EA009884B1 - Фенилбензамиды - Google Patents

Info

Publication number

EA009884B1

EA009884B1 EA200500037A EA200500037A EA009884B1 EA 009884 B1 EA009884 B1 EA 009884B1 EA 200500037 A EA200500037 A EA 200500037A EA 200500037 A EA200500037 A EA 200500037A EA 009884 B1 EA009884 B1 EA 009884B1

Authority

EA

Eurasian Patent Office

Prior art keywords

formula

phenyl

plants

methyl

phenylbenzamides

Prior art date

2002-07-02

Links

• Espacenet
• Global Dossier
• Discuss

• ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 title abstract 2
• 244000005700 microbiome Species 0.000 claims abstract description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
• 239000001257 hydrogen Substances 0.000 claims abstract description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
• 239000000460 chlorine Substances 0.000 claims abstract description 5
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
• -1 1,3-dimethylbutyl Chemical group 0.000 claims description 77
• GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical class NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims description 20
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 19
• 238000000034 method Methods 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 5
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
• 239000000945 filler Substances 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• 239000002841 Lewis acid Substances 0.000 claims description 4
• 150000001336 alkenes Chemical class 0.000 claims description 4
• 239000011230 binding agent Substances 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
• 150000007517 lewis acids Chemical class 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
• 150000001448 anilines Chemical class 0.000 claims 1
• 230000008520 organization Effects 0.000 claims 1
• 239000000126 substance Substances 0.000 abstract description 14
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 3
• 239000011630 iodine Substances 0.000 abstract description 3
• 229910052740 iodine Inorganic materials 0.000 abstract description 3
• 238000004519 manufacturing process Methods 0.000 abstract description 3
• 150000001648 bromium Chemical class 0.000 abstract 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
• 239000013067 intermediate product Substances 0.000 abstract 1
• 241000196324 Embryophyta Species 0.000 description 91
• 239000013543 active substance Substances 0.000 description 57
• 230000009471 action Effects 0.000 description 33
• 230000001681 protective effect Effects 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• 238000002360 preparation method Methods 0.000 description 19
• 239000000203 mixture Substances 0.000 description 18
• 230000001965 increasing effect Effects 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000003995 emulsifying agent Substances 0.000 description 15
• 239000000463 material Substances 0.000 description 15
• 150000001875 compounds Chemical class 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
• 238000002474 experimental method Methods 0.000 description 13
• 241000894007 species Species 0.000 description 13
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
• 241000233866 Fungi Species 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 240000008042 Zea mays Species 0.000 description 9
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
• 238000012545 processing Methods 0.000 description 9
• LPZZJKBLKQOBMZ-UHFFFAOYSA-N 2-(4-methylpentan-2-yl)aniline Chemical compound CC(C)CC(C)C1=CC=CC=C1N LPZZJKBLKQOBMZ-UHFFFAOYSA-N 0.000 description 8
• 229920000742 Cotton Polymers 0.000 description 8
• 244000299507 Gossypium hirsutum Species 0.000 description 8
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
• 235000005822 corn Nutrition 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
• 238000011081 inoculation Methods 0.000 description 7
• 108090000623 proteins and genes Proteins 0.000 description 7
• WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 6
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 235000010469 Glycine max Nutrition 0.000 description 6
• 125000002877 alkyl aryl group Chemical group 0.000 description 6
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
• 239000012141 concentrate Substances 0.000 description 6
• 230000006378 damage Effects 0.000 description 6
• 239000008187 granular material Substances 0.000 description 6
• 230000003902 lesion Effects 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 241000894006 Bacteria Species 0.000 description 5
• 238000007796 conventional method Methods 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 235000019439 ethyl acetate Nutrition 0.000 description 5
• 238000010353 genetic engineering Methods 0.000 description 5
• 230000002363 herbicidal effect Effects 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
• 239000002689 soil Substances 0.000 description 5
• 230000009261 transgenic effect Effects 0.000 description 5
• AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 5
• 239000002023 wood Substances 0.000 description 5
• 240000008067 Cucumis sativus Species 0.000 description 4
• 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
• 244000068988 Glycine max Species 0.000 description 4
• 244000070406 Malus silvestris Species 0.000 description 4
• 244000061456 Solanum tuberosum Species 0.000 description 4
• 235000002595 Solanum tuberosum Nutrition 0.000 description 4
• 241000209140 Triticum Species 0.000 description 4
• 235000021307 Triticum Nutrition 0.000 description 4
• 241000700605 Viruses Species 0.000 description 4
• 239000000853 adhesive Substances 0.000 description 4
• 230000001070 adhesive effect Effects 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 229910052802 copper Inorganic materials 0.000 description 4
• 239000010949 copper Substances 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 239000000417 fungicide Substances 0.000 description 4
• 239000004009 herbicide Substances 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• 238000001228 spectrum Methods 0.000 description 4
• 238000005507 spraying Methods 0.000 description 4
• MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 description 3
• ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
• LTHJQLKEXMJOEG-UHFFFAOYSA-N 2-iodo-3-[2-(4-methylpentan-2-yl)phenyl]benzamide Chemical compound CC(CC(C)C)C1=C(C=CC=C1)C=1C(=C(C(=O)N)C=CC=1)I LTHJQLKEXMJOEG-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
• 240000005979 Hordeum vulgare Species 0.000 description 3
• 235000007340 Hordeum vulgare Nutrition 0.000 description 3
• 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 3
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 230000000844 anti-bacterial effect Effects 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 239000003899 bactericide agent Substances 0.000 description 3
• 150000003857 carboxamides Chemical class 0.000 description 3
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
• 238000000227 grinding Methods 0.000 description 3
• 230000012010 growth Effects 0.000 description 3
• 238000003306 harvesting Methods 0.000 description 3
• 230000001976 improved effect Effects 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• BOWMXZSRLGDJMT-UHFFFAOYSA-N n-[2-(4,4-dimethylpentan-2-yl)phenyl]benzamide Chemical compound CC(C)(C)CC(C)C1=CC=CC=C1NC(=O)C1=CC=CC=C1 BOWMXZSRLGDJMT-UHFFFAOYSA-N 0.000 description 3
• 235000016709 nutrition Nutrition 0.000 description 3
• 244000052769 pathogen Species 0.000 description 3
• 235000012015 potatoes Nutrition 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 102000004169 proteins and genes Human genes 0.000 description 3
• 239000011435 rock Substances 0.000 description 3
• 150000003839 salts Chemical class 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 230000002195 synergetic effect Effects 0.000 description 3
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
• MVIVDSWUOGNODP-UHFFFAOYSA-N 2-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1I MVIVDSWUOGNODP-UHFFFAOYSA-N 0.000 description 2
• 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 2
• CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
• BQMRHYBXRAYYQS-UHFFFAOYSA-N 4-dihydroxyphosphinothioyloxy-n,n-diethyl-6-methylpyrimidin-2-amine Chemical compound CCN(CC)C1=NC(C)=CC(OP(O)(O)=S)=N1 BQMRHYBXRAYYQS-UHFFFAOYSA-N 0.000 description 2
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• 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 2
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• 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 2
• 244000188595 Brassica sinapistrum Species 0.000 description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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• MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 2
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
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• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 229940100389 Sulfonylurea Drugs 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
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• 125000003118 aryl group Chemical group 0.000 description 2
• 239000002585 base Substances 0.000 description 2
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• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
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• FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
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• 239000007789 gas Substances 0.000 description 2
• 150000008282 halocarbons Chemical class 0.000 description 2
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