DE1103324B - Verfahren zur Herstellung von Sulfenylthiophosphorsaeureestern bzw.-thiophosphonsaeureestern - Google Patents
Verfahren zur Herstellung von Sulfenylthiophosphorsaeureestern bzw.-thiophosphonsaeureesternInfo
- Publication number
- DE1103324B DE1103324B DEF29652A DEF0029652A DE1103324B DE 1103324 B DE1103324 B DE 1103324B DE F29652 A DEF29652 A DE F29652A DE F0029652 A DEF0029652 A DE F0029652A DE 1103324 B DE1103324 B DE 1103324B
- Authority
- DE
- Germany
- Prior art keywords
- mol
- acid esters
- acid
- yield
- theory
- 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.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims description 18
- 239000002253 acid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 5
- -1 araliphatic Chemical group 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 23
- 229910052698 phosphorus Inorganic materials 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- 241000700159 Rattus Species 0.000 description 10
- 206010058667 Oral toxicity Diseases 0.000 description 9
- 231100000418 oral toxicity Toxicity 0.000 description 9
- 241001124076 Aphididae Species 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWGZRLZJBLEVFZ-UHFFFAOYSA-N 1-nitro-4-[(4-nitrophenyl)disulfanyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1SSC1=CC=C([N+]([O-])=O)C=C1 KWGZRLZJBLEVFZ-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 3
- NCBOVAWEMBIIFK-UHFFFAOYSA-N (4-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=C(SCl)C=C1 NCBOVAWEMBIIFK-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 description 1
- NXCKJENHTITELM-UHFFFAOYSA-N 1-nitro-2-[(2-nitrophenyl)disulfanyl]benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1SSC1=CC=CC=C1[N+]([O-])=O NXCKJENHTITELM-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YJVOECXUWYQORY-UHFFFAOYSA-N dihydroxy-methylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CSP(O)(O)=S YJVOECXUWYQORY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZUNFAOLVHKUWCL-UHFFFAOYSA-N dipropoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCOP(S)(=S)OCCC ZUNFAOLVHKUWCL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UHMZHYUCMREDRI-UHFFFAOYSA-N ethyl thiohypochlorite Chemical compound CCSCl UHMZHYUCMREDRI-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/409—Compounds containing the structure P(=X)-X-acyl, P(=X) -X-heteroatom, P(=X)-X-CN (X = O, S, Se)
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing aromatic 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1655—Compounds containing the structure P(=X)n-S-(S)x- (X = O, S, Se; n=0,1; x>=1)
-
- 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
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL257078D NL257078A (US06262066-20010717-C00422.png) | 1959-10-20 | ||
| BE596202D BE596202A (US06262066-20010717-C00422.png) | 1959-10-20 | ||
| IT649708D IT649708A (US06262066-20010717-C00422.png) | 1959-10-20 | ||
| DEF29652A DE1103324B (de) | 1959-10-20 | 1959-10-20 | Verfahren zur Herstellung von Sulfenylthiophosphorsaeureestern bzw.-thiophosphonsaeureestern |
| CH1152860A CH387019A (de) | 1959-10-20 | 1960-10-13 | Verfahren zur Herstellung von Sulfenyl-phosphorthioaten |
| GB3588160A GB909325A (en) | 1959-10-20 | 1960-10-19 | Aromatic sulphenyl-phosphorus thioates and process for their production |
| FR841755A FR1272706A (fr) | 1959-10-20 | 1960-10-20 | Procédé de préparation de sulfényl-phosphothioates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29652A DE1103324B (de) | 1959-10-20 | 1959-10-20 | Verfahren zur Herstellung von Sulfenylthiophosphorsaeureestern bzw.-thiophosphonsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1103324B true DE1103324B (de) | 1961-03-30 |
Family
ID=7093406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF29652A Pending DE1103324B (de) | 1959-10-20 | 1959-10-20 | Verfahren zur Herstellung von Sulfenylthiophosphorsaeureestern bzw.-thiophosphonsaeureestern |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199762B (de) * | 1961-07-12 | 1965-09-02 | R I A F Societa Azionaria Roma | Verfahren zur Herstellung von nematocid wirksamen Dithiophosphorsaeureestern |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE817753C (de) * | 1949-07-10 | 1951-10-18 | Bayer Ag | Verfahren zur Herstellung von S-Nitrophenyl-0, 0-dialkylthiophosphaten |
| DE1046062B (de) * | 1957-03-01 | 1958-12-11 | Bayer Ag | Verfahren zur Herstellung von insecticid wirksamen Dialkyl-thionothiolphosphorsaeureestern |
-
0
- IT IT649708D patent/IT649708A/it unknown
- NL NL257078D patent/NL257078A/xx unknown
- BE BE596202D patent/BE596202A/xx unknown
-
1959
- 1959-10-20 DE DEF29652A patent/DE1103324B/de active Pending
-
1960
- 1960-10-13 CH CH1152860A patent/CH387019A/de unknown
- 1960-10-19 GB GB3588160A patent/GB909325A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE817753C (de) * | 1949-07-10 | 1951-10-18 | Bayer Ag | Verfahren zur Herstellung von S-Nitrophenyl-0, 0-dialkylthiophosphaten |
| DE1046062B (de) * | 1957-03-01 | 1958-12-11 | Bayer Ag | Verfahren zur Herstellung von insecticid wirksamen Dialkyl-thionothiolphosphorsaeureestern |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199762B (de) * | 1961-07-12 | 1965-09-02 | R I A F Societa Azionaria Roma | Verfahren zur Herstellung von nematocid wirksamen Dithiophosphorsaeureestern |
Also Published As
| Publication number | Publication date |
|---|---|
| BE596202A (US06262066-20010717-C00422.png) | |
| CH387019A (de) | 1965-01-31 |
| NL257078A (US06262066-20010717-C00422.png) | |
| IT649708A (US06262066-20010717-C00422.png) | |
| GB909325A (en) | 1962-10-31 |
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