GB1016666A - Thionothiolphosphonic acid esters - Google Patents
Thionothiolphosphonic acid estersInfo
- Publication number
- GB1016666A GB1016666A GB3552264A GB3552264A GB1016666A GB 1016666 A GB1016666 A GB 1016666A GB 3552264 A GB3552264 A GB 3552264A GB 3552264 A GB3552264 A GB 3552264A GB 1016666 A GB1016666 A GB 1016666A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- carbon atoms
- aryl
- radical containing
- general formula
- 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
- 239000002253 acid Substances 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 aryl mercapto Chemical class 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 150000001340 alkali metals Chemical class 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 241000238876 Acari Species 0.000 abstract 1
- 241001124076 Aphididae Species 0.000 abstract 1
- 241000256113 Culicidae Species 0.000 abstract 1
- 241000255925 Diptera Species 0.000 abstract 1
- 241001325166 Phacelia congesta Species 0.000 abstract 1
- 241001454295 Tetranychidae Species 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003008 phosphonic acid esters Chemical class 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- 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)
Abstract
The invention comprises thionothiolphosphonic acid esters of the general formula <FORM:1016666/C2/1> wherein R1 is an alkyl radical containing up to 4 carbon atoms or a phenyl radical, R11 is an alkyl radical containing up to 4 carbon atoms, R111 is an alkyl, aryl or haloaryl radical and X is a hydrogen atom or an alkyl radical containing up to 4 carbon atoms. They may be prepared by reacting an alkali metal or ammonium salt of an alkyl or aryl-O-alkyl thionothiol phosphonic acid ester with (A) an a -monohaloalkane carboxylic acid-N-(alkylmercapto- or aryl mercapto)-methylamide or (B) first with an a -monohalo-alkane carboxylic acid-N-(hydroxymethyl) amide to give a compound of the Formula II:- <FORM:1016666/C2/2> which is then reacted with an alkyl or aryl mercaptan of the general formula R111SH or (c) first with an a -monohalo-carboxylic acid amide to give a compound of the general Formula III:- <FORM:1016666/C2/3> which is then reacted with formaldehyde to give a compound of the general Formula II which is then reacted with an alkyl or aryl mercaptan R111SH. The reactions may be carried out in the presence of acid binding agents such as alkali metal alcoholates or carbonates in which case the free acids corresponding to the alkali metal or ammonium salts of the esters may be used. Inert organic solvents or diluents such as aliphatic ketones and nitriles may also be present. The thionothiolphosphonic acid esters of the invention are useful as insecticides (see Division A5).ALSO:A pesticidal composition comprises compounds of the general formula: <FORM:1016666/A5-A6/1> wherein R1 is an alkyl radical containing up to 4 carbon atoms or a phenyl radical, R11 is an alkyl radical containing up to 4 carbon atoms, R111 is an alkyl, aryl or haloaryl radical, and X is a hydrogen atom or an alkyl radical containing up to 4 carbon atoms and a solid or liquid diluent or carrier. Suitable solid carriers are talc, chalk and clay and as liquid diluents water (if necessary with commercial emulsifiers), alcohols and liquid hydrocarbons may be used. A preferred composition contains a compound of the invention admixed with dimethyl formamide as auxiliary solvent, a commercial benzyl hydroxy diphenyl polyglycol ether emulsifier, this premixture being diluted with water. The compounds may also be used in combination with other known insecticides and/or fertilisers. An example describes the use of the preferred composition against aphids, spider mites, caterpillars, larvae of flies, mosquito larvae and ticks.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF40648A DE1192647B (en) | 1963-08-31 | 1963-08-31 | Process for the production of thiol or thionothiolphosphonic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1016666A true GB1016666A (en) | 1966-01-12 |
Family
ID=7098332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3552264A Expired GB1016666A (en) | 1963-08-31 | 1964-08-31 | Thionothiolphosphonic acid esters |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE652476A (en) |
| DE (1) | DE1192647B (en) |
| GB (1) | GB1016666A (en) |
| NL (1) | NL6410020A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4016266A (en) * | 1975-06-02 | 1977-04-05 | Stauffer Chemical Company | N-Alkylthiomethylacetamidephosphorodithioate insecticides |
| US4283395A (en) * | 1980-03-24 | 1981-08-11 | Stauffer Chemical Company | S-Alkyl and alkenyl-thiophenylacetamido thiophosphates and phosphonates and method of controlling insects |
| US4356022A (en) * | 1980-03-24 | 1982-10-26 | Stauffer Chemical Company | S-Alkyl and alkenyl-thiophenylacetamido thiophosphates and phosphonates as plant growth regulants |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL266412A (en) * | 1960-06-30 | 1900-01-01 |
-
1963
- 1963-08-31 DE DEF40648A patent/DE1192647B/en active Pending
-
1964
- 1964-08-28 NL NL6410020A patent/NL6410020A/xx unknown
- 1964-08-31 GB GB3552264A patent/GB1016666A/en not_active Expired
- 1964-08-31 BE BE652476D patent/BE652476A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4016266A (en) * | 1975-06-02 | 1977-04-05 | Stauffer Chemical Company | N-Alkylthiomethylacetamidephosphorodithioate insecticides |
| US4283395A (en) * | 1980-03-24 | 1981-08-11 | Stauffer Chemical Company | S-Alkyl and alkenyl-thiophenylacetamido thiophosphates and phosphonates and method of controlling insects |
| US4356022A (en) * | 1980-03-24 | 1982-10-26 | Stauffer Chemical Company | S-Alkyl and alkenyl-thiophenylacetamido thiophosphates and phosphonates as plant growth regulants |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1192647B (en) | 1965-05-13 |
| NL6410020A (en) | 1965-03-01 |
| BE652476A (en) | 1965-03-01 |
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