GB1312671A - Pesticidal o,s-dialkyl s-organo thioalkyl dithiophosphates - Google Patents
Pesticidal o,s-dialkyl s-organo thioalkyl dithiophosphatesInfo
- Publication number
- GB1312671A GB1312671A GB1114570A GB1114570A GB1312671A GB 1312671 A GB1312671 A GB 1312671A GB 1114570 A GB1114570 A GB 1114570A GB 1114570 A GB1114570 A GB 1114570A GB 1312671 A GB1312671 A GB 1312671A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- alkyl
- agent
- dialkyl
- organo
- 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
- 230000000361 pesticidal effect Effects 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- -1 alkyl sulphonate Chemical compound 0.000 abstract 3
- 239000002168 alkylating agent Substances 0.000 abstract 3
- 229940100198 alkylating agent Drugs 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000012380 dealkylating agent Substances 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000020335 dealkylation Effects 0.000 abstract 2
- 238000006900 dealkylation reaction Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation 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
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 150000007944 thiolates Chemical class 0.000 abstract 1
- 150000003573 thiols Chemical class 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
Abstract
1312671 Substituted dithiophosphate esters ESSO RESEARCH & ENG CO 9 March 1970 [1 May 1969] 11145/70 Addition to 1287621 Heading C2P An O,S<SP>1</SP>-dialkyl S-organo-thioalkyl dithiophosphate is obtained by (a) reacting a dithiophosphate ester (R<SP>1</SP>O)(R<SP>1</SP>O)P(S)SR<SP>111</SP>whereinR<SP>1</SP> is alkyl and R<SP>111</SP> is an organothioalkyl radical or an alkenyl radical with a dealkylating agent and (b) reacting the dealkylated compound with an alkylating agent and (c) when R<SP>111</SP> is an alkenyl radical further reacting the product of (b) with an organic thiol R 1 SH, the organo radical and the radical R 1 being an unsubstituted or substituted hydrocarbyl radical. The invention also includes as novel compounds products obtainable as above and having the general formula wherein R<SP>V</SP> is methyl or ethyl, R<SP>VI</SP> is a C 3 or C 4 alkyl group, R<SP>VII</SP> is a C 1 to C 10 substituted or unsubstituted hydrocarbon radical especially C 1 -C 8 alkyl, phenyl or chlorinated phenyl, B is a C 1 -C 4 alkylene radical, and y is 0, 1 or 2 provided that when B is C 1 alkylene, y is 0 and that when B is C 2 alkylene, R<SP>VI</SP> is a primary or secondary C 3 or C 4 alkyl radical. The dealkylating agent used in step (a) is suitably a nitrogen or phosphorus base, a thiolate or an inorganic salt and the alkylating agent in step (b) is suitably an alkyl halide, alkyl sulphonate, dialkyl sulphate, alkyl phosphate or trialkyl phosphite. Several dealkylating and alkylating agents are specified. It is preferred to carry out both steps (a) and (b) in the presence of a polar organic solvent. The products can be readily selectively oxidized to the corresponding sulphoxides or sulphones, e.g. by using chemical oxidants such as peroxides, e.g. aqueous H 2 O 2 , nitric acid, permanganates and bromine. When the alkyl group removed in the dealkylation step is the same as that introduecd by the alkylation step the two steps may be carried out simultaneously by use of an appropriate dehydrocarbylating agent the by-product of dealkylation functioning as the hydrocarbylating agent, the net result being isomerization of the starting O,O<SP>1</SP>-dialkyl ester to the O,S<SP>1</SP>-dialkyl ester. The products, especially the novel compounds of the above given formula have pesticidal properties and may be used in admixture with suitable carriers or diluents to provide pesticidal compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82111769A | 1969-05-01 | 1969-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1312671A true GB1312671A (en) | 1973-04-04 |
Family
ID=25232565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1114570A Expired GB1312671A (en) | 1969-05-01 | 1970-03-09 | Pesticidal o,s-dialkyl s-organo thioalkyl dithiophosphates |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE754199A (en) |
| CH (1) | CH560009A5 (en) |
| DE (1) | DE2020604C3 (en) |
| FR (1) | FR2047223A5 (en) |
| GB (1) | GB1312671A (en) |
| IL (1) | IL33966A (en) |
| NL (1) | NL7005195A (en) |
| ZA (1) | ZA701319B (en) |
-
0
- BE BE754199D patent/BE754199A/en unknown
-
1969
- 1969-02-27 ZA ZA701319A patent/ZA701319B/en unknown
-
1970
- 1970-02-25 IL IL33966A patent/IL33966A/en unknown
- 1970-03-09 GB GB1114570A patent/GB1312671A/en not_active Expired
- 1970-04-10 NL NL7005195A patent/NL7005195A/xx unknown
- 1970-04-23 CH CH612070A patent/CH560009A5/xx not_active IP Right Cessation
- 1970-04-28 DE DE2020604A patent/DE2020604C3/en not_active Expired
- 1970-04-30 FR FR7016082A patent/FR2047223A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2020604B2 (en) | 1973-05-24 |
| ZA701319B (en) | 1971-01-27 |
| IL33966A (en) | 1973-11-28 |
| BE754199A (en) | 1971-02-01 |
| CH560009A5 (en) | 1975-03-27 |
| IL33966A0 (en) | 1970-04-20 |
| DE2020604A1 (en) | 1971-02-25 |
| NL7005195A (en) | 1970-11-03 |
| DE2020604C3 (en) | 1974-01-03 |
| FR2047223A5 (en) | 1971-03-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB942130A (en) | Method of preparing organic sulfates or sulfonates | |
| NL971020I2 (en) | Azolylmethyloxirane, its preparation and use as medicines and plant protection products. | |
| GB1377225A (en) | Acylanilino compounds and herbicidal compositions containing them | |
| AU527008B2 (en) | Antiwear additive | |
| GB1382754A (en) | N-sulphenylated n-methylcarbamic acid aryl esters and their use as insecticides acaricides and nematicides | |
| FR2386604B1 (en) | ||
| GB1387661A (en) | Phosphorus-containing pyrimidine derivatives having pesticidal properties | |
| GB906982A (en) | Thiophosphoric acid esters | |
| GB1312671A (en) | Pesticidal o,s-dialkyl s-organo thioalkyl dithiophosphates | |
| GB1308802A (en) | Preparation of s-2-organic thioalkyl esters of thiophosphorus acids | |
| GB779808A (en) | Thiophosphoric acid esters and pesticidal preparations containing the same | |
| GB1261345A (en) | Sulphur-containing benzyl derivatives and pesticidal compositions containing them | |
| GB939946A (en) | Dithiophosphonic acid esters | |
| GB1341844A (en) | Manufacture of pyrimidines | |
| ES2021014B3 (en) | FLAME RETARDING OLIGOMER ADDITIVES, PROCESS FOR ITS PREPARATION AND ITS USE TO PRODUCE A LINEAR POLYESTER WITH SELF-EXTINGUISHING CHARACTERISTICS. | |
| GB919200A (en) | New thiophosphorus acid esters | |
| GB1087066A (en) | Azido substituted organophosphorus compounds, processes for preparing them, and pesticidal compositions containing the same | |
| GB864632A (en) | Thionophosphonic acid esters | |
| GB1276201A (en) | Organotin imides and their use as pesticides | |
| GB1168256A (en) | New Phosphite Triesters and their use in Stabilising Rubbers | |
| GB1314102A (en) | Preparation of pesticidal s-vinylic esters of thiophosphorus acids by addition of phosphoryl disulphides to acetylenes | |
| GB1077227A (en) | Xanthic acid esters and their use as pesticides | |
| GB795340A (en) | New insecticidal esters of dithiophosphoric acid | |
| ES257060A1 (en) | New fungicidal compounds | |
| GB1367274A (en) | Dithio-and trithiophosphoric acid esters and their use as pesticides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |