JP2000500739A - 複素環式殺菌剤 - Google Patents
複素環式殺菌剤Info
- Publication number
- JP2000500739A JP2000500739A JP9514831A JP51483197A JP2000500739A JP 2000500739 A JP2000500739 A JP 2000500739A JP 9514831 A JP9514831 A JP 9514831A JP 51483197 A JP51483197 A JP 51483197A JP 2000500739 A JP2000500739 A JP 2000500739A
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- arh
- compound
- formula
- group
- 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.)
- Ceased
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 29
- 239000000417 fungicide Substances 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002252 acyl group Chemical group 0.000 claims abstract description 13
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Chemical group 0.000 claims abstract description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 68
- -1 1-methylbenzyl Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 238000005507 spraying Methods 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 230000000361 pesticidal effect Effects 0.000 claims description 3
- 244000000004 fungal plant pathogen Species 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000012267 brine Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 6
- 235000001671 coumarin Nutrition 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- 241001480061 Blumeria graminis Species 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 150000004775 coumarins Chemical class 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical group C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
- 241000233679 Peronosporaceae Species 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
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- 238000005553 drilling Methods 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
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- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
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- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
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- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- 238000002791 soaking Methods 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 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 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 125000002769 thiazolinyl group Chemical group 0.000 description 1
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- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/54—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 substituted in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9521023.3 | 1995-10-13 | ||
| GBGB9521023.3A GB9521023D0 (en) | 1995-10-13 | 1995-10-13 | Fungicides |
| GBGB9524152.7A GB9524152D0 (en) | 1995-11-25 | 1995-11-25 | Fungicides |
| GB9524152.7 | 1995-11-25 | ||
| GB9525525.3 | 1995-12-14 | ||
| GBGB9525514.7A GB9525514D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
| GBGB9525526.1A GB9525526D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
| GB9525524.6 | 1995-12-14 | ||
| GB9525526.1 | 1995-12-14 | ||
| GB9525514.7 | 1995-12-14 | ||
| GBGB9525525.3A GB9525525D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
| GBGB9525524.6A GB9525524D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
| PCT/GB1996/002491 WO1997013762A1 (en) | 1995-10-13 | 1996-10-11 | Heterocyclic fungicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000500739A true JP2000500739A (ja) | 2000-01-25 |
| JP2000500739A5 JP2000500739A5 (enExample) | 2004-10-07 |
Family
ID=27547250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9514831A Ceased JP2000500739A (ja) | 1995-10-13 | 1996-10-11 | 複素環式殺菌剤 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6034121A (enExample) |
| EP (1) | EP0861242B1 (enExample) |
| JP (1) | JP2000500739A (enExample) |
| KR (1) | KR100428274B1 (enExample) |
| CN (1) | CN1117741C (enExample) |
| AT (1) | ATE201674T1 (enExample) |
| AU (1) | AU7223896A (enExample) |
| BR (1) | BR9610970A (enExample) |
| CA (1) | CA2233666C (enExample) |
| DE (1) | DE69613139T2 (enExample) |
| DK (1) | DK0861242T3 (enExample) |
| ES (1) | ES2157462T3 (enExample) |
| GR (1) | GR3036017T3 (enExample) |
| HU (1) | HUP9900753A3 (enExample) |
| IL (1) | IL123701A (enExample) |
| PL (1) | PL187175B1 (enExample) |
| PT (1) | PT861242E (enExample) |
| TW (1) | TW420671B (enExample) |
| WO (1) | WO1997013762A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006069906A (ja) * | 2004-08-31 | 2006-03-16 | Sumitomo Chemical Co Ltd | クロモン化合物及びその用途 |
| JP2009537518A (ja) * | 2006-05-15 | 2009-10-29 | エックスティーエル バイオファーマシューティカルズ，リミテッド | ３，４−二置換クマリン及びキノロン化合物 |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7738298A (en) * | 1996-12-19 | 1998-07-15 | Agrevo Uk Limited | Chromones useful as fungicides |
| AU4694999A (en) * | 1998-08-06 | 2000-02-28 | Warner-Lambert Company | Use of thiazolidinedione derivatives for the treatment or prevention of cataracts |
| US6169185B1 (en) | 1999-02-25 | 2001-01-02 | Day-Glo Color Corp. | Ink jet printing inks |
| DE19935963A1 (de) * | 1999-07-30 | 2001-02-01 | Bayer Ag | Biphenylsubstituierte cyclische Ketoenole |
| IL160010A0 (en) * | 2001-07-23 | 2004-06-20 | Univ Ramot | Methods and compositions for treating fungal infections |
| FR2828196A1 (fr) * | 2001-08-03 | 2003-02-07 | Aventis Cropscience Sa | Derives de chromone a action fongicide, procede de preparation et application dans le domaine de l'agriculture |
| US6703514B2 (en) * | 2002-05-14 | 2004-03-09 | Vivo Quest, Inc. | 4-thio coumarins |
| US7148253B2 (en) * | 2002-05-14 | 2006-12-12 | Xtl Biopharmaceuticals Ltd. | 4-thio coumarins |
| WO2004014880A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Chromone derivatives as matrix metalloproteinase inhibitors |
| EP1443044A1 (fr) * | 2003-02-03 | 2004-08-04 | Bayer CropScience SA | Procédés de préparation de dérivés de iodo-chromones fongicides |
| CN1281599C (zh) * | 2003-05-15 | 2006-10-25 | 中国科学院上海有机化学研究所 | 香豆素类化合物和合成方法 |
| US7538233B2 (en) * | 2003-09-05 | 2009-05-26 | Aventis Pharmaceuticals Inc. | Coumarins as iNOS inhibitors |
| CN1310899C (zh) * | 2003-11-11 | 2007-04-18 | 沈阳化工研究院 | 具有杀虫、杀菌活性的苯并吡喃酮类化合物及制备与应用 |
| EP1614685A1 (en) * | 2004-07-07 | 2006-01-11 | Bayer CropScience AG | Process for preparing 2-chloro-6-Halogeno-3-alkyl-4H-chrom en-4-one or 2-chloro-3-alkyl-4H-chromen-4-one derivatives |
| KR20070061846A (ko) * | 2004-09-30 | 2007-06-14 | 뉴로서치 에이/에스 | 신규한 크로멘-2-온 유도체 및 모노아민 신경전달물질재흡수 억제제로서의 이의 용도 |
| CN101023081A (zh) * | 2004-09-30 | 2007-08-22 | 神经研究公司 | 新颖的色烯－2－酮衍生物及其作为单胺神经递质再摄取抑制剂的用途 |
| US7617092B2 (en) * | 2004-12-01 | 2009-11-10 | Microsoft Corporation | Safe, secure resource editing for application localization |
| BRPI0515830A (pt) * | 2004-12-21 | 2008-08-05 | F Hoffmann La Roche | derivados de cromano e usos dos mesmos no tratamento de distúrbios do sistema nervoso central |
| MX2009000148A (es) * | 2006-07-07 | 2009-10-26 | Kalypsys Inc | Inhibidores heteroaril biciclicos de fosfodiesterasa 4. |
| PL2121677T3 (pl) | 2006-12-20 | 2011-04-29 | Neurosearch As | Nowe pochodne chromen-2-onu i ich zastosowanie jako inhibitorów wychwytu zwrotnego neurotransmiteru monoaminowego |
| TW200904815A (en) * | 2007-05-09 | 2009-02-01 | Neurosearch As | Novel compounds |
| CN101456853B (zh) * | 2009-01-05 | 2011-09-21 | 江苏省农业科学院 | 仿生系列化合物7-取代-8-(3，3’-二取代丙基)苯并吡喃-2-酮类合成及其作为农药的应用 |
| WO2010130620A1 (en) | 2009-05-15 | 2010-11-18 | Neurosearch A/S | Chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| WO2011092061A1 (en) | 2010-01-29 | 2011-08-04 | Neurosearch A/S | Chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| US8318953B2 (en) * | 2010-06-23 | 2012-11-27 | Aat Bioquest, Inc. | Reactive coumarin derivatives and their use in cellular analyses |
| US20130079394A1 (en) * | 2011-09-23 | 2013-03-28 | Cnrs (Centre National Recherche Scientifique) | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
| US9063420B2 (en) | 2013-07-16 | 2015-06-23 | Rohm And Haas Electronic Materials Llc | Photoresist composition, coated substrate, and method of forming electronic device |
| US9410016B2 (en) | 2013-07-16 | 2016-08-09 | Dow Global Technologies Llc | Aromatic polyacetals and articles comprising them |
| US8962779B2 (en) | 2013-07-16 | 2015-02-24 | Dow Global Technologies Llc | Method of forming polyaryl polymers |
| US8933239B1 (en) | 2013-07-16 | 2015-01-13 | Dow Global Technologies Llc | Bis(aryl)acetal compounds |
| CN103524471B (zh) * | 2013-10-31 | 2015-10-14 | 青岛农业大学 | 一种n-酰基取代的氨基香豆素及其杀虫活性 |
| EP3397056A1 (en) * | 2015-12-30 | 2018-11-07 | Investigaciones Biológicas en Agroquimicos Rosario S.A. | Herbicidal composition comprising chromone derivatives and a method for weed control |
| CN106900712A (zh) * | 2016-12-05 | 2017-06-30 | 青岛农业大学 | N‑硬脂酰基‑6‑氨基香豆素的制剂及其应用 |
| CN107556296B (zh) * | 2017-09-06 | 2020-10-02 | 南京工业大学 | 一种2-羟基-3-氮杂环色酮类化合物及其合成方法和在抗真菌药物中的应用 |
| CN109134444B (zh) * | 2018-02-11 | 2021-07-23 | 陕西师范大学 | 3-(2-呋喃)-4-羟基香豆素类化合物及其制备方法和抗植物真菌的应用 |
| CN109053660B (zh) * | 2018-07-13 | 2022-04-26 | 青岛农业大学 | 含三氟甲硫基香豆素类化合物、其合成方法及其应用 |
| EP4015512A1 (en) | 2020-12-16 | 2022-06-22 | AMO Ireland | Optically active devices |
| CN113004240B (zh) * | 2021-03-11 | 2023-02-03 | 西华大学 | 苯并吡喃类化合物及其在农药中的用途 |
| CN113024500B (zh) * | 2021-03-11 | 2023-02-03 | 西华大学 | 6,8-二溴苯并吡喃衍生物及其在农药中的应用 |
| CN112939919B (zh) * | 2021-03-11 | 2023-02-03 | 西华大学 | 2-氨基苯并吡喃类化合物及其在农药中的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3141893A (en) * | 1960-11-15 | 1964-07-21 | Geigy Chem Corp | 4-amino-coumarins |
| DE1225658B (de) * | 1960-11-15 | 1966-09-29 | Geigy Ag J R | Verfahren zur Herstellung von Cumarinderivaten |
| FR2321M (fr) * | 1962-01-16 | 1964-02-10 | Lipha | Nouveaux médicaments cholérétiques de la série des hydroxy-coumarines. |
| CA978977A (en) * | 1971-05-31 | 1975-12-02 | Yasuo Makisumi | Coumarin derivatives and production thereof |
| US4065574A (en) * | 1975-08-29 | 1977-12-27 | The Upjohn Company | New method for controlling fungi using 4-chromone, 4-chromanone, 4-chromone oxime and 4-chromanone oxime compounds |
| FR2368952A1 (fr) * | 1976-02-25 | 1978-05-26 | Lipha | Nouveaux aminoalcoxy-4 (2 h) pyranone-2,3 substitues-5,6 condenses |
| ZA873745B (en) * | 1986-06-04 | 1988-10-26 | Daiichi Seiyaku Co | Benzopyran derivatives |
| AU8612491A (en) * | 1990-09-07 | 1992-03-30 | Schering Corporation | Antiviral compounds |
| DE69128481T2 (de) * | 1990-09-07 | 1998-04-09 | Schering Corp | Antivirale und antihypertensive verbindungen |
| JPH05331009A (ja) * | 1992-06-01 | 1993-12-14 | Asahi Denka Kogyo Kk | 水中有害生物防除剤 |
| US5510375A (en) * | 1993-11-19 | 1996-04-23 | Warner-Lambert Company | Coumarin derivatives as protease inhibitors and antiviral agents |
| US5563280A (en) * | 1994-07-25 | 1996-10-08 | American Cyanamid Co. | 4-Phenoxycoumarins as herbicidal agents |
-
1996
- 1996-10-11 PL PL96326159A patent/PL187175B1/pl not_active IP Right Cessation
- 1996-10-11 BR BR9610970A patent/BR9610970A/pt not_active Application Discontinuation
- 1996-10-11 ES ES96933541T patent/ES2157462T3/es not_active Expired - Lifetime
- 1996-10-11 JP JP9514831A patent/JP2000500739A/ja not_active Ceased
- 1996-10-11 HU HU9900753A patent/HUP9900753A3/hu unknown
- 1996-10-11 DE DE69613139T patent/DE69613139T2/de not_active Expired - Fee Related
- 1996-10-11 WO PCT/GB1996/002491 patent/WO1997013762A1/en not_active Ceased
- 1996-10-11 PT PT96933541T patent/PT861242E/pt unknown
- 1996-10-11 CN CN96198881A patent/CN1117741C/zh not_active Expired - Fee Related
- 1996-10-11 AU AU72238/96A patent/AU7223896A/en not_active Abandoned
- 1996-10-11 EP EP96933541A patent/EP0861242B1/en not_active Expired - Lifetime
- 1996-10-11 KR KR10-1998-0702689A patent/KR100428274B1/ko not_active Expired - Fee Related
- 1996-10-11 IL IL12370196A patent/IL123701A/en not_active IP Right Cessation
- 1996-10-11 CA CA002233666A patent/CA2233666C/en not_active Expired - Fee Related
- 1996-10-11 AT AT96933541T patent/ATE201674T1/de not_active IP Right Cessation
- 1996-10-11 DK DK96933541T patent/DK0861242T3/da active
- 1996-10-17 TW TW085112706A patent/TW420671B/zh not_active IP Right Cessation
-
1998
- 1998-04-01 US US09/051,135 patent/US6034121A/en not_active Expired - Fee Related
-
2001
- 2001-06-13 GR GR20010400495T patent/GR3036017T3/el not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006069906A (ja) * | 2004-08-31 | 2006-03-16 | Sumitomo Chemical Co Ltd | クロモン化合物及びその用途 |
| JP2009537518A (ja) * | 2006-05-15 | 2009-10-29 | エックスティーエル バイオファーマシューティカルズ，リミテッド | ３，４−二置換クマリン及びキノロン化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2233666C (en) | 2006-05-09 |
| CN1204330A (zh) | 1999-01-06 |
| ATE201674T1 (de) | 2001-06-15 |
| HUP9900753A3 (en) | 2000-04-28 |
| PL187175B1 (pl) | 2004-05-31 |
| CA2233666A1 (en) | 1997-04-17 |
| WO1997013762A1 (en) | 1997-04-17 |
| TW420671B (en) | 2001-02-01 |
| AU7223896A (en) | 1997-04-30 |
| BR9610970A (pt) | 1999-04-06 |
| DE69613139D1 (de) | 2001-07-05 |
| PT861242E (pt) | 2001-10-30 |
| DK0861242T3 (da) | 2001-08-06 |
| ES2157462T3 (es) | 2001-08-16 |
| IL123701A0 (en) | 1998-10-30 |
| DE69613139T2 (de) | 2001-09-13 |
| US6034121A (en) | 2000-03-07 |
| GR3036017T3 (en) | 2001-09-28 |
| PL326159A1 (en) | 1998-08-31 |
| CN1117741C (zh) | 2003-08-13 |
| KR100428274B1 (ko) | 2005-01-15 |
| EP0861242A1 (en) | 1998-09-02 |
| IL123701A (en) | 2002-03-10 |
| HUP9900753A2 (hu) | 1999-07-28 |
| KR19990064203A (ko) | 1999-07-26 |
| EP0861242B1 (en) | 2001-05-30 |
| MX9802858A (es) | 1998-11-30 |
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