GB1038611A - Thiophosphoric acid esters containing sulphonyl groups - Google Patents
Thiophosphoric acid esters containing sulphonyl groupsInfo
- Publication number
- GB1038611A GB1038611A GB4003961A GB4003961A GB1038611A GB 1038611 A GB1038611 A GB 1038611A GB 4003961 A GB4003961 A GB 4003961A GB 4003961 A GB4003961 A GB 4003961A GB 1038611 A GB1038611 A GB 1038611A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- compound
- pbr3
- nitro
- benzene
- 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
- -1 sulphonyl groups Chemical group 0.000 title abstract 6
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 229910020667 PBr3 Inorganic materials 0.000 abstract 6
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 2
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 abstract 2
- GYPDHLDQINBFPY-UHFFFAOYSA-N 4-thiophen-3-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CSC=C1 GYPDHLDQINBFPY-UHFFFAOYSA-N 0.000 abstract 2
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 abstract 1
- AOQYAMDZQAEDLO-UHFFFAOYSA-N 4-chlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC=C(Cl)C=C1 AOQYAMDZQAEDLO-UHFFFAOYSA-N 0.000 abstract 1
- FXJVNINSOKCNJP-UHFFFAOYSA-N 4-methylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-N 0.000 abstract 1
- VTILWYBQQRECER-UHFFFAOYSA-N 5-sulfonylcyclohexa-1,3-diene Chemical compound O=S(=O)=C1CC=CC=C1 VTILWYBQQRECER-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- SNZXFRFQGXSSGN-UHFFFAOYSA-N phenylsulfanyloxysulfanylbenzene Chemical compound C=1C=CC=CC=1SOSC1=CC=CC=C1 SNZXFRFQGXSSGN-UHFFFAOYSA-N 0.000 abstract 1
- BBSWINSMWHMQRQ-UHFFFAOYSA-M sodium;2-chloro-5-nitrobenzenesulfinate Chemical compound [Na+].[O-][N+](=O)C1=CC=C(Cl)C(S([O-])=O)=C1 BBSWINSMWHMQRQ-UHFFFAOYSA-M 0.000 abstract 1
- FJSOUHVHPWODGS-UHFFFAOYSA-M sodium;4-bromobenzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=C(Br)C=C1 FJSOUHVHPWODGS-UHFFFAOYSA-M 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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 having the general formula S = P(OR1)(OR2)S.Z.SO2R3 wherein R1 and R2 are the same or different and each is a C1-C4 alkyl group, R3 is a phenyl group substituted by at least one substituent selected from halogen (e.g. Cl or Br), nitro and C1-C4 alkyl, and Z is a saturated straight or branched chain divalent aliphatic hydrocarbon group containing at least two carbon atoms and which may be interrupted by one or more oxygen or sulphur atoms. They may be obtained by reacting a compound of the formula S = P(OR1)(OR2)S.Z.SO2R2 where M is alkali metal or ammonium with a compound of the formula Hal.Z.SO2R3 in which Hal is a halogen atom e.g. Cl or Br. The reaction is suitably effected in an inert organic solvent e.g. an ester or ketone, at elevated temperature e.g. at or about the boiling point of the solvent. The products have pesticidal properties (see Division A5). The compounds Hal.Z.SO2R3 may be obtained by reacting HO.Z.SO2R3 with a halogenating agent e.g. PBr3 or thionyl chloride. 1 - nitro - 4 - (21 - hydroxyethyl) phenyl thioether is obtained by reacting ethylene chlorhydrin with p-nitrothiophenol and may be reacted with PBr3 to form 1 - nitro - 4 - (21-bromethyl) - phenyl thioether which may be oxidized to the corresponding sulphonyl compound by means of H2O2 and acetic acid. 1-Chloro - 4 (21 - hydroxypropylsulphonyl) benzene is obtained by reacting propylene oxide or propylene chlorhydrin with p-chlorobenzene sulphinic acid or by oxidation of the corresponding sulphide with H2O2 and acetic acid and may be reacted with PBr3 to form the corresponding 2-bromopropyl compound. b -Chloro - ethoxyethyl - 4 - nitrophenyl sulphone is obtained by reacting di-(2-chloroethyl) ether with the sodium salt of p-nitrothiophenol. 1-Chloro - 4 - nitro - 2 - (21 - chloroethoxyethyl) sulphonyl benzene is obtained by reacting di(2-chloroethyl) ether on sodium 2-chloro-5-nitro-benzene sulphinate. 1-Methyl-4-(21-chloroethyl-sulphonyl) benzene is obtained by the action of SOCl2 in CHCL3 on the corresponding 21-hydroxy ethyl compound which may be obtained by the reaction of ethylene oxide or ethylene chlorhydrin on p-toluene sulphinic acid. 1-Chloro - 4 - (21 - bromoethylsulphonyl) - benzene is prepared by (a) reacting PBr3 with the corresponding 21 hydroxyethyl compound which is prepared by reacting ethylene oxide with p-chlorobenzene sulphinic acid; or (b) by the action of ethylene oxide on the sodium salt of 4-chlorobenzene sulphinic acid and then treating with PBr3. 1 - Bromo - 4 - (21 - bromoethyl-sulphonyl)-benzene may be obtained similarly by reacting ethylene oxide with sodium 4-bromobenzene sulphinate and then treating with PBr3.ALSO:A pesticidal composition comprises a carrier or solvent and a compound of the formula: S = P (OR1) (OR2) S. Z. SO2R3 wherein R1 and R2 are C1-C4 alkyl groups, R3 is a phenyl group substituted by at least one substituent selected from halogen (e.g. Cl or Br), nitro, and C1-C4 alkyl and Z is a saturated straight or branched chain divalent aliphatic hydrocarbon group containing at least 2 carbon atoms and which may be interrupted by one or more O or S atoms. The carrier may be solid or liquid.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4003961A GB1038611A (en) | 1961-11-08 | 1961-11-08 | Thiophosphoric acid esters containing sulphonyl groups |
| FR914624A FR1450373A (en) | 1961-11-08 | 1962-11-07 | New pesticide compounds and their preparation process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4003961A GB1038611A (en) | 1961-11-08 | 1961-11-08 | Thiophosphoric acid esters containing sulphonyl groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1038611A true GB1038611A (en) | 1966-08-10 |
Family
ID=10412861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4003961A Expired GB1038611A (en) | 1961-11-08 | 1961-11-08 | Thiophosphoric acid esters containing sulphonyl groups |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1038611A (en) |
-
1961
- 1961-11-08 GB GB4003961A patent/GB1038611A/en not_active Expired
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