GB926604A - Phosphorodithioates and preparation thereof - Google Patents
Phosphorodithioates and preparation thereofInfo
- Publication number
- GB926604A GB926604A GB148361A GB148361A GB926604A GB 926604 A GB926604 A GB 926604A GB 148361 A GB148361 A GB 148361A GB 148361 A GB148361 A GB 148361A GB 926604 A GB926604 A GB 926604A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- aryl radical
- group
- radical
- alkyl radical
- 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
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 title 1
- -1 C1-C6 alkyl radical Chemical group 0.000 abstract 7
- 150000005840 aryl radicals Chemical group 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 239000008096 xylene Substances 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
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
-
- 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
-
- 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
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
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 a phosphorodithioate of the general formula U-S-P(S)-(OR1)2 wherein U is an alkynyl group of the formula R.CC- wherein R is a C1-C6 alkyl radical or an aryl radical, or U is an alkenyl group of the formula HC(R2)=CH-wherein R2 is a hydrogen atom, a C1-C6 alkyl radical or an aryl radical, and R1 is a C1-C6 alkyl radical or an aryl radical. They may be obtained by reacting a compound of the formula (R1O)2.P(:S).S.S.P(:S).(OR1)2 with approximately equimolar quantities of an appropriate compound selected from: (1) an alkali metal salt of a primary acetylene RCC-M wherein R is as defined above and M is an alkali metal, e.g. Na, K or Li, and (2) a metal vinyl compound of the structure H.C(R2)=CHMgX or H.C(R2)= CHM wherein R2 and M are as defined above and X is a halogen atom, e.g. Cl or Br. Suitable temperatures are from 0 to 50 DEG C. and an inert organic solvent, e.g. hexane, cyclohexane, ether, xylene or toluene, may be present. Specified R1 groups are methyl, ethyl, propyl, pentyl, phenyl, and naphthyl. The products have insecticidal properties (see Group VI).ALSO:An insecticidal composition comprises a carrier and a phosphorodithioate of the general formula U-S-P(S)(OR1)2 wherein U is an alkynyl group of the formula R.C C-, wherein R is a C1-C6 alkyl radical or an aryl radical, or U is an alkenyl group of the formula H.C(R2) = CH-, wherein R2 is a hydrogen atom, a C1-C6 alkyl radical or an aryl radical, R1 is a C1-C6 alkyl group or an aryl radical (see Group IV (b)). Specified carriers are talc, clays, diatomaceous earths, water and organic solvents. A suitable composition for spraying is obtained by dissolving O,O-diethyl, S-b -styryl (or vinyl) phosphorodithioate, or the corresponding O,O-dimethyl compounds in a mixture of acetone and water. The composition may be an emulsion.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28236A US3019159A (en) | 1960-05-11 | 1960-05-11 | Novel phosphorodithioates and methods for preparing the same |
| US53613A US3021352A (en) | 1960-09-02 | 1960-09-02 | Preparation of s-(1-alkenyl) phosphorodithioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB926604A true GB926604A (en) | 1963-05-22 |
Family
ID=26703457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB148361A Expired GB926604A (en) | 1960-05-11 | 1961-01-13 | Phosphorodithioates and preparation thereof |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE598857A (en) |
| CH (1) | CH398554A (en) |
| DE (1) | DE1150069B (en) |
| GB (1) | GB926604A (en) |
| NL (1) | NL259863A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5057235A (en) * | 1988-06-23 | 1991-10-15 | Mobil Oil Corporation | Sulfur-phosphorus adducts of chromium catalyzed polyalphaolefins |
-
0
- NL NL259863D patent/NL259863A/xx unknown
-
1961
- 1961-01-05 BE BE598857A patent/BE598857A/en unknown
- 1961-01-12 CH CH37461A patent/CH398554A/en unknown
- 1961-01-12 DE DEA36478A patent/DE1150069B/en active Pending
- 1961-01-13 GB GB148361A patent/GB926604A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5057235A (en) * | 1988-06-23 | 1991-10-15 | Mobil Oil Corporation | Sulfur-phosphorus adducts of chromium catalyzed polyalphaolefins |
Also Published As
| Publication number | Publication date |
|---|---|
| NL259863A (en) | |
| CH398554A (en) | 1966-03-15 |
| DE1150069B (en) | 1963-06-12 |
| BE598857A (en) | 1961-07-05 |
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