CN105130900B - 杀真菌吡唑类 - Google Patents
杀真菌吡唑类 Download PDFInfo
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- CN105130900B CN105130900B CN201510578968.7A CN201510578968A CN105130900B CN 105130900 B CN105130900 B CN 105130900B CN 201510578968 A CN201510578968 A CN 201510578968A CN 105130900 B CN105130900 B CN 105130900B
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- Prior art keywords
- compound
- formula
- pyrazoles
- methyl
- chloro
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- 150000003217 pyrazoles Chemical class 0.000 title abstract description 19
- 229940121375 antifungal agent Drugs 0.000 title abstract description 11
- 230000000843 anti-fungal effect Effects 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 687
- 239000000203 mixture Substances 0.000 claims abstract description 123
- 238000000034 method Methods 0.000 claims abstract description 59
- 201000010099 disease Diseases 0.000 claims abstract description 45
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- -1 methoxyl group Chemical group 0.000 claims description 257
- 230000000855 fungicidal effect Effects 0.000 claims description 251
- 239000000417 fungicide Substances 0.000 claims description 231
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 101
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 238000006467 substitution reaction Methods 0.000 claims description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 241000196324 Embryophyta Species 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 28
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 239000004094 surface-active agent Substances 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000004615 ingredient Substances 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- 244000000004 fungal plant pathogen Species 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims 3
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 claims 3
- 244000053095 fungal pathogen Species 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 107
- 239000002585 base Substances 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
- 125000000217 alkyl group Chemical group 0.000 description 72
- 230000009471 action Effects 0.000 description 64
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- 150000002367 halogens Chemical class 0.000 description 53
- 241000894006 Bacteria Species 0.000 description 52
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
- 230000015572 biosynthetic process Effects 0.000 description 45
- 239000000126 substance Substances 0.000 description 45
- 239000000243 solution Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 38
- 241000233866 Fungi Species 0.000 description 37
- 229910052799 carbon Inorganic materials 0.000 description 36
- 235000002639 sodium chloride Nutrition 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 31
- 239000000047 product Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- 230000008859 change Effects 0.000 description 29
- 235000019441 ethanol Nutrition 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000012360 testing method Methods 0.000 description 27
- 239000003153 chemical reaction reagent Substances 0.000 description 25
- 125000003545 alkoxy group Chemical group 0.000 description 24
- 229940125773 compound 10 Drugs 0.000 description 24
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- 239000003112 inhibitor Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 23
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 22
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 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 22
- 229940126543 compound 14 Drugs 0.000 description 22
- 229940126214 compound 3 Drugs 0.000 description 22
- 229940125936 compound 42 Drugs 0.000 description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 21
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 21
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 21
- 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 21
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 21
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 21
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 21
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 21
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 21
- 229940126657 Compound 17 Drugs 0.000 description 21
- 229940126639 Compound 33 Drugs 0.000 description 21
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
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- 125000000623 heterocyclic group Chemical group 0.000 description 21
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 21
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- 230000012010 growth Effects 0.000 description 20
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- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 19
- DJMOXMNDXFFONV-UHFFFAOYSA-N 1,3-dimethyl-7-[2-(n-methylanilino)ethyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCN(C)C1=CC=CC=C1 DJMOXMNDXFFONV-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 19
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- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 18
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 16
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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- 229910052708 sodium Inorganic materials 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
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- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/02—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 two hetero rings
- C07D403/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37915910P | 2010-09-01 | 2010-09-01 | |
| US61/379159 | 2010-09-01 | ||
| CN201180042397.5A CN103079406B (zh) | 2010-09-01 | 2011-08-31 | 杀真菌吡唑类 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180042397.5A Division CN103079406B (zh) | 2010-09-01 | 2011-08-31 | 杀真菌吡唑类 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105130900A CN105130900A (zh) | 2015-12-09 |
| CN105130900B true CN105130900B (zh) | 2018-05-22 |
Family
ID=44651972
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510578968.7A Expired - Fee Related CN105130900B (zh) | 2010-09-01 | 2011-08-31 | 杀真菌吡唑类 |
| CN201180042397.5A Expired - Fee Related CN103079406B (zh) | 2010-09-01 | 2011-08-31 | 杀真菌吡唑类 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180042397.5A Expired - Fee Related CN103079406B (zh) | 2010-09-01 | 2011-08-31 | 杀真菌吡唑类 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8754115B2 (https=) |
| EP (1) | EP2611297B1 (https=) |
| JP (1) | JP6066910B2 (https=) |
| KR (1) | KR20130139892A (https=) |
| CN (2) | CN105130900B (https=) |
| AR (1) | AR082869A1 (https=) |
| AU (1) | AU2011295998A1 (https=) |
| BR (2) | BR112013004835B1 (https=) |
| ES (1) | ES2546671T3 (https=) |
| MX (1) | MX2013002400A (https=) |
| PL (1) | PL2611297T3 (https=) |
| TW (1) | TW201245155A (https=) |
| UY (1) | UY33582A (https=) |
| WO (1) | WO2012030922A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TWI568721B (zh) | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| US20140235689A1 (en) * | 2013-02-20 | 2014-08-21 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| JPWO2014157569A1 (ja) | 2013-03-28 | 2017-02-16 | 武田薬品工業株式会社 | 複素環化合物 |
| TWI652012B (zh) * | 2013-05-20 | 2019-03-01 | 杜邦股份有限公司 | 殺真菌吡唑的固態形式 |
| EP3036223A1 (en) | 2013-08-20 | 2016-06-29 | E. I. du Pont de Nemours and Company | Fungicidal pyrazoles |
| PL3078265T3 (pl) * | 2013-12-05 | 2017-10-31 | Kureha Corp | Substancja chemiczna do zastosowań rolniczych lub ogrodniczych, metoda ochrony roślin przed chorobami oraz produkt ochrony roślin przed chorobami |
| EP3078266A4 (en) | 2013-12-05 | 2016-11-23 | Kureha Corp | AGRICULTURAL OR HORTICULTURAL CHEMICAL, METHOD OF CONTROLLING PLANT DISEASES AND PLANT DISEASE CONTROL PRODUCT |
| WO2015089800A1 (en) | 2013-12-19 | 2015-06-25 | Eli Lilly And Company | Fluorophenyl pyrazol compounds |
| US20170037014A1 (en) * | 2014-05-06 | 2017-02-09 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| US10246420B2 (en) | 2014-07-24 | 2019-04-02 | Bayer Cropscience Aktiengesellschaft | Pyrazole derivatives |
| BR112017018140A2 (pt) | 2015-03-19 | 2018-04-10 | Du Pont | ?composto, composição fungicida e método de controle de doenças de plantas? |
| WO2016201662A1 (en) * | 2015-06-18 | 2016-12-22 | Eli Lilly And Company | Fluoropyridyl pyrazol compounds |
| EP3412658A1 (en) * | 2017-06-09 | 2018-12-12 | Solvay Sa | Processes for the manufacture of sulfur-substitued pyrazole derivatives |
| AU2020366425A1 (en) * | 2019-10-18 | 2022-04-21 | Fmc Corporation | Methods for the preparation of 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid |
| EP3976591B1 (en) * | 2019-10-18 | 2023-04-19 | FMC Corporation | Methods for the preparation of 5-bromo-2-(3-chloro-pyridin-2-yl)-2h-pyrazole-3-carboxylic acid |
| TW202241859A (zh) * | 2021-01-29 | 2022-11-01 | 美商富曼西公司 | 用於製備５－溴－２－（３－氯－吡啶－２－基）－２ｈ－吡唑－３－甲酸之方法 |
| CN120500474A (zh) * | 2023-01-09 | 2025-08-15 | 弗陆创新有限公司 | 制备3-卤甲基取代的1-甲基-1h-吡唑-4-碳腈及其衍生物及其中间体的新方法 |
| CN116606263B (zh) * | 2023-05-26 | 2025-06-13 | 青岛科技大学 | 一种含氟苯联噻唑双酯类化合物及其用途 |
| WO2025168620A1 (en) * | 2024-02-07 | 2025-08-14 | Bayer Aktiengesellschaft | Heteroaryl-substituted 4,5-dihydro-1h-2,4,5-oxadiazines as novel fungicides |
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| EP0556396A1 (en) * | 1990-11-09 | 1993-08-25 | Nissan Chemical Industries, Limited | Substituted pyrazole derivative and agrohorticultural bactericide |
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| NL7512983A (nl) | 1974-11-06 | 1976-05-10 | Parke Davis & Co | Werkwijze voor het bereiden van diazepineverbin- dingen, werkwijze voor het bereiden van een far- maceutisch preparaat met toepassing daarvan als- mede een zo gevormd preparaat. |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
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-
2011
- 2011-08-26 TW TW100130635A patent/TW201245155A/zh unknown
- 2011-08-31 US US13/816,847 patent/US8754115B2/en not_active Expired - Fee Related
- 2011-08-31 EP EP11757463.2A patent/EP2611297B1/en not_active Not-in-force
- 2011-08-31 JP JP2013527253A patent/JP6066910B2/ja not_active Expired - Fee Related
- 2011-08-31 PL PL11757463T patent/PL2611297T3/pl unknown
- 2011-08-31 ES ES11757463.2T patent/ES2546671T3/es active Active
- 2011-08-31 MX MX2013002400A patent/MX2013002400A/es not_active Application Discontinuation
- 2011-08-31 BR BR112013004835-2A patent/BR112013004835B1/pt not_active IP Right Cessation
- 2011-08-31 CN CN201510578968.7A patent/CN105130900B/zh not_active Expired - Fee Related
- 2011-08-31 UY UY33582A patent/UY33582A/es not_active Application Discontinuation
- 2011-08-31 BR BR122017015898-8A patent/BR122017015898B1/pt not_active IP Right Cessation
- 2011-08-31 CN CN201180042397.5A patent/CN103079406B/zh not_active Expired - Fee Related
- 2011-08-31 KR KR20137008060A patent/KR20130139892A/ko not_active Withdrawn
- 2011-08-31 WO PCT/US2011/049908 patent/WO2012030922A1/en not_active Ceased
- 2011-08-31 AU AU2011295998A patent/AU2011295998A1/en not_active Abandoned
- 2011-09-01 AR ARP110103199 patent/AR082869A1/es unknown
-
2014
- 2014-04-10 US US14/249,658 patent/US9131693B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS59148782A (ja) * | 1983-02-04 | 1984-08-25 | ワ−ナ−−ランバ−ト・コンパニ− | ５−アミノメチル−イミダゾ−ル−１−イル−１，３−ジアルキル−１ｈ−ピラゾ−ル−４−イルアロイルメタノン類 |
| US5189040A (en) * | 1990-05-28 | 1993-02-23 | Sumitomo Chemical Company, Limited | Pyrazole derivatives, method for producing the same and agricultural and/or horticultural fungicides containing the same as active ingredient |
| EP0556396A1 (en) * | 1990-11-09 | 1993-08-25 | Nissan Chemical Industries, Limited | Substituted pyrazole derivative and agrohorticultural bactericide |
| CN101687845A (zh) * | 2007-07-11 | 2010-03-31 | 先正达参股股份有限公司 | 用作杀真菌剂的异噻唑和吡唑衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| UY33582A (es) | 2012-03-30 |
| BR122017015898B1 (pt) | 2018-05-15 |
| CN103079406A (zh) | 2013-05-01 |
| EP2611297A1 (en) | 2013-07-10 |
| CN103079406B (zh) | 2016-03-30 |
| JP2013536856A (ja) | 2013-09-26 |
| KR20130139892A (ko) | 2013-12-23 |
| AU2011295998A1 (en) | 2013-02-21 |
| AR082869A1 (es) | 2013-01-16 |
| TW201245155A (en) | 2012-11-16 |
| CN105130900A (zh) | 2015-12-09 |
| PL2611297T3 (pl) | 2015-11-30 |
| BR112013004835B1 (pt) | 2018-01-09 |
| EP2611297B1 (en) | 2015-06-17 |
| US9131693B2 (en) | 2015-09-15 |
| JP6066910B2 (ja) | 2017-01-25 |
| ES2546671T3 (es) | 2015-09-25 |
| US20140221448A1 (en) | 2014-08-07 |
| US20130143940A1 (en) | 2013-06-06 |
| US8754115B2 (en) | 2014-06-17 |
| WO2012030922A1 (en) | 2012-03-08 |
| MX2013002400A (es) | 2013-06-05 |
| BR112013004835A2 (pt) | 2016-05-31 |
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