GB877470A - Thiophosphoric acid esters - Google Patents
Thiophosphoric acid estersInfo
- Publication number
- GB877470A GB877470A GB3282458A GB3282458A GB877470A GB 877470 A GB877470 A GB 877470A GB 3282458 A GB3282458 A GB 3282458A GB 3282458 A GB3282458 A GB 3282458A GB 877470 A GB877470 A GB 877470A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- sulphur
- aryl
- methyl
- oxygen
- 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
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 9
- 239000005864 Sulphur Substances 0.000 abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 8
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 4
- -1 C1-C4 alkyl radicals Chemical class 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 abstract 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000003609 aryl vinyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 235000012222 talc Nutrition 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises thiophosphoric acid esters of the formula:- <FORM:0877470/IV (b)/1> wherein Ar is phenyl, halogen-substituted phenyl, or C1-C4 alkyl-substituted phenyl radical, R1 and R2 are C1-C4 alkyl radicals, and X and Y are oxygen or sulphur with the proviso that when Y is sulphur X must also be sulphur. They may be obtained by reacting an appropriate O,O-dialkyl dithio- or monothio phosphoric acid with an appropriate aryl vinyl ether or thioether. The reaction may be carried out in an inert solvent, e.g. a hydrocarbon such as benzene or toluene and specified reaction temperatures are 50 - 70 DEG C. Examples are given for the production of compounds in which R1 and R2 are ethyl, X and Y are sulphur and Aryl is phenyl, p-chloro-phenyl, 3,4-dichlorophenyl, and p-methyl-phenyl respectively; R1 and R2 are ethyl, Y is oxygen, X is sulphur and Aryl is phenyl, p-chloro-phenyl, p-methyl-phenyl and 3,4-dimethyl phenyl respectively; R1 and R2 are methyl, X and Y are sulphur and aryl is phenyl, p-chlorophenyl, p-bromophenyl and p-methyl phenyl respectively. The products have insecticidal properties (see Group VI). Specification 676,776 is referred to.ALSO:An insecticidal composition comprises as active ingredient a thiophosphoric acid ester of the general formula <FORM:0877470/VI/1> in which Aryl is a phenyl, halogen-substituted phenyl, or C1-C4 alkyl substituted phenyl radical R1 and R2 are C1-C4 alkyl radicals , and X and Y are oxygen or sulphur with the proviso that when Y is sulphur X must also be sulphur (see Group IV (b)) and a solid or liquid carrier or diluent. Specified diluents are talcum, chalk, kieselguhr, organic solvents and water and the composition may be in the form of an aqueous emulsion obtained by using e.g. acetone or dimethyl formamide as dissolving agent, and a commercial emulsifier. Specified aryl radicals are phenyl, p-chlorophenyl, p-bromo-phenyl, p-methyl phenyl, 3,4-dichlorophenyl and 3,4-dimethyl-phenyl. Specification 676,776 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0024248 | 1957-10-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB877470A true GB877470A (en) | 1961-09-13 |
Family
ID=7091153
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3282458A Expired GB877470A (en) | 1957-10-25 | 1958-10-14 | Thiophosphoric acid esters |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE572348A (en) |
CH (1) | CH382141A (en) |
DE (1) | DE1070171B (en) |
FR (1) | FR1206459A (en) |
GB (1) | GB877470A (en) |
-
0
- BE BE572348D patent/BE572348A/xx unknown
- DE DENDAT1070171D patent/DE1070171B/en active Pending
-
1958
- 1958-10-06 CH CH6470758A patent/CH382141A/en unknown
- 1958-10-14 GB GB3282458A patent/GB877470A/en not_active Expired
- 1958-10-23 FR FR1206459D patent/FR1206459A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH382141A (en) | 1964-09-30 |
FR1206459A (en) | 1960-02-10 |
DE1070171B (en) | 1959-12-03 |
BE572348A (en) |
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