GB744360A - Manufacture of organic compounds containing halogen and phosphorus - Google Patents
Manufacture of organic compounds containing halogen and phosphorusInfo
- Publication number
- GB744360A GB744360A GB23482/52A GB2348252A GB744360A GB 744360 A GB744360 A GB 744360A GB 23482/52 A GB23482/52 A GB 23482/52A GB 2348252 A GB2348252 A GB 2348252A GB 744360 A GB744360 A GB 744360A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloral
- butyl
- methyl
- residue
- alkyl
- 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
- 229910052736 halogen Inorganic materials 0.000 title abstract 2
- 150000002367 halogens Chemical class 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000002894 organic compounds Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229960004319 trichloroacetic acid Drugs 0.000 abstract 3
- -1 2-butyl octyl Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 2
- VCPLTYZBTGSWFP-UHFFFAOYSA-N (4-chlorophenyl) diethyl phosphite Chemical compound CCOP(OCC)OC1=CC=C(Cl)C=C1 VCPLTYZBTGSWFP-UHFFFAOYSA-N 0.000 abstract 1
- YTGSYRVSBPFKMQ-UHFFFAOYSA-N 2,2,2-tribromoacetaldehyde Chemical compound BrC(Br)(Br)C=O YTGSYRVSBPFKMQ-UHFFFAOYSA-N 0.000 abstract 1
- OXVISHZELPRKFQ-UHFFFAOYSA-N 2,2,3-trichlorobutanal Chemical compound CC(Cl)C(Cl)(Cl)C=O OXVISHZELPRKFQ-UHFFFAOYSA-N 0.000 abstract 1
- NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- HIOATCMWEPNLBT-UHFFFAOYSA-N C(CCC)C(=O)C(Cl)(Cl)Cl.O=CC(Cl)(Cl)Cl Chemical compound C(CCC)C(=O)C(Cl)(Cl)Cl.O=CC(Cl)(Cl)Cl HIOATCMWEPNLBT-UHFFFAOYSA-N 0.000 abstract 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- WBVHLCGBADRUBO-UHFFFAOYSA-N diethyl (2,3,4,5,6-pentachlorophenyl) phosphite Chemical compound P(OC1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)(OCC)OCC WBVHLCGBADRUBO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-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
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 235000013311 vegetables Nutrition 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0744360/IV(a)/1> in which R1 represents an alkyl residue, which residue may contain substituents, R2 represents an aryl residue, which may contain substituents, X and Y each represent -O- or =N-Alkyl, Z represents oxygen, R4 represents hydrogen, halogen or halogen-alkyl, R5 represents hydrogen, an alkoxy group, a substituted or unsubstituted alkyl or phenyl group or a dialkylamino group and Hal represents a halogen atom. Such compounds are obtained by reacting a compound of the general formula <FORM:0744360/IV(a)/2> in which R3 has the same meaning as R1 or R2 with a polyhalogeno-compound which contains in the a -position to a -CO- group more than one halogen atom and corresponds to the formula <FORM:0744360/IV(a)/3> a compound Hal-R3 being split off during the reaction. Aliphatic radicals which R1 and R3 may represent include straight and branched saturated and unsaturated radicals such as methyl, ethyl, propyl, isopropyl, butyl, hexyl, 2-ethyl-butyl, octyl, 2-butyl octyl, lauryl, octadecyl, allyl and 2-chloroethyl groups, and also radicals containing thiocyanic acid, cyano or ester groups. Aromatic radicals which R2 and R3 may represent may be mono- or polynuclear and include 2- or 4-chlorophenyl, 2:4-dichlorophenyl, 4-methoxyphenyl, 4-nitrophenyl, naphthyl and 4-diphenyl groups. As polyhalogeno-compounds of the above formula are specified aldehydes such as dichloracetaldehyde, butylchloral, bromal and chloral, ketones such as polyhalogen-methyl ketones, e.g. 1 : 1-dichloracetone, 1 : 1 : 3- or 1 : 1 : 1-trichloracetone, 1 : 1 : 3 : 3 - or 1 : 1 : 1 : 3 - tetrachloracetone, penta- or hexa-chloracetone, o -trichloroacetophenone, 4 - chloro - o - trichloracetophenone, 4 - methyl - o - trichloracetophenone, esters in which R5 represents an alkoxy group such as esters of halogenated acetic acid, especially of trichloracetic acid, and amides in which R5 represents the residue of a primary or secondary amine, e.g. trichloracetic acid dimethylamide. The reaction may be effected in a solvent. The products have animal and vegetable pest-combating properties. Examples describe the reaction of (1) p-chlorophenyl diethyl phosphite and chloral. Instead of chloral, 1 : 1 : 3 : 3 - tetrachloracetone can be used; (2) 2 : 4-dichlorophenyl diethyl phosphite and chloral. Instead of chloral butyl chloral or trichloracetic acid ethyl ester can be used; (3) chloral and diethyl (methyl-phenyl amido) phosphite (C6H5N(CH3).P(OC2H5)2); (4) pentachlorophenyl diethyl phosphite and chloral.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH744360X | 1951-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB744360A true GB744360A (en) | 1956-02-08 |
Family
ID=4533372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23482/52A Expired GB744360A (en) | 1951-09-25 | 1952-09-18 | Manufacture of organic compounds containing halogen and phosphorus |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB744360A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299190A (en) * | 1962-01-23 | 1967-01-17 | Bayer Ag | Omicron, omicron-dialkyl-omicron-dichlorovinyl phosphates |
| US3468909A (en) * | 1966-12-23 | 1969-09-23 | Mobil Oil Corp | 4-benzothienyl ethyl 2,2-dichlorovinyl phosphate pesticide |
| EP0126249A1 (en) * | 1983-04-12 | 1984-11-28 | Bayer Ag | Chlorinated phosphorylmethylcarbonyl derivatives, process for their preparation and their use in plant protecting agents |
| CN109761776A (en) * | 2018-12-29 | 2019-05-17 | 中国船舶重工集团公司第七一八研究所 | A kind of method of purification of hexachloroacetone |
-
1952
- 1952-09-18 GB GB23482/52A patent/GB744360A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299190A (en) * | 1962-01-23 | 1967-01-17 | Bayer Ag | Omicron, omicron-dialkyl-omicron-dichlorovinyl phosphates |
| US3468909A (en) * | 1966-12-23 | 1969-09-23 | Mobil Oil Corp | 4-benzothienyl ethyl 2,2-dichlorovinyl phosphate pesticide |
| EP0126249A1 (en) * | 1983-04-12 | 1984-11-28 | Bayer Ag | Chlorinated phosphorylmethylcarbonyl derivatives, process for their preparation and their use in plant protecting agents |
| US4541858A (en) * | 1983-04-12 | 1985-09-17 | Bayer Aktiengesellschaft | Chlorinated phosphorylmethylcarbonyl derivative plant protection agents |
| CN109761776A (en) * | 2018-12-29 | 2019-05-17 | 中国船舶重工集团公司第七一八研究所 | A kind of method of purification of hexachloroacetone |
| CN109761776B (en) * | 2018-12-29 | 2022-01-21 | 中国船舶重工集团公司第七一八研究所 | Purification method of hexachloroacetone |
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