GB791824A - Carbamylalkyl phosphorodithioates - Google Patents
Carbamylalkyl phosphorodithioatesInfo
- Publication number
- GB791824A GB791824A GB4773/56A GB477356A GB791824A GB 791824 A GB791824 A GB 791824A GB 4773/56 A GB4773/56 A GB 4773/56A GB 477356 A GB477356 A GB 477356A GB 791824 A GB791824 A GB 791824A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- isopropylamide
- carboxymethyl
- isopropyl
- dialkylphosphorodithioate
- 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 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 abstract 4
- -1 alkali metal salt Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 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
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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 carbamylalkyl phosphorodithioates of the formula: <FORM:0791824/IV (b)/1> wherein R1 is methyl or ethyl and R2 is methyl or isopropyl and contains at least as many carbon atoms as R1, and a process for the manufacture of these compounds wherein an alkali metal salt of an o : o-dialkylphosphorodithioate is treated with an N-methyl- or N-isopropyl-alpha-haloacetamide in the presence of a solvent at a temperature between 10 DEG and 15 DEG C. Suitable solvents include water, alcohols, ketones, dioxane, glycols, esters and aliphatic nitriles. The alkali metal salt of the dialkylphosphorodithioate used as a starting material is preferably purified by preparing an aqueous solution thereof and removing any oily phase which may separate, the aqueous solution being used for condensation with the haloacetamide. Examples describe the preparation of the isopropylamide of 5-carboxymethyl-o : o - diethyl - phosphorodithioate and the methylamide and isopropylamide of 5-carboxymethyl - o : o - dimethyl - phosphorodithioate. Specification 663,270 is referred to.ALSO:Pesticidal compositions comprise one or more compounds of the formula <FORM:0791824/VI/1> wherein R1 is methyl or ethyl and R2 is a methyl or isopropyl radical and contains at least as many carbon atoms as R1, alone or in admixture with other active substances or diluents. Examples describe the use of aqueous dispersions or acetone solutions of the isopropylamide of S-carboxymethyl - O : O - diethylphosphorodithioate and the methylamide and isopropylamide of S-carboxymethyl-O : O-dimethylphosphorodithioate as pesticides. Specification 663,270 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT791824X | 1955-02-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB791824A true GB791824A (en) | 1958-03-12 |
Family
ID=11316695
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4773/56A Expired GB791824A (en) | 1955-02-16 | 1956-02-15 | Carbamylalkyl phosphorodithioates |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE557291A (en) |
CH (1) | CH359695A (en) |
CY (1) | CY175A (en) |
FR (1) | FR1172611A (en) |
GB (1) | GB791824A (en) |
LU (1) | LU35028A1 (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2959608A (en) * | 1959-01-30 | 1960-11-08 | Fisons Pest Control Ltd | Chemical process for making omicron, omicron-dialkyl-5-carbamoylmethyl-phosphorodithioates |
US3013940A (en) * | 1957-06-03 | 1961-12-19 | Montedison Spa | Organo-mercapto-methyleneamides of o, o-dialkyl-thio(or dithio)-phosphorylacetic acids having pesticidal activity |
US3026243A (en) * | 1958-09-04 | 1962-03-20 | Montedison Spa | Control of the olive fly by application of products containing omicron, omicron-dimethylthiophosphorylacetic acid monomethylamide |
US3032579A (en) * | 1958-11-20 | 1962-05-01 | Montedison Spa | Process for the preparation of an n-monoalkylamide of o,o-dimethyldithiophosphorylacetic acid |
US3046296A (en) * | 1957-01-08 | 1962-07-24 | Monsanto Chemicals | Toxic o, o-dimethyl- and o, o-diethyl spentachlorophenyl phosphorothioate |
US3092541A (en) * | 1960-02-24 | 1963-06-04 | Ciba Ltd | New carbamoylalkyl phosphorus ester compounds |
US3092649A (en) * | 1959-09-05 | 1963-06-04 | Bayer Ag | Thiophosphoric acid esters and process for their production |
US3094457A (en) * | 1957-01-08 | 1963-06-18 | Monsanto Chemicals | Toxic omicron, omicron-dimethyl and omicron, omicron-diethyl s-pentachlorophenyl phosphorothioate |
US3102019A (en) * | 1961-08-16 | 1963-08-27 | Monsanto Chemicals | Method for inhibiting germination and preemergent growth of plants using s(n-aryl, n-aliphatic carbamoylmethyl) phosphorothiate triesters |
US3134801A (en) * | 1958-07-12 | 1964-05-26 | Boehringer Sohn Ingelheim | Process for the preparation of o,o-dialkyl-dithiophosphoryl-fatty acid compounds and pesticidal compositions containing the same |
US3210242A (en) * | 1961-05-01 | 1965-10-05 | American Cyanamid Co | Systemic insecticidal alkylcarbamoylmethyl dimethylphosphorodithioates |
US4599329A (en) * | 1983-01-22 | 1986-07-08 | Basf Aktiengesellschaft | O,S-dialkyl S-[carbamyloxyalkyl] dithiophosphates and their use as pesticides |
US4892866A (en) * | 1987-08-07 | 1990-01-09 | Shell International Research Maatshappij B. V. | Stabilized pesticidal composition |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL130008C (en) * | 1960-04-28 | |||
DE2639433A1 (en) * | 1976-09-02 | 1978-03-09 | Bayer Ag | PYRIMIDINYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES |
GB2004187B (en) * | 1977-09-14 | 1982-05-26 | Ici Australia Ltd | Insecticides |
-
0
- BE BE557291D patent/BE557291A/xx unknown
- LU LU35028D patent/LU35028A1/xx unknown
-
1956
- 1956-02-15 GB GB4773/56A patent/GB791824A/en not_active Expired
-
1957
- 1957-02-14 CH CH359695D patent/CH359695A/en unknown
- 1957-02-15 FR FR1172611D patent/FR1172611A/en not_active Expired
-
1958
- 1958-09-06 CY CY17558A patent/CY175A/en unknown
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3094457A (en) * | 1957-01-08 | 1963-06-18 | Monsanto Chemicals | Toxic omicron, omicron-dimethyl and omicron, omicron-diethyl s-pentachlorophenyl phosphorothioate |
US3046296A (en) * | 1957-01-08 | 1962-07-24 | Monsanto Chemicals | Toxic o, o-dimethyl- and o, o-diethyl spentachlorophenyl phosphorothioate |
US3013940A (en) * | 1957-06-03 | 1961-12-19 | Montedison Spa | Organo-mercapto-methyleneamides of o, o-dialkyl-thio(or dithio)-phosphorylacetic acids having pesticidal activity |
US3134801A (en) * | 1958-07-12 | 1964-05-26 | Boehringer Sohn Ingelheim | Process for the preparation of o,o-dialkyl-dithiophosphoryl-fatty acid compounds and pesticidal compositions containing the same |
US3026243A (en) * | 1958-09-04 | 1962-03-20 | Montedison Spa | Control of the olive fly by application of products containing omicron, omicron-dimethylthiophosphorylacetic acid monomethylamide |
US3032579A (en) * | 1958-11-20 | 1962-05-01 | Montedison Spa | Process for the preparation of an n-monoalkylamide of o,o-dimethyldithiophosphorylacetic acid |
US2959608A (en) * | 1959-01-30 | 1960-11-08 | Fisons Pest Control Ltd | Chemical process for making omicron, omicron-dialkyl-5-carbamoylmethyl-phosphorodithioates |
US3092649A (en) * | 1959-09-05 | 1963-06-04 | Bayer Ag | Thiophosphoric acid esters and process for their production |
US3092541A (en) * | 1960-02-24 | 1963-06-04 | Ciba Ltd | New carbamoylalkyl phosphorus ester compounds |
US3210242A (en) * | 1961-05-01 | 1965-10-05 | American Cyanamid Co | Systemic insecticidal alkylcarbamoylmethyl dimethylphosphorodithioates |
US3102019A (en) * | 1961-08-16 | 1963-08-27 | Monsanto Chemicals | Method for inhibiting germination and preemergent growth of plants using s(n-aryl, n-aliphatic carbamoylmethyl) phosphorothiate triesters |
US4599329A (en) * | 1983-01-22 | 1986-07-08 | Basf Aktiengesellschaft | O,S-dialkyl S-[carbamyloxyalkyl] dithiophosphates and their use as pesticides |
US4892866A (en) * | 1987-08-07 | 1990-01-09 | Shell International Research Maatshappij B. V. | Stabilized pesticidal composition |
Also Published As
Publication number | Publication date |
---|---|
BE557291A (en) | 1900-01-01 |
CY175A (en) | 1958-09-06 |
CH359695A (en) | 1962-01-31 |
LU35028A1 (en) | 1900-01-01 |
FR1172611A (en) | 1959-02-12 |
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