GB673877A - Diamido-thiophosphates and parasiticidal compositions comprising same - Google Patents
Diamido-thiophosphates and parasiticidal compositions comprising sameInfo
- Publication number
- GB673877A GB673877A GB2677549A GB2677549A GB673877A GB 673877 A GB673877 A GB 673877A GB 2677549 A GB2677549 A GB 2677549A GB 2677549 A GB2677549 A GB 2677549A GB 673877 A GB673877 A GB 673877A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- butyl
- radicals
- ethyl
- hydrogen
- 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 abstract 2
- 230000000590 parasiticidal effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 abstract 4
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 abstract 3
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- -1 cycloalkyl amine Chemical class 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- XPUSKKJATQFMBF-UHFFFAOYSA-N 2,4,5-tribromophenol Chemical compound OC1=CC(Br)=C(Br)C=C1Br XPUSKKJATQFMBF-UHFFFAOYSA-N 0.000 abstract 1
- FRPHJINKMDMSPH-UHFFFAOYSA-N 2-bromo-4,6-dichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Br FRPHJINKMDMSPH-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- BGULGLBUWZQWOL-UHFFFAOYSA-N N-bis(chloroamino)phosphinothioylbutan-1-amine Chemical compound C(CCC)NP(=S)(NCl)NCl BGULGLBUWZQWOL-UHFFFAOYSA-N 0.000 abstract 1
- PZQWCJYXKNTXNR-UHFFFAOYSA-N N-bis(chloroamino)phosphinothioylethanamine Chemical compound C(C)NP(=S)(NCl)NCl PZQWCJYXKNTXNR-UHFFFAOYSA-N 0.000 abstract 1
- 229910018894 PSCl3 Inorganic materials 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- 230000002538 fungal effect Effects 0.000 abstract 1
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 abstract 1
- 150000003385 sodium Chemical class 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0673877/IV (b)/1> wherein X is chlorine or bromine, R1 represents an alkyl radical, each of R2, R3, R4 may be hydrogen, alkyl, aralkyl or cycloalkyl and n is an integer from 3 to 5. These compounds may be made by reacting equimolecular proportions of the polyhalophenol and thiophosphoryl chloride to give the O-polyhalophenyl-dichlorothiophosphate which may be reacted with (1) at least 4 mols. of the appropriate amine, or (3) successively with 2 mols. each of an amine and ammonia. Alternatively the polyhalophenol may be reacted with a compound <FORM:0673877/IV (b)/2> p (obtained from the appropriate amine and thiophosphoryl trichloride PSCl3) followed by reaction of the product with the appropriate alkyl, aralkyl, or cycloalkyl amine or ammonia. In examples: (1) O - 2,4,5 - trichlorophenyl N,N,N1,N1 - tetramethyldiamidothiophosphate is prepared by reacting 2,4,5-trichlorophenol and thiophosphoryl chloride and treating the product with diethylamine; (4) O-2,4,5-trichlorophenyl N,N,N1 - triethylamidothiophosphate is obtained by reacting 2,4,5-trichlorophenol with N-ethyl dichlorothiophosphoramide and reacting the product with dimethylamine; (7) O - 2,4,5 - trichlorophenyl N - n - butyl-diamidothiophosphate is prepared by reacting 2,4,5-trichlorophenol with N-n-butyl-dichlorothiophosphoramide and reacting the product with liquid ammonia; (9) O-2,4,6-trichlorophenyl N - cyclohexyl - N1 - ethyldiamidothiophosphate is prepared by reacting the sodium derivative of 2,4,6-trichlorophenol with N-ethyldichlorothiophosphoramide and reacting the product with cyclohexylamine. Similarly to (1) are prepared compounds of the first general formula in which X=Cl, n=3 or 5, and the radicals R1, R2, R3, R4 are hydrogen o n-propyl, ethyl, n-dodecyl, n-butyl, isopropyl, or sec.-butyl radicals. Similarly to (4) are prepared compounds of the general formula in which R1, R2 are methyl or n-butyl radicals and R3, R4 are ethyl or hydrogen. Similarly to (7) are obtained products in which R1, R2 are hydrogen or ethyl or n-dodecyl radicals. Similarly to (9) are produced compounds in which R1, R2, R3, R4 are radicals selected from hydrogen and methyl, ethyl, n-propyl, cyclohexyl, dodecyl, n-butyl, isopropyl or benzyl radicals. Other suitable halophenols are pentabromophenol, 2,4,6-tribromophenol, 2,4,5-tribromophenol, 2,4-dichloro-6-bromophenol. Various compositions of the products for use in controlling insect, mite and fungal organisms are described (see Group VI).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2677549A GB673877A (en) | 1949-10-18 | 1949-10-18 | Diamido-thiophosphates and parasiticidal compositions comprising same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2677549A GB673877A (en) | 1949-10-18 | 1949-10-18 | Diamido-thiophosphates and parasiticidal compositions comprising same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB673877A true GB673877A (en) | 1952-06-11 |
Family
ID=10248988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2677549A Expired GB673877A (en) | 1949-10-18 | 1949-10-18 | Diamido-thiophosphates and parasiticidal compositions comprising same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB673877A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957301C (en) * | 1953-04-16 | 1957-01-31 | Ciba Geigy | Process for the production of new, phosphorus-containing organic compounds |
| US9398771B2 (en) | 2011-11-23 | 2016-07-26 | Roderick William Phillips | Spray apparatuses, uses of diatomaceous earth, and methods of controlling insect populations |
| US10485351B2 (en) | 2011-05-03 | 2019-11-26 | Roderick William Phillips | Headboard apparatus for holding a decorative cover |
-
1949
- 1949-10-18 GB GB2677549A patent/GB673877A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957301C (en) * | 1953-04-16 | 1957-01-31 | Ciba Geigy | Process for the production of new, phosphorus-containing organic compounds |
| US10485351B2 (en) | 2011-05-03 | 2019-11-26 | Roderick William Phillips | Headboard apparatus for holding a decorative cover |
| US11140993B2 (en) | 2011-05-03 | 2021-10-12 | Roderick William Phillips | Headboard apparatus for holding a decorative cover and having diatomaceous earth incorporated therein for pest control |
| US9398771B2 (en) | 2011-11-23 | 2016-07-26 | Roderick William Phillips | Spray apparatuses, uses of diatomaceous earth, and methods of controlling insect populations |
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