KR20130109975A - 살진균제 옥심 및 하이드라존 - Google Patents
살진균제 옥심 및 하이드라존 Download PDFInfo
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- KR20130109975A KR20130109975A KR1020127033050A KR20127033050A KR20130109975A KR 20130109975 A KR20130109975 A KR 20130109975A KR 1020127033050 A KR1020127033050 A KR 1020127033050A KR 20127033050 A KR20127033050 A KR 20127033050A KR 20130109975 A KR20130109975 A KR 20130109975A
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- South Korea
- Prior art keywords
- alkyl
- compound
- haloalkyl
- formula
- atoms
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims description 117
- 150000002923 oximes Chemical class 0.000 title description 11
- 150000007857 hydrazones Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 499
- 238000000034 method Methods 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 201000010099 disease Diseases 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 28
- 239000000417 fungicide Substances 0.000 claims description 255
- -1 cyano, amino Chemical group 0.000 claims description 180
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 239000001257 hydrogen Substances 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 62
- 150000002367 halogens Chemical class 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 55
- 150000001721 carbon Chemical group 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 36
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 125000004434 sulfur atom Chemical group 0.000 claims description 36
- 239000007788 liquid Substances 0.000 claims description 33
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 32
- 125000001624 naphthyl group Chemical group 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 29
- 239000003085 diluting agent Substances 0.000 claims description 27
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 239000004094 surface-active agent Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 14
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 13
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 9
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 244000000004 fungal plant pathogen Species 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 6
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 2
- UZNLYPZRBILUNX-UHFFFAOYSA-N 1-[4-[4-(hydroxyiminomethyl)-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(C=NO)N=2)CC1 UZNLYPZRBILUNX-UHFFFAOYSA-N 0.000 claims description 2
- YMPJINKZPMDWLR-UHFFFAOYSA-N 1-[4-[4-[c-[2-(2,6-difluorophenyl)-2-hydroxyethyl]-n-hydroxycarbonimidoyl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C(CC(O)C=2C(=CC=CC=2F)F)=NO)CC1 YMPJINKZPMDWLR-UHFFFAOYSA-N 0.000 claims description 2
- GZWGMBYFCNOYKK-UHFFFAOYSA-N 1-[4-[4-[c-[2-(2,6-difluorophenyl)ethenyl]-n-hydroxycarbonimidoyl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C(C=CC=2C(=CC=CC=2F)F)=NO)CC1 GZWGMBYFCNOYKK-UHFFFAOYSA-N 0.000 claims description 2
- SCTAWEVXLMZZSI-UHFFFAOYSA-N 1-[4-[4-[c-[2-(2,6-difluorophenyl)ethenyl]-n-methoxycarbonimidoyl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound C=1SC(C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)=NC=1C(=NOC)C=CC1=C(F)C=CC=C1F SCTAWEVXLMZZSI-UHFFFAOYSA-N 0.000 claims description 2
- WTKYCLRBAHFGCH-UHFFFAOYSA-N 3-(2,6-difluorophenyl)-1-[2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]prop-2-en-1-one Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C(=O)C=CC=2C(=CC=CC=2F)F)CC1 WTKYCLRBAHFGCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- OYNJGSRVHWRSIL-UHFFFAOYSA-N C=1C=CC=CC=1C(C)ON=CC(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C Chemical compound C=1C=CC=CC=1C(C)ON=CC(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C OYNJGSRVHWRSIL-UHFFFAOYSA-N 0.000 claims description 2
- GUSBSEGWLFFSGY-UHFFFAOYSA-N C=1SC(C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)=NC=1C(C)=NOCCC1=CC=CC=C1 Chemical compound C=1SC(C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)=NC=1C(C)=NOCCC1=CC=CC=C1 GUSBSEGWLFFSGY-UHFFFAOYSA-N 0.000 claims description 2
- RLSJXLGPFNBKDJ-UHFFFAOYSA-N [[3-(2,6-difluorophenyl)-1-[2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]prop-2-enylidene]amino] acetate Chemical compound C=1SC(C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)=NC=1C(=NOC(=O)C)C=CC1=C(F)C=CC=C1F RLSJXLGPFNBKDJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 2
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 115
- 244000053095 fungal pathogen Species 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- 230000009471 action Effects 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 68
- 241000196324 Embryophyta Species 0.000 description 43
- 150000001412 amines Chemical class 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 239000002253 acid Substances 0.000 description 41
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 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 38
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 38
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 38
- 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 38
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 38
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 38
- 229940126208 compound 22 Drugs 0.000 description 38
- 229940125833 compound 23 Drugs 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 29
- 241000233866 Fungi Species 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 238000009472 formulation Methods 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- 230000012010 growth Effects 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 20
- 239000003112 inhibitor Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 19
- 125000004122 cyclic group Chemical group 0.000 description 19
- 230000002538 fungal effect Effects 0.000 description 19
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 229930182558 Sterol Natural products 0.000 description 17
- 235000003702 sterols Nutrition 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34660610P | 2010-05-20 | 2010-05-20 | |
| US61/346,606 | 2010-05-20 | ||
| PCT/US2011/032599 WO2011146182A1 (en) | 2010-05-20 | 2011-04-15 | Fungicidal oximes and hydrazones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20130109975A true KR20130109975A (ko) | 2013-10-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127033050A Withdrawn KR20130109975A (ko) | 2010-05-20 | 2011-04-15 | 살진균제 옥심 및 하이드라존 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8722678B2 (enExample) |
| EP (1) | EP2571866A1 (enExample) |
| JP (1) | JP5769799B2 (enExample) |
| KR (1) | KR20130109975A (enExample) |
| CN (1) | CN102933577B (enExample) |
| AR (1) | AR082373A1 (enExample) |
| AU (1) | AU2011256730B2 (enExample) |
| BR (1) | BR112012026708A2 (enExample) |
| IL (1) | IL222549A0 (enExample) |
| MX (1) | MX2012013315A (enExample) |
| TW (1) | TWI501964B (enExample) |
| WO (1) | WO2011146182A1 (enExample) |
| ZA (1) | ZA201207373B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9090604B2 (en) * | 2006-07-27 | 2015-07-28 | E I Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
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2011
- 2011-04-15 EP EP11717108A patent/EP2571866A1/en not_active Withdrawn
- 2011-04-15 US US13/640,092 patent/US8722678B2/en not_active Expired - Fee Related
- 2011-04-15 WO PCT/US2011/032599 patent/WO2011146182A1/en not_active Ceased
- 2011-04-15 JP JP2013511164A patent/JP5769799B2/ja not_active Expired - Fee Related
- 2011-04-15 MX MX2012013315A patent/MX2012013315A/es active IP Right Grant
- 2011-04-15 AU AU2011256730A patent/AU2011256730B2/en not_active Ceased
- 2011-04-15 KR KR1020127033050A patent/KR20130109975A/ko not_active Withdrawn
- 2011-04-15 BR BR112012026708A patent/BR112012026708A2/pt not_active Application Discontinuation
- 2011-04-15 CN CN201180025065.6A patent/CN102933577B/zh not_active Expired - Fee Related
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- 2011-05-20 AR ARP110101745A patent/AR082373A1/es unknown
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| AU2011256730A1 (en) | 2013-07-11 |
| IL222549A0 (en) | 2012-12-31 |
| JP5769799B2 (ja) | 2015-08-26 |
| CN102933577A (zh) | 2013-02-13 |
| TWI501964B (zh) | 2015-10-01 |
| EP2571866A1 (en) | 2013-03-27 |
| AR082373A1 (es) | 2012-12-05 |
| JP2013528602A (ja) | 2013-07-11 |
| MX2012013315A (es) | 2012-12-05 |
| WO2011146182A1 (en) | 2011-11-24 |
| BR112012026708A2 (pt) | 2015-09-22 |
| TW201144305A (en) | 2011-12-16 |
| US8722678B2 (en) | 2014-05-13 |
| CN102933577B (zh) | 2014-08-06 |
| ZA201207373B (en) | 2014-12-23 |
| US20130030002A1 (en) | 2013-01-31 |
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