GB1283749A - Novel carbamylmethyldithiophosphates, processes for their preparation, and compositions incorporating them - Google Patents
Novel carbamylmethyldithiophosphates, processes for their preparation, and compositions incorporating themInfo
- Publication number
- GB1283749A GB1283749A GB52479/69A GB5247969A GB1283749A GB 1283749 A GB1283749 A GB 1283749A GB 52479/69 A GB52479/69 A GB 52479/69A GB 5247969 A GB5247969 A GB 5247969A GB 1283749 A GB1283749 A GB 1283749A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reacting
- sch
- alkali metal
- chloride
- 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
- 239000000203 mixture Substances 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 8
- 150000008064 anhydrides Chemical class 0.000 abstract 5
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 3
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- -1 carbamyl methyl dithiophosphates Chemical class 0.000 abstract 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 241001595582 Octolasmis cor Species 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic 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
- 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)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1283749 Carbamylmethyldithiophosphate esters ROUSSEL-UCLAF 27 Oct 1969 [29 Oct 1968] 52479/69 Heading C2P The invention comprises carbamyl methyl dithiophosphates of the general formula wherein R<SP>1</SP> is a C 1 -C 7 alkyl radical, and R<SP>2</SP> and R<SP>3</SP> which may be the same or different are C 2 to C 7 alkenyl radicals. They may be obtained either (a) by reacting HalCH 2 CON(OR<SP>2</SP>)R<SP>3</SP>, wherein Hal is Cl or Br, in an organic solvent, with an alkali metal salt of the formula (R<SP>1</SP>O) 2 P(S)SX wherein X is an alkali metal, or (b) by reacting a functional derivative of the acids (R<SP>1</SP>O) 2 P(S)SCH 2 COOH, e.g. an acid chloride, anhydride, or mixed anhydride of the acid, with an O,N-dialkenyl hydroxylamine of the formula HN(OR<SP>2</SP>)R<SP>3</SP>, preferably in the presence of a basic agent, e.g. pyridine or triethylamine. The products have insecticidal and acaricidal properties and may be used in admixture with solid or liquid carriers or diluents, and optionally surface-active agents, e.g. in the form of powders, wettable powders, granules, suspensions, emulsions, or solutions. The potassium salt of O,O-dimethyl dithiophosphate is prepared by reacting O,O-dimethyl dithiophosphate in methanol with KOH. O,O - dimethyl - S - carboxymethyldithiophosphate is prepared by adding an aqueous solution of O,O-dimethyl dithiophosphate and an aqueous solution of KOH to a refluxing solution of monochloroacetic acid in chloroform and water. The product, after isolation, is converted to its acid chloride by reacting with oxalyl chloride at 60 C. in an anhydrous toluene medium. The acid chlorides may be obtained generally by reacting the acid with thionyl chloride or oxalyl chloride. Mixed anhydrides of the general formula (R<SP>1</SP>O) 2 P(S)SCH 2 CO.O.COR<SP>4</SP>, wherein R<SP>4</SP> is the acyl residue of a carboxylic acid, may be obtained by reacting R<SP>4</SP>COCl with an alkali metal salt of the acid (R<SP>1</SP>O) 2 P(S)SCH 2 COOH which may be prepared by reacting an alkali metal carbonate or hydroxide with the free acid. The mixed anhydrides may also be obtained by reacting the acid chloride R<SP>4</SP>COCl with the acid (R<SP>1</SP>O) 2 P(S)SCH 2 COOH in the presence of a tertiary base or by reacting the said acid with ketene to give the anhydride in which R<SP>4</SP> is CH 3 .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR171759 | 1968-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1283749A true GB1283749A (en) | 1972-08-02 |
Family
ID=8656249
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB542/72A Expired GB1283750A (en) | 1968-10-29 | 1969-10-27 | Novel halogeno-acetamides and processes for their preparation |
| GB52479/69A Expired GB1283749A (en) | 1968-10-29 | 1969-10-27 | Novel carbamylmethyldithiophosphates, processes for their preparation, and compositions incorporating them |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB542/72A Expired GB1283750A (en) | 1968-10-29 | 1969-10-27 | Novel halogeno-acetamides and processes for their preparation |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE740759A (en) |
| ES (1) | ES372949A1 (en) |
| FR (1) | FR1588747A (en) |
| GB (2) | GB1283750A (en) |
| IL (1) | IL33163A (en) |
| LU (1) | LU59700A1 (en) |
| NL (1) | NL6916213A (en) |
| ZA (1) | ZA697607B (en) |
-
1968
- 1968-10-29 FR FR171759A patent/FR1588747A/fr not_active Expired
-
1969
- 1969-10-10 IL IL33163A patent/IL33163A/en unknown
- 1969-10-24 LU LU59700D patent/LU59700A1/xx unknown
- 1969-10-24 BE BE740759D patent/BE740759A/xx unknown
- 1969-10-27 GB GB542/72A patent/GB1283750A/en not_active Expired
- 1969-10-27 GB GB52479/69A patent/GB1283749A/en not_active Expired
- 1969-10-28 NL NL6916213A patent/NL6916213A/xx unknown
- 1969-10-28 ES ES372949A patent/ES372949A1/en not_active Expired
- 1969-10-29 ZA ZA697607*A patent/ZA697607B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES372949A1 (en) | 1971-11-16 |
| LU59700A1 (en) | 1970-01-12 |
| ZA697607B (en) | 1971-03-31 |
| IL33163A0 (en) | 1969-12-31 |
| GB1283750A (en) | 1972-08-02 |
| NL6916213A (en) | 1970-05-04 |
| IL33163A (en) | 1973-02-28 |
| BE740759A (en) | 1970-04-24 |
| FR1588747A (en) | 1970-04-17 |
| DE1954235A1 (en) | 1970-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |