GB1410314A - O-haloalkyl-phosphoric acid esteramides a process for their preparation and their use as insecticides or acaricides - Google Patents
O-haloalkyl-phosphoric acid esteramides a process for their preparation and their use as insecticides or acaricidesInfo
- Publication number
- GB1410314A GB1410314A GB236974A GB236974A GB1410314A GB 1410314 A GB1410314 A GB 1410314A GB 236974 A GB236974 A GB 236974A GB 236974 A GB236974 A GB 236974A GB 1410314 A GB1410314 A GB 1410314A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- ccl
- haloalkyl
- ochbr
- insecticidal
- 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
- 230000000895 acaricidal effect Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000000642 acaricide Substances 0.000 title 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 title 1
- 239000002917 insecticide Substances 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000011230 binding agent Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 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
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
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)
Abstract
1410314 0-haloalkylphosphoric acid ester-amides BAYER AG 18 Jan 1974 [19 Jan 1973] 02369/74 Heading C2P The invention comprises compounds of the general formula wherein R is C 1 -C 12 alkyl, C 1 -C 4 haloalkyl, alkoxy alkyl with up to 6 carbon atoms in the alkyl and alkoxy moieties, C 2 -C 6 alkenyl, or phenyl-alkyl and R and R<SP>1</SP> are H or C 1 -C 8 alkyl or together with the N atom form a 5- or 6-membered heterocyclic ring. They may be obtained either (a) by brominating optionally in the presence of a bromination catalyst, or (b) by reacting an ester dihalide Hal 2 P(O)OCHBr-CCl 2 Br with an alcohol ROH in the form of an alkali metal-, alkaline earth metal- or ammonium-alcoholate, or in the presence of an acid binding agent, to replace one of the Hal atoms by an OR group and then reacting the resulting intermediate, optionally without isolation, with an amine (R<SP>1</SP>)(R<SP>11</SP>)NH in the presence of an acid binding agent. Both methods are preferably effected in an inert organic solvent or diluent and the reaction is preferably effected at 15 to 45 C. The products have insecticidal, especially soil-insecticidal, and acaricidal properties and may be used as active ingredients in conventional pesticidal compositions. The compound Cl 2 P(O)OCHBr.CCl 2 Br is obtained by adding bromine dropwise to a solution of 0-(2,2-dichlorovinyl)-phosphoric acid ester dichloride in CCl 4 at 50 to 55 C. in the presence of a small amount of 1,1<SP>1</SP>-dimethyl-1,1<SP>1</SP>- dicyanoethane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2302569A DE2302569A1 (en) | 1973-01-19 | 1973-01-19 | 0-HALOGENALKYLPHOSPHORIC ACID ESTERAMIDE, METHOD FOR THEIR MANUFACTURE AND USE AS INSECTICIDES AND ACARICIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1410314A true GB1410314A (en) | 1975-10-15 |
Family
ID=5869415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB236974A Expired GB1410314A (en) | 1973-01-19 | 1974-01-18 | O-haloalkyl-phosphoric acid esteramides a process for their preparation and their use as insecticides or acaricides |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3911058A (en) |
| JP (2) | JPS49108022A (en) |
| AT (1) | ATA36574A (en) |
| AU (1) | AU6460874A (en) |
| BE (1) | BE809905A (en) |
| BR (1) | BR7400390D0 (en) |
| DD (1) | DD110750A5 (en) |
| DE (1) | DE2302569A1 (en) |
| DK (1) | DK133338C (en) |
| FR (1) | FR2214697B1 (en) |
| GB (1) | GB1410314A (en) |
| HU (1) | HU167095B (en) |
| IE (1) | IE38766B1 (en) |
| IL (1) | IL44016A (en) |
| LU (1) | LU69189A1 (en) |
| NL (1) | NL7400660A (en) |
| RO (1) | RO63675A (en) |
| TR (1) | TR17602A (en) |
| ZA (1) | ZA74383B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5958905A (en) * | 1996-03-26 | 1999-09-28 | Texas Biotechnology Corporation | Phosphoramidates, phosphinic amides and related compounds and the use thereof to modulate the activity of endothelin |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB784986A (en) * | 1952-10-29 | 1957-10-23 | Fmc Corp | Manufacture of organic phosphorus compounds |
| US3584085A (en) * | 1967-07-18 | 1971-06-08 | Atlas Chem Ind | Phosphoramidates |
-
1973
- 1973-01-18 ZA ZA740383A patent/ZA74383B/en unknown
- 1973-01-19 DE DE2302569A patent/DE2302569A1/en active Pending
-
1974
- 1974-01-07 RO RO7400077212A patent/RO63675A/en unknown
- 1974-01-10 US US432775A patent/US3911058A/en not_active Expired - Lifetime
- 1974-01-16 IL IL44016A patent/IL44016A/en unknown
- 1974-01-17 JP JP49007610A patent/JPS49108022A/ja active Pending
- 1974-01-17 AU AU64608/74A patent/AU6460874A/en not_active Expired
- 1974-01-17 DD DD176066A patent/DD110750A5/xx unknown
- 1974-01-17 AT AT36574*#A patent/ATA36574A/en not_active IP Right Cessation
- 1974-01-17 TR TR17602A patent/TR17602A/en unknown
- 1974-01-17 LU LU69189A patent/LU69189A1/xx unknown
- 1974-01-17 NL NL7400660A patent/NL7400660A/xx unknown
- 1974-01-17 JP JP49007611A patent/JPS49101545A/ja active Pending
- 1974-01-18 BR BR390/74A patent/BR7400390D0/en unknown
- 1974-01-18 DK DK29974*#A patent/DK133338C/en active
- 1974-01-18 FR FR7401748A patent/FR2214697B1/fr not_active Expired
- 1974-01-18 IE IE108/74A patent/IE38766B1/en unknown
- 1974-01-18 BE BE139950A patent/BE809905A/en unknown
- 1974-01-18 GB GB236974A patent/GB1410314A/en not_active Expired
- 1974-01-18 HU HUBA3017A patent/HU167095B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU167095B (en) | 1975-08-28 |
| FR2214697A1 (en) | 1974-08-19 |
| NL7400660A (en) | 1974-07-23 |
| IL44016A (en) | 1977-01-31 |
| DE2302569A1 (en) | 1974-07-25 |
| LU69189A1 (en) | 1974-08-19 |
| JPS49108022A (en) | 1974-10-14 |
| DD110750A5 (en) | 1975-01-12 |
| BE809905A (en) | 1974-07-18 |
| DK133338B (en) | 1976-05-03 |
| AU6460874A (en) | 1975-07-17 |
| RO63675A (en) | 1978-10-15 |
| FR2214697B1 (en) | 1977-08-26 |
| ATA36574A (en) | 1975-07-15 |
| IL44016A0 (en) | 1974-05-16 |
| ZA74383B (en) | 1974-11-27 |
| IE38766B1 (en) | 1978-05-24 |
| JPS49101545A (en) | 1974-09-25 |
| BR7400390D0 (en) | 1974-08-22 |
| US3911058A (en) | 1975-10-07 |
| IE38766L (en) | 1974-07-19 |
| DK133338C (en) | 1976-09-27 |
| TR17602A (en) | 1975-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |