ZA200502930B - Quinolin-, isoquinolin-, and quinazolin-oxyalkylamines and their uses as fungicides. - Google Patents

Info

Publication number

ZA200502930B

ZA200502930B ZA200502930A ZA200502930A ZA200502930B ZA 200502930 B ZA200502930 B ZA 200502930B ZA 200502930 A ZA200502930 A ZA 200502930A ZA 200502930 A ZA200502930 A ZA 200502930A ZA 200502930 B ZA200502930 B ZA 200502930B

Authority

ZA

South Africa

Prior art keywords

alkyl

optionally substituted

compounds

compound

halo

Prior art date

2002-11-26

Links

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• Global Dossier
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• 239000000417 fungicide Substances 0.000 title description 7
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 389
• -1 nitro, amino Chemical group 0.000 claims description 134
• 239000000203 mixture Substances 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 93
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
• 229910052739 hydrogen Inorganic materials 0.000 claims description 78
• 239000001257 hydrogen Substances 0.000 claims description 68
• 125000005843 halogen group Chemical group 0.000 claims description 67
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
• 125000003545 alkoxy group Chemical group 0.000 claims description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 238000000034 method Methods 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 125000004414 alkyl thio group Chemical group 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 10
• 230000000855 fungicidal effect Effects 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 9
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 241000233866 Fungi Species 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000006606 n-butoxy group Chemical group 0.000 claims description 8
• 239000002689 soil Substances 0.000 claims description 7
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• LDKSCZJUIURGMW-UHFFFAOYSA-N 1-isothiocyanato-3-methylsulfanylpropane Chemical group CSCCCN=C=S LDKSCZJUIURGMW-UHFFFAOYSA-N 0.000 claims description 4
• JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims description 4
• 125000004011 3 membered carbocyclic group Chemical group 0.000 claims description 4
• 125000001845 4 membered carbocyclic group Chemical group 0.000 claims description 4
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 4
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 239000001963 growth medium Substances 0.000 claims description 3
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
• 230000008635 plant growth Effects 0.000 claims description 3
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
• 230000003032 phytopathogenic effect Effects 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 229940125904 compound 1 Drugs 0.000 description 166
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
• 150000002431 hydrogen Chemical class 0.000 description 64
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• 238000002360 preparation method Methods 0.000 description 48
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• 239000007787 solid Substances 0.000 description 42
• 239000000243 solution Substances 0.000 description 35
• 239000000047 product Substances 0.000 description 32
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 238000005481 NMR spectroscopy Methods 0.000 description 26
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 26
• 235000019341 magnesium sulphate Nutrition 0.000 description 26
• 239000003921 oil Substances 0.000 description 25
• 235000019198 oils Nutrition 0.000 description 24
• 239000002904 solvent Substances 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• 229910052727 yttrium Inorganic materials 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
• 150000001412 amines Chemical class 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• 239000007788 liquid Substances 0.000 description 17
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 241000196324 Embryophyta Species 0.000 description 15
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 15
• 238000004587 chromatography analysis Methods 0.000 description 15
• 150000002148 esters Chemical class 0.000 description 14
• 239000000284 extract Substances 0.000 description 13
• 238000009472 formulation Methods 0.000 description 13
• 239000000377 silicon dioxide Substances 0.000 description 13
• 241000209140 Triticum Species 0.000 description 12
• 235000021307 Triticum Nutrition 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 239000008346 aqueous phase Substances 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 230000003213 activating effect Effects 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 239000012298 atmosphere Substances 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 235000021391 short chain fatty acids Nutrition 0.000 description 8
• VKNVIMFQGNSLFW-UHFFFAOYSA-N 2-bromo-n-(2-methylpent-3-yn-2-yl)butanamide Chemical compound CCC(Br)C(=O)NC(C)(C)C#CC VKNVIMFQGNSLFW-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 240000005979 Hordeum vulgare Species 0.000 description 7
• 235000007340 Hordeum vulgare Nutrition 0.000 description 7
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
• 241000220225 Malus Species 0.000 description 7
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
• 240000003768 Solanum lycopersicum Species 0.000 description 7
• 239000004530 micro-emulsion Substances 0.000 description 7
• 239000004546 suspension concentrate Substances 0.000 description 7
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• 244000105624 Arachis hypogaea Species 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 235000021016 apples Nutrition 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
• 239000004495 emulsifiable concentrate Substances 0.000 description 6
• 239000000839 emulsion Substances 0.000 description 6
• 235000019441 ethanol Nutrition 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• 235000020232 peanut Nutrition 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 238000011282 treatment Methods 0.000 description 6
• 235000013311 vegetables Nutrition 0.000 description 6
• 239000000080 wetting agent Substances 0.000 description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 5
• IGCRMJVOMNKTGB-UHFFFAOYSA-N 3-bromoquinolin-6-ol Chemical compound N1=CC(Br)=CC2=CC(O)=CC=C21 IGCRMJVOMNKTGB-UHFFFAOYSA-N 0.000 description 5
• 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 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 241000220324 Pyrus Species 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 235000002595 Solanum tuberosum Nutrition 0.000 description 5
• 244000061456 Solanum tuberosum Species 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 125000001246 bromo group Chemical group Br* 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 125000001309 chloro group Chemical group Cl* 0.000 description 5
• 239000004491 dispersible concentrate Substances 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 5
• 235000021017 pears Nutrition 0.000 description 5
• 235000012015 potatoes Nutrition 0.000 description 5
• OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 239000004094 surface-active agent Substances 0.000 description 5
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
• WDGKIHQSQWMRGD-UHFFFAOYSA-N 2-bromo-3-methoxy-n-(2-methylpent-3-yn-2-yl)propanamide Chemical compound COCC(Br)C(=O)NC(C)(C)C#CC WDGKIHQSQWMRGD-UHFFFAOYSA-N 0.000 description 4
• ZHTLAJOFJCDVFR-UHFFFAOYSA-N 4-amino-4-methylpent-2-yn-1-ol;hydrochloride Chemical compound Cl.CC(C)(N)C#CCO ZHTLAJOFJCDVFR-UHFFFAOYSA-N 0.000 description 4
• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
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• 244000068988 Glycine max Species 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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• 239000000194 fatty acid Substances 0.000 description 4
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• 150000004665 fatty acids Chemical class 0.000 description 4
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• SADNUYOZFVBJAH-UHFFFAOYSA-N 2-(3-bromoquinolin-6-yl)oxy-n-(2-methylpent-3-yn-2-yl)butanamide Chemical compound N1=CC(Br)=CC2=CC(OC(CC)C(=O)NC(C)(C)C#CC)=CC=C21 SADNUYOZFVBJAH-UHFFFAOYSA-N 0.000 description 3
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• SUWCIZJNWUJGMV-UHFFFAOYSA-N 2-ethoxy-2-quinolin-6-yloxyacetic acid Chemical compound N1=CC=CC2=CC(OC(OCC)C(O)=O)=CC=C21 SUWCIZJNWUJGMV-UHFFFAOYSA-N 0.000 description 3
• ZVHRVRUKKUAKEN-UHFFFAOYSA-N 2-quinolin-6-yloxybutanoic acid Chemical compound N1=CC=CC2=CC(OC(CC)C(O)=O)=CC=C21 ZVHRVRUKKUAKEN-UHFFFAOYSA-N 0.000 description 3
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• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
• XIGQUURJVUSYBF-UHFFFAOYSA-N 3-bromo-6-nitroquinoline Chemical compound N1=CC(Br)=CC2=CC([N+](=O)[O-])=CC=C21 XIGQUURJVUSYBF-UHFFFAOYSA-N 0.000 description 3
• XOXNGIYWQRRRPW-UHFFFAOYSA-N 3-bromoquinolin-6-amine Chemical compound N1=CC(Br)=CC2=CC(N)=CC=C21 XOXNGIYWQRRRPW-UHFFFAOYSA-N 0.000 description 3
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• 239000007864 aqueous solution Substances 0.000 description 3
• 235000021015 bananas Nutrition 0.000 description 3
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