GB691267A - Neutral esters of selenophosphoric acid - Google Patents
Neutral esters of selenophosphoric acidInfo
- Publication number
- GB691267A GB691267A GB20702/50A GB2070250A GB691267A GB 691267 A GB691267 A GB 691267A GB 20702/50 A GB20702/50 A GB 20702/50A GB 2070250 A GB2070250 A GB 2070250A GB 691267 A GB691267 A GB 691267A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- alkyl
- methyl
- ethyl
- radicals
- 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 3
- 230000007935 neutral effect Effects 0.000 title 1
- JRPHGDYSKGJTKZ-UHFFFAOYSA-N selenophosphoric acid Chemical compound OP(O)([SeH])=O JRPHGDYSKGJTKZ-UHFFFAOYSA-N 0.000 title 1
- -1 methylmercaptoethyl Chemical group 0.000 abstract 16
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000003701 inert diluent Substances 0.000 abstract 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 229910052711 selenium Inorganic materials 0.000 abstract 2
- 229910052783 alkali metal Chemical group 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000011669 selenium Substances 0.000 abstract 1
- 239000007787 solid Substances 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises the selenophosphoric esters of the general formula <FORM:0691267/IV (b)/1> wherein R1 and R2 are the same or different alkyl radicals and R3 is an alkyl, aralkyl or aryl (including substituted phenyl) radical, and when R3 is an alkyl or aralkyl radical, the alkyl chain linked to selenium may be interrupted by a sulphur atom, and a process for preparing the above compounds by reacting a dialkyl phosphite <FORM:0691267/IV (b)/2> wherein R1 and R2 have the above significance and X is hydrogen or an alkali metal, with a selenocyanide R3SeCN, where R3 has the above significance, in an inert diluent at temperatures ranging from room temperature to about 100 DEG C. The radicals R1 and R2 are preferably lower alkyl p radicals, e.g. methyl or ethyl radicals. The group R3 may be a methyl, ethyl, propyl, butyl, hexyl, dodecyl, benzyl, naphthylmethyl or phenyl radical, or a phenyl radical substituted with a halogen atom, or an alkyl, alkoxy or nitro group, and when the alkyl chain is interrupted by sulphur, the group R3 may be a methylmercaptoethyl, ethylmercaptoethyl, phenylmercaptoethyl or (methylphenyl)-mercaptoethyl radical. The inert diluent may be benzene or toluene. In the examples the following compounds of the above general formula are referred to: R1 and R2 are methyl and R3 is p-nitrophenyl; R1 and R2 are ethyl and R3 is methyl, ethyl, n-propyl, n-butyl, hexyl, dodecyl, phenyl, p-chlorophenyl, o-methoxyphenyl, p-methoxyphenyl, p-nitrophenyl, alpha - naphthylmethyl, ethylmercaptoethyl, methylmercaptoethyl, and p-methylphenylmercaptoethyl.ALSO:Insecticidal preparations comprise a liquid or solid carrier and a selenophosphoric ester of the general formula wherein R1 and R2 represent the same or different alkyl radicals and R3 represents an alkyl, aralkyl or aryl (including substituted phenyl) radical, and when R3 represents an alkyl or <FORM:0691267/VI/1> aralkyl radical the alkyl chain linked to the selenium atom may be interrupted by a sulphur atom. Preferably the radicals R1 and R2 are lower alkyl radicals e.g., methyl and ethyl radicals. The radical R3 may be a methyl, ethyl, propyl, butyl, hexyl, dodecyl, benzyl, naphthylmethyl or phenyl radical, or a phenyl radical substituted with a halogen atom or an alkyl, alkoxy or nitro group, and when the alkyl chain is interrupted by sulphur the radical R3 may be a methylmercaptoethyl, ethylmercaptoethyl, phenylmercaptoethyl or (methylphenyl)-mercaptoethyl radical. In the examples preparations are referred to consisting of water or dust and each one of the following compounds of the above general formula:-R1 and R2 are methyl and R3 is p-nitrophenyl; R1 and R2 are ethyl and R3 is methyl, ethyl, n-propyl, n-butyl, hexyl, dodecyl, phenyl, p-chlorophenyl, o-methoxyphenyl, p-methoxyphenyl, p-nitrophenyl, alpha-naphthylmethyl, ethylmercaptoethyl, methylmercaptoethyl and p-methylphenylmercaptoethyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR691267X | 1949-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB691267A true GB691267A (en) | 1953-05-06 |
Family
ID=9032863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20702/50A Expired GB691267A (en) | 1949-08-20 | 1950-08-21 | Neutral esters of selenophosphoric acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB691267A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2126895A (en) * | 1982-09-15 | 1984-04-04 | Univ Washington | Compositions and methods to reduce animal browsing damage to plants |
-
1950
- 1950-08-21 GB GB20702/50A patent/GB691267A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2126895A (en) * | 1982-09-15 | 1984-04-04 | Univ Washington | Compositions and methods to reduce animal browsing damage to plants |
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