IE40210B1 - Novel o-substituted phenylthionothiolphosphoric acid esters and their use as insecticides and acaricides - Google Patents
Novel o-substituted phenylthionothiolphosphoric acid esters and their use as insecticides and acaricidesInfo
- Publication number
- IE40210B1 IE40210B1 IE2357/74A IE235774A IE40210B1 IE 40210 B1 IE40210 B1 IE 40210B1 IE 2357/74 A IE2357/74 A IE 2357/74A IE 235774 A IE235774 A IE 235774A IE 40210 B1 IE40210 B1 IE 40210B1
- Authority
- IE
- Ireland
- Prior art keywords
- phenol
- solution
- sodium
- mixture
- stirring
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 230000000895 acaricidal effect Effects 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 239000000642 acaricide Substances 0.000 title 1
- 239000002917 insecticide Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- 238000003756 stirring Methods 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- VBBYMPHNERMRES-UHFFFAOYSA-N 2-chloro-4-(chloromethylsulfonyl)phenol Chemical compound OC1=CC=C(S(=O)(=O)CCl)C=C1Cl VBBYMPHNERMRES-UHFFFAOYSA-N 0.000 abstract 1
- VAWDBQGXASBCNW-UHFFFAOYSA-N 4-(chloromethylsulfonyl)phenol Chemical compound OC1=CC=C(S(=O)(=O)CCl)C=C1 VAWDBQGXASBCNW-UHFFFAOYSA-N 0.000 abstract 1
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 abstract 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- -1 O-Substituted phenyl dithiophosphate esters Chemical class 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000011684 sodium molybdate Substances 0.000 abstract 1
- 235000015393 sodium molybdate Nutrition 0.000 abstract 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 abstract 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1460423 O-Substituted phenyl dithiophosphate esters BAYER AG 15 Nov 1974 [17 Nov 1973] 49513/74 Headings C2P and C2C The invention comprises dithiophosphate esters of the formula wherein R<SP>1</SP> is H or halogen (e.g. Cl or Br) and R<SP>2</SP> is alkylsulphonyl, haloalkylsulphonyl, or 1 - fluoro - 1 - carbalkoxy - methylmercapto having 1 to 4 C atoms in the alkyl group. They may be obtained by reacting a substituted phenol: in the presence of an acid binding agent or in the form of an alkali metal-, alkaline earth metal- or ammonium salt, with a halide: (C 2 H 5 O)(nC 3 H 7 S)P(S)Hal, where Hal is halogen, preferably Cl. The products have insecticidal and acaricidal properties and may be used as active ingredients in conventional pesticidal compositions. 4-Chloromethylsulphonyl phenol is obtained by adding sulphuryl chloride dropwise to a mixture of 4-methylmercapto phenol, ethylene chloride, acetic anhydride and a small amount of cone. H 2 SO 4 , stirring the mixture at 40 to 45 C., passing a stream of air through the solution and then adding 50% H 2 O 2 and sodium molybdate at 50 C. with further stirring at 60 to 65 C., the product being isolated after first destroying excess peroxide with sodium bisulphite solution, adding an aqueous solution of NaOH, filtering off the precipitated sodium phenolate and then dissolving the latter in water and acidifying with aqueous HCl. Treatment of the product (dissolved in acetic acid) with chlorine yields 2- chloro-4-chloromethylsulphonyl phenol. The following compounds: can be obtained in an analogous manner to the last-mentioned chlorination method. The compound: is obtained by adding first thiohydroquinone and then fluorochloroacetic acid ethyl ester to a solution of sodium in ethanol at 20 to 25 C., stirring the mixture for 3 days in the same temperature range and then pouring into water.
[GB1460423A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2357526A DE2357526C2 (en) | 1973-11-17 | 1973-11-17 | O-phenylthionothiolphosphoric acid esters, process for their preparation and their use as insecticides and acaricides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE40210L IE40210L (en) | 1975-05-17 |
| IE40210B1 true IE40210B1 (en) | 1979-04-11 |
Family
ID=5898415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2357/74A IE40210B1 (en) | 1973-11-17 | 1974-11-15 | Novel o-substituted phenylthionothiolphosphoric acid esters and their use as insecticides and acaricides |
Country Status (24)
| Country | Link |
|---|---|
| JP (2) | JPS5761037B2 (en) |
| AT (1) | AT327951B (en) |
| BE (1) | BE822178A (en) |
| BR (1) | BR7409531A (en) |
| CA (1) | CA1029386A (en) |
| CH (1) | CH606050A5 (en) |
| CS (1) | CS180030B2 (en) |
| DD (1) | DD118793A5 (en) |
| DE (1) | DE2357526C2 (en) |
| DK (1) | DK137129C (en) |
| EG (1) | EG11540A (en) |
| ES (1) | ES432006A1 (en) |
| FR (1) | FR2251568B1 (en) |
| GB (1) | GB1460423A (en) |
| HU (1) | HU169435B (en) |
| IE (1) | IE40210B1 (en) |
| IL (1) | IL46051A (en) |
| IT (1) | IT1046671B (en) |
| LU (1) | LU71292A1 (en) |
| NL (1) | NL7414950A (en) |
| PL (1) | PL91830B1 (en) |
| SU (1) | SU518108A3 (en) |
| TR (1) | TR17882A (en) |
| ZA (1) | ZA747327B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59147849U (en) * | 1983-03-23 | 1984-10-03 | 平戸金属工業株式会社 | Structure of the cutting blade for reinforcing steel of a wall destruction machine |
| JPS601852U (en) * | 1983-06-18 | 1985-01-09 | 大淀ヂ−ゼル株式会社 | Excavation machine gripping machine |
| HU199234B (en) * | 1987-05-18 | 1990-02-28 | Chinoin Gyogyszer Es Vegyeszet | Microemulsion composition comprising phosphoric acid ester or thiophosphoric acid ester as active ingredient |
| JP6558408B2 (en) | 2016-11-22 | 2019-08-14 | マツダ株式会社 | Control device for compression self-ignition engine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794503A (en) * | 1972-01-26 | 1973-07-25 | Ciba Geigy | DOUBLE ARRIAL THIOPHOSPHATES IN PARTICULAR INSECTIC, ACARICIDE AND FUNGICIDE PROPERTIES |
-
1973
- 1973-11-17 DE DE2357526A patent/DE2357526C2/en not_active Expired
-
1974
- 1974-11-13 BR BR9531/74A patent/BR7409531A/en unknown
- 1974-11-13 EG EG503/74A patent/EG11540A/en active
- 1974-11-13 JP JP49130064A patent/JPS5761037B2/ja not_active Expired
- 1974-11-13 JP JP49130065A patent/JPS5820925B2/en not_active Expired
- 1974-11-14 TR TR17882A patent/TR17882A/en unknown
- 1974-11-14 BE BE150488A patent/BE822178A/en not_active IP Right Cessation
- 1974-11-14 IL IL46051A patent/IL46051A/en unknown
- 1974-11-15 LU LU71292A patent/LU71292A1/xx unknown
- 1974-11-15 ES ES432006A patent/ES432006A1/en not_active Expired
- 1974-11-15 IT IT29496/74A patent/IT1046671B/en active
- 1974-11-15 IE IE2357/74A patent/IE40210B1/en unknown
- 1974-11-15 AT AT916874A patent/AT327951B/en not_active IP Right Cessation
- 1974-11-15 CS CS7400007791A patent/CS180030B2/en unknown
- 1974-11-15 ZA ZA00747327A patent/ZA747327B/en unknown
- 1974-11-15 DD DD182395A patent/DD118793A5/xx unknown
- 1974-11-15 CA CA213,818A patent/CA1029386A/en not_active Expired
- 1974-11-15 GB GB4951374A patent/GB1460423A/en not_active Expired
- 1974-11-15 NL NL7414950A patent/NL7414950A/en not_active Application Discontinuation
- 1974-11-15 FR FR7437745A patent/FR2251568B1/fr not_active Expired
- 1974-11-15 DK DK595574A patent/DK137129C/en active
- 1974-11-15 CH CH1526674A patent/CH606050A5/xx not_active IP Right Cessation
- 1974-11-15 HU HUBA3168A patent/HU169435B/hu unknown
- 1974-11-15 SU SU2075678A patent/SU518108A3/en active
- 1974-11-16 PL PL1974175672A patent/PL91830B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL91830B1 (en) | 1977-03-31 |
| JPS5077541A (en) | 1975-06-24 |
| SU518108A3 (en) | 1976-06-15 |
| DK137129C (en) | 1979-09-03 |
| DK595574A (en) | 1975-07-14 |
| NL7414950A (en) | 1975-05-21 |
| ATA916874A (en) | 1975-05-15 |
| LU71292A1 (en) | 1975-08-20 |
| CA1029386A (en) | 1978-04-11 |
| GB1460423A (en) | 1977-01-06 |
| IL46051A0 (en) | 1975-02-10 |
| TR17882A (en) | 1976-09-01 |
| EG11540A (en) | 1977-09-30 |
| AT327951B (en) | 1976-02-25 |
| DE2357526C2 (en) | 1982-04-22 |
| HU169435B (en) | 1976-11-28 |
| AU7540774A (en) | 1976-05-20 |
| FR2251568A1 (en) | 1975-06-13 |
| DD118793A5 (en) | 1976-03-20 |
| FR2251568B1 (en) | 1978-06-16 |
| IT1046671B (en) | 1980-07-31 |
| BE822178A (en) | 1975-05-14 |
| CS180030B2 (en) | 1977-12-30 |
| DE2357526A1 (en) | 1975-05-28 |
| CH606050A5 (en) | 1978-10-13 |
| JPS5083354A (en) | 1975-07-05 |
| ZA747327B (en) | 1975-11-26 |
| IL46051A (en) | 1978-04-30 |
| BR7409531A (en) | 1976-05-25 |
| IE40210L (en) | 1975-05-17 |
| JPS5820925B2 (en) | 1983-04-26 |
| JPS5761037B2 (en) | 1982-12-22 |
| ES432006A1 (en) | 1976-10-16 |
| DK137129B (en) | 1978-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5690031A (en) | Preparation of aromatic aldehyde | |
| IE40210B1 (en) | Novel o-substituted phenylthionothiolphosphoric acid esters and their use as insecticides and acaricides | |
| GB1399235A (en) | N-sulphenylated n-methylcarbamidoximes process for their preparation and their use as insecticides acaricides or fungicides | |
| GB1350742A (en) | Thiono-phosphoric -phosphonic- acid esters and ester amides a process for their preparation and their use as insecticides and acaricides | |
| GB1420185A (en) | Nitrile-substituted o-ethyl-s-n-propyl-o-vinylthionothiol phosphoric acid esters a process for their preparation and their use as insecticides or acaraicides | |
| GB1340297A (en) | Thionophosphoric phosphinic acid esters and their use as insecitcides and acaricides | |
| GB1275694A (en) | Thiazolo-(thiono)phosphoric(phosphonic)acid esters, process for their preparation, and their use as insecticides, acaricides and fungicides | |
| GB1417372A (en) | Thionophosphoric acid oxime derivatives process for their preparations and their use as insecticides or acaricides | |
| GB1397997A (en) | O-pyrazolo-pyrimidine-thiono-phsophoric -phosphinic- acid esters process for their production and their use as insecticides and acaricides | |
| GB1381088A (en) | Thionophosphoric phosphonic acid oxima derivatives a process for their preparation and their use as insecticides | |
| GB1451291A (en) | Triazolothiazolyl-thiono-phosphoric -phosphonic- acid esters process for their preparation and their use as insecticides and acaricides -including tickicides- | |
| GB1447967A (en) | Quinoxalyl-thiono-thiol-phosphoric-phosphonic acid esters and ester-amides their preparation and their use as insecticides and acaricides | |
| GB1368015A (en) | 1-imidazolyl-methanephosphonic acid esters their production and their medicinal use | |
| GB1512502A (en) | O,o-diethyl-o-(n-methoxy-2-nitrobenzimidoyl)-thiono-phosphoric acid ester process for its preparation and its use as an insecticide and acaricide | |
| NZ196066A (en) | Substituted benzonitriles: virus inhibiting compositions | |
| GB1456088A (en) | Halogen-containing benzisoxazolo-thiono-thiol-prosphoric - phosphonic- acid esters and ester-amides process for their preparation and their use as insecticides and acaraicides | |
| GB1313247A (en) | Thiono- phosphoric -phosphonic- acid esters a process for their preparation and their use as insecticides and acaricides | |
| GB1457395A (en) | O-ethyl-o-n-propyl-o-1-aryl-2-cyano vinyl-thionophosphoric acid esters and their use as insecticides and acaricides | |
| GB1391354A (en) | O-pyrazolopyrimidine-thiono-phosphoric-phosphonic or phosphinic- acid esters or ester-amides process for their production and their use as insecticides or acaricides | |
| IE35198B1 (en) | Cyclopropane carboxylic acid esters and a process for the manufacture thereof | |
| GB1490470A (en) | Sulphonamido-salicylaldehydes | |
| US3262848A (en) | Poultry enterohepatitis treating compositions and methods of using same | |
| GB1410462A (en) | Aminobenzhydroxamic acids and their salts and process for their preparation and their fungicidal and microbicidal use | |
| JPS6229564A (en) | 3-(3-iodopropargyloxy)-propionitrile, manufacture and use | |
| GB1528880A (en) | O-(chloromethylsulphonyl-phenyl)thionophosphonic acid esters and their use as insecticides acaricides and nematicides |