DD153845A5 - Verfahren zur herstellung unsymmetrischer thiophosphonatverbindungen - Google Patents
Verfahren zur herstellung unsymmetrischer thiophosphonatverbindungen Download PDFInfo
- Publication number
- DD153845A5 DD153845A5 DD80223616A DD22361680A DD153845A5 DD 153845 A5 DD153845 A5 DD 153845A5 DD 80223616 A DD80223616 A DD 80223616A DD 22361680 A DD22361680 A DD 22361680A DD 153845 A5 DD153845 A5 DD 153845A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- items
- alkyl
- ethyl
- carbon atoms
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 235000013339 cereals Nutrition 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000000361 pesticidal effect Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- 241000244206 Nematoda Species 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 12
- 239000002917 insecticide Substances 0.000 abstract description 5
- 230000001069 nematicidal effect Effects 0.000 abstract description 5
- 239000005645 nematicide Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 13
- -1 butylethylphosphonodithiochloride Chemical compound 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 231100000674 Phytotoxicity Toxicity 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 230000000007 visual effect Effects 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
-
- 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)]
- C07F9/42—Halides thereof
- C07F9/425—Acid or estermonohalides thereof, e.g. RP(=X)(YR)(Hal) (X, Y = O, S; R = H, or hydrocarbon group)
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon 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
- C07F9/28—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)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/071,464 US4258038A (en) | 1979-08-31 | 1979-08-31 | Unsymmetrical thiophosphonate insecticides and nematocides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD153845A5 true DD153845A5 (de) | 1982-02-03 |
Family
ID=22101498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80223616A DD153845A5 (de) | 1979-08-31 | 1980-08-29 | Verfahren zur herstellung unsymmetrischer thiophosphonatverbindungen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4258038A (es) |
| EP (1) | EP0024830B1 (es) |
| JP (1) | JPS5643292A (es) |
| KR (1) | KR840000891B1 (es) |
| AR (1) | AR231988A1 (es) |
| AT (1) | ATE4987T1 (es) |
| AU (1) | AU541988B2 (es) |
| BR (1) | BR8005508A (es) |
| DD (1) | DD153845A5 (es) |
| DE (1) | DE3065284D1 (es) |
| DK (1) | DK369880A (es) |
| EG (1) | EG14432A (es) |
| ES (1) | ES8105741A1 (es) |
| HU (1) | HU184822B (es) |
| IL (1) | IL60892A (es) |
| ZA (1) | ZA805026B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450158A (en) * | 1982-05-13 | 1984-05-22 | Fmc Corporation | S-Tertiary alkyl phosphoroamidodithioate pesticides |
| EP0118109A1 (en) * | 1983-03-04 | 1984-09-12 | Stauffer Chemical Company | Trithiophosphonate insecticides, particularly for use in soil |
| GR850923B (es) * | 1984-04-16 | 1985-11-25 | Stauffer Chemical Co | |
| US4565809A (en) * | 1984-06-04 | 1986-01-21 | Stauffer Chemical Co. | S-Aralkyltrithiophosphonate insecticides |
| US4678778A (en) * | 1985-02-25 | 1987-07-07 | Stauffer Chemical Company | Trithiophosphonate insecticides |
| US4752604A (en) * | 1985-07-29 | 1988-06-21 | Stauffer Chemical Company | S,S-di-(tertiary alkyl) thiophosphonate insecticides |
| AU6963387A (en) * | 1986-03-10 | 1987-09-17 | Sumitomo Chemical Company, Limited | Trithiophosphonic acid esters |
| US4837209A (en) * | 1987-07-06 | 1989-06-06 | Stauffer Chemical Company | S-cycloalkylmethyl trithiophosphonate insecticides |
| US6153551A (en) * | 1997-07-14 | 2000-11-28 | Mobil Oil Corporation | Preparation of supported catalyst using trialkylaluminum-metallocene contact products |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1145615B (de) * | 1959-09-26 | 1963-03-21 | Bayer Ag | Verfahren zur Herstellung von Trithiophosphonsaeureestern |
| BE608802A (es) * | 1960-10-05 | |||
| US3162570A (en) * | 1962-05-21 | 1964-12-22 | Socony Mobil Oil Co Inc | Organophosphorus compounds as insecticides and nematocides |
| US3705216A (en) * | 1969-12-22 | 1972-12-05 | American Cyanamid Co | Preparation of trivalent and pentavalent thioesters of phosphorus |
-
1979
- 1979-08-31 US US06/071,464 patent/US4258038A/en not_active Expired - Lifetime
-
1980
- 1980-08-04 EP EP80302648A patent/EP0024830B1/en not_active Expired
- 1980-08-04 AT AT80302648T patent/ATE4987T1/de not_active IP Right Cessation
- 1980-08-04 DE DE8080302648T patent/DE3065284D1/de not_active Expired
- 1980-08-15 AU AU61496/80A patent/AU541988B2/en not_active Ceased
- 1980-08-15 ZA ZA00805026A patent/ZA805026B/xx unknown
- 1980-08-21 IL IL60892A patent/IL60892A/xx unknown
- 1980-08-27 EG EG528/80A patent/EG14432A/xx active
- 1980-08-27 KR KR1019800003397A patent/KR840000891B1/ko not_active Expired
- 1980-08-29 DK DK369880A patent/DK369880A/da not_active Application Discontinuation
- 1980-08-29 ES ES494629A patent/ES8105741A1/es not_active Expired
- 1980-08-29 DD DD80223616A patent/DD153845A5/de unknown
- 1980-08-29 HU HU802141A patent/HU184822B/hu unknown
- 1980-08-29 BR BR8005508A patent/BR8005508A/pt unknown
- 1980-08-29 AR AR282366A patent/AR231988A1/es active
- 1980-09-01 JP JP12099880A patent/JPS5643292A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4258038A (en) | 1981-03-24 |
| KR830003508A (ko) | 1983-06-21 |
| ES494629A0 (es) | 1981-06-16 |
| HU184822B (en) | 1984-10-29 |
| IL60892A (en) | 1984-05-31 |
| AR231988A1 (es) | 1985-04-30 |
| EG14432A (en) | 1984-03-31 |
| AU541988B2 (en) | 1985-01-31 |
| EP0024830B1 (en) | 1983-10-12 |
| ATE4987T1 (de) | 1983-10-15 |
| AU6149680A (en) | 1982-03-11 |
| DE3065284D1 (en) | 1983-11-17 |
| JPS5643292A (en) | 1981-04-21 |
| DK369880A (da) | 1981-03-01 |
| ES8105741A1 (es) | 1981-06-16 |
| IL60892A0 (en) | 1980-10-26 |
| BR8005508A (pt) | 1981-03-10 |
| ZA805026B (en) | 1981-08-26 |
| EP0024830A1 (en) | 1981-03-11 |
| KR840000891B1 (ko) | 1984-06-26 |
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