GB1081277A - New phosphorus-containing esters and process for the preparation thereof - Google Patents
New phosphorus-containing esters and process for the preparation thereofInfo
- Publication number
- GB1081277A GB1081277A GB1791366A GB1791366A GB1081277A GB 1081277 A GB1081277 A GB 1081277A GB 1791366 A GB1791366 A GB 1791366A GB 1791366 A GB1791366 A GB 1791366A GB 1081277 A GB1081277 A GB 1081277A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- alkyl
- prepared
- formula
- thioether
- 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
- 150000002148 esters Chemical class 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 230000000895 acaricidal effect Effects 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 abstract 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N dimethyl monosulfide Natural products CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 150000003568 thioethers Chemical class 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Novel esters of the formula <FORM:1081277/C2/1> where R is C1- 6 alkyl or cycloalkyl, R1 is alkyl and R2 is alkoxy, are prepared by reacting a -acyloxy - a 1 - halo - dimethyl thioethers of the general formula R-C(O)-O-CH2-S-CH2-Hal where Hal is a halogen atom, with a salt of the formula Me-S-P(S)(OR1)(R2), where Me is a monovalent metal equivalent or an ammonium group, or with the corresponding free acids in the presence of acid-binding agents. The reaction is preferably carried out in the presence of inert organic solvents or diluents, and at a temperature between 40 DEG and 100 DEG C. Suitable acid-binding agents include alkali metal carbonates and alcoholates and tertiary amines. The compounds have insecticidal and acaricidal properties. a - Acetyloxy-dimethyl thioether is prepared by reacting acetyl chloride with dimethyl sulphoxide in the presence of triethylamine. a -Hexahydro - benzoyloxy - dimethyl thioether is prepared analogously using hexahydrobenzoyl chloride. a - Acetyloxy - a 1 - chloro - dimethyl - thioether and a - propionyloxy - a 1 - chloro - dimethyl thioether are prepared by reacting the corresponding a 1-unsubstituted thioethers with sulphuryl chloride in methylene chloride.ALSO:Insecticidal and acaricidal compositions comprise a compound of the formula <FORM:1081277/A5-A6/1> where R is C1-6 alkyl or is cycloalkyl, R1 is alkyl and R2 is alkoxy, in admixture with a solid or liquid diluent or carrier. The compositions may be formulated as solutions, emulsifiable concentrates, emulsions, suspensions, spray powders, pastes, soluble powders, dusts and granules, and may be applied by watering, spraying, vaporising, atomising, fumigating, scattering or dusting.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965F0046711 DE1238904B (en) | 1965-07-24 | 1965-07-24 | Process for the production of thiol or thionothiolphosphorus (- phosphonic) acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1081277A true GB1081277A (en) | 1967-08-31 |
Family
ID=7101190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1791366A Expired GB1081277A (en) | 1965-07-24 | 1966-04-25 | New phosphorus-containing esters and process for the preparation thereof |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE684453A (en) |
| CH (1) | CH469741A (en) |
| DE (1) | DE1238904B (en) |
| ES (1) | ES329429A1 (en) |
| GB (1) | GB1081277A (en) |
| IL (1) | IL25604A (en) |
| NL (1) | NL6607832A (en) |
-
1965
- 1965-07-24 DE DE1965F0046711 patent/DE1238904B/en active Pending
-
1966
- 1966-04-15 CH CH546666A patent/CH469741A/en unknown
- 1966-04-19 IL IL2560466A patent/IL25604A/en unknown
- 1966-04-25 GB GB1791366A patent/GB1081277A/en not_active Expired
- 1966-06-06 NL NL6607832A patent/NL6607832A/xx unknown
- 1966-07-22 BE BE684453D patent/BE684453A/xx unknown
- 1966-07-23 ES ES0329429A patent/ES329429A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL25604A (en) | 1969-11-30 |
| BE684453A (en) | 1967-01-23 |
| DE1238904B (en) | 1967-04-20 |
| ES329429A1 (en) | 1967-05-16 |
| NL6607832A (en) | 1967-01-25 |
| CH469741A (en) | 1969-03-15 |
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