GB1511413A - Phosphoryloxy-thiophene compounds processes for preparing them and pesticidal compositions incorporating them - Google Patents
Phosphoryloxy-thiophene compounds processes for preparing them and pesticidal compositions incorporating themInfo
- Publication number
- GB1511413A GB1511413A GB5698/76A GB569876A GB1511413A GB 1511413 A GB1511413 A GB 1511413A GB 5698/76 A GB5698/76 A GB 5698/76A GB 569876 A GB569876 A GB 569876A GB 1511413 A GB1511413 A GB 1511413A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- reacting
- novel
- stated
- 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
- -1 Phosphoryloxy-thiophene compounds Chemical class 0.000 title abstract 4
- 239000000203 mixture Substances 0.000 title abstract 2
- 230000000361 pesticidal effect Effects 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- HQHGJRRZSVKWLE-UHFFFAOYSA-N 3-hydroxy-5-propylthiophene-2-carbonitrile Chemical compound CCCC1=CC(O)=C(C#N)S1 HQHGJRRZSVKWLE-UHFFFAOYSA-N 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 1
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 abstract 1
- MTFXCXOWMORKIM-UHFFFAOYSA-N ethyl 3-sulfanylidenehexanoate Chemical compound CCCC(=S)CC(=O)OCC MTFXCXOWMORKIM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 125000006606 n-butoxy group Chemical group 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 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
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1511413 Phosphorus esters containing a substituted thiophene group ROUSSEL-UCLAF 13 Feb 1976 [14 Feb 1975] 05698/76 Headings C2P and C2C The invention comprises compounds (I) of the formula wherein R 1 is C 1 -C 4 alkyl, R 2 is C 1- C 4 alkyl or -alkoxy, or a radical -NR<SP>1</SP>R<SP>11</SP> wherein R<SP>1</SP> and R<SP>11</SP> are H or C 1 -C 4 alkyl, R 3 is CN, -COOC 1 -C 4 alkyl, or -COZ where Z is C 1 -C 4 alkyl or phenyl, R 4 is C 1 -C 6 alkyl, -alkoxy or -alkythio, phenyl, N-morpholinyl, N-piperidinyl or -COOC 1 -C 4 alkyl, and X is O or S. They may be obtained by reacting in compound (II) with ClP(X)(OR 1 )R 2 preferably in the presence of a basic agent. The compounds (I) have insecticidal, acaricidal and nematocidal properties and may be used as active ingredients in conventional pesticidal compositions. Compounds (II) of the above formula in which R 3 is cyano and R 4 is methoxy, N- morpholino, ethylthio, n-butoxy and n-propyl respectively are stated to be novel and are obtained by reacting a compound (IV) of the formula wherein R 4 <SP>1</SP> corresponds to the specified R 4 group and alk is an alkyl radical with chloroacetonitrile. The compounds (IV) in which R 4 <SP>1</SP> is methoxy and n-butoxy respectively are also stated to be novel and are prepared by reacting 0-methyl- or 0-n-butyl-2-ethoxycarbonyl imidoacetate hydrochloride respectively with H 2 S. Examples are given for the production of the said novel compounds II and IV. The imidoacetate hydrochlorides are also stated to be novel and are prepared in examples by reacting ethyl cyanacetate with methanol or n-butanol respectively in the presence of HCl gas. Ethyl 3-thioxohexanoate is obtained by bubbling H 2 S into ethyl 3-oxo-hexanoate in ethanol saturated with HCl gas at - 10 C. and is converted to 2 - cyano - 3 - hydroxy - 5 - propylthiophene by reaction with chloroacetonitrile as above.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7504628A FR2300768A1 (en) | 1975-02-14 | 1975-02-14 | NEW THIOPENIC PHOSPHORY COMPOUNDS, PROCESS FOR PREPARATION AND APPLICATION AS PESTICIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1511413A true GB1511413A (en) | 1978-05-17 |
Family
ID=9151233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5698/76A Expired GB1511413A (en) | 1975-02-14 | 1976-02-13 | Phosphoryloxy-thiophene compounds processes for preparing them and pesticidal compositions incorporating them |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS51105053A (en) |
| BE (1) | BE838487A (en) |
| BG (1) | BG25196A3 (en) |
| BR (1) | BR7600876A (en) |
| CA (1) | CA1074795A (en) |
| CH (1) | CH610331A5 (en) |
| DD (1) | DD125575A5 (en) |
| DE (1) | DE2605649A1 (en) |
| DK (1) | DK58376A (en) |
| EG (1) | EG12442A (en) |
| ES (1) | ES444618A1 (en) |
| FR (1) | FR2300768A1 (en) |
| GB (1) | GB1511413A (en) |
| GR (1) | GR59269B (en) |
| HU (1) | HU176606B (en) |
| IL (1) | IL48857A (en) |
| IT (1) | IT1053490B (en) |
| NL (1) | NL7601489A (en) |
| OA (1) | OA05248A (en) |
| PH (1) | PH15203A (en) |
| PL (1) | PL98486B1 (en) |
| PT (1) | PT64795B (en) |
| SU (1) | SU644360A3 (en) |
| TR (1) | TR19251A (en) |
| ZA (1) | ZA76709B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093384A1 (en) * | 1982-04-30 | 1983-11-09 | Ube Industries, Ltd. | Thiophene derivatives and fungicidal composition containing the same |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2831936A1 (en) * | 1978-07-20 | 1980-02-07 | Basf Ag | THIENYL METHYL PHOSPHORIC ACID ESTER |
| JPS6058918B2 (en) * | 1980-01-22 | 1985-12-23 | 宇部興産株式会社 | Thiophene derivatives and agricultural and horticultural fungicides |
| WO2010101967A2 (en) * | 2009-03-04 | 2010-09-10 | Idenix Pharmaceuticals, Inc. | Phosphothiophene and phosphothiazole hcv polymerase inhibitors |
-
1975
- 1975-02-14 FR FR7504628A patent/FR2300768A1/en active Granted
-
1976
- 1976-01-16 IL IL48857A patent/IL48857A/en unknown
- 1976-01-26 ES ES444618A patent/ES444618A1/en not_active Expired
- 1976-01-28 BG BG7600032211A patent/BG25196A3/en unknown
- 1976-02-05 CA CA245,098A patent/CA1074795A/en not_active Expired
- 1976-02-06 ZA ZA760709A patent/ZA76709B/en unknown
- 1976-02-09 PH PH18068A patent/PH15203A/en unknown
- 1976-02-10 SU SU762318651A patent/SU644360A3/en active
- 1976-02-10 EG EG66/76A patent/EG12442A/en active
- 1976-02-12 BE BE164261A patent/BE838487A/en unknown
- 1976-02-12 DD DD191215A patent/DD125575A5/xx unknown
- 1976-02-12 DE DE19762605649 patent/DE2605649A1/en not_active Withdrawn
- 1976-02-12 BR BR7600876A patent/BR7600876A/en unknown
- 1976-02-13 CH CH181076A patent/CH610331A5/en not_active IP Right Cessation
- 1976-02-13 PT PT64795A patent/PT64795B/en unknown
- 1976-02-13 IT IT48103/76A patent/IT1053490B/en active
- 1976-02-13 DK DK58376*#A patent/DK58376A/en unknown
- 1976-02-13 TR TR19251A patent/TR19251A/en unknown
- 1976-02-13 NL NL7601489A patent/NL7601489A/en not_active Application Discontinuation
- 1976-02-13 JP JP51014121A patent/JPS51105053A/ja active Pending
- 1976-02-13 PL PL1976187218A patent/PL98486B1/en unknown
- 1976-02-13 GB GB5698/76A patent/GB1511413A/en not_active Expired
- 1976-02-13 GR GR50050A patent/GR59269B/en unknown
- 1976-02-13 HU HU76RO878A patent/HU176606B/en unknown
- 1976-02-14 OA OA55742A patent/OA05248A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093384A1 (en) * | 1982-04-30 | 1983-11-09 | Ube Industries, Ltd. | Thiophene derivatives and fungicidal composition containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7601489A (en) | 1976-08-17 |
| FR2300768A1 (en) | 1976-09-10 |
| GR59269B (en) | 1977-12-05 |
| DK58376A (en) | 1976-08-15 |
| JPS51105053A (en) | 1976-09-17 |
| DE2605649A1 (en) | 1976-08-26 |
| PT64795B (en) | 1978-02-06 |
| CH610331A5 (en) | 1979-04-12 |
| EG12442A (en) | 1981-03-31 |
| BE838487A (en) | 1976-08-12 |
| BR7600876A (en) | 1976-09-14 |
| HU176606B (en) | 1981-03-28 |
| IL48857A0 (en) | 1976-03-31 |
| IL48857A (en) | 1978-06-15 |
| IT1053490B (en) | 1981-08-31 |
| TR19251A (en) | 1978-08-15 |
| ZA76709B (en) | 1977-03-30 |
| SU644360A3 (en) | 1979-01-25 |
| OA05248A (en) | 1981-02-28 |
| PH15203A (en) | 1982-09-17 |
| DD125575A5 (en) | 1977-05-04 |
| CA1074795A (en) | 1980-04-01 |
| FR2300768B1 (en) | 1977-07-22 |
| BG25196A3 (en) | 1978-08-10 |
| ES444618A1 (en) | 1977-10-01 |
| AU1110476A (en) | 1977-08-18 |
| PT64795A (en) | 1976-03-01 |
| PL98486B1 (en) | 1978-05-31 |
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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 |