GB800220A - O-(3,4-dichlorophenyl) n,n-dialkyl phosphorodiamidothioates - Google Patents
O-(3,4-dichlorophenyl) n,n-dialkyl phosphorodiamidothioatesInfo
- Publication number
- GB800220A GB800220A GB7216/57A GB721657A GB800220A GB 800220 A GB800220 A GB 800220A GB 7216/57 A GB7216/57 A GB 7216/57A GB 721657 A GB721657 A GB 721657A GB 800220 A GB800220 A GB 800220A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dichlorophenyl
- phosphorodichloridothioate
- employed
- phosphorodiamidothioates
- dialkyl
- 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
- JADWVLYMWVNVAN-UHFFFAOYSA-N ctk0h5271 Chemical class NP(N)(O)=S JADWVLYMWVNVAN-UHFFFAOYSA-N 0.000 title abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal salt Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- BGOJEWWWTOYWNF-UHFFFAOYSA-N dichloro-(3,4-dichlorophenoxy)-sulfanylidene-lambda5-phosphane Chemical compound P(OC1=CC(=C(C=C1)Cl)Cl)(Cl)(Cl)=S BGOJEWWWTOYWNF-UHFFFAOYSA-N 0.000 abstract 1
- OOFVSLAKBNBEEH-UHFFFAOYSA-N dichloro-hydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(Cl)(Cl)=S OOFVSLAKBNBEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
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)
Abstract
The invention comprises O-(3,4-dichlorophenyl)-N,N1-dialkyl phosphorodiamidothioates having the formula <FORM:0800220/IV (b)/1> in which R represents either methyl or ethyl. They may be prepared by reacting at least four molecular proportions of methylamine or ethylamine in the presence of an inert organic solvent with one molecular proportion of O-(3,4-dichlorophenyl) - phosphorodichloridothioate. The reaction may be effected at from - 10 DEG C. to 30 DEG C. and specified organic solvents are acetone, methyl ethyl ketone, carbon tetrachloride, benzene and methylene chloride. It is preferred to use an aqueous amine and a water-miscible solvent but gaseous amine may also be used by contacting it portionwise with the phosphorodichloridothioate dissolved in the reaction solvent. Examples are given for the production of O-3,4-dichlorophenyl)-N,N1-dimethyl (and N,N1-diethyl) phosphorodiamidothioates respectively, the reaction being carried out in each case with an aqueous solution of the corresponding amine which is added portionwise to the O-(3,4-dichlorophenyl) phosphorodichloridothioate dissolved in benzene. The products are stated to be valuable as pesticides (see Group VI). The O - (3,4 - dichlorophenyl) - phosphorodichloridothioate employed as starting material may be prepared by reacting an excess of phosphorus thiochloride with an alkali metal salt of 3,4-dichlorophenol.ALSO:A pesticidal composition comprises as the active ingredient an O-(3,4-dichlorophenyl)-N,N1-dialkyl phosphorodiamidothioate having the formula <FORM:0800220/VI/1> in which R is methyl or ethyl (see Group IV (b)). The product may be dispersed on a finely-divided carrier and employed as a dust or may be employed in an oil, in water emulsion or in water dispersion.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US800220XA | 1956-03-05 | 1956-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB800220A true GB800220A (en) | 1958-08-20 |
Family
ID=22154754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7216/57A Expired GB800220A (en) | 1956-03-05 | 1957-03-05 | O-(3,4-dichlorophenyl) n,n-dialkyl phosphorodiamidothioates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB800220A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1224312B (en) * | 1960-04-22 | 1966-09-08 | Dow Chemical Co | Process for the preparation of phosphoric acid-O-chlorophenyl-O-alkylesteramides |
-
1957
- 1957-03-05 GB GB7216/57A patent/GB800220A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1224312B (en) * | 1960-04-22 | 1966-09-08 | Dow Chemical Co | Process for the preparation of phosphoric acid-O-chlorophenyl-O-alkylesteramides |
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