DD147112A5 - Verfahren zur herstellung von n-trifluoracetyl-n-phosphonomethylglycin-dichlorid-derivaten - Google Patents
Verfahren zur herstellung von n-trifluoracetyl-n-phosphonomethylglycin-dichlorid-derivaten Download PDFInfo
- Publication number
- DD147112A5 DD147112A5 DD79216616A DD21661679A DD147112A5 DD 147112 A5 DD147112 A5 DD 147112A5 DD 79216616 A DD79216616 A DD 79216616A DD 21661679 A DD21661679 A DD 21661679A DD 147112 A5 DD147112 A5 DD 147112A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- carbon atoms
- group
- alkoxy group
- formula
- thionyl chloride
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 28
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- -1 methoxyethoxy, methoxypropoxy, methoxybutoxy, ethoxyethoxy, ethoxypropoxy, propoxyethoxy, propoxypropoxy Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007705 chemical test Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- OKJWOMOTIACMHK-UHFFFAOYSA-N 2-[dichlorooxyphosphorylmethyl-(2,2,2-trifluoroacetyl)amino]acetic acid Chemical compound OC(=O)CN(C(=O)C(F)(F)F)CP(=O)(OCl)OCl OKJWOMOTIACMHK-UHFFFAOYSA-N 0.000 description 1
- NPNBMYIARMQHND-UHFFFAOYSA-N 2-[ethyl(phosphono)amino]acetic acid Chemical class C(C)N(CC(=O)O)P(=O)(O)O NPNBMYIARMQHND-UHFFFAOYSA-N 0.000 description 1
- MKJBZNABCZRVPC-UHFFFAOYSA-N 2-[phosphonomethyl-(2,2,2-trifluoroacetyl)amino]acetic acid Chemical compound OC(=O)CN(CP(O)(O)=O)C(=O)C(F)(F)F MKJBZNABCZRVPC-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241001148727 Bromus tectorum Species 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 240000001579 Cirsium arvense Species 0.000 description 1
- 235000005918 Cirsium arvense Nutrition 0.000 description 1
- 244000285774 Cyperus esculentus Species 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001289540 Fallopia convolvulus Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000209072 Sorghum Species 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241001506766 Xanthium Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil Substances 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
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A01N57/34—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-halogen bonds; Phosphonium salts
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89407078A | 1978-04-06 | 1978-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD147112A5 true DD147112A5 (de) | 1981-03-18 |
Family
ID=25402560
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79212039A DD143554A5 (de) | 1978-04-06 | 1979-04-05 | Herbizide zusammensetzung |
| DD79216616A DD147112A5 (de) | 1978-04-06 | 1979-04-05 | Verfahren zur herstellung von n-trifluoracetyl-n-phosphonomethylglycin-dichlorid-derivaten |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79212039A DD143554A5 (de) | 1978-04-06 | 1979-04-05 | Herbizide zusammensetzung |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0005321B1 (ro) |
| JP (1) | JPS54135725A (ro) |
| AR (1) | AR219587A1 (ro) |
| AU (1) | AU518313B2 (ro) |
| BG (1) | BG29270A3 (ro) |
| BR (1) | BR7902086A (ro) |
| CA (1) | CA1134383A (ro) |
| CS (1) | CS208496B2 (ro) |
| DD (2) | DD143554A5 (ro) |
| DE (1) | DE2962495D1 (ro) |
| DK (1) | DK147578C (ro) |
| ES (1) | ES479305A1 (ro) |
| HU (1) | HU185005B (ro) |
| IL (1) | IL57017A (ro) |
| IT (1) | IT1112954B (ro) |
| PH (1) | PH14617A (ro) |
| PL (1) | PL114130B1 (ro) |
| RO (2) | RO84500B (ro) |
| SU (1) | SU1220560A3 (ro) |
| YU (1) | YU41153B (ro) |
| ZA (1) | ZA791631B (ro) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853530A (en) * | 1971-03-10 | 1974-12-10 | Monsanto Co | Regulating plants with n-phosphonomethylglycine and derivatives thereof |
| PH16509A (en) * | 1971-03-10 | 1983-11-08 | Monsanto Co | N-phosphonomethylglycine phytotoxicant composition |
| US3970695A (en) * | 1975-05-23 | 1976-07-20 | Monsanto Company | N-(perfluoroacyl)-N-phosphonomethyl glycine compounds, method of preparing same |
-
1979
- 1979-04-04 ES ES479305A patent/ES479305A1/es not_active Expired
- 1979-04-04 DE DE7979300555T patent/DE2962495D1/de not_active Expired
- 1979-04-04 EP EP79300555A patent/EP0005321B1/en not_active Expired
- 1979-04-05 ZA ZA791631A patent/ZA791631B/xx unknown
- 1979-04-05 CA CA000324992A patent/CA1134383A/en not_active Expired
- 1979-04-05 AR AR276078A patent/AR219587A1/es active
- 1979-04-05 IT IT7921624A patent/IT1112954B/it active
- 1979-04-05 BG BG7943137A patent/BG29270A3/xx unknown
- 1979-04-05 BR BR7902086A patent/BR7902086A/pt unknown
- 1979-04-05 DK DK140179A patent/DK147578C/da active
- 1979-04-05 IL IL57017A patent/IL57017A/xx unknown
- 1979-04-05 DD DD79212039A patent/DD143554A5/de unknown
- 1979-04-05 JP JP4190579A patent/JPS54135725A/ja active Pending
- 1979-04-05 SU SU792749004A patent/SU1220560A3/ru active
- 1979-04-05 PH PH22353A patent/PH14617A/en unknown
- 1979-04-05 HU HU79MO1041A patent/HU185005B/hu unknown
- 1979-04-05 AU AU45850/79A patent/AU518313B2/en not_active Ceased
- 1979-04-05 PL PL1979214707A patent/PL114130B1/pl unknown
- 1979-04-05 RO RO107609A patent/RO84500B/ro unknown
- 1979-04-05 RO RO97135A patent/RO77976B/ro unknown
- 1979-04-05 CS CS792337A patent/CS208496B2/cs unknown
- 1979-04-05 DD DD79216616A patent/DD147112A5/de unknown
- 1979-04-06 YU YU826/79A patent/YU41153B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL57017A0 (en) | 1979-07-25 |
| IL57017A (en) | 1982-12-31 |
| IT7921624A0 (it) | 1979-04-05 |
| EP0005321A1 (en) | 1979-11-14 |
| RO77976B (ro) | 1985-01-30 |
| CA1134383A (en) | 1982-10-26 |
| SU1220560A3 (ru) | 1986-03-23 |
| ZA791631B (en) | 1980-04-30 |
| PL114130B1 (en) | 1981-01-31 |
| DK147578C (da) | 1985-03-18 |
| BR7902086A (pt) | 1979-11-27 |
| EP0005321B1 (en) | 1982-04-14 |
| IT1112954B (it) | 1986-01-20 |
| HU185005B (en) | 1984-11-28 |
| PH14617A (en) | 1981-10-12 |
| JPS54135725A (en) | 1979-10-22 |
| YU41153B (en) | 1986-12-31 |
| RO77976A (ro) | 1984-01-14 |
| DK147578B (da) | 1984-10-08 |
| PL214707A1 (pl) | 1979-12-17 |
| AU4585079A (en) | 1979-10-11 |
| DE2962495D1 (en) | 1982-05-27 |
| DK140179A (da) | 1979-10-07 |
| CS208496B2 (en) | 1981-09-15 |
| AU518313B2 (en) | 1981-09-24 |
| DD143554A5 (de) | 1980-09-03 |
| AR219587A1 (es) | 1980-08-29 |
| YU82679A (en) | 1983-12-31 |
| RO84500A (ro) | 1984-09-29 |
| RO84500B (ro) | 1984-10-30 |
| ES479305A1 (es) | 1980-01-01 |
| BG29270A3 (en) | 1980-10-15 |
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