JPS6169751A - サリチルアミド誘導体、その製法及び十字科植物の根こぶ病防除剤 - Google Patents
サリチルアミド誘導体、その製法及び十字科植物の根こぶ病防除剤Info
- Publication number
- JPS6169751A JPS6169751A JP59190605A JP19060584A JPS6169751A JP S6169751 A JPS6169751 A JP S6169751A JP 59190605 A JP59190605 A JP 59190605A JP 19060584 A JP19060584 A JP 19060584A JP S6169751 A JPS6169751 A JP S6169751A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- salicylamide
- general formula
- agent
- 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
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 229960000581 salicylamide Drugs 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 27
- 239000003795 chemical substances by application Substances 0.000 abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 231100000674 Phytotoxicity Toxicity 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- -1 salicylamide compound Chemical class 0.000 description 24
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 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 2
- 239000005909 Kieselgur Substances 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59190605A JPS6169751A (ja) | 1984-09-13 | 1984-09-13 | サリチルアミド誘導体、その製法及び十字科植物の根こぶ病防除剤 |
EP85111079A EP0174584A3 (de) | 1984-09-13 | 1985-09-03 | Salicylamid-Derivate |
US06/774,272 US4708953A (en) | 1984-09-13 | 1985-09-10 | Salicylamide derivatives |
IL76352A IL76352A0 (en) | 1984-09-13 | 1985-09-10 | Salicylamide derivatives,their preparation and their use as fungicides |
KR1019850006634A KR860002454A (ko) | 1984-09-13 | 1985-09-11 | 살리실아미드 유도체의 제조방법 |
GR852203A GR852203B (en, 2012) | 1984-09-13 | 1985-09-11 | |
ZA856990A ZA856990B (en) | 1984-09-13 | 1985-09-12 | Salicylamide derivatives,a process for the preparation thereof and their use as controlling agents against club root of cruciferous plant |
BR8504405A BR8504405A (pt) | 1984-09-13 | 1985-09-12 | Processo para preparacao de derivados de salicilamida,composicoes fungicidas,processo para combater fungos,aplicacao de tais derivados,e processo para preparacao de tais composicoes |
ES546923A ES8604757A1 (es) | 1984-09-13 | 1985-09-12 | Procedimiento para la obtencion de derivados de salicilamida |
DK415785A DK415785A (da) | 1984-09-13 | 1985-09-12 | Salicylamid-derivater, deres fremstilling og anvendelse som fungicider |
HU853469A HU194152B (en) | 1984-09-13 | 1985-09-13 | Fungicide compositions containing salicylic amide derivatives as active substances and process for preparing the salicylic amide derivatives |
AU47470/85A AU573033B2 (en) | 1984-09-13 | 1985-09-13 | N-substituted salicylamides and their use as fungicides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59190605A JPS6169751A (ja) | 1984-09-13 | 1984-09-13 | サリチルアミド誘導体、その製法及び十字科植物の根こぶ病防除剤 |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6169751A true JPS6169751A (ja) | 1986-04-10 |
Family
ID=16260847
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59190605A Pending JPS6169751A (ja) | 1984-09-13 | 1984-09-13 | サリチルアミド誘導体、その製法及び十字科植物の根こぶ病防除剤 |
Country Status (12)
Country | Link |
---|---|
US (1) | US4708953A (en, 2012) |
EP (1) | EP0174584A3 (en, 2012) |
JP (1) | JPS6169751A (en, 2012) |
KR (1) | KR860002454A (en, 2012) |
AU (1) | AU573033B2 (en, 2012) |
BR (1) | BR8504405A (en, 2012) |
DK (1) | DK415785A (en, 2012) |
ES (1) | ES8604757A1 (en, 2012) |
GR (1) | GR852203B (en, 2012) |
HU (1) | HU194152B (en, 2012) |
IL (1) | IL76352A0 (en, 2012) |
ZA (1) | ZA856990B (en, 2012) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019230776A1 (ja) * | 2018-05-30 | 2019-12-05 | 株式会社アクアソリューション | 根こぶ病の抑制方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9520491D0 (en) * | 1995-10-07 | 1995-12-13 | Zeneca Ltd | Compounds |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE532448A (en, 2012) * | 1953-10-12 | |||
JPS5439040A (en) * | 1977-09-01 | 1979-03-24 | Nippon Kayaku Co Ltd | Novel 2-hydroxybenzamide derivatives and bactericides for the soil |
JPS5635662A (en) * | 1979-08-29 | 1981-04-08 | Toshiba Corp | Variable number of pole type rotary electric machine |
-
1984
- 1984-09-13 JP JP59190605A patent/JPS6169751A/ja active Pending
-
1985
- 1985-09-03 EP EP85111079A patent/EP0174584A3/de not_active Withdrawn
- 1985-09-10 US US06/774,272 patent/US4708953A/en not_active Expired - Fee Related
- 1985-09-10 IL IL76352A patent/IL76352A0/xx unknown
- 1985-09-11 GR GR852203A patent/GR852203B/el unknown
- 1985-09-11 KR KR1019850006634A patent/KR860002454A/ko not_active Withdrawn
- 1985-09-12 BR BR8504405A patent/BR8504405A/pt unknown
- 1985-09-12 ES ES546923A patent/ES8604757A1/es not_active Expired
- 1985-09-12 ZA ZA856990A patent/ZA856990B/xx unknown
- 1985-09-12 DK DK415785A patent/DK415785A/da not_active Application Discontinuation
- 1985-09-13 AU AU47470/85A patent/AU573033B2/en not_active Expired - Fee Related
- 1985-09-13 HU HU853469A patent/HU194152B/hu unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019230776A1 (ja) * | 2018-05-30 | 2019-12-05 | 株式会社アクアソリューション | 根こぶ病の抑制方法 |
JPWO2019230776A1 (ja) * | 2018-05-30 | 2021-08-26 | 株式会社アクアソリューション | 根こぶ病の抑制方法 |
Also Published As
Publication number | Publication date |
---|---|
HU194152B (en) | 1988-01-28 |
HUT39143A (en) | 1986-08-28 |
ES546923A0 (es) | 1986-02-16 |
DK415785D0 (da) | 1985-09-12 |
IL76352A0 (en) | 1986-01-31 |
DK415785A (da) | 1986-03-14 |
AU573033B2 (en) | 1988-05-26 |
ES8604757A1 (es) | 1986-02-16 |
GR852203B (en, 2012) | 1986-01-10 |
ZA856990B (en) | 1986-05-28 |
EP0174584A3 (de) | 1987-05-27 |
US4708953A (en) | 1987-11-24 |
BR8504405A (pt) | 1986-07-08 |
AU4747085A (en) | 1986-03-27 |
EP0174584A2 (de) | 1986-03-19 |
KR860002454A (ko) | 1986-04-26 |
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