CS208496B2 - Herbicide means and method of making the active substances thereof - Google Patents
Herbicide means and method of making the active substances thereof Download PDFInfo
- Publication number
- CS208496B2 CS208496B2 CS792337A CS233779A CS208496B2 CS 208496 B2 CS208496 B2 CS 208496B2 CS 792337 A CS792337 A CS 792337A CS 233779 A CS233779 A CS 233779A CS 208496 B2 CS208496 B2 CS 208496B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carbon atoms
- formula
- compound
- group containing
- present
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 18
- 239000004009 herbicide Substances 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000013543 active substance Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 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 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 8
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- -1 ethoxy, butoxy, methoxyethyl Chemical group 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 3
- 125000004490 chloroalkoxy group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 240000000260 Typha latifolia Species 0.000 claims 1
- 125000006011 chloroethoxy group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 239000002671 adjuvant Substances 0.000 abstract description 4
- 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 abstract description 3
- 239000000969 carrier Substances 0.000 abstract description 2
- 239000003085 diluting agent Substances 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical class FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 description 1
- JTXKZMGARKMLQL-UHFFFAOYSA-N 2-[ethyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(CC)CP(O)(O)=O JTXKZMGARKMLQL-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 208000003643 Callosities Diseases 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 101150082208 DIABLO gene Proteins 0.000 description 1
- 102100033189 Diablo IAP-binding mitochondrial protein Human genes 0.000 description 1
- 241001462977 Elina Species 0.000 description 1
- 206010056474 Erythrosis Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000060234 Gmelina philippensis Species 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000015107 ale Nutrition 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 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
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229940047135 glycate Drugs 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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 |
|---|---|
| CS208496B2 true CS208496B2 (en) | 1981-09-15 |
Family
ID=25402560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS792337A CS208496B2 (en) | 1978-04-06 | 1979-04-05 | Herbicide means and method of making the active substances thereof |
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) | DD147112A5 (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) | RO77976B (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 EP EP79300555A patent/EP0005321B1/en not_active Expired
- 1979-04-04 ES ES479305A patent/ES479305A1/es not_active Expired
- 1979-04-04 DE DE7979300555T patent/DE2962495D1/de not_active Expired
- 1979-04-05 AR AR276078A patent/AR219587A1/es active
- 1979-04-05 ZA ZA791631A patent/ZA791631B/xx unknown
- 1979-04-05 CA CA000324992A patent/CA1134383A/en not_active Expired
- 1979-04-05 CS CS792337A patent/CS208496B2/cs unknown
- 1979-04-05 BG BG7943137A patent/BG29270A3/xx unknown
- 1979-04-05 DD DD79216616A patent/DD147112A5/de unknown
- 1979-04-05 IT IT7921624A patent/IT1112954B/it active
- 1979-04-05 DD DD79212039A patent/DD143554A5/de unknown
- 1979-04-05 SU SU792749004A patent/SU1220560A3/ru active
- 1979-04-05 DK DK140179A patent/DK147578C/da active
- 1979-04-05 PH PH22353A patent/PH14617A/en unknown
- 1979-04-05 IL IL57017A patent/IL57017A/xx unknown
- 1979-04-05 JP JP4190579A patent/JPS54135725A/ja active Pending
- 1979-04-05 RO RO97135A patent/RO77976B/ro unknown
- 1979-04-05 PL PL1979214707A patent/PL114130B1/pl unknown
- 1979-04-05 BR BR7902086A patent/BR7902086A/pt unknown
- 1979-04-05 RO RO107609A patent/RO84500B/ro unknown
- 1979-04-05 AU AU45850/79A patent/AU518313B2/en not_active Ceased
- 1979-04-05 HU HU79MO1041A patent/HU185005B/hu unknown
- 1979-04-06 YU YU826/79A patent/YU41153B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO77976B (ro) | 1985-01-30 |
| RO84500A (ro) | 1984-09-29 |
| DK140179A (da) | 1979-10-07 |
| RO84500B (ro) | 1984-10-30 |
| IL57017A (en) | 1982-12-31 |
| SU1220560A3 (ru) | 1986-03-23 |
| DK147578C (da) | 1985-03-18 |
| AU518313B2 (en) | 1981-09-24 |
| YU41153B (en) | 1986-12-31 |
| PL214707A1 (pl) | 1979-12-17 |
| PL114130B1 (en) | 1981-01-31 |
| ES479305A1 (es) | 1980-01-01 |
| EP0005321B1 (en) | 1982-04-14 |
| EP0005321A1 (en) | 1979-11-14 |
| IT7921624A0 (it) | 1979-04-05 |
| PH14617A (en) | 1981-10-12 |
| AR219587A1 (es) | 1980-08-29 |
| IT1112954B (it) | 1986-01-20 |
| YU82679A (en) | 1983-12-31 |
| DE2962495D1 (en) | 1982-05-27 |
| DD143554A5 (de) | 1980-09-03 |
| BR7902086A (pt) | 1979-11-27 |
| BG29270A3 (en) | 1980-10-15 |
| AU4585079A (en) | 1979-10-11 |
| IL57017A0 (en) | 1979-07-25 |
| JPS54135725A (en) | 1979-10-22 |
| RO77976A (ro) | 1984-01-14 |
| CA1134383A (en) | 1982-10-26 |
| DD147112A5 (de) | 1981-03-18 |
| ZA791631B (en) | 1980-04-30 |
| DK147578B (da) | 1984-10-08 |
| HU185005B (en) | 1984-11-28 |
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