manufactured by treating a solution of phosphorus oxychloride in an inert solvent with an anhydrous dialkylamine (preferably in the stoichiometric proportion of 4 mols. to one of POCl3), and treating the resulting bis-(dialkylamino)-chlorophosphine oxide (R2N)2POCl with water (preferably in a slight excess over the stoichiometric proportion of 1 mol. to 2 of the phosphine oxide) and a tertiary base (preferably in an equimolecular proportion to the phosphine oxide). The products, with or without removal of the hydrochloride of the tertiary base, are useful as insecticides. In examples, anhydrous dimethylamine is stirred into a solution of phosphorus oxychloride in benzene at 35-40 DEG C., and the product, after removal of dimethylamine hydrochloride by filtration, is treated with water and pyridine, filtered to remove pyridine hydrochloride and the solvent distilled off under reduced pressure. The benzene may be replaced by other solvents, e.g. carbon tetrachloride.ALSO:As insecticides are employed bis-(bis-dialkylamino)-phosphonous anhydrides, of the general formula <FORM:0631549/VI/1> (wherein R represents an alkyl group, preferably containing not more than 8 carbon atoms), which may be in admixture with pyridine hydrochloride formed as a by-product in their manufacture.
Priority Applications (20)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL63294936A NL142805B (en) | 1947-10-17 | HOLDER FOR SINGLE OR MULTIPLE MAGNETIC HEAD. | |
GB2786947A GB631549A (en) | 1947-10-17 | 1947-10-17 | Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal properties |
BE485264D BE485264A (en) | 1947-10-17 | 1948-10-12 | |
NL142805A NL70079C (en) | 1947-10-17 | 1948-10-15 | |
FR973517D FR973517A (en) | 1947-10-17 | 1948-10-15 | Further development in the manufacture of phosphorus compounds with insecticidal properties |
CH275704D CH275704A (en) | 1947-10-17 | 1948-10-15 | A method of making an insecticidal compound containing phosphorus. |
DEP18511A DE814294C (en) | 1947-10-17 | 1948-10-16 | Process for the preparation of insecticidal phosphorus compounds |
GB3156048A GB652981A (en) | 1947-10-17 | 1948-12-06 | Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal properties |
DE1949P0000307 DE836192C (en) | 1947-10-17 | 1949-11-22 | Process for the preparation of insecticidal phosphorus compounds |
FR59698D FR59698E (en) | 1947-10-17 | 1949-11-24 | Further development in the manufacture of phosphorus compounds with insecticidal properties |
CH287762D CH287762A (en) | 1947-10-17 | 1949-11-24 | A method of making an insecticidal compound containing phosphorus. |
GB3302749A GB690385A (en) | 1947-10-17 | 1949-12-23 | Improvements in or relating to phosphorus-containing organic compounds |
GB3302849A GB690386A (en) | 1947-10-17 | 1949-12-23 | A process for the manufacture of organic phosphorus-containing compounds |
FR62319D FR62319E (en) | 1947-10-17 | 1950-12-19 | Further development in the manufacture of phosphorus compounds with insecticidal properties |
FR62320D FR62320E (en) | 1947-10-17 | 1950-12-20 | Further development in the manufacture of phosphorus compounds with insecticidal properties |
CH292710D CH292710A (en) | 1947-10-17 | 1950-12-20 | Process for the manufacture of O-ethyl-dimethylamino-phosphonic anhydride. |
BE500172D BE500172A (en) | 1947-10-17 | 1950-12-21 | |
DE19500004834 DE889898C (en) | 1947-10-17 | 1950-12-22 | Process for the production of phosphorus compounds |
DE19500004833 DE855567C (en) | 1947-10-17 | 1950-12-22 | Process for the preparation of insecticidal phosphorus compounds |
BE500243D BE500243A (en) | 1947-10-17 | 1950-12-23 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2786947A GB631549A (en) | 1947-10-17 | 1947-10-17 | Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal properties |
Publications (1)
Publication Number | Publication Date |
---|---|
GB631549A true GB631549A (en) | 1949-11-04 |
Family
ID=10261765
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2786947A Expired GB631549A (en) | 1947-10-17 | 1947-10-17 | Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal properties |
GB3156048A Expired GB652981A (en) | 1947-10-17 | 1948-12-06 | Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal properties |
GB3302749A Expired GB690385A (en) | 1947-10-17 | 1949-12-23 | Improvements in or relating to phosphorus-containing organic compounds |
GB3302849A Expired GB690386A (en) | 1947-10-17 | 1949-12-23 | A process for the manufacture of organic phosphorus-containing compounds |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3156048A Expired GB652981A (en) | 1947-10-17 | 1948-12-06 | Improvements in or relating to the manufacture of compounds containing phosphorus having insecticidal properties |
GB3302749A Expired GB690385A (en) | 1947-10-17 | 1949-12-23 | Improvements in or relating to phosphorus-containing organic compounds |
GB3302849A Expired GB690386A (en) | 1947-10-17 | 1949-12-23 | A process for the manufacture of organic phosphorus-containing compounds |
Country Status (6)
Country | Link |
---|---|
BE (3) | BE485264A (en) |
CH (3) | CH275704A (en) |
DE (4) | DE814294C (en) |
FR (4) | FR973517A (en) |
GB (4) | GB631549A (en) |
NL (2) | NL70079C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2671109A (en) * | 1949-11-16 | 1954-03-02 | Pest Control Ltd | Preparation of bis-dialkylamino phosphonous anhydrides |
US2706738A (en) * | 1950-03-23 | 1955-04-19 | Victor Chemical Works | Method of preparing pyrophosphortetraamides of secondary aliphatic and secondary heterocyclic amines in the presence of an inorganic base |
US2745862A (en) * | 1952-06-20 | 1956-05-15 | Allied Chem & Dye Corp | Production of dialkyl hydrogen phosphites |
US2752392A (en) * | 1952-04-11 | 1956-06-26 | Monsanto Chemicals | Manufacture of phosphorus amides |
US2810756A (en) * | 1950-06-26 | 1957-10-22 | Murphy Chemical Ltd | Manufacture of organic phosphorus compound having insecticidal properties |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1026749B (en) * | 1953-04-20 | 1958-03-27 | Dow Chemical Co | Process for the preparation of pyrophosphoric acid alkylamides |
DE1112852B (en) * | 1958-03-18 | 1961-08-17 | Bayer Ag | Pest repellants |
DE1153373B (en) * | 1960-09-17 | 1963-08-29 | Shell Int Research | Process for the production of pyrophosphoric acid esters, phosphoric acid esters, phosphoric amides or carboxylic acid anhydrides |
-
0
- NL NL63294936A patent/NL142805B/en unknown
-
1947
- 1947-10-17 GB GB2786947A patent/GB631549A/en not_active Expired
-
1948
- 1948-10-12 BE BE485264D patent/BE485264A/xx unknown
- 1948-10-15 NL NL142805A patent/NL70079C/xx active
- 1948-10-15 CH CH275704D patent/CH275704A/en unknown
- 1948-10-15 FR FR973517D patent/FR973517A/en not_active Expired
- 1948-10-16 DE DEP18511A patent/DE814294C/en not_active Expired
- 1948-12-06 GB GB3156048A patent/GB652981A/en not_active Expired
-
1949
- 1949-11-22 DE DE1949P0000307 patent/DE836192C/en not_active Expired
- 1949-11-24 CH CH287762D patent/CH287762A/en unknown
- 1949-11-24 FR FR59698D patent/FR59698E/en not_active Expired
- 1949-12-23 GB GB3302749A patent/GB690385A/en not_active Expired
- 1949-12-23 GB GB3302849A patent/GB690386A/en not_active Expired
-
1950
- 1950-12-19 FR FR62319D patent/FR62319E/en not_active Expired
- 1950-12-20 FR FR62320D patent/FR62320E/en not_active Expired
- 1950-12-20 CH CH292710D patent/CH292710A/en unknown
- 1950-12-21 BE BE500172D patent/BE500172A/xx unknown
- 1950-12-22 DE DE19500004833 patent/DE855567C/en not_active Expired
- 1950-12-22 DE DE19500004834 patent/DE889898C/en not_active Expired
- 1950-12-23 BE BE500243D patent/BE500243A/xx unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2671109A (en) * | 1949-11-16 | 1954-03-02 | Pest Control Ltd | Preparation of bis-dialkylamino phosphonous anhydrides |
US2706738A (en) * | 1950-03-23 | 1955-04-19 | Victor Chemical Works | Method of preparing pyrophosphortetraamides of secondary aliphatic and secondary heterocyclic amines in the presence of an inorganic base |
US2810756A (en) * | 1950-06-26 | 1957-10-22 | Murphy Chemical Ltd | Manufacture of organic phosphorus compound having insecticidal properties |
US2752392A (en) * | 1952-04-11 | 1956-06-26 | Monsanto Chemicals | Manufacture of phosphorus amides |
US2745862A (en) * | 1952-06-20 | 1956-05-15 | Allied Chem & Dye Corp | Production of dialkyl hydrogen phosphites |
Also Published As
Publication number | Publication date |
---|---|
FR62319E (en) | 1955-06-13 |
FR59698E (en) | 1954-06-29 |
FR973517A (en) | 1951-02-12 |
GB652981A (en) | 1951-05-02 |
CH292710A (en) | 1953-08-31 |
CH275704A (en) | 1951-06-15 |
BE500243A (en) | 1951-01-15 |
BE485264A (en) | 1948-10-30 |
NL142805B (en) | |
BE500172A (en) | 1951-01-15 |
GB690386A (en) | 1953-04-22 |
GB690385A (en) | 1953-04-22 |
CH287762A (en) | 1952-12-15 |
DE814294C (en) | 1951-09-20 |
DE855567C (en) | 1952-11-13 |
NL70079C (en) | 1950-01-16 |
FR62320E (en) | 1955-06-13 |
DE836192C (en) | 1952-04-10 |
DE889898C (en) | 1953-09-14 |
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