GB786763A - Derivatives of thiophosphoric acid - Google Patents
Derivatives of thiophosphoric acidInfo
- Publication number
- GB786763A GB786763A GB863255A GB863255A GB786763A GB 786763 A GB786763 A GB 786763A GB 863255 A GB863255 A GB 863255A GB 863255 A GB863255 A GB 863255A GB 786763 A GB786763 A GB 786763A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzazimide
- alk
- ethyl
- methyl
- compounds
- 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
- 150000003582 thiophosphoric acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- DMSSTTLDFWKBSX-UHFFFAOYSA-N 1h-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N=NNC2=C1 DMSSTTLDFWKBSX-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 241001454295 Tetranychidae Species 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000001055 chewing effect Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000725 suspension Substances 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
- C07F9/65218—Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises as new products O,O - dialkyl - S - (benzazimidomethyl) - thio - phosphates of the formula <FORM:0786763/IV (b)/1> in which X is oxygen or sulphur and "alk" is an alkyl group, e.g. methyl, ethyl, or isopropyl. The compounds may be obtained by reacting N-halogeno-methyl benzazimides with the salts of dialkylthiophosphoric acids or of dialkyldithiophosphoric acids. The reaction is preferably carried out in an inert liquid diluent, e.g. benzene, toluene, or an alcohol or ketone, and is preferably completed at slightly elevated temperature. Examples are given for the production by the above method of compounds of the above formula in which X is a sulphur atom and each "alk" is methyl, ethyl, propyl and isopropyl respectively and compounds in which X is an oxygen atom and each "alk" is ethyl, propyl and isopropyl respectively. The products are stated to be highly effective against sucking and chewing insects, especially spider mites. N-Chloromethyl-benzazimide which is used as starting material in the examples is obtained by treating N-hydroxymethyl benzazimide suspended in chloroform with thionyl chloride and N - bromo - methyl - benzazimide which is also used in one of the examples to prepare the compound in which X is a sulphur atom and each "alk" is ethyl is obtained by adding phosphorus tribromide dropwise to a suspension of N-hydroxymethyl-benzazimide in acetonitrile. N-Hydroxymethylbenzazimide is obtained by reacting benzazimide with formaldehyde and water.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE536870D BE536870A (en) | 1955-03-24 | ||
| US487458A US2758115A (en) | 1955-02-10 | 1955-02-10 | Derivatives of thiophosphoric acid |
| GB863255A GB786763A (en) | 1955-03-24 | 1955-03-24 | Derivatives of thiophosphoric acid |
| CH334531D CH334531A (en) | 1955-03-24 | 1955-04-01 | Process for the preparation of O, O-dialkyl-S- (benzaziminomethyl) -thio- or -dithiophosphates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB863255A GB786763A (en) | 1955-03-24 | 1955-03-24 | Derivatives of thiophosphoric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB786763A true GB786763A (en) | 1957-11-27 |
Family
ID=9856203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB863255A Expired GB786763A (en) | 1955-02-10 | 1955-03-24 | Derivatives of thiophosphoric acid |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE536870A (en) |
| CH (1) | CH334531A (en) |
| GB (1) | GB786763A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1223846B (en) * | 1963-08-12 | 1966-09-01 | Thomae Gmbh Dr K | Process for the preparation of anti-inflammatory 1, 2, 3-benzotriazin-4 (3H) -ones |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228279A (en) | 1979-08-28 | 1980-10-14 | Mobay Chemical Corporation | Production of O,O-dialkyl-S-(benzazimidomethyl)-thiolphosphoric acid esters |
-
0
- BE BE536870D patent/BE536870A/xx unknown
-
1955
- 1955-03-24 GB GB863255A patent/GB786763A/en not_active Expired
- 1955-04-01 CH CH334531D patent/CH334531A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1223846B (en) * | 1963-08-12 | 1966-09-01 | Thomae Gmbh Dr K | Process for the preparation of anti-inflammatory 1, 2, 3-benzotriazin-4 (3H) -ones |
Also Published As
| Publication number | Publication date |
|---|---|
| CH334531A (en) | 1958-12-15 |
| BE536870A (en) |
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