CN114591230A - 一种环己烯酮类化合物及其应用和一种农药除草剂 - Google Patents
一种环己烯酮类化合物及其应用和一种农药除草剂 Download PDFInfo
- Publication number
- CN114591230A CN114591230A CN202210215391.3A CN202210215391A CN114591230A CN 114591230 A CN114591230 A CN 114591230A CN 202210215391 A CN202210215391 A CN 202210215391A CN 114591230 A CN114591230 A CN 114591230A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- compound
- group
- 400mhz
- 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.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 26
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 22
- -1 Cyclohexenone compound Chemical class 0.000 title claims abstract description 16
- 239000000575 pesticide Substances 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 241000196324 Embryophyta Species 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 240000007594 Oryza sativa Species 0.000 claims description 7
- 235000007164 Oryza sativa Nutrition 0.000 claims description 7
- 241000209140 Triticum Species 0.000 claims description 7
- 235000021307 Triticum Nutrition 0.000 claims description 7
- 230000000361 pesticidal effect Effects 0.000 claims description 7
- 235000009566 rice Nutrition 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 6
- 244000058871 Echinochloa crus-galli Species 0.000 claims description 5
- 240000008042 Zea mays Species 0.000 claims description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 235000005822 corn Nutrition 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 244000152970 Digitaria sanguinalis Species 0.000 claims description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 claims description 3
- 244000025670 Eleusine indica Species 0.000 claims description 3
- 235000014716 Eleusine indica Nutrition 0.000 claims description 3
- 241001553700 Euphorbia lathyris Species 0.000 claims description 3
- 235000014820 Galium aparine Nutrition 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 2
- 241000743985 Alopecurus Species 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000002574 poison Substances 0.000 claims description 2
- 231100000614 poison Toxicity 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 239000004563 wettable powder Substances 0.000 claims description 2
- 240000002791 Brassica napus Species 0.000 claims 1
- 235000006008 Brassica napus var napus Nutrition 0.000 claims 1
- 241000287127 Passeridae Species 0.000 claims 1
- 239000000428 dust Substances 0.000 claims 1
- 244000230342 green foxtail Species 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 238000009333 weeding Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 136
- 238000005160 1H NMR spectroscopy Methods 0.000 description 68
- 238000006243 chemical reaction Methods 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 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 3
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 3
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 description 3
- 108010018763 Biotin carboxylase Proteins 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 244000304962 green bristle grass Species 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000857 drug effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- 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 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- 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 1
- 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 1
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
- 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 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- 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 1
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- 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 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- 206010013709 Drug ineffective Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
- 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 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 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 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- 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 1
- 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 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 229940127113 compound 57 Drugs 0.000 description 1
- 229940125900 compound 59 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 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 1
- 230000002147 killing effect Effects 0.000 description 1
- 229940101629 l- methyl lactate Drugs 0.000 description 1
- 244000144886 lesser spear grass Species 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
-
- 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
- A01N43/06—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 five-membered rings
- A01N43/08—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 five-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/06—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 five-membered rings
- A01N43/10—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 five-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic 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
- A01N43/48—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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
-
- 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
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及农药除草剂领域，公开了一种环己烯酮类化合物及其应用和一种农药除草剂，该化合物具有式(I)所示的结构。本发明提供的环己烯酮类化合物具有优异的作物安全性和优异的除草效果。
Description
技术领域
本发明涉及农药化合物领域，具体涉及一种环己烯酮类化合物及其应用和一种除草剂。
背景技术
环己烯酮类除草剂是除草剂中非常重要的一类，此类除草剂最早开发于20世纪60年代，通过抑制乙酰辅酶A羧化酶(ACCase)，破坏脂肪酸的生物合成，来除掉杂草。此类除草剂是一种高效安全、高选择性的ACCase抑制剂，对于大多数一年生和多年生的禾本科杂草有特效，但有些在提高用量浓度时，会对水稻等农作物产生较严重的药害，因此一方面可以通过混合使用几种除草剂来解决这些问题，另一方面需要进一步地开展分子优化，以期获得更高活性的化合物，能够克服这些缺陷。
随着现有除草剂的大量使用，杂草抗性问题越来越严重，有些杂草已成为现有除草剂难以防除的杂草；同时，有些现有除草剂对作物的安全性不高，容易对作物造成要害，因此，需要不断开发新的、安全性高的除草剂。
发明内容
本发明为了弥补现有技术的不足，提供了一种除草活性高、对作物安全的环己烯酮类化合物及其制备方法与应用。
发明人发现，在环己烯酮的羟基上引入基团，能够提高本发明的化合物对水稻等作物的选择性，有利于增强化合物的作物安全性。
为了实现上述目的，本发明的第一方面提供一种羟基位置修饰的环己烯酮类化合物，该化合物具有式(I)所示的结构，
式(I)中，m个R各自独立地选自C1-6烷基、卤素、C1-6卤烷基、C1-6烷氧基、C1-6卤烷氧基、C1-6烯基、取代或未取代的苯基、取代或未取代的苯氧基、取代或未取代的苄氧基、取代或未取代的胺基、硝基、环己烷和硫烷基，m为0-5的整数；
R1选自H、C1-6烷基、取代或未取代的苄基、取代或未取代的烃基羰基、烷氧基羰基、苯基烷氧基羰基、苯氧基烷基羰基、烷基酯基羰基、取代或未取代的苯基羰基、取代或未取代的杂环基羰基和取代的磺酸基；
R2和R3各自独立的选自CH3、CH3CH2、CH3CH2CH2、(CH3)2CH2、CH3CH2CH2CH2、(CH3)2CH2CH2或CH3CH(CH3)CH2。
其优选的技术方案为：
m个R各自独立地选自卤素、C1-3卤烷基、C1-3烷氧基、C1-3卤烷氧基、C1-3烯基、取代或未取代的苯基(卤素或卤烷基取代)、取代或未取代的苯氧基(卤素或卤烷基取代)、取代或未取代的苄氧基(卤素或卤烷基取代)、取代或未取代的胺基、硝基、环己烷和硫烷基，m为0-5的整数；
R1选自H、C1-4烷基、取代或未取代的苄基(卤素或卤烷基取代)、取代或未取代的烃基羰基(卤素或卤烷基取代)、烷氧基羰基、苯基烷氧基羰基、苯氧基烷基羰基、烷基酯基羰基、卤素取代或未取代的苯基羰基、取代或未取代的杂环基羰基(杂环包括吡啶、吡唑、呋喃、四氢呋喃、噻吩和喹啉)和取代的磺酸基；
R2和R3各自独立的选自CH3、CH3CH2、CH3CH2CH2。
更优选的，该化合物选自以下化合物中的任意一种：
本发明对合成式(I)所示的环己烯酮类化合物的制备方法没有特别的限定，本领域技术人员根据本发明提供的化合物结构结合领域内的合成方法能够获得合适的制备式(I)所示的环己烯酮类化合物的方法，本发明在此不再一一赘述。
例如，本发明的通式(Ⅰ)化合物可由如下方法制备，式中R、R1、R2、R3基团定义同前。
当R1为前述取代基时，本发明化合物可以以I-1为原料，与相应的酰氯反应制得。反应可以在惰性溶剂中进行，在某些时候，可以加入无机碱如碳酸钠，或者有机碱如三乙胺等促进反应的完全。
本发明的第二方面提供第一方面所述的环己烯酮类化合物在防治田间农作物杂草中的应用。
在本发明的前述应用中，所述田间农作物为玉米，小麦、水稻、大豆和油菜中的至少一种。
在本发明的前述应用中，所述杂草包括狗尾草、稗草、千金子、马唐、节节麦、雀麦、看麦娘、牛筋草中的至少一种。
第三方面，本发明提供第一方面所述的环己烯酮类化合物作为农药除草剂的应用。
第四方面，本发明提供了一种农药除草剂，该除草剂由活性成分和辅料组成，所述活性成分包括本发明第一方面中所述的环己烯酮类化合物中的至少一种。
优选地，所述活性成分的含量为1～99.9999重量％。
优选地，所述辅料包括选自乳化剂、分散剂、润湿剂、展着剂、稳定剂、消泡剂、增效剂、渗透剂、粘着剂、防腐剂、抗冻剂、崩解剂、安全剂、溶剂、助溶剂、载体和填料中的至少一种添加剂。
优选情况下，所述农药除草剂的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、毒饵、母液和母粉中的至少一种。
所述悬浮剂例如可以包括干悬浮剂、可分散油悬浮剂和水乳剂。
本发明对制备所述农药除草剂的方法没有特别的限制，本领域技术人员可以采用农药领域内常规的制备方法进行制备以形成相应的试剂。
本发明所述的农药除草剂包括但不限于通过例如喷雾的方法用于农作物。
本发明提供的环己烯酮类化合物及含有该环己烯酮类化合物的农药除草剂具有该类除草剂的全部优点，并且具有环境友好，后茬作物安全、用量低、时效性好、杀草谱广、安全性高等优点。
特别地，本发明提供的环己烯酮类化合物对玉米、小麦和水稻表现出了优良的作物安全性。
以下将通过实例对本发明进行详细描述。
具体实施方式
下列合成实例、生测试验结果可用来进一步说明本发明，但不意味着限制本发明。
合成实例1：化合物22的合成
步骤1：
在5℃下，于1L反应瓶中加入对甲苯磺酸0.31mol、L-乳酸甲酯0.405mol、三乙胺0.325mol、4-二甲氨基吡啶0.015mol，300mL甲苯溶解，搅拌，缓慢升温至室温，继续搅拌。约4h后HPLC监控反应进度，反应完毕后，水洗，分层，脱溶，得中间体1，为红色液体78.5g，收率93.3％。
步骤2：
在20℃下，于500mL反应瓶中加入0.15mol中间体1、对氯苯酚0.15mol、无水碳酸钾0.3mol和240g石油醚，搅拌，缓慢升温至回流，回流保温8h后，HPLC监控反应进度，反应完毕后，水洗，分层，脱溶，得中间体2，为棕色液体50g，收率85.8％。
步骤3：
在10℃下，于500mL反应瓶中加入0.12mol中间体2、硼氢化钠0.25mol、无水氯化钙0.01mol、165g甲苯和165g乙醇，搅拌，缓慢升温至30℃，保温7h后，HPLC监控反应进度，反应完毕后，水洗，分层，脱溶，得中间体3，为棕色液体36g，收率88.1％。
步骤4：
在5℃下，于500mL反应瓶中加入0.08mol中间体3和150g甲苯，搅拌至全溶，在10℃下滴加入0.09mol三乙胺，滴毕，在20℃于1小时内滴加入0.09mol甲磺酰氯，滴完，缓慢升温至30℃，保温3h后，HPLC监控反应进度，反应完毕后，水洗，分层，脱溶，得中间体4，为褐色液体26g，收率84.4％。
步骤5：
在25℃下，于500mL反应瓶中加入0.07mol中间体4、0.08mol邻苯二甲酰亚胺、无水碳酸钠0.04mol、208g DMF，搅拌，升温至80℃，保温6h后，HPLC监控反应进度，反应完毕后，减压脱溶，加水，甲苯萃取，分层，水洗，分层，脱溶，得中间体3，为棕色液体33g，收率64.1％。
步骤6：
在5℃下，于500mL反应瓶中加入0.07mol中间体5和150g二氯甲烷，搅拌至全溶，在10℃下滴加入0.13mol水合肼，滴毕，在20℃保温5小时后，HPLC监控反应进度，反应完毕后，抽滤，二氯甲烷洗滤饼，抽滤，烘干得中间体6，白色固体7.5g，收率41.1％。
步骤7：
在15℃下，于100mL反应瓶中加入0.01mol中间体6、0.01mol丁酰三酮和30g石油醚，搅拌，升温至30℃，保温6h后，HPLC监控反应进度，反应完毕后，加水，分层，脱溶，得I-1，为棕色液体5.8g，收率88.9％。
步骤8：
于100mL反应瓶中加入0.03mol I-1、0.04mol三乙胺和50g二氯甲烷，搅拌，降温至0℃，滴加0.045mol乙酰氯，滴毕，缓慢自然升温至室温，保温1h，反应完毕后，加水，分层，无水硫酸镁干燥，过滤，母液脱溶，得化合物22，收率70.6％。
采用前述相似的方法合成本发明的其他化合物，部分化合物的表征数据如下：
化合物1：1H NMR(400MHz,CDCl3)δ8.92(s,1H),8.68(d,1H),7.35(d,2H),7.06(d,2H),7.49(m,1H),8.11(d,1H),1.68(m,1H),3.02-2.77(m,2H),2.32-2.07(m,2H),2.56(m,1H),2.51(m,2H),3.82(m,1H),4.28-3.98(m,2H),1.72(m,2H),2.33(t,2H),1.77(m,2H),1.50(d,3H),1.35(t,3H),1.53(d,3H),1.17(t,3H).
化合物2：1H NMR(400MHz,CDCl3)δ8.78(d,1H),7.52(d,2H),7.26(d,2H),7.97(m,1H),8.51(d,1H),1.78(m,1H),3.22-2.93(m,2H),2.22-2.05(m,2H),2.76(m,1H),2.71(m,2H),4.02(m,1H),4.22-4.00(m,2H),1.77(m,2H),2.39(t,2H),1.57(m,2H),1.52(d,3H),1.39(t,3H),1.58(d,3H),1.27(t,3H).
化合物3：1H NMR(400MHz,CDCl3)δ8.98(s,1H),8.74(s,1H),7.42(d,2H),7.20(d,2H),8.17(s,1H),1.88(m,1H),3.28-2.96(m,2H),2.12-1.96(m,2H),2.78(m,1H),2.69(m,2H),4.00(m,1H),4.17-3.90(m,2H),1.75(m,2H),2.37(s,3H),2.29(t,2H),1.60(m,2H),1.42(d,3H),1.35(t,3H),1.57(d,3H),1.17(t,3H).
化合物4：1H NMR(400MHz,CDCl3)δ8.96(s,1H),8.81(s,1H),7.37(d,2H),7.20(d,2H),8.21(s,1H),1.85(m,1H),3.26-2.92(m,2H),2.15-1.92(m,2H),2.76(m,1H),2.67(m,2H),4.01(m,1H),4.18-3.92(m,2H),2.78(m,2H),1.70(m,2H),2.27(t,2H),1.63(m,2H),1.41(d,3H),1.33(t,3H),1.52(d,3H),1.37(t,3H),1.18(t,3H).
化合物5：1H NMR(400MHz,CDCl3)δ8.95(s,1H),7.62(d,1H),7.42(d,2H),7.22(d,2H),8.40(d,1H),1.86(m,1H),3.27-2.94(m,2H),2.17-1.96(m,2H),2.75(m,1H),2.68(m,2H),4.02(m,1H),4.19-3.93(m,2H),1.71(m,2H),2.28(t,2H),1.66(m,2H),1.42(d,3H),1.34(t,3H),1.53(d,3H),1.19(t,3H).
化合物6：1H NMR(400MHz,CDCl3)δ8.96(s,1H),8.84(s,1H),7.42(d,2H),7.22(d,2H),8.41(s,1H),1.87(m,1H),3.28-2.96(m,2H),2.18-1.97(m,2H),2.76(m,1H),2.68(m,2H),4.92(s,2H),3.90(m,1H),4.19-3.92(m,2H),3.36(s,3H),1.71(m,2H),2.26(t,2H),1.65(m,2H),1.42(d,3H),1.34(t,3H),1.53(d,3H),1.18(t,3H).
化合物7：1H NMR(400MHz,CDCl3)δ8.98(d,1H),7.52(d,2H),7.23(d,2H),8.47(d,1H),8.18(m,2H),1.87(m,1H),3.28-2.96(m,2H),2.19-1.98(m,2H),2.77(m,1H),2.68(m,2H),4.02(m,1H),4.22-3.92(m,2H),1.72(m,2H),2.27(t,2H),1.66(m,2H),1.43(d,3H),1.35(t,3H),1.54(d,3H),1.19(t,3H).
化合物8：1H NMR(400MHz,CDCl3)δ8.96(d,2H),7.53(d,2H),7.23(d,2H),8.12(d,2H),1.86(m,1H),3.28-2.96(m,2H),2.19-1.98(m,2H),2.76(m,1H),2.67(m,2H),4.06(m,1H),4.22-3.93(m,2H),1.72(m,2H),2.26(t,2H),1.66(m,2H),1.45(d,3H),1.33(t,3H),1.55(d,3H),1.18(t,3H).
化合物9：1H NMR(400MHz,CDCl3)δ8.88(s,1H),8.02(s,1H),7.52(d,2H),7.22(d,2H),1.85(m,1H),3.27-2.96(m,2H),2.20-1.97(m,2H),2.75(m,1H),2.66(m,2H),4.02(m,1H),4.22-3.92(m,2H),4.12(s,3H),1.70(m,2H),2.22(t,2H),1.65(m,2H),1.44(d,3H),1.32(t,3H),1.53(d,3H),1.17(t,3H).
化合物10：1H NMR(400MHz,CDCl3)δ8.00(s,1H),7.51(d,2H),7.23(d,2H),1.86(m,1H),3.26-2.95(m,2H),2.21-1.98(m,2H),2.76(m,1H),2.65(m,2H),4.03(m,1H),4.23-3.93(m,2H),4.49(m,2H),3.57(s,3H),1.71(m,2H),2.21(t,2H),1.66(m,2H),1.43(d,3H),1.33(t,3H),1.50(d,3H),1.53(t,3H),1.18(t,3H).
化合物11：1H NMR(400MHz,CDCl3)δ7.40(s,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),4.09(s,3H),2.22(s,3H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物12：1H NMR(400MHz,CDCl3)δ7.41(s,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),4.10(m,2H),2.22(s,3H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.37(d,3H),1.16(t,3H).
化合物13：1H NMR(400MHz,CDCl3)δ7.87(d,1H),6.80(d,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),4.12(s,3H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物14：1H NMR(400MHz,CDCl3)δ7.88(d,1H),6.82(d,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),4.13(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.38(t,3H),1.16(t,3H).
化合物15：1H NMR(400MHz,CDCl3)δ8.01(d,1H),7.75(d,1H),6.81(m,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物16：1H NMR(400MHz,CDCl3)δ4.62(t,1H),3.86-3.75(m,2H),2.29-2.01(m,2H),1.95-1.84(m,2H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物17：1H NMR(400MHz,CDCl3)δ7.91(d,1H),8.07(d,1H),7.26(m,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物18：1H NMR(400MHz,CDCl3)δ9.37(s,1H),8.86(s,1H),8.47(d,1H),8.67(d,1H),7.94(m,1H),7.85(m,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物19：1H NMR(400MHz,CDCl3)δ8.21(d,2H),7.86(t,1H),7.68(m,2H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物20：1H NMR(400MHz,CDCl3)δ8.11(d,2H),7.78(d,2H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物21：1H NMR(400MHz,CDCl3)δ8.06(sd,2H),8.01(s,1H),7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物22：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),2.22(s,3H),1.43(d,3H),1.16(t,3H).
化合物23：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.46(m,2H),2.21(t,2H),1.65(m,2H),1.43(d,3H),1.30(t,3H),1.47(d,3H),1.22(t,3H),1.16(t,3H).
化合物24：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.36(t,2H),2.21(t,2H),1.65(m,2H),1.63(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.18(t,3H),1.16(t,3H).
化合物25：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.36(t,2H),2.21(t,2H),1.69(m,2H),1.62(m,2H),1.46(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.18(t,3H),1.13(t,3H).
化合物26：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.36(t,2H),2.21(t,2H),1.68(m,2H),1.36(m,2H),1.62(m,2H),1.34(m,2H),1.35(d,3H),1.30(t,3H),1.43(d,3H),1.18(t,3H),1.08(t,3H).
化合物27：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.46(m,1H),2.25(d,2H),2.21(t,2H),1.62(m,2H),1.34(d,3H),1.25(t,3H),1.43(d,3H),1.12(d,6H),1.18(t,3H).
化合物28：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),1.32(s,9H).
化合物29：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),1.30(s,6H),1.56(m,2H),0.96(t,3H).
化合物30：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),2.39(t,2H),1.56(m,2H),1.70(m,1H),0.99(d,6H).
化合物31：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),2.31-2.06(d,2H),2.19(m,1H),1.61(m,2H),1.05(t,3H),1.01(d,3H).
化合物32：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),2.20(m,1H),1.56(m,4H),1.37(m,4H),0.98(t,6H).
化合物33：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),2.19(m,1H),1.55(m,4H),1.02(t,6H).
化合物34：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),2.61(m,1H),1.15(d,6H).
化合物35：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),7.18(m,1H),6.06(d,1H),1.96(d,3H).
化合物36：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),6.00(m,1H),5.21(d,1H),4.96(m,1H),2.43(m,1H),2.37-2.12(m,2H),1.26(d,3H).
化合物37：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),3.76(t,2H),2.38(t,2H),1.92(m,2H).
化合物38：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),3.68(t,2H),2.38(t,2H),1.85(m,2H),1.60(m,2H).
化合物39：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),4.10(m,1H),2.66-2.39(d,2H),1.63(m,2H),0.97(t,3H).
化合物40：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),3.59(t,2H),2.39(t,2H),2.15(m,2H).
化合物41：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),3.86(t,2H),2.59(t,2H).
化合物42：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),4.49(m,1H),1.80(d,3H).
化合物43：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),3.61(s,2H),1.35(s,6H).
化合物44：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),4.40(s,2H).
化合物45：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H).
化合物46：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.97(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.40(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),7.50(s,4H),3.62(d,1H),2.39(m,1H),0.95(d,6H).
化合物47：1H NMR(400MHz,CDCl3)δ7.52(d,2H),7.23(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.96(m,2H),2.73(m,1H),2.63(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),1.43(d,3H),1.28(t,3H),1.52(d,3H),3.32(s,3H),16.86(s,1H).
化合物48：1H NMR(400MHz,CDCl3)δ7.52(d,2H),7.23(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.96(m,2H),2.73(m,1H),2.63(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),1.43(d,3H),1.28(t,3H),1.52(d,3H),2.36(m,2H),1.22(t,3H),16.86(s,1H).
化合物49：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),3.59(s,3H).
化合物50：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),4.10(m,2H),1.31(t,3H).
化合物51：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),4.00(m,1H),1.27(d,6H).
化合物52：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),1.42(s,9H).
化合物53：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.41(s,4H),7.40(d,1H),5.01(s,2H).
化合物54：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.54(s,1H),7.43(s,3H),5.00(s,2H).
化合物55：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.46(d,2H),7.30(d,2H),5.01(s,2H).
化合物56：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.62(d,2H),7.19(d,2H),5.00(s,2H).
化合物57：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),3.15(m,2H),1.41(t,3H).
化合物58：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.97(d,2H),7.91(d,1H),7.77(m,2H).
化合物59：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),1.58(s,2H).
化合物60：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.78(s,1H),7.57(s,1H),7.21(d,2H),6.90(d,2H),4.97(m,1H),1.65(d,3H).
化合物61：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.70(s,1H),7.51(d,1H),7.36(d,1H),6.95(d,2H),6.90(d,2H),4.97(m,1H),3.47(s,2H),1.65(d,3H).
化合物62：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.99(s,1H),7.78(s,1H),7.21(d,2H),6.90(d,2H),4.97(m,1H),1.66(d,3H).
化合物63：1H NMR(400MHz,CDCl3)δ7.49(d,2H),7.21(d,2H),1.84(m,1H),3.19-2.91(m,2H),2.19-1.95(m,2H),2.72(m,1H),2.63(m,2H),4.01(m,1H),4.20-3.90(m,2H),1.65(m,2H),2.20(t,2H),1.64(m,2H),1.38(d,3H),1.29(t,3H),1.42(d,3H),1.15(t,3H),7.46(s,1H),7.36(d,1H),7.20(d,1H),4.19(t,2H),2.37(t,2H),2.16(m,2H).
化合物64：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.96(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.39(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),4.09(m,2H),2.79(t,2H),2.69(t,2H),1.15(t,3H).
化合物65：1H NMR(400MHz,CDCl3)δ7.50(d,2H),7.22(d,2H),1.85(m,1H),3.20-2.92(m,2H),2.20-1.96(m,2H),2.73(m,1H),2.64(m,2H),4.02(m,1H),4.21-3.91(m,2H),1.66(m,2H),2.21(t,2H),1.65(m,2H),1.39(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),5.10(s,2H),2.27(s,3H).
化合物66：1H NMR(400MHz,CDCl3)δ7.51(d,2H),7.23(d,2H),1.86(m,1H),3.22-2.92(m,2H),2.21-1.96(m,2H),2.75(m,1H),2.65(m,2H),4.03(m,1H),4.23-3.91(m,2H),1.67(m,2H),2.22(t,2H),1.65(m,2H),1.39(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),3.87(s,3H).
化合物67：1H NMR(400MHz,CDCl3)δ7.51(d,2H),7.23(d,2H),1.86(m,1H),3.22-2.92(m,2H),2.21-1.96(m,2H),2.75(m,1H),2.65(m,2H),4.03(m,1H),4.23-3.91(m,2H),1.67(m,2H),2.22(t,2H),1.65(m,2H),1.39(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),4.30(t,2H),1.62(m,2H),1.47(m,2H),0.98(t,3H).
化合物68：1H NMR(400MHz,CDCl3)δ7.51(d,2H),7.23(d,2H),1.86(m,1H),3.22-2.92(m,2H),2.21-1.96(m,2H),2.75(m,1H),2.65(m,2H),4.03(m,1H),4.23-3.91(m,2H),1.67(m,2H),2.22(t,2H),1.65(m,2H),1.39(d,3H),1.30(t,3H),1.43(d,3H),1.16(t,3H),7.40(d,4H),7.39(d,1H),5.21(s,2H).
同已公开的化合物D1和D2相比，本发明如通式(Ⅰ)所示化合物不仅显示出高的除草活性，而且显示出意想不到的作物安全性，尤其对水稻、小麦、玉米等作物安全。因此本发明还包括通式(Ⅰ)所示化合物作为除草剂的用途。
生测实例2：除草活性和作物安全性的测定
初筛试验(盆栽法)：测试靶标为稗草、狗尾草、马唐、千金子和牛筋草。
苗后茎叶喷雾：取内径为7cm纸杯，装复合土(菜园土：育苗基质，1:2，v/v)至3/4处，直接播种杂草，覆土0.2cm，待长至4-5叶期备用。本发明的化合物和前述对比化合物按照5g.a.i./mu的剂量在自动喷雾塔施药后，待作物叶面药液晾干后移入温室培养(25度-28度，湿度70％)，30天后调查结果。其中对照化合物D1、D2的结构式如下所示：
生长抑制率评价方法为目测法，具体根据表1所示情况进行评级，测试结果如表2、表3所示。
表1
| (％) | 评价(抑制、畸形、白化等) | 生长抑制率级别 |
| 0-5 | 对杂草或作物生长无影响，无药效症状。 | 0 |
| 5-29 | 对杂草或作物生长有轻微影响，无明显药效症状 | 1 |
| 30-49 | 对杂草或作物生长有抑制，无明显药效症状。 | 2 |
| 50-69 | 对杂草或作物长有影响，有明显药效症状。 | 3 |
| 70-89 | 杂草或作物受到严重生长抑制。 | 4 |
| 90-100 | 杂草或作物死亡。 | 5 |
表2
表3：部分化合物对作物的安全性评价
由上述结果可知，本发明的化合物在除草测试实验中，对常见的禾本科杂草均表现出良好的除草活性，特别对稗草和狗尾草具有很好的防治效果。
同时，本发明的化合物对水稻、玉米和小麦安全，作物安全性明显优于对照化合物，能够用于水稻田防除稗草等恶性杂草。
以上详细描述了本发明的优选实施方式，但是，本发明并不限于此。在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，包括各个技术特征以任何其它的合适方式进行组合，这些简单变型和组合同样应当视为本发明所公开的内容，均属于本发明的保护范围。
Claims (9)
1.一种环己烯酮类化合物，该化合物具有式(I)所示的结构，
式(I)中，m个R各自独立地选自C1-6烷基、卤素、C1-6卤烷基、C1-6烷氧基、C1-6卤烷氧基、C1-6烯基、取代或未取代的苯基、取代或未取代的苯氧基、取代或未取代的苄氧基、取代或未取代的胺基、硝基、环己烷和硫烷基，m为0-5的整数；
R1选自H、C1-6烷基、取代或未取代的苄基、取代或未取代的烃基羰基、取代或未取代的烷氧基羰基、取代或未取代的苯基烷氧基羰基、取代或未取代的苯氧基烷基羰基、取代或未取代的烷基酯基羰基、取代或未取代的苯基羰基、取代或未取代的杂环基羰基和取代或未取代的磺酸基；
R2和R3各自独立的选自CH3、CH3CH2、CH3CH2CH2、(CH3)2CH2、CH3CH2CH2CH2、(CH3)2CH2CH2或CH3CH(CH3)CH2。
2.根据权利要求1所述的化合物，其中，在式(I)中，m个R各自独立地选自卤素、C1-3卤烷基、C1-3烷氧基、C1-3卤烷氧基、C1-3烯基、取代或未取代的苯基(卤素或卤烷基取代)、取代或未取代的苯氧基(卤素或卤烷基取代)、取代或未取代的苄氧基(卤素或卤烷基取代)、取代或未取代的胺基、硝基、环己烷和硫烷基，m为0-5的整数；
R1选自H、C1-4烷基、取代或未取代的苄基(卤素或卤烷基取代)、取代或未取代的烃基羰基(卤素或卤烷基取代)、烷氧基羰基、苯基烷氧基羰基、苯氧基烷基羰基、烷基酯基羰基、卤素取代或未取代的苯基羰基、取代或未取代的杂环基羰基(杂环包括吡啶、吡唑、呋喃、四氢呋喃、噻吩和喹啉)和取代的磺酸基；
R2和R3各自独立的选自CH3、CH3CH2、CH3CH2CH2。
3.根据权利要求1或2所述的化合物，其中，所述环己烯酮类化合物选自以下化合物中的至少一种：
4.权利要求1-3中任意一项所述的环己烯酮类化合物在防治田间农作物杂草中的应用。
5.根据权利要求4所述的应用，其中，所述田间农作物为玉米，小麦、水稻、大豆和油菜中的至少一种。所述杂草包括狗尾草、稗草、千金子、马唐、节节麦、雀麦、看麦娘、牛筋草中的至少一种。
6.权利要求1-3中任意一项所述的环己烯酮类化合物作为农药除草剂的应用。
7.一种农药除草剂，该除草剂由活性成分和辅料组成，所述活性成分包括权利要求1-3中所述的环己烯酮类化合物中的至少一种。
8.根据权利要求7所述的农药除草剂，其中，所述活性成分的含量为1～99.9999重量％。
9.根据权利要求7或8所述的农药除草剂，其中，所述农药除草剂的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、毒饵、母液和母粉中的至少一种。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210215391.3A CN114591230A (zh) | 2022-03-07 | 2022-03-07 | 一种环己烯酮类化合物及其应用和一种农药除草剂 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210215391.3A CN114591230A (zh) | 2022-03-07 | 2022-03-07 | 一种环己烯酮类化合物及其应用和一种农药除草剂 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114591230A true CN114591230A (zh) | 2022-06-07 |
Family
ID=81815115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210215391.3A Pending CN114591230A (zh) | 2022-03-07 | 2022-03-07 | 一种环己烯酮类化合物及其应用和一种农药除草剂 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114591230A (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115735919A (zh) * | 2022-11-21 | 2023-03-07 | 郑州手性药物研究院有限公司 | 一种含环己烷-1，3-二酮衍生物的除草剂组合物及其应用 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993016033A1 (de) * | 1992-02-13 | 1993-08-19 | Basf Aktiengesellschaft | Cyclohexenonoximether, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| WO1993016062A1 (de) * | 1992-02-13 | 1993-08-19 | Basf Aktiengesellschaft | Mischungen aus optisch aktiven cyclohexenonoximethern, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| US5605875A (en) * | 1994-06-03 | 1997-02-25 | Basf Aktiengesellschaft | Herbicidal compositions comprising 3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)- and/or 1-(methyl-1-phenylethyl)-3(-4-tolyl)urea and at least one cyclohexenone oxime ether |
| CN1200649A (zh) * | 1995-09-20 | 1998-12-02 | 巴斯福股份公司 | 包含环己烯酮肟醚的增效除草混合物 |
| CN105884665A (zh) * | 2016-04-21 | 2016-08-24 | 潍坊先达化工有限公司 | 一种环己烯酮类化合物及其制备方法与应用 |
| CN112655710A (zh) * | 2020-04-10 | 2021-04-16 | 辽宁先达农业科学有限公司 | 农药组合物及其应用和除草剂 |
| CN112674096A (zh) * | 2020-12-31 | 2021-04-20 | 山东先达农化股份有限公司 | 一种液体除草剂组合物及其应用 |
| CN114105842A (zh) * | 2020-08-28 | 2022-03-01 | 郑州手性药物研究院有限公司 | 环己二烯肟醚类化合物及其应用 |
-
2022
- 2022-03-07 CN CN202210215391.3A patent/CN114591230A/zh active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993016033A1 (de) * | 1992-02-13 | 1993-08-19 | Basf Aktiengesellschaft | Cyclohexenonoximether, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| WO1993016062A1 (de) * | 1992-02-13 | 1993-08-19 | Basf Aktiengesellschaft | Mischungen aus optisch aktiven cyclohexenonoximethern, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| US5605875A (en) * | 1994-06-03 | 1997-02-25 | Basf Aktiengesellschaft | Herbicidal compositions comprising 3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)- and/or 1-(methyl-1-phenylethyl)-3(-4-tolyl)urea and at least one cyclohexenone oxime ether |
| CN1200649A (zh) * | 1995-09-20 | 1998-12-02 | 巴斯福股份公司 | 包含环己烯酮肟醚的增效除草混合物 |
| CN105884665A (zh) * | 2016-04-21 | 2016-08-24 | 潍坊先达化工有限公司 | 一种环己烯酮类化合物及其制备方法与应用 |
| CN112655710A (zh) * | 2020-04-10 | 2021-04-16 | 辽宁先达农业科学有限公司 | 农药组合物及其应用和除草剂 |
| CN114105842A (zh) * | 2020-08-28 | 2022-03-01 | 郑州手性药物研究院有限公司 | 环己二烯肟醚类化合物及其应用 |
| CN112674096A (zh) * | 2020-12-31 | 2021-04-20 | 山东先达农化股份有限公司 | 一种液体除草剂组合物及其应用 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115735919A (zh) * | 2022-11-21 | 2023-03-07 | 郑州手性药物研究院有限公司 | 一种含环己烷-1，3-二酮衍生物的除草剂组合物及其应用 |
| CN115735919B (zh) * | 2022-11-21 | 2024-04-26 | 郑州手性药物研究院有限公司 | 一种含环己烷-1，3-二酮衍生物的除草剂组合物及其应用 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2552811B2 (ja) | 殺虫作用のあるフェニルヒドラジン誘導体 | |
| US4878942A (en) | Benzamide derivative, process for its production and plant growth regulant | |
| US4943309A (en) | Method of defoleating cotton plants employing 3-carbonylphenyl uracil derivatives | |
| WO1999045774A1 (fr) | Agent regulant la croissance de vegetaux | |
| CN105732489B (zh) | 含吡啶二芳胺结构的氰基丙烯酸酯化合物的制备和应用 | |
| US4554017A (en) | Method and compositions for regulating plant growth using cycloalkane-carboxylic acid compounds | |
| CN111410630B (zh) | 一种含三氟甲基吡啶氧基芳基单元的氰基丙烯酸酯衍生物的制备和应用 | |
| CN114591230A (zh) | 一种环己烯酮类化合物及其应用和一种农药除草剂 | |
| CN110746356B (zh) | 含3-三氟甲基-5-氯吡唑结构的二氟甲基吡唑肟酯的制备方法和用途 | |
| CN110845478B (zh) | 含1-取代吡啶基-3-三氟甲基吡唑单元的吡唑甲酰肟衍生物的制备和用途 | |
| CN110804040B (zh) | 含二氟甲基吡唑联吡啶基的吡唑肟化合物的制备方法和用途 | |
| CN107602494B (zh) | 含四氮唑基团的氰基丙烯酸酯衍生物的制备和应用 | |
| JPS62132804A (ja) | 植物生長調節剤 | |
| US5176735A (en) | Method of desiccating plants employing 3-carbonylphenyl uracil derivatives | |
| CN111333569B (zh) | 含5-三氟甲基-3-氯吡啶联芳氧基单元的氰基丙烯酸酯的制备方法和用途 | |
| CN110776463B (zh) | 含3-三氟甲基吡唑的吡唑肟类衍生物的制备和应用 | |
| GB2101600A (en) | 2,4-Hexadienoic acid derivatives useful as weed-killers and phytogrowth regulators | |
| EP0181494A1 (en) | Plant growth regulation agent | |
| CN110845412B (zh) | 含1-甲基-3-二氟甲基-5-氯吡唑单元的吡唑肟化合物的制备和应用 | |
| CN110669008A (zh) | 含吡唑结构的1-甲基-3-芳基-4-氯吡唑-5-酰胺化合物的制备和应用 | |
| JP2522807B2 (ja) | シクロヘキセノン誘導体及び該化合物を含有する植物生長調整剤 | |
| US4340765A (en) | 4-Phenoxy-2-butene derivatives as plant growth regulators | |
| CS261895B2 (en) | Agent for plants growth regulation and method of efficient substance production | |
| CN112125912B (zh) | 一种含3-芳基噁二唑结构的磺酰胺类衍生物及其制备方法和应用 | |
| CN111925359B (zh) | 含1,3-二取代基吡唑基团的吡唑类衍生物的制备方法与用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |