OA21190A - Carboxylic acid derivative-substituted imino aryl compound, preparation method therefor, herbicidal composition and use thereof. - Google Patents
Carboxylic acid derivative-substituted imino aryl compound, preparation method therefor, herbicidal composition and use thereof. Download PDFInfo
- Publication number
- OA21190A OA21190A OA1202200177 OA21190A OA 21190 A OA21190 A OA 21190A OA 1202200177 OA1202200177 OA 1202200177 OA 21190 A OA21190 A OA 21190A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- cycloalkyl
- substituted
- halo
- alkynyl
- Prior art date
Links
- -1 imino aryl compound Chemical class 0.000 title claims abstract description 86
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 32
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 148
- 150000002367 halogens Chemical class 0.000 claims abstract description 148
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 100
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 30
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
- 239000000460 chlorine Substances 0.000 claims description 935
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 183
- 125000000623 heterocyclic group Chemical group 0.000 claims description 141
- 125000003118 aryl group Chemical group 0.000 claims description 126
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 107
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 105
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 75
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 73
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 72
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 70
- 125000004043 oxo group Chemical group O=* 0.000 claims description 68
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 125000003342 alkenyl group Chemical group 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 47
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 34
- 239000003112 inhibitor Substances 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 239000002689 soil Substances 0.000 claims description 24
- 239000004009 herbicide Substances 0.000 claims description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 20
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 18
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 18
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 230000012010 growth Effects 0.000 claims description 14
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 8
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 7
- 239000005531 Flufenacet Substances 0.000 claims description 7
- 239000005574 MCPA Substances 0.000 claims description 7
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 claims description 6
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 6
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 claims description 6
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- IUFUITYPUYMIHI-UHFFFAOYSA-N N-[1-(3,5-dimethylphenoxy)propan-2-yl]-6-(2-fluoropropan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N)=NC(C(C)(C)F)=NC=1NC(C)COC1=CC(C)=CC(C)=C1 IUFUITYPUYMIHI-UHFFFAOYSA-N 0.000 claims description 6
- IHHMUBRVTJMLQO-UHFFFAOYSA-N Pyraclonil Chemical compound C#CCN(C)C1=C(C#N)C=NN1C1=NN(CCCC2)C2=C1Cl IHHMUBRVTJMLQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 claims description 6
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 6
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 6
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 6
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 6
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 6
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 claims description 6
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 6
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims description 6
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 claims description 6
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims description 6
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims description 6
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 claims description 6
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 claims description 6
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 claims description 6
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 claims description 6
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims description 6
- VCPBNCQKRQSUFX-UHFFFAOYSA-N (5-iodopyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane Chemical compound IC1=CN=C2N([Si](C(C)C)(C(C)C)C(C)C)C=CC2=C1 VCPBNCQKRQSUFX-UHFFFAOYSA-N 0.000 claims description 5
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 claims description 5
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 claims description 5
- UFAPVJDEYHLLBG-UHFFFAOYSA-N 2-{2-chloro-4-(methylsulfonyl)-3-[(tetrahydrofuran-2-ylmethoxy)methyl]benzoyl}cyclohexane-1,3-dione Chemical compound ClC1=C(COCC2OCCC2)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O UFAPVJDEYHLLBG-UHFFFAOYSA-N 0.000 claims description 5
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 claims description 5
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005476 Bentazone Substances 0.000 claims description 5
- 239000005489 Bromoxynil Substances 0.000 claims description 5
- 239000005497 Clethodim Substances 0.000 claims description 5
- 239000005499 Clomazone Substances 0.000 claims description 5
- 239000005500 Clopyralid Substances 0.000 claims description 5
- 239000005503 Desmedipham Substances 0.000 claims description 5
- 239000005504 Dicamba Substances 0.000 claims description 5
- 239000005558 Fluroxypyr Substances 0.000 claims description 5
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims description 5
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims description 5
- 239000005591 Pendimethalin Substances 0.000 claims description 5
- 239000005594 Phenmedipham Substances 0.000 claims description 5
- 239000005595 Picloram Substances 0.000 claims description 5
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims description 5
- 239000005603 Prosulfocarb Substances 0.000 claims description 5
- 239000005617 S-Metolachlor Substances 0.000 claims description 5
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 claims description 5
- 239000005621 Terbuthylazine Substances 0.000 claims description 5
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 claims description 5
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 5
- FHUKASKVKWSLCY-UHFFFAOYSA-N bixlozone Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Cl)C=C1Cl FHUKASKVKWSLCY-UHFFFAOYSA-N 0.000 claims description 5
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 5
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 5
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 5
- WNZCDFOXYNRBRB-UHFFFAOYSA-N florpyrauxifen-benzyl Chemical group COC1=C(Cl)C=CC(C=2C(=C(N)C(Cl)=C(C(=O)OCC=3C=CC=CC=3)N=2)F)=C1F WNZCDFOXYNRBRB-UHFFFAOYSA-N 0.000 claims description 5
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 5
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical group NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 claims description 5
- YFONKFDEZLYQDH-BOURZNODSA-N indaziflam Chemical compound CC(F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-BOURZNODSA-N 0.000 claims description 5
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 5
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims description 5
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 5
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 5
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 5
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 claims description 5
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 5
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 5
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 claims description 5
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000005468 Aminopyralid Substances 0.000 claims description 4
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 4
- 239000005494 Chlorotoluron Substances 0.000 claims description 4
- 239000005507 Diflufenican Substances 0.000 claims description 4
- 239000005559 Flurtamone Substances 0.000 claims description 4
- 239000005562 Glyphosate Substances 0.000 claims description 4
- 239000005563 Halauxifen-methyl Substances 0.000 claims description 4
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 claims description 4
- 239000005566 Imazamox Substances 0.000 claims description 4
- 239000005571 Isoxaflutole Substances 0.000 claims description 4
- 239000005583 Metribuzin Substances 0.000 claims description 4
- 239000005586 Nicosulfuron Substances 0.000 claims description 4
- 239000005588 Oxadiazon Substances 0.000 claims description 4
- 239000005590 Oxyfluorfen Substances 0.000 claims description 4
- 239000005596 Picolinafen Substances 0.000 claims description 4
- 239000005616 Rimsulfuron Substances 0.000 claims description 4
- 239000005620 Tembotrione Substances 0.000 claims description 4
- 239000005627 Triclopyr Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229940097068 glyphosate Drugs 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 229940088649 isoxaflutole Drugs 0.000 claims description 4
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 claims description 4
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 claims description 4
- 239000005564 Halosulfuron methyl Substances 0.000 claims description 3
- ZBMRKNMTMPPMMK-WCCKRBBISA-N glufosinate-P-ammonium Chemical compound N.CP(O)(=O)CC[C@H](N)C(O)=O ZBMRKNMTMPPMMK-WCCKRBBISA-N 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- AJPADPZSRRUGHI-RFZPGFLSSA-N 1-deoxy-D-xylulose 5-phosphate Chemical compound CC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O AJPADPZSRRUGHI-RFZPGFLSSA-N 0.000 claims description 2
- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 claims description 2
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 2
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 2
- 108010018763 Biotin carboxylase Proteins 0.000 claims description 2
- 102000029749 Microtubule Human genes 0.000 claims description 2
- 108091022875 Microtubule Proteins 0.000 claims description 2
- 101100339555 Zymoseptoria tritici HPPD gene Proteins 0.000 claims description 2
- 150000001264 acyl cyanides Chemical class 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004967 formylalkyl group Chemical group 0.000 claims description 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 239000003688 hormone derivative Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 210000004688 microtubule Anatomy 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000002905 orthoesters Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000007970 thio esters Chemical class 0.000 claims description 2
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 2
- IQWMUTFHGXREBR-UHFFFAOYSA-N 2-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3-yl)-2,4-dichlorophenoxy]acetonitrile Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#N)=C(Cl)C=C1Cl IQWMUTFHGXREBR-UHFFFAOYSA-N 0.000 claims 1
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 97
- 239000000575 pesticide Substances 0.000 abstract description 5
- 241000234646 Cyperaceae Species 0.000 abstract description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 175
- YGPZYYDTPXVBRA-RTDBHSBRSA-N [(2r,3s,4r,5r,6s)-2-[[(2r,3r,4r,5s,6r)-3-[[(3r)-3-dodecanoyloxytetradecanoyl]amino]-6-(hydroxymethyl)-5-phosphonooxy-4-[(3r)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-3,6-dihydroxy-5-[[(3r)-3-hydroxytetradecanoyl]amino]oxan-4-yl] (3r)-3-hydr Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](O)O1 YGPZYYDTPXVBRA-RTDBHSBRSA-N 0.000 description 71
- 239000000243 solution Substances 0.000 description 67
- 230000000694 effects Effects 0.000 description 31
- 239000007787 solid Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 26
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 238000004440 column chromatography Methods 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000002994 raw material Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 230000009261 transgenic effect Effects 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 241000192043 Echinochloa Species 0.000 description 13
- 240000007594 Oryza sativa Species 0.000 description 13
- 235000007164 Oryza sativa Nutrition 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- 235000009566 rice Nutrition 0.000 description 13
- 239000008187 granular material Substances 0.000 description 12
- 239000007921 spray Substances 0.000 description 12
- 244000286838 Eclipta prostrata Species 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 235000017680 Descurainia sophia Nutrition 0.000 description 9
- 244000264242 Descurainia sophia Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 244000038559 crop plants Species 0.000 description 8
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 244000058871 Echinochloa crus-galli Species 0.000 description 7
- 244000299507 Gossypium hirsutum Species 0.000 description 7
- 244000143149 Leptochloa chinensis Species 0.000 description 7
- 241000318694 Myosoton aquaticum Species 0.000 description 7
- 235000011999 Panicum crusgalli Nutrition 0.000 description 7
- 244000085269 Scirpus juncoides Species 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 239000004562 water dispersible granule Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 240000000178 Monochoria vaginalis Species 0.000 description 6
- 235000015909 Sagittaria sinensis Nutrition 0.000 description 6
- 240000004519 Sagittaria trifolia Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 5
- 244000237956 Amaranthus retroflexus Species 0.000 description 5
- 235000000621 Bidens tripartita Nutrition 0.000 description 5
- 240000004082 Bidens tripartita Species 0.000 description 5
- 241000234653 Cyperus Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- SILSDTWXNBZOGF-KUZBFYBWSA-N chembl111058 Chemical compound CCSC(C)CC1CC(O)=C(\C(CC)=N\OC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-KUZBFYBWSA-N 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 230000008034 disappearance Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000009333 weeding Methods 0.000 description 5
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 description 4
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 241000237537 Ensis Species 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 101100221809 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cpd-7 gene Proteins 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000003337 fertilizer Substances 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- 235000014716 Eleusine indica Nutrition 0.000 description 3
- 244000025670 Eleusine indica Species 0.000 description 3
- 241001299722 Eriochloa villosa Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 108091028043 Nucleic acid sequence Proteins 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010353 genetic engineering Methods 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 description 3
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- OOHIAOSLOGDBCE-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(Cl)=NC(NC2CC2)=N1 OOHIAOSLOGDBCE-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 241001573870 Alopecurus japonicus Species 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 244000157790 Buglossoides arvense Species 0.000 description 2
- 235000004256 Buglossoides arvense Nutrition 0.000 description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 2
- 240000008867 Capsella bursa-pastoris Species 0.000 description 2
- 108091026890 Coding region Proteins 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 235000004385 Conyza canadensis Nutrition 0.000 description 2
- 244000074881 Conyza canadensis Species 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 241001521729 Eleusis Species 0.000 description 2
- 241001101998 Galium Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000005584 Metsulfuron-methyl Substances 0.000 description 2
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000005585 Napropamide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000005602 Propyzamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- 240000003461 Setaria viridis Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 description 2
- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000002301 combined effect Effects 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 description 2
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- ZCNQYNHDVRPZIH-UHFFFAOYSA-N fluthiacet-methyl Chemical group C1=C(Cl)C(SCC(=O)OC)=CC(N=C2N3CCCCN3C(=O)S2)=C1F ZCNQYNHDVRPZIH-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 230000004807 localization Effects 0.000 description 2
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 2
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 2
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1r,5s)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 description 1
- SESJCOBCXSACPH-UHFFFAOYSA-N (2,3-dichlorophenyl)methyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=CC(Cl)=C1Cl SESJCOBCXSACPH-UHFFFAOYSA-N 0.000 description 1
- DQKWXTIYGWPGOO-UHFFFAOYSA-N (2,6-dibromo-4-cyanophenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=C(Br)C=C(C#N)C=C1Br DQKWXTIYGWPGOO-UHFFFAOYSA-N 0.000 description 1
- HEJVROKEIMJTIN-UHFFFAOYSA-N (2-butan-2-yl-4,6-dinitrophenyl) (2,4-dinitrophenyl) carbonate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HEJVROKEIMJTIN-UHFFFAOYSA-N 0.000 description 1
- QWZIGUJYMLBQCY-UHFFFAOYSA-N (2-chloro-3,5-diiodopyridin-4-yl) acetate Chemical compound CC(=O)OC1=C(I)C=NC(Cl)=C1I QWZIGUJYMLBQCY-UHFFFAOYSA-N 0.000 description 1
- BMJYKXALMDAIEG-UHFFFAOYSA-N (2-tert-butyl-4,6-dinitrophenyl) acetate Chemical compound CC(=O)OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(C)(C)C BMJYKXALMDAIEG-UHFFFAOYSA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- XJPOOEMIUDHWSO-PHIMTYICSA-N (2s,5r)-2,5-dimethyl-n-phenylpyrrolidine-1-carboxamide Chemical compound C[C@H]1CC[C@@H](C)N1C(=O)NC1=CC=CC=C1 XJPOOEMIUDHWSO-PHIMTYICSA-N 0.000 description 1
- GGQDJKYTNRIKQS-UHFFFAOYSA-N (4-cyano-2,6-diiodophenyl) prop-2-enyl carbonate Chemical compound IC1=CC(C#N)=CC(I)=C1OC(=O)OCC=C GGQDJKYTNRIKQS-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ADDQHLREJDZPMT-AWEZNQCLSA-N (S)-metamifop Chemical compound O=C([C@@H](OC=1C=CC(OC=2OC3=CC(Cl)=CC=C3N=2)=CC=1)C)N(C)C1=CC=CC=C1F ADDQHLREJDZPMT-AWEZNQCLSA-N 0.000 description 1
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 description 1
- PYKLUAIDKVVEOS-RAXLEYEMSA-N (e)-n-(cyanomethoxy)benzenecarboximidoyl cyanide Chemical compound N#CCO\N=C(\C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-RAXLEYEMSA-N 0.000 description 1
- IBHCSFXTRODDNR-CYBMUJFWSA-N (propan-2-ylideneamino) (2r)-2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)ON=C(C)C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 IBHCSFXTRODDNR-CYBMUJFWSA-N 0.000 description 1
- RRLHZVASKJLNFJ-UPHRSURJSA-N (z)-2,3,5,5,5-pentachloro-4-oxopent-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(\Cl)C(=O)C(Cl)(Cl)Cl RRLHZVASKJLNFJ-UPHRSURJSA-N 0.000 description 1
- FCAKZZMVXCLLHM-UHFFFAOYSA-N 1,1-dimethyl-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]urea Chemical compound CN(C)C(=O)NC1=CC=CC(OC(F)(F)C(F)F)=C1 FCAKZZMVXCLLHM-UHFFFAOYSA-N 0.000 description 1
- MVHWKYHDYCGNQN-UHFFFAOYSA-N 1,5-dichloro-3-fluoro-2-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(F)C=C(Cl)C=C1Cl MVHWKYHDYCGNQN-UHFFFAOYSA-N 0.000 description 1
- IHSBKMBNDURWAT-UHFFFAOYSA-N 1-(1,1,4-trimethyl-6-propan-2-yl-2,3-dihydroinden-5-yl)propan-1-one Chemical compound C1=C(C(C)C)C(C(=O)CC)=C(C)C2=C1C(C)(C)CC2 IHSBKMBNDURWAT-UHFFFAOYSA-N 0.000 description 1
- DHYXNIKICPUXJI-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-(2,4-difluorophenyl)-5-oxo-n-propan-2-yl-1,2,4-triazole-4-carboxamide Chemical compound C=1C=C(F)C=C(F)C=1N(C(C)C)C(=O)N(C1=O)C=NN1C1=CC=C(Cl)C=C1Cl DHYXNIKICPUXJI-UHFFFAOYSA-N 0.000 description 1
- PYCINWWWERDNKE-UHFFFAOYSA-N 1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound N12N=C(CCC)C=CC2=NC(Cl)=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 PYCINWWWERDNKE-UHFFFAOYSA-N 0.000 description 1
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 1
- OPCMVVKRCLOEDQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(methylamino)pentan-1-one Chemical compound ClC1=CC=C(C=C1)C(C(CCC)NC)=O OPCMVVKRCLOEDQ-UHFFFAOYSA-N 0.000 description 1
- GUGLRTKPJBGNAF-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-methylurea Chemical compound CNC(=O)NC=1C=C(C(C)(C)C)ON=1 GUGLRTKPJBGNAF-UHFFFAOYSA-N 0.000 description 1
- IXWKBUKANTXHJH-UHFFFAOYSA-N 1-[5-chloro-2-methyl-4-(5-methyl-5,6-dihydro-1,4,2-dioxazin-3-yl)pyrazol-3-yl]sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C=2OC(C)CON=2)C)=N1 IXWKBUKANTXHJH-UHFFFAOYSA-N 0.000 description 1
- KOKBUARVIJVMMM-UHFFFAOYSA-N 1-amino-3-(2,2-dimethylpropyl)-6-ethylsulfanyl-1,3,5-triazine-2,4-dione Chemical compound CCSC1=NC(=O)N(CC(C)(C)C)C(=O)N1N KOKBUARVIJVMMM-UHFFFAOYSA-N 0.000 description 1
- WLKSPGHQGFFKGE-UHFFFAOYSA-N 1-chloropropan-2-yl n-(3-chlorophenyl)carbamate Chemical compound ClCC(C)OC(=O)NC1=CC=CC(Cl)=C1 WLKSPGHQGFFKGE-UHFFFAOYSA-N 0.000 description 1
- UUHXXNQVWVFJLW-UHFFFAOYSA-N 1-dimethoxyphosphorylethyl 2-(2,4-dichlorophenoxy)acetate Chemical compound COP(=O)(OC)C(C)OC(=O)COC1=CC=C(Cl)C=C1Cl UUHXXNQVWVFJLW-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- DLKBRTKDSDXWNA-UHFFFAOYSA-N 1-methyl-3-(4-nitrophenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=CC(=CC=2)[N+]([O-])=O)=C1 DLKBRTKDSDXWNA-UHFFFAOYSA-N 0.000 description 1
- QZEKHJXYZSJVCL-UHFFFAOYSA-N 2,2,3-trichloropropanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCl QZEKHJXYZSJVCL-UHFFFAOYSA-N 0.000 description 1
- ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 description 1
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
- PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 1
- HSUOFZJUZZRIOL-LBPRGKRZSA-N 2,6-dimethyl-n-[(1s)-1-phenylethyl]-5-propanoylpyridine-3-carboxamide Chemical compound N1=C(C)C(C(=O)CC)=CC(C(=O)N[C@@H](C)C=2C=CC=CC=2)=C1C HSUOFZJUZZRIOL-LBPRGKRZSA-N 0.000 description 1
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 description 1
- IUQJDHJVPLLKFL-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetate;dimethylazanium Chemical compound CNC.OC(=O)COC1=CC=C(Cl)C=C1Cl IUQJDHJVPLLKFL-UHFFFAOYSA-N 0.000 description 1
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- MAYMYMXYWIVVOK-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(CNS(C)(=O)=O)C=2)C(O)=O)=N1 MAYMYMXYWIVVOK-UHFFFAOYSA-N 0.000 description 1
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 description 1
- OVQJTYOXWVHPTA-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitropyrazol-3-amine Chemical compound NC1=C([N+]([O-])=O)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl OVQJTYOXWVHPTA-UHFFFAOYSA-N 0.000 description 1
- KQUYPOJCTWSLSE-UHFFFAOYSA-N 2-[4-[1-[2-(diethylamino)-2-oxoethyl]pyridin-1-ium-4-yl]pyridin-1-ium-1-yl]-n,n-diethylacetamide Chemical compound C1=C[N+](CC(=O)N(CC)CC)=CC=C1C1=CC=[N+](CC(=O)N(CC)CC)C=C1 KQUYPOJCTWSLSE-UHFFFAOYSA-N 0.000 description 1
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
- WUZNHSBFPPFULJ-UHFFFAOYSA-N 2-[[4-chloro-6-(cyclopropylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropanenitrile Chemical compound N#CC(C)(C)NC1=NC(Cl)=NC(NC2CC2)=N1 WUZNHSBFPPFULJ-UHFFFAOYSA-N 0.000 description 1
- RCOHXZITQFQFRZ-UHFFFAOYSA-N 2-[n-[2-(3,5-dichloro-2-methoxybenzoyl)oxyethyl]anilino]ethyl 3,6-dichloro-2-methoxybenzoate Chemical compound COC1=C(Cl)C=C(Cl)C=C1C(=O)OCCN(C=1C=CC=CC=1)CCOC(=O)C1=C(Cl)C=CC(Cl)=C1OC RCOHXZITQFQFRZ-UHFFFAOYSA-N 0.000 description 1
- WDRGQGLIUAMOOC-UHFFFAOYSA-N 2-benzamidooxyacetic acid Chemical compound OC(=O)CONC(=O)C1=CC=CC=C1 WDRGQGLIUAMOOC-UHFFFAOYSA-N 0.000 description 1
- IVDRCZNHVGQBHZ-UHFFFAOYSA-N 2-butoxyethyl 2-(3,5,6-trichloropyridin-2-yl)oxyacetate Chemical group CCCCOCCOC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl IVDRCZNHVGQBHZ-UHFFFAOYSA-N 0.000 description 1
- ZGGSVBWJVIXBHV-UHFFFAOYSA-N 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl ZGGSVBWJVIXBHV-UHFFFAOYSA-N 0.000 description 1
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 1
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- UDRNNGBAXFCBLJ-UHFFFAOYSA-N 2-chloro-n-(2,3-dimethylphenyl)-n-propan-2-ylacetamide Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC(C)=C1C UDRNNGBAXFCBLJ-UHFFFAOYSA-N 0.000 description 1
- KZNDFYDURHAESM-UHFFFAOYSA-N 2-chloro-n-(2-ethyl-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl KZNDFYDURHAESM-UHFFFAOYSA-N 0.000 description 1
- QJTJSFKYIUWWJE-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-(2-ethylphenyl)acetamide Chemical compound CCOCN(C(=O)CCl)C1=CC=CC=C1CC QJTJSFKYIUWWJE-UHFFFAOYSA-N 0.000 description 1
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 1
- FYEWDLAVQKIKQE-UHFFFAOYSA-N 2-methyl-4-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazinane-3,5-dione Chemical compound O=C1N(C)OCC(=O)N1C1=CC=CC(C(F)(F)F)=C1 FYEWDLAVQKIKQE-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- QOBMKVRRANLSMZ-WJZAEVBBSA-N 3(1+2)-(3a,4,5,6,7,7a-hexahydro-4,7-methanoindanyl)-1,1-dimethylurea Chemical compound C1C[C@H]2C3C(NC(=O)N(C)C)CCC3[C@@H]1C2 QOBMKVRRANLSMZ-WJZAEVBBSA-N 0.000 description 1
- WCYYAQFQZQEUEN-UHFFFAOYSA-N 3,5,6-trichloropyridine-2-one Chemical compound ClC=1C=C(Cl)C(=O)NC=1Cl WCYYAQFQZQEUEN-UHFFFAOYSA-N 0.000 description 1
- YRSSHOVRSMQULE-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzonitrile Chemical compound OC1=C(Cl)C=C(C#N)C=C1Cl YRSSHOVRSMQULE-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- YKYGJHGXTSEGDB-UHFFFAOYSA-N 3-(3-chloro-4-ethoxyphenyl)-1,1-dimethylurea Chemical compound CCOC1=CC=C(NC(=O)N(C)C)C=C1Cl YKYGJHGXTSEGDB-UHFFFAOYSA-N 0.000 description 1
- SCFGLMLXZAQXGC-UHFFFAOYSA-N 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one Chemical compound O=C1N(C)CC(O)N1C1=NOC(C(C)(C)C)=C1 SCFGLMLXZAQXGC-UHFFFAOYSA-N 0.000 description 1
- YFEUKKUPOVGUIW-UHFFFAOYSA-N 3-[3-chloro-4-[chloro(difluoro)methyl]sulfanylphenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(SC(F)(F)Cl)C(Cl)=C1 YFEUKKUPOVGUIW-UHFFFAOYSA-N 0.000 description 1
- AMVYOVYGIJXTQB-UHFFFAOYSA-N 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(NC(=O)N(C)C)C=C1 AMVYOVYGIJXTQB-UHFFFAOYSA-N 0.000 description 1
- WYJOEQHHWHAJRB-UHFFFAOYSA-N 3-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]oxolane Chemical compound C1=C(OC2COCC2)C([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl WYJOEQHHWHAJRB-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- NKOJJXLZHFCSHK-UHFFFAOYSA-N 3-imino-8,9-dimethoxy-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile Chemical compound C1CN2C(=N)SC(C#N)=C2C2=C1C=C(OC)C(OC)=C2 NKOJJXLZHFCSHK-UHFFFAOYSA-N 0.000 description 1
- SOPHXJOERHTMIL-UHFFFAOYSA-N 3-methyl-4,6-dinitro-2-propan-2-ylphenol Chemical compound CC(C)C1=C(C)C([N+]([O-])=O)=CC([N+]([O-])=O)=C1O SOPHXJOERHTMIL-UHFFFAOYSA-N 0.000 description 1
- DXBQEHHOGRVYFF-UHFFFAOYSA-N 3-pyridin-4-ylpentane-2,4-dione Chemical group CC(=O)C(C(C)=O)C1=CC=NC=C1 DXBQEHHOGRVYFF-UHFFFAOYSA-N 0.000 description 1
- JNHUFDXYWPRKLK-UHFFFAOYSA-N 4,4,4-trichlorobut-1-en-2-ylbenzene Chemical compound ClC(Cl)(Cl)CC(=C)C1=CC=CC=C1 JNHUFDXYWPRKLK-UHFFFAOYSA-N 0.000 description 1
- KSROTSBULDYPKA-UHFFFAOYSA-N 4,5-dichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound ClC1=CC=C2NC(C(F)(F)F)=NC2=C1Cl KSROTSBULDYPKA-UHFFFAOYSA-N 0.000 description 1
- NEFZKJCNHBXWLP-UHFFFAOYSA-N 4,5-dimethoxy-2-phenylpyridazin-3-one Chemical compound O=C1C(OC)=C(OC)C=NN1C1=CC=CC=C1 NEFZKJCNHBXWLP-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 description 1
- CYQMVKQKBFFDOO-UHFFFAOYSA-N 4-chloro-5-(dimethylamino)-2-[3-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound O=C1C(Cl)=C(N(C)C)C=NN1C1=CC=CC(C(F)(F)F)=C1 CYQMVKQKBFFDOO-UHFFFAOYSA-N 0.000 description 1
- APOAEMIYHVGWEZ-UHFFFAOYSA-N 4-chloroisoindole-1,3-dione Chemical compound ClC1=CC=CC2=C1C(=O)NC2=O APOAEMIYHVGWEZ-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- OPEJGICLTMWFNQ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methoxymethyl]-5-methyl-3-(3-methylthiophen-2-yl)-4h-1,2-oxazole Chemical compound C1=CSC(C=2CC(C)(COCC=3C(=CC=CC=3F)F)ON=2)=C1C OPEJGICLTMWFNQ-UHFFFAOYSA-N 0.000 description 1
- QQOGZMUZAZWLJH-UHFFFAOYSA-N 5-[2-chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-n-ethylsulfonyl-2-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)CC)=CC(OC=2C(=CC(=CC=2F)C(F)(F)F)Cl)=C1 QQOGZMUZAZWLJH-UHFFFAOYSA-N 0.000 description 1
- ODNZLRLWXRXPOH-UHFFFAOYSA-N 5-amino-4-bromo-2-phenylpyridazin-3-one Chemical compound O=C1C(Br)=C(N)C=NN1C1=CC=CC=C1 ODNZLRLWXRXPOH-UHFFFAOYSA-N 0.000 description 1
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 1
- NWUJLIRYNYNDAJ-UHFFFAOYSA-N 6-(difluoromethylsulfanyl)-2-n,4-n-di(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(NC(C)C)=NC(SC(F)F)=N1 NWUJLIRYNYNDAJ-UHFFFAOYSA-N 0.000 description 1
- QHXDTLYEHWXDSO-UHFFFAOYSA-N 6-chloro-2-n,2-n,4-n,4-n-tetraethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(Cl)=NC(N(CC)CC)=N1 QHXDTLYEHWXDSO-UHFFFAOYSA-N 0.000 description 1
- ZUSHSDOEVHPTCU-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-pyridazin-4-one Chemical compound N1C(Cl)=CC(=O)C(C=2C=CC=CC=2)=N1 ZUSHSDOEVHPTCU-UHFFFAOYSA-N 0.000 description 1
- PMYBBBROJPQQQV-UHFFFAOYSA-N 6-chloro-4-n-(3-methoxypropyl)-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound COCCCNC1=NC(Cl)=NC(NC(C)C)=N1 PMYBBBROJPQQQV-UHFFFAOYSA-N 0.000 description 1
- UCOIYRGMDBGBOU-UHFFFAOYSA-N 6-chloro-4-n-propan-2-ylpyrimidine-2,4-diamine Chemical compound CC(C)NC1=CC(Cl)=NC(N)=N1 UCOIYRGMDBGBOU-UHFFFAOYSA-N 0.000 description 1
- QQRJUWIHLNBDQF-UHFFFAOYSA-N 6-chloro-5-methylsulfanylpyrimidine-2,4-diamine Chemical compound CSC1=C(N)N=C(N)N=C1Cl QQRJUWIHLNBDQF-UHFFFAOYSA-N 0.000 description 1
- BBPLSOGERZQYQC-UHFFFAOYSA-N 6-methylheptyl 2-(2,4-dichlorophenoxy)acetate Chemical compound CC(C)CCCCCOC(=O)COC1=CC=C(Cl)C=C1Cl BBPLSOGERZQYQC-UHFFFAOYSA-N 0.000 description 1
- PDIYKJRLQHHRAG-UHFFFAOYSA-N 6-methylheptyl 2-(4-chloro-2-methylphenoxy)acetate Chemical compound CC(C)CCCCCOC(=O)COC1=CC=C(Cl)C=C1C PDIYKJRLQHHRAG-UHFFFAOYSA-N 0.000 description 1
- HVHHQHTXTGUMSR-UHFFFAOYSA-N 6-tert-butyl-3-(dimethylamino)-4-methyl-1,2,4-triazin-5-one Chemical compound CN(C)C1=NN=C(C(C)(C)C)C(=O)N1C HVHHQHTXTGUMSR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 241000448435 Acalypha australis Species 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- 239000002890 Aclonifen Substances 0.000 description 1
- 241001522110 Aegilops tauschii Species 0.000 description 1
- 241000209136 Agropyron Species 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 241000748223 Alisma Species 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219317 Amaranthaceae Species 0.000 description 1
- 239000003666 Amidosulfuron Substances 0.000 description 1
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 108020005544 Antisense RNA Proteins 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000003826 Artemisia Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 240000006891 Artemisia vulgaris Species 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 239000005469 Azimsulfuron Substances 0.000 description 1
- AFIIBUOYKYSPKB-UHFFFAOYSA-N Aziprotryne Chemical compound CSC1=NC(NC(C)C)=NC(N=[N+]=[N-])=N1 AFIIBUOYKYSPKB-UHFFFAOYSA-N 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001490192 Beckmannia syzigachne Species 0.000 description 1
- 239000005470 Beflubutamid Substances 0.000 description 1
- 239000005471 Benfluralin Substances 0.000 description 1
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 description 1
- 239000005472 Bensulfuron methyl Substances 0.000 description 1
- RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 description 1
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 description 1
- DTCJYIIKPVRVDD-UHFFFAOYSA-N Benzthiazuron Chemical compound C1=CC=C2SC(NC(=O)NC)=NC2=C1 DTCJYIIKPVRVDD-UHFFFAOYSA-N 0.000 description 1
- 239000005484 Bifenox Substances 0.000 description 1
- 241000339490 Brachyachne Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XTFNPKDYCLFGPV-OMCISZLKSA-N Bromofenoxim Chemical compound C1=C(Br)C(O)=C(Br)C=C1\C=N\OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XTFNPKDYCLFGPV-OMCISZLKSA-N 0.000 description 1
- 241000544785 Bromus japonicus Species 0.000 description 1
- OEYOMNZEMCPTKN-UHFFFAOYSA-N Butamifos Chemical compound CCC(C)NP(=S)(OCC)OC1=CC(C)=CC=C1[N+]([O-])=O OEYOMNZEMCPTKN-UHFFFAOYSA-N 0.000 description 1
- SWMGXKSQWDSBKV-UHFFFAOYSA-N Buthidazole Chemical compound O=C1N(C)CC(O)N1C1=NN=C(C(C)(C)C)S1 SWMGXKSQWDSBKV-UHFFFAOYSA-N 0.000 description 1
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 description 1
- BYYMILHAKOURNM-UHFFFAOYSA-N Buturon Chemical compound C#CC(C)N(C)C(=O)NC1=CC=C(Cl)C=C1 BYYMILHAKOURNM-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 239000005490 Carbetamide Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108090000994 Catalytic RNA Proteins 0.000 description 1
- 102000053642 Catalytic RNA Human genes 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-UHFFFAOYSA-N 0.000 description 1
- NLYNUTMZTCLNOO-UHFFFAOYSA-N Chlorbromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 NLYNUTMZTCLNOO-UHFFFAOYSA-N 0.000 description 1
- ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 description 1
- YJKIALIXRCSISK-UHFFFAOYSA-N Chlorfenprop-methyl Chemical group COC(=O)C(Cl)CC1=CC=C(Cl)C=C1 YJKIALIXRCSISK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005647 Chlorpropham Substances 0.000 description 1
- 239000005496 Chlorsulfuron Substances 0.000 description 1
- KZCBXHSWMMIEQU-UHFFFAOYSA-N Chlorthal Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(C(O)=O)C(Cl)=C1Cl KZCBXHSWMMIEQU-UHFFFAOYSA-N 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 240000001579 Cirsium arvense Species 0.000 description 1
- 235000005918 Cirsium arvense Nutrition 0.000 description 1
- 241000233839 Commelina communis Species 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- DNPSYFHJYIRREW-UHFFFAOYSA-N Credazine Chemical compound CC1=CC=CC=C1OC1=CC=CN=N1 DNPSYFHJYIRREW-UHFFFAOYSA-N 0.000 description 1
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 239000005502 Cyhalofop-butyl Substances 0.000 description 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- FMGYKKMPNATWHP-UHFFFAOYSA-N Cyperquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=CC=C1 FMGYKKMPNATWHP-UHFFFAOYSA-N 0.000 description 1
- 244000285790 Cyperus iria Species 0.000 description 1
- 235000016854 Cyperus rotundus Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 102100024452 DNA-directed RNA polymerase III subunit RPC1 Human genes 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- BIQOEDQVNIYWPQ-UHFFFAOYSA-N Delachlor Chemical compound CC(C)COCN(C(=O)CCl)C1=C(C)C=CC=C1C BIQOEDQVNIYWPQ-UHFFFAOYSA-N 0.000 description 1
- HCRWJJJUKUVORR-UHFFFAOYSA-N Desmetryn Chemical compound CNC1=NC(NC(C)C)=NC(SC)=N1 HCRWJJJUKUVORR-UHFFFAOYSA-N 0.000 description 1
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 1
- SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 description 1
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 1
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 description 1
- WFKSADNZWSKCRZ-UHFFFAOYSA-N Diethatyl-ethyl Chemical group CCOC(=O)CN(C(=O)CCl)C1=C(CC)C=CC=C1CC WFKSADNZWSKCRZ-UHFFFAOYSA-N 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- DHWRNDJOGMTCPB-UHFFFAOYSA-N Dimefuron Chemical compound ClC1=CC(NC(=O)N(C)C)=CC=C1N1C(=O)OC(C(C)(C)C)=N1 DHWRNDJOGMTCPB-UHFFFAOYSA-N 0.000 description 1
- 239000005508 Dimethachlor Substances 0.000 description 1
- IKYICRRUVNIHPP-UHFFFAOYSA-N Dimethametryn Chemical compound CCNC1=NC(NC(C)C(C)C)=NC(SC)=N1 IKYICRRUVNIHPP-UHFFFAOYSA-N 0.000 description 1
- 239000005509 Dimethenamid-P Substances 0.000 description 1
- FVCPXLWAKNJIKK-UHFFFAOYSA-N Dimexano Chemical group COC(=S)SSC(=S)OC FVCPXLWAKNJIKK-UHFFFAOYSA-N 0.000 description 1
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 description 1
- QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 description 1
- NPWMZOGDXOFZIN-UHFFFAOYSA-N Dipropetryn Chemical compound CCSC1=NC(NC(C)C)=NC(NC(C)C)=N1 NPWMZOGDXOFZIN-UHFFFAOYSA-N 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- IAUFMJOLSFEAIJ-UHFFFAOYSA-N Eglinazine Chemical compound CCNC1=NC(Cl)=NC(NCC(O)=O)=N1 IAUFMJOLSFEAIJ-UHFFFAOYSA-N 0.000 description 1
- 241000202829 Eleocharis Species 0.000 description 1
- KMHZPJNVPCAUMN-UHFFFAOYSA-N Erbon Chemical compound CC(Cl)(Cl)C(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl KMHZPJNVPCAUMN-UHFFFAOYSA-N 0.000 description 1
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 description 1
- PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 description 1
- KCOCSOWTADCKOL-UHFFFAOYSA-N Ethidimuron Chemical compound CCS(=O)(=O)C1=NN=C(N(C)C(=O)NC)S1 KCOCSOWTADCKOL-UHFFFAOYSA-N 0.000 description 1
- WARIWGPBHKPYON-UHFFFAOYSA-N Ethiolate Chemical compound CCSC(=O)N(CC)CC WARIWGPBHKPYON-UHFFFAOYSA-N 0.000 description 1
- 239000005512 Ethofumesate Substances 0.000 description 1
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 description 1
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 description 1
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical group N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 description 1
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 description 1
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 description 1
- 241000234643 Festuca arundinacea Species 0.000 description 1
- 241001290564 Fimbristylis Species 0.000 description 1
- 239000005514 Flazasulfuron Substances 0.000 description 1
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 description 1
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 description 1
- 239000005529 Florasulam Substances 0.000 description 1
- FICWGWVVIRLNRB-UHFFFAOYSA-N Flucetosulfuron Chemical compound COCC(=O)OC(C(C)F)C1=NC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 FICWGWVVIRLNRB-UHFFFAOYSA-N 0.000 description 1
- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 description 1
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 1
- IRECWLYBCAZIJM-UHFFFAOYSA-N Flumiclorac pentyl Chemical group C1=C(Cl)C(OCC(=O)OCCCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F IRECWLYBCAZIJM-UHFFFAOYSA-N 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- HHMCAJWVGYGUEF-UHFFFAOYSA-N Fluorodifen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O HHMCAJWVGYGUEF-UHFFFAOYSA-N 0.000 description 1
- DHAHEVIQIYRFRG-UHFFFAOYSA-N Fluoroglycofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 DHAHEVIQIYRFRG-UHFFFAOYSA-N 0.000 description 1
- AOQMRUTZEYVDIL-UHFFFAOYSA-N Flupoxam Chemical compound C=1C=C(Cl)C(COCC(F)(F)C(F)(F)F)=CC=1N1N=C(C(=O)N)N=C1C1=CC=CC=C1 AOQMRUTZEYVDIL-UHFFFAOYSA-N 0.000 description 1
- PXRROZVNOOEPPZ-UHFFFAOYSA-N Flupropanate Chemical compound OC(=O)C(F)(F)C(F)F PXRROZVNOOEPPZ-UHFFFAOYSA-N 0.000 description 1
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 description 1
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 description 1
- UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 description 1
- 239000005560 Foramsulfuron Substances 0.000 description 1
- 241001669573 Galeorhinus galeus Species 0.000 description 1
- 239000005980 Gibberellic acid Substances 0.000 description 1
- 239000005565 Haloxyfop-P Substances 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 description 1
- 101000689002 Homo sapiens DNA-directed RNA polymerase III subunit RPC1 Proteins 0.000 description 1
- 206010053317 Hydrophobia Diseases 0.000 description 1
- 239000005981 Imazaquin Substances 0.000 description 1
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 1
- 239000005567 Imazosulfuron Substances 0.000 description 1
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 description 1
- 240000007171 Imperata cylindrica Species 0.000 description 1
- PMAAYIYCDXGUAP-UHFFFAOYSA-N Indanofan Chemical compound O=C1C2=CC=CC=C2C(=O)C1(CC)CC1(C=2C=C(Cl)C=CC=2)CO1 PMAAYIYCDXGUAP-UHFFFAOYSA-N 0.000 description 1
- JUJFQMPKBJPSFZ-UHFFFAOYSA-M Iodosulfuron-methyl-sodium Chemical compound [Na+].COC(=O)C1=CC=C(I)C=C1S(=O)(=O)[N-]C(=O)NC1=NC(C)=NC(OC)=N1 JUJFQMPKBJPSFZ-UHFFFAOYSA-M 0.000 description 1
- QBEXFUOWUYCXNI-UHFFFAOYSA-N Ioxynil octanoate Chemical compound CCCCCCCC(=O)OC1=C(I)C=C(C#N)C=C1I QBEXFUOWUYCXNI-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 240000007218 Ipomoea hederacea Species 0.000 description 1
- PSYBGEADHLUXCS-UHFFFAOYSA-N Isocil Chemical compound CC(C)N1C(=O)NC(C)=C(Br)C1=O PSYBGEADHLUXCS-UHFFFAOYSA-N 0.000 description 1
- NEKOXWSIMFDGMA-UHFFFAOYSA-N Isopropalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(C)C)C=C1[N+]([O-])=O NEKOXWSIMFDGMA-UHFFFAOYSA-N 0.000 description 1
- JLLJHQLUZAKJFH-UHFFFAOYSA-N Isouron Chemical compound CN(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 JLLJHQLUZAKJFH-UHFFFAOYSA-N 0.000 description 1
- 239000005570 Isoxaben Substances 0.000 description 1
- ANFHKXSOSRDDRQ-UHFFFAOYSA-N Isoxapyrifop Chemical compound C1CCON1C(=O)C(C)OC(C=C1)=CC=C1OC1=NC=C(Cl)C=C1Cl ANFHKXSOSRDDRQ-UHFFFAOYSA-N 0.000 description 1
- UQVYUTAMNICZNI-UHFFFAOYSA-N Karbutilate Chemical compound CN(C)C(=O)NC1=CC=CC(NC(=O)OC(C)(C)C)=C1 UQVYUTAMNICZNI-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 235000009193 Lamium purpureum Nutrition 0.000 description 1
- 240000006503 Lamium purpureum Species 0.000 description 1
- 239000005572 Lenacil Substances 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 1
- AZFKQCNGMSSWDS-UHFFFAOYSA-N MCPA-thioethyl Chemical group CCSC(=O)COC1=CC=C(Cl)C=C1C AZFKQCNGMSSWDS-UHFFFAOYSA-N 0.000 description 1
- ZHKWNOGSHWXSDY-UHFFFAOYSA-N MK-129 Chemical compound C1=CC(Cl)=CC=C1COC1=CC=C(N2C(C3=C(CCCC3)C2=O)=O)C=C1 ZHKWNOGSHWXSDY-UHFFFAOYSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- GZJNBGYLANALSV-UHFFFAOYSA-N Medinoterb acetate Chemical compound CC(=O)OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C)=C1C(C)(C)C GZJNBGYLANALSV-UHFFFAOYSA-N 0.000 description 1
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 1
- 239000005577 Mesosulfuron Substances 0.000 description 1
- 239000005578 Mesotrione Substances 0.000 description 1
- 239000005579 Metamitron Substances 0.000 description 1
- 239000005580 Metazachlor Substances 0.000 description 1
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 1
- LRUUNMYPIBZBQH-UHFFFAOYSA-N Methazole Chemical compound O=C1N(C)C(=O)ON1C1=CC=C(Cl)C(Cl)=C1 LRUUNMYPIBZBQH-UHFFFAOYSA-N 0.000 description 1
- MMCJEAKINANSOL-UHFFFAOYSA-N Methiuron Chemical compound CN(C)C(=S)NC1=CC=CC(C)=C1 MMCJEAKINANSOL-UHFFFAOYSA-N 0.000 description 1
- DDUIUBPJPOKOMV-UHFFFAOYSA-N Methoprotryne Chemical compound COCCCNC1=NC(NC(C)C)=NC(SC)=N1 DDUIUBPJPOKOMV-UHFFFAOYSA-N 0.000 description 1
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 description 1
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 description 1
- 239000005581 Metobromuron Substances 0.000 description 1
- WLFDQEVORAMCIM-UHFFFAOYSA-N Metobromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C=C1 WLFDQEVORAMCIM-UHFFFAOYSA-N 0.000 description 1
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 1
- 239000005582 Metosulam Substances 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- KXGYBSNVFXBPNO-UHFFFAOYSA-N Monalide Chemical compound CCCC(C)(C)C(=O)NC1=CC=C(Cl)C=C1 KXGYBSNVFXBPNO-UHFFFAOYSA-N 0.000 description 1
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- BZRUVKZGXNSXMB-UHFFFAOYSA-N N-(butan-2-yl)-6-chloro-N'-ethyl-1,3,5-triazine-2,4-diamine Chemical compound CCNC1=NC(Cl)=NC(NC(C)CC)=N1 BZRUVKZGXNSXMB-UHFFFAOYSA-N 0.000 description 1
- ZJMZZNVGNSWOOM-UHFFFAOYSA-N N-(butan-2-yl)-N'-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine Chemical compound CCNC1=NC(NC(C)CC)=NC(OC)=N1 ZJMZZNVGNSWOOM-UHFFFAOYSA-N 0.000 description 1
- FFQPZWRNXKPNPX-UHFFFAOYSA-N N-benzyl-2-[4-fluoro-3-(trifluoromethyl)phenoxy]butanamide Chemical compound C=1C=CC=CC=1CNC(=O)C(CC)OC1=CC=C(F)C(C(F)(F)F)=C1 FFQPZWRNXKPNPX-UHFFFAOYSA-N 0.000 description 1
- NTBVTCXMRYKRTB-UHFFFAOYSA-N N-{2-[(4,6-dimethoxypyrimidin-2-yl)(hydroxy)methyl]-6-(methoxymethyl)phenyl}-1,1-difluoromethanesulfonamide Chemical compound COCC1=CC=CC(C(O)C=2N=C(OC)C=C(OC)N=2)=C1NS(=O)(=O)C(F)F NTBVTCXMRYKRTB-UHFFFAOYSA-N 0.000 description 1
- 229910017909 NH2NH2H2O Inorganic materials 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 1
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 240000008467 Oryza sativa Japonica Group Species 0.000 description 1
- 239000005587 Oryzalin Substances 0.000 description 1
- WFVUIONFJOAYPK-KAMYIIQDSA-N Oxabetrinil Chemical compound C=1C=CC=CC=1C(/C#N)=N\OCC1OCCO1 WFVUIONFJOAYPK-KAMYIIQDSA-N 0.000 description 1
- XRGQIRXQFSJBKJ-UHFFFAOYSA-N Oxapyrazon Chemical compound O=C1C(Br)=C(NC(=O)C(=O)O)C=NN1C1=CC=CC=C1 XRGQIRXQFSJBKJ-UHFFFAOYSA-N 0.000 description 1
- 239000005589 Oxasulfuron Substances 0.000 description 1
- FCOHEOSCARXMMS-UHFFFAOYSA-N Oxaziclomefone Chemical compound C1OC(C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C1=CC(Cl)=CC(Cl)=C1 FCOHEOSCARXMMS-UHFFFAOYSA-N 0.000 description 1
- CDHBAZHPEVDWMO-UHFFFAOYSA-N Parafluron Chemical compound CN(C)C(=O)NC1=CC=C(C(F)(F)F)C=C1 CDHBAZHPEVDWMO-UHFFFAOYSA-N 0.000 description 1
- 241000044541 Paspalum vaginatum Species 0.000 description 1
- SGEJQUSYQTVSIU-UHFFFAOYSA-N Pebulate Chemical compound CCCCN(CC)C(=O)SCCC SGEJQUSYQTVSIU-UHFFFAOYSA-N 0.000 description 1
- 244000038248 Pennisetum spicatum Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- 239000005592 Penoxsulam Substances 0.000 description 1
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 description 1
- WGVWLKXZBUVUAM-UHFFFAOYSA-N Pentanochlor Chemical compound CCCC(C)C(=O)NC1=CC=C(C)C(Cl)=C1 WGVWLKXZBUVUAM-UHFFFAOYSA-N 0.000 description 1
- 239000005593 Pethoxamid Substances 0.000 description 1
- 241000745991 Phalaris Species 0.000 description 1
- 244000081757 Phalaris arundinacea Species 0.000 description 1
- PWEOEHNGYFXZLI-UHFFFAOYSA-N Phenisopham Chemical compound C=1C=CC=CC=1N(CC)C(=O)OC1=CC=CC(NC(=O)OC(C)C)=C1 PWEOEHNGYFXZLI-UHFFFAOYSA-N 0.000 description 1
- QQXXYTVEGCOZRF-UHFFFAOYSA-N Phenobenzuron Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C(=O)N(C)C)C(=O)C1=CC=CC=C1 QQXXYTVEGCOZRF-UHFFFAOYSA-N 0.000 description 1
- 241001137460 Phleum paniculatum Species 0.000 description 1
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 description 1
- ITVQAKZNYJEWKS-UHFFFAOYSA-N Profluralin Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CCC)CC1CC1 ITVQAKZNYJEWKS-UHFFFAOYSA-N 0.000 description 1
- XCXCBWSRDOSZRU-UHFFFAOYSA-N Proglinazine Chemical compound CC(C)NC1=NC(Cl)=NC(NCC(O)=O)=N1 XCXCBWSRDOSZRU-UHFFFAOYSA-N 0.000 description 1
- 239000005600 Propaquizafop Substances 0.000 description 1
- 239000005601 Propoxycarbazone Substances 0.000 description 1
- 239000005604 Prosulfuron Substances 0.000 description 1
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 1
- 239000005605 Pyraflufen-ethyl Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000005606 Pyridate Substances 0.000 description 1
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 1
- RRKHIAYNPVQKEF-UHFFFAOYSA-N Pyriftalid Chemical compound COC1=CC(OC)=NC(SC=2C=3C(=O)OC(C)C=3C=CC=2)=N1 RRKHIAYNPVQKEF-UHFFFAOYSA-N 0.000 description 1
- CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 description 1
- 239000005607 Pyroxsulam Substances 0.000 description 1
- 239000005608 Quinmerac Substances 0.000 description 1
- 239000005614 Quizalofop-P-ethyl Substances 0.000 description 1
- 235000003846 Ricinus Nutrition 0.000 description 1
- 241000322381 Ricinus <louse> Species 0.000 description 1
- 235000008484 Rorippa indica Nutrition 0.000 description 1
- 240000004053 Rorippa indica Species 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- WOZQBERUBLYCEG-UHFFFAOYSA-N SWEP Chemical compound COC(=O)NC1=CC=C(Cl)C(Cl)=C1 WOZQBERUBLYCEG-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000009132 Sagittaria sagittifolia Species 0.000 description 1
- 241000202758 Scirpus Species 0.000 description 1
- 241001550931 Sclerochloa dura Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- JXVIIQLNUPXOII-UHFFFAOYSA-N Siduron Chemical compound CC1CCCCC1NC(=O)NC1=CC=CC=C1 JXVIIQLNUPXOII-UHFFFAOYSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 235000006731 Sonchus arvensis Nutrition 0.000 description 1
- 244000111146 Sonchus arvensis Species 0.000 description 1
- 239000005618 Sulcotrione Substances 0.000 description 1
- XJCLWVXTCRQIDI-UHFFFAOYSA-N Sulfallate Chemical compound CCN(CC)C(=S)SCC(Cl)=C XJCLWVXTCRQIDI-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 239000005619 Sulfosulfuron Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical compound C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 description 1
- NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- KDWQYMVPYJGPHS-UHFFFAOYSA-N Thenylchlor Chemical compound C1=CSC(CN(C(=O)CCl)C=2C(=CC=CC=2C)C)=C1OC KDWQYMVPYJGPHS-UHFFFAOYSA-N 0.000 description 1
- BBJPZPLAZVZTGR-UHFFFAOYSA-N Thiazafluron Chemical compound CNC(=O)N(C)C1=NN=C(C(F)(F)F)S1 BBJPZPLAZVZTGR-UHFFFAOYSA-N 0.000 description 1
- YIJZJEYQBAAWRJ-UHFFFAOYSA-N Thiazopyr Chemical compound N1=C(C(F)F)C(C(=O)OC)=C(CC(C)C)C(C=2SCCN=2)=C1C(F)(F)F YIJZJEYQBAAWRJ-UHFFFAOYSA-N 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- PHSUVQBHRAWOQD-UHFFFAOYSA-N Tiocarbazil Chemical compound CCC(C)N(C(C)CC)C(=O)SCC1=CC=CC=C1 PHSUVQBHRAWOQD-UHFFFAOYSA-N 0.000 description 1
- 239000005624 Tralkoxydim Substances 0.000 description 1
- 239000005625 Tri-allate Substances 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 description 1
- HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 description 1
- 239000005629 Tritosulfuron Substances 0.000 description 1
- 235000000502 Veronica didyma Nutrition 0.000 description 1
- 241001166549 Veronica hederifolia Species 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 241000990144 Veronica persica Species 0.000 description 1
- 241001470675 Veronica polita Species 0.000 description 1
- 244000047670 Viola x wittrockiana Species 0.000 description 1
- 235000004031 Viola x wittrockiana Nutrition 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241001251949 Xanthium sibiricum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 241000981595 Zoysia japonica Species 0.000 description 1
- AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 description 1
- LUZZPGJQJKMMDM-JTQLQIEISA-N [(2s)-1-ethoxy-1-oxopropan-2-yl] 2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoate Chemical group C1=C(Cl)C(C(=O)O[C@@H](C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 LUZZPGJQJKMMDM-JTQLQIEISA-N 0.000 description 1
- OTSYOPHQYHLKTK-UHFFFAOYSA-N [2-(azepan-1-yl)-2-oxoethyl] n-methylsulfamate Chemical compound CNS(=O)(=O)OCC(=O)N1CCCCCC1 OTSYOPHQYHLKTK-UHFFFAOYSA-N 0.000 description 1
- MVEFZZKZBYQFPP-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] n-(3-methylphenyl)carbamate Chemical group CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 MVEFZZKZBYQFPP-UHFFFAOYSA-N 0.000 description 1
- CYDCAYZRTPOUJJ-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-(1-chlorobutan-2-yl)carbamate Chemical compound CCC(CCl)NC(=O)OC1=CC=CC(NC(=O)OC)=C1 CYDCAYZRTPOUJJ-UHFFFAOYSA-N 0.000 description 1
- NWBFHIJKEYFVND-UHFFFAOYSA-N [4-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)benzoyl]-2-ethylpyrazol-3-yl] 1,3-dimethylpyrazole-4-carboxylate Chemical compound N1(C=C(C(=O)OC=2N(CC)N=CC=2C(=O)C2=C(C(=C(S(=O)(=O)C)C=C2)COCC(F)(F)F)Cl)C(C)=N1)C NWBFHIJKEYFVND-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- KWAIHLIXESXTJL-UHFFFAOYSA-N aminocyclopyrachlor Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 KWAIHLIXESXTJL-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 235000009052 artemisia Nutrition 0.000 description 1
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PXWUKZGIHQRDHL-UHFFFAOYSA-N atraton Chemical compound CCNC1=NC(NC(C)C)=NC(OC)=N1 PXWUKZGIHQRDHL-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- XOEMATDHVZOBSG-UHFFFAOYSA-N azafenidin Chemical compound C1=C(OCC#C)C(Cl)=CC(Cl)=C1N1C(=O)N2CCCCC2=N1 XOEMATDHVZOBSG-UHFFFAOYSA-N 0.000 description 1
- GNZZHGJSMCDMBU-UHFFFAOYSA-N azane;5-(methoxymethyl)-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound [NH4+].[O-]C(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 GNZZHGJSMCDMBU-UHFFFAOYSA-N 0.000 description 1
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- LVKBXDHACCFCTA-UHFFFAOYSA-N bencarbazone Chemical compound C1=C(C(N)=S)C(NS(=O)(=O)CC)=CC(N2C(N(C)C(=N2)C(F)(F)F)=O)=C1F LVKBXDHACCFCTA-UHFFFAOYSA-N 0.000 description 1
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- HTTLBYITFHMYFK-UHFFFAOYSA-N bentranil Chemical compound N=1C2=CC=CC=C2C(=O)OC=1C1=CC=CC=C1 HTTLBYITFHMYFK-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 description 1
- JEDYYFXHPAIBGR-UHFFFAOYSA-N butafenacil Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(Cl)C(C(=O)OC(C)(C)C(=O)OCC=C)=C1 JEDYYFXHPAIBGR-UHFFFAOYSA-N 0.000 description 1
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
- UQMRAFJOBWOFNS-UHFFFAOYSA-N butyl 2-(2,4-dichlorophenoxy)acetate Chemical compound CCCCOC(=O)COC1=CC=C(Cl)C=C1Cl UQMRAFJOBWOFNS-UHFFFAOYSA-N 0.000 description 1
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- PNCNFDRSHBFIDM-WOJGMQOQSA-N chembl111617 Chemical compound C=CCO\N=C(/CCC)C1=C(O)C(C(=O)OC)C(C)(C)CC1=O PNCNFDRSHBFIDM-WOJGMQOQSA-N 0.000 description 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 description 1
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 1
- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000003184 complementary RNA Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 description 1
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 1
- JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical group CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 1
- HVCNNTAUBZIYCG-UHFFFAOYSA-N ethyl 2-[4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2S1 HVCNNTAUBZIYCG-UHFFFAOYSA-N 0.000 description 1
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- ACDZDIIWZVQMIX-UHFFFAOYSA-N fenoxasulfone Chemical compound C1=C(Cl)C(OCC)=CC(Cl)=C1CS(=O)(=O)C1=NOC(C)(C)C1 ACDZDIIWZVQMIX-UHFFFAOYSA-N 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- XFZUQTKDBCOXPP-UHFFFAOYSA-N florpyrauxifen Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C(Cl)=C(C(O)=O)N=2)F)=C1F XFZUQTKDBCOXPP-UHFFFAOYSA-N 0.000 description 1
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 description 1
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 description 1
- DNUAYCRATWAJQE-UHFFFAOYSA-N flufenpyr-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(N2C(C(C)=C(C=N2)C(F)(F)F)=O)=C1F DNUAYCRATWAJQE-UHFFFAOYSA-N 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 description 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000010362 genome editing Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- MJAWMRVEIWPJRW-UHFFFAOYSA-N haloxydine Chemical compound FC=1NC(F)=C(Cl)C(=O)C=1Cl MJAWMRVEIWPJRW-UHFFFAOYSA-N 0.000 description 1
- GOCUAJYOYBLQRH-MRVPVSSYSA-N haloxyfop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-MRVPVSSYSA-N 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- RBJAKRVCYLJDPZ-UHFFFAOYSA-N hexyl 2-[5-(4-bromophenoxy)-2-nitrophenoxy]propanoate Chemical compound C1=C([N+]([O-])=O)C(OC(C)C(=O)OCCCCCC)=CC(OC=2C=CC(Br)=CC=2)=C1 RBJAKRVCYLJDPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- RBNIGDFIUWJJEV-LLVKDONJSA-N methyl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-LLVKDONJSA-N 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical group COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 description 1
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 1
- VGBNSONMEGTIDX-UHFFFAOYSA-N methyl 2-[(4-methylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC=CC(C)=N1 VGBNSONMEGTIDX-UHFFFAOYSA-N 0.000 description 1
- GAIFAPDHLCPUMF-IWIPYMOSSA-N methyl 2-[(e)-[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxyacetate Chemical compound C1=C([N+]([O-])=O)C(C(=N\OCC(=O)OC)/COC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 GAIFAPDHLCPUMF-IWIPYMOSSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 description 1
- NMNIAXSDJGZKKT-UHFFFAOYSA-N methyl 3-hydroxy-4-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]pentanoate Chemical group C1=CC(OC(C)C(O)CC(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 NMNIAXSDJGZKKT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- MYURAHUSYDVWQA-UHFFFAOYSA-N methyl n'-(4-chlorophenyl)-n,n-dimethylcarbamimidate Chemical compound COC(N(C)C)=NC1=CC=C(Cl)C=C1 MYURAHUSYDVWQA-UHFFFAOYSA-N 0.000 description 1
- ZGUYPJJFHYFLBV-UHFFFAOYSA-N methyl n-(5-tert-butyl-1,2-oxazol-3-yl)carbamate Chemical compound COC(=O)NC=1C=C(C(C)(C)C)ON=1 ZGUYPJJFHYFLBV-UHFFFAOYSA-N 0.000 description 1
- ZTFLDKYLDUZSMN-UHFFFAOYSA-N methyl n-[4-(methoxycarbonylamino)phenyl]sulfonylcarbamate Chemical compound COC(=O)NC1=CC=C(S(=O)(=O)NC(=O)OC)C=C1 ZTFLDKYLDUZSMN-UHFFFAOYSA-N 0.000 description 1
- LFDDUUFFHPNIPZ-UHFFFAOYSA-N methyl n-[4-[[2-(4-chloro-2-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound C1=CC(S(=O)(=O)NC(=O)OC)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C LFDDUUFFHPNIPZ-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 1
- 229960002939 metizoline Drugs 0.000 description 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- YGLMVCVJLXREAK-NGDQXYMTSA-N n,n-dimethyl-n'-(octahydro-4,7-methano-1h-inden-5-yl)-(3aα,4α,5α,7α,7aα)-urea Chemical compound C([C@@H]12)CC[C@H]1[C@@H]1C[C@H](NC(=O)N(C)C)[C@@H]2C1 YGLMVCVJLXREAK-NGDQXYMTSA-N 0.000 description 1
- DRWWMFAZIDKURY-UHFFFAOYSA-N n-(2-methylprop-2-enyl)-2,6-dinitro-n-propyl-4-(trifluoromethyl)aniline Chemical compound CCCN(CC(C)=C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O DRWWMFAZIDKURY-UHFFFAOYSA-N 0.000 description 1
- RGKLVVDHWRAWRO-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-n-(dimethylcarbamoyl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N(C(=O)N(C)C)C1=CC=C(Cl)C(Cl)=C1 RGKLVVDHWRAWRO-UHFFFAOYSA-N 0.000 description 1
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 1
- GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 description 1
- KGMBZDZHRAFLBY-UHFFFAOYSA-N n-(butoxymethyl)-n-(2-tert-butyl-6-methylphenyl)-2-chloroacetamide Chemical compound CCCCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(C)(C)C KGMBZDZHRAFLBY-UHFFFAOYSA-N 0.000 description 1
- LKVOXDJKFRBRQV-UHFFFAOYSA-N n-(dimethyl-$l^{4}-sulfanylidene)-4-(dipropylamino)-3,5-dinitrobenzenesulfonamide Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(=O)(=O)N=S(C)C)C=C1[N+]([O-])=O LKVOXDJKFRBRQV-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- PJFGPJQBWSEWKX-UHFFFAOYSA-N n-[(2,4-dichlorophenoxy)-methoxyphosphinothioyl]propan-2-amine Chemical compound CC(C)NP(=S)(OC)OC1=CC=C(Cl)C=C1Cl PJFGPJQBWSEWKX-UHFFFAOYSA-N 0.000 description 1
- QBHMPGXYSYRJEW-UHFFFAOYSA-N n-[(2,4-dimethyl-6-nitrophenoxy)-ethoxyphosphinothioyl]propan-2-amine Chemical compound CCOP(=S)(NC(C)C)OC1=C(C)C=C(C)C=C1[N+]([O-])=O QBHMPGXYSYRJEW-UHFFFAOYSA-N 0.000 description 1
- KDOKZLSGPVBDLS-UHFFFAOYSA-N n-[5-(1-chloro-2-methylpropan-2-yl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide Chemical compound S1C(C(C)(CCl)C)=NN=C1NC(=O)C1CC1 KDOKZLSGPVBDLS-UHFFFAOYSA-N 0.000 description 1
- VHEWQRWLIDWRMR-UHFFFAOYSA-N n-[methoxy-(4-methyl-2-nitrophenoxy)phosphinothioyl]propan-2-amine Chemical group CC(C)NP(=S)(OC)OC1=CC=C(C)C=C1[N+]([O-])=O VHEWQRWLIDWRMR-UHFFFAOYSA-N 0.000 description 1
- FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 description 1
- DGPBHERUGBOSFZ-UHFFFAOYSA-N n-but-3-yn-2-yl-2-chloro-n-phenylacetamide Chemical compound C#CC(C)N(C(=O)CCl)C1=CC=CC=C1 DGPBHERUGBOSFZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KCNUWLJAWRWKMO-UHFFFAOYSA-N n-ethyl-n-propyl-3-propylsulfonyl-1,2,4-triazole-1-carboxamide Chemical compound CCCN(CC)C(=O)N1C=NC(S(=O)(=O)CCC)=N1 KCNUWLJAWRWKMO-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- CSWIKHNSBZVWNQ-UHFFFAOYSA-N pethoxamide Chemical compound CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1 CSWIKHNSBZVWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000032361 posttranscriptional gene silencing Effects 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- ZHYPDEKPSXOZKN-UHFFFAOYSA-N propyl 4-[[2-(4,6-dimethoxypyrimidin-2-yl)oxyphenyl]methylamino]benzoate Chemical group C1=CC(C(=O)OCCC)=CC=C1NCC1=CC=CC=C1OC1=NC(OC)=CC(OC)=N1 ZHYPDEKPSXOZKN-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- BUHNESFUCHPWED-UHFFFAOYSA-N s-[(4-methoxyphenyl)methyl] n,n-diethylcarbamothioate Chemical compound CCN(CC)C(=O)SCC1=CC=C(OC)C=C1 BUHNESFUCHPWED-UHFFFAOYSA-N 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229940010115 simetone Drugs 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- QZSGYPOMAGZIOZ-UHFFFAOYSA-M sodium;(2,2-dimethyl-1h-quinolin-4-yl)methanesulfonate Chemical compound [Na+].C1=CC=C2C(CS([O-])(=O)=O)=CC(C)(C)NC2=C1 QZSGYPOMAGZIOZ-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 238000004235 valence bond calculation Methods 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
- 239000002699 waste material Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
The present invention belongs to the technical field of pesticides, and in particular relates to a carboxylic acid derivative-substituted imino aryl compound, a preparation method therefor, a herbicidal composition and use thereof. The compound is as shown in general formula I: Q represents; Y represents halogen, haloalkyl or cyano; Z represents halogen; M represents CH or N; W represents OX5, SX5 or N(X5)2; X represents -CX1X2-(alkyl)n-, -alkyl-CX1X2-(alkyl)n-, or -(CH2)r-; X3 and X4 independently represent O, S, NH, Nalkyl, or the like. The compound has excellent herbicidal activity against gramineous weeds, broadleaf weeds, Cyperaceae weeds, and the like even at low application rates, and has high selectivity to crops.
Description
The invention relates to the field of pesticide technology, and in particular a type of carboxylic acid derivative-substituted iminoaryl compound, préparation method, herbicidal composition and use thereof.
Technical background
Weed control is one of the most important links in the course of achieving high-efficiency agriculture. Varions herbicides are available in the market, for example, patents WO00/50409 etc. disclose the use of a compound of general formula l-aryl-4-thiotriazine as a herbicide, WO95/06641 discloses a compound of substituted l-amino-3-phenyluracils with herbicidal activity, WO95/25725 discloses a compound of pyrimidinyl aryl ketone oximes with herbicidal and insecticidal activities. However, the herbicidal properties of these known compounds against harmful plants and their selectivities to crops are not completely satisfactory. And scientists still need to do continuously research and develop new herbicides with high efficacy, safety, économies and different modes of action due to problems such as the growing market, weed résistance, the service life and économies of pesticides as well as people’s increasing concem on environment.
Invention contents
The invention relates to the field of pesticide technology, and in particular a type of carboxylic acid derivative-substituted iminoaryl compound, préparation method, herbicidal composition and use thereof. The compound has excellent herbicidal activity against gramineous weeds, broadleaf weeds, cyperaceae weeds and so on even at low application rates, and has high selectivity for crops.
The technical solution adopted by the invention is as follows:
A carboxylic acid derivative-substituted iminoaryl compound, represented by general formula Γ:
Q Μ A3 η
Ο □1
Wherein, the dérivative refers to a dérivative suitable for agricultural chemistry, which is used to describe the change of the carboxylic acid fimctional group of the présent invention, and it refers to any ester, acylhydrazide, imidate, thioimidate, amidine, amide, orthoester, acyl cyanide, acyl halide, thioester, thionoester, dithiolester, nitrile or any other carboxylic acid dérivative well known in the art.
To be spécifie, the carboxylic acid derivative-substituted iminoaryl compound, represented by general formula I:
Zv/V/Y <AA^'xsxYw
X4 □
In the above general formulas l'and I,
Q2 04 „, Û4 RinAn'X q^n^q3 R7 n^Q5 R7r?7 q5
Q represents R2 , R6 or R6 ;
Y represents halogen, haloalkyl or cyano;
Z represents halogen;
M represents CH or N;
W represents OX5, SX5 or N(Xs)2;
X represents -CXiX2-(alkyl)n-, -alkyl-CXiX2-(alkyl)n- or -(CH2)r-;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkyl carbonyl, alkoxy carbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclic alkyl, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “cycloalkyl”, “cycloalkylalkyl”, “aryl”, “heterocyclyl”, “arylalkyl” and “heterocyclic alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SC>2)Ri3, -N(Ri3)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring; and Xb X2 are not hydrogen at the same time;
X3, X4 each independently represent O, S, NH or N-alkyl;
X5 represents H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, γθ yS ^A |'θ'χ12 |^crXl2 '/οΑχ ^A ,Xn 13 X 13 1 *11 i *11, T- *11, 5 O , 4 O > υ *11, υ » X14 » X14 »
Ο Χ13χΝ-Χΐ4 y|'N'Xi3 χΝγΧΐ3 àVx
Xi4 , X14 or o , wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano,
O O o s A y, A nitro, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, * X11, 1 Xl1, xn A 0 X11, o
A x \0Y°'Xn V” ΐΝΤΧ” AJI ';rX’3 AAyX” \ Ο” 11, ο , X14 , X14 , X14 and X14 , the “cycloalkyl”, “cycloalkenyl”, “heterocyclyl” and “aryl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
.^n^x13 or N(X5)2 represents X14 or unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;
Qi, Q2, Q3, Q4, Qs each independently represent O or S;
Ri, R2 each independently represent H, cyano, alkyl, alkenyl, alkynyl, formyl alkyl, cyanoalkyl, amino, aminoalkyl, amino carbonyl, amino carbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl,
R4R5N-(CO)-NR3-, R5 , R3-S(O)m-(alkyl)n-, R3-O-(alkyl)n-, R3-(CO)-(alkyl)n-,
R3-O-(alkyl)n-(CO)-, R3-(CO)-O-(alkyl)n-, R3-S-(CO)-(alkyl)n-, R3-O-(CO)-alkyl- or
R3-O-(CO)-O-alkyl-, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “amino”, “aminoalkyl”, “amino carbonyl”, “amino carbonylalkyl” and “aminosulfonyl” are each independently unsubstituted or substituted by one or two groups selected from -Ru, -ORii, -(CO)Rn, -(CO)ORn, -alkyl-(CO)ORn, -(SO2)Rn, -(SO2)ORn, -alkyl-(SO2)Rn, -(CO)N(R12)2 and -(SO2)N(R12)2, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Rb, -N(Rb)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
R6 représente alkyl, alkenyl, alkynyl or cyano, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, alkoxy and alkoxy carbonyl;
R?, R7’, Rs, Rs’ each independently represent H, alkyl, halogen, haloalkyl, amino, hydroxyalkyl or alkoxy;
X11 independently represents H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl or Q M ' Ν χ3Χ^, wherein, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Rb)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Xi2 independently represents alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Rb)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X13, X14 each independently represent H, halogen, cyano, alkoxy, alkoxyalkyl, alkyl carbonyl, alkoxy carbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, aryl, arylalkyl, heterocyclyl or heterocyclic alkyl, or C, X13, X14, taken together, form unsubstituted or substituted cyclic structure, or N, X13, X14, taken together, form unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “aryl”, “arylalkyl”, “heterocyclyl” and “heterocyclic alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2Oform a fused ring;
R3, R4, R5 each independently represent H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Rb, -N (R 13)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2or -OCH2O- form a fused ring;
Ru independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, benzyl, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “phenyl” and “benzyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;
Ri2 independently represents H, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or N(Ri2)2 in -(CO)N(Rj2)2 or -(SO2)N(Ri2)2 each independently represents unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;
Rb independently represents H, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;
r represents an integer of 2 or more; m represents 0, 1 or 2; n independently represents 0 or 1.
Preferably, Y represents halogen, halo C1-C8 alkyl or cyano;
X represents -CXiX2-(C1-C8 alkyl)n-, -(C1-C8 alkyl)-CXiX2-(Cl-C8 alkyl)n- or -(CH2)r;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halo C1-C8 alkoxy, halo C1-C8 alkylthio, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkoxy C1-C8 alkyl, halo C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, aryl, heterocyclyl, aryl C1-C8 alkyl or heterocyclyl C1-C8 alkyl, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “aryl”, “heterocyclyl”, “aryl C1-C8 alkyl” and “heterocyclyl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)OR]3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fiised ring; and Xb X2 are not hydrogen at the same time;
X3, X4 each independently represent O, S, NH or N-(C1-C8)alkyl;
X5 represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 . ^-θ-ν Χυ J n'O' ÿ'rr^Y cycloalkenyl, heterocyclyl, aryl, * xn, * xn, X11, 5 ° , O , xn, o O Xl3'N'Xl4 £ y /'N'X13 À^N'X13 tjtN'Xl3 \'NYX13 'A/*11
Yo 11, x14 , x-14 , X14 , X14 or o , wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkenyl,
s.O. s. S.
heterocyclyl, aryl, * xn, 1 xn,
9 9 ΥθΧ/θΎ /m'X13 sJL '/ .K tA xXii A Y χιι
XXn, /'O X11, X o o , X14 ,
O .^-Ν<γ-Χι3 χ\Ά^-Χΐ3 /Ό^Ύ Χ13
Xi4 , Xi4 and Xu , the “C3-C8 cycloalkyl”, “C3-C8 cycloalkenyl”, “heterocyclyl” and “aryl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SÛ2)Ri3,
-N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
or N(X5)2 represents
X14 or heterocyclyl
nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;
Ri, R2 each independently represent H, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino, amino C1-C8 alkyl, amino carbonyl, amino carbonyl Ç1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl
C1-C8 alkyl, R4R5N-(CO)-NR3-, Rs , R3-S(O)m-(Cl-C8 alkyl)n-, R3-O-(C1-C8 alkyl)n-,
R3-(CO)-(C1-C8 alkyl)n-, R3-O-(C1-C8 alkyl)n-(CO)-, R3-(CO)-O-(C1-C8 alkyl)n-,
R3-S-(CO)-(C1-C8 alkyl)n-, R3-O-(CO)-(C1-C8 alkyl)- or R3-O-(CO)-O-(C1-C8 alkyl)-, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “amino”, “amino C1-C8 alkyl”, “amino carbonyl”, “amino carbonyl C1-C8 alkyl” and “aminosulfonyl” are each independently unsubstituted or substituted by one or two groups selected from -Rlb -ORn, -(CO)Rn, -(CO)ORn, -(C1-C8 alkyl)-(CO)ORn, -(SO2)Rn, -(SO2)ORn, -(C1-C8 alkyl)-(SO2)Rn, -(CO)N(Ri2)2 and -(SO2)N(Ri2)2, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
R6 represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl or cyano, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkoxy and C1-C8 alkoxy carbonyl;
R7, R7’, Rr, R$’ each independently represent H, C1-C8 alkyl, halogen, halo C1-C8 alkyl, amino, hydroxy C1-C8 alkyl or C1-C8 alkoxy;
X11 independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 z'v^tx'y alkyl, aryl, aryl Cl-C8 alkyl or Q M ^N'X3X^, wherein, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X12 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -ORb, -SRb, -(CO)ORb, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Xi3, Xi4 each independently represent H, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or C, X13, X14, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl, or N, X13, X14, taken together, form heterocyclyl with nitrogen atom at 1-position, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “aryl”, “aryl C1-C8 alkyl”, “heterocyclyl” and “heterocyclyl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Rb)2 and -O-(C1-C8 alkyl)-(CO)ORB, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring, the “5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl” is unsubstituted or substituted by 1-4 groups selected from C1-C8 alkyl, C1-C8 alkoxy carbonyl and benzyl, or together with aryl or heterocyclyl forms a fused ring, the “heterocyclyl with nitrogen atom at l-position”is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;
R.3, R4, R5 each independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SC>2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Ru independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, benzyl, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “phenyl” and “benzyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;
R12 independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or N(Ri2)2 in -(CO)N(Ri2)2 or -(SO2)N(Ri2)2 independently e N > 1 ] In . .
represents heterocyclyl 'X , '—/, kor with nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;
R13 independently represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;
r represents 2, 3,4, 5 or 6.
More preferably, Y represents halogen, halo C1-C6 alkyl or cyano;
X represents -CXiX2-(C1-C6 alkyl)n-, -(C1-C6 alkyl)-CXiX2-(Cl-C6 alkyl)n- or -(CH2)r-;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C6 alkyl, halo C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, aryl, heterocyclyl, aryl C1-C6 alkyl or heterocyclyl C1-C6 alkyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “aryl”, “heterocyclyl”, “aryl C1-C6 alkyl” and “heterocyclyl C1-C6 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring; and Xi, X2 are not hydrogen at the same time;
X3, X4 each independently represent O, S, NH or N-(C1-C6)alkyl;
X5 represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6
o o Xi3-N-Xi4 χ x X-N'X13 a\'Xi3 vh'X13 -\-NYX13 À/*11 \ O' 11 s x14 , x14 5 x14 ? x14 or o , wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, χ^ ‘ίζθ'χθ'·χ11 ?*'N'Xl3 heterocyclyl, aryl, ^11, θ Xn, \ θ 11, Ο , X14 , o
'\'ΝχΧΐ3 V^N'Xl3 /ο'ΝχΧΐ3
Xi4 , X14 and Xu , the “C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl” and “aryl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl,
C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SChjRn, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
-VN^Xl3 -Λμ'-'Χ i I N 7 il in-u or N(X5)2 represents xu or heterocyclyl , '—/, or with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;
Ri, R2 each independently represent H, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino, amino C1-C6 alkyl, amino carbonyl, amino carbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl
C1-C6 alkyl, R4R5N-(CO)-NR3-, «5 , R3-S(O)m-(Cl-C6 alkyl)n-, R3-O-(C1-C6 alkyl)n-,
R3-(CO)-(C1-C6 alkyl)n-, R3-O-(C1-C6 alkyl)n-(CO)-, R3-(CO)-O-(C1-C6 alkyl)n-, R3-S-(CO)-(C1-C6 alkyl)n-, R3-O-(CO)-(C1-C6 alkyl)- or R3-O-(CO)-O-(C1-C6 alkyl)-, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “amino”, “amino C1-C6 alkyl”, “amino carbonyl”, “amino carbonyl C1-C6 alkyl” and “aminosulfonyl” are each independently unsubstituted or substituted by one or two groups selected from -Rn, -ORn, -(CO)Rn, -(CO)ORn, -(C1-C6 alkyl)-(CO)ORn, -(SO2)Rn, -(SO2)ORn, -(C1-C6 alkyl)-(SO2)Rn, -(CO)N(Ri2)2 and -(SO2)N(Ri2)2, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
R6 represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyano, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, C1-C6 alkoxy and C1-C6 alkoxy carbonyl;
R7, R7’, R8, R8’ each independently represent H, C1-C6 alkyl, halogen, halo C1-C6 alkyl, amino, hydroxy C1-C6 alkyl or C1-C6 alkoxy;
Xii independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl Cl-C6 alkyl or Q M x3 wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -ORb, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORI3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Xi2 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -ORi3, -SRi3, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Xi3, Xi4 each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl,
C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, or C, Xj3, XM, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or Ν=Λ I \ nitrogen-containing heterocyclyl, or N, X13, X14, taken together, form heterocyclyl , \__/, or with nitrogen atom at 1-position, wherein, the “Cl-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “aryl”, “aryl C1-C6 alkyl”, “heterocyclyl” and “heterocyclyl C1-C6 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SCbjRu» -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring, the “5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl” is unsubstituted or substituted by 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy carbonyl and benzyl, or . JQ> together with aryl or heterocyclyl forms a fused ring, the “ \and are unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl; R3, R4, R5 each independently represent H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SChjRu, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Ru independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, benzyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “phenyl” and “benzyl”are each independently unsubstituted or substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy;
R12 independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or N(Ri2)2 in -(CO)N(Ri2)2 or -(SO2)N(Ri2)2 independently e N \ il LÀ represents heterocyclyl V , '—/, or with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;
R13 independently represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl or phenyl substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy.
Still more preferably, X represents -CXiX2-(C1-C3 alkyl)n-, -(C1-C3 alkyl)-CXiX2-(Cl-C3 alkyl)n- or-(CH2)r-;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C3 alkyl, hydroxy C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C3 alkyl, halo C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylamino C1-C3 alkyl, aryl, heterocyclyl, aryl C1-C3 alkyl or heterocyclyl C1-C3 alkyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “aryl”, “heterocyclyl”, “aryl C1-C3 alkyl” and “heterocyclyl C1-C3 alkyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SC>2)Ri3,
-N(Rb)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring; and Xi, X2 are not hydrogen at the same time;
X5 représente H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6
O o O□
O S s-S^_^Xi211^ cycloalkenyl, heterocyclyl, aryl, xn, Xl1> X11, 0 Xl2, O ,
O O Xi3'n-*14
Π γ /'N'X13 'V%'X13 t^N'X13 \-Νγ-Χΐ3 -Af0*11 1ζ x14 , x-14 , X14 , x-14 or o , wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by 1, or 3 groups selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl,
O OO , , , ν°Ύ VS'Y y-n^Y Y^rTXl1 heterocyclyl, aryl, * xn, * xn, \ X11, xn, t υ χθγ0^ V13
O , X14 .
O .^-N X13 _V%'Xl3 /ό'Ν^ΤΧι3
Xi4 , X14 and X14 , the “C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl” and “aryl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and
-O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
or N(X5)2 represents ;-N^Xl3
Xl4 or heterocyclyl
nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;
X11 independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 ? ΤΎ 1 '
F3C7N'X) alkyl, aryl, aryl Cl-C3 alkyl or I wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “heterocyclyl”, “heterocyclyl C1-C3 alkyl”, “aryl” and “aryl C1-C3 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR43, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X12 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “heterocyclyl”, “heterocyclyl C1-C3 alkyl”, “aryl” and “aryl C1-C3 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X13, X14 each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl,
C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or C, X13, X14, taken together, form 5~8 membered saturated carbocyclyl, or \/NH, or N, X13, X14, taken together, form heterocyclyl
or
with nitrogen atom at 1-position, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “aryl”, “aryl C1-C3 alkyl”, “heterocyclyl” and “heterocyclyl C1-C3 alkyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo
C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -ORi3, -SRn, -(CO)ORn, -(SO2)R,3, -N(Ri3)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted
-OCH2CH2- or -OCH2O- form a fused ring, the “5~8 membered saturated carbocyclyl, or NH” is unsubstituted or substituted by 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6
N=A I \ alkoxy carbonyl and benzyl, or together with phenyl or thienyl forms a fused ring, the “ V , ï’-n^ VS ZO \__/, and are unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl.
ooo o rj^lA
S^N^O S^N^S O^N^O FaC^N^O
Further more preferably, Q represents Ι,Ι,Ι, I
In the définition of the compound represented by the above Formula and ail of the following structural formulas, the technical terms used, whether used alone or used in compound word, represent the following substituents: an alkyl having more than two carbon atoms may be linear or branched. For example, the alkyl in the compound Word -alkyl-(CO)ORn may be -CH2-, -CH2CH2-, -CH(CH3)-, -CH2CH2CH2-, -C(CH3)2-, and the like; -(CH2)r- may be -CH2CH2-, -CH2CH2CH2-, and the like. The alkyl is, for example, Ci alkyl: methyl; C2 alkyl: ethyl; C3 alkyl: propyl such as n-propyl or isopropyl; C4 alkyl: butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5 alkyl: pentyl such as n-pentyl; Cg alkyl: hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, the alkenyl is, for example, vinyl, allyl, l-methylprop-2-en-l-yl, 2-methylprop-2-en-l-yl, but-2-en-l-yl, butyl-3-en-l-yl, l-methylbut-3-en-l-yl and l-methylbut-2-en-l-yl. The alkynyl is, for example, ethynyl, propargyl, but-2-yn-l-yl, but-3-yn-l-yl, l-methylbut-3-yn-l-yl. The multiple bond(s) may be placed at any position of each unsaturated group. The cycloalkyl is a carbocyclic saturated ring System having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, the cycloalkenyl is monocycloalkenyl having, for example, three to six carbon ring 5 members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bond can be at any position. Halogen is fluorine, chlorine, bromine or iodine.
Unless otherwise specified, the aryl of the présent invention includes, but is not limited to,
etc., but also includes, but is not limited to,heteroaryl, which is an aromatic cyclic group having, for example, 3 to 6 ring atoms and optionally being fused with a benzo ring, and 1 to 4 (for example, 1, 2 , 3 or 4) heteroatoms of the ring are . -O -Ô selected from the group consisting of oxygen, nitrogen and sulfur. For example, N , N ,
If a group is substituted by a group, which should be understood to mean that the group is substituted by one or more groups, which are same or different groups, selected from the mentioned groups. In addition, the same or different substitution characters contained in the same or different substituents are independently selected, and may be the same or different. This is also applicable to ring Systems formed with different atoms and units. Meanwhile, the scope of the daims will exclude those compounds chemically unstable under standard conditions known to those skilled in the art.
In addition, unless specifically defined, the term occurring before or after multiple juxtaposed substituents (separated by or or) in the présent invention has a limiting effect on each of the substituents, such as the wording “unsubstituted or halogen-substituted” in the term “unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-” has a limiting effect on each group “-OCH2CH2-” “-OCH2O-” occurring thereafter; alkylamino refers to the amino group which is monosubstituted or disubstituted by alkyl, other substituted amino groups are similarly defined; a group (including heterocyclyl, aryl, etc.) without being specified a linking site may be attached at any site, including a C or N site; if it is substituted, the substituent may be substituted at any site as long as it comply with the valence bond theory. For example, if the heteroaryl
It should be pointed out that, when the carbon atom (C*) connected to Xi and X2 in the general formula is a chiral center (i.e., Xi and X2 are not the same), it is in R configuration or S configuration, preferably R configuration, and based on the content of stereoisomers having R and S configurations at this position, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), still more preferably 90-100% (R), still more preferably 95-100% (R). Wherein, “stereochemical purity” means the amount of the stated stereoisomer expressed as a percentage of the total amount of stereoisomers having the given chiral centre.
In the présent invention the stéréo Chemical configuration at the marked * position of formula I is fixed as being predominantly (R) according to the Cahn-Ingold-Prelog System, however is the subject matter of the invention is also directed to ail stereoisomers at other locants which are encompassed by formula I, and their mixtures. Such compounds of the formula I contain, e.g. one or more additional asymmetric carbon atoms or else double bonds which are not stated specifically in the formula I. It will be understood that the présent invention embraces both the pure isomers and more or less enriched mixtures thereof, where the asymmetric carbon atom in marked * position is in the R-configuration or, in mixtures, a compound or compounds of same Chemical constitution hâve the R-configuration in marked * position or are présent in a ratio that compounds having the R-configuration are predominantly présent (at least 60% R-configuration) whilst the other asymmetric carbon atom(s) may be présent in racemic form or are more or less resolved too. Provided the condition for the stereochemical configuration at marked * position is met, the possible stereoisomers which are defined by their spécifie spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are ail encompassed by formula I and can be obtained by customary methods from mixtures of the stereoisomers, or else be prepared by stereoselective reactions in combination with the use of stereochemically pure raw materials.
The invention also encompasses any keto and enol tautomer forms and mixtures and salts thereof, if respective functional groups are présent.
Stereoisomers can be obtained by optical resolution from the mixture obtained in the préparation. The stereoisomers may also be prepared selectively by using stereoselective reactions and using optically active raw materials and/or auxiliaries.lt is generally possible to use customary methods for optical resolutions (cf. Textbooks of Stereochemistry), for example following processes for separating mixtures into diastereomers, for example physical processes, such as crystallization, chromatographie processes, in particular column chromatography and high pressure liquid chromatography, distillation, if appropriate under reduced pressure, extraction and other processes, it is possible to separate the remaining mixtures of enantiomers, generally by chromatographie séparation on chiral solid phases. Suitable for préparative amounts or use on an industrial scale are processes such as the crystallization of diastereomeric salts which can be obtained from the compounds (I) using optically active acids and, if appropriate, provided that acidic groups are présent, using optically active bases.
A method for preparing the carboxylic acid derivative-substituted iminoaryl compound is provided, which comprises the following steps:
subjecting a compound represented by general formula II and a compound represented by general formula III’ to an élimination reaction to obtain a compound represented by general formula Γ, with the Chemical reaction équation shown as follows:
o □ □ ' □· or, subjecting a compound represented by general formula II and a compound represented by general formula III to an élimination reaction to obtain a compound represented by general formula I, with the Chemical reaction équation shown as follows:
Z^/^Y z-^/Y
JL + x^j/v ------JL X w
X3H Hal T xfy X4 X4 □ □ □ wherein, Hal represents halogen, other substituents Q, M, W, Y, Z, X, X3 and X4 are as defined above;
preferably, the reaction is carried out in the presence of a base and a solvent.
The base is at least one selected from inorganic bases (such as K2CO3, Na2CÛ3, CS2CO3, NaHCO3, KF, CsF, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe and the like) and organic bases (such as pyrazole, triethylamine, DIEA and the like).
The solvent is at least one selected from DMF, methanol, éthanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane and ethyl acetate.
In addition, when Q represents Re or
prepared by firstly preparing the intermediate product r6 , the target product can also be
through the above method, and then performing conventional substitution reaction with R6-Hal (Hal represents halogen, R6 represents alkyl, alkenyl, alkynyl, or haloalkyl).
The présent invention also provides a herbicidal composition, comprising (i) at least one of the carboxylic acid derivative-substituted iminoaryl compounds in a herbicidally effective amount; (component A); preferably, further comprising (ii) one or more other herbicides (component B) in a herbicidally effective amount and/or safeners; more preferably, further comprising (iii) a formulation auxiliary accepted in agricultural chemistry.
In a spécifie embodiment, the other herbicide is one or more selected from the following compounds and acids, salts and esters thereof:
(1) HPPD inhibitor selected from: topramezone(CAS NO.: 210631-68-8), isoxaflutole(CAS NO.: 141112-29-0), tembotrione(CAS NO.: 335104-84-2), tefuryltrione(CAS NO.: 473278-76-1), shuangzuocaotong(CAS NO.: 1622908-18-2), huanbifucaotong(CAS NO.: 1855929-45-1), sanzuohuangcaotong(CAS NO.: 1911613-97-2), benzuofucaotong(CAS NO.:
1992017-55-6), and (2) PDS inhibitor selected from: flurtamone (CAS NO.: 96525-23-4), diflufenican (CAS NO.: 83164-33-4), and picolinafen (CAS NO.: 137641-05-5);
(3) DOXP inhibitor selected from: clomazone (CAS NO.: 81777-89-1), and bixlozone (CAS NO.: 81777-95-9);
(4) ALS inhibitor selected from: tribenuron-methyl(CAS NO.: 101200-48-0), thifensulfuron methyl(CAS NO.: 79277-27-3), pyrazosulfuron-ethyl(CAS NO.: 93697-74-6), thiencarbazone-methyl(CAS NO.: 317815-83-1), halosulfuron methyl(CAS NO.: 100784-20-1), rimsulfuron(CAS NO.: 122931-48-0), nicosulfuron(CAS NO.: 111991-09-4), and imazamox(CAS NO.: 114311-32-9);
(5) ACCase inhibitor selected from: clethodim (CAS NO.: 99129-21-2), sethoxydim (CAS NO.: 74051-80-2), and quizalofop-P-methyl (CAS NO.: 100646-51-3);
(6) PPO inhibitor selected from: oxyfluorfen(CAS NO.: 42874-03-3), oxadiazon(CAS NO.: 19666-30-9), oxadiargyl(CAS NO.: 39807-15-3), sulfentrazone(CAS NO.: 122836-35-5), pyraclonil(CAS NO.: 158353-15-2), flumioxazin(CAS NO.: 103361-09-7), saflufenacil(CAS NO.: 372137-35-4), carfentrazone-ethyl(CAS NO.: 128639-02-1), and trifludimoxazin(CAS NO.: 1258836-72-4);
(7) PSII inhibitor selected from: metribuzin(CAS NO.: 21087-64-9), terbuthylazine(CAS NO.: 5915-41-3), amicarbazone(CAS NO.: 129909-90-6), chlorotoluron(CAS NO.: 15545-48-9), isoproturon(CAS NO.: 34123-59-6), bromacil(CAS NO.: 314-40-9), propaml(CAS NO.: 709-98-8), desmedipham(CAS NO.: 13684-56-5), phenmedipham(CAS NO.: 13684-63-4), bentazone(CAS NO.: 25057-89-0), and bromoxynil(CAS NO.: 1689-84-5);
(8) inhibitor of microtubule assembly selected from: butralin (CAS NO.: 33629-47-9), and pendimethalin (CAS NO.: 40487-42-1);
(9) VLCFA inhibitor selected from: butachlor (CAS NO.: 23184-66-9), pretilachlor (CAS NO.: 51218-49-6), mefenacet (CAS NO.: 73250-68-7), s-metolachlor (CAS NO.: 87392-12-9), flufenacet (CAS NO.: 142459-58-3), pyroxasulfone (CAS NO.: 447399-55-5), and anilofos (CAS NO.: 764249-01-0);
(10) lipid synthesis (non-acetyl-CoA carboxylase) inhibitor: prosulfocarb (CAS NO.: 52888-80-9);
(11) Synthetic hormone inhibitor selected from: , fluroxypyr(CAS
NO.: 69377-81-7), florpyrauxifen benzyl(CAS NO.: 1390661-72-9), halauxifen-methyl(CAS NO.: 943831-98-9), triclopyr(CAS NO.: 55335-06-3), clopyralid(CAS NO.: 1702-17-6), picloram(CAS NO.: 1918-02-1), aminopyralid(CAS NO.: 150114-71-9), dicamba(CAS NO.: 1918-00-9), 2-methyl-4-chlorophenoxyacetic acid(CAS NO.: 94-74-6), and 2,4-dichlorophenoxy acetic acid(CAS NO.: 94-75-7);
(12) EPSPS inhibitor: glyphosate (CAS NO.: 1071-83-6);
(13) GS inhibitor selected from: glufosinate ammonium (CAS NO.: 77182-82-2), and glufosinate-P-ammonium (CAS NO.: 35597-44-5);
(14) PSI inhibitor selected from: paraquat dichloride (CAS NO.: 1910-42-5), and diquat dibromide monohydrate (CAS NO.: 2764-72-9);
(15) Cellulose synthesis inhibitor selected from: triaziflam (CAS NO.: 131475-57-5), and indaziflam (CAS NO.: 950782-86-2);
(16) others: cinmethylin (CAS NO.: 87818-31-3).
In the context of the présent spécification, if an abbreviation of a generic name of an active compound is used, it includes in each case ali customary dérivatives, such as esters and salts, as well as isomers, in particular optical isomers, especially one or more commercially available forms. If the generic name dénotés an ester or a sait, it also includes in each case ail other conventional dérivatives, such as other esters and salts, free acids and neutral compounds, as well as isomers, in particular optical isomers, especially one or more commercially available forms. The Chemical name given to a compound means at least one compound encompassed by the generic name, and generally the preferred compound. In the case of sulfonamides such as sulfonylurea, salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group.
Wherein, the active ingrédient A to the active ingrédient B in the herbicidal composition is in a weight ratio of 1:1000—1000:1, 1:800—800:1 or 1:600—600:1, preferably 1:500—500:1, 1:400-400:1 or 1:300-300:1, more preferably 1:200-200:1, 1:100-100:1 or 1:80-80:1, further preferably 1:50-50:1, 1:30-30:1, 1:20-20:1, 1:10-10:1, 1:5-1:1 or 1:1-5:1. In some embodiments, the active ingrédients A and B together account for 1-95%, preferably 10-80%, of the total weight of the herbicidal composition.
The safener is selected from one or more of isoxadifen-ethyl (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), mefenpyr-diethyl (CAS: 135590-91-9), cloquintocet-mexyl (CAS: 99607-70-2), gibberellic acid (CAS: 77-06-5), fiirilazole (CAS: 121776-33-8), and metcamifen (CAS: 129531-12-0).
The préparation adjuvant comprises, for example, a carrier and/or a surfactant.
The term “carrier” herein refers to an organic or inorganic, naturel or synthetic substance, which facilitâtes the application of the active ingrédients. In general, the carrier is inert and must be agriculturally acceptable, especially is acceptable to a plant to be treated. The carrier may be a solid, such as clay, a naturel or synthetic silicate, silica, a resin, a wax, a solid fertilizer and so on; or a liquid such as water, an alcohol, a ketone, a petroleum fraction, an aromatic or paraffinic hydrocarbon, a chlorohydrocarbon, liquefied gas and so on.
The surfactant, which may be ionic or non-ionic, can include an emulsifier, a dispersant or a wetting agent. Examples which may be mentioned are a sait of polyacrylic acid, a sait of lignosulfonic acid, a sait of phenolsulfonic acid or of naphthalenesulfonic acid, a polymer of ethylene oxide with an aliphatic alcohol or with an aliphatic acid or with an aliphatic amine or with a substituted phénol (in particular, an alkylphenol or an arylphenol), a sulfosuccinate, a taurine dérivative (especially an alkyl taurate) and a phosphoric ester of an alcohol or of a polyhydroxyethylated phénol, an alkyl sulfonate, an alkylaryl sulfonate, an alkyl sulfate, a laurylether sulfate, a fatty alcohol sulfate, a sulfated hexadecanol, heptadecanol and octadecanol and a sulfated fatty alcohol polyglycol ether, and further include a condensate of naphthalene or naphthalenesulfonic acid with phénol and formaldéhyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, a polyethylene glycol alkylphenyl ether, a polyethylene glycol tributylphenyl ether, a polyethylene glycol tristearylphenyl ether, a alkylaryl polyether alcohol, an alcohol and fatty alcohol/ethylene oxide condensate, ethoxylated castor oil, a polyoxyethylene alkyl ether, an ethoxylated polyoxypropylene, a lauryl alcohol polyglycol ether acetal, a sorbitol ester, a lignin sulfite waste liquid, a protein, a denatured protein, a polysaccharide (e.g., methylcellulose), a hydrophobie modified starch, a polyvinyl alcohol, a polycarboxylate, a polyalkoxylate, a polyvinylamine, a polyvinylpyrrolidone, and a copolymer thereof. At least one surfactant may be required to facilitate dispersion of the active ingrédient in water and proper application thereof to a plant.
The composition can also comprise varions other components, such as a protective colloid, an adhesive, a thickener, a thixotropic agent, a pénétrant, a stabilizer, a chelating agent, a dye, a colorant or a polymer.
The composition of the présent invention may be diluted prior to use or used directly by users. The compositon can be prepared through a conventional processing method, that is, the active ingredient(s) is mixed with a liquid solvent or a solid carrier, and then one or more of the surfactants such as a dispersant, a stabilizer, a wetting agent, an adhesive, or a defoaming agent, etc. are added.
The herbicidal composition may be in a form of a formulation which is selected from: a dispersible oil suspension, a water suspension, a suspoemulsion, a wettable powder, an emulsifiable concentrate, a water-dispersible granule (a dry suspension), an aqueous émulsion and a microemulsion.
In short, the composition of the présent invention can be mixed with solid and liquid additives conventionally used in formulations of the prior art. As the extemal conditions change, the amount of active ingrédients used is also different. The extemal conditions are, for example, température, humidity, the nature of the herbicide used, etc. It can hâve a large variation range, for example between 0.001 and 1.0 kg/ha, or more active substances, but preferably between
0.005 and 750 g/ha, especially between 0.005 and 500 g/ha.
A method for controlling an undesirable plant is provided, which comprises applying at least one of the carboxylic acid derivative-substituted iminoaryl compounds or the herbicidal composition in a herbicidally effective amount on a plant or in its area or to soil or water to control the emergence or growth of undesirable plant.
Use of at least one of the carboxylic acid derivative-substituted iminoaryl compounds or the herbicidal composition for controlling a undesirable plant; preferably, the carboxylic acid derivative-substituted iminoaryl compound is used to control a weed in a useful crop, the useful crop is a genetically modified crop or a crop treated by genome editing technique.
The compounds of the formula I according to the invention hâve an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants (undesirable plants). The active compounds also act efficiently on perennial weeds which produce shoots from rhizomes, root stocks or other perennial organs and which are difficult to control. In this context, it is generally immaterial whether the substances are applied pre-sowing, pre-emergence or post-emergence. Specifically, examples may be mentioned of some représentatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without these being a restriction to certain species. Examples of weed species on which the active compounds act efficiently are, from amongst the monocotyledons, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species from the annual sector and from amongst the perennial species Agropyron, Cynodon, Imperata and Sorghum, and also perennial Cyperus species.
In the case of the dicotyledonous weed species, the spectrum of action extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon from amongst the annuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds. The active compounds according to the invention also effect outstanding control of harmful plants which occur under the spécifie conditions of rice growing such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. If the compounds according to the invention are applied to the soil surface prior to germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they hâve reached the cotylédon stage but then their growth stops, and, eventually, after three to four weeks hâve elapsed, they die completely. In particular, the compounds according to the invention exhibit excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor and against Amaranthus, Galium and Kochia species.
The undesirable plants also include herbicide-resistant or tolérant weed species.
Although the compounds according to the invention hâve an excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, rice, corn, sugarbeet, cotton and soya, are not damaged at ail, or only to a negligible extent. In particular, they hâve excellent compatibility in cereals, such as wheat, barley and corn, in particular wheat. For these reasons, the présent compounds are highly suitable for selectively controlling undesirable plant growth in plantings for agricultural use or in plantings of omamentals.
Owing to their herbicidal properties, these active compounds can also be employed for controlling harmfiil plants in crops of known or still to be developed genetically engineered plants. The transgenic plants generally hâve particularly advantageous properties, for example résistance to certain pesticides, in particular certain herbicides, résistance to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fiingi, bacteria or viruses. Other particular properties relate, for example, to the quantity, quality, storage-stability, composition and to spécifie ingrédients of the harvested product. Thus, transgenic plants having an increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested produce are known.
The use of the compounds of the formula I according to the invention or their salts in economically important transgenic crops of usefiil and omamental plants, for example of cereal, such as wheat, barley, rye, oats, millet, rice, maniok and corn, or else in crops of sugarbeet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species is preferred. The compounds of the formula I can preferably be used as herbicides in crops of usefiil plants which are résistant or which hâve been made résistant by genetic engineering toward the phytotoxic effects of the herbicides.
Conventional ways for preparing novel plants which hâve modified properties compared to known plants comprise, for example, traditional breeding methods and the génération of mutants. Altematively, novel plants having modified properties can be generated with the aid of genetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0 131 624). For example, there hâve been described several cases of:
- genetically engineered changes in crop plants in order to modify the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806),
- transgenic crop plants which are résistant to certain herbicides of the glufosinate- (cf., for example, EP-A 0 242 236, EP-A 0 242 246) or glyphosate-type (WO 92/00377), or of the sulfonylurea-type (EP-A 0 257 993, U.S. Pat. No. 5,013,659A),
- transgenic crop plants, for example cotton, having the ability to produce Bacillus thuringiensis toxins (Bt toxins) which impart résistance to certain pests to the plants (EP-A 0 142 924, EP-A0 193 259),
- transgenic crop plants having a modified fatty acid composition (WO 91/13972).
Numerous molecular biological techniques which allow the préparation of novel transgenic plants having modified properties are known in principle; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker Gene und Klone [Genes and Clones], VCH Weinheim, 2nd édition 1996, or Christou, Trends in Plant Science 1 (1996) 423-431). In order to carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molécules into plasmids which allow a mutagenesis or a change in the sequence to occur by recombination of DNA sequences. Using the abovementioned standard processes it is possible, for example, to exchange bases, to remove partial sequences or to add naturel or synthetic sequences. To link the DNA fragments with each other, it is possible to attach adaptors or linkers to the fragments.
Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.
To this end it is possible to employ both DNA molécules which comprise the entire coding sequence of a gene product including any flanking sequences that may be présent, and DNA molécules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which hâve a high degree of homology to the coding sequences of a gene product but which are not entirely identical.
When expressing nucleic acid molécules in plants, the synthesized protein can be localized in any desired compartment of the plant cells. However, to achieve localization in a certain compartment, it is, for example, possible to link the coding région with DNA sequences which ensure localization in a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
The transgenic plant cells can be regenerated to whole plants using known techniques. The transgenic plants can in principle be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants. In this manner, it is possible to obtain transgenic plants which hâve modified properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.
When using the active compounds according to the invention in transgenic crops, in addition to the effects against harmful plants which can be observed in other crops, there are frequently effects which are spécifie for the application in the respective transgenic crop, for example a modified or specifically broadened spectrum of weeds which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crops are résistant, and an effect on the growth and the yield of the transgenic crop plants. The invention therefore also provides for the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
In addition, the substances according to the invention hâve outstanding growth-regulating properties in crop plants. They engage in the plant metabolism in a regulating manner and can this be employed for the targeted control of plant constituents and for facilitating harvesting, for example by provoking desiccation and stunted growth. Furthermore, they are also suitable for generally regulating and inhibiting undesirable végétative growth, without destroying the plants in the process. Inhibition of végétative growth plays an important rôle in many monocotyledon and dicotyledon crops because lodging can be reduced hereby, or prevented completely.
The compounds according to the invention can be applied in the customary formulations in the form of wettable powders, emulsifiable concentrâtes, sprayable solutions, dusts or granules. The invention therefore also provides herbicidal compositions comprising compounds of the formula I. The compounds of the formula I can be formulated in varions ways depending on the prevailing biological and/or chemico-physical parameters. Examples of suitable formulation options are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrâtes, emulsifiable concentrâtes (EC), émulsions (EW), such as oil-in-water and water-in-oil émulsions, sprayable solutions, suspension concentrâtes (SC), oil dispersions (OD), oil- or water-based dispersions, oil-miscible solutions, dusts (DP), capsule suspensions (CS), seed-dressing compositions, granules for broadeasting and soil application, granules (GR) in the form of microgranules, spray granules, coating granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in Winnacker-Küchler, Chemische Technologie [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition 1986; Wade van Valkenburg, Pesticide Formulations, Marcel Dekker, N.Y., 1973; K. Martens, Spray Drying Handbook, 3rd Ed. 1979, G Goodwin Ltd. London.
The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, Introduction to Clay Colloid Chemistry; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, Solvents Guide; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's Détergents and Emulsifïers Annual, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964; Schônfeldt, Grenzflüchenaktive Àthylenoxidaddkte [Surface-active ethylene oxide adducts], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler, Chemische Technologie [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.
Wettable powders are préparations which are uniformly dispersible in water and which contain, in addition to the active compound and as well as a diluent or inert substance, surfactants of ionic and/or nonionic type (wetting agents, dispersants), for example polyethoxylated alkyl phénols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutyinaphthalenesulfona-te or else sodium oleoylmethyltaurinate. To préparé the wettable powders, the herbicidally active compounds are frnely ground, for example in customary apparatus such as hammer mills, fan mills and air-jet mills, and are mixed simultaneously or subsequently with the formulation auxiliaries.
Emulsifiable concentrâtes are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatic compounds or hydrocarbons or mixtures of the solvents, with the addition of one or more surfactants of ionic and/or nonionic type (emulsifïers). Examples of emulsifïers which can be used are calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifïers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.
Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, naturel clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrâtes can be water- or oil-based. They can be prepared, for example, by wet milling using commercially customary bead mills, with or without the addition of surfactants as already mentioned above, for example, in the case of the other formulation types.
Emulsions, for example oil-in-water émulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if desired, surfactants as already mentioned above, for example, in the case of the other formulation types.
Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active-compound concentrâtes to the surface of carriers such as sand, kaolinites or granulated inert material, by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or else minerai oils. Suitable active compounds can also be granulated in the manner which is customary for the préparation of fertilizer granules, if desired as a mixture with fertilizers. Water-dispersible granules are generally prepared by the customary processes, such as spray-drying, fluidized-bed granulation, disk granulation, mixing using high-speed mixers, and extrusion without solid inert material.
For the préparation of disk, fluidized-bed, extrader and spray granules, see for example processes in Spray-Drying Handbook 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, Agglomération, Chemical and Engineering 1967, pages 147 ff.; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products, see for example G C. Klingman, Weed Control as a Science, John Wiley and Sons Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, Weed Control Handbook, 5th Ed., Blackwell Scientifîc Publications, Oxford, 1968, pages 101-103.
The agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula I. In wettable powders the concentration of active compound is, for example, from about 10 to 99% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrâtes the concentration of active compound can be from about 1 to 90%, preferably from 5 to 80%, by weight. Formulations in the form of dusts contain from 1 to 30% by weight of active compound, preferably most commonly from 5 to 20% by weight of active compound, while sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50%, by weight of active compound. In the case of water-dispersible granules the content of active compound dépends partly on whether the active compound is in liquid or solid form and on the granulation auxiliaries, Allers, etc. that are used. In water-dispersible granules the content of active compound, for example, is between 1 and 95% by weight, preferably between 10 and 80% by weight.
In addition, the formulations of active compound may comprise the tackifiers, wetting agents, dispersants, emulsifiers, pénétrants, preservatives, antifreeze agents, solvents, Allers, carriers, colorants, antifoams, évaporation inhibitors and pH and viscosity regulators which are customary in each case.
Based on these formulations it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a ready-mix or tank mix.
Suitable active compounds which can be combined with the active compounds according to the invention in mixed formulations or in a tank mix are, for example, known active compounds as described in for example World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and in the literature cited therein. For example the following active compounds may be mentioned as herbicides which can be combined with the compounds of the formula I (note: the compounds are either named by the common name in accordance with the International Organization for Standardization (ISO) or by the Chemical names, if appropriate together with a customary code number): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, ethachlor, napropamide, R-Ieft handed napropamide, propanil, mefenacet, diphenamid, diflufenican, ethaprochlor, beflubutamid, bromobutide, dimethenamid, dimethenamid-P, etobenzanid, flufenacet, thenylchlor, metazachlor, isoxaben, flamprop-M-methyl, flamprop-M-propyl, allidochlor, pethoxamid, chloranocryl, cyprazine, mefluidide, monalide, delachlor, prynachlor, terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor, clomeprop, propyzamide, pentanochlor, carbetamide, benzoylprop-ethyl, cyprazole, butenachlor, tebutam, benzipram, mogrton, dichlofluanid, naproanilide, diethatyl-ethyl, naptalam, flufenacet, EL-177, benzadox, chlorthiamid, chlorophthalimide, isocarbamide, picolinafen, atrazine, simazine, prometryn, cyanatryn, simetryn, ametryn, propazine, dipropetryn, SSH-108, terbutryn, terbuthylazine, triaziflam, cyprazine, proglinazine, trietazine, prometon, simetone, aziprotryne, desmetryn, dimethametryn, procyazine, mesoprazine, sebuthylazine, secbumeton, terbumeton, methoprotryne, cyanatryn, ipazine, chlorazine, atraton, pendimethalin, eglinazine, cyanuric acid, indaziflam, chlorsulfuron, metsulfuron-methyl, bensulfuron methyl, chlorimuron-ethyl, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, iodosulfuron-methyl sodium, foramsulfuron, cinosulfuron, triasulfuron, sulfometuron methyl, nicosulfuron, ethametsulfuron-methyl, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, azimsulfuron, flazasulfuron, monosulfuron, monosulfuron-ester, flucarbazone-sodium, flupyrsulfuron-methyl, halosulfuron-methyl, oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, sodium metsulfuron methyl, flucetosulfuron, HNPC-C, orthosulfamuron, propyrisulfuron, metazosulfuron, acifluorfen, fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlomitrofen, aclonifen, ethoxyfen-ethyl, bifenox, nitrofluorfen, chlomethoxyfen, fluorodifen, fluoronitrofen, furyloxyfen, nitrofen, TOPE, DMNP, PPG1013,
AKH-7088, halosafen, chlortoluron, isoproturon, linuron, diuron, dymron, fluometuron, benzthiazuron, methabenzthiazuron, cumyluron, ethidimuron, isouron, tebuthiuron, buturon, chlorbromuron, methyldymron, phenobenzuron, SK-85, metobromuron, metoxuron, afesin, monuron, siduron, fenuron, fluothiuron, neburon, chloroxuron, noruron, isonoruron, 3-cyclooctyl-l, thiazfluron, tebuthiuron, difenoxuron, parafluron, methylamine tribunil, karbutilate, trimeturon, dimefuron, monisouron, anisuron, methiuron, chloreturon, tetrafluron, phenmedipham, phenmedipham-ethyl, desmedipham, asulam, terbucarb, barban, propham, chlorpropham, rowmate, swep, chlorbufam, carboxazole, chlorprocarb, fenasulam, BCPC, CPPC, carbasulam, butylate, benthiocarb, vemolate, molinate, triallate, dimepiperate, esprocarb, pyributicarb, cycloate, avadex, EPTC, ethiolate, orbencarb, pebulate, prosulfocarb, tiocarbazil, CDEC, dimexano, isopolinate, methiobencarb, 2,4-D butyl ester, MCPA-Na, 2,4-D isooctyl ester, MCPA isooctyl ester, 2,4-D sodium sait, 2,4-D dimethyla mine sait, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high 2,4-D propionic acid sait, 2,4-D butyric acid, MCPA propionic acid, MCPA propionic acid sait, MCPA butyric acid, 2,4,5-D, 2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine sait, dicamba, erbon, chlorfenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-ethy, fenoxaprop-p-ethyl, propaquizafop, cyhalofop-butyl, metamifop, clodinafop-propargyl, fenthiaprop-ethyl, chloroazifop-propynyl, poppenate-methyl, trifopsime, isoxapyrifop, paraquat, diquat, oryzalin, ethalfluralin, isopropalin, nitralin, profluralin, prodinamine, benfluralin, fluchloraline, dinitramina, dipropalin, chlomidine, methalpropalin, dinoprop, glyphosate, anilofos, glufosinate ammonium, amiprophos-methyl, sulphosate, piperophos, bialaphos-sodium, bensulide, butamifos, phocarb, 2,4-DEP, H-9201, zytron, imazapyr, imazethapyr, imazaquin, imazamox, imazamox ammonium sait, imazapic, imazamethabenz-methyl, fluroxypyr, fluroxypyr isooctyl ester, clopyralid, picloram, trichlopyr, dithiopyr, haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid, diflufenzopyr, triclopyr-butotyl, Cliodinate, sethoxydim, clethodim, cycloxydim, alloxydim, clefoxydim, butroxydim, tralkoxydim, tepraloxydim, buthidazole, metribuzin, hexazinone, metamitron, ethiozin, ametridione, amibuzin, bromoxynil, bromoxynil octanoate, ioxynil octanoate, ioxynil, dichlobenil, diphenatrile, pyraclonil, chloroxynil, iodobonil, flumetsulam, florasulam, penoxsulam, metosulam, cloransulam-methyl, diclosulam, pyroxsulam, benfuresate, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, benzobicylon, mesotrione, sulcotrione, tembotrione, tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone, fenoxasulfone, methiozolin, fluazolate, pyraflufen-ethyl, pyrazolynate, difenzoquat, pyrazoxyfen, benzofenap, nipyraclofen, pyrasulfotole, topramezone, pyroxasulfone, cafenstrole, flupoxam, aminotriazole, amicarbazone, azafenidin, carfentrazone-ethyl, sulfentrazone, bencarbazone, benzfendizone, butafenacil, bromacil, isocil, lenacil, terbacil, flupropacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, propyzamide, MK-129, flumezin, pentachlorophenol, dinoseb, dinoterb, dinoterb acetate, dinosam, DNOC, chloronitrophene, medinoterb acetate, dinofenate, oxadiargyl, oxadiazon, pentoxazone, Flufenacet, fluthiacet-methyl, fentrazamide, flufenpyr-ethyl, pyrazon, brompyrazon, metflurazon, kusakira, dimidazon, oxapyrazon, norflurazon, pyridafol, quinclorac, quinmerac, bentazone, pyridate, oxaziclomefone, benazolin, clomazone, cinmethylin, ZJ0702, pyribambenz-propyl, indanofan, sodium chlorate, dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, flupropanate, cyperquat, bromofenoxim, epronaz, methazole, flurtamone, benfuresate, ethofumesate, tioclorim, chlorthal, fluorochloridone, tavron, acrolein, bentranil, tridiphane, chlorfenpropmethyl, thidiarizonaimin, phenisopham, busoxinone, methoxyphenone, saflufenacil, clacyfos, chloropon, alorac, diethamquat, etnipromid, iprymidam, ipfencarbazone, thiencarbazone-methyl, pyrimisulfan, chlorflurazole, tripropindan, sulglycapin, prosulfalin, cambendichlor, aminocyclopyrachlor, rodethanil, benoxacor, fenclorim, flurazole, fenchlorazole-ethyl, cloquintocet-mexyl, oxabetrinil, MG/91, cyometrinil, DKA-24, mefenpyr-diethyl, furilazole, fluxofenim, isoxadifen-ethyl, dichlormid, halauxifen-methyl, DOW florpyrauxifen, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.
For use, the formulations which are présent in commercially available form are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrâtes, dispersions and water-dispersible granules. Products in the form of dusts, granules for soil application or broadcasting and sprayable solutions are usually not further diluted with other inert substances prior to use. The application rate of the compounds of the formula I required varies with the extemal conditions, such as température, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha or more of active substance, but it is preferably between 0.005 and 750 g/ha, especially between 0.005 and 250g/ha.
Spécifie Mode for Carrying out the Invention
The following embodiments are used to illustrate the présent invention in detail and should not be taken as any limit to the présent invention. The scope of the invention would be explained through the Claims.
In view of économies and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table 1 and Table A. The structure and information of a certain compound are shown in Table 1 and Table A. The compounds in Table 1 and Table A are listed for further explication of the présent invention, other than any limit therefor. The subject of the présent invention should not be interpreted by those skilled in the art as being limited to the following compounds.
Table 1 : Structures and 'H NMR data of compounds rAA^NYXYW
Q M X3
X4 □
NO. | Q | X | X3 | X4 | w | Y | Z | M | ‘HNMR |
1 | ω / K -z >0 □H | CH(Me) | 0 | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.49 (s, 1H), 8.01 (d, 7=7.5 Hz, 1H), 7.88 (d, 7=9.5 Hz, 1 H), 4.89-4.87 (m, 1H), 3.68 (s, 3H), 3.62 (s, 6H), 1.47-1.45 (m, 3H). |
2 | ' ω | CH(Me) | O | O | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.49 (s, 1H), 8.01 (d, J= 7.5Hz, 1H), 7.88 (d, 7= 9.5 Hz, 1H), 4.87-4.85 (m, 1H), 4.15-4.13 (m, 2H), 3.61 (s, 6H), 1.46-1.44 (m, 3H), 1.18 (t, 7=7.5 Hz, 3H). |
3 | ω / H-z >0 | CH(Me) | O | S | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 8.00 (d, 7= 7.5 Hz, 1H), 7.89 (d, 7=9.5 Hz, 1H), 5.08 (q, 7= 6.5 Hz, 1H), 4.57 (q, 7= 7.0 Hz, 2H), 3.63 (s, 6H), 1.51 (d,7=6.5 Hz, 3H), 1.35 (t, 7= 7.0 Hz, 3H). |
4 | 0 S^N^O 1 | CH(Me) | O | O | '/-0^ | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.52 (s, 1 H), 8.02 (d, 7= 8.0 Hz, 1H), 7.89 (d, 7=9.5 Hz, 1H), 4.88 (q, 7= 7.0 Hz, 1H), 4.14-4.01(m, 2H), 3.64 (s, 6H), 1.63-1.56 (m, 2H), 1.48 (d, 7= 7.0 Hz, 3H), 0.87 (t,7=7.5 Hz, 3H). |
5 | Ο '''Ν'^ΐΑ S^N'X) 1 | CH(Me) | O | O | cA | Cl | F | CH | ’HNMR(500 MHz, DMSO-</6) 8 8.51 (s, 1H), 8.02 (d, 7=8.0 Hz, 1H), 7.89 (d, 7= 9.5 Hz, 1H), 5.00-4.95 (m, 1 H), 4.82 (q, 7= 7.0 Hz, 1H), 3.64 (s, 6H), 1.46 (d, 7= 7.0 Hz, 3H), 1.22-1.18 (m, 6H). |
6 | ω / -Ζ >Ο | CH(Me) | O | O | Cl | F | CH | Ή NMR(500 MHz, DMSO-ds) δ 8.50 (s, 1H), 8.02 (d, 7= 7.5 Hz, 1H), 7.90 (d, 7= 9.5 Hz, 1H), 5.84-5.65 (m, 1H), 5.16-4.98 (m, 2H), 4.87 (q, 7= 7.0 Hz, 1H), 4.29-4.16 (m, 1 H), 4.16-4.09 (m, 1H), 3.67- 3.61 (s, 6H), 2.41-2.31 (m, 2H), 1.47 (d, 7= 7.0 Hz, 3H). | |
7 | Ο -Λ,λ S^N^O | CH(Me) | O | 0 | A o | Cl | F | CH | |
3 | Ο S^N^O 1 | CH(Me) | O | O | 0^ K | Cl | F | CH | |
9 | ω / Η -ζ >0 οΑ | CH(Me) | O | 0 | /O | Cl | F | CH | ‘HNMR(500 MHz, DMSO-76) δ 8.52 (s, 1H), 8.03 (d, 7= 7.5 Hz, 1H), 7.89 (d, 7=9.5 Hz, 1H), 4.89 (q, 7= 7.0 Hz, 1H), 4.02-3.92 (m, 1H), 3.64 (s, 6H), 1.49 (d, 7= 7.0 Hz, 3H), 1.31 -1.25 (m, 1H), 0.52-0.48 (m, 2H), 0.30-0.23 (m,2H). |
10 | 0 Άΐ S^N^O | CH(Me) | O | O | Cl | F | CH | ‘H NMR(500 MHz, DMSO-ds) δ 8.53 (s, 1 H), 8.03 (d, 7= 7.5 Hz, 1H), 7.90 (d, 7=9.5 Hz, 1H), 4.94 (q, 7= 7.0 Hz, 1 H), 4.68 (t, 7=4.0 Hz, 1H), 4.59 (t, 7= 4.0 Hz, 1 H), 4.50 — 4.29 (m,2H), 3.64 (s, 6H), 1.50 (d, 7= 7.0 Hz,3H). |
II | Ο S^N^O 1 | CH(Me) | O | o | /-O 'F | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfs) δ 8.52 (s, 1H), 8.02 (d, 7= 7.5 Ηζ,ΙΗ), 7.90 (d, 7= 9.0 Hz, 1H), 4.90 (q, 7=7.0 Hz, IH), 4.54 (ζ 7= 6.0 Hz, 1H), 4.44 (t, 7 =6.0 Hz, 1H), 4.29-4.16 (m, 2H), 3.64 (s, 6H), 2.04-1.96 (m, 2H), 1.48 (d, 7=7.0 Hz, 3H). |
12 | ' tn | CH(Me) | O | o | /'O Xf3 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-î/s) δ 8.53 (s, 1H), 8.02 (d, 7= 7.5 Hz, 1H), 7.89 (d, 7=9.0 Ηζ,ΙΗ), 4.91 (q, 7=7.0 Hz, 1H), 4.23-4.13 (m, 2H), 3.64 (s, 6H), 2.33-2.27 (m, 2H), 1.84-1.82 (m, 2H), 1.49 (d, 7= 7.0 Hz, 3H). |
13 | ω / H -Z >O | CH(Me) | O | o | ho \ | Cl | F | CH | |
14 | ω , -z >0 | CH(Me) | o | o | Ao 0^ | Cl | F | CH | ‘H NMR (500 MHz, ChIorofonn-7) δ 8.55 (s, 1H), 7.91 (d,7= 8.0 Hz, 1H), 7.36 (d, 7=9.0 Ηζ,ΙΗ), 4.88 (q, 7= 7.0 Hz, 1H), 4.45 — 4.28 (m, 2H), 3.82 (s, 6H), 3.65 (t, 7= 4.5 Hz,2H), 3.40 (s, 3H), 1.62-1.58 (m, 3H). |
15 | O S^N^O 1 | CH(Me) | o | 0 | /0 | Cl | F | CH | |
16 | ô S^N^O 1 | CH(Me) | o | o | /'O X \ | CI | F | CH | |
17 | ω / Xo <Μ | CH(Me) | o | o | o | Cl | F | CH | ‘H NMR (500 MHz, Chloroform-7) δ 8.55 (s, 1H), 7.92 (d, 7= 8.0 Hz, 1 H), 7.36 (d, 7= 9.0 Hz, 1H), 4.90 (q, 7= 7.0 Hz, 1H), 4.344.20 (m, 4H), |
3.81 (s,6H), 1.62-1.58 (oi, 3H), 1.33-1.31 (m, 3H). | |||||||||
18 | ω , Η-ζ >ο | CH(Me) | O | O | 0 | Cl | F | CH | |
19 | 7 ω | CH(Me) | O | O | Λο K ΛοΑο | Cl | F | CH | |
20 | Ο 'ν'^ιΑ s^n^o | CH(Me) | 0 | O | /-o | Cl | F | CH | ‘HNMR(500 MHz, DMSO) δ 8.54 (s, 1H), 8.03 (d, J =7.5 Hz, 1 H), 7.91 (d, J= 9.5Hz, 1H), 5.01 (q, .7=7.0 Hz, IH), 3.63 (s, 6H), 1.99-1.96 (m, 6H), 1.53 (d, J = 7.0 Hz, 3H). |
21 | ω / -Ζ >Ο | CH(Me) | 0 | O | /—o 0 | Cl | F | CH | |
22 | ω / -ζΗο | CH(Me) | O | O | /—O 0 | Cl | F | CH | |
23 | ο S^N^O | CH(Me) | O | O | /O \ Λ | Cl | F | CH | |
24 | ω / Η -Ζ >=Ο <Η | CH(Me) | O | O | /- ο | Cl | F | CH | ‘H NMR (500 MHz, Chloroform-rf) δ 8.50 (s, IH), 7.86 (d, .7=7.5 Hz, lH),7.30(d, .7=9.0 Hz, 1 H), 4.83 (q, J =6.5 Hz, 1 H), 4.26- 4.19 (m, IH), 4.16-4.02 (m, 2H), 3.87-3.80 (m, IH), 3.78-3.74 (m, 7H), 1.97-1.94(m, IH), 1.91-1.82 (m, 2H), 1.65- 1.57(oi, IH), 1.54 (d,J= 6.5 Hz, 3H). |
25 | ' <η | CH(Me) | O | s | /-ο \^,o^ | Cl | F | CH |
26 | ' en | CH(Me) | O | O | /O 1,0. VJ | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.50 (s, 1H), 8.02 (d,J= 7.5 Hz, 1H), 7.90 (d, ./=9.5 Hz, 1 H), 7.66 (d,J= 2.5 Hz, 1H), 6.54 (d, ./=2.5 Hz, 1H), 6.45-6.42 (m, 1H), 5.18-5.16 (m, 2H), 4.92 -4.9 l(m, 1H), 3.64 (s, 6H), 1.46 (d,J= 7.0 Hz, 3 H). |
27 | v° 7 ω | CH(Me) | O | O | /O \ s VJ | Cl | F | CH | |
28 | v° °=y~ ' en | CH(Me) | O | O | ^O\ ,S^ VJ | Cl | F | CH | |
29 | ' en | CH(Me) | O | O | <·° L ZI | Cl | F | CH | |
30 | Ô S^N^O 1 | CH(Me) | O | O | Vo \ | Cl | F | CH | |
31 | 7 en | CH(Me) | O | O | /° 1 SiS N | Cl | F | CH | |
32 | ω / K -Z >o | CH(Me) | O | O | V° i J f1 chf2 | Cl | F | CH | |
33 | ô ^ν^γΑ S^N^O 1 | CH(Me) | O | O | 7P_\^c°2Et N^° | Cl | F | CH | |
34 | en / H. -Z >o | CH(Me) | 0 | 0 | Vo \ 3. V . | Cl | F | CH | |
35 | O 'Ν'^ΐΑ S^N^O | CH(Me) | O | O | J Ο-Λ \=N | Cl | F | CH | |
36 | O S^N^O | CH(Me) | O | O | °-A | Cl | F | CH |
37 | ω , W -ζ >0 | CH(Me) | O | O | / ?λ O ___) Zr~Z O | Cl | F | CH | |
38 | ο S^N^O 1 | CH(Me) | O | 0 | ho \ Ό. V 11 N-N | Cl | F | CH | |
39 | ω , Η -ζ >ο | CH(Me) | O | O | N-N | Cl | F | CH | |
40 | Μ ' U) | CH(Me) | O | O | /~-o 1 S(N'N | CI | F | CH | |
41 | ω / _ζΚο ο^Χ | CH(Me) | O | O | /-ο 1 V'N | Cl | F | CH | |
42 | ω > Η_ -ζ >Ο | CH(Me) | O | 0 | /Ό | Cl | F | CH | Ή NMR(500 MHz, DMSCWî) 6 8.51 (s, 1H), 8.04 (d,J= 7.5 Hz, 1 H), 7.91 (d, J=9.5Hz, 1H), 7.37-7.27 (tn, 5H), 5.25 (d,J= 12.5 Hz, 1H), 5.16 (d,J= 12.5 Hz, 1H), 4.96 (q, ./=7.0 Hz, 1H), 3.64 (d,J= 6.0Hz, 6H), 1.50 (d, J =7.0 Hz, 3H). |
43 | (Λ / κ >° οΗ | CH(Me) | O | 0 | A° \ | Cl | F | CH | |
44 | ω , Η -ζ >ο ο^Χ | CH(Me) | O | O | /0 | Cl | F | CH | |
45 | ο S^N^O 1 | CH(Me) | O | O | Cl | F | CH | ||
46 | 0 S^N^O 1 | CH(Me) | O | O | ^°\ z^/CF3 | Cl | F | CH | |
47 | Ô S^N^O 1 | CH(Me) | 0 | O | /^o C^'NO2 | Cl | F | CH |
48 | ω / -Ko οΑ | CH(Mc) | O | O | Aq | Cl | F | CH | |
49 | ô hKrA | CH(Me) | O | O | Ao OMe | Cl | F | CH | |
50 | ω / Η >0 cA | CH(Me) | O | O | Ao 'L~~~C^~'SEt | Cl | F | CH | |
51 | Ο ^hKbA S^hKo 1 | CH(Me) | O | O | AO__/NH2 1K | Cl | F | CH | |
52 | ω , Κ -2 >0 οΑ | CH(Me) | O | O | Ao 'Î'~^Z/^~-SO2Me | Cl | F | CH | |
53 | j-Λ °Κ’ ' V) | CH(Me) | O | O | Ao COOEt AK | Cl | F | CH | |
54 | ο 'tKrA S^KK) 1 | CH(Me) | O | O | Ao \ jo | Cl | F | CH | |
55 | ω ζ Ά -ζ >0 οΑ | CH(Me) | O | O | A*O /\ AK | Cl | F | CH | |
56 | °αα ' ω | CH(Me) | O | O | AK~COOH | Cl | F | CH | |
57 | Ο >Λ,λ S^N^O 1 | CH(Me) | O | O | Ao F\ OMe aX | Cl | F | CH | |
58 | ο 'hKtA S^tjl^o | CH(Me) | O | O | A r0 / Z Aa | Cl | F | CH | |
59 | 0 α,α S^N^O 1 | CH(Me) | O | O | ho AK | Cl | F | CH | 1HNMR(5OO MHz, Chloroform-d) δ 8.65 (s, 1H), 8.53-8.48 (m, 2H), 7.86 (d,J = 8.0 Hz, 1 H), 7.70 (d, J = 8.0 Hz, 1H), 7.37 (d, J = 9.0 Hz, 1 H), 7.28-7.30 (m, 1H), 5.26 (s, |
2H), 4.92 (q, J = 7.0 Hz, 1H), 3.83 (s, 6H), 1.62 (d, J = 7.0 Hz, 3H). | |||||||||
60 | ω / -Ho | CH(Me) | O | O | Λο | Cl | F | CH | ‘HNMR(500 MHz, Chloroform-J) δ 8.58 (d,J= 5.0 Hz, 2H), 8.55 (s, 1H), 7.72 (d, J= 5.0 Ha 2H), 7.47 (d,7=8.0 Hz, 1H), 7.36 (d,J= 9.0 Hz, 1 H), 5.26 (s, 2H), 4.92 (q, 7=7.0 Ha 1H), 3.83 (s, 6H), 1.62 (d, 7= 7.0 Ha3H). |
61 | ω , >-< -ζ >Ο Ο <·* | CH(Me) | O | O | /'O | Cl | F | CH | |
62 | ω / Η -Ζ >Ο | CH(Me) | 0 | O | Ao A3 | Cl | F | CH | |
63 | Ο S^N^O 1 | CH(Me) | 0 | 0 | AV-n | Cl | F | CH | |
64 | ω / ι Η -ζ >ο | CH(Me) | O | O | γν. _-O O | Cl | F | CH | |
65 | ω / A -Ζ >Ο | CH(Me) | 0 | 0 | 'C^-5 | Cl | F | CH | |
66 | ω / Η. -ζ >ο | CH(Me) | O | O | O O-^ •^4 | Cl | F | CH | |
67 | ω , κ -Ζ >Ο | CH(Me) | 0 | o | Cl | F | CH | ||
68 | (Λ / -ζΗο | CH(Me) | O | o | Cl | F | CH | ||
69 | ο s^bi^o 1 | CH(F) | O | o | OMe | Cl | F | CH |
70 | ' en | CH(F) | O | o | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.75 (s, 1H), 8.08 (d, J= 7.5Hz, 1H), 7.95 (d, J = 9.5Hz, 1H), 6.49 (d, J= 56.5 Hz, 1 H), 4.30-4.28 (tn, 2H), 3.64 (s, 6H), 1.27-1.25 (m, 3H). |
71 | ' en | CH(C1) | o | o | OMe | Cl | F | CH | |
72 | ω / -ζ >ο <Η | CH(Et) | o | o | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 8.03 (d, .7= 7.5 Hz, 1H), 7.89 (d, J =9.5 Hz, 1H), 4.76 (t, .7= 6.5 Hz, 1H), 3.71 (s, 3H), 3.64 (s, 6H), 1.94-1.79 (m, 2H), 0.98 (t, J =7.5 Hz,3H). |
73 | ο S^N^O 1 | CH | o | o | OMe | Cl | F | CH | |
74 | ω / Η. -ζ >ο <Η | CH | o | o | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 8.03 (d, .7=7.5 Hz, 1 H), 7.89 (d, J = 9.5 Hz, 1 H), 4.75 (t,-7= 6.5 Hz, 1 H), 4.254.09 (m, 2H), 3.64 (s, 6H), 1.84-1.78 (m, 2H), 1.48-1.42 (m, 2H), 1.21 (t, J =5.5 Hz, 3H), 0.94 (t, J =7.5 Hz, 3H). |
75 | ω / κ. -ζ >0 | ^CH | o | o | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.54 (s, 1H), 8.03 (d, .7=7.5 Hz, 1H), 7.90 (d, .7=9.5 Hz, 1 H), 4.58 (d, .7= 5.5 Hz, 1H), 3.71 (s, 3H), 3.64 (s, 6H), 2.19-2.14 (m, 1H), 1.00 (d, J =6.5 Hz, 6H). |
76 | J-f ' en | Y CH | o | o | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.54 (s, 1H), 7.99 (d,J= 7.5 Hz, 1H), 7.89 (d, .7=9.5 Hz, 1H), 4.27-4.19 (m, 1H), 4.18-4.12 (m, 2H), 3.63 (s, |
611), 1.25 - 1.18 (m, 4H), 0.68 0.63 (m,2H), 0.55-0.52 (m, 2H). | |||||||||
77 | w 7 ω | CH(CFj) | O | O | OMe | Cl | F | CH | |
78 | ω / -Z >o □H | CH | O | O | OMe | Cl | F | CH | |
79 | O S^N^O 1 | ς CH | O | O | OEt | Cl | F | CH | Ή NMR (500 MHz, DMSO) 8 8.60 (s, 1H), 8.05 (d, 7= 7.5 Hz, 1H), 7.91 (d, 7= 9.5 Hz, 1 H), 5.67 (s, 1H), 4.20 (q, J =7.0 Hz, 2H), 3.833.78 (m, 1 H), 3.76 - 3.70 (m, 1H), 3.64 (s, 6H), 1.25-2.16 (m, 6H). |
80 | ω , -Z >O | 1 °^l CH | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.56 (s, 1H), 8.04 (d,7= 7.5 Hz, 1H), 7.90 (d, 7=9.5 Hz, 1H), 5.06-4.99 (m, 1H), 3.83-3.80 (m, 2H), 3.71 (s, 3H), 3.64 (s, 6H), 3.35 (s, 3H). |
81 | H» | CH(COOMe) | O | O | OMe | Cl | F | CH | |
82 | ω / K -Z >o | CH(Ph) | O | O | OMe | Cl | F | CH | |
83 | °1k“ 7 U) | CH(Me) | O | O | OMe | Br | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.46 (s, 1H), 8.03 (d, 7= 9.5 Hz, 1H), 7.99 (d, J= 8.0 Hz, 1H), 4.90 (q, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 3.65 -3.62 (m, 6H), 1.48 (d, 7= 7.0 Hz, 3H). |
84 | ω / -Z >O | CH(Me) | O | O | OEt | Br | F | CH | ‘H NMR (500 MHz, DMSO-7È) δ 8.46 (s, 1H), 8.03 (d, 7= 9.0 Hz, 1H), 7.99 (d, 7=7.5 Hz, 1 H), 4.86 (q, 7= 7.0 Hz, 1 H), 4.23- |
4.09 (m, 2H), 3.64 (s, 6H), 1.47 (d, J =7.0 Hz,3H), 1.21 (t, 7=7.0 Hz,3H). | |||||||||
85 | ω / Η. -ζ >° | CH(Me) | O | 0 | OMe | CFj | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.45 (s, 1H), 8.21 (d, 7=7.0 Hz, 1H), 8.11 (d, J =9.5 Hz, 1H), 4.94 (q, J =7.0 Hz, 1H), 3.70 (s, 3H), 3.64 (s, 6H), 1.48(d,7= 7.0 Hz, 3H). |
86 | ο s^rji^o | CH(Me) | O | O | OEt | CF, | F | CH | Ή NMR (500 MHz, DMSO-î/ê) δ 8.45 (s, 1H), 8.21 (d, 7=7.0 Hz, 1H), 8.10 (d, J= 10.0 Hz, 1H), 4.90 (q, J =7.0 Hz, 1 H), 4.22 — 4.10 (m,2H), 3.65 (s, 6H), 1.48 (d, 7= 7.0 Hz, 3H), 1.20 (t, 7=7.0 Hz, 3H). |
87 | ω / Η. -ζ >ο | CH(Me) | O | 0 | OMe | CN | F | CH | ‘H NMR (500 MHz, DMSO-J6) δ 8.48 (s, 1H), 8.29 (d, 7= 9.5 Hz, 1H), 8.13 (d, 7=7.0 Hz, 1H), 4.94 (q, 7 =7.0 Hz, 1H), 3.71 (s, 3H), 3.65 -3.63 (m, 6H), 1.50 (d, 7= 7.0 Hz, 3H). |
88 | °5^· ' (Λ | CH(Me) | 0 | O | OEt | CN | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.48 (s, 1H), 8.28 (d, 7= 9.5 Hz, 1H), 8.13 (d, 7=7.0 Hz, 1H), 4.91 (q, 7=7.0 Hz, 1H), 4.23 — 4.12 (m, 2H), 3.64 (s, 6H), 1.50 (d, 7= 7.0 Hz, 3 H), 1.21 (t, 7=7.0 Hz,3H). |
89 | C0 / Η -ζ >Ο | CH(Me) | O | O | OEt | Cl | F | N | |
90 | » ) ΛοΚ | CH(Me) | O | O | OEt | Cl | F | CH | |
91 | 1 θ Αλα S^N^O | CH(Me) | O | O | OEt | Cl | F | CH |
92 | CO τH -Z >o | CH(Me) | O | O | OEt | Cl | F | CH | |
93 | 1 ° S^N^O 1 | CH(Me) | O | O | OEt | Cl | F | CH | |
94 | 0 A^N^lA S^N^O 1 | CH(Me) | O | O | OEt | Cl | F | CH | |
95 | JT ^-r ' V) | CH(Me) | O | O | OEt | Cl | F | CH | |
96 | A ° ^^''rA'tA S^N^O λ | CH(Me) | O | O | OEt | Cl | F | CH | |
97 | O TA* s^bi^o ch2f | CH(Me) | O | O | OEt | Cl | F | CH | |
98 | 0 H2%An\ S^N^O 1 | CH(Me) | O | O | OEt | Cl | F | CH | |
99 | J$A AT ü ω z | CH(Me) | O | O | OEt | Cl | F | CH | |
100 | ω To T -Z >O □T | CH(Me) | O | O | OEt | Cl | F | CH | |
101 | J*a AT° —Ο ω | CH(Me) | O | O | OEt | Cl | F | CH | |
102 | ω ω— -Z >O | CH(Me) | O | O | OEt | Cl | F | CH | |
103 | I 0 ü Άό^ν^ν^ sAnA0 1 | CH(Me) | O | O | OEt | Cl | F | CH |
104 | °=( <Λ ZI Ή' -Z >o | CH(Me) | O | O | OEt | Cl | F | CH | |
105 | ô ô ην^''νχ^'γΑ I X X S^ O 1 | CH(Me) | O | O | OEt | Cl | F | CH | |
106 | I Ni Z M ω zi H -Z >o oX | CH(Me) | O | O | OEt | Cl | F | CH | |
107 | O MeO2S.NXN.\ S^N^O | CH(Me) | O | O | OEt | Cl | F | CH | |
108 | ω -vX>o oX i | CH(Me) | O | O | OEt | Cl | F | CH | |
109 | ô >Α,λ S^N^O | CH(Me) | O | O | OEt | Cl | F | CH | |
110 | °\ en ) -Z >o cH | CH(Me) | O | O | OEt | Cl | F | CH | |
111 | ô S^X^O O^J OH | CH(Me) | O | O | OEt | Cl | F | CH | |
112 | M Z~\ z4 X° 1 ω o | CH(Me) | O | O | OEt | Cl | F | CH | |
113 | X -< w P o=< _o | CH(Me) | O | O | OEt | Cl | F | CH | |
114 | ''N' O S^N^O | CH(Me) | O | O | OEt | Cl | F | CH |
115 | 1 0 S^nXd 1 | CH(Me) | O | o | OEt | Cl | F | CH | |
116 | ô HN^N^ S^nXd Ph | CH(Me) | O | o | OEt | CI | F | CH | |
117 | Cl Ck Λ Λ Tjl ? v S^nX) 1 | CH(Me) | O | o | OEt | Cl | F | CH | |
118 | ω / O | CH(Me) | o | o | OEt | Cl | F | CH | |
119 | r-\ θ ο I ü s, ΐΆ S^N^O 1 | CH(Me) | o | o | OEt | Cl | F | CH | |
120 | 5^‘ o.—J <n | CH(Me) | o | o | OEt | Cl | F | CH | |
121 | ô Μθ°'γχΐϊγχ^Ν^Ν?!ί | CH(Me) | o | 0 | OEt | CI | F | CH | |
122 | s° Xo | CH(Me) | o | o | OEt | Cl | F | CH | |
123 | s cXnX) 1 | CH(Me) | o | o | OEt | Cl | F | CH | |
124 | ω / >-< -Z >o (Λ | CH(Me) | o | 0 | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.51 (s, 1H), 8.00 (d,J= 7.5 Hz, 1H), 7.88 (d, J=9.0Hz, 1H), 4.89 (q,J= 7.0 Hz, 1H), 4.14 (s, 3H), 3.70 (s, 3H), 3.62 (s, 3H), 1.47 (d, J= 7.0 Hz, 3H). |
125 | 0 S^hXs 1 | CH(Me) | o | s | OMe | Cl | F | CH |
126 | o=< z— /2¼ > tn | CH(Me) | O | O | OEt | Cl | F | CH | |
127 | ω > H. -Z >0 ω | CH(Me) | O | s | OEt | Cl | F | CH | |
128 | I ,w JH H z/z”^ / ω | CH(Me) | O | O | 7-o^ | Cl | F | CH | |
129 | ω / K -Z >0 ω | CH(Me) | O | O | Cl | F | CH | ||
130 | ω / >-< -Z >0 | CH(Me) | O | 0 | Ao | Cl | F | CH | |
131 | ω / H. -Z >o ω | CH(Me) | 0 | O | 0^ | Cl | F | CH | |
132 | •s P M /z~ /2¼ / ω | CH(Me) | 0 | O | Ao | Cl | F | CH | |
133 | 0 'N^rA S^N^S 1 | CH(Me) | O | O | ho ^0 \ | Cl | F | CH | |
134 | ω / Kz —Z )=o AA ω hv | CH(Me) | O | O | /-o 0— | Cl | F | CH | |
135 | /w □=< z/2A ' en | CH(Me) | 0 | O | Λο °Λ | Cl | F | CH | |
136 | u> / K -Z >o ω r^v | CH(Me) | O | O | /'Ο \ | Cl | F | CH | |
• 137 | ω / _Z^>O | CH(Me) | O | O | 0 | Cl | F | CH | |
138 | 0 'Ν'^ίΑ S^N^S 1 | CH(Me) | O | O | 0 | Cl | F | CH |
139 | ü ^ν^γΑ S^N^S | CH(Me) | o | 0 | Ao 9 X ΛοΛο | Cl | F | CH | |
140 | ω / -Ho | CH(Me) | o | o | Ao | Cl | F | CH | |
141 | ü '''hVhA S^N^S 1 | CH(Me) | o | o | Ao \^,o^ | Cl | F | CH | |
142 | ü '''hVrA S^N^S | CH(Me) | o | o | Ao ^^0 | Cl | F | CH | |
143 | 0=< Z— /H ' V) | CH(Me) | o | o | A° \ 'O | Cl | F | CH | |
144 | U> / -Z >o A2^ ω | CH(Me) | o | o | Λ° 1 Z Aa | Cl | F | CH | |
145 | ω / H —Z )=o Aa ω X | CH(Me) | o | 0 | Ao VA | Cl | F | CH | |
146 | ω / >-< -Z >0 ω | CH(Me) | o | o | /'O | Cl | F | CH | |
147 | \ 1 ω / H —Z )=o A=> ω r'V | CH(F) | o | o | OMe | Cl | F | CH | |
148 | ω / >-< -Z >0 A^ u> | CH(F) | o | o | OEt | Cl | F | CH | |
149 | 0 '^Ν'^γΑ S^N^S 1 | CH(C1) | o | o | OMe | Cl | F | CH | |
150 | ω / A< -Z >C A^r ω <>< | CH(Et) | o | o | OMe | Cl | F | CH | |
151 | ω / H -Z >o ω r>< | CH | o | o | OMe | Cl | F | CH |
152 | ω / —ζ )=ο ω | CH | O | O | OEt | Cl | F | CH | |
153 | ω / κ —Ζ >=Ο ω | ^CH | O | O | OMe | Cl | F | CH | |
154 | ϋ ^ν^ιΑ S^N^S | Y CH | O | O | OEt | Cl | F | CH | |
155 | ω / >-< -ζ >ο ω | CH(CF3) | O | O | OMe | Cl | F | CH | |
156 | 0 ^N^hA S^N^S 1 | ς CH | O | O | OMe | Cl | F | CH | |
157 | ω / -ζ >ο ω | ς CH | O | O | OEt | Cl | F | CH | |
158 | Α-< ' <η | 1 CH | O | O | OMe | Cl | F | CH | |
159 | ω / >-< —ζ >=ο ω | CH(COOMe) | O | O | OMe | Cl | F | CH | |
160 | 0 N^tA S^N^S 1 | CH(Ph) | O | O | OMe | Cl | F | CH | |
161 | ω / -ζ >ο Α^τ ω | CH(Me) | 0 | O | OEt | Br | F | CH | ‘H NMR (500 MHz, DMSO-dô) δ 8.45 (s, 1H), 8.01 (d,J=9.0 Hz, 1H), 7.97 (d, J =7.5 Hz, 1H), 4.87-4.85 (m, 1H), 4.29-4.00 (m, 5H), 3.62 (s, 3H), 1.47 (d, J= 7.0 Hz, 3H), 1.20 (t, .7= 7.0 Hz, 3H). |
162 | ω / Α< -ζ >ο Α=> | CH(Me) | O | O | OEt | CFj | F | CH |
163 | 0=< Z— ' tf) | CH(Me) | O | O | OEt | CN | F | CH | |
164 | O=\ Z— | CH(Me) | O | O | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.51 (s, 1H), 7.95 (d, J =7.5 Hz, 1H), 7.88 (d, J = 9.5Hz, 1H), 4.90 (q, J =7.0 Hz, 1H), 3.70 (s, 3H), 3.40 (s, 3H), 2.59 (s, 3H), 1.47(d,7= 7.0 Hz, 3H). |
165 | -Z >o | CH(Me) | O | O | OEt | Cl | F | CH | |
166 | s 'N^A S^N^S 1 | CH(Me) | 0 | O | OEt | Cl | F | CH | |
167 | o n^A S^N^O | CH(Me) | O | O | SMe | Cl | F | CH | |
168 | ω / A -Z >o | CH(Me) | O | O | SEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-ds) δ 8.58 (s, 1H), 8.06 (d, 7= 8.0 Hz, 1 H), 7.91 (d, 7=9.5 Hz, 1 H), 4.94 (q, 7= 7.0 Hz, 1H), 3.63 (s, 6H), 2.89-2.83 (m,2H), 1.46 (d, 7= 7.0 Hz, 3H), 1.18 (t,7= 7.5 Hz,3H). |
169 | °1a 7 ω | CH(Me) | O | O | As | Cl | F | CH | |
170 | ω / A -z >0 fa | CH(Me) | O | O | Cl | F | CH | ||
171 | ω / A -Z >o fa | CH(Me) | O | O | Cl | F | CH | ||
172 | O S^N^O | CH(Me) | 0 | O | / <° cA | Cl | F | CH |
173 | ' U) | CH(Me) | O | O | /S \ | Cl | F | CH | |
174 | ω / H -z >O | CH(Me) | O | O | As °„k | Cl | F | CH | |
175 | M | CH(Me) | 0 | O | <□ J •4, | Cl | F | CH | |
176 | O 'Ν'^Γ'Λ S^N^O 1 | CH(Me) | O | O | As | Cl | F | CH | |
177 | 1 ω / H. -Z >O | CH(Me) | O | O | As V/=N V? | Cl | F | CH | |
178 | ω / >< -Z >o | CH(Me) | O | O | SEt | CN | F | CH | |
179 | ω / H. —Z >=O ω | CH(Me) | O | O | SMe | Cl | F | CH | |
180 | ü S^N^S 1 | CH(Me) | O | O | SEt | Cl | F | CH | |
181 | ω , H -z >0 | CH(Me) | O | O | NHEt | Cl | F | CH | |
182 | ω z H. -Z >o | CH(Me) | O | O | b~NH \ | Cl | F | CH | |
183 | ^A° ' ω | CH(Me) | O | O | / / ° -|-NH | Cl | F | CH | Ή NMR(500 MHz, DMSO-rfs) δ 11.82 (s, 1H), 8.34 (s, 1H), 8.08 (d,J= 8.0 Ha 1H), 7.83 (d, J=9.5Hz,lH), 4.50 (q,J= 6.5 Ha 1H), 3.64 (s, 6H), 3.62 (s, 3H), 3.35-3.28 (m, 2H), 2.532.49 (m, 2H), 1.66 (d,J= 6.5 Ha3H). |
184 | ω , -Ho | CH(Me) | O | O | /N H | Cl | F | CH | |
185 | ω / Η -ζ >0 □Η- | CH(Me) | O | O | AnH | Cl | F | CH | |
186 | Ô S^N^O 1 | CH(Me) | O | O | T '/ 1 / o | Cl | F | CH | |
187 | Η ' <η | CH(Me) | O | O | /~NH >O. °zN Λ | CN | F | CH | |
188 | (Λ / Η. —ζ >=ο ω i ί | CH(Me) | O | O | /-NH Λ/ °/N A | Cl | F | CH | |
189 | ω / Η. -ζ >ο □Η- | C(Me)2 | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.46 (s, 1H), 8.00 (d, 7= 7.5 Hz, 1H), 7.89 (d, 7= 9.5 Hz, 1H), 3.68 (s, 3H), 3.64 (s, 6H), 1.54 (s, 6H). |
190 | ω / Η_ -ζ >ο οΗ- | C(F)2 | O | O | OMe | Cl | F | CH | |
191 | ω / -ζ >ο AAω r'V | C(Me)2 | O | O | OMe | CI | F | CH | |
192 | ω / Η -ζ >ο ω ζν | C(F)2 | O | O | OMe | Cl | F | CH | |
193 | Η ο=( Ζ— ο d? | CH(Me) | O | O | OH | Cl | F | CH | 1H NMR (500 MHz, DMSO) δ 12.89 (s, 1H), 8.49 (s, 1H), 7.92-7.90 (m, 2H), 6.60 (s, 1 H), 4.76 (q, J = 7.0 Hz, 1H), 3.42 (s, 3 H), 1.46 (d, J = 7.0Hz,3H). |
194 | ω1 Ο —Ζ \=ο | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.93 (d, 7 =7.5 Hz, 1H), 7.88 (d, 7= 9.5 Hz, 1H), 6.61 (s, 1H), 4.89-4.87 (m, 1H), 3.70 (s, |
3H), 3.43 (s, 3H), 1.48 (d, 7= 7.0 Hz, 3H). | |||||||||
195 | Μ5 O=< Z— O d? | CH(Me) | 0 | s | OMe | Cl | F | CH | |
196 | J1 O —Z \=o | CH(Me) | 0 | O | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 7.94-7.85 (m, 2H), 6.61 (s, 1 H), 4.86 (q, 7= 7.0 Hz, 1 H), 4.16 (q, 7 =7.0 Hz, 2H), 3.42 (s, 3H), 1.47 (d, 7= 7.0Hz,3H), 1.20 (d,7=7.0 Hz, 3H). |
197 | O —Z /=O | CH(Me) | O | s | OEt | Cl | F | CH | |
198 | 0 rV f3c^n^o | CH(Me) | O | 0 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 7.95-7.83 (m, 2H), 6.61 (s, 1 H), 4.88 (q, 7= 7.0Hz, 1H), 4.17 - 3.98 (m, 2H), 3.43 (s, 3H), 1.63-1.56 (m, 2H), 1.48 (d, 7= 7.0 Hz, 3H), 0.87 (t,7=7.0Hz, 3H). | |
199 | ω1 • O —Z )=O | CH(Me) | O | O | cA | Cl | F | CH | 1H NMR (500 MHz, Chloroform-d) δ 8.55 (s, 1 H), 7.84 (d, J = 7.5 Hz, 1H), 7.35 (d, J = 8.5 Hz, 1H), 6.41 (s, 1H), 5.13-5.10 (m, 1 H), 4.79-4.76 (m, 1 H),3.60 (s, 3H), 1.53 (d, J = 7.0 Hz, 3H), 1.36 -1.24 (m, 6H). |
200 | <? O —Z /=O | CH(Me) | O | O | ^θχ/ΧΖ | Cl | F | CH | ‘H NMR (500 MHz, DMSO-d6) δ 8.52 (s, 1 H), 7.91 (d, J = 8.0 Hz, 1H), 7.88 (d, J = 9.0 Hz, 1H), 6.61 (s, 1H), 4.87 (q, J = 7.0 Hz, 1 H), 4.18- 4.05 (m, 1H), 3.42 (s, 3H), 1.59- 1.53 (m, 2H), 1.47 (d, J = 7.0Hz,3H), 1.35 -1.25(m, 3H), 0.84 (t, J = 7.5 |
Hz,3H) | |||||||||
201 | A° Z— O Ll? | CH(Me) | O | O | Cl | F | CH | Ή NMR (500 MHz, DMS0-<4) δ 8.52 (s, 1H), 7.92 - 7.90 (m, 1H), 7.87 (d, J= 9.5 Hz, 1 H), 6.60 (s, 1H), 4.89 (q, 7=7.0 Hz, 1H), 3.98-3.95 (m, 1H), 3.88-3.84 (m, 1H), 3.42 (s, 3H), 1.91-1.86 (m, 1H), 1.49 (d, J=7.0 Hz, 3H), 0.93-0.81 (m, 6H). | |
202 | A° o=< z— O LL | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.50 (s, 1H), 7.90-7.89 (m, 2H), 6.61 (s, 1 H), 4.72-4.71 (m, 1H), 3.42 (s, 3H), 1.45-1.37 (m, 12H). | |
203 | A O=< Z— O LL? | CH(Me) | O | 0 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfj) δ 8.52 (s, 1H), 7.91-7.87 (m, 2H), 6.61 (s, 1 H), 4.89-4.84 (m, 1H),4.17 — 4.04 (m, 2H), 3.42 (s, 3H), 1.58-1.55 (m, 2H), 1.47 (d, J= 7.0 Hz, 3H), 1.27-1.23 (m, 4H), 0.85-0.79 (m, 3H). | |
204 | J1 O —Z )=O oA | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-</6) δ 8.50 (s, 1 H), 7.89 (d,J= 8.0 Hz, 1H), 7.86 (d, J =9.5 Hz, 1H), 6.58 (s, 1H), 4.88-4.81 (m, 1H), 3.41 (s, 3H), 3.38-3.36 (m,2H), 1.57 — 1.51 (m, 2H), 1.45 (d, 7=7.0 Hz,3H), 1.42- 1.37 (m,2H), 1.22-1.18 (m, 2H), 0.86 (t, J= 7.0 Hz, 3H). | |
205 | <? O —Z Ao fa | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.51 (s, 1H), 7.92-7.86 (m, 2H), 6.60 (s, 1H), 4.89 -4.84 (m, 1H), 4.17-4.04 (m, 2H), 3.43 (s, 3H), 1.59-1.53 (m, 2H), 1.47 (d, 7= 7.0 Hz, 3H), 1.26-1.19 (m, |
8H), 0.84 (ζ J= 7.0 Hz, 3H). | |||||||||
206 | Ο iV f3ct'n''Ad | CH(Me) | O | O | CI | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.51 (s, 1H), 7.96-7.83 (m, 2H), 6.60 (s, 1 H), 4.88-4.86 (m, 1 H), 4.21- 4.11 (m,3H), 3.42 (s, 3H), 1.47 (d,J= 7.0 Hz, 3H), 1.24-1.22 (m, 14H). | |
207 | J1 o —Z \=o | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.51 (s, 1H), 7.90-7.88 (m, 2H), 6.60 (s, 1H), 4.86 (m, 2H), 3.42 (s, 3H), 1.46 (d, J= 7.0 Hz, 3 H), 1.17 -1.06(m, 13H), 0.84-0.82 (m, 3H). | |
208 | O=< Z— o IL· | CH(Me) | O | 0 | Cl | F | CH | 1H NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 7.98-7.86 (m, 2H), 6.62 (s, 1H), 5.92-5.90 (m, 1H), 5.28-5.26 (m, 2 H), 4.93-4.91 (m, 1H), 4.68-4.66 (m, 2H), 3.42 (s, 3H), 1.49 (d, J = 7.0 Hz, 3H). | |
209 | J1 o —Z /=O fa | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfs) δ 8.49 (s, 1H), 8.00-7.84 (m, 2H), 6.59 (s, 1H), 5.77-5.68 (m, 1H), 5.08-5.02 (m, 1H), 5.00-4.97 (m, 1H), 4.86-^1.80 (m, 1H), 4.23-4.08 (m, 2H), 3.40 (s, 3H), 2.35-2.31 (m, 2H), 1.44 (d, 7=7.0 Hz, 3 H). | |
210 | fa oY z— u d? | CH(Me) | O | 0 | Cl | F | CH | ||
211 | O=/ Z— U if? | CH(Me) | O | 0 | Cl | F | CH |
212 | JA o=< z— O LL | CH(Me) | O | O | A o | Cl | F | CH | 1H NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 7.97-7.84 (m, 2H), 6.61 (s, 1H), 4.98-4.89 (m, 1 H), 4.81 (s, 2H), 3.60-3.56 (m, 1H), 3.42 (s, 3H), 1.49 (d, J = 7.0 Hz, 3H). |
213 | A0 O=< Z— O LL | CH(Me) | O | O | cA E | Cl | F | CH | |
214 | J1 O —z \=o □A | CH(Me) | O | O | Cl | F | CH | 1H NMR (500 MHz, DMSO-d6) δ 8.51 (s, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.88 (d, 3 = 9.0 Hz, 1H), 6.61 (s, 1H), 5.16 (d, 3 = 6.5 Hz, 1H), 4.82 (q, 3 = 7.0 Hz, 1H), 3.42 (s, 3H), 1.88- 1.77 (m, 2H), 1.68-1.49 (m, 6H), 1.45 (d, 3 = 7.0 Hz, 3H). | |
215 | J1 O —z \=o oA | CH(Me) | O | O | Ao | Cl | F | CH | |
216 | O —Z /=O oA | CH(Me) | O | O | /o^F | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 7.92 (d, 7=7.5 Hz, 1H), 7.88 (d, 7=9.5 Hz, 1 H), 6.61 (s, 1H), 4.93 (q, 7= 6.5 Hz, 1 H), 4.684.58 (m, 2H), 4.42 — 4.34 (m, 2H), 3.42 (s, 3H), 1.50 (d, 7= 7.0 Hz, 3H). |
217 | J1 O —z \=o oA | CH(Me) | O | O | F v°af | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 7.94-7.82 (m, 2H), 6.61 (s, 1 H), 4.99-4.97 (m, 1H), 4.47-4.45 (m, 2H), 3.44-3.42 (m,4H), 1.50 (d, 7= 7.0 Hz, 3H). |
218 | O A Fjc iAo | CH(Me) | O | O | X°-cf3 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-ds) δ 8.51 (s, 1H), 7.92-7.87 (m, 2H), 6.61 (s, 1H), 5.11-4.68 (m, 3H), 3.42 (s, 3H), 1.45 (d, 7= 7.0 Hz, 3H). |
219 | <7 Ο —ζ \=ο ο>-ΖΛ | CH(Me) | O | o | /-O | Cl | F | CH | |
220 | 0 f3cxn^o | CH(Me) | 0 | o | V | Cl | F | CH | ‘H NMR (500 MHz, DMSO-<4) δ 8.55 (s, 1H), 7.93-7.87 (m, 2H), 6.62 (s, 1 H), 4.99 (q, 7= 7.0 Hz, 1H), 4.54 -4.35 (m, 2H), 3.42 (s, 3H), 1.69-1.59 (m, 3H), 1.51 (d, 7= 7.0 Hz, 3H). |
221 | οχ ζ— ο IL· | CH(Me) | O | o | LL· o | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfi) δ 8.51 (s, 1H), 7.94 - 7.85 (m, 2H), 6.62 (s, 1H), 4.89 (q, 7= 7.0 Hz, 1H), 4.42 -4.27 (m, 2H), 3.42 (s, 3H), 2.77-2.65 (m, 2H), 1.47 (d, 7= 7.0 Hz, 3H). |
222 | J1 ο —ζ \=ο | CH(Me) | O | o | A Tl | Cl | F | CH | |
223 | οχ ζ— ο LL | CH(Me) | O | o | /'O '''CF3 | Cl | F | CH | |
224 | οχ ζ— ο IL· | CH(Me) | O | o | o | Cl | F | CH | |
225 | 1 κ οχ ζ— ο IX? | CH(Me) | O | o | Cl | F | CH | ‘H NMR (500 MHz, DMSO-7s) δ 8.52 (s, 1H), 7.92 (d, 7= 8.0Hz, 1 H), 7.88 (d, 7= 9.5 Hz, 1H), 6.62 (s, 1H), 6.58-6.52 (m, 1H), 6.13-6.06 (m, 1H), 4.96-4.87 (m, 1 H), 4.874.73 (m, 2H), 3.43 (s, 3H), 1.48 (d, 7= 7.0 Hz, 3H). | |
226 | ω1 Ο —Ζ )=ο | CH(Me) | O | o | Cl | F | CH | ‘H NMR (500 MHz, DMSO-A) δ 8.53 (s, 1 H), 7.91-7.85 (m, 2H), 6.59 (s, 1H), 5.09 (s, 2H), 5.02-4.99 (m, 1H), 3.40 (s, 3H), 1.49 (d, 7= 7.0 Hz, 3H). |
227 | J1 Ο —Ζ )=Ο ο | CH(Me) | O | O | \°^^CN | Cl | F | CH | ‘H NMR (500 MHz, DMSO-i/t) δ 8.53 (s, 1H), 7.93 (d, 7= 8.0, 1H), 7.88 (d, 7= 9.5 Hz, 1H), 6.61 (s, 1H), 4.93 (q, 7=7.0 Hz, 1H), 4.36-4.26 (m, 2H), 3.42 (s, 3H), 2.94-2.90 (m,2H), 1.50 (d, 7=7.0 Hz, 3H). |
228 | ο=< ζ— ο ιΓ | CH(Me) | O | O | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.95-7.86 (m, 2H), 6.61 (s, 1H), 4.87-4.85 (m, 1H), 4.14-4.12 (m, 2H), 3.60-3.58 (m, 2H), 3.42 (s, 3H), 1.49 (d, 7= 7.0 Hz, 3H). | |
229 | ο=ς ζ— ο LL | CH(Me) | O | O | ho ^~~O \ | Cl | F | CH | |
230 | ο=< ζ— ο d? | CH(Me) | O | O | ho o-^ | Cl | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 7.92 (d, 7= 8.0 Hz, 1 H), 7.88 (d, 7=9.5 Hz, 1 H), 6.61 (s, 1H), 4.93-4.86 (m, 1H), 4.32-4.15 (m, 2H), 3.55 3.51 (m,2H), 3.42 (s, 3H), 3.23 (s, 3H), 1.48 (d, 7= 7.0 Hz, 3H). |
231 | <Τ ο —ζ \=ο | CH(Me) | O | O | /O °Λ | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.50 (s, 1H), 7.92-7.84 (tn, 2H), 6.59 (s, 1H), 4.89-4.85 (m, 1 H), 4.28- 4.24 (m, 1H), 4.18-4.15 (m, 1H), 3.55-3.53 (m,2H), 3.42 — 3.38 (m, 5H), 1.46 (d, 7= 7.0 Hz, 3H), 1.03 (ζ 7= 7.0 Hz, 3H). |
232 | ω1 Ο —Ζ )=ο | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfs) δ 8.51 (s, 1H), 7.92 (d, 7= 8.0 Hz, 1H), 7.88 (d, 7=9.5 Hz, 1H), 6.60 (s, 1H), 4.88 (q, 7= 7.5 Hz, 1 H), 4.334.12 (m,2H), 3.59 -3.52 (m, 2H), 3.42 (s, |
3H), 3.36 -3.33 (m, 2H), 1.47 (d, J =7.0 Hz,3H), 1.45-1.38 (m, 2H), 1.34-1.22 (m, 2H), 0.85 (t, J=7.5 Hz, 3H). | |||||||||
233 | J*A° o=< z— ü LL | CH(Me) | O | O | /'O \ | Cl | F | CH | Ή NMR (500 MHz, DMSO-</6) δ 8.53 (s, 1 H), 7.93 -7.87 (m, 2H), 6.61 (s, 1H), 5.33-5.30 (m, 1H), 5.24-5.21 (m, 1H), 4.94-4.91 (m, 1H), 3.42 (s, 3H), 2.15 (s, 3H), 1.49 (d,J= 7.0 Hz, 3H). |
234 | J1 O —z To oT | CH(Me) | O | 0 | Cl | F | CH | Ή NMR (500 MHz, DMSO-Jî) δ 8.52 (s, 1H), 7.92 (d, J =8.0 Hz, 1H), 7.88 (d, J = 9.5 Hz, 1 H), 6.61 (s, 1H), 5.00-4.83 (m, IH), 4.41-4.16 (m,2H), 3.43 (s, 3H), 2.74-2.71 (m, 2H), 2.08 (s, 3H), 1.49 (d,J= 7.0 Hz, 3H). | |
235 | O /a f3c n o | CH(Me) | O | O | \°Y O | Cl | F | CH | |
236 | T° O=< z— O IL | CH(Me) | O | O | O >° | Cl | F | CH | ‘H NMR (500 MHz, DMSO-d6) δ 8.49 (s, III), 7.95-7.87 (m, 2H), 6.61 (s, 1H), 4.76 (q, J= 7.0Hz, 111),3.95 (t,J= 7.0Hz, 2H), 3.43 (s, 3H), 1.65-1.55 (m, 2H), 1.46 (d, J =7.0 Hz,3H), 1.20 (t,J= 7.0 Hz, 3H). |
237 | ω1 O —z To oT | CH(Me) | O | 0 | 1 0 | Cl | F | CH | |
238 | J1 Ω —z To oT | CH(Me) | O | O | 0 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-A) δ 8.53 (s, 1 H), 7.94 (d,J= 8.0 Hz, 1H), 7.88 (d, J=9.5Hz, 1H), 6.62 (s, 1H), 5.01-4.79(m, 3H), 3.42 (s, 3H), 2.09 (s, 3H), 1.54 (d,J= 7.0 Hz, 3H). |
239 | J Ο —Z \=o oX | CH(Me) | O | O | 0 | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 7.95 (d, .7=7.5 Hz, 1H), 7.88 (d, J=9.5Hz,lH), 6.62 (s, 1H), 5.01 (q, 7=7.0 Hz, 1H), 4.80 (s, 2H), 4.19-4.09 (m,2H), 3.43 (s, 3H), 1.53 (d, 7= 7.0 Hz, 3H), 1.19 (t, 7 =7.0 Hz, 3H). |
240 | O=< Z— ω VL· | CH(Me) | O | 0 | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-ds) δ 8.48 (s, 1H), 7.90 (d, 7= 8.0 Hz, 1H), 7.86 (d, 7=9.5 Hz, 1H), 6.59 (s, 1H), 4.89 - 4.79 (m, 1 H), 4.37-4.32 (m, 1H), 4.27-4.22 (m, 1H), 3.54 (s, 3H), 3.40 (s, 3H), 2.69-2.63 (m, 2H), 1.42 (d, 7= 7.0 Hz, 3H). |
241 | J1 O —Z \=o oX | CH(Me) | O | O | 0 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-t/i) δ 8.51 (s, 1H), 7.95-7.83 (m, 2H), 6.60 (s, 1H), 5.18-5.08 (m, 1 H), 4.96- 4.89 (m, 1H), 3.64 (s, 3H), 3.40 (s, 3H), 1.49 (t, 7= 7.0 Hz, 3H), 1.41 (t, 7= 7.5 Hz, 3H). |
242 | J1 O —Z \=o oX | CH(Me) | O | O | X O ) | Cl | F | CH | |
243 | O=< Z— O d? | CH(Me) | O | 0 | O | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.92-7.90 (m, 2H), 6.62 (s, 1H), 4.87-4.85 (m, 1 H), 3.60 (s, 3H), 3.42 (s, 3H), 1.52-1.42 (tn, 9H). |
244 | x° O=< Z— O d? | CH(Me) | O | O | LL “•-M ° | Cl | F | CH | |
245 | J1 O —Z Xo oX | CH(Me) | O | O | Xo °x Y- o °x \ | Cl | F | CH | ‘H NMR (500 MHz, DMSO-dé) δ 8.55 (s, 1H), 7.95-7.88(m, 2H), 6.62 (s, 1H), 6.03 (s, 1H), 5.02-4.97 |
(m, IH), 3.73 (s, 3H), 3.42- 3.40 (m, 6H), 1.54-1.52(m, 3H). | |||||||||
246 | o=< z— O LL? | CH(Me) | O | o | o °=< o | Cl | F | CH | IH NMR (500 MHz, DMSO) δ 8.53 (s, IH), 7.91-7.89 (m, 2H), 6.69 (s, IH), 6.61 -6.56(m, IH), 4.92-4.90 (m, 1 H), 4.10-4.08 (m, 2H), 3.42 (s, 3H), 1.52-1.40 (m, 6H), 1.20-1.18(01, 3H). |
247 | o=< z— o LL? | CH(Me) | O | o | Ao °u K ΛοΑο | Cl | F | CH | |
248 | J1 O —Z \=o o | CH(Me) | O | 0 | /-o N | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.55 (s, IH), 7.93 (d, .7=7.5, Hz, IH), 7.88 (d, J = 9.5 Hz, 1 H), 6.60 (s, IH), 5.01 (q, J =7.0 Hz, IH), 3.42 (s, 3H), 1.98 (s, 3H), 1.94 (s, 3H), 1.53 (d,J= 7.0 Hz, 3H). |
249 | o=< z— o LL? | CH(Me) | o | o | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.55 (s, 1 H), 7.93 (d, J =7.5 Hz, IH), 7.88 (d, .7=9.5 Hz, 1 H), 6.60 (s, IH), 5.01 (q, .7=7.0 Hz, IH), 3.42 (s, 3H), 2.35-2.30 (οι, 2H), 1.92 (s, 3H), 1.54 (d,J= 7.0 Hz, 3H), 1.07 (t, J =7.0 Hz, 3H). | |
250 | o=Ç z— o t£? | CH(Me) | o | o | / | Cl | F | CH | ‘H NMR (500 MHz, DMSO-<4) δ 8.55 (s, IH), 7.93 (d, J =8.0 Hz, IH), 7.89 (d, .7=9.5 Hz, 1 H), 6.60 (s, IH), 5.01 (q, .7=7.0 Hz, IH), 3.42 (s, 3H), 2.65-2.58 (m, IH), 1.89 (s, 3H), 1.54 (d,J= 7.0 Hz, 3H), 1.09 (d, J=7.0 Hz, 6H). |
251 | Ο îV f3c n^o | CH(Me) | O | 0 | ,VO.NX- | Cl | F | CH | ‘H NMR (500 MHz, DMSO-J6) δ 8.55 (s, 1H), 7.94 - 7.92 (m, lH),7.88(d, J= 9.5 Hz, 1H), 6.60 (s, 1H), 5.02 (q, J=7.0Hz,lH), 3.42 (s, 3H), 2.40-2.27 (m, 4H), 1.54 (d, 7= 7.0 Hz, 3H), 1.07 (t, 7=7.5 Hz, 3H), 0.98 (t, 7= 7.5 Hz, 3H). |
252 | jh° o=< z— O d? | CH(Me) | 0 | 0 | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.55 (s, 1 H), 7.94 (d,7= 7.5 Hz, IH), 7.88 (d, 7=9.5 Hz, 1H), 6.61 (s, 1H), 5.05-4.98 (m, 1H), 4.10 (q, J= 7.0 Hz, 2H), 3.42 (s,3H), 1.98 (s, 3H), 1.54 (d,7= 7.0Hz,3H), 1.27 (1,7=7.0 Hz, 3H). | |
253 | o=< Z— O LL? | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.56 (s, 1H), 7.93 (d, 7= 6.0 Hz, 1H), 7.89 (d, J=9.0 Hz, 1H), 6.61 (s, 1H), 5.01 (q,7=7.0 Hz, 1 H), 4.05 (s, 2H), 3.42 (s, 3H), 3.27 (s, 3H), 1.95 (s, 3H), 1.55 (d, 7= 7.5 Hz, 3H). | |
254 | <? O —z \=o oV | CH(Me) | O | O | V°'N^CO2Et | CI | F | CH | ‘H NMR (500 MHz, DMSO-rfi) δ 8.58 (s, 1H), 7.93-7.88 (m, 2H), 6.61 (s, 1H), 5.13 (q, 7= 7.0 Hz, 1 H), 4.28 (q, 7= 7.0 Hz, 2H), 3.42 (s, 3H), 2.15 (s, 3H), 1.58 (d, 7= 7.0 Hz, 3H), 1.28 (t, 7= 7.0 Hz, 3H). |
255 | K o=/ z— O d? | CH(Me) | O | O | P / | Cl | F | CH | ‘H NMR (500 MHz, DMSO-<4) δ 8.78 (s, 1H), 8.57 (s, 1 H), 7.95 (d, 7= 8.0 Hz, 1H), 7.89 (d, 7= 9.5 Hz, 1 H), 7.78 (d, J=7.5 Hz, 2H), 7.60 7.50 (m, 3H), 6.59 (s, 1H), 5.09 (q, 7= 7.0 Hz, 1H), 3.40 (s, 3H), 1.59 (d,7= |
7.0 Hz, 3H). | |||||||||
256 | ω1 Ο —Ζ \=ο | CH(Me) | O | o | a-o | CI | F | CH | |
257 | A ο=< ζ— ο ιΓ | CH(Me) | O | o | /-q ¢23 o | Cl | F | CH | |
258 | ω1 Ο —Ζ )=ο ί | CH(Me) | O | o | /'O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.54 (s, 1H), 7.93 (d, 7= 7.5, Hz, IH), 7.89 (d, 7=9.5 Hz, 1H), 6.60 (s, 1 H), 4.98 (q, 7 =7.0 Hz, 1H), 3.42 (s, 3H), 2.49-2.42 (m,4H), 2.31 — 2.21 (m,4H), 1.53 (d, 7= 7.0 Hz,3H). |
259 | ο ο=< ζ— ο ί | CH(Me) | 0 | o | ’b o \ Z Λ | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 7.92 (d, 7= 8.0 Hz, 1H), 7.88 (d, 7=9.5 Ha 1H), 6.61 (s, 1H), 4.89 (q, 7= 7.0 Ha 1 H), 4.38 -4.33 (m, 1H), 4.27 -4.23 (m, 1H),4.14-4.11 (m, 2H), 3.42 (s, 3 H), 1.78 (s, 3H), 1.71 (s, 3H), 1.48 (d, 7= 7.0 Ha 3H). |
260 | 1 Α° ο=ς ζ— ο LL | CH(Me) | O | o | Χ°ΥΊ VO | Cl | F | CH | |
261 | <Τ Ο —Ζ )=ο | CH(Me) | 0 | o | ^0^0^ | Cl | F | CH | |
262 | ο=< ζ— ο LL | CH(Me) | o | 0 | Cl | F | CH | 1H NMR (500 MHa DMSO-d6) δ 8.59 (s, 1H), 8.01 (d, J = 8.0 Ha 1H), 7.89 (d, J = 9.0 Ha 1H), 7.48-7.43 (m, 2H), 7.33-7.29 (m, 1H), 7.16- 7.14 (m,2H), 6.63 (s, 1 H), 5.17 (q, J = 7.0 Ha 1H), 3.44 (s, 3H), 1.65 (d, J = 7.0 Ha 3H). |
263 | JA O=J Z— O LL | CH(Me) | O | O | 0 v°'rA | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.58 (s, 1 H), 7.98 (d,7= 7.5 Hz, 1H), 7.90 (d, 7=9.5 Hz, 1 H), 6.62 (s, 1H), 5.35 (q,7= 7.0 Hz, 1H), 3.43 (s, 3H), 2.80-2.84 (m,4H), 1.64 (d, 7= 7.0 Hz, 3H). |
264 | JA O=Z z— O LL | CH(Me) | O | O | Ao | Cl | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 7.96-7.82 (m, 2H), 6.61 (s, 1H), 4.97-4.82 (m, 111),4.193.98 (m, 3H), 3.76-3.55 (m, 2H), 3.42 (s, 3H), 1.98-1.71 (m, 3H), 1.61 1.41 (m,4H). |
265 | J1 O —Z Ao OA | CH(Me) | O | s | A L ° | Cl | F | CH | |
266 | J-7 o=< z— O LL | CH(Me) | O | O | A OA | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.94-7.83 (m, 2H), 6.61 (s, 1H), 5.08-5.06 (m, 1 H), 4.91 (q, 7=7.0 Hz, 1H), 4.14-4.02 (m, 2H), 3.88-3.86 (m, 2H), 3.81-3.79(m, 2H), 3.43 (s, 3H), 1.48 (d, 7= 7.0 Hz, 3H). |
267 | J1 O —z \=o □A | CH(Me) | O | 0 | Ao v_/k VJ | Cl | F | CH | |
268 | JA O=J z— O IL | CH(Me) | O | 0 | Ao \ sx VJ | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.50 (s, 1H), 7.88-7.84 (m, 2H), 7.52 (t,7= 5.0 Hz, 1H), 7.17-7.15 (m, 1H), 6.99 (d, 7= 4.5 Hz, 1H), 6.63 (s, 1H), 5.40 — 5.32 (m,2H), 4.96-4.86 (m, 1H), 3.43 (s, 3H), 1.46 (d, 7= 7.0 Hz, 3H). |
269 | J1 O —Z 7=0 □A | CH(Me) | O | O | Ao \ /S. VJ | Cl | F | CH |
270 | Π ω Ο —ζ y=o | CH(Me) | O | o | A <ο L ZI | Cl | F | CH | |
271 | ω1 Ο —Ζ /=Ο οΑ | CH(Me) | O | o | Ao V .N. H | Cl | F | CH | |
272 | ω1 Ο —ζ )=ο | CH(Me) | O | o | Ao i | Cl | F | CH | |
273 | ω1 ο —Ζ | CH(Me) | o | o | A° i ^-N chf2 | Cl | F | CH | |
274 | ο=< ζ— ο IL | CH(Me) | o | o | C°2Et Nv° | Cl | F | CH | |
275 | Α° ο=< ζ— ο if? | CH(Me) | o | o | Ao N—' | Cl | F | CH | |
276 | X /° JM ο=< ζ— ο IL | CH(Me) | o | o | O-A An | Cl | F | CH | |
277 | <τ ο —Ζ Αο οΑ | CH(Me) | o | o | °^\ A | Cl | F | CH | |
278 | 1 Α° ο=< ζ— ο IL | CH(Me) | o | o | z O | Cl | F | CH | |
279 | <? ο —Ζ Λ=Ο | CH(Me) | 0 | 0 | Ao \ o. Il N-N | Cl | F | CH | |
280 | Α° ο=< ζ— ο LL | CH(Me) | o | o | Z;=/ | Cl | F | CH | |
281 | ω1 Ο —Ζ /=Ο οΑ | CH(Me) | o | o | Ao i V'N n-4 | CI | F | CH | |
282 | Α° ο=< ζ— ο IL | CH(Me) | o | o | ,Z-Z —Z 1 ^0-7 | Cl | F | CH |
283 | J Ο —Z \=° fa | CH(Me) | O | O | /O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-d6) δ 8.51 (s, 1H), 7.95-7.90 (m, 2H), 7.39 - 7.24 (m, 5H), 6.63 (s, 1H), 5.26-5.22 (m, 1H), 5.19-5.14 (m, 1 H), 4.97-4.92 (m, 1H), 3.43 (s, 3H), 1.49 (d, J= 7.0 Hz, 3H). |
284 | J1 o | CH(Me) | O | O | A° | Cl | F | CH | 1H NMR (500 MHz, DMSO-d6) δ 8.50 (s, 1H), 7.94-7.85 (m, 2H), 7.46-7.40 (m, 2H), 7.23 — 7.15 (m, 2H), 6.63 (s, 1H), 5.32-5.27 (m, 1H), 5.24-5.18 (m, 1H), 4.94 (q, J = 7.0 Hz, 1 H), 3.43 (s, 3H), 1.48 (d, J = 7.0 Hz, 3H). |
285 | ω1 Ο —Z Y=O | CH(Me) | O | O | F | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfs) δ 8.52 (s, 1H), 7.92 -7.87 (m, 2H), 7.41 -7.35 (m, 1H),7.22 — 7.17 (m,2H), 7.17-7.10 (m, 1H), 6.63 (s, 1H), 5.29-5.15 (m, 2H), 5.00 -4.95 (m, 1H), 3.43 (s, 3H), 1.51 (d,J=7.0 Hz, 3H). |
286 | J1 o —Z \=o | CH(Me) | O | O | X) Q Tl | Cl | F | CH | ‘H NMR (500 MHz, DMSO-<4) δ 8.50 (s, 1H), 7.93 - 7.87 (m, 2H), 7.41-7.38 (m, 2H), 7.17-7.12 (m, 2H), 6.62 (s, 1H), 5.23-5.14 (m, 2H), 4.94 (q, .7=7.0 Hz, 1H), 3.44 (s, 3H), 1.49 (d, .7= 7.0 Hz, 3H). |
287 | 0 A f3c^n^o | CH(Me) | O | O | /O | Cl | F | CH | |
288 | J1 o —Z \=O | CH(Me) | O | 0 | 'O | Cl | F | CH |
289 | ω1 Ο —ζ Α° fa | CH(Me) | O | O | Ao cf3 | Cl | F | CH | |
290 | fa° ο=< ζ— ο d? | CH(Me) | O | O | Ao ^A^~NO2 | Cl | F | CH | |
291 | A Ο=< ζ— ο LL? | CH(Me) | O | O | Ao 'V^Ayk'CN | Cl | F | CH | |
292 | A ο=< ζ— ο ιί | CH(Me) | O | O | £~o OMe IA | Cl | F | CH | |
293 | A ο=< ζ— ο IX | CH(Me) | O | O | /Ό ^A^SEt | Cl | F | CH | |
294 | ω1 Ο —ζ Αο | CH(Me) | O | O | Ao__/nh2 | Cl | F | CH | |
295 | ω1 Ο —ζ Α° | CH(Me) | O | O | /O 'V^A/^~'SO2Me | Cl | F | CH | |
296 | ο Αλ Ρ3θΑ Ί3 | CH(Me) | O | O | Ao__zCOOEt | Cl | F | CH | |
297 | JA ο=< Ζ— ο d? | CH(Me) | O | O | Cl | F | CH | ||
298 | J1 ο —ζ Α° ο | CH(Me) | O | O | AA | Cl | F | CH | |
299 | ο=< ζ— ο ιχ? | CH(Me) | 0 | O | ^°A/A AA~~cooh | Cl | F | CH | |
300 | A □=< ζ— ο IX | CH(Me) | O | O | Ao A^OMe | Cl | F | CH | |
301 | ω1 Ο —ζ Αο οΑ | CH(Me) | O | O | A r0 / Z Aa | Cl | F | CH | 1HNMR(5OO MHz, Chloroform-d) δ 8.63 - 8.56 (m, 2H), 7.85 (d, J = 7.5 Hz, 1 H), 7.68 (d, J = 8.0 Hz, |
1H), 7.36 (d, J = 9.0 Hz, 1 H), 7.21 -7.25(m,2H), 6.41 (s, 1H), 5.27 (s, 2H), 4.87 (q, J = 7.0 Ha 1H), 3.61 (d, J = 4.0 Ha 3H), 1.57 (d, J = 7.0 Ha 3H). | |||||||||
302 | TA o=< z— O LL? | CH(Me) | O | O | Ao l/=sN V? | Cl | F | CH | lHNMR(500 MHa Chlorofonn-d) δ 8.62 - 8.59 (m, 2H), 8.54 (s, 1H), 7.81 (d,J = 7.5 Ha 1H), 7.71 (d, J = 4.5 Ha 1H), 7.36 (d, J = 9.0 Ha 1H), 7.30 -7.28 (m, 1H), 6.42 (s, 1H), 5.27 (s, 2H), 4.87 (q, J = 7.0 Ha 1H), 3.61 (d, J = 4.0 Ha 3H), 1.57 (d, J = 7.0 Ha3H). |
303 | 0 /a f3An^o | CH(Me) | O | O | Ao | Cl | F | CH | *HNMR(500 MHa DMSO-rfs) δ 8.58 (d, .7=5.0 Ha2H), 8.17 (s, 1H), 7.63 (d,J= 5.0 Ha 2H), 7.30 (d, J =9.0 Ha 1H), 7.25-7.19 (m, 1H), 6.43 (s, 1H), 5.28 (s, 2H), 4.87 (q, J= 7.0 Ha 1 H), 3.62 (s, 3H), 1.56 (d, J=7.0 Ha 3H). |
304 | J1 O —Z /=O oA | CH(Me) | O | O | Ao N-A | Cl | F | CH | |
305 | □=/ z— O LL? | CH(Me) | O | O | Ao | Cl | F | CH | |
306 | JA o=< z— O LL | CH(Me) | O | O | A <° rs^\ z Χχ, Z | Cl | F | CH | |
307 | TA o=< z— O IL? | CH(Me) | O | O | A'o O | Cl | F | CH | |
308 | TA z— O IL | CH(Me) | O | O | O | Cl | F | CH |
309 | O=\ Z— O l£? | CH(Me) | O | O | A Γ° O | Cl | F | CH | |
310 | 0 f3c n^o | CH(Me) | O | O | A° _/==> | CI | F | CH | |
311 | J1 O —Z Vo □A | CH(Me) | O | O | A Λ° O | Cl | F | CH | |
312 | J1 O —Z Ao □A | CH(F) | O | O | OMe | Cl | F | CH | |
313 | A o=/ Z— O LL? | CH(F) | O | O | OEt | Cl | F | CH | 1HNMR(5OO MHz, DMSO) δ 8.55 (s, 1H), 7.95-7.83 (m, 2H), 6.61 (d,J= 2.0 Hz, 1H), 5.37 - 5.32 (tn, 1H), 4.19 (q, 7=6.0 Hz, 2H),3.43 (s, 3H), 1.24 (t, 7= 6.0 Hz, 3H). |
314 | 0 f3AaKd | CH(C1) | O | 0 | OMe | Cl | F | CH | |
315 | J1 O —z Ao □A | CH(Et) | O | O | OMe | Cl | F | CH | ‘HNMR(500 MHz, DMSO-</6) δ 8.54 (s, 1H), 7.95-7.83 (m, 2H), 6.61 (s, 1H), 4.74 (t, 7= 7.5 Hz, 1H), 3.70 (s, 3H), 3.43 (s, 3H), 1.93-1.79 (m, 2H), 0.98 (t, 7= 7.5 Hz, 3H). |
316 | JH O=< Z— O d? | CH | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.53 (s, 1 H), 7.92 (d, 7= 8.0 Hz, 1H), 7.88 (d, 7=9.5 Hz, IH), 6.61 (s, 1H), 4.78 (t, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 3.42 (s, 3H), 1.81-1.78 (m, 2H), 1.46-1.42 (m, 2H), 0.94 (ζ 7= 7.0 Hz, 3H). |
317 | <? O —Z Ao oA | CH | O | O | OEt | Cl | F | CH |
318 | «J1 Ο —Z Ao oA | ^CH | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.54 (s, 1H), 7.94-7.87 (m, 2H), 6.61 (s, 1 H), 4.57 (d, J= 5.0 Hz, 1H), 3.70 (s, 3H), 3.42 (s, 3H), 2.20-2.13 (m, 1H), 1.00 (d, J= 6.5 Hz, 6H). |
319 | <7 o —z y=o oA | Y CH | O | 0 | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.54 (s, 1H), 7.97-7.85 (m, 2H), 6.61 (s, 1 H), 4.23 (q, J= 7.0 Hz, 2H), 4.19 (d, 7= 9.0 Hz, 1H), 3.71 (s, 3H), 1.29-1.21 (m, 4H), 0.66-0.63 (m, 2H), 0.58-0.49 (m, 2H). |
320 | J1 O —Z )=O | CH(CF3) | 0 | O | OMe | Cl | F | CH | |
321 | J O —Z /=O oA | CH(OMe) | O | O | OMe | CI | F | CH | ‘H NMR (500 MHz, Chloroform-7) δ 8.64 (s, 1H), 7.89 (d, 7= 7.5 Hz, 1H), 7.37 (d, 7= 9.0 Hz, 1H), 6.41 (s, 1H), 5.48 (s, 1 H), 3.87 (s, 3H), 3.61-3.56 (m, 6H). |
322 | ÔP O -zA=° fa 1 | CH(OMe) | O | O | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.63 (s, 1H), 7.96-7.89 (m, 2H), 6.62 (s, 1H), 5.60 (s, 1H), 4.23-4.18 (m, 2H), 3.47 (s, 3H), 3.43 (s, 3H), 1.24-1.21 (m, 3H). |
323 | J O —Z )=o o'Z' | CH(OMe) | O | O | ’^O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.63 (s, 1 H), 7.95-7.89 (m, 2H), 6.62 (s, 1H), 5.62 (s, 1 H), 4.15-4.09 (m, 2H), 3.47 (s, 3 H), 3.43 (s, 3H), 1.64-1.59 (m,2H), 0.98 — 0.73 (m, 3H). |
324 | J1 O —Z )=o | CH(OMe) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rf6) δ 8.62 (s, 1H), 7.95-7.89 (m, 2H), 6.61 (s, 1H), 5.56 (s, 1H), 5.08-4.85 |
(m, 1H), 3.46-3.43 (m, 6H), 1.25-1.18 (m, 6H). | |||||||||
325 | o=Z z— O d? | CH(OMe) | O | O | ’^'o | Cl | F | CH | |
326 | O=< Z— O d? | CH(OMe) | O | O | ^o F | Cl | F | CH | |
327 | O ° \=/z- ' O æ | CH(OMe) | 0 | O | Ad ^cf3 | Cl | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.02 (s, 1H), 7.34 (d, 7= 9.0 Hz, 1H), 7.22 (d, 7=5.5 Hz, 1H), 6.26 (s, 1H), 6.24 (s, 1H), 5.34-5.26(m, 1H), 4.12-4.00 (m, 1H), 4.10-4.02 (m, 3H), 3.34 (s, 3H). |
328 | <? O _zh=° | CH(OMe) | O | O | ’^o OMe | Cl | F | CH | |
329 | O f3c^n^o | CH(OMe) | O | O | ^O OEt | Cl | F | CH | |
330 | 0 iV f3c^n^o | CH(OMe) | O | O | ^0 ’ Z) | Cl | F | CH | Ή NMR (500 MHz, DMSO-</6) δ 8.61 (s, 1H), 7.96-7.87 (m, 2H), 7.41-7.29 (m, 5H), 6.63 (s, 1H), 5.68 (s, 1H), 5.29-5.18 (m, 2H), 3.47 (s, 3H), 3.43 (s, 3H). |
331 | O=< Z— O d? | CH | O | O | OMe | Cl | F | CH | 1H NMR (500 MHz, DMSO) δ 8.62 (s, 1H), 7.94-7.86 (m, 2H), 6.61 (d,7= 2.0 Hz, 1 H), 5.36 (s, 1H), 3.48 (s, 3 H), 3.43 (s, 3H), 3.31-3.21 (m,2H), 1.531.42 (m, 3H). |
332 | Ô îV f3c^n^o 1 | ς CH | O | O | OEt | Cl | F | CH |
333 | JA ο=ς ζ— ο d? | 1 CH | O | 0 | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-A) δ 8.56 (s, 1 H), 7.97-7.83 (m, 2H), 6.61 (s, 1H), 5.03-4.99 (m, 1 H), 3.873.74 (m, 2H), 3.71 (s, 3H), 3.43 (s, 3H), 3.36 (s, 3H). |
334 | J ο —ζ )=ο | 1 ο CH | 0 | 0 | OEt | Cl | F | CH | |
335 | Η ο=ς ζ— ο IL· | O'CF3 ^CH | O | O | OEt | Cl | F | CH | |
336 | ω1 Ο —Ζ )=Ο | CH(COOMe) | O | O | OMe | Cl | F | CH | |
337 | Η ο=< ζ— ο d? | CH(Ph) | O | 0 | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO-<4) δ 8.61 (s, 1H), 7.95 (t, 7= 7.5 Hz, 1H), 7.89 (d, 7=9.5 Hz, 1H), 7.47-7.32 (m, 5H) 6.62 (s, 1 H), 5.17 (s, 1H), 3.70 (s, 3H), 3.43 (s, 3H). |
338 | ο=< ζ— ο d? | CH(CN) | O | O | OMe | Cl | F | CH | |
339 | ω1 ο —Ζ 2=0 | CH(Me) | O | O | OMe | Br | F | CH | |
340 | 0 Λ* F3C Ν Ο | CH(Me) | O | O | OEt | Br | F | CH | |
341 | ω1 Ο —Ζ \=ο fa | CH(Me) | O | O | A O | Br | F | CH | |
342 | ο=< ζ— ο d? | CH(Me) | O | O | OMe | cf3 | F | CH | Ή NMR (500 MHz, DMSO-rfs) δ 8.45 (s, 1H), 8.19-8.05 (m, 2H), 6.65 (s, 1 H), 4.93 (q, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 3.44 (s, 3H), 1.48 (d,7= 7.0 Hz, 3H). |
343 | □=< ζ— ο d? | CH(Me) | O | O | OEt | CFj | F | CH | |
344 | fa O=C Z— o d? | CH(Me) | 0 | O | OMe | CN | F | CH | ‘H NMR (500 MHz, DMSO-Js) δ 8.48 (s, 1H), 8.27 (d, 7= 9.0 Hz, IH), 8.05-8.03 (m, 1H), 6.65 (s, 1 H), 4.93 (q, 7= 7.0Hz, 1H), 3.70 (s, 3H), 3.43 (s, 3H), 1.50 (d, 7= 7.0 Hz, 3H). |
345 | O=< Z— o l£? | CH(Me) | O | O | OEt | CN | F | CH | |
346 | □=/ Z— o d? | CH(Me) | O | O | OEt | CI | F | N | |
347 | / b if | CH(Me) | O | O | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.54 (s, 1H), 8.18 (d,7= 8.0 Hz, 1H), 8.04 (d, 7= 9.5 Hz, IH), 6.95 (s, IH), 4.90 (q, 7= 7.0 Hz, IH), 3.70 (s, 3 H), 3.36 (s, 3H), 1.48 (d, 7= 7.0Hz, 3H). |
348 | ”=0 / b LL | CH(Me) | O | O | OEt | Cl | F | CH | |
349 | 0 f3c/^^s | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-ds) δ 8.51 (s, IH), 7.95-7.86 (m, 2H), 7.10 (s, IH), 4.89 (q, 7= 7.0 Hz, 1 H), 3.70 (s, 3H), 3.42 (s, 3H), 1.47 (d, 7= 7.0 Hz, 3H). |
350 | Π ω °\ / A CO γΛ | CH(Me) | O | O | OEt | Cl | F | CH | |
351 | s XN'^'N^ FaC^^^S | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.54 (s, IH), 8.18 (t,7=7.0 Hz, IH), 8.06 (d, 7= 9.0 Hz, IH), 7.62 (s, IH), 4.91 (q,7=7.0 Hz, IH), 3.70 (s, 3H), 3.35 (s, 3H), 1.48 (d,7= 7.0 Hz, 3H). |
352 | S | CH(Me) | O | O | OEt | Cl | F | CH | |
353 | ω1 O / ω A | CH(Me) | O | s | OMe | Cl | F | CH | |
354 | v? « / b C*î LL | CH(Me) | O | s | OEt | Cl | F | CH | |
355 | 0 A^lA | CH(Me) | O | O | '/'O | Cl | F | CH | |
356 | 0 'Λ* f3c/^/^s | CH(Me) | O | O | Cl | F | CH | ||
357 | O XN^N'^ f3c'vA | CH(Me) | O | O | Ao | Cl | F | CH | |
358 | ΊΊ ω ω r*· | CH(Me) | O | 0 | oX h. | Cl | F | CH | |
359 | J1 °\ / (Λ | CH(Me) | 0 | O | Ao | Cl | F | CH | |
360 | 0 A^fA f3c'x^ïA>s | CH(Me) | O | O | b o \ | Cl | F | CH | |
361 | tn A / b CO LL | CH(Me) | O | O | Ao 0^ | Cl | F | CH | |
362 | 0 A^fA f3cAAs | CH(Me) | O | O | /^o °A | Cl | F | CH | |
363 | 0 xfAfA f3(AA | CH(Me) | 0 | 0 | /0 \ | Cl | F | CH | |
364 | 0 xfAfA f3cAAs | CH(Me) | O | O | 0 | Cl | F | CH | |
365 | ü 'fAfA f3cAAs | CH(Me) | O | O | 0 | Cl | F | CH | |
366 | 0 A^fA f3cAAs | CH(Me) | O | O | X. r° °y° | Cl | F | CH |
367 | y1 ,w / b CO | CH(Me) | O | O | ho | Cl | F | CH | |
368 | O hAhf3c^^s | CH(Me) | O | O | ho h^-O^ | Cl | F | CH | |
369 | =7 °\ / (Λ A | CH(Me) | O | O | ho ^^0 | Cl | F | CH | |
370 | 0 ,<α,λ f3c^^s | CH(Me) | O | O | ho | Cl | F | CH | |
371 | J1 (Λ r* | CH(Me) | O | O | Z / o-^ “h | Cl | F | CH | |
372 | 0 FaC^^S | CH(Me) | O | O | ho V? | Cl | F | CH | |
373 | ! Tl ω h ω | CH(Me) | O | O | /'O | Cl | F | CH | |
374 | ü F3C^^S | CH(F) | O | O | OMe | Cl | F | CH | |
375 | J1 °\_ Z f>° ω | CH(F) | O | O | OEt | Cl | F | CH | |
376 | J1 ω r* | CH(C1) | O | O | OMe | Cl | F | CH | |
377 | ü FaC-^^S | CH(Et) | O | O | OMe | Cl | F | CH | |
378 | 'jj ω / b <*5 LL | CH | O | O | OMe | Cl | F | CH | |
379 | v? ω / b (Ό LL | CH | 0 | 0 | OEt | CI | F | CH | |
380 | “Π w °\ / l>° (n | ^CIH | 0 | O | OMe | Cl | F | CH | |
381 | v? ω / b cri LL | Y CH | O | O | OEt | CI | F | CH |
382 | 0 f3c^^s | CH(CFj) | O | o | OMe | Cl | F | CH | |
383 | CO / o: <*3 LL | ς CH | O | o | OMe | Cl | F | CH | |
384 | J1 °\ / (Λ t* | ς CH | O | o | OEt | Cl | F | CH | |
385 | J1 O\ / ω A | 1 0^ CH | o | o | OMe | Cl | F | CH | |
386 | 0 F3Cx^^S | CH(COOMe) | 0 | 0 | OMe | Cl | F | CH | |
387 | J1 °\ / U> r* | CH(Ph) | o | o | OMe | Cl | F | CH | |
388 | O FaC^^^S | CH(Me) | o | 0 | OMe | Br | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.46 (s, 1H), 8.02 (d, J= 9.0Hz, 1H), 7.88 (d, 7= 7.5Hz, 1H), 7.09 (s, 1 H), 4.89 (q, 7= 7.0Hz, 1H), 3.69 (s, 3H), 3.42 (s, 3H), 1.47 (d, 7= 7.0 Hz, 3H). |
389 | J1 °\ / x>° CO r* | CH(Me) | o | 0 | OMe | CFj | F | CH | |
390 | O FaC^^^S | CH(Me) | o | o | OMe | CN | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.48 (s, 1H), 8.29 (d, 7 =9.0 Hz, 1H), 8.05-8.03 (m, 1H), 7.13 (s, 1 H), 4.94 (q, 7= 7.0Hz, 1H), 3.71 (s, 3H), 3.42 (s, 3H), 1.49 (d, 7= 7.0 Hz, 3H). |
391 | J1 °\ / CO | CH(Me) | 0 | 0 | OMe | Br | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.48 (s, 1H), 8.19 (d, 7= 9.0 Hz, 1H), 8.15-8.12 (tn, 1H), 7.62 (s, 1 H), 4.91 (q, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 2.53 (s, 3H), 1.48 (d, 7= 7.0 Hz, 3H). |
392 | S | CH(Me) | O | O | OMe | cf3 | F | CH | Ή NMR (500 MHz, DMSO-î/6) δ 8.44 (s, 1H), 8.38-8.35 (m, 1H), 8.24 (d, J= 9.5 Hz, 1 H), 7.63 (s, 1H), 4.92 (q, 7=7.0Hz, 111), 3.68 (s, 3H), 2.53 (s, 3H), 1.46 (d, 7=7.0 Hz,3H). |
393 | S f3c^^s | CH(Me) | O | O | OMe | CN | F | CH | Ή NMR (500 MHz, DMSO-7È) ôll.22(s, 1H), 8.92 (d,7= 9.0 Hz, 1H), 8.66 ( d, 7= 7.0Hz, 1H), 8.46 (s, 1 H), 5.01 (q, 7= 7.0 Hz, 1H), 3.74 (s, 3H), 2.53 (s, 3H), 1.53 (d, 7= 7.0 Hz, 311) |
394 | s FaC^^O | CH(Me) | O | O | OMe | Br | F | CH | Ή NMR (500 MHz, DMSO-A) δ 8.48 (s, 1H), 8.17-8.15 (m, 2H), 6.95 (s, 1 H), 4.90 (q, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 3.36 (s, 3H), 1.48 (d, 7= 7.0 Hz, 3H). |
395 | S FaC^^O | CH(Me) | O | O | OMe | CF3 | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.47 (s, 1H), 8.40-8.38 (m, 1H), 8.23 (d, 7= 9.5 Hz, 1 H), 6.99 (s, 1H), 4.94 (q, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 2.54 (s, 3H), 1.49 (d, 7= 7.0 Hz, 3H). |
396 | S xn^nV FaC^^^O | CH(Me) | O | O | OMe | CN | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.49 (s, 1H), 8.42 (d, 7= 9.0 Hz, 1H), 8.32 (d, 7= 7.0Hz, 1H), 6.99 (s, 1H), 4.94( q, 7= 7.0 Hz, 1H), 3.71 (s, 3H), 2.55 (s, 3H), 1.51 (d, 7= 7.0 Hz, 3H). |
397 | Ô JL A F3cAA) | CH(Me) | O | O | SMe | Cl | F | CH | |
398 | 0 jlY F3C N^O | CH(Me) | 0 | O | SEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.51 (s, 1 H), 7.94-7.85 (m, 2H), 6.61 (s, 1 H), 4.97 (q, 7= 7.0 Hz, 1 H), 4.81 (q, 7= 7.0 Hz, 2H), 3.42 (s, |
3H), 1.45 (d,J= 7.0Hz,3H), 1.20 (t, J =7.0 Hz, 3H). | |||||||||
399 | J Ο —z Το oT | CH(Me) | O | O | Cl | F | CH | Ή NMR (500 MHz, DMSO-A) δ 8.58 (s, 1H), 7.95 (d, J =8.0 Hz, 1H), 7.89 (d, ./=9.5 Hz, 1 H), 6.61 (s, 1H), 4.93 (q,J= 7.0 Hz, 1H), 3.42 (s, 3H), 2.87-2.81 (m,2H), 1.56 — 1.51 (m, 2H), 1.47 (d, J =7.0 Hz, 3H), 0.93 — 0.88 (m, 3H). | |
400 | ω1 Ο —ζ Το οΤ | CH(Me) | O | O | \'Y | Cl | F | CH | Ή NMR (500 MHz, DMSO-A) δ 8.57 (s, 1H), 7.97-7.95 (m, 1H), 7.89 (d, J= 9.5 Hz, 1H), 6.61 (s, 111),4.924.88 (m, 1H), 3.58-3.51 (m, 1H), 3.43 (s, 3H), 1.45 (d,J= 7.0 Hz, 3H), 1.26 (d, 7=6.5 Hz, 6H). |
401 | ω1 Ο —ζ Το οΤ | CH(Me) | O | O | As | Cl | F | CH | |
402 | <? ο —ζ Το οΤ | CH(Me) | O | O | s^ À | Cl | F | CH | |
403 | ω1 Ο —ζ Το | CH(Me) | O | O | As | Cl | F | CH | |
404 | ω1 Ο —ζ Το οΤ | CH(Me) | 0 | O | As 0^ | Cl | F | CH | |
405 | ο=< ζ— ο IL? | CH(Me) | O | O | /S \ | Cl | F | CH | |
406 | τ° ο=ς ζ— ο η LL | CH(Me) | O | O | o— | Cl | F | CH | ‘H NMR (500 MHz, DMSO-A) δ 8.63 (s, 1H), 8.00-7.94 (m, 1H), 7.90 (d, J= 9.5 Hz, 1 H), 6.61 (s, 1H), 5.00 (d, ./=7.5 Hz, 1H), 3.82 (s,2H), 3.64 (s, 3H), 3.42 (s, 3H), 1.47 (d, J =7.0 |
Hz, 3H). | |||||||||
407 | JA o=< z— $ | CH(Me) | O | o | As °Λ K AoAo | Cl | F | CH | |
408 | JA O=J z— o d? | CH(Me) | O | o | 5 EMBED Unknown As | Cl | F | CH | |
409 | J1 o —z J=o | CH(Me) | O | o | As | Cl | F | CH | ‘H NMR (500 MHz, DMSO-<4) δ 8.58 (s, IH), 7.94 (d, 7= 8.0 Hz, IH), 7.89 (d, 7=9.5 Hz, 1 H), 7.30 - 7.28 (m, 5H), 6.62 (s, IH), 4.99 (q,7= 7.0 Hz, 1 H), 4.14 (s, 2H), 3.43 (s, 3H), 1.47 (d, 7= 7.0 Hz, 3H). |
410 | J1 o —Z /=O | CH(Me) | o | o | As V? | Cl | F | CH | |
411 | JA O=J z— o d? | CH(Me) | o | o | SEt | CN | F | CH | |
412 | J1 ω | CH(Me) | o | 0 | SMe | Cl | F | CH | |
413 | Tl w °\ / ω | CH(Me) | o | o | SEt | Cl | F | CH | |
414 | J1 o —Z /=O | CH(Me) | 0 | 0 | NHEt | Cl | F | CH | |
415 | J1 o —z )=o | CH(Me) | o | o | Anh A o \ | Cl | F | CH | |
416 | JA O=J z— o d? | CH(Me) | o | o | 1 ΛΛ/7 Z Ljo °\ | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.53 (s, IH), 8.03 (s, 1 H), 7.95 (d, 7= 8.0 Hz, IH), 7.88 (d, 7=9.5 Hz, 1H),6.61 (s, IH), 4.63 (d, 7= 7.0 Hz, IH), 3.54 (s, 3H), 3.42 (s, 3H), 3.34-3.29 (m,2H), 2.48-2.45 (m, 2H), 1.38 (d, 7= 7.0 Hz, 3H). |
417 | Ο f^nX | CH(Me) | O | o | Anh | Cl | F | CH | |
418 | □=< ζ— Ο d? | CH(Me) | 0 | o | /NH | Cl | F | CH | |
419 | 0 fXXo | CH(Me) | O | o | ^z— / o | Cl | F | CH | Ή NMR (500 MHz, DMSO-d6) δ 8.49 (s, 1H), 7.94-7.80 (m, 2H), 6.62 (s, 1H), 5.19 (d, 7= 7.0 Hz, 1H), 3.72 (s, 3H), 3.43 (s, 3H), 3.14 (s, 3H), 1.41 (d,7= 7.0Hz,3H). |
420 | ? —ζ Χο οΧ | CH(Me) | o | o | H O - | Cl | F | CH | |
421 | ο=< ζ— ο d? | CH(Me) | o | o | Anh O^'°z °zN Λ | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.48 (s, 1H), 7.95-7.83 (m, 2H), 6.62 (s, 1H), 5.22-5.20 (m, 1H), 3.95-3.93 (m, 1H), 3.42 (s, 3H), 3.04 (s, 3H), 1.38 (d, 7= 7.0 Hz, 3H), 1.06 (d, 7= 7.0 Hz, 6H). |
422 | J1 Ο —ζ \=ο οΧ | CH(Me) | o | o | Anh >/ °/N A | CN | F | CH | |
423 | ω1 Ο —Ζ /=Ο οΧ | CH(Me) | 0 | o | H VNY°^ 0 | Cl | F | CH | |
424 | ω1 Ο —Ζ \=ο οΧ | CH(Me) | o | o | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.57 (s, 1H), 7.90-7.88 (m, 2H), 6.59 (s, 1H), 6.26 (s, 1H), 5.96-5.94(m, 1H), 3.40 (s, 3H), 2.50 (s, 3H), 2.21 (s, 3H), 1.57 (d, 7= 7.0 Hz, 3H). | |
425 | ο f3c'zÎî!ï^s | CH(Me) | 0 | 0 | Anh o>°z °/N Λ | Cl | F | CH |
426 | ι ο J-γ | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSCWs) δ 8.52 (s, 1 H), 7.98-7.95 (m, 1H), 7.88 (d, J= 9.5 Hz, 1H), 6.60 (s, 1H), 4.90 (q, 7= 7.0 Hz, 1H), 3.89 (q, 7= 7.0 Hz, 2H), 3.70 (s, 3H), 1.47 (d, 7= 7.0 Hz, 3H), 1.26 (t, 7 =7.0 Hz, 3H). |
427 | •V° =—/ ο LL | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-c/e) δ 8.52 (s, 1H), 7.99 (d, 7= 8.0 Hz, 1H), 7.90 (d, 7=9.5 Hz, 1H), 6.70 (s, 1H), 4.96 - 4.88 (m, 1H), 4.74-4.54 (m, 2H), 3.70 (s, 3H), 3.53-3.41 (m, 1H), 1.47 (d, 7=7.0 Hz, 3H). |
428 | F Ο f^n^nA F3C/J<5ï>/^0 | CH(Me) | O | O | OMe | Cl | F | CH | |
429 | 4ί ο ο CO . co LL LL | CH(Me) | O | O | OMe | Cl | F | CH | |
430 | *Π -7 ω — O O A | CH(Me) | O | O | OMe | Cl | F | CH | |
431 | O F3c'xy^° Cl | CH(Me) | O | 0 | OMe | Cl | F | CH | 1H NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.98-7.86 (m, 2H), 4.90-4.88 (m, 1H), 3.70 (s, 3H), 3.47 (s, 3H), 1.47 (d, J = 7.0 Hz, 3H). |
432 | n T ω ι3- O Z/l oa2Ao | CH(Me) | 0 | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-dj) δ 8.49 (s, 1H), 7.86-7.56 (m, 2H), 4.89 (t, 7= 7.0 Hz, 1H), 3.71 (s, 3H), 3.55 (s, 3H), 3.03 (s, 2H), 2.97-2.66 (m, 2H), 1.47 (d, 7= 7.5 Hz, 3H). |
433 | <? . O —z Ao □A | C(Me)i | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.46 (s, 1H), 7.90-7.88 (m, 2H), 6.63 (s, 1H), 3.67 (s, 3H), 3.43 (s, 3H), 1.54 (s, 6H). |
434 | J Ο —Z )=o | C(Me)2 | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.47 (s, 1H), 7.91-7.84 (m, 2H), 6.64 (s, 1 H), 5.88-5.87 (m, 1H), 5.24-5.22 (m, 2H), 4.63 (d, J= 5.0 Hz, 2H), 3.43 (s, 3H), 1.55 (s, 6H). | |
435 | J1 o -z^o □A | C(F)2 | O | O | OMe | Cl | F | CH | |
436 | 0 XN^N'^ FsC'^^S | C(Me)2 | 0 | O | OMe | Cl | F | CH | |
437 | J1 ω r* | C(F)2 | O | O | OMe | Cl | F | CH | |
438 | A° Α-Γ ' <n | CH(Me) | O | O | OH | Cl | F | CH | ‘H NMR (500 MHz, DMSO-<4) δ 12.84 (s, 1H), 8.49 (s, 1H), 8.05 (d, 7= 8.0 Hz, 1H), 7.89 (d, 7=9.5 Hz, 1H), 4.76 (q, 7= 7.0 Hz, 1H), 3.64 (s, 6H), 1.46 (d, 7= 7.0 Hz, 3H). |
439 | ω / A -Z >O □H | CH(Me) | O | O | 7o ^~cf3 | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.55 (s, 1H), 8.02-8.01 (m, 1H), 7.91-7.90 (m, 1H), 5.05-5.04 (m, 1 H), 4.99-4.77 (m, 2H), 3.64 (s, 6H), 1.52 (d, 7= 7.0 Ha 3H). |
440 | Jt-4. Aa 7 ω | CH2CH2 | O | 0 | OMe | Cl | F | CH | |
441 | ' tn | CH(Me)CH2 | O | O | OMe | Cl | F | CH | |
442 | 0=4 z— o LL? | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHa DMSO-76) δ 8.52 (s, 1H), 7.92 (d, 7 =7.5 Ha 1H), 7.88 (d, 7= 9.0 Ha 1H), 6.61 (s, 1H), 4.90 (q, 7= 7.0 Ha 1 H), 4.27 — 4.12 (m, 2H), 3.42 (s, 3H), 2.83-2.81 (m, |
1H), 2.15-2.02 (m, 2H), 1.49 (d, J= 7.0 Hz, 3H). | |||||||||
443 | <7 Ο —ζ /=ο oV | CH(Me) | O | O | CN | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 7.90 (d, 7= 7.5 Hz, 1H), 7.87 (d, 7= 9.5 Hz, 1H), 6.59 (s, 1H), 5.60 (q, 7= 6.5 Hz, 1 H), 5.024.94 (m, 1H), 3.40 (s, 3H), 1.57 (d, 7= 6.5 Hz, 3H), 1.49 (d, 7= 6.5 Hz, 3H). |
444 | ο=< ζ— ο IL | CH(Me) | 0 | O | X'Oxy^CN | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.93 (d, 7= 7.5 Hz, 1H), 7.88 (d, 7= 9.5 Hz, 1H), 6.61 (s, 1H), 5.18-5.02 (m, 1 H), 4.97-4.80 (m, 1H), 3.42 (s, 3 H), 2.96 -2.90 (m, 2H), 1.49 (d, 7= 6.5 Hz, 3H), 1.28 (d, 7= 6.0 Hz, 3H). |
445 | ω1 ο —ζ )=ο oV | CH(Me) | O | O | X-O\^XCN | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.53 (s, 1H), 7.93 (d, 7= 8.0 Hz, 1 H), 7.88 (d, 7=9.5 Hz, 1 H), 6.61 (s, 1H), 4.95 (q, 7= 6.5 Hz, 1 H), 4.364.15 (m,2H), 3.43 (s, 3H), 3.30-3.22 (m, 1H), 1.51 (d,7= 7.0 Hz, 3H), 1.28 -1.20(m, 3H). |
446 | ο=< ζ— ο ιί? | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.53 (s, 1 H), 7.96-7.85 (m, 2H), 6.61 (s, 1H), 4.90 (q, 7= 7.0 Hz, 1 H), 4.26 -4.13 (m,2H), 3.43 (s, 3H), 2.57-2.54 (m, 2H), 1.96-1.88 (m, 2H), 1.50 (d, 7= 7.0 Hz, 3H). | |
447 | ο=< ζ— ο ιΤ | CH(Me) | O | O | H.Ο. V X CN | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.54 (s, 1H), 7.94 (d, 7 =7.5 Hz, 1H), 7.88 (d, 7=9.5 Hz, 1 H), 6.61 (s, 1H), 4.96 (q, 7= 7.0 Hz, 1H), 4.27 — 4.13 (m,2H), 3.42 (s, 3H), 1.52 (d, 7 =7.0 |
Hz, 3H), 1.341.26 (m,2H), 1.16-1.12 (m, 2H). | |||||||||
448 | ! Π ω Ο ί Η | CH(Me) | O | O | 1 | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.51 (s, 1H), 7.91 (d, 7=8.0 Hz, 1H), 7.88 (d, 7 = 9.5 Hz, 1 H), 6.61 (s, 1H), 4.88 (q, 7= 6.5 Hz, 1 H), 4.294.23 (m, 1H), 4.22-4.12 (m, 1H), 3.43 (s, 3 H), 2.59-2.55 (m, 2H), 2.20 (s, 6H), 1.48 (d, 7= 7.0 Hz, 3H). |
449 | fa ο=< ζ— ο ιΤ | CH(Me) | O | 0 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.55 (s, 1H), 7.94 (d, 7= 8.0 Hz, 1H), 7.89 (d, 7=9.5 Hz, 1 H), 6.60 (s, 1H), 5.03 (q, 7= 7.0 Hz, 1H), 3.42 (s, 3H), 1.92 (s, 3H), 1.54 (d, 7= 7.0Hz,3H), 1.14 (s. 9H). | |
450 | ω1 Ο —ζ Αο fa | CH(Me) | 0 | O | /O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.55 (s, 1H), 7.92 (d, 7= 7.5 Hz, 1H), 7.89 (d, 7=9.5 Hz, 1H), 6.60 (s, 1H), 5.03 (q, 7= 7.0 Hz, 1H), 3.42 (s, 3H), 2.28-2.15 (m, 1H), 1.63 (s, 3H), 1.55 (d, 7= 7.0 Hz, 3H), 0.95 - 0.85 (m, 2H), 0.86-0.80 (m, 2H). |
451 | Ο=Υ ζ— ο IL· | CH(Me) | O | 0 | \ J* °=<2j Z O \=o O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.50 (s, 2H), 7.88-7.86 (m, 4H), 6.60 (s, 2H), 4.86-4.77 (m,2H), 4.39 — 4.31 (m,4H), 3.42 (s, 6H), 1.41 (d,7=7.0 Hz,6H). |
452 | <Τ Ο —Ζ \=ο | CH(Me) | O | O | |-NH OH | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.49 (s, 1H), 7.94 (d, 7= 8.0 Hz, 1H), 7.88 (d, 7=9.5 Hz, 1H), 6.61 (s, 1H), 4.62 (q, 7= 7.0 Hz, 1H), 3.45 -3.40 (m, 4H), 1.40 (d, 7= 7.0 Hz, 3H). |
453 | J Ο —Z \=o oA. | CH(Me) | O | o | -1Νγ ό | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.59 (s, 1H), 8.00-7.85 (m, 2H), 7.78-7.76(m, 2H), 7.53-7.51 (m, 3H), 6.59 (s, 1H), 5.14 (q,J= 7.0 Hz, 1 H), 3.41 (s, 3H), 2.38 s, 3H), 1.61 (d, J= 7.0 Hz, 3H). |
454 | o=< z— 1 o CO LL· | CH(Me) | o | o | po | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.50 (s, 1H), 7.92 (d,J= 7.5 Hz, 1H), 7.88 (d, J = 9.5 Hz, 1 H), 6.62 (s, 1H), 5.20 (q, J =6.5 Hz, 1H), 3.593.52 (m, 6H), 3.53-3.48 (m, 1H), 3.47-3.44 (m, 1H), 3.43 (s, 3H), 1.41 (d, J= 6.5 Hz, 3H). |
455 | J1 o —Z /=O fa | CH^ | o | o | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-c/6) δ 8.53 (s, 1H), 7.93 (d, J= 8.0Hz, 1H), 7.88 (d, .7=9.5 Hz, 1H), 6.62 (s, 1 H), 4.80-4.77 (m, 1H), 3.70 (s, 3H), 3.43 (s, 3H), 1.80-1.70 (m, 2H), 1.66-1.60 (m, 1H), 0.95 (d, J= 6.5 Hz, 6H). |
456 | fa° o=< Z— o LL | l | o | o | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO-A) δ 8.54 (s, 1H), 7.97-7.85 (m, 2H), 6.61 (s, 1H), 4.18 (d, J= 9.0 Hz, 1H), 3.71 (s, 3H), 3.42 (s, 3H), 1.26-1.21 (m, 1H), 0.66-0.63 (m, 2H), 0.58-0.49 (m, 2H). |
457 | cl· O —Z )=O ofa | CH | o | o | OMe | Cl | F | CH | |
458 | cl· O —Z ofa | 'Ύ CH | o | o | OMe | Cl | F | CH | |
459 | O=< Z— o IL | ^H | o | o | OMe | Cl | F | CH |
460 | Ο îV f3c^n^o | O | O | OMe | Cl | F | CH | ||
461 | A o=< z— o d? | Y CH | O | o | OMe | Cl | F | CH | |
462 | 0 Af F3AljY0 | CH^ | O | o | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSOY) δ 8.54 (s, 1H), 8.03-7.83 (m, 2H), 6.61 (s, 1H), 4.85-4.82 (m, 1H), 3.70 (s, 3H), 3.43 (s, 3H), 1.88-1.82 (m, 1H), 1.70-1.65 (m, 1H), 0.93-0.80 (m, 1H), 0.47-0.43 (m, 2H), 0.16-0.11 (m, 2H). |
463 | J o —Z Ao oA _ | CH | O | o | OMe | Cl | F | CH | 1H NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.94-7.86 (m, 2H), 6.61 (d,J= 2.0 Hz, 1H), 4.98-4.88 (m, 1H), 4.76-4.48 (m, 2H), 3.48 (s, 3H), 3.43 (s, 3 H). |
464 | o=< z— o LL | r5 CH | O | o | OMe | Cl | F | CH | |
465 | A° o=< z— o LL | ^CF3 CH | O | o | OMe | Cl | F | CH | |
466 | A° O=\ z— o d? | ^OH CH | O | o | OMe | Cl | F | CH | |
467 | o=< z— o LL | CH(SMe) | O | o | OMe | Cl | F | CH | |
468 | 0 îV f3c^n^o | 'Ά 1 CH | O | o | OMe | Cl | F | CH | |
469 | A° o=< z— o LL | CH | O | o | OMe | Cl | F | CH | 1H NMR (500 MHz, DMSO) δ 8.55 (s, 1H), 7.95-7.83 (m, 2H), 7.36-7.30 (m, 3H), 7.287.22 (m, 2H), |
6.61 (d, 7=2.0 Hz, 1H), 4.294.23 (m, 1H), 3.48 (s, 3H), 3.43 (s, 3H), 2.76-2.73 (m, 2H). | |||||||||
470 | JA o=< z— O IL· | C(F)2 | O | O | OEt | Cl | F | CH | |
471 | J1 O —Z \=o | C(Me)(Et) | O | O | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.48 (s, 1 H), 7.89-7.87 (m, 2H), 6.63 (s, 1H), 3.69 (s, 3H), 3.43 (s, 3H), 1.89-1.87 (m,2H), 1.531.49 (m, 3H), 0.89 (t, 7= 7.5 Hz, 3H). |
472 | <? O —Z \=o fa | Me C | O | O | OMe | Cl | F | CH | |
473 | O F3c^y% | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 7.98 (d, 7= 7.5 Hz, 1H), 7.90 (d, 7=9.5 Hz, 1H), 4.89 (q, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 3.43 (s, 3H), 2.28 (s, 3 H),1.47 (d,7= 7.0 Hz, 3H). |
474 | 0 f3cy^° F | CH(Me) | O | O | OMe | Cl | F | CH | |
475 | O -ναλ FsryS) Br | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfj) δ 8.52 (s, 1H), 8.20 (d, 7= 8.0 Hz, 1 H), 7.96- 7.91 (m, 1H), 4.89 (q, 7= 7.0 Hz, 1H), 3.70 (s, 3H), 3.49 (s, 3H), 1.47 (d, 7= 7.0 Hz, 3H). |
476 | 0 f3c'^Y^° 1 | CH(Me) | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-rfi) δ 8.52 (s, 1H), 7.91 (d, 7=8.0 Hz, 1H), 7.88 (d, 7=9.5 Hz, 1 H), 4.89 (q, 7 =7.0 Hz, 1H), 3.70 (s, 3H), 3.46 (s, 3 H), 1.48 (d,7= 7.0 Hz, 3H). |
477 | / ο CO LL | CH(Me) | O | O | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO) δ 8.51 (s, 1H), 7.91-7.89 (m, 2H), 4.90 (q, 7= 7.0 Hz, 1 H), 3.72-3.70 (m, 6H), 3.39 (s, 3H), 1.47(d,7= 7.0 Hz, 3H). |
478 | Z /° AA / O LL· | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO) δ 8.51 (s, 1H), 7.85-7.83 (m, 2H), 4.94-4.81 (m, 3H), 4.29 - 4.21 (m,2H), 4.20-4.06 (m, 2H), 3.62-3.60 (m, 2H), 2.99 (s, 3H), 1.49(d, 7= 8.0 Hz, 3H). | |
479 | o=< z— O LL· | CH2CH2 | 0 | 0 | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO-de) δ 8.42 (s, 1H), 7.99 (d, 7= 8.0 Hz, 1H), 7.86 (d, 7=9.5 Hz, 1H), 6.62 (s, 1 H), 4.39 (t, 7= 6.0 Hz, 2H), 3.63 (s, 3H), 3.43 (s, 3H), 2.77 (t,7= 6.0 Hz, 2H). |
480 | o=( Z— O IL· | CH2CH2 | O | 0 | OEt | Cl | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.42 (s, 1H), 7.99 (d, 7= 8.0 Hz, 1H), 7.86 (d, 7= 9.5 Hz, 1 H), 6.62 (s, 1H), 4.39 (t, 7= 6.0 Hz, 2H), 4.10 (q, 7= 7.0 Hz, 2H), 3.44 (s, 3H), 2.75 (t, 7= 6.0 Hz,2H), 1.19 (t, 7= 7.0 Hz, 3H). |
481 | ω1 O —Z \=o | CH(Me)CH2 | O | O | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO-ds) δ 8.39 (s, 1H), 7.99 (d, 7= 8.0 Hz, 1H), 7.85 (d, 7=9.5 Hz, 1 H), 6.62 (s, 1H), 4.67 (q, 7 =6.5 Hz, 1H), 3.62 (s, 3H), 3.44 (s, 3H), 2.78-2.63 (m, 2H), 1.33 (d, 7= 6.5 Hz, 3H). |
482 | K O=< Z— O d? | CH2CH(Me) | O | O | OMe | Cl | F | CH | |
483 | J1 O —z \=o | CH(Me)CH2 ch2 | O | O | OMe | Cl | F | CH |
484 | A° O=< Z— O IL | CH(Me)CH2 CH2CH2 | 0 | 0 | OMe | Cl | F | CH | |
485 | A O=< Z— O if? | CH2CH2CH2 | 0 | 0 | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.40 (s, 1H), 7.96 (d, J= 8.0 Hz, 1H), 7.83 (d, 7=9.5 Hz, 1H), 6.59 (s, 1H), 4.16 (t,7= 7.0Hz, 2H), 3.58 (s, 3H), 3.41 (s, 3H), 2.41 (t,7= 7.0 Hz, 2H), 1.95-1.89 (m, 2H). |
486 | A O=< Z— O LL | ^cf3 CH | 0 | 0 | OEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-<4) δ 8.58 (s, 1H), 8.02-7.88 (m, 2H), 6.63 (s, 1 H), 5.26-5.20 (m, 1H), 4.13 (d, 7 = 7.0,2H), 3.43 (s, 3H), 3.06 - 2.88 (m, 2H), 1.19 (d, 7= 7.0,3H). |
487 | J1 O —Z Ao □A | CH | 0 | 0 | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.59 (s, 1 H), 8.56 (s, 1H), 7.97 - 7.87 (m, 3H), 6.61 (d,7= 2.5 Hz, 2H), 5.01-4.98 (m, 1 H), 4.49 (d, 7= 5.0 Hz, 1H), 4.24-4.20 (m, 1H), 3.72 (s, 3H), 3.40 (s, 3H). |
488 | J1 O —Z Ao □A | <Ih | 0 | 0 | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.54 (s, 1 H), 7.96-7.85 (m, 2H), 6.61 (s, 1 H), 4.73 (d, 7= 7.5Hz, 1 H), 3.68 (s, 3H), 3.43 (s, 3H), 2.78-2.74 (m, 1H), 2.11-2.01 (m, 4H), 1.95-1.80 (m,2H). |
489 | A° O=< z— O LL | 9 CH | 0 | 0 | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO-76) δ 8.52 (s, 1H), 7.98-7.82 (m, 2H), 6.61 (s, 1 H), 4.61 (dd,7 = 7.5,3.0 Hz, 1H), 3.70 (s, 3H), 3.42 (s, 3H), 2.33-2.29 (m, 1H), 1.871.30 (m,8H). |
490 | A° o=< z— O IL | O | O | OMe | CI | F | CH | Ή NMR (500 MHz, DMSO-c/s) δ 8.51 (s, 1H), 7.98-7.78 (m, 2H), 6.59 (s, 1 H), 4.56-4.54 (m, 1 H), 3.67 (a, 3H), 3.40 (s, 3H), 1.90-1.53 (m, 6H), 1.25-1.14 (m, 5H) | |
491 | O S^N^O | CH(Me) | O | 0 | SEt | Cl | F | CH | ‘H NMR (500 MHz, DMSO-</6) δ 8.58 (s, 1 H), 8.06 (d,J= 8.0 Hz, 1 H), 7.91 (d, ./=9.0 Hz, 1H), 4.94 (q,J= 6.5 Hz, 1H), 3.63 (s, 6H), 2.89-2.82 (m, 2H), 1.46 (d, 7=6.5 Hz, 3H), 1.18 (t,./=7.5 Hz, 3H). |
492 | . A , °A z— O IL | CH(Me) | O | O | Cl | F | CH | ‘H NMR (500 MHz, DMSO-dt) δ 8.55 (s, 1H), 7.94 (d, 7= 8.0 Hz, 1H), 7.89 (d, J = 9.5 Hz, 1 H), 6.60 (s, 1H), 5.03 (q, 7= 7.0 Hz, 1H), 3.42 (s, 3H), 1.92 (s, 3H), 1.54 (d, 7= 7.0 Hz, 3H), 1.14 (s, 9H). | |
493 | °fe O )—O CO / ILO=Ç O / | CH(OMe) | O | O | OMe | Cl | F | CH | Ή NMR (500 MHz, DMSO-<4>) δ 8.63 (s, 1H), 8.02 (d,7= 7.5 Hz, 1 H), 7.91 (d, J = 9.5Hz, 1H), 6.86-6.75 (m, 1H), 5.84 (s, 1H), 5.70 (s, 1H), 3.76 (s, 3H), 3.68 (s, 3H), 3.53 (s, 3H), 3.47 (s, 3H). |
494 | J1 O —Z Ao ofa | C(0Me)2 | O | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-c/s) δ 8.57 (s, 1H), 7.92 (d, 7= 7.5 Hz, 1H), 7.88 (d, J = 9.5 Hz, 1 H), 6.61 (s, 1H), 4.82-4.81 (m, 1H), 4.71 (d,7= 5.5 Hz, 1H), 3.72-3.71 (m, 3H), 3.43 (s, 3H), 3.39 (s, 3H), 3.38 (s, 3H). |
495 | Ο Λ f3c n^o | CH(Me) | O | o | /'O^Y^N 1 JT | Cl | F | CH | 1HNMR (500 MHz, DMSO-d6) δ 8.56 (s, IH), 8.04 (s, IH), 7.84 (d,J = 6.0 Hz, IH), 7.46-7.25 (m, 3H), 6.43 (s, IH), 5.23 (s, 2H), 4.53 (q, J = 7.0 Hz, 1 H), 3.43 (s, 3H), 1.45 (d, J = 7.0 Hz,3H). |
496 | o /a f3ctn^o | ^OH CH | O | o | OMe | Cl | F | CH | IH NMR (500 MHz, DMSO) δ 8.52 (s, IH), 7.96-7.87 (m, 2H), 6.61 (d,7= 2.0 Hz, IH), 4.29 -4.23 (m, IH), 3.48 (s, 3H), 3.43 (s, 3H), 3.29-3.28 (m, 2H), 1.89-1.82 (m, 2H). |
497 | J1 o —Z \=o | ^Cl CH | O | o | OMe | Cl | F | CH | IH NMR (500 MHz, DMSO) δ 8.50 (s, IH), 7.91-7.84 (m, 2H), 6.61 (d, 7= 2.0 Hz, IH), 4.29 -4.23 (m, IH), 3.48 (s, 3H), 3.43 (s, 3H), 3.09-2.96 (m, 2H), 1.84- 1.77 (m,2H). |
498 | 0 f3c n o | CH(Me) | o | o | ofa r | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.52 (s, IH), 7.94-7.86 (m, 2H), 6.61 (s, IH), 4.88-4.84 (m, 2H), 4.29 — 4.23 (m, 1 H), 4.19-4.13 (m, IH), 3.89-3.83 (m, 2H), 3.74- 3.70 (m, 2H), 3.43 (s, 3H), 1.94-1.89 (m, 2H), 1.47 (d, 7= 7.0 Hz, 3H). |
499 | fa o={ z— o LL? | CH(Me) | o | o | NH2 | Cl | F | CH | ‘H NMR (500 MHz, DMSO-A) δ 8.52 (s, IH), 7.97 (d, 7= 7.0 Hz, IH), 7.87 (d, 7=9.5 Hz, IH), 7.40 (s, IH), 4.58 (q, 7=7.0 Hz, IH), 3.42 (s, 3H), 1.40 (d, 7= 7.0 Hz, 3H). |
500 | fa O=< Z— o LL? | CH(Me) | 0 | o | ^-o Cl | Cl | F | CH | ‘H NMR (500 MHz, DMSO-76) δ 8.50 (s, IH), 7.94 - 7.79 (m, 2H), 6.59 (s, IH), 5.90-5.73 |
(m, 1 H), 4.944.82 (m, 1H), 4.76 - 4.62 (m, 2H), 3.40 (s, 3H), 2.10 (s, 3H), 1.45 (d,J= 7.0 Ha 3 H). | |||||||||
501 | 0 iV F3O'N'X> | CH(Me) | O | O | l-o ci A | Cl | F | CH | Ή NMR (500 MHa DMSO-</6) δ 8.51 (s, 1H), 7.94-7.84 (m, 2H), 6.59 (a 1 H), 5.64-5.63 (m, 1H), 5.48-4.45 (m, lH),4.95(q, J= 7.0 Ha 2H), 4.84-4.73(m, 1H), 3.97-3.96 (m, 1H), 3.40 (s, 3H), 1.49 (d,J= 7.0 Ha 3H). |
502 | <? O —z Ao □A | CH(Me) | O | O | y | Cl | F | CH | Ή NMR (500 MHa DMSO-rf6) δ 8.46 (s, 1H), 7.98 - 7.79 (m, 2H), 6.59 (s, 1H), 5.12 (q,J= 7.0 Ha 1H), 3.41 (s, 3H), 3.403.34 (m, 2H), 3.21 (m,2H), 1.37 (d, .7=7.0 Ha3H), 1.12 (t, J=7.0Ha3H), 1.00 (t,J= 7.0 Ha 3H). |
503 | J O —Z Z=O □A | CH(Me) | O | O | S H * sAci h O | Cl | F | CH | ‘H NMR (500 MHa DMSO-<4) δ 8.38 (s, 1H), 7.92 (d,J= 8.0 Ha 1H), 7.82 (d, .7=9.5 Ha 1H), 6.57 (s, 1H), 4.61-4.58 (m, 2H), 4.49-4.45(m,l H), 3.40 (s, 3H), 1.33 (d, .7=7.0 Ha 3H). |
504 | TA oA z— O LL | CH(Me) | O | O | OMe | Cl | F | N | *H NMR (500 MHa DMSO) δ 8.59-8.57 (m, 2H), 6.65 (s, 1 H), 4.96-4.92 (m, 1H), 3.70 (s, 3H),3.44(s,3H), 1.28 (d,J= 7.0 Ha3H) |
505 | s FaC^A | CH(Me) | O | O | OMe | Cl | F | N | |
506 | J1 °\ / ^A CO r’X | CH(Me) | O | O | OMe | Cl | F | N |
507 | S F3cAAs | CH(Me) | O | O | OMe | CI | F | N | |
508 | 0 iY F3C Nx) | CH(Me) | O | O | OMe | Br | F | N | |
509 | ω1 O —Z )=o oA | CH(Me) | O | O | OMe | CF3 | F | N | |
510 | JA O=K/ZO UL? | CH(Me) | O | O | OMe | CN | F | N | |
511 | XT At ' <n | CH(Me) | O | O | OMe | Cl | F | N | ‘H NMR (500 MHz, DMSO-76) δ 7.85 (s, 1H), 7.70 (d, 7= 8.0 Hz, 1H), 4.53 (q, 7=7.0 Hz, 1 H), 3.73 (d, 7= 6.0 Hz, 9H), 1.41 (d, 7= 7.0 Hz, 3H). |
512 | 0 T^rA SANAS 1 | CH(Me) | O | O | OMe | Cl | F | N | |
513 | û ^rArA oA'n-Aq 1 | CH(Me) | O | O | OMe | Cl | F | N | |
514 | JT At ' tn | CH(Me) | O | O | OMe | Br | F | N | |
515 | ω / -z >o oT | CH(Me) | O | O | OMe | cf3 | F | N | |
516 | O ^N^lA S^N^O . 1 | CH(Me) | O | O | OMe | CN | F | N | |
517 | ω / K -Z >O □A | CH(Me) | O | s | OEt | Cl | F | N | |
518 | At ' to | CH(Me) | O | O | Cl | F | N |
519 | / -Z >O | CH(Me) | O | O | 0^ | Cl | F | N | |
520 | O S^N^O 1 | CH(Me) | O | O | Cl | F | N | ||
521 | ω / H -Z >O | CH(Me) | O | O | ho | Cl | F | N | |
522 | O S^N^O 1 | CH(Me) | O | 0 | Cl | F | N | ||
523 | ω / H -Z >o | CH(Me) | O | 0 | ho | Cl | F | N | |
524 | ω / -Z >O | CH(Me) | O | O | ho ^cf3 | Cl | F | N | |
525 | ' U) | CH(Me) | O | O | ho 0^ | Cl | F | N | |
526 | ω / >-< -Z >O | CH(Me) | O | O | o | Cl | F | N | |
527 | ω / H -Z >O | CH(Me) | O | O | ho N | Cl | F | N | |
528 | 0 S^N^O 1 | CH(Me) | O | O | ho h^O^ | Cl | F | N | |
529 | Jh° °1k~ z ω | CH(Me) | O | O | ho | Cl | F | N | |
530 | ω / H -Z >O | CH(Me) | O | O | ho • | Cl | F | N | |
531 | ω , -z >0 | CH(Me) | 0 | O | ho V? | CI | F | N |
532 | JA 7 ω | CH(Me) | O | 0 | /O | Cl | F | N | |
533 | ω / H -z >o | CH(F) | O | o | OEt | Cl | F | N | |
534 | 5a_ 7 G) | CH(Et) | O | o | OMe | Cl | F | N | |
535 | O S^N^O 1 | C1H | o | o | OEt | Cl | F | N | |
536 | ô vA S^N^O 1 | ^CH | o | o | OMe | Cl | F | N | |
537 | o 1 | Y CH | o | o | OEt | Cl | F | N | |
538 | ω / H -Z >O | ς CH | o | o | OEt | Cl | F | N | |
539 | ω / H -z >o | 1 °A CH | o | 0 | OMe | Cl | F | N | |
540 | ts P o=< /z 7 ω | CH(Me) | o | o | OEt | Br | F | N | |
541 | ω / K -z >O | CH(Me) | o | 0 | OEt | cf3 | F | N | |
542 | JA °AA~ 7 ω | CH(Me) | o | o | OEt | CN | F | N | |
543 | w / -zKo ω | CH(Me) | o | o | OEt | Br | F | N | |
544 | 0 ^nA|A· 1 | CH(Me) | o | o | SEt | Cl | F | N |
545 | Ô S^N^O 1 | CH(Me) | O | O | / / ° -^NH | Cl | F | N | |
546 | ω , A -Z >O fa | C(Me)i | O | O | OMe | Cl | F | N | |
547 | fa O=< Z— O LL? | CH(Me) | O | 0 | OH | Cl | F | N | |
548 | fa O=< Z— O LL? | CH(Me) | O | O | OEl | Cl | F | N | |
549 | J1 O —Z >o fa | CH(Me) | O | O | 7’0^ | Cl | F | N | |
550 | J O —Z A° Aa O | CH(Me) | O | O | Cl | F | N | ||
551 | A z— O LL? | CH(Me) | O | O | Cl | F | N | ||
552 | fa o=C z— o LL? | CH(Me) | O | O | Cl | F | N | ||
553 | J O —z Ao fa | CH(Me) | O | O | Cl | F | N | ||
554 | J O —z Ao fa | CH(Me) | O | O | Cl | F | N | ||
555 | fa o=< z— O LL? | CH(Me) | O | O | Cl | F | N | ||
556 | A° O=< z— O LL? | CH(Me) | O | O | Cl | F | N | ||
557 | 0 λν\ FsC^N^O | CH(Me) | O | O | Cl | F | N |
558 | οχ Z— ο IX? | CH(Me) | O | o | Cl | F | N | ||
559 | χ° οχ ζ— ο tx? | CH(Me) | O | o | Cl | F | N | ||
560 | 1 I χ° οχ ζ— ο ιΤ | CH(Me) | O | 0 | Cl | F | N | ||
561 | Ô iV f3c ν^ο | CH(Me) | O | o | Ao | Cl | F | N | |
562 | JA οχ Ζ— ο tx | CH(Me) | O | o | Χ-°χ\ | Cl | F | N | |
563 | οχ Ζ— ο IX | CH(Me) | o | o | CI | F | N | ||
564 | κ οχ ζ— ο IX | CH(Me) | o | 0 | F \.°XF | Cl | F | N | |
565 | ω1 Ω —Ζ \=ο | CH(Me) | o | o | .^O^/CF3 | Cl | F | N | |
566 | ω1 Ο —Ζ \=ο | CH(Me) | o | o | F\ F ^O^XX | Cl | F | N | |
567 | JA οχ ζ— ο IX | CH(Me) | o | o | -¾ o J1 | Cl | F | N | |
568 | J1 Ο —ζ )=ο | CH(Me) | o | o | Cl | F | N | ||
569 | ω1 Ο —Ζ \=Ο | CH(Me) | o | o | ^CX/CN | Cl | F | N | |
570 | J1 ο —ζ \=ο | CH(Me) | o | o | \°^^CN | Cl | F | N |
100
571 | x° O=< Z— o IL | CH(Me) | O | O | C1 | F | N | ||
572 | J o —Z Xo oX | CH(Me) | O | O | /O | C1 | F | N | |
573 | J1 o —z Xo oX | CH(Me) | O | O | Ao °~Λ | C1 | F | N | |
574 | J1 o —Z \=o oX | CH(Me) | O | O | C1 | F | N | ||
575 | <T o —z Xo oX | CH(Me) | O | o | /ό \ | C1 | F | N | |
576 | <? o —z \=o □X | CH(Me) | O | o | C1 | F | N | ||
577 | x° o=< z— o LL | CH(Me) | O | o | ο >° | C1 | F | N | |
578 | J1 o —z \=o oX | CH(Me) | O | o | o | C1 | F | N | |
579 | o=< z— o LL | CH(Me) | O | o | 0 | C1 | F | N | |
580 | J1 o —z Xo oX | CH(Me) | O | o | 0 | C1 | F | N | |
581 | J1 o —z \=o oX | CH(Me) | O | o | 0 Α°γν | C1 | F | N | |
582 | 0 jrV F3C'^N^O | CH(Me) | O | o | ο Χθ^ο- | C1 | F | N | |
583 | J1 o —Z V=O oX | CH(Me) | O | o | \ /° ° \ )=° °\ | C1 | F | N |
101
584 | 0 rV f3c Ao | CH(Me) | O | o | o o | Cl | F | N | |
585 | 0 iV fAAo | CH(Me) | O | o | A-q | Cl | F | N | |
586 | o=< Z— o LL? | CH(Me) | O | o | Cl | F | N | ||
587 | J O —Z Ao □A | CH(Me) | O | o | Cl | F | N | ||
588 | jA o=4 z— o IL? | CH(Me) | O | o | -V°'nA | Cl | F | N | |
589 | A 0=4 z— o d? | CH(Me) | O | 0 | Cl | F | N | ||
590 | ω1 O —z y=o .A | CH(Me) | O | o | Άι t z o | Cl | F | N | |
591 | A o=4 z— o LL? | CH(Me) | 0 | o | V^N^COzEt | Cl | F | N | |
592 | 0 rV f3c n^o | CH(Me) | o | o | Cl | F | N | ||
593 | J1 o —z \=o | CH(Me) | o | o | /'0 | Cl | F | N | |
594 | j>4° o=X z— o LL? | CH(Me) | o | o | o z Λ | Cl | F | N | |
595 | ω1 O —Z \=O | CH(Me) | o | o | Cl | F | N | ||
596 | J1 o —z \=o □A | CH(Me) | 0 | o | ο | Cl | F | N |
102
597 | ω1 Ο —ζ )=ο fa | CH(Me) | O | o | /0 | Cl | F | N | |
598 | ja° ο=/ ζ— ο IX? | CH(Me) | O | o | X) $-0 o\ | Cl | F | N | |
599 | JA° ο=< ζ— ο d? | CH(Me) | 0 | o | ω A θ'7 | Cl | F | N | |
600 | J1 ο —ζ \=ο fa* | CH(Me) | 0 | o | /O | Cl | F | N | |
601 | ÛP ο —Ζ /=Ο fa* | CH(Me) | o | o | A° K aX | Cl | F | N | |
602 | ω1 ο —ζ \=ο fa | CH(Me) | o | o | F | Cl | F | N | |
603 | ω1 Ο —Ζ \=ο | CH(Me) | o | o | F | Cl | F | N | |
604 | <? ο —ζ )=ο | CH(Me) | o | o | / Z XJ/ | Cl | F | N | |
605 | ω1 Ο —Ζ \=Ο fa | CH(Me) | o | o | /O V? | Cl | F | N | |
606 | fa Ο=< ζ— ο ιί? | CH(Me) | o | o | /O | Cl | F | N | |
607 | Ο —ζ \=ο fa* | CH(F) | o | o | OEt | Cl | F | N | |
608 | 0 Χύ f3c ν ο | CH(Et) | o | o | OMe | Cl | F | N | |
609 | ο —Ζ /=Ο fa | CH | o | 0 | OMe | Cl | F | N |
103
610 | oj z— O d? | Xh | O | O | OMe | Cl | F | N | |
611 | J1 O —z Ao □A | Y CH | O | 0 | OEl | Cl | F | N | |
612 | o=< Z— ü LL | CH(OMe) | O | 0 | OMe | Cl | F | N | |
613 | oj z— O LL | CH(OMe) | O | 0 | OEl | Cl | F | N | |
614 | ω1 O —Z A° □A | CH(OMe) | O | O | Cl | F | N | ||
615 | A° o=< z— O d? | CH(OMe) | O | O | Cl | F | N | ||
616 | A° o=Y z— O LL | CH(OMe) | O | O | ^0 ^cf3 | Cl | F | N | |
617 | J O —z Ao □A | CH(OMe) | O | O | ko | Cl | F | N | |
618 | 0 Aa f3c n^o | ς CH | 0 | 0 | OMe | Cl | F | N | |
619 | JA o=< z— O LL | 1 CH | O | O | OMe | Cl | F | N | |
620 | 0 Aû f3c nA) | CH(Ph) | O | O | OMe | Cl | F | N | |
621 | J1 ω | CH(Me) | O | 0 | OMe | Br | F | N | |
622 | « / b <*3 LL | CH(Me) | O | O | OMe | CN | F | N |
104
623 | / b LL | CH(Me) | O | O | OMe | Βγ | F | N | |
624 | S f3c-^^s | CH(Me) | O | O | OMe | cf3 | F | N | |
625 | ω1 fi ω | CH(Me) | O | O | OMe | CN | F | N | |
626 | / O if | CH(Me) | 0 | O | OMe | Br | F | N | |
627 | S FsC^^O | CH(Me) | O | O | OMe | CF3 | F | N | |
628 | S xn^nV FsC^^O | CH(Me) | O | O | OMe | CN | F | N | |
629 | J1 O —z )=o oV | CH(Me) | O | O | SEt | Cl | F | N | |
630 | J1 O —Z /=O oV | CH(Me) | O | O | Cl | F | N | ||
631 | 0=< Z— O LL | CH(Me) | O | O | νγ | Cl | F | N | |
632 | <7 o —Z \=O | CH(Me) | 0 | O | ο— rA ° | Cl | F | N | |
633 | v° o=< z— O IL | CH(Me) | O | O | Cl | F | N | ||
634 | JK o=< z— O IL | CH(Me) | O | O | / / ° ήΝΗ | Cl | F | N | |
635 | v° z— O IL | CH (Me) | O | O | '''ζ— / Ο | Cl | F | N | |
636 | J1 O —z \=o d X | CH(Me) | O | 0 | ο V ζ II X ° | Cl | F | N |
105
637 | ω1 Ο —ζ Αο □Α | CH(Me) | O | O | Cl | F | N | |||
638 | 1 Ο f3c^^o | CH(Me) | O | O | OMe | Cl | F | N | ||
639 | f3< | Α° ο=Α — / | CH(Me) | O | O | OMe | Cl | F | N | |
640 | Ό FsC^y^0 Cl | CH(Me) | O | O | OMe | Cl | F | N | ||
641 | Η ο -Ρ1 CO X LL | CH(Me) | O | o | OMe | Cl | F | N | ||
642 | Α° ο=ς ζ— ο LU | C(Me)2 | O | o | OMe | Cl | F | N | ||
643 | J1 Ο —ζ Αο οΑ | C(Me)2 | O | o | Cl | F | N | |||
644 | 0 sAnA0 1 | CH(Me) | O | 0 | OH | Cl | F | N | ||
645 | ω / A -Ζ >Ο ΟΑ | CH(Me) | O | o | ’/o '~'CF3 | Cl | F | N | ||
646 | <τ ο —ζ Αο □Α | CH(Me) | O | o | Cl | F | N | |||
647 | <? ο —ζ Αο □A | CH(Me) | O | o | vV CN | Cl | F | N | ||
648 | Α° ο=< ζ— ο LU | CH(Me) | O | o | λ'°^ΆΝ | Cl | F | N | ||
649 | <? Ο —Ζ Αο □A | CH(Me) | O | 0 | Cl | F | N |
106
650 | o=Y z— O d? | CH(Me) | O | O | X'O^-^CN | Cl | F | N | |
651 | <7 O —z A° □A | CH(Me) | O | O | Cl | F | N | ||
652 | J1 O —Z A° □A | CH(Me) | O | O | Cl | F | N | ||
653 | J1 O —z \=o □A | CH(Me) | O | O | Cl | F | N | ||
654 | J1 O —z \=o oA | CH(Me) | O | O | /0 | Cl | F | N | • |
655 | J1 O —z A° □A | CH(Me) | O | O | /0^°γΑΝΑΑΝΑΝχ ° tAA | Cl | F | N | |
656 | <7 O —z Ao □A | CH(Me) | O | O | |-NH OH | Cl | F | N | |
657 | J1 O —z Ao □A | CH(Me) | 0 | O | Χ·Νγ ô | Cl | F | N | |
658 | J1 O —z Ao □A | CH(Me) | O | O | po ,ΧςΝχΑ | Cl | F | N | |
659 | tJ1 O —z Ao oA i | CH^ | O | O | OMe | Cl | F | N | |
660 | o=Y Z— O IL | Y CH | O | O | OMe | Cl | F | N | |
661 | A o=< z— O IL | CH^ | 0 | O | OMe | Cl | F | N | |
662 | A o=< z— O IL | ^F CH | O | 0 | OMe | Cl | F | N |
107
663 | ω1 Ο —Ζ \=Ο | O —\ X \—O | O | O | OMe | Cl | F | N | |
664 | ο=< ζ— ο IL· | C(Me)(Et) | O | O | OMe | CI | F | N | |
665 | 0 f3c'AV'% | CH(Me) | O | O | OMe | Cl | F | N | |
666 | 0 f3^y>° Br | CH(Me) | O | 0 | OMe | Cl | F | N | |
667 | ϋ FsC^^Y^O 1 | CH(Me) | O | O | OMe | Cl | F | N | |
668 | Ô '''bA^rA FaC^y^O /° | CH(Me) | O | O | OMe | Cl | F | N | |
669 | Ô ^N^bA f3c-^A^o OH | CH(Me) | O | O | Cl | F | N | ||
670 | o=< z— o LL· | CH2CH2 | O | O | OMe | Cl | F | N | |
671 | J1 O —z Ao fa | ch2ch2 | O | O | OEt | Cl | F | N | |
672 | o=< z— O LL· | CH(Me)CH2 | O | O | OMe | Cl | F | N | |
673 | o=< z— o d? | CH2CH2CH2 | 0 | O | OMe | Cl | F | N | |
674 | J O —Z /=O | ^CFa CH | O | O | OEt | Cl | F | N |
108
675 | fa □=< ζ— ο LL | ? CH | O | O | OMe | Cl | F | N | |
676 | cJ1 Ο —ζ \=ο | 9 CH | O | 0 | OMe | Cl | F | N | |
677 | fa ο=ς ζ— ο LL | 9 CH | O | O | OMe | Cl | F | N | |
678 | κ ο=< ζ— ο IL | O | 0 | OMe | Cl | F | N | ||
679 | ο '''Ν'^ΐΑ S^N^O 1 | CH(Me) | O | O | SEt | Cl | F | N | |
680 | ο χΥ f3c^n^o | CH(Me) | O | O | Cl | F | N | ||
681 | 0 | CH(OMe) | O | 0 | OMe | Cl | F | N | |
682 | ω1 Ο —Ζ /=Ο fa | C(0Me)2 | O | O | OMe | Cl | F | N | |
683 | J1 ο —Ζ \=Ο fa | CH(Me) | O | O | Y | Cl | F | N | |
684 | ο ιΥ f3c n^o | ['''OH CH | O | 0 | OMe | Cl | F | N | |
685 | <? ο —ζ \=ο fa | ^Cl CH | O | O | OMe | Cl | F | N | |
686 | Jfa Ο=< ζ— ο IL | CH(Me) | O | O | θΎ r | Cl | F | N | |
687 | J1 ' Ο —ζ Αο fa | CH(Me) | O | O | nh2 | Cl | F | N |
109
688 | JP Ο —Z /=O fa | CH(Me) | O | O | |-o cr | Cl | F | N | |
689 | fa o=< z— O IL· | CH(Me) | O | O | |-οχ | Cl | F | N | |
690 | fa o=< z— O IL· | CH(Me) | 0 | O | U | Cl | F | N | |
691 | JP O —z \=o fa | CH(Me) | O | O | s H '^'N'S<3-CI H O | Cl | F | N | |
692 | O n^A S^N^O | CH(Me) | S | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMS0-<4) δ 7.96 (d, J= 1.0Hz, 1 H), 7.22 (d,J=8.0Hz, 1H), 7.12 (d, J= 9.0 Hz, 1H), 3.75 (s, 6H), 3.66 (s, 3H), 3.47 (q, J= 7.0 Hz, 1H), 1.56 (d, 7= 7.0 Hz, 3H). |
693 | O n^A S^N^O 1 | CH(Me) | S | 0 | OEt | CI | F | CH | |
694 | o n^A S^N^O 1 | CH(Me) | s | s | OEt | Cl | F | CH | |
695 | O S^N^O 1 | CH(Me) | s | O | 7'0^ | Cl | F | CH | |
696 | ω , fa >=° fa | CH(Me) | s | O | <A | Cl | F | CH | |
697 | ω / fa >=° fa | CH(Me) | s | O | Cl | F | CH | ||
698 | ω / fa -Z >O fa | CH(Me) | s | O | Ao | Cl | F | CH | |
699 | u> / fa\a fa | CH(Me) | s | O | ^°^F | Cl | F | CH |
110
700 | ω / A -Z >O □A | CH(Me) | S | O | -/-O 'F | Cl | F | CH | |
701 | ω , -zHo □A | CH(Me) | S | O | /'O Acf3 | Cl | F | CH | |
702 | ω , A -Z >O □A | CH(Me) | s | O | Ao o^. | Cl | F | CH | |
703 | O sKNXo 1 | CH(Me) | s | O | O ,\<aA0^ | Cl | F | CH | |
704 | ω / K □A | CH(Me) | s | O | /O | Cl | F | CH | |
705 | ω > A -Z >O □A | CH(Me) | s | O | Ao | Cl | F | CH | |
706 | ω / A -z >0 □A | CH(Me) | s | O | A o \ Ck V? | Cl | F | CH | |
707 | ω , A -Z >O oA | CH(Me) | s | O | Ao | Cl | F | CH | |
708 | ω / A -Z >O □A | CH(Me) | s | O | /'O A/^N a9 | Cl | F | CH | |
709 | ω / A -z >0 □A | CH(Me) | s | O | Ao | Cl | F | CH | |
710 | J-Λ °1a ' ω | CH(F) | s | O | OEt | Cl | F | CH | |
711 | ω , y-. -z >O □A | CH(Et) | s | O | OMe | Cl | F | CH | |
712 | ω / -zHo □A | CH | s | O | OEt | Cl | F | CH |
111
713 | ω / -ζ >ο fa | ^CH | S | o | OMe | Cl | F | CH | |
714 | ο 2 α S^N^O 1 | Y CH | S | o | OEt | Cl | F | CH | |
715 | ω / -ζΗο ofa | ς CH | S | o | OEt | Cl | F | CH | |
716 | V> / -ζΗο fa | 1 °^l CH | s | o | OMe | Cl | F | CH | |
717 | fa ' en | CH(Me) | s | o | OMe | Br | F | CH | |
718 | en > fa -Z >O fa | CH(Me) | s | o | OEt | Br | F | CH | |
719 | en / 2< -Z >O fa | CH(Me) | s | 0 | OMe | cf3 | F | CH | |
720 | ^fa ^fa~ ' en | CH(Me) | s | o | OEt | cf3 | F | CH | |
721 | o ^N^lA S^N^O | CH(Me) | s | o | OMe | CN | F | CH | |
722 | O 2a S^N^O 1 | CH(Me) | s | 0 | OEt | CN | F | CH | |
723 | A4 ,ω O=\ Z— 7¼ ' en | CH(Me) | s | o | OMe | Cl | F | CH | |
724 | 0 N^rA S^N^S 1 | CH(Me) | s | 0 | OEt | Br | F | CH | |
725 | û Ύ^ΐΑ O^N^O 1 | CH(Me) | s | o | OMe | Cl | F | CH |
112
726 | ω , A -Ζ >Ο fa | CH(Me) | S | O | SEt | Cl | F | CH | |
727 | °ΑΓ ' (Λ | CH(Me) | S | O | °Λ / / 0 -|-NH | Cl | F | CH | |
728 | (0 / -ζ >Ο fa | C(Me)2 | S | O | OMe | Cl | F | CH | |
729 | fa ο=< Ζ— ο IL | CH(Me) | S | O | OH | Cl | F | CH | |
730 | J1 ο —ζ Αο ofa | CH(Me) | S | O | OMe | Cl | F | CH | 1H NMR (500 MHz, Chloroform-d) δ 778 (d, J = 9.0 Hz, 1H), 7.22 (d, J = 8.0 Hz, 1H), 6.74 (d, J =1.0 Hz, 1H), 6.08 (s, 1H), 3.80 (s, 6H), 3.47 (q, J = 7.0 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H). |
731 | fa ο=< ζ— ο d? | CH(Me) | S | O | OEt | Cl | F | CH | |
732 | A ο=< ζ— ο IL | CH(Me) | S | O | Cl | F | CH | ||
733 | J1 ο —ζ Α° fa \ ο | CH(Me) | s | O | Cl | F | CH | ||
734 | 0 Αα f3AAo | CH(Me) | s | O | Cl | F | CH | ||
735 | fa° οΑ ζ— ο d? | CH(Me) | s | O | Cl | F | CH | ||
736 | fa° ο=< ζ— ο IL | CH(Me) | s | O | Cl | F | CH |
113
737 | Ο iV f3c n^o | CH(Me) | S | o | Cl | F | CH | ||
738 | <? ο —ζ )=ο | CH(Me) | S | o | Cl | F | CH | ||
739 | ο —ζ )=ο | CH(Me) | S | o | Cl | F | CH | ||
740 | ο —ζ \=ο οΑί | CH(Me) | S | o | Cl | F | CH | ||
741 | π Ο —Ζ Αο | CH(Me) | S | o | Cl | F | CH | ||
742 | οχ ζ— ο d? | CH(Me) | s | 0 | Cl | F | CH | ||
743 | JA οχ ζ— ο IL | CH(Me) | s | o | Cl | F | CH | ||
744 | J1 ο —ζ \=ο | CH(Me) | s | o | Ao | Cl | F | CH | |
745 | οχ ζ— ο LL | CH(Me) | s | o | Χχ | Cl | F | CH | |
746 | J1 ο —ζ /=ο οΑτ | CH(Me) | s | o | Cl | F | CH | ||
747 | JA οχ ζ— ο IL | CH(Me) | s | o | LL | Cl | F | CH | |
748 | ω1 Ο —Ζ \=ο | CH(Me) | s | o | ^GX/CF3 | Cl | F | CH | |
749 | JA οχ ζ— ο ιΤ | CH(Me) | s | o | F\ F χ3^ΧΧ | Cl | F | CH |
114
750 | 0 iV f3c n^o | CH(Me) | S | o | \o^cf3 | C1 | F | CH | |
751 | o rV f3c^n Ί3 | CH(Me) | S | o | C1 | F | CH | ||
752 | <7 o —Z /=O | CH(Me) | S | o | ^O^CN | C1 | F | CH | |
753 | o A f3ctn^o | CH(Me) | S | o | C1 | F | CH | ||
754 t | JA o=< z— o LL? | CH(Me) | S | o | C1 | F | CH | ||
755 | JA o=< z— o IL | CH(Me) | S | 0 | Ao | C1 | F | CH | |
756 | ω1 O —Z \=o | CH(Me) | S | o | Ao °Λ | C1 | F | CH | |
757 | O iV F3CT'N^O | CH(Me) | S | o | ^?2£θ Q '/A/A | C1 | F | CH | |
758 | JA o=< z— o IL | CH(Me) | S | o | /'0 A-s \ | C1 | F | CH | |
759 | J1 o —z \=o i | CH(Me)- | S | o | C1 | F | CH | ||
760 | JAo=\ , z— o LL | CH(Me) | s | o | νογο^ ο | C1 | F | CH | |
761 | <7 o —z \=o | CH(Me) | s | 0 | ο | C1 | F | CH | |
762 | o Â4 f3c n^o | CH(Me) | s | o | 0 | C1 | F | CH |
115
763 | A oA z— o LL | CH(Me) | S | 0 | O | Cl | F | CH | |
764 | oA z— o LL | CH(Me) | S | 0 | 0 \°yv | Cl | F | CH | |
765 | O —z Ao □A | CH(Me) | S | 0 | 0 | Cl | F | CH | |
766 | J1 O —z Ao oA | CH(Me) | S | 0 | O | Cl | F | CH | |
767 | A oA z— 0 LL | CH(Me) | S | 0 | A 0 A1 | Cl | F | CH | |
768 | J1 0 —z Ao □A | CH(Me) | S | 0 | /-0 N | Cl | F | CH | |
769 | J 0 —z Ao □A | CH(Me) | S | 0 | ! T | Cl | F | CH | |
770 | 0 —z Ao □A | CH(Me) | S | 0 | Cl | F | CH | ||
771 | A oA z— 0 LL | CH(Me) | S | 0 | ''Ίό / b | Cl | F | CH | |
772 | J1 O —z Ao | CH(Me) | s | 0 | Cl | F | CH | ||
773 | J1 0 —z Ao □A | CH(Me) | s | 0 | Cl | F | CH | ||
774 | J1 0 —z Ao □A | CH(Me) | s | 0 | .^O'N^cC^Et | Cl | F | CH | |
775 | J 0 —z Ao oA | CH(Me) | s | 0 | F / 0^ | Cl | F | CH |
116
776 | Ο îV f3c^n^o | CH(Me) | S | O | Aq | Cl | F | CH | |
777 | J1 O —z To oA | CH(Me) | S | O | A) O z A | Cl | F | CH | |
778 | O îV F3TrAo | CH(Me) | S | O | Cl | F | CH | ||
779 | J1 O —z To OT | CH(Me) | S | O | o. X° y-z Y/Ao | Cl | F | CH | |
780 | J1 O —z To □A | CH(Me) | S | O | Ao | Cl | F | CH | |
781 | J1 O —Z /=O oA | CH(Me) | S | O | °Ύ | Cl | F | CH | |
782 | J1 O —z To □A | CH(Me) | S | 0 | Ao V/s\ | Cl | F | CH | |
783 | A° o=< z— Q LL | CH(Me) | s | O | Ao | Cl | F | CH | |
784 | A° o=< z— O LL | CH(Me) | s | 0 | Ao AT | Cl | F | CH | |
785 | <T O —z To oA | CH(Me) | s | O | F | Cl | F | CH | |
786 | J O —z To □A | CH(Me) | s | 0 | ^.XT' | Cl | F | CH | |
787 | A° O=< z— O LL | CH(Me) | s | O | T r° / z | Cl | F | CH | |
788 | A° o=< z— O LL | CH(Me) | s | O | /0 Y/^N | Cl | F | CH |
117
789 | Ο —z Ao □A | CH(Me) | s | O | Λο | Cl | F | CH | |
790 | JA o=< z— O IL | CH(F) | s | O | OEt | Cl | F | CH | |
791 | J1 O —z Ao fa | CH(Et) | s | O | OMe | Cl | F | CH | |
792 | J1 O —z Ao fa | CH | s | O | OMe | Cl | F | CH | |
793 | J1 O —z Ao fa l | ^CH | s | O | OMe | Cl | F | CH | |
794 | <? O —z Ao fa | Y CH | s | O | OEt | Cl | F | CH | |
795 | J1 O —z Ao □A | CH(OMe) | s | O | OMe | Cl | F | CH | |
796 | fa o=< z— O LL? | CH(OMe) | s | O | OEt | Cl | F | CH | |
797 | A o=< z— O LL | CH(OMe) | s | O | '’o | Cl | F | CH | |
798 | J1 O —z Ao □A | CH(OMe) | s | O | Cl | F | CH | ||
799 | o=< z— O LL? | CH(OMe) | s | O | r° O Tl ω | Cl | F | CH | |
800 | fa O=< z— O d? | CH(OMe) | s | O | Cl | F | CH | ||
801 | 0 A f3c n o | ς CH | s | O | OMe | Cl | F | CH |
118
802 | J1 Ο —Z )=o | 1 °h CH | S | O | OMe | Cl | F | CH | |
803 | JA o=< z— O d? | CH(Ph) | S | O | OMe | Cl | F | CH | |
804 | O=< z— O IX? | CH(Me) | S | O | OMe | CF, | F | CH | |
805 | J1 O —z y=o | CH(Me) | S | O | OMe | CN | F | CH | |
806 | s FaC-^^O | CH(Me) | s | O | OMe | Cl | F | CH | |
807 | J1 fr ω | CH(Me) | s | 0 | OMe | Cl | F | CH | |
808 | ω1 °\ / Sb ω | CH(Me) | s | 0 | OMe | Cl | F | CH | |
809 | v? ω / b eo LL | CH(Me) | s | O | OMe | Br | F | CH | |
810 | ν' ω / b CO LL | CH(Me) | s | O | OMe | CN | F | CH | |
811 | s ^N^N'h FaC^^^^^S | CH(Me) | s | 0 | OMe | Br | F | CH | |
812 | ,w / b LL | CH(Me) | s | O | OMe | CF, | F | CH | |
813 | S 'Ν'^'ΐΑ FaC^^^S | CH(Me) | s | O | OMe | CN | F | CH | |
814 | S f3cx^/^o | CH(Me) | s | O | OMe | Br | F | CH | |
815 | S 1 FaC^^^O | CH(Me) | s | O | OMe | CF, | F | CH |
119
816 | S X^nV f3c^^o | CH(Me) | S | o | OMe | CN | F | CH | ||
817 | oX Z— o IL· | CH(Me) | S | o | SEt | Cl | F | CH | ||
818 | ω1 o —z Xo □X | CH(Me) | S | o | Cl | F | CH | |||
819 | x° o=( z— o IL· | CH(Me) | S | o | vy | Cl | F | CH | ||
820 | oX z— o IL | CH(Me) | s | o | O *^0) —o | Cl | F | CH | ||
821 | x° oX z— o IL | CH(Me) | s | o | As | Cl | F | CH | ||
822 | x° oX z— o IL? | CH(Me) | s | 0 | / / ° ή-ΝΗ | Cl | F | CH | ||
823 | ω1 O —Z Xo oX | CH(Me) | s | o | \ O | Cl | F | CH | ||
824 | oX z— o IL | CH(Me) | s | o | o X T 1 J o | Cl | F | CH | ||
825 | <T o —z Xo oX | CH(Me) | s | o | k | Cl | F | CH | ||
826 | X —/ b II? | CH(Me) | s | o | OMe | Cl | F | CH | ||
827 | f3( | \ / X ο X | CH(Me) | s | o | OMe | Cl | F | CH | |
828 | ο=ζΧό / o IL? | CH(Me) | s | 0 | OMe | Cl | F | CH |
120
829 | w F3C-t( nJ h2n '—<< o | CH(Me) | S | o | OMe | Cl | F | CH | |
830 | ω1 o —Z 7=0 fa | C(Me)2 | S | o | OMe | Cl | F | CH | |
831 | οχ z— o d? | C(Me)2 | S | o | Cl | F | CH | ||
832 | o sXA) | CH(Me) | S | o | OH | Cl | F | CH | |
833 | o sAA) 1 | CH(Me) | S | o | '/-o ^-CF3 | Cl | F | CH | |
834 | o /a F3C N^O | CH(Me) | S | o | Cl | F | CH | ||
835 | οχ z— o d? | CH(Me) | S | o | CN | Cl | F | CH | |
836 | 0 iV f3c n^o | CH(Me) | s | o | Χ'°γ^οΝ | Cl | F | CH | |
837 | J1 o —z /=o fa | CH(Me) | s | 0 | X'°'^xCN | Cl | F | CH | |
838 | JA οχ z— o d? | CH(Me) | s | o | Cl | F | CH | ||
839 | J1 o —z J=o | CH(Me) | s | o | Cl | F | CH | ||
840 | J1 o —Z Jo fa | CH(Me) | s | o | Cl | F | CH | ||
841 | J o —Z 7=0 fa | CH(Me) | s | o | Cl | F | CH |
121
842 | JA o=< z— O LL | CH(Me) | S | O | /0 | Cl | F | CH | |
843 | O —z Ao □A | CH(Me) | S | O | ! U? \ /° °=< Λ Z z b $=° o | Cl | F | CH | |
844 | ω1 O —z Ao □A | CH(Me) | S | O | |-NH OH | Cl | F | CH | |
845 | H O=Y z— O LL | CH(Me) | S | O | X-Ny ό | Cl | F | CH | |
846 | JA o=< z— O LL | CH(Me) | S | O | JA | Cl | F | CH | |
847 | J O —z Ao oA | CH^ | S | O | OMe | Cl | F | CH | |
848 | A° O=Y z— O LL | Y CH | S | O | OMe | Cl | F | CH | |
849 | jh° O=Y z— O LL | CH^ | s | O | OMe | Cl | F | CH | |
850 | J1 O —z Ao □A | ^F CH | s | O | OMe | Cl | F | CH | |
851 | JA oA z— O d? | o—\ I \__, O | s | O | OMe | Cl | F | CH | |
852 | <7 O —z Ao □A | C(Me)(Et) | s | 0 | OMe | Cl | F | CH | |
853 | 0 FacY^O | CH(Me) | s | O | OMe | Cl | F | CH | |
854 | 0 A^rA FaC'yV Br | CH(Me) | s | O | OMe | Cl | F | CH |
122
855 | Π ω °\ / ο | CH(Me) | s | 0 | OMe | Cl | F | CH | |
856 | “Π ω °\_ / | CH(Me) | s | 0 | OMe | Cl | F | CH | |
857 | ο f3c-'y'% ΟΗ | CH(Me) | s | 0 | 9o^^oh | Cl | F | CH | |
858 | ω1 Ο —Ζ /=Ο □V | CH2CH2 | s | 0 | OMe | Cl | F | CH | |
859 | γ° ο=< ζ— ο LL | CH2CH2 | s | 0 | OEt | Cl | F | CH | |
860 | γ° ο=< ζ— ο d? | CH(Me)CH2 | s | 0 | OMe | Cl | F | CH | |
861 | J1 ο —ζ \=ο □V | CH2CH2CH2 | s | 0 | OMe | Cl | F | CH | |
862 | J1 ο —Ζ /=Ο □V | ^cf3 CH | s | 0 | OEt | Cl | F | CH | |
863 | γ° ο=< ζ— ο IL | CH | s | 0 | OMe | Cl | F | CH | |
864 | γ° ο=< ζ— ο d? | ^Îh | s | 0 | OMe | Cl | F | CH | |
865 | ω1 Ο —Ζ )=Ο oV | 9 CH | s | 0 | OMe | Cl | F | CH | |
866 | Y ογ ζ— ο d? | s | 0 | OMe | Cl | F | CH |
123
867 | ω , Α -Ζ >Ο □Α | CH(Me) | S | o | SEt | Cl | F | CH | |
868 | ο —ζ Αο □Α | CH(Me) | S | o | Cl | F | CH | ||
869 | ο | CH(OMe) | S | o | OMe | Cl | F | CH | |
870 | A ο=4 ζ— ο IL | C(OMe)2 | S | o | OMe | Cl | F | CH | |
871 | Ο iV F3AljAo | CH(Me) | S | o | i o | Cl | F | CH | |
872 | <τ ο —ζ Αο □A | (Ά)Η CH | S | 0 | OMe | Cl | F | CH | |
873 | ο —ζ Αο □Α | HC| CH | S | 0 | OMe | Cl | F | CH | |
874 | <τ ο —ζ Α° □Α | CH(Me) | S | o | oA | Cl | F | CH | |
875 | Α 0=4 Ζ— ο LL | CH(Me) | S | o | nh2 | Cl | F | CH | |
876 | <Τ ο —ζ Αο οΑ | CH(Me) | S | o | j-O cr | Cl | F | CH | |
877 | Ô îV f3AAo | CH(Me) | S | o | Cl | F | CH | ||
878 | J1 ο —ζ Α° cT^ ο | CH(Me) | s | o | A | Cl | F | CH | |
879 | <7 ο —ζ Αο □Α | CH(Me) | s | o | s H 0 | Cl | F | CH |
124
880 | Ô F3C nAd | CH(Me) | S | O | OMe | Cl | F | N | |
881 | ω / η □A | CH(Me) | NH | O | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-de) δ 8.24 (d, J= 1.0 Hz, 1H),7.25 — 7.19 (m,2H), 4.46 (s, 1H), 3.75 (s, 6H), 3.65 (s, 3H), 3.56 (q,J= 7.0 Hz, 1H), 1.27 (d, J=7.0 Hz, 3H). |
882 | ο Α^ιΑ sAnH0 1 | CH(Me) | NH | O | OEt | Cl | F | CH | |
883 | ο sVnHo 1 | CH(Me) | NH | s | OEt | Cl | F | CH | |
884 | ω , -Ζ >=Ο 1 Ο Y ί | CH(Me) | NH | 0 | fo | Cl | F | CH | |
885 | ω , A -ζ >ο □Α | CH(Me) | N Me | o | Cl | F | CH | ‘H NMR (500 MHz, DMSO-di) Ô8.32(d,j = 1.0 Hz, 1H),7.25 — 7.19 (m,2H), 4.95-4.90 (m, 1H), 3.75 (s, 6H), 3.56 (q,J= 7.0 Hz, 1 H), 3.00 (s,3H), 1.21-1.19 (m, 6H), 1.16 (d,J= 7.0 Hz, 3H). | |
886 | ο Α^ιΑ sAnAo 1 | CH(Me) | NH | o | Cl | F | CH | ||
887 | ω / Aio οΑ | CH(Me) | NH | o | /O | Cl | F | CH | |
888 | ο Α^ιΑ . sVNV0 1 | CH(Me) | NH | o | A | Cl | F | CH | |
889 | ω / Α -Ζ >Ο □Α | CH(Me) | NH | o | /-0 H | Cl | F | CH |
125
890 | ω / -ζ >ο fa | CH(Me) | N Me | O | /'O ^cf3 | Cl | F | CH | |
891 | ω / A -ζ >ο fa | CH(Me) | NH | O | A o | Cl | F | CH | |
892 | ω / A -ζ >ο ofa | CH(Me) | NH | O | O AA | Cl | F | CH | |
893 | fa far 7 ω | CH(Me) | NH | O | /O nV | Cl | F | CH | |
894 | Ο sY'N^O 1 | CH(Me) | NH | O | /O | Cl | F | CH | |
895 | ω , Υ\_ -Ζ >Ο fa | CH(Me) | NH | O | ° A oA | Cl | F | CH | |
896 | Ο S^N^O | CH(Me) | NH | O | /O | Cl | F | CH | |
897 | Ο Α^γΑ sY'N'^O 1 | CH(Me) | NH | O | /O A/^n A? | Cl | F | CH | |
898 | ω / fa -ζ >0 fa | CH(Me) | NH | O | Ao | Cl | F | CH | |
899 | fa ^fa~ ' tn | CH(F) | NH | O | OEt | Cl | F | CH | |
900 | Ο S^'N^O 1 | CH(Et) | NH | O | OMe | Cl | F | CH | |
901 | ω / A -ζ >ο fa | CH | NH | O | OEt | Cl | F | CH | |
902 | ω / -ζΗο fa | ^CH | NEt | O | OMe | Cl | F | CH |
126
903 | (Λ / Η -z >0 oA | Y CH | NH | O | OEt | Cl | F | CH | |
904 | ω / K -Z >O □A | ς CH | NH | O | OEt | CI | F | CH | |
905 | O ^fAfA sAnAo 1 | 1 °~Ί CH | NH | O | OMe | Cl | F | CH | |
906 | j-A A ' <n | CH(Me) | NH | O | OMe | Br | F | CH | |
907 | O fAiA sANAq 1 | CH(Me) | NH | O | OEt | Br | F | CH | |
908 | O sAnAo 1 | CH(Me) | NH | O | OMe | cf3 | F | CH | |
909 | O ΧνΆ sAnAo 1 | CH(Me) | NH | O | OEt | CFj | F | CH | |
910 | AA ' ω | CH(Me) | NH | O | OMe | CN | F | CH | |
911 | O fAfA sAnAo 1 | CH(Me) | NH | O | OEt | CN | F | CH | |
912 | O ^fAfA | CH(Me) | NH | O | OMe | Cl | F | CH | |
913 | ω / H -z >o ,)=¾. ω æv | CH(Me) | NH | O | OEt | Br | F | CH | |
914 | A °A ?/% | CH(Me) | NH | O | OMe | Cl | F | CH | |
915 | A Aa ' tn | CH(Me) | NH | O | SEt | Cl | F | CH |
127
916 | Ο S^nX) | CH(Me) | Nil | O | °λ / / ° -|NH | Cl | F | CH | |
917 | ω / A -z >o □A | C(Me)i | NH | O | OMe | Cl | F | CH | |
918 | P o=< z— O LL? | CH(Me) | NH | O | OH | Cl | F | CH | |
919 | =/^0 oA z— o LL | CH(Me) | NH | 0 | OMe | Cl | F | CH | ‘H NMR (500 MHz, DMSO-A) δ 8.01 (t, 7=4.5 Hz, 1 H), 7.71 (d, 7=9.0 Hz, 1 H), 7.40 (d, 7= 8.0 Hz, 1H), 6.57 (s, 1 H), 4.56 (d, 7= 4.0 Hz, 1H), 3.62 (s, 3H), 3.40 (s, 3H), 1.90 (s, 3H). |
920 | A° oA z— o d? | CH(Me) | NH | 0 | OEt | Cl | F | CH | |
921 | A o=< z— o LL | CH(Me) | NH | O | Cl | F | CH | ||
922 | A O=< z— o d? | CH(Me) | NH | 0 | cA | CI | F | CH | |
923 | A O=\ z— \=/ o d? | CH(Me) | NEt | 0 | Cl | F | CH | ||
924 | A o=< z— o d? | CH(Me) | NH | 0 | Cl | F | CH | ||
925 | JlV f3c n^o | CH(Me) | NH | O | ν°η< | Cl | F | CH | |
926 | J1 o —Z K° o | CH(Me) | NH | O | ΥθχΧΑ/Χ | Cl | F | CH | |
927 | J1 o —z Ao □A | CH(Me) | NH | O | Cl | F | CH |
128
928 | o=A z— O d? | CH(Me) | NH | O | Cl | F | CH | ||
929 | O=< z— O co LL | CH(Me) | NH | O | Cl | F | CH | ||
930 | <7 O —z \=o | CH(Me) | NH | O | Cl | F | CH | ||
931 | z— O d? | CH(Me) | NH | O | Cl | F | CH | ||
932 | O iV F3CT'N'A) | CH(Me) | NMe | O | Cl | F | CH | ||
933 | J1 O —z Ao o | CH(Me) | NH | O | /Ο | Cl | F | CH | |
934 | o=< z— O d? | CH(Me) | NH | O | Cl | F | CH | ||
935 | J1 O —z )=o | CH(Me) | NH | O | Cl | F | CH | ||
936 | J1 O —Z Ao | CH(Me) | NH | O | F V°^F | Cl | F | CH | |
937 | o=< z— O d? | CH(Me) | NH | O | X°-cf3 | Cl | F | CH | |
938 | ô /a f3c^n^o | CH(Me) | NEt | O | F\ F | Cl | F | CH | |
939 | <T O —Z /=O | CH(Me) | NH | O | ^A-^GFa | Cl | F | CH | |
940 | ô /a f3c n o | CH(Me) | NH | O | Cl | F | CH |
129
941 | J1 Ο —Ζ \=ο fa | CH(Me) | NH | O | ^O^-CN | Cl | F | CH | |
942 | 1 fa ο=< ζ— ο LL· | CH(Me) | NH | O | CI | F | CH | ||
943 | Α° ο=< ζ— ' \ ο IL· | CH(Me) | NH | O | Cl | F | CH | ||
944 | fa Ο=Υ Ζ— ο ιΤ | CH(Me) | NH | O | Ao | Cl | F | CH | |
945 | ο —ζ )=ο fa | CH(Me) | NH | O | /0 °Λ | Cl | F | CH | |
946 | fa ο=< ζ— ο LL· | CH(Me) | NH | O | --- | Cl | F | CH | |
947 | fa. ο=< ζ— ο IL· | CH(Me) | NH | O | /'O ^~s \ | Cl | F | CH | |
948 | ω1 Ο —Ζ \=ο fa | CH(Me) | NH | 0 | Cl | F | CH | ||
949 | ο=< ζ— ο IL· | CH(Me) | NH | O | V°Y°^ 0 | Cl | F | CH | |
950 | 1 fa ο=< Ζ— ο (Ό U. | CH(Me) | NH | O | 0 αλΑ | Cl | F | CH | |
951 | ο=\ ζ , ο LL | CH(Me) | NH | O | O | Cl | F | CH | |
952 | fa °=ο- ο IL· | CH(Me) | NH | 0 | O | CI | F | CH | |
953 | ο=< Ζ— ο IL· | CH(Me) | NH | O | 0 \°yv | Cl | F | CH |
130
954 | Ο —ζ Αο fa | CH(Me) | NII | 0 | O x'A'0'' | Cl | F | CH | |
955 | ο=< ζ— ο LL? | CH(Me) | NH | O | \ J° )=o °\ | Cl | F | CH | |
956 | ω1 Ο —ζ Αο fa | CH(Me) | NH | 0 | O | Cl | F | CH | |
957 | ω1 ο —ζ Αο fa | CH(Me) | NH | 0 | /O | Cl | F | CH | |
958 | ω1 ο —ζ Αο fa | CH(Me) | NH | O | Cl | F | CH | ||
959 | Ô Λ f3c ν ο | CH(Me) | NH | O | / A | Cl | F | CH | |
960 | J1 ο —ζ Αο fa | CH(Me) | NH | 0 | v°-zA | Cl | F | CH | |
961 | ω1 ο —ζ Αο fa | CH(Me) | NH | 0 | Cl | F | CH | ||
962 | fa O=C/Z_ ο LL? | CH(Me) | NH | O | Ad / Y O | Cl | F | CH | |
963 | fa o=Y z— O if? | CH(Me) | NH | O | V°'N<?^C02Et | Cl | F | CH | |
964 | J O —z Ao fa | CH(Me) | NH | O | X°-n^Q | Cl | F | CH | |
965 | 2s P J-Λ o=< z— o LL? | CH(Me) | NH | O | /'O | Cl | F | CH | |
966 | JH° O=Y z— O IL? | CH(Me) | NH | 0 | Zd O V z A | Cl | F | CH |
131
967 | ω1 Ο —Ζ /=Ο fa | CH(Me) | NH | O | P | Cl | F | CH | |
968 | Ô îV F3CT^N'AD | CH(Me) | NH | O | 0 \°'νΛ q' | Cl | F | CH | |
969 | <7 ο —Ζ \=Ο fa | CH(Me) | NH | O | /~~o \^,o^ | Cl | F | CH | |
970 | ω1 ο —ζ \=ο fa 1 | CH(Me) | NH | o | C'A | Cl | F | CH | |
971 | fa Ο=< ζ— ο LL? | CH(Me) | NH | 0 | /O | Cl | F | CH | |
972 | Ο JL A f3c^n^o | CH(Me) | NH | 0 | Ao | Cl | F | CH | |
973 | fa Ο=Υ ζ— ο IL | CH(Me) | NH | o | A° 'O | Cl | F | CH | |
974 | fa ο=/ ζ— ϋ IL | CH(Me) | NH | 0 | F ,;OXJ | Cl | F | CH | |
975 | fa Ο=Υ ζ— ο IL | CH(Me) | NH | 0 | 1 U. | Cl | F | CH | |
976 | ω1 Ο —Ί \=ο fa | CH(Me) | NH | o | Ύ / Z | Cl | F | CH | |
977 | fa ο=< ζ— ο d? | CH(Me) | NH | o | λ y o-^ | Cl | F | CH | |
978 | Λ f3c^n^o | CH(Me) | NH | o | 9 | Cl | F | CH | |
979 | jh° ο=< ζ— ο d? | CH(F) | NH | o | OEt | Cl | F | CH |
132
980 | J1 Ο —z Ao OA | CH(Et) | NH | O | OMe | Cl | F | CH | |
981 | A o=< z— O d? | CH | NH | O | OMe | Cl | F | CH | |
982 | J1 O —z Ao fa | ^CH | NH | O | OMe | Cl | F | CH | |
983 | A oA z— O LL? | Y CH | NH | O | OEt | Cl | F | CH | |
984 | <7 O —z Ao | CH(OMe) | NH | O | OMe | Cl | F | CH | |
985 | O Ac f3c n o | CH(OMe) | NH | O | OEt | Cl | F | CH | |
986 | <7 O —z Ao ofa | CH(OMe) | NH | O | Cl | F | CH | ||
987 | 0 Ai f3c^n^o | CH(OMe) | NH | O | Cl | F | CH | ||
988 | A oA z— O LL? | CH(OMe) | NH | O | O τι ω | Cl | F | CH | |
989 | A OA z— O d? | CH(OMe) | NH | O | Cl | F | CH | ||
990 | A oA z— O d? | ς CH | NH | O | OMe | Cl | F | CH | |
991 | J1 O —z Ao □A | CH | NH | O | OMe | Cl | F | CH | |
992 | <7 o —z Ao □A | CH(Ph) | NH | 0 | OMe | Cl | F | CH |
133
993 | A °=\,z~ o IL | CH(Me) | NH | O | OMe | CFj | F | CH | |
994 | A oA z— o d? | CH(Me) | NH | O | OMe | CN | F | CH | |
995 | S | CH(Me) | NH | O | OMe | Cl | F | CH | |
996 | 0 A'n’< f3c^^s | CH(Me) | NH | o | OMe | Cl | F | CH | |
997 | s A’. FaC^^S | CH(Me) | NH | o | OMe | CI | F | CH | |
998 | ω / b ce LL· | CH(Me) | NH | o | OMe | Br | F | CH | |
999 | J1 °\ / A ω | CH(Me) | NH | o | OMe | CN | F | CH | |
1000 | S F3C^^S | CH(Me) | NH | o | OMe | Br | F | CH | |
1001 | A ”<A / b d? | CH(Me) | NH | 0 | OMe | cf3 | F | CH | |
1002 | s XN^rA f3cx^x^s | CH(Me) | NH | o | OMe | CN | F | CH | |
1003 | s xn^nV F3C'^^O | CH(Me) | NH | o | OMe | Br | F | CH | |
1004 | s AnX f3c/1<î^o | CH(Me) | NH | o | OMe | cf3 | F | CH | |
1005 | J1 O A | CH(Me) | NH | o | OMe | CN | F | CH | |
1006 | A □A z— b IL | CH(Me) | NH | o | SEt | Cl | F | CH |
134
1007 | ! i ΊΊ ω Ο —ζ \=ο | CH(Me) | NH | O | Cl | F | CH | |||
1008 | JM° οχ ζ— ο IL | CH(Me) | NII | O | Cl | F | CH | |||
1009 | JA οχ Ζ— ο ιΤ | CH(Me) | NH | O | o— OT^ ° | Cl | F | CH | ||
1010 | 0 îV . f3c n^o | CH(Me) | NH | O | X o | Cl | F | CH | ||
1011 | <7 ο —ζ V=o | CH(Me) | NH | 0 | O O<1 L t Z χνν | Cl | F | CH | ||
1012 | ω1 ο —ζ )=ο ο | CH(Me) | NH | 0 | kV | Cl | F | CH | ||
1013 | 0 f3c n^o | CH(Me) | NH | O | Anh Λθζ °/N Λ | Cl | F | CH | ||
1014 | J1 ο —ζ \=ο οΑί | CH(Me) | NH | O | Cl | F | CH | |||
1015 | “Π ω A | CH(Me) | NH | O | OMe | Cl | F | CH | ||
1016 | F3< | ' ο :α^α0 | CH(Me) | NH | O | OMe | Cl | F | CH | |
1017 | 0 F3CxY'X) Cl | CH(Me) | NH | O | OMe | Cl | F | CH | ||
1018 | Μ° f3c-χ Ηη2ν '— ο | CH(Me) | NH | O | OMe | Cl | F | CH | ||
1019 | JA οχ ζ— ο d? | C(Me)i | NH | 0 | OMe | Cl | F | CH |
135
1020 | x° oX z— o d? | C(Me)j | NH | O | Cl | F | CH | ||
1021 | O S^N\d 1 | CH(Me) | NH | O | OH | Cl | F | CH | |
1022 | o S^N^O 1 | CH(Me) | NH | O | /-o ^cf3 | Cl | F | CH | |
1023 | xf oX z— o d? | CH(Me) | NH | 0 | Cl | F | CH | ||
1024 | J1 o —z Xo O | CH(Me) | NH | o | \°Y CN | Cl | F | CH | |
1025 | J1 o —z Xo cX | CH(Me) | NH | 0 | Χ'θΎ^ΟΝ | Cl | F | CH | |
1026 | x° oX z— o LL? | CH(Me) | NH | o | X-O-^xLcn | Cl | F | CH | |
1027 | x° oX Z— o d? | CH(Me) | NH | 0 | Cl | F | CH | ||
1028 | T ω O —Z >=O oX | CH(Me) | NH | o | Cl | F | CH | ||
1029 | J1 o —z Xo oX | CH(Me) | NH | o | Cl | F | CH | ||
1030 | oX z— o d? | CH(Me) | NH | o | Cl | F | CH | ||
1031 | O iV F3crX''XD | CH(Me) | NH | o | /O | Cl | F | CH | |
1032 | JA° oX z— o d? | CH(Me) | NH | o | o=< Λ r z b $=° o S | Cl | F | CH |
136
1033 | o=Y z— O LL | CH(Me) | NH | O | |-NH OH | Cl | F | CH | |
1034 | JA o=< z— O LL | CH(Me) | NH | O | YNy 0 | Cl | F | CH | |
1035 | JA oA z— O LL | CH(Me) | NH | O | Cl | F | CH | ||
1036 | oA Z— O LL | CH^ | NH | O | OMe | Cl | F | CH | |
1037 | JA3 OA z— ü LL | Y CH | NH | O | OMe | Cl | F | CH | |
1038 | O —Z Ao | CH^ | NH | 0 | OMe | Cl | F | CH | |
1039 | <? O —z \=o | ^F CH | NH | O | OMe | Cl | F | CH | |
1040 | JA° oA z— O LL? | O —\ X X—o | NH | O | OMe | Cl | F | CH | |
1041 | JA° oA z— O LL | C(Me)(Et) | NH | O | OMe | Cl | F | CH | |
1042 | v> P / O LL? | CH(Me) | NH | O | OMe | Cl | F | CH | |
1043 | 0 F3c''yA>o Br | CH(Me) | NH | O | OMe | Cl | F | CH | |
1044 | h/ O IL | CH(Me) | NH | O | OMe | Cl | F | CH | |
1045 | α^λ / b CO LL | CH(Me) | NH | O | OMe | Cl | F | CH |
137
1046 | Ô ''γΑν'Ά. FjcAA) OH | CH(Me) | NH | 0 | ^OH | Cl | F | CH | |
1047 | JX o=< z— o d? | CH2CH2 | NH | O | OMe | Cl | F | CH | |
1048 | J1 O —z \=o | CH2CH2 | NH | O | OEt | Cl | F | CH | |
1049 | JA O=Y z— o d? | CH(Me)CH2 | NH | O | OMe | Cl | F | CH | |
1050 | JX z— 0 d? | CH2CH2CH2 | NH | O | OMe | Cl | F | CH | |
1051 | J1 O □H | ^cf3 CH | NH | O | OEt | Cl | F | CH | |
1052 | JX oj z— o d? | CH | NH | O | OMe | Cl | F | CH | |
1053 | 0 rV F3C Ijl^O | ^Ih | NH | O | OMe | Cl | F | CH | |
1054 | J1 o —Z^ ^>=O M | 9 CH | NH | O | OMe | Cl | F | CH | |
1055 | JA o=f z— o d? | ^Ïh | NH | 0 | OMe | Cl | F | CH | |
1056 | JM A ' ω | CH(Me) | NH | 0 | SEt | Cl | F | CH | |
1057 | X P o=< z— o d? | CH(Me) | NH | O | Cl | F | CH | ||
1058 | Ά'Υ o | CH(OMe) | NH | O | OMe | Cl | F | CH |
138
1059 | J1 O —Z \=o ofa | C(0Me)2 | NH | O | OMe | Cl | F | CH | |
1060 | οχ z— o LL | CH(Me) | NH | O | 1 if | Cl | F | CH | |
1061 | J1 o —z )=o fa | CH | NH | O | OMe | Cl | F | CH | |
1062 | οχ z— o LL | r^ci CH | NH | O | OMe | Cl | F | CH | |
1063 | J1 o —Z \=O ofa | CH(Me) | NH | o | ofa | Cl | F | CH | |
1064 | JA οχ Z— o LL | CH(Me) | NH | o | nh2 | Cl | F | CH | |
1065 | JA οχ z— o LL | CH(Me) | NH | o | Cl | Cl | F | CH | |
1066 | JA οχ z— o LL | CH(Me) | NH | o | __^1 | Cl | F | CH | |
1067 | JA οχ z— o LL | CH(Me) | NH | o | M | Cl | F | CH | |
1068 | o Λ F3C N O | CH(Me) | NH | o | . H -VN^O £<>CI O | Cl | F | CH | |
1069 | JA οχ Z— o IL | CH(Me) | NH | o | OMe | Cl | F | N |
Table A is constructed in the same way as that of Table 1 above, except for replacing the
racemate compounds having a chiral center ( N'X3XYW x4 □ , wherein, X represents
-C*XiX2-(alkyl)n-, -alkyl-C*XiX2-(alkyl)n-, that is, Xi, X2 are not the same, the carbon atom at *
139 is the chiral center) (that is, compounds 1-188, 193-432, 438-439, 441-469, 471-478, 481-484, 486-493, 495-545, 547-641, 644-669, 672, 674-681, 683-727, 729-829, 832-857, 860, 862-869, 871-916, 918-1018, 1021-1046, 1049, 1051-1058 and 1060-1069) with the corresponding compounds in R configuration and deleting the compounds having no chiral center at the corresponding position, and in Table A, the entries in the column No. are listed in sequence as “1(R)-188(R), 193(R)-432(R), 438(R)-439(R), 441(R)-469(R), 471(R)-478(R), 481(R)-484(R), 486(R)-493(R), 495(R)-545(R), 547(R)-641(R), 644(R)-669(R), 672(R), 674(R)-681(R), 683(R)-727(R), 729(R)-829(R), 832(R)-857(R), 860(R), 862(R)-869(R), 871(R)-916(R), 918(R)-1018(R), 1021(R)-1046(R), 1049(R), 1051(R)-1058(R) and 1060(R)-1069(R)”. For example, “1(R)” corresponds to R configuration of compound “1” in Table 1, “194(R)” corresponds to R configuration of compound “194” in Table 1.
The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route hâve been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the préparation method of the présent invention is included in the scope of the présent invention. In addition, the following préparation method can be fiirther modified according to the disclosures of the présent invention by using common Chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.
The following method of application can be used to improve fiirther understanding of the préparation method of the présent invention. The spécifie material, class and condition hâve been determined to be fiirther explication of the présent invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.
Examples of représentative compounds are as follows, the synthesis methods of other compounds are similar, and will not be described in detail here.
1. Synthesis of compound 1
1) 1-1 (10 g, 49.1 mmol, 1.0 eq), Fe powder (8.23 g, 147.4 mmol, 3.0 eq), NH4CI (5.26 g, 98.3 mmol, 2.0 eq) and water (50 ml) were added to 500 ml of EtOH solution in sequence. Then,
140 the reaction solution was reacted at 80°C for 1 hour. LCMS test showed the disappearance of raw materials. After filtration, the solution was concentrated to remove éthanol and then extracted with ethyl acetate. The organic phase was washed with saturated brine (100ml*l), and then concentrated to obtain 1-2 (12 g, crude product) (black solid).
2) 1-2 (12 g, 69.1 mmol, 1.0 eq, crude product) was added to 100 ml of toluene solution. Then, 1-3 (10.8 g, 69.1 mmol, 1.0 eq) was added to the reaction solution at 100°C. After the addition was completed, the reaction solution was reacted at 100°C for 1 hour. LCMS test showed the disappearance of raw materials, and the génération of a product. The reaction solution was concentrated to remove toluene. The resulting crude product was separated by column chromatography to obtain 1-4 (5g) (yellow solid).
3) 1-5 (3.8 g, 17.0 mmol, 1.0 eq) and AcONa (0.7 g, 8.5 mmol, 0.5 eq) were added to 50 ml of DMF solution. Then, 1-4 (5 g, 17.0 mmol, 1.0 eq) was added to the reaction solution at 60°C. After the addition was completed, the reaction solution was reacted at 60°C for 1 hour. LCMS test showed the disappearance of raw materials, and the occurrence of new peak. After the addition of water (50ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (100ml*l), and then concentrated. The resulting crude product was separated by column chromatography to obtain 1-6 (4.0 g, 71.3% yield) (white solid).
4) 1-6 (4 g, 12.1 mmol, 1.0 eq) was added to 40 ml of EtOH, and then NH2OHHCI (0.93 g,
141
13.3 mmol, 1.1 eq) aqueous solution (6 ml) was added dropwise to the reaction solution at 0°C. After the addition was completed, the reaction solution was stirred at 0°C for 2 hours. LCMS test showed that the raw materials were almost consumed, and one major new peak occurred. The reaction solution was concentrated to remove a part of éthanol and then poured into 10 ml of water, causing a solid to precipitate out. After filtration, the filter cake was washed with water and dried to obtain 1-7 (7 g, 71.7% yield) (white solid).
5) 1-7 (0.2 g, 0.58 mmol, 1.0 eq), a (0.14 g, 1.1 mmol, 2 eq) and K2CO3 (0.24 g, 1.74 mmol, 3 eq) were added to 5 mL of DMF solution in sequence. Then, the reaction solution was reacted at room température for 4 hours. LCMS test showed the disappearance of raw materials, and there were ail product peaks. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml*l), and then concentrated. The resulting crude product was separated by column chromatography to obtain 1 (0.15 g, 60 % yield) (white solid).
2. Synthesis of compound 1(R) configuration
1-7 (0.2 g, 0.58 mmol, 1.0 eq), b (0.14 g, 1.1 mmol, 2 eq), K2CO3 (0.24 g, 1.74 mmol, 3 eq) were added to 5 mL of DMF solution in sequence. Then, the reaction solution was reacted at room température for 4 hours. LCMS test showed the disappearance of raw materials, and there were ail product peaks. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml*l), and then concentrated. The resulting crude product was separated by column chromatography to obtain 1(R) (0.15 g, 60% yield, R/S=98/2) (white solid).
142
3. Synthesis of compound 194(R)
1) 1-1 (20 g, 98.3 mmol, 1.0 eq) was added to 200 ml of EtOH, and then NH2OHHC1 (7.5 g, 108.1 mmol, 1.1 eq) aqueous solution (30 ml) was added dropwise to the reaction solution at 0°C.
After the addition was completed, the reaction solution was stirred at 0°C for 3 hours. LCMS test showed that the raw materials were almost consumed and one major new peak occurred. The reaction solution was concentrated to remove a part of éthanol and then poured into 100 ml of water, causing a solid to precipitate out. After filtration, the filter cake was washed with water and dried to obtain 194-1 (20 g, 93% yield) (white solid).
10 1-1 194-1
2) 194-1 (5 g, 22.9 mmol, 1.0 eq), Fe powder (3.8 g, 68.6 mmol, 3 eq), NH4C1 (2.5 g, 45.8 mmol, 2 eq) and water (10ml) were added to 50 ml of EtOH in sequence. Then, the reaction solution was reacted at 80°C for 1 hour. LCMS test showed the occurrence of product peak. The reaction solution was filtered with celite and then concentrated to remove éthanol. After the 15 addition of water (20ml), the reaction solution was extracted with ethyl acetate and then concentrated to obtain a black crude product. The crude product was separated and purified by column chromatography to obtain 194-2 (2 g, 46.4% yield) (gray solid).
3) 194-2 (1 g, 5.3 mmol, 1.0 eq) and c (1.1 g, 5.3 mmol, 1.0 eq) were added to 20 ml of
143 acetic acid, and the reaction solution was reacted at 110°C for 1 hour. LCMS test showed that the reaction of raw materials was basically completed, and there was one major product peak. The reaction solution was concentrated to remove the solvent. The resulting crude product was separated by column chromatography to obtain 194-3 (1.5 g, 80.5% yield) (white solid).
çf3
4) 194-3 (0.4 g, 1.1 mmol, 1.5 eq), b (0.18 g, 1.5 mmol, 1.3 eq) and K2CO3 (0.2 g, 1.5 mmol, 1.3 eq) were added to 8 ml of DMF in sequence. Then, the reaction solution was reacted at 25°C for 4 hours. LCMS test showed the génération of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml*l), and then concentrated. The resulting crude product was separated by column chromatography to obtain 194-4 (0.3 g, 60.2% yield) (white solid).
5) 194-4 (0.3 g, 0.69 mmol, 1.0 eq), Mel (0.13 g, 0.9 mmol, 1.3 eq) and K2CO3 (0.12 g, 0.9 mmol, 1.3 eq) were added to 6 ml of DMF in sequence. Then, the reaction solution was reacted 15 at 25°C for 2 hours. LCMS test showed the génération of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml*l), and then concentrated. The resulting crude product was separated by column chromatography to obtain 194(R) (0.2 g, 64.6% yield, R/S=99/l) (white solid).
144
4. Synthesis of compound 504 (1) 504-1 (2 g, 1.0 eq), DessMartin (4.8 g, 2 eq) were added to 50 ml of DCM solution.
Then, the reaction solution was reacted at room température for 2 hours. LCMS test showed the completion of reaction. After the addition of NaHCO3 aqueous solution (100ml), the reaction solution was extracted with DCM. The organic phase was washed with saturated brine (100ml*2), and then concentrated. The resulting crude product was separated by column chromatography to obtain 504-2 (1.6 g, 82% yield) (white solid).
(2) 504-2 (1.6 g, 1.0 eq), water (10 ml), hydroxylamine hydrochloride (0.63 g, 2 eq) were added to 30 ml of éthanol solution. Then, the reaction solution was reacted at room température for 2 hours. LCMS test showed the completion of reaction. The reaction solution was concentrated. The resulting crude product was separated by column chromatography to obtain
504-3 (1.1 g, 69% yield) (white oil).
ci nh2ohhci^ F3C \ /Ν3, )“CI
EtOHHoO * / t) \
504-2 ° 504.3 OH (3) 504-3 (0.3 g, 1.0 eq) and K2CO3 (170 mg, 1.5 eq) were added to 10 ml of DMF, then a (150 mg, 1.5 eq) was added to the reaction solution at 25°C, followed by reacting at 25°C for 8 hours. LCMS test showed the génération of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (20ml* 1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 504 (0.2 g, 54% yield) (white solid).
145
a
K2CO3, DMF
504
5. Synthesis of compound 919 (1) 919-1 (0.3 g, 1.0 eq) and NH2NH2H2O (0.5 g, 85% aqueous solution, 10 eq) were added to 10 ml of THF. Then, the reaction solution was stirred at 60°C for 3 hours. LCMS test showed the génération of a product. The reaction solution was concentrated. The resulting crude product was separated by column chromatography to obtain 919-2 (0.15 g, 48%yield) (white solid).
(2) 919-2 (0.15 g, 1.0 eq) and K2CO3 (74 mg, 1.3 eq) were added to 6 ml of DMF, then a (55 mg, 1.1 eq) was added to the reaction solution at 25°C, followed by reacting at 25°C for 8 hours. LCMS test showed the génération of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (20ml* 1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 919 (50 mg, 27% yield) (white solid).
919-2 919
Biological activity évaluation:
The activity level criteria for plant damage (i.e., growth control rate) are as follows:
Level 5: growth control rate is above 85%;
Level 4: growth control rate is greater than or equal to 60% and less than 85%;
Level 3: growth control rate is greater than or equal to 40% and less than 60%;
Level 2: growth control rate is greater than or equal to 20% and less than 40%;
Level 1: growth control rate is greater than or equal to 5% and less than 20%;
Level 0: growth control rate is less than 5%.
146
The above growth control rates are fresh weight control rates.
Experiment on weeding effect in post-emergence stage:
Monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Abutilon theophrasti, Galium aparine, Stellaria media, Lithospermum arvense, rorippa indica, Alopecunts aequalis, Alopecurus japonicus, Eleusine indica, Beckmannia syzigachne, Sclerochloa dura, Conyza Canadensis, Phleum paniculatum, Veronica didyma Tenore, Bromus japonicus, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodiaceae, Commelina communis, Sonchus arvensis, Convolvulus arvensis, Cirsium setosum, Bidens tripartita L., Solanum nigrum, Acalypha australis, Digitaria sanguinalis, Echinochloa crusgalli, Setaria viridis, Setaria glauca, Leptochloa chinensis, Monochoria vaginalis, Sagittaria trifolia, Scirpus juncoides, Cyperus rotundus, Cyperus iria, Cyperus dîffbrmis, Fimbristylis, Portulaca oleracea, Xanthium sibiricum, Pharbitis nil, etc.) and major crop seeds (wheat, corn, rice, soybean, cotton, oilseed râpe, millet, sorghum, potato, sesame, ricinus, etc.) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated in the 2-3 leaf stage. The tested compounds of the présent invention were respectively dissolved in acetone, then added with Tween 80 and 1.5 liter/ha of emulsifiable concentrate of methyl oleate as synergist, diluted with a certain amount of water to obtain a solution with a certain concentration, and sprayed with a spray tower onto the plants. After the application, the plants were cultured for 3 weeks in the greenhouse, and then the experimental results of the weeding were counted. The doses of the used compounds were 500, 250, 125, 60, 30, 15, 7.5g/ha, and the averages were obtained by repeating for three times. Représentative data are listed in Table 2.
Table 2. Results on weeding effect in post-emergence stage
Compound NO. | Digitaria sanguinalis | Echinochloa crusgalli | Setaria viridis | Eleusine indica | Alopecurus japonicus | Abutilon theophrasti | Dose |
1 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
1(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
2 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
2(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
3 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
147
3(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
4 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
4(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
5 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
5(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
6 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
6(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
9 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
9(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
10 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
10(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
11 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
11(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
12 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
12(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
14 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
14(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
17 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
17(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
20 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
20(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
24 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
24(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
26 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
26(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
42 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
42(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
59 | 5 | 5 | 5 | 5 | N | 5 | 15g/ha |
59(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
60 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
60(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
72 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
148
72(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
74 | 4 | 5 | 5 | 4 | N | 5 | 15g/ha |
74(R) | 4 | 5 | 5 | 5 | N | 5 | 15g/ha |
76 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
76(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
80 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
80(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
83 | 4 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
83(R) | 4 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
84 | 4 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
84(R) | 4 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
85 | 5 | 5 | 5 | 5 | N | 5 | 15g/ha |
85(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
86 | 3 | 4 | 4 | 5 | 3 | 5 | 15g/ha |
86(R) | 3 | 4 | 4 | 5 | 3 | 5 | 15g/ha |
87 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
87(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
88 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
88(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
124 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
124(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
161 | 4 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
161(R) | 4 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
164 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
164(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
168 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
168(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
183 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
183(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
189 | 4 | 4 | 5 | 5 | 4 | 5 | 15g/ha |
193 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
193(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
149
194 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
194(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
194 | 5 | 5 | 5 | 5 | 4 | 5 | 7.5g/ha |
194(R) | 5 | 5 | 5 | 5 | 5 | 5 | 7.5g/ha |
196 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
196(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
198 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
198(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
199 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
199(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
200 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
200(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
201 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
201 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
202 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
202(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
203 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
203(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
204 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
204(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
205 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
205(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
206 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
206(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
207 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
207(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
208 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
208(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
209 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
209(R) | . 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
212 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
212(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
150
214 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
214(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
216 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
216(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
217 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
217(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
218 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
218(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
220 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
220(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
221 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
221 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
225 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
225(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
226 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
226(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
227 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
227(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
228 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
228(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
230 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
230(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
231 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
231 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
232 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
232(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
233 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
233(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
234 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
234(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
236 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
236(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
151
238 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
238(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
239 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
239(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
240 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
240(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
241 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
241 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
243 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
243(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
245 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
245(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
246 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
246(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
248 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
248(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
249 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
249(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
250 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
250(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
251 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
251 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
252 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
252(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
253 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
253(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
254 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
254(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
255 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
255(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
258 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
258(R) | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
152
259 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
259(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
262 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
262(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
263 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
263(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
264 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
264(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
266 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
266(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
268 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
268(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
283 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
283(R) | 5 | 5 | 5 | 5 | 5 · | 5 | 15g/ha |
284 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
284(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
285 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
285(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
286 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
286(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
301 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
301 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
302 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
302(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
303 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
303(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
313 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
313(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
315 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
315(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
316 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
316(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
153
318 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
318(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
319 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
319(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
321 | 5 | 5 | 5 | 5 | 5 | 5 | 120g/ha |
321 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 120g/ha |
322 | 5 | 5 | 5 | 5 | 5 | 5 | 120g/ha |
322(R) | 5 | 5 | 5 | 5 | 5 | 5 | 120g/ha |
331 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
331 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
333 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
333(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
337 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
337(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
342 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
342(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
344 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
344(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
347 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
347(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
349 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
349(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
351 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
351 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
388 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
388(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
390 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
390(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
391 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
391(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
392 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
392(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
154
393 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
393(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
394 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
394(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
395 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
395(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
396 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
396(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
398 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
398(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
399 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
399(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
400 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
400(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
406 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
406(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
409 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
409(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
416 | 5 | 5 | 5 | 5 | 4 | 5 | 15g/ha |
416(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
419 | 5- | 5 | 5 | 5 | 5 | 5 | 15g/ha |
419(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
421 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
421 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
424 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
424(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
426 | 5 | 5 | 5 | 5 | 5 | 5 | 250g/ha |
426(R) | 5 | 5 | 5 | 5 | 5 | 5 | 250g/ha |
431 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
431 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
432 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
432(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
155
433 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
434 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
438 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
438(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
439 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
439(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
442 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
442(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
443 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
443(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
444 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
444(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
445 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
445(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
446 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
446(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
447 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
447(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
448 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
448(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
449 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
449(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
450 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
450(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
451 | N | N | N | N | N | 5 | 15g/ha |
451 (R) | N | N | N | N | N | 5 | 15g/ha |
452 | N | N | N | N | N | 5 | 15g/ha |
452(R) | N | N | N | N | N | 5 | 15g/ha |
453 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
453(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
454 | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
454(R) | 5 | 5 | 5 | 5 | 5 | 5 | 60g/ha |
156
455 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
455(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
456 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
456(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
462 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
462(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
463 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
463(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
469 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
471 | N | N | N | N | N | 5 | 15g/ha |
471 (R) | N | N | N | N | N | 5 | 15g/ha |
473 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
473(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
475 | N | N | N | N | N | 5 | 15g/ha |
475(R) | N | N | N | N | N | 5 | 15g/ha |
476 | N | N | N | N | N | 5 | 15g/ha |
476(R) | N | N | N | N | N | 5 | 15g/ha |
477 | N | N | N | N | N | 5 | 15g/ha |
477(R) | N | N | N | N | N | 5 | 15g/ha |
478 | N | N | N | N | N | 5 | 60g/ha |
478(R) | N | N | N | N | N | 5 | 60g/ha |
479 | N | N | N | N | N ' | 5 | 15g/ha |
480 | N | N | N | N | N | 5 | 15g/ha |
481 | N | N | N | N | N | 5 | 15g/ha |
481 (R) | N | N | N | N | N | 5 | 15g/ha |
485 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
486 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
487 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
488 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
489 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
490 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
491 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
157
491 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
493 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
494 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
495 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
495(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
496 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
497 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
498 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
498(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
499 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
499(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
500 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
500(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
501 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
501 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
502 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
502(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
503 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
503(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
504 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
504(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
511 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
692 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
730 | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
730(R) | 5 | 5 | 5 | 5 | 5 | 5 | 15g/ha |
881 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
885 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
919 | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
919(R) | 5 | 5 | 5 | 5 | 5 | 5 | 30g/ha |
Control compound A | 1 | 0 | 1 | 1 | 0 | 3 | 15g/ha |
158
Control compound B | 2 | 2 | 2 | 1 | 1 | 3 | 15g/ha |
Control compound C | 2 | 2 | 2 | 1 | 1 | 2 | 15g/ha |
Control compound D | 3 | 4 | 3 | 3 | 2 | N | 15g/ha |
Control compound E | 3 | 4 | 4 | 3 | 3 | N | 15g/ha |
Control compound F | 1 | 0 | 1 | 1 | 0 | 2 | 60g/ha |
Note: N represents untested;
Control compound A:
Control compound B: F3C
N.
cA
Control compound C: F3C
Control compound D: F3C
o
Control compound E: F3C
Control compound F: F3C
o
Table 3. Results of R configuration, S configuration and racemate on weeding effect in post-emergence stage
159
Compound NO. | Amaranthus retroflexus | Echinochloa cnisgalli | Eleusine indica | Dose |
1(R) | 5 | 4 | 5 | 7.5g/ha |
1 | 3 | 3 | 3 | 7.5g/ha |
1(S) | 1 | 1 | 1 | 7.5g/ha |
194(R) | 5 | 5 | 5 | 7.5g/ha |
194 | 5 | 4 | 4 | 7.5g/ha |
194(S) | 2 | 1 | 1 | 7.5g/ha |
Control compound D | 2 | 1 | 2 | 7.5g/ha |
Experiment on weed effect in pre-emergence stage:
The aforementioned seeds of monocotyledonous and dicotyledonous weeds and main crops were put into a plastic pot loaded with soil and covered with 0.5-2cm soil. The test compounds of the présent invention was dissolved with acetone, then added with tween 80, diluted by a 5 certain amount of water to reach a certain concentration, and sprayed immediately after sowing.
The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 500,250,125,60,30,15,7.5 g a.i./ha, especially to weeds such as Echinochloa cnisgalli, Digitaria sangiiinalis and Abutilon theophrasti, etc.. And many compounds had good 10 selectivity for corn, cotton, wheat, rice, soybean, and peanut etc.. In addition, evaluate the weed control effect with the above activity standard level. Many compounds show excellent activity and selectivity, which are shown in Table 4.
Table 4. Results on weeding effect in pre -emergence stage
Compou ndNO. | Veron ica didy ma Ténor e | Descu rainia sophia | Capsel la bursapastori s | Abutil on theoph rasti | Amara nthus retrofl exus | Setari a viridis | Corn | Cotton | So ybe ans | Pe an ut | Dose |
1(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
2(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
194(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 15g/ha |
194(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
194(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 60g/ha |
196(R) | 5 | . 5 | 5 | 5 | 5 | .5 | 0 | 0- - | 0 | 0 | 30g/ha |
198(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
199(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
208(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
160
212(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
216(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
218(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
239(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
246(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
248(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
249(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
253(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
258(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
264(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
283(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
301(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
315(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
333(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
349(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
398(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
421 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
431 (R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
432(R) | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
433 | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
434 | 5 | 5 | 5 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 30g/ha |
It is indicated from the experiment of main weeds in wheat and rice fields that the compound of the présent invention generally hâve good weed control efficacy. Above ail, it is noted that the compound of the invention hâve extremely high activity to broad-leaved weeds and cyperaceae weeds, which are résistant to ALS inhibitor, like Sagittaria trifolia, Scirpus juncoides, Cyperus diffbrmis, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine L., and Cyperus rotundus L., etc. , and hâve excellent commercial value.
Transplanted rice safety évaluation and weed control effect évaluation in rice field:
Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli,
Scirpus juncoides, Bidens tripartita L., Monochoria vaginalis, and Leptochloa chinensis were sowed and gently covered with soil, then left to stand still in greenhouse in the State of 0.5-lcm of water storage. The tuber of Sagittaria trifolia was planted in the next day or 2 days later. It was kept at 3-4cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common préparation method of the compounds of the présent invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Monochoria vaginalis, and
161
Leptochloa chinensis reached 0.5 leaf stage and Sagittaria trifolia reached the time point of primary leaf stage.
In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4cm depth. The 5 leaf stage rice (japonica rice) was transplanted at 3 cm of transplanting depth the next day. The compound of the présent invention was treated by the same way after 5 days of transplantation.
The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L„ Monochoria vaginalis, Leptochloa chinensis and Sagittaria trifolia 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with the above activity standard level. Many compounds show excellent activity and selectivity.
Table 5. Evaluation effect of some compounds
Compound NO. | Leptochloa chinensis | Scirpus juncoides | Monochoria vaginalis | Rice | Dose |
194(R) | 5 | 5 | 5 | 0 | 30 g/ha |
196(R) | 5 | 5 | 5 | 0 | 30 g/ha |
212(R) | 5 | 5 | 5 | 0 | 30 g/ha |
218(R) | 5 | 5 | 5 | 0 | 30 g/ha |
421 (R) | 5 | 5 | 5 | 0 | 30 g/ha |
434 | 5 | 5 | 5 | 0 | 30 g/ha |
Pyrazosulfuron-ethyl | 2 | 1 | 2 | 1 | 30 g/ha |
Note: The seeds of Echinochloa crusgalli, Scirpus juncoides, Monochoria vaginalis and Bidens tripartita L„ Sagittaria trifolia were collected from Heilongjiang Province of China. The tests indicated that the weeds were résistant to the common doses of Pyrazosulfuron-ethyl.
Composition activity test:
The active ingrédient B shuangzuocaotong, huanbifucaotong, benzuofucaotong, and sanzuohuangcaotong was produced by our company, the préparation methods of
purchased from reagent companies. The technical materials were ail dissolved in acetone and diluted with an aqueous solution containing 0.1% emulsifier Tween-80. The dilution is performed as required.
(1) Synthesis of Compound
162 (1.1) Cpd 1(3 g, 16 mmol, 1.0 eq), NaOH (0.72 g, 18 mmol, 1.1 eq) were added sequentially into 30 ml of DMF, and then Cpd 2 (1.28 g, 16.8 mmol, 1.05 eq) was added dropwise at 0 °C, and the reaction solution was stirred at 0 °C for 1 hour. When LCMS test showed that the reaction of raw materials was basically completed, there was one major new peak. The reaction solution was poured into 30 ml of water, and the mixture was separated, and the aqueous phase was extracted once with 50 ml of ethyl acetate, and the résultant organic phase was washed three times with saturated saline solution (50 ml), dried, evaporated to dryness under reduced pressure and separated by column chromatography to obtain Cpd 3 (3.6 g, 91% yield) (colorless oil).
CF3
Cpd 1
+ NaOH
DMF
Cpd 3 (1.2) Cpd 3(3.1 g, 13 mmol, 1.0 eq) was added to 30 ml of THF, then n-BuLi (6.42 ml, 2.5 M, 16 mmol, 1.2 eq) was slowly added at -78 °C, then the reaction solution was stirred at -78 °C for 0.5 hour, and slowly fed with CO2 for 10 minutes, then the reaction solution was slowly warmed to room température. The product was detected by LCMS. 20 ml of water was poured into the reaction solution, the mixture was separated, the aqueous phase was extracted once with 30 ml of ethyl acetate, and the résultant aqueous phase was gradually adjusted to pH = 4-5 with concentrated hydrochloric acid, filtered and dried to give Cpd 4(3.2 g, 87% yield) (white solid).
(1.3) Cpd 4(3.1 g, 11 mmol, 1.0 eq), Cpd 5 (1.66 g, 16.8 mmol, 1.5 eq), DMAP (0.13 g, 1.1 mmol, 0.1 eq) were sequentially added to 30 ml ofpyridine. Then, SOC12 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0 °C, and the reaction solution was stirred at room température for 3 hours. The product was detected by LCMS. Pyridine was removed by concentration, then 30 ml of water was poured into the reaction solution, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the résultant organic phase was washed three times with saturated saline solution (50 ml), dried, and evaporated to dryness under reduced pressure and separated by column chromatography to to obtain Cpd 6(2.5 g, 63% yield)
163 (white solid).
CF3
Cpd 4 Cpd 5 Cpd 6 (1.4) Cpd 6(1 g, 2.8 mmol, 1.0 eq) and m-CPBA (0.54 g, 3.1 mmol, 1.1 eq) were added sequentially in 10 mL of dichloromethane. The reaction solution was then stirred at room température for 1 hour. The product was detected by LCMS, and the reaction of raw materials was basically completed. The reaction solution was poured into 10 ml of water, the reaction was quenched with sodium hydrogen sulfite, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of dichloromethane, and the résultant organic phase was washed once with saturated saline solution (30 ml), dried, and evaporated to dryness under reduced pressure, and separated by column chromatography to give Cpd 7(0.85 g, 82% yield) (greyish white solid).
’H NMR (500 MHz, DMSO-îZ6) 12.57 (s, 1H), 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 7.82 (d, J =
8.0 Hz, 1H), 3.57-3.47 (m, 2H), 2.48 (s, 3H), 1.70-1.52 (m, 2H), 1.08-0.93 (m, 3H).
Cpd6 Cpd7 (1.5) Cpd 7 (0.5 g, 98% purity) was passed through chiral HP LC (Column: CHIRALPAK IG; Column Size: 3 cm x 25 cm, 5 um; Injection: 3.0 ml; Mobile phase: Hex(0.2% FA) : IPA=50:50; Flow rate: 28ml/min; Wavelength: UV 254nm; Température: 25°C; Sample solution: 70mg/ml in EtOH/DCM; Run time= 60 mins) for séparation, and then concentrated to obtain Cpd B1 (R-configuration)(0.16 g, Rt=l0.51min, 100% ee, purity 98%) in white solids, which were confirmed by single crystal diffraction.
164
Cpd 7
Cpd B1 (2) Synthesis of Compound
(2.1) Cpd a (0.5g, 2.13mmol), Cpd b (313mg, 2.55mmol), a catalytic amount of TBAB (lOmg), and DMF (lOmL) were added to a round-bottom flask, and stirred at room température 5 15 °C for 24 hr. When there was a small amount of raw materials remained according to LC-MS détection, a further treatment was made. The reaction solution was poured into 50mL of water, and extracted with methyl tert-butyl ether twice (50mL x 2). The organic phase was dried, concentrated, and separated by column chromatography, to obtain Cpd c (300mg, yield 50%), as a white solid.
O l0 Cpd a Cpd b Cpd c (2.2) Cpd c (0.3g, l.Oômmol), methanol (20mL) were added to a 100 mL single-port flask, lithium hydroxide (44.5mg, l.Oômmol) was dissolved in 2 mL of water, and slowly added dropwise to the single-port flask at room température, followed by stirring at room température for 12 hr. After completed reaction of the raw materials according to LC-MS détection, the reaction solution was adjusted with 0.5M dilute HCl to pH = 5-6, concentrated, and then extracted with water and ethyl acetate. The organic phase was dried, and concentrated to obtain Cpd d (200mg, yield 70%) as a white solid.
(2.3) Cpd d (200mg, 0.74mmol), Cpd e (75mg, 0.74mmol), DCC (152mg, 0.74mmol), and
165 anhydrous DCM (20mL) were added to a 100 mL round-bottom flask, and reacted at room température for 12 hr. After completed reaction of the raw materials according to LC-MS détection, the reaction solution was concentrated, and separated by column chromatography to obtain the Cpd B2 (200mg, yield 77%), as a white solid.
Cpd d Cpd e Cpd B2 ’H NMR (500 MHz, Chloroform-Y) δ 5.28 (q, J= 7.0 Hz, 1H), 5.15 (s, 2H), 4.27 - 4.07 (m, 3H), 3.91-3.73 (m, 2H), 2.04-1.82 (m, 3H), 1.66 (d, ./=7.0 Hz, 3H), 1.59-1.54 (m, 1H).
(A)Post-emergence treatment by performing foliage spray:
Weeds were cultivated by a pot culture method. A 180 xl40 mm plastic nutritional bowl contained 4/5 topsoil from the field was placed in an enamel pan, wherein the soil had been air-dried and screened and had an initial moisture content of 20%. Full and uniform weed seeds were selected, soaked in warm water at 25°C for 6 hours, and germinated in a 28°C biochemical incubator (darkness). The weed seeds that had just germinated were evenly placed on the surface of the soil and then covered with 0.5-1 cm soil according to the sizes of seeds.
The culture was carried out in a controllable sunlight greenhouse at 20 to 30°C, in naturel light, and relative humidity of 57% to 72%. The soil was loam with an organic matter content of 1.63%, a pH value of 7.1, an alkali-hydrolyzable nitrogen of 84.3 mg/kg, a rapidly available phosphores of 38.5 mg/kg, and a rapidly available potassium 82.1 mg/kg.
pots with 20 weed seeds per pot were treated in one treatment with 4 réplications per treatment.
The agents were used for only once in the experiment. In the stage of weeds with 1.5-2 leaves, the weeds were thinned out to maintain 10 weeds per pot and 30 weeds for each treatment, then continued to be cultured to Conyza Canadensis 10cm in height, other weeds 3-4 leaves stage and treated.
The well-cultured weeds were evenly placed on a platform with an area of 0.5m2, and a solution of agents was sprayed on the stems and leaves thereof by the 3WP-2000-type walking spray tower at a dosage of450kg/ha and at a spray pressure of 0.3MPa. After ail the solution was sprayed, the valve was closed. After 30 seconds, the door of the spray tower was opened, and the
166 nutritional bowl was taken ont. Then the valve was opened, and the spray tube was cleaned by spraying 50 ml of water. After the treatment, the weeds were routinely cultured in a greenhouse.
(B)Soil sealing treatment:
Weeds are cultivated in a controllable sunlight greenhouse at 20 to 30°C, in natural light, and relative humidity of 57% to 72%. The soil was loam with an organic matter content of 1.63%, a pH value of 7.1, an alkali-hydrolyzable nitrogen of 84.3 mg/kg, a rapidly available phosphores of 38.5 mg/kg, and a rapidly available potassium 82.1 mg/kg. The test soil was placed quantitatively to 3/4 of the pots and then watered from the bottom of the pots to completely wet the soil to saturation. The test weed seeds were germinated, and uniformly and quantitatively sowed on the surface, then covered with 0.5-2 cm soil according to the seed size, and ready-for use 72 hours after sowing.
pots with 30 weed seeds per pot were treated in one treatment with 4 réplications per treatment.
The well-sowed weeds were evenly placed on a platform with an area of 0.5m2, and a solution of agents was sprayed on the soil thereof by the 3WP-2000-type walking spray tower at a dosage of 450kg/ha and at a spray pressure of 0.3MPa. After ail the solution was sprayed, the valve was closed. After 30 seconds, the door of the spray tower was opened, and the nutritional bowl was taken out. Then the valve was opened, and the spray tube was cleaned by spraying 50 ml of water.
(C)Data investigation and statistical analysis:
A method for investigating absolute number was employed, wherein whole seedlings of survival weeds were eut off with a blade along the soil surface, and the fresh weight of the weeds was weighed with an analytical balance. For dead weeds, the fresh weight thereof was zéro.
The investigation was performed after 21 days of the treatment for only once.
Theoretical fresh weight inhibition rate of a combination of two active ingrédients in each group was calculated by the Gowing method (E0=X+Y-X*Y/100), and then compared with an actually measured inhibition rate (E), thereby effect of the combination (hereafter referred to as combined effect) on weeds was evaluated: the value of Ε-Ε0, which was greater than 10%, corresponded to a synergistic effect, the value of Ε-Ε0, which was less than -10%, corresponded to an antagonistic effect, and the value of Ε-Ε0, which was from -10% to 10%, corresponded to an additional effect. An optimum ratio of the two active ingrédients was determined by the actual
167 control effect, characteristics of herbicides, and balance of a corresponding formula. Wherein, in the formula, X represented the fresh weight inhibition rate of the active ingrédient A in a dosage of P, and Y represented the fresh weight inhibition rate of the active ingrédient B in a dosage of Q. The statistical results were shown in the table 6.
Table 6. Actual control effect and combined effect of a combination of A on weeds
Components | Weed | Foliag e / Soil F/S | Dose g a.i./ha | Ratio | Contro 1 effect (%) of A applie d alone (A) | Contro 1 effect (%) of B applie d alone (B) | Actual control effect of A+B (%) E(A+B) | Theoretic al control effect of A+B(%) E0(A+B) | E(A+B) -E0(A+ B) |
A+topramez one | Echino chloa caudat a Roshev | F | 1.5+7.5 | 1:5 | 65.9 | 38.5 | 93.5 | 79.0 | 14.5 |
A+isoxafluto le | Echino chloa caudat a Roshev | F | 1.5+15 | 1:10 | 65.9 | 41.3 | 91.9 | 80.0 | 11.9 |
A+tembotrio ne | Echino chloa caudat a Roshev | F | 1.5+15 | 1:10 | 65.9 | 31.7 | 88.3 | 76.7 | 11.6 |
A+tefuryltrio ne | Echino chloa caudat a Roshev | F | 1.5+30 | 1:20 | 65.9 | 21.5 | 86.6 | 73.2 | 13.4 |
A+shuangzu ocaotong | Echino chloa caudat a Roshev | F | 1.5+15 | 1:10 | 65.9 | 35.9 | 94.5 | 78.1 | 16.4 |
A+huanbifiic aotong | Echino chloa caudat a Roshev | F | 1.5+60 | 1:40 | 65.9 | 27.4 | 87.4 | 75.2 | 12.2 |
168
A+sanzuohu angcaotong | Echino chloa caudat a Roshev | F | 1.5+30 | 1:20 | 65.9 | 56.7 | 98.4 | 85.2 | 13.2 |
A+benzuofu caotong | Echino chloa caudat a Roshev | F | 1.5+15 | 1:10 | 65.9 | 25.2 | 89.9 | 74.5 | 15.4 |
A+CpdBl | Echino chloa caudat a Roshev | F | 1.5+7.5 | 1:5 | 65.9 | 47.8 | 96.2 | 82.2 | 14.0 |
A+glyphosat e | Cyper us rotund us | F | 7.5+300 | 1:40 | 52.4 | 19.4 | 82.4 | 61.6 | 20.8 |
A+glyphosat e | Conyz a Canad ensis | F | 45+450 | 1:10 | 75.6 | 51.2 | 100.0 | 88.1 | 11.9 |
A+glufosinat e ammonium | Cyper us serotin us | F | 15+300 | 1:20 | 47.3 | 23.1 | 90.2 | 59.5 | 30.7 |
A+glufosinat e ammonium | Conyz a Canad ensis | F | 45+300 | 3:20 | 75.6 | 57.8 | 100.0 | 89.7 | 10.3 |
A+glufosinat e-P-ammoni um | Cyper us serotin us | F | 15+150 | 1:10 | 47.3 | 21.4 | 85.3 | 58.6 | 26.7 |
A+paraquat dichloride | Cyper us diffor mis | F | 15+150 | 1:10 | 42.2 | 35.7 | 87.4 | 62.8 | 24.6 |
A+paraquat dichloride | Conyz a Canad ensis | F | 45+225 | 1:5 | 75.6 | 48.4 | 100.0 | 87.4 | 12.6 |
A+diquat dibromide monohydrate | Cyper us diffor mis | F | 15+300 | 1:20 | 42.2 | 18.4 | 79.2 | 52.8 | 26.4 |
169
A+diquat dibromide monohydrate | Conyz a Canad ensis | F | 45+300 | 3:20 | 75.6 | 37.8 | 100.0 | 84.8 | 15.2 |
A+flurtamon e | Capsel la bursapastori s | F | 0.75+75 | 1:100 | 48.3 | 56.7 | 95.4 | 77.6 | 17.8 |
A+diflufenic an | Capsel la bursapastori s | F | 0.75+75 | 1:100 | 48.3 | 33.1 | 86.7 | 65.4 | 21.3 |
A+picolinafe n | Capsel la bursapastori s | F | 0.75+45 | 1:60 | 48.3 | 44.4 | 91.5 | 71.3 | 20.2 |
A+clomazon e | Eleusi ne indica | F | 3+150 | 1:50 | 47.8 | 46.5 | 95.1 | 72.1 | 23.0 |
A+bixlozone | Eleusi ne indica | F | 3+180 | 1:60 | 47.8 | 36.7 | 88.8 | 67.0 | 21.8 |
A+tribenuro n-methyl | Malac hium aquati cum | F | 7.5+3 | 5:2 | 62.8 | 27.9 | 90.1 | 73.2 | 16.9 |
A+thifensulf uron methyl | Malac hium aquati cum | F | 7.5+4.5 | 5:3 | 62.8 | 30.8 | 87.2 | 74.3 | 12.9 |
A+pyrazosul furon-ethyl | Malac hium aquati cum | F | 7.5+7.5 | 1:1 | 62.8 | 35.7 | 89.5 | 76.1 | 13.4 |
A+thiencarb azone-methy 1 | Malac hium aquati cum | F | 7.5+3 | 5:2 | 62.8 | 41.1 | 93.3 | 78.1 | 15.2 |
A+halosulfur on methyl | Malac hium aquati cum | F | 7.5+9 | 5:6 | 62.8 | 36.4 | 94.7 | 76.3 | 18.4 |
A+rimsulfur on | Malac hium aquati cum | F | 7.5+1.5 | 5:1 | 62.8 | 26.2 | 92.4 | 72.5 | 19.9 |
A+nicosulfur on | Malac hium | F | 7.5+3 | 5:2 | 62.8 | 31.4 | 88.5 | 74.5 | 14.0 |
170
aquati cum | |||||||||
A+imazamo X | Malac hium aquati cum | F | 7.5+15 | 1:2 | 62.8 | 27.2 | 91.2 | 72.9 | 18.3 |
A+clethodim | Erioch loa villosa | F | 0.75+30 | 1:40 | 42.9 | 35.5 | 89.5 | 63.2 | 26.3 |
A+sethoxydi m | Erioch loa villosa | F | 0.75+45 | 1:60 | 42.9 | 36.7 | 92.3 | 63.9 | 28.4 |
A+quizalofo p-P-methyl | Erioch loa villosa | F | 0.75+15 | 1:20 | 42.9 | 41.7 | 87.3 | 66.7 | 20.6 |
A+oxyfluorf en | Lithos permit m arvens e | F | 3+60 | 1:20 | 63.5 | 31.5 | 91.4 | 75.0 | 16.4 |
A+oxadiazo n | Lithos permit m arvens e | F | 3+90 | 1:30 | 63.5 | 24.3 | 92.1 | 72.4 | 19.7 |
A+oxadiargy 1 | Lithos permit m arvens e | F | 3+30 | 1:10 | 63.5 | 38.7 | 89.8 | 77.6 | 12.2 |
A+sulfentraz one | Lithos permit m arvens e | F | 3+90 | 1:30 | 63.5 | 26.5 | 94.1 | 73.2 | 20.9 |
A+pyraclonil | Lithos permit m arvens e | F | 3+75 | 1:25 | 63.5 | 37.9 | 90.5 | 77.3 | 13.2 |
A+flumioxaz in | Lithos permu m arvens e | F | 3+7.5 | 2:5 | 63.5 | 29.4 | 92.4 | 74.2 | 18.2 |
A+saflufena cil | Lithos permu m arvens e | F | 3+0.75 | 4:1 | 63.5 | 39.7 | 98.4 | 78.0 | 20.4 |
A+carfentraz | Lithos | F | 3+4.5 | 2:3 | 63.5 | 27.2 | 89.3 | 73.4 | 15.9 |
171
one-ethyl | permit m arvens e | ||||||||
A+triiludimo xazin | Lithos permit m arvens e | F | 3+4,5 | 2:3 | 63.5 | 31.8 | 94.8 | 75.1 | 19.7 |
A+metribuzi n | Eclipta prostr aie | F | 0.75+15 | 1:20 | 59.2 | 36.3 | 89.3 | 74.0 | 15.3 |
A+terbuthyla zine | Eclipta prostr ate | F | 0.75+150 | 1:200 | 59.2 | 31.7 | 94.1 | 72.1 | 22.0 |
A+amicarba zone | Eclipta prostr ate | F | 0.75+60 | 1:80 | 59.2 | 43.7 | 90.7 | 77.0 | 13.7 |
A+chlorotol uron | Eclipta prostr ate | F | 0.75+225 | 1:300 | 59.2 | 24.5 | 86.2 | 69.2 | 17.0 |
A+isoprotur on | Eclipta prostr ate | F | 0.75+225 | 1:300 | 59.2 | 33.9 | 92.5 | 73.0 | 19.5 |
A+bromacil | Eclipta prostr ate | F | 0.75+450 | 1:600 | 59.2 | 28.4 | 83.9 | 70.8 | 13.1 |
A+propanil | Eclipta prostr ate | F | 0.75+300 | 1:400 | 59.2 | 21.7 | 93.8 | 68.1 | 25.7 |
A+desmedip ham | Eclipta prostr ate | F | 0.75+300 | 1:400 | 59.2 | 16.2 | 90.5 | 65.8 | 24.7 |
A+phenmedi pham | Eclipta prostr ate | F | 0.75+300 | 1:400 | 59.2 | 20.8 | 86.2 | 67.7 | 18.5 |
A+bentazone | Eclipta prostr ate | F | 0.75+150 | 1:200 | 59.2 | 30.2 | 88.4 | 71.5 | 16.9 |
A+bromoxy nil | Eclipta prostr ate | F | 0.75+60 | 1:80 | 59.2 | 41.2 | 92.6 | 76.0 | 16.6 |
A+butralin | Leptoc hloa chinen sis | S | 3+180 | 1:60 | 33.2 | 47.4 | 92.3 | 64.9 | 27.4 |
A+pendimet halin | Leptoc hloa chinen sis | S | 3+150 | 1:50 | 33.2 | 43.2 | 85.8 | 62.1 | 23.7 |
A+butachlor | | Descur | S | 3+225 | 1:75 | 40.2 | 42.2 | 92.3 | 65.4 | 26.9 |
172
ainia sophia | |||||||||
A+pretilachl or | Descur ainia sophia | S | 3+180 | 1:60 | 40.2 | 51.2 | 95.7 | 70.8 | 24.9 |
A+mefenace t | Descur ainia sophia | S | 3+150 | 1:50 | 40.2 | 46.4 | 89.6 | 67.9 | 21.7 |
A+s-metolac hlor | Descur ainia sophia | S | 3+150 | 1:50 | 40.2 | 31.3 | 94.3 | 58.9 | 35.4 |
A+flufenacet | Descur ainia sophia | S | 3+150 | 1:50 | 40.2 | 45.6 | 96.3 | 67.5 | 28.8 |
A+pyroxasul fone | Descur ainia sophia | S | 3+60 | 1:20 | 40.2 | 57.6 | 98.2 | 74.6 | 23.6 |
A+anilofos | Descur ainia sophia | S | 3+75 | 1:25 | 40.2 | 38.3 | 97.3 | 63.1 | 34.2 |
A+prosulfoc arb | Echino chloa crusga lli | S | 15+600 | 1:40 | 51.7 | 32.6 | 86.9 | 67.4 | 19.5 |
A+ Cpd B2 | Veroni ca didym a Tenore | F | 0.75+90 | 1:120 | 57.3 | 42.1 | 92.6 | 75.3 | 17.3 |
A+fluroxypy r | Veroni ca didym a Tenore | F | 0.75+60 | 1:80 | 57.3 | 39.3 | 90.3 | 74.1 | 16.2 |
A+florpyrau xifen benzyl | Veroni ca didym a Tenore | F | 0.75+15 | 1:20 | 57.3 | 50.3 | 91.5 | 78.8 | 12.7 |
A+halauxife n-methyl | Veroni ca didym a Tenore | F | 0.75+3 | 1:4 | 57.3 | 35.6 | 87.6 | 72.5 | 15.1 |
A+triclopyr | Veroni ca didym a Tenore | F | 0.75+90 | 1:120 | 57.3 | 34.2 | 91.5 | 71.9 | 19.6 |
A+clopyralid | Veroni ca | F | 0.75+45 | 1:60 | 57.3 | 28.9 | 83.3 | 69.6 | 13.7 |
173
didym a Tenore | |||||||||
A+picloram | Veroni ca didym a Tenore | F | 0.75+300 | 1:400 | 57.3 | 43.6 | 88.7 | 75.9 | 12.8 |
A+atninopyr alid | Veroni ca didym a Tenore | F | 0.75+30 | 1:40 | 57.3 | 32.2 | 90.2 | 71.0 | 19.2 |
A+dicamba | Veroni ca didym a Tenore | F | 0.75+150 | 1:200 | 57.3 | 29.7 | 87.3 | 70.0 | 17.3 |
A+2-methyl4-chlorophen oxyacetic acid | Veroni ca didym a Tenore | F | 0.75+150 | 1:200 | 57.3 | 39.3 | 90.9 | 74.1 | 16.8 |
A+2,4-dichlo rophenoxy acetic acid | Veroni ca didym a Tenore | F | 0.75+150 | 1:200 | 57.3 | 32.6 | 85.2 | 71.2 | 14.0 |
A+triaziflam | Amara nthus retrofl exus | S | 3+30 | 1:10 | 37.3 | 42.1 | 91.3 | 63.7 | 27.6 |
A+indazifla m | Amara nthus retrofl exus | S | 3+15 | 1:5 | 37.3 | 49.3 | 93.3 | 68.2 | 25.1 |
A+cinmethyl in | Lolium multifl orum Lamk. | S | 30+300 | 1:10 | 48.6 | 33.7 | 87.3 | 65.9 | 21.4 |
Note: The compound number represented by A is 194 (R).
In addition, the présent invention also provides other spécifie combinations of component A and component B, to further illustrate the composition of the présent invention. The compounds in the column Component A (Compound No.) are identified in Table 1. The second colùmn of
Table B1 lists spécifie compounds (for example topramezone in the first row) for component B. The remaining rows of Table B1 are similarly constructed.
Table Bl. List of ingrédients of the composition
174
Component A (Compound NO.) | Component B |
1 | topramezone |
1 | isoxaflutole |
1 | tembotrione |
1 | tefuryltrione |
1 | shuangzuocaotong |
1 | huanbifucaotong |
1 | sanzuohuangcaotong |
1 | benzuofucaotong |
1 | / o « \ // u. '•-ω O zx Ζ=Λ |
1 | glyphosate |
1 | glufosinate ammonium |
1 | glufosinate-P-ammonium |
1 | paraquat dichloride |
1 | diquat dibromide monohydrate |
1 | flurtamone |
1 | diflufenican |
1 | picolinafen |
1 | clomazone |
1 | bixlozone |
1 | tribenuron-methyl |
1 | thifensulfuron methyl |
1 | pyrazosulfuron-ethyl |
1 | thiencarbazone-methyl |
1 | halosulfiiron methyl |
1 | rimsulfuron |
1 | nicosulfuron |
1 | imazamox |
1 | clethodim |
1 | sethoxydim |
1 | quizalofop-P-methyl |
1 | oxyfluorfen |
1 | oxadiazon |
1 | oxadiargyl |
1 | sulfentrazone |
175
1 | pyraclonil |
1 | flumioxazin |
1 | saflufenacil |
1 | carfentrazone-ethyl |
1 | trifludimoxazin |
1 | metribuzin |
1 | terbuthylazine |
1 | amicarbazone |
1 | chlorotoluron |
1 | isoproturon |
1 | bromacil |
1 | propanil |
1 | desmedipham |
1 | phenmedipham |
1 | bentazone |
1 | bromoxynil |
1 | butralin |
1 | pendimethalin |
1 | butachlor |
1 | pretilachlor |
1 | mefenacet |
1 | s-metolachlor |
1 | flufenacet |
1 | pyroxasulfone |
1 | anilofos |
1 | prosulfocarb |
1 | H P )—\ NJ o Q A..... K |
1 | fluroxypyr |
1 | florpyrauxifen benzyl |
1 | halauxifen-methyl |
1 | triclopyr |
1 | clopyralid |
1 | picloram |
1 | aminopyralid |
1 | dicamba |
1 | 2-methyl-4-chlorophenoxyacetic |
176
acid | |
1 | 2,4-dichlorophenoxy acetic acid |
1 | triaziflam |
1 | indaziflam |
1 | cinmethylin |
Table B2 is constructed in the same way as that of Table B1 above, except for replacing the entries in the column “Component A (Compound No.)” with the corresponding entries in the column “Component A (Compound No.)” shown below. Therefore, for example, in Table B2, the entries in the column “Component A (Compound No.)” are ail expressed as “2” (that is, 5 Compound 2 identified in Table 1), and a mixture of Compound 2 and “topramezone” is specifically listed in the first row under the heading of Table B2. Tables B3 to B547 are similarly constructed.
Table | Component A (Compound NO.) column entry | Table | Component A (Compound NO.) column entry | Table | Component A (Compound NO.) column entry | Table | Component A (Compound NO.) column entry |
B2 | 2 | B3 | 3 | B4 | 4 | B5 | 5 |
B6 | 6 | B7 | 7 | B8 | 8 | B9 | 9 |
B10 | 10 | Bll | 11 | B12 | 12 | B13 | 13 |
B14 | 14 | B15 | 15 | B16 | 16 | B17 | 17 |
B18 | 18 | B19 | 19 | B20 | 20 | B21 | 21 |
B22 | 22 | B23 | 23 | B24 | 24 | B25 | 25 |
B26 | 26 | B27 | 27 | B28 | 28 | B29 | 29 |
B30 | 30 | B31 | 31 | B32 | 32 | B33 | 33 |
B34 | 34 | B35 | 35 | B36 | 36 | B37 | 37 |
B38 | 38 | B39 | 39 | B40 | 40 | B41 | 41 |
B42 | 42 | B43 | 43 | B44 | 44 | B45 | 45 |
B46 | 46 | B47 | 47 | B48 | 48 | B49 | 49 |
B50 | 50 | B51 | 51 | B52 | 52 | B53 | 53 |
B54 | 54 | B55 | 55 | B56 | 56 | B57 | 57 |
B58 | 58 | B59 | 59 | B60 | 60 | B61 | 61 |
B62 | 62 | B63 | 63 | B64 | 64 | B65 | 65 |
B66 | 66 | B67 | 67 | B68 | 68 | B69 | 69 |
177
B70 | 70 | B71 | 71 | B72 | 72 | B73 | 73 |
B74 | 74 | B75 | 75 | B76 | 76 | B77 | 77 |
B78 | 78 | B79 | 79 | B80 | 80 | B81 | 81 |
B82 | 82 | B83 | 83 | B84 | 84 | B85 | 85 |
B86 | 86 | B87 | 87 | B88 | 88 | B89 | 89 |
B90 | 90 | B91 | 91 | B92 | 92 | B93 | 93 |
B94 | 94 | B95 | 95 | B96 | 96 | B97 | 97 |
B98 | 98 | B99 | 99 | B100 | 100 | B101 | 101 |
B102 | 102 | B103 | 103 | B104 | 104 | B105 | 105 |
B106 | 106 | B107 | 107 | B108 | 108 | B109 | 109 |
B110 | 110 | Bill | 111 | B112 | 112 | B113 | 113 |
B114 | 114 | B115 | 115 | B116 | 116 | B117 | 117 |
B118 | 118 | B119 | 119 | B120 | 120 | B121 | 121 |
B122 | 122 | B123 | 123 | B124 | 124 | B125 | 125 |
B126 | 126 | B127 | 127 | B128 | 128 | B129 | 129 |
B130 | 130 | B131 | 131 | B132 | 132 | B133 | 133 |
B134 | 134 | B135 | 135 | B136 | 136 | B137 | 137 |
B138 | 138 | B139 | 139 | B140 | 140 | B141 | 141 |
B142 | 142 | B143 | 143 | B144 | 144 | B145 | 145 |
B146 | 146 | B147 | 147 | B148 | 148 | B149 | 149 |
B150 | 150 | B151 | 151 | B152 | 152 | B153 | 153 |
B154 | 154 | B155 | 155 | B156 | 156 | B157 | 157 |
B158 | 158 | B159 | 159 | B160 | 160 | B161 | 161 |
B162 | 162 | B163 | 163 | B164 | 164 | B165 | 165 |
B166 | 166 | B167 | 167 | B168 | 168 | B169 | 169 |
B170 | 170 | B171 | 171 | B172 | 172 | B173 | 173 |
B174 | 174 | B175 | 175 | B176 | 176 | B177 | 177 |
B178 | 178 | B179 | 179 | B180 | 180 | B181 | 181 |
B182 | 182 | B183 | 183 | B184 | 184 | B185 | 185 |
B186 | 186 | B187 | 187 | B188 | 188 | B189 | 189 |
B190 | 190 | B191 | 191 | B192 | 192 | B193 | 193 |
B194 | 194 | B195 | 195 | B196 | 196 | B197 | 197 |
B198 | 198 | B199 | 199 | B200 | 200 | B201 | 201 |
B202 | 202 | B203 | 203 | B204 | 204 | B205 | 205 |
B206 | 206 | B207 | 207 | B208 | 208 | B209 | 209 |
B210 | 210 | B211 | 211 | B212 | 212 | B213 | 213 |
B214 | 214 | B215 | 215 | B216 | 216 | B217 | 217 |
178
B218 | 218 | B219 | 219 | B220 | 220 | B221 | 221 |
B222 | 222 | B223 | 223 | B224 | 224 | B225 | 225 |
B226 | 226 | B227 | 227 | B228 | 228 | B229 | 229 |
B230 | 230 | B231 | 231 | B232 | 232 | B233 | 233 |
B234 | 234 | B235 | 235 | B236 | 236 | B237 | 237 |
B238 | 238 | B239 | 239 | B240 | 240 | B241 | 241 |
B242 | 242 | B243 | 243 | B244 | 244 | B245 | 245 |
B246 | 246 | B247 | 247 | B248 | 248 | B249 | 249 |
B250 | 250 | B251 | 251 | B252 | 252 | B253 | 253 |
B254 | 254 | B255 | 255 | B256 | 256 | B257 | 257 |
B258 | 258 | B259 | 259 | B260 | 260 | B261 | 261 |
B262 | 262 | B263 | 263 | B264 | 264 | B265 | 265 |
B266 | 266 | B267 | 267 | B268 | 268 | B269 | 269 |
B270 | 270 | B271 | 271 | B272 | 272 | B273 | 273 |
B274 | 274 | B275 | 275 | B276 | 276 | B277 | 277 |
B278 | 278 | B279 | 279 | B280 | 280 | B281 | 281 |
B282 | 282 | B283 | 283 | B284 | 284 | B285 | 285 |
B286 | 286 | B287 | 287 | B288 | 288 | B289 | 289 |
B290 | 290 | B291 | 291 | B292 | 292 | B293 | 293 |
B294 | 294 | B295 | 295 | B296 | 296 | B297 | 297 |
B298 | 298 | B299 | 299 | B300 | 300 | B301 | 301 |
B302 | 302 | B303 | 303 | B304 | 304 | B305 | 305 |
B306 | 306 | B307 | 307 | B308 | 308 | B309 | 309 |
B310 | 310 | B311 | 311 | B312 | 312 | B313 . | 313 |
B314 | 314 | B315 | 315 | B316 | 316 | B317 | 317 |
B318 | 318 | B319 | 319 | B320 | 320 | B321 | 321 |
B322 | 322 | B323 | 323 | B324 | 324 | B325 | 325 |
B326 | 326 | B327 | 327 | B328 | 328 | B329 | 329 |
B330 | 330 | B331 | 331 | B332 | 332 | B333 | 333 |
B334 | 334 | B335 | 335 | B336 | 336 | B337 | 337 |
B338 | 338 | B339 | 339 | B340 | 340 | B341 | 341 |
B342 | 342 | B343 | 343 | B344 | 344 | B345 | 345 |
B346 | 346 | B347 | 347 | B348 | 348 | B349 | 349 |
B350 | 350 | B351 | 351 | B352 | 352 | B353 | 353 |
B354 | 354 | B355 | 355 | B356 | 356 | B357 | 357 |
B358 | 358 | B359 | 359 | B360 | 360 | B361 | 361 |
B362 | 362 | B363 | 363 | B364 | 364 | B365 | 365 |
179
B366 | 366 | B367 | 367 | B368 | 368 | B369 | 369 |
B370 | 370 | B371 | 371 | B372 | 372 | B373 | 373 |
B374 | 374 | B375 | 375 | B376 | 376 | B377 | 377 |
B378 | 378 | B379 | 379 | B380 | 380 | B381 | 381 |
B382 | 382 | B383 | 383 | B384 | 384 | B385 | 385 |
B386 | 386 | B387 | 387 | B388 | 388 | B389 | 389 |
B390 | 390 | B391 | 391 | B392 | 392 | B393 | 393 |
B394 | 394 | B395 | 395 | B396 | 396 | B397 | 397 |
B398 | 398 | B399 | 399 | B400 | 400 | B401 | 401 |
B402 | 402 | B403 | 403 | B404 | 404 | B405 | 405 |
B406 | 406 | B407 | 407 | B408 | 408 | B409 | 409 |
B410 | 410 | B411 | 411 | B412 | 412 | B413 | 413 |
B414 | 414 | B415 | 415 | B416 | 416 | B417 | 417 |
B418 | 418 | B419 | 419 | B420 | 420 | B421 | 421 |
B422 | 422 | B423 | 423 | B424 | 424 | B425 | 425 |
B426 | 426 | B427 | 427 | B428 | 428 | B429 | 429 |
B430 | 430 | B431 | 431 | B432 | 432 | B433 | 433 |
B434 | 434 | B435 | 435 | B436 | 436 | B437 | 437 |
B438 | 438 | B439 | 439 | B440 | 440 | B441 | 441 |
B442 | 442 | B443 | 443 | B444 | 444 | B445 | 445 |
B446 | 446 | B447 | 447 | B448 | 448 | B449 | 449 |
B450 | 450 | B451 | 451 | B452 | 452 | B453 | 453 |
B454 | 454 | B455 | 455 | B456 | 456 | B457 | 457 |
B458 | 458 | B459 | 459 | B460 | 460 | B461 | 461 |
B462 | 462 | B463 | 463 | B464 | 464 | B465 | 465 |
B466 | 466 | B467 | 467 | B468 | 468 | B469 | 469 |
B470 | 470 | B471 | 471 | B472 | 472 | B473 | 473 |
B474 | 474 | B475 | 475 | B476 | 476 | B477 | 477 |
B478 | 478 | B479 | 479 | B480 | 480 | B481 | 481 |
B482 | 482 | B483 | 483 | B484 | 484 | B485 | 485 |
B486 | 486 | B487 | 487 | B488 | 488 | B489 | 489 |
B490 | 490 | B491 | 491 | B492 | 492 | B493 | 493 |
B494 | 494 | B495 | 495 | B496 | 496 | B497 | 497 |
B498 | 498 | B499 | 499 | B500 | 500 | B501 | 501 |
B502 | 502 | B503 | 503 | B504 | 504 | B505 | 505 |
B506 | 506 | B507 | 507 | B508 | 508 | B509 | 509 |
B510 | 510 | B511 | 511 | B512 | 512 | B513 | 513 |
180
B514 | 514 | B515 | 515 | B516 | 516 | B517 | 517 |
B518 | 518 | B519 | 519 | B520 | 520 | B521 | 521 |
B522 | 522 | B523 | 523 | B524 | 524 | B525 | 525 |
B526 | 526 | B527 | 527 | B528 | 528 | B529 | 529 |
B530 | 530 | B531 | 531 | B532 | 532 | B533 | 533 |
B534 | 534 | B535 | 535 | B536 | 536 | B537 | 537 |
B538 | 538 | B539 | 539 | B540 | 540 | B541 | 541 |
B542 | 542 | B543 | 543 | B544 | 544 | B545 | 545 |
B546 | 546 | B547 | 547 | B548 | 692 | B549 | 730 |
B550 | 881 | B551 | 885 | B552 | 919 |
Table Cl is constructed in the same way as that of Table B1 above, except for replacing the entries in the column “Component A (Compound No.)” with the corresponding entries in the column “Component A (Compound No.)” shown below. Therefore, for example, in Table Cl, the entries in the column “Component A (Compound No.)” are ail expressed as “1(R)” (that is, the R configuration of Compound 1 identified in Table A), and a mixture of Compound 1(R) and “topramezone” is specifically listed in the first row under the heading of Table Cl. Tables C2 to
C532 are similarly constructed.
Table | Component A (Compound NO.) column entry | Table | Component A (Compound NO.) column entry | Table | Component A (Compound NO.) column entry | Table | Component A (Compound NO.) column entry |
C2 | 2(R) | C3 | 3(R) | C4 | 4(R) | C5 | 5(R) |
C6 | 6(R) | C7 | 7(R) | C8 | 8(R) | C9 | 9(R) |
CIO | 10(R) | Cil | 11(R) | C12 | 12(R) | C13 | 13(R) |
C14 | 14(R) | C15 | 15(R) | C16 | 16(R) | C17 | 17(R) |
C18 | 18(R) | C19 | 19(R) | C20 | 20(R) | C21 | 21 (R) |
C22 | 22(R) | C23 | 23(R) | C24 | 24(R) | C25 | 25(R) |
C26 | 26(R) | C27 | 27(R) | C28 | 28(R) | C29 | 29(R) |
C30 | 30(R) | C31 | 31(R) | C32 | 32(R) | C33 | 33(R) |
C34 | 34(R) | C35 | 35(R) | C36 | 36(R) | C37 | 37(R) |
C38 | 38(R) | C39 | 39(R) | C40 | 40(R) | C41 | 41(R) |
C42 | 42(R) | C43 | 43(R) | C44 | 44(R) | C45 | 45(R) |
C46 | 46(R) | C47 | 47(R) | C48 | 48(R) | C49 | 49(R) |
C50 | 50(R) | C51 | 51(R) | C52 | 52(R) | C53 | 53(R) |
C54 | 54(R) | C55 | 55(R) | C56 | 56(R) | C57 | 57(R) |
181
C58 | 58(R) | C59 | 59(R) | C60 | 60(R) | C61 | 61(R) |
C62 | 62(R) | C63 | 63(R) | C64 | 64(R) | C65 | 65(R) |
C66 | 66(R) | C67 | 67(R) | C68 | 68(R) | C69 | 69(R) |
C70 | 70(R) | C71 | 71 (R) | C72 | 72(R) | C73 | 73(R) |
C74 | 74(R) | C75 | 75(R) | C76 | 76(R) | C77 | 77(R) |
C78 | 78(R) | C79 | 79(R) | C80 | 80(R) | C81 | 81 (R) |
C82 | 82(R) | C83 | 83(R) | C84 | 84(R) | C85 | 85(R) |
C86 | 86(R) | C87 | 87(R) | C88 | 88(R) | C89 | 89(R) |
C90 | 90(R) | C91 | 91(R) | C92 | 92(R) | C93 | 93(R) |
C94 | 94(R) | C95 | 95(R) | C96 | 96(R) | C97 | 97(R) |
C98 | 98(R) | C99 | 99(R) | C100 | 100(R) | C101 | 101(R) |
C102 | 102(R) | C103 | 103(R) | C104 | 104(R) | C105 | 105(R) |
C106 | 106(R) | C107 | 107(R) | C108 | 108(R) | C109 | 109(R) |
C110 | 110(R) | cm | lll(R) | C112 | 112(R) | C113 | 113(R) |
C114 | 114(R) | C115 | 115(R) | C116 | 116(R) | C117 | 117(R) |
C118 | 118(R) | C119 | 119(R) | C120 | 120(R) | C121 | 121(R) |
C122 | 122(R) | C123 | 123(R) | C124 | 124(R) | C125 | 125(R) |
C126 | 126(R) | C127 | 127(R) | C128 | 128(R) | C129 | 129(R) |
C130 | 130(R) | C131 | 131(R) | C132 | 132(R) | C133 | 133(R) |
C134 | 134(R) | C135 | 135(R) | C136 | 136(R) | C137 | 137(R) |
C138 | 138(R) | C139 | 139(R) | C140 | 140(R) | C141 | 141(R) |
C142 | 142(R) | C143 | 143(R) | C144 | 144(R) | C145 | 145(R) |
C146 | 146(R) | C147 | 147(R) | C148 | 148(R) | C149 | 149(R) |
C150 | 150(R) | C151 | 151(R) | C152 | 152(R) | C153 | 153(R) |
C154 | 154(R) | C155 | 155(R) | C156 | 156(R) | C157 | 157(R) |
C158 | 158(R) | C159 | 159(R) | C160 | 160(R) | C161 | 161(R) |
C162 | 162(R) | C163 | 163(R) | C164 | 164(R) | C165 | 165(R) |
C166 | 166(R) | C167 | 167(R) | C168 | 168(R) | C169 | 169(R) |
C170 | 170(R) | C171 | 171(R) | C172 | 172(R) | C173 | 173(R) |
C174 | 174(R) | C175 | 175(R) | C176 | 176(R) | C177 | 177(R) |
C178 | 178(R) | C179 | 179(R) | C180 | 180(R) | C181 | 181(R) |
C182 | 182(R) | C183 | 183(R) | C184 | 184(R) | C185 | 185(R) |
C186 | 186(R) | C187 | 187(R) | C188 | 188(R) | C189 | 193(R) |
C190 | 547(R) | C191 | 195(R) | C192 | 196(R) | C193 | 197(R) |
C194 | 198(R) | C195 | 199(R) | C196 | 200(R) | C197 | 201 (R) |
C198 | 202(R) | C199 | 203 (R) | C200 | 204(R) | C201 | 205(R) |
C202 | 206(R) | C203 | 207(R) | C204 | 208(R) | C205 | 209(R) |
182
C206 | 210(R) | C207 | 211(R) | C208 | 212(R) | C209 | 213(R) |
C210 | 214(R) | C211 | 215(R) | C212 | 216(R) | C213 | 217(R) |
C214 | 218(R) | C215 | 219(R) | C216 | 220(R) | C217 | 221 (R) |
C218 | 222(R) | C219 | 223(R) | C220 | 224(R) | C221 | 225(R) |
C222 | 226(R) | C223 | 227(R) | C224 | 228(R) | C225 | 229(R) |
C226 | 230(R) | C227 | 231 (R) | C228 | 232(R) | C229 | 233(R) |
C230 | 234(R) | C231 | 235(R) | C232 | 236(R) | C233 | 237(R) |
C234 | 238(R) | C235 | 239(R) | C236 | 240(R) | C237 | 241 (R) |
C238 | 242(R) | C239 | 243(R) | C240 | 244(R) | C241 | 245(R) |
C242 | 246(R) | C243 | 247(R) | C244 | 248(R) | C245 | 249(R) |
C246 | 250(R) | C247 | 251 (R) | C248 | 252(R) | C249 | 253(R) |
C250 | 254(R) | C251 | 255(R) | C252 | 256(R) | C253 | 257(R) |
C254 | 258(R) | C255 | 259(R) | C256 | 260(R) | C257 | 261 (R) |
C258 | 262(R) | C259 | 263(R) | C260 | 264(R) | C261 | 265(R) |
C262 | 266(R) | C263 | 267(R) | C264 | 268(R) | C265 | 269(R) |
C266 | 270(R) | C267 | 271 (R) | C268 | 272(R) | C269 | 273(R) |
C270 | 274(R) | C271 | 275(R) | C272 | 276(R) | C273 | 277(R) |
C274 | 278(R) | C275 | 279(R) | C276 | 280(R) | C277 | 281 (R) |
C278 | 282(R) | C279 | 283(R) | C280 | 284(R) | C281 | 285(R) |
C282 | 286(R) | C283 | 287(R) | C284 | 288(R) | C285 | 289(R) |
C286 | 290(R) | C287 | 291 (R) | C288 | 292(R) | C289 | 293(R) |
C290 | 294(R) | C291 | 295(R) | C292 | 296(R) | C293 | 297(R) |
C294 | 298(R) | C295 | 299(R) | C296 | 300(R) | C297 | 301(R) |
C298 | 302(R) | C299 | 303(R) | C300 | 304(R) | C301 | 305(R) |
C302 | 306(R) | C303 | 307(R) | C304 | 308(R) | C305 | 309(R) |
C306 | 310(R) | C307 | 311(R) | C308 | 312(R) | C309 | 313(R) |
C310 | 314(R) | C311 | 315(R) | C312 | 316(R) | C313 | 317(R) |
C314 | 318(R) | C315 | 319(R) | C316 | 320(R) | C317 | 321 (R) |
C318 | 322(R) | C319 | 323(R) | C320 | 324(R) | C321 | 325(R) |
C322 | 326(R) | C323 | 327(R) | C324 | 328(R) | C325 | 329(R) |
C326 | 330(R) | C327 | 331 (R) | C328 | 332(R) | C329 | 333(R) |
C330 | 334(R) | C331 | 335(R) | C332 | 336(R) | C333 | 337(R) |
C334 | 338(R) | C335 | 339(R) | C336 | 340(R) | C337 | 341 (R) |
C338 | 342(R) | C339 | 343(R) | C340 | 344(R) | C341 | 345(R) |
C342 | 346(R) | C343 | 347(R) | C344 | 348(R) | C345 | 349(R) |
C346 | 350(R) | C347 | 351 (R) | C348 | 352(R) | C349 | 353(R) |
C350 | 354(R) | C351 | 355(R) | C352 | 356(R) | C353 | 357(R) |
183
C354 | 358(R) | C355 | 359(R) | C356 | 360(R) | C357 | 361(R) |
C358 | 362(R) | C359 | 363(R) | C360 | 364(R) | C361 | 365(R) |
C362 | 366(R) | C363 | 367(R) | C364 | 368(R) | C365 | 369(R) |
C366 | 370(R) | C367 | 371 (R) | C368 | 372(R) | C369 | 373(R) |
C370 | 374(R) | C371 | 375(R) | C372 | 376(R) | C373 | 377(R) |
C374 | 378(R) | C375 | 379(R) | C376 | 380(R) | C377 | 381 (R) |
C378 | 382(R) | C379 | 383(R) | C380 | 384(R) | C381 | 385(R) |
C382 | 386(R) | C383 | 387(R) | C384 | 388(R) | C385 | 389(R) |
C386 | 390(R) | C387 | 391(R) | C388 | 392(R) | C389 | 393(R) |
C390 | 394(R) | C391 | 395(R) | C392 | 396(R) | C393 | 397(R) |
C394 | 398(R) | C395 | 399(R) | C396 | 400(R) | C397 | 401 (R) |
C398 | 402(R) | C399 | 403(R) | C400 | 404(R) | C401 | 405(R) |
C402 | 406(R) | C403 | 407(R) | C404 | 408(R) | C405 | 409(R) |
C406 | 410(R) | C407 | 411(R) | C408 | 412(R) | C409 | 413(R) |
C410 | 414(R) | C411 | 415(R) | C412 | 416(R) | C413 | 417(R) |
C414 | 418(R) | C415 | 419(R) | C416 | 420(R) | C417 | 421 (R) |
C418 | 422(R) | C419 | 423(R) | C420 | 424(R) | C421 | 425(R) |
C422 | 426(R) | C423 | 427(R) | C424 | 428(R) | C425 | 429(R) |
C426 | 430(R) | C427 | 431 (R) | C428 | 432(R) | C429 | 438(R) |
C430 | 439(R) | C431 | 503(R) | C432 | 441 (R) | C433 | 442(R) |
C434 | 443(R) | C435 | 444(R) | C436 | 445(R) | C437 | 446(R) |
C438 | 447(R) | C439 | 448(R) | C440 | 449(R) | C441 | 450(R) |
C442 | 451 (R) | C443 | 452(R) | C444 | 453(R) | C445 | 454(R) |
C446 | 455(R) | C447 | 456(R) | C448 | 457(R) | C449 | 458(R) |
C450 | 459(R) | C451 | 460(R) | C452 | 461 (R) | C453 | 462(R) |
C454 | 463(R) | C455 | 464(R) | C456 | 465(R) | C457 | 466(R) |
C458 | 467(R) | C459 | 468(R) | C460 | 469(R) | C461 | 508(R) |
C462 | 471 (R) | C463 | 472(R) | C464 | 473(R) | C465 | 474(R) |
C466 | 475(R) | C467 | 476(R) | C468 | 477(R) | C469 | 478(R) |
C470 | 533(R) | C471 | 542(R) | C472 | 481 (R) | C473 | 482(R) |
C474 | 483(R) | C475 | 484(R) | C476 | 543(R) | C477 | 486(R) |
C478 | 487(R) | C479 | 488(R) | C480 | 489(R) | C481 | 490(R) |
C482 | 491 (R) | C483 | 492(R) | C484 | 493(R) | C485 | 692(R) |
C486 | 495(R) | C487 | 496(R) | C488 | 497(R) | C489 | 498(R) |
C490 | 499(R) | C491 | 500(R) | C492 | 501 (R) | C493 | 502(R) |
C494 | 504(R) | C495 | 505(R) | C496 | 506(R) | C497 | 507(R) |
C498 | 509(R) | C499 | 510(R) | C500 | 511(R) | C501 | 512(R) |
184
C502 | 513(R) | C503 | 514(R) | C504 | 515(R) | C505 | 516(R) |
C506 | 517(R) | C507 | 518(R) | C508 | 519(R) | C509 | 520(R) |
C510 | 521 (R) | C511 | 522(R) | C512 | 523(R) | C513 | 524(R) |
C514 | 525(R) | C515 | 526(R) | C516 | 527(R) | C517 | 528(R) |
C518 | 529(R) | C519 | 530(R) | C520 | 531 (R) | C521 | 532(R) |
C522 | 534(R) | C523 | 535(R) | C524 | 536(R) | C525 | 537(R) |
C526 | 538(R) | C527 | 539(R) | C528 | 540(R) | C529 | 541 (R) |
C530 | 544(R) | C531 | 545(R) | C532 | 730(R) | Cl | 1(R) |
C533 | 881 (R) | C534 | 885(R) | C535 | 919(R) |
At the same time, it is found after several tests that the compounds and compositions of the présent invention hâve good selectivity to many gramineae grasses such as zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and are able to control many important grass weeds and broad-leaved weeds. The compounds also show excellent selectivity and commercial value in the tests on sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods.
Claims (16)
1. A carboxylic acid derivative-substituted iminoaryl compound, represented by general formula I’:
Â/XN'Y'XYOH
Q Μ X3 η
O □ ’
Û2 Ç?4 t Q4 Ri'n^nV R8>| nV
Q-jii^'N'^Q3 R7 R? R7 θ5
Q represents R2 , R6 or R6 ;
Y represents halogen, haloalkyl or cyano;
Z represents halogen;
M represents CH or N;
X represents -CXiX2-(alkyl)n-, -alkyl-CXiX2-(alkyl)n- or -(CH2)r-;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkyl carbonyl, alkoxy carbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclic alkyl, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “cycloalkyl”, “cycloalkylalkyl”, “aryl”, “heterocyclyl”, “arylalkyl” and “heterocyclic alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3> -N(Ri3)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring; and Xb X2 are not hydrogen at the same time;
X3 represents O, S, NH or N-alkyl;
Qb Q2, Q.b Q4, Qs each independently represent O or S;
Ri, R2 each independently represent H, cyano, alkyl, alkenyl, alkynyl, formyl alkyl, cyanoalkyl, amino, aminoalkyl, amino carbonyl, amino carbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl,
186
R4R5N-(CO)-NR3-, a , R3-S(O)m-(alkyl)n-, R3-O-(alkyl)n-, R3-(CO)-(alkyl)n-, R3-O-(alkyl)n-(CO)-, R3-(CO)-O-(alkyl)n-, R3-S-(CO)-(alkyl)n-, R3-O-(CO)-alkyl- or R3-O-(CO)-O-alkyl-, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “amino”, “aminoalkyl”, “amino carbonyl”, “amino carbonylalkyl” and “aminosulfonyl” are each independently unsubstituted or substituted by one or two groups selected from -Ru, -ORii, -(CO)Rn, -(CO)ORh, -alkyl-(CO)ORn, -(SO2)Rn, -(SO2)ORn, -alkyl-(SO2)Rn, -(CO)N(R12)2 and -(SO2)N(R12)2, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -ORi3, -SRi3, -(CO)ORi3, -(SO2)Ri3, -N(Rj3)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
R6 represents alkyl, alkenyl, alkynyl or cyano, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, alkoxy and alkoxy carbonyl;
R7, R7’, Rg, Rg’ each independently represent H, alkyl, halogen, haloalkyl, amino, hydroxyalkyl or alkoxy;
R3, R4, R5 each independently represent H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -ORi3, -SRi3, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-alkyl-(CO)ORi3, or two
187 adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2or -OCH2O- form a fused ring;
Ru independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, benzyl, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “phenyl” and “benzyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;
R12 independently represents H, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or N(R]2)2 in -(CO)N(Ri2)2 or -(SO2)N(Ri2)2 each independently represents unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;
Rb independently represents H, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;
r represents an integer of 2 or more; m represents 0, 1 or 2; n independently represents 0 or 1;
the dérivative means that the carboxylic acid functional group in the general formula is changed into any ester, acylhydrazide, imidate, thioimidate, amidine, amide, orthoester, acyl cyanide, acyl halide, thioester, thionoester, dithiolester, nitrile or any other carboxylic acid dérivative.
2. The carboxylic acid derivative-substituted iminoaryl compound according to claim 1, which is characterized in that the compound is represented by general formula I:
x4 wherein, W represents OX5, SX5 or N(Xs)2;
X3, X4 each independently represent O, S, NH or N-alkyl;
X5 represents H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl,
188 o X13'N-Xl4 ν$γΧΐ3 \-Νγχΐ3 ,χ^/ΟΧ ° Χ14 , Χΐ4 or ο , wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano,
O O nitro, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, * xn, 1 xn, X X11/O Xn, o
A x Λ·'*3 ΐΝγχ’3 Ά χ” An t x’!
Χυ 11 s o , X14 , Xi4 , X14 and Xi4 ,the“cycloalkyl”, “cycloalkenyl”, “heterocyclyl” and “aryl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
^N^X13 or N(Xs)2 represents X14 or unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;
Xi 1 independently represents H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl or Q wherein, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and
-O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Xi2 independently represents alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “heterocyclyl”, “heterocyclic alkyl”, “aryl” and “arylalkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl,
189 alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORb, -(SO2)Rb, -N(Rb)2 and -O-alkyl-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X13, X14 each independently represent H, halogen, cyano, alkoxy, alkoxyalkyl, alkyl carbonyl, alkoxy carbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, aryl, arylalkyl, heterocyclyl or heterocyclic alkyl, or C, X13, X14, taken together, form unsubstituted or substituted cyclic structure, or N, X13, X14, taken together, form unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position, wherein, the “alkyl”, “alkenyl” and “alkynyl” are each independently unsubstituted or substituted by halogen, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenyl alkyl”, “aryl”, “arylalkyl”, “heterocyclyl” and “heterocyclic alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-alkyl-(CO)OR]3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2Oform a fused ring.
3. The carboxylic acid derivative-substituted iminoaryl compound according to claim 1 or 2, which is characterized in that,
Y represents halogen, halo C1-C8 alkyl or cyano;
X represents -CXiX2-(C1-C8 alkyl)n-, -(C1-C8 alkyl)-CXiX2-(Cl-C8 alkyl)n- or -(CH2)r;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halo C1-C8 alkoxy, halo C1-C8 alkylthio, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkoxy C1-C8 alkyl, halo C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, aryl, heterocyclyl, aryl C1-C8 alkyl or heterocyclyl C1-C8 alkyl, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “aryl”, “heterocyclyl”, “aryl C1-C8 alkyl” and “heterocyclyl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl,
190
C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SOajRn, -N (R 13)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring; and Xi, X2 are not hydrogen at the same time;
Ri, R2 each independently represent H, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino, amino C1-C8 alkyl, amino carbonyl, amino carbonyl C1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl
C1-C8 alkyl, R4R5N-(CO)-NR3-, Rs , R3-S(O)m-(Cl-C8 alkyl)n-, R3-O-(C1-C8 alkyl)n-, R3-(CO)-(C1-C8 alkyl)n-, R3-O-(C1-C8 alkyl)n-(CO)-, R3-(CO)-O-(C1-C8 alkyl)n-, R3-S-(CO)-(C1-C8 alkyl)n-, R3-O-(CO)-(C1-C8 alkyl)- or R3-O-(CO)-O-(C1-C8 alkyl)-, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “amino”, “amino C1-C8 alkyl”, “amino carbonyl”, “amino carbonyl C1-C8 alkyl” and “aminosulfonyl” are each independently unsubstituted or substituted by one or two groups selected from -Rn, -ORn, -(CO)Rn, -(CO)ORn, -(C1-C8 alkyl)-(CO)ORn, -(SO2)Rn, -(SO2)ORn, -(C1-C8 alkyl)-(SO2)Rn, -(CO)N(Ri2)2 and -(SO2)N(Ri2)2, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-G8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N (R 13) 2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
R6 represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl or cyano, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or
191 substituted by at least one group selected from halogen, C1-C8 alkoxy and C1-C8 alkoxy carbonyl;
R-7, R7’, R8, R8’ each independently represent H, C1-C8 alkyl, halogen, halo C1-C8 alkyl, amino, hydroxy C1-C8 alkyl or C1-C8 alkoxy;
R3, R4, R5 each independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Ru independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, benzyl, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “phenyl” and “benzyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;
Ri2 independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or N(Rj2)2 in -(CO)N(Ri2)2 or -(SO2)N(Ri2)2 independently represents heterocyclyl 'X , \—/, Or with nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;
R13 independently represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8
192 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;
r represents 2, 3, 4, 5 or 6;
or, when the general formula is I, X3, X4 each independently represent O, S, NH or
N-(C1-C8)alkyl;
X5 represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8
Xv 1^X17 cycloalkenyl, heterocyclyl, aryl, * xn, 1 xn, 7. xn, δ o ,
J--S- ,X12 xi [1
160 Xœ X11,
X14
X14 ο
Αν'Χι3 ΑγΧ’3
ΟΙ 1 I
Χΐ4 , Χΐ4 ΟΓ Χΐ3^Ν'Χΐ4
A,0Xn ο , wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkenyl,
O vCkv vs'v A heterocyclyl, aryl, * Λιι, ί Y Λιι,
Cl· .O X11, /n'Xi3
Xl4 .
o
X13 X13 /Ό'ΝγΧ13
Xi4 , X14 and X14 , the “C3-C8 cycloalkyl”, “C3-C8 cycloalkenyl”, “heterocyclyl” and “aryl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fiised ring;
yN χ 13 Nor N(X5)2 represents X14 or heterocyclyl or 0 with nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;
X11 independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl or θ M wherein, the “C3-C8 cycloalkyl”, “C3-C8
193 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -ORb, -SRb, -(CO)ORi3, -(SÜ2)Ri3» -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X12 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” and “aryl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X13, X|4 each independently represent H, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or C, X13, X14, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl, or N, X13, X14, taken together, form heterocyclyl with nitrogen atom at 1-position, wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” and “C2-C8 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “aryl”, “aryl C1-C8 alkyl”, “heterocyclyl” and “heterocyclyl C1-C8 alkyl” are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8
194 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -ORi3, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C8 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring, the “5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl” is unsubstituted or substituted by 1-4 groups selected from C1-C8 alkyl, C1-C8 alkoxy carbonyl and benzyl, or together with aryl or heterocyclyl forms a fused ring, the “heterocyclyl with nitrogen atom at l-position”is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl.
4. The carboxylic acid derivative-substituted iminoaryl compound according to claim 2 or 3, which is characterized in that,
Y represents halogen, halo C1-C6 alkyl or cyano;
X represents -CXiX2-(C1-C6 alkyl)n-, -(C1-C6 alkyl)-CXiX2-(Cl-C6 alkyl)n- or -(CH2)r-;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C6 alkyl, halo C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, aryl, heterocyclyl, aryl C1-C6 alkyl or heterocyclyl C1-C6 alkyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “aryl”, “heterocyclyl”, “aryl C1-C6 alkyl” and “heterocyclyl C1-C6 alkyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(RI3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring; and Xi, X2 are not hydrogen at the same time;
Ri, R2 each independently represent H, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino, amino C1-C6 alkyl, amino carbonyl, amino carbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl
195
C1-C6 alkyl, R4R5N-(CO)-NR3-, *5 , R3-S(O)m-(Cl-C6 alkyl)n-, R3-O-(C1-C6 alkyl)n-,
R3-(CO)-(C1-C6 alkyl)n-, R3-O-(C1-C6 alkyl)n-(CO)-, R3-(CO)-O-(C1-C6 alkyl)n-, R3-S-(CO)-(C1-C6 alkyl)n-, R3-O-(CO)-(C1-C6 alkyl)- or R3-O-(CO)-O-(C1-C6 alkyl)-, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “amino”, “amino C1-C6 alkyl”, “amino carbonyl”, “amino carbonyl C1-C6 alkyl” and “aminosulfonyl” are each independently unsubstituted or substituted by one or two groups selected from -Rn, -ORn, -(CO)Rn, -(CO)ORn, -(C1-C6 alkyl)-(CO)ORn, -(SO2)Rn, -(SO2)ORn, -(C1-C6 alkyl)-(SO2)Rn, -(CO)N(Ri2)2 and -(SO2)N(Ri2)2, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -ORj3, -SRi3, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
R6 represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyano, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from halogen, C1-C6 alkoxy and C1-C6 alkoxy carbonyl;
R7, R7’, Rg, Rg’ each independently represent H, C1-C6 alkyl, halogen, halo C1-C6 alkyl, amino, hydroxy C1-C6 alkyl or C1-C6 alkoxy;
R3, R4, R5 each independently represent H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”,
196 “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SC>2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Ru independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, benzyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “phenyl” and “benzyl”are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy;
R12 independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or N/Rph in -(CO)N(Ri2)2 or -(SÜ2)N(Ri2)2 independently /'N'Y vNV ? N ) LÀ represents heterocyclyl X , '—/, or with nitrogen atom at 1-position that is unsubstituted or substituted by 1,2 or 3 groups selected from oxo and C1-C6 alkyl;
R13 independently represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl or phenyl substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy;
or, when the general formula is I, X3, X4 each independently represent O, S, NH or
N-(C1-C6)alkyl;
X5 represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6
O \Λο'Χΐ1 ?
o O X13N-X14
7nx” Zn-X” ’Y n-*” ïY» Άχ i i 4 O i I χΐ4 , χΐ4 , χΐ4 , χΐ4 or o , wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by at
197 least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl,
Ο Ο Ο η n ,χ13 u ! 1 t V°'x Vsx ΧΛχ '/cAx v\rXl1 Y Xl1 X heterocyclyl, aryl, * X11, < xn, a Xh, O X-n, \ o 5 q , x-u , o
\N<YXl3 A'Xl3 AyN<^Xl3
X14 , X14 and Xu , the “C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl” and “aryl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Rb)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
>-N^Xi3 /'nA /'N'Y i I A e N X il L n · or N(X5)2 represents X14 or heterocyclyl a , '—/, or with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;
X11 independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl Cl-C6 alkyl or Q M /N'Xâ A wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X12 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl,
198 aryl or aryl C1-C6 alkyl, wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” and “aryl C1-C6 alkyl” are each independently unsubstituted or substituted by 1,2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X13, Xj4 each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, or C, X13, X14, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or
I \ nitrogen-containing heterocyclyl, or N, X13, X14, taken together, form heterocyclyl A , /'NA \__/, A or with nitrogen atom at 1 -position, wherein, the “Cl-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “aryl”, “aryl C1-C6 alkyl”, “heterocyclyl” and “heterocyclyl C1-C6 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Rb, -N(Ri3)2 and -O-(C1-C6 alkyl)-(CO)OR]3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring, the “5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl” is unsubstituted or substituted by 1,2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy carbonyl and benzyl, or /K /x /'NA vn A N 7 LJ together with aryl or heterocyclyl forms a fused ring, the “A , \—f, and /'nK
K-°” are unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl.
199
5. The carboxylic acid derivative-substituted iminoaryl compound according to any of claims 1 to 4, which is characterized in that,
X represents -CXiX2-(C1-C3 alkyl)n-, -(C1-C3 alkyl)-CXiX2-(Cl-C3 alkyl)n- or -(CH2)r-;
Xi, X2 each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C3 alkyl, hydroxy C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C3 alkyl, halo C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylamino C1-C3 alkyl, aryl, heterocyclyl, aryl C1-C3 alkyl or heterocyclyl C1-C3 alkyl, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “aryl”, “heterocyclyl”, “aryl C1-C3 alkyl” and “heterocyclyl C1-C3 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring; and Xi, X2 are not hydrogen at the same time;
or, when the general formula is I, X5 represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6
O sxCk «,A alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, τ X11, * xn, t- X11, o 0 9
J s A ,X12 .. ? S x ^'N'*3 'Y%'X13 d'N'X13 -VNYX13 o Xl2, O 0 , X11, VxrXl1 5 x14 } X14 , Xi4 , Xi4 or X13-N-X14
A^OXn o , wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano,
O nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, * xn, V xn, Y- xn, o
fl A x K°Y°A. V” A'*3 ΑΝγ*·=
Zcr^Xn, VO' 11, ο , X14 , X14 , X14 and Xi4 ,the“C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl” and “aryl” are each independently
200 unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -ORb, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(R13)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2Oform a fused ring;
vN^x13 N=\ /'nA ^A i I e N > il L n · or N(X5)2 represents X14 or heterocyclyl X , \—/, xz or with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;
Xn independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 ? ΊΓΤ i alkyl, aryl, aryl C1-C3 alkyl or I , wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “heterocyclyl”, “heterocyclyl C1-C3 alkyl”, “aryl” and “aryl C1-C3 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
Xi2 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “heterocyclyl”, “heterocyclyl C1-C3 alkyl”, “aryl” and “aryl C1-C3 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo
201
C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -ORb, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- form a fused ring;
X13, X14 each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy
Cl-C3 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or C, X13, X14, taken together, form 5~8 membered saturated carbocyclyl, or
with nitrogen atom at 1-position, wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” and “C2-C6 alkynyl” are each independently unsubstituted or substituted by halogen, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “aryl”, “aryl C1-C3 alkyl”, “heterocyclyl” and “heterocyclyl C1-C3 alkyl” are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR13, -SR13, -(CO)ORi3, -(SO2)Ri3, -N(Ri3)2 and -O-(C1-C3 alkyl)-(CO)ORi3, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted
-OCH2CH2- or -OCH2O- form a fused ring, the “5~8 membered saturated carbocyclyl, or NH” is unsubstituted or substituted by 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6
N=\ I ' alkoxy carbonyl and benzyl, or together with phenyl or thienyl forms a fused ring, the “ \__Z, and are unsubstituted or substituted by 1,2 or 3 groups selected from oxo and C1-C6 alkyl;
optionally, Q represents
202
6. The carboxylic acid derivative-substituted iminoaryl compound according to any of daims 1 to 5, which is characterized in that, when the carbon atom connected to Xi and X2 in the
5 general formula is a chiral center, it is in R configuration, and based on the content of stereoisomers having R and S configurations at this position, it has a stereochemical purity of
60-100% (R).
7. The carboxylic acid derivative-substituted iminoaryl compound according to claim 1, which is characterized in that, it is any one selected from:
8. A method for preparing the carboxylic acid derivative-substituted iminoaryl compound according to any of daims 1 to 7, which comprises the following steps:
15 subjecting a compound represented by general formula II and a compound represented by general formula ΙΙΓ to an élimination reaction to obtain a compound represented by general formula F, with the Chemical reaction équation shown as follows:
203
□ □ ' □ ' or, subjecting a compound represented by general formula II and a compound represented by general formula III to an élimination reaction to obtain a compound represented by general formula I, with the Chemical reaction équation shown as follows:
JO J+ x^j/v-----Jl JL^N X W 'X3H Hal Π Q'X χ4X
5 □ □□ wherein, Hal represents halogen, other substituents Q, M, W, Y, Z, X, X3 and X4 are as defined in any of daims 1 to 7;
the reaction is carried out in the presence of a base and a solvent; optionallly, the base is at least one selected from inorganic bases and organic bases, and/or the solvent is at least one
10 selected from DMF, methanol, éthanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane and ethyl acetate.
9. A herbicidal composition, which is characterized in that, the composition comprises (i) at least one of the carboxylic acid derivative-substituted iminoaryl compounds according to any of daims 1 to 7 in a herbicidally effective amount; or, the composition further comprises (ii) one or
15 more other herbicides in a herbicidally effective amount and/or safeners and/or (iii) a formulation auxiliary accepted in agricultural chemistry; optionallly, the other herbicide is one or more selected from the following compounds and acids, salts and esters thereof:
(1) HPPD inhibitor selected from: topramezone, isoxaflutole, tembotrione, tefuryltrione, shuangzuocaotong, huanbifucaotong, sanzuohuangcaotong, benzuofucaotong and
(2) PDS inhibitor selected from: flurtamone, diflufenican and picolinafen;
(3) DOXP inhibitor selected from : clomazone and bixlozone;
(4) ALS inhibitor selected from: tribenuron-methyl, thifensulfuron methyl, pyrazosulfuron-ethyl, thiencarbazone-methyl, halosulfuron methyl, rimsulfuron, 25 nicosulfuron and imazamox;
• *
(5) ACCase inhibitor selected from: clethodim, sethoxydim and quizalofop-P-methyl;
(6) PPO inhibitor selected from : oxyfluorfen, oxadiazon, oxadiargyl, sulfentrazone,
204 pyraclonil, flumioxazin, saflufenacil, carfentrazone-ethyl and trifludimoxazin;
(7) PSII inhibitor selected from: metribuzin, terbuthylazine, amicarbazone, chlorotoluron, isoproturon, bromacil, propanil, desmedipham, phenmedipham, bentazone and bromoxynil;
(8) inhibitor of microtubule assembly selected from : butral in and pendimethalin;
(9) VLCFA inhibitor selected from: butachlor, pretilachlor, mefenacet, s-metolachlor, flufenacet, pyroxasulfone and anilofos;
(10) lipid synthesis inhibitor (non-acetyl-CoA carboxylase) : prosulfocarb ;
nh2
JL A
ΕΝΟψ r-\
(11) Synthetic hormones selected from: Α/'ό , fluroxypyr, florpyrauxifen benzyl, halauxifen-methyl, triclopyr, clopyralid, picloram, aminopyralid, dicamba, 2-methyl-4-chlorophenoxyacetic acid and 2, 4-dichlorophenoxy acetic acid;
(12) EPSPS inhibitor: glyphosate;
(13) GS inhibitor selected from: glufosinate ammonium and glufosinate-P-ammonium;
(14) PSI inhibitor selected from: paraquat dichloride and diquat dibromide monohydrate;
(15) Cellulose synthesis inhibitorselectedfrom: triaziflam and indaziflam;
(16) other herbicides: cinmethylin.
10. The herbicidal composition according to claim 9, which is characterized in that, in item
FsC-f H /-Cl nA M / o An b (i), the composition comprises compound \ .
11. A method for controlling an undesirable plant, characterized in that it comprises applying at least one of the carboxylic acid derivative-substituted iminoaryl compounds according to any of daims 1 to 7 or the herbicidal composition according to claim 9 or 10 in a herbicidally effective amount on a plant or in its area or to soil or water to control the emergence or growth of undesirable plant.
12. Use of at least one of the carboxylic acid derivative-substituted iminoaryl compounds according to any of daims 1 to 7 or the herbicidal composition according to claim 9 or 10 for controlling a undesirable plant.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010028477.6 | 2020-01-11 | ||
CN202010077193.6 | 2020-01-24 | ||
CN202010117877.4 | 2020-02-25 | ||
CN202010281666.4 | 2020-04-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
OA21190A true OA21190A (en) | 2024-02-29 |
Family
ID=
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP4089078A1 (en) | Carboxylic acid derivative-substituted imino aryl compound, preparation method therefor, herbicidal composition and use thereof | |
AU2016350960B2 (en) | Pyrazolone compound or salt thereof, preparation method therefor, herbicide composition and use thereof | |
US4659363A (en) | N-(2-nitrophenyl)-2-aminopyrimidine derivatives, the preparation and use thereof | |
CN107074781B (en) | Pyrimidinone compounds | |
KR20220128639A (en) | Conjugated-ring substituted aromatic compounds, methods for their preparation, herbicidal compositions and uses thereof | |
MX2010014027A (en) | Substituted 1-(diazinyl) pyrazole-4-yl-acetic acids, method for the production thereof, and use thereof as herbicides and plant growth regulators. | |
HUT72912A (en) | Pyridazinones and their use as fungicides and compositions containing them | |
US11472792B2 (en) | Herbicidal mixtures | |
WO1996033994A1 (en) | Amino-substituted derivatives, process for the preparation thereof, and herbicide | |
AU2019386018A1 (en) | N-(1, 3, 4-oxadiazole-2-yl)aryl formamides or salt thereof, preparation method therefor, herbicidal composition and use thereof | |
AU2020378483A1 (en) | Substituted-isoxazoline-containing aromatic compound, preparation method therefor, herbicidal composition and use thereof | |
CN102336744B (en) | Substituted triazoline ether ketone class compound and application thereof as bactericide as well as insecticide and acaricide | |
AU2018430945A1 (en) | Substituted pyrimidinyl formyl oxime derivative, preparation method therefor, herbicidal composition and use thereof | |
OA21190A (en) | Carboxylic acid derivative-substituted imino aryl compound, preparation method therefor, herbicidal composition and use thereof. | |
JPH0625177A (en) | Pyrazole derivative and herbicide | |
JPH06345740A (en) | Substituted azine | |
US20230072860A1 (en) | Isoxazoline oxime formate compound, preparation method therefor, herbicidal composition and use thereof | |
LU84914A1 (en) | ALCOYLAMINO N-PHENYL PYRAZOLE AND N-PHENYL PYRAZOLE LACTAMES HERBICIDES | |
AU613222B2 (en) | 5-substituted-2,4-diphenylpyrimidine derivatives, their production and use | |
AU2017388277A1 (en) | Agricultural chemicals | |
CA1274242A (en) | Substituted furazanes | |
US10172350B2 (en) | Substituted 5-hydroxy-2-phenyl-3-heteroaryl pentanenitrile derivatives, method for the production thereof and use thereof as herbicides and/or plant growth regulators | |
US20220073466A1 (en) | Pyridyloxy-carboxylate derivative and preparation method therefor, herbicidal composition, and use | |
CN112442026A (en) | Mesoionic derivative and preparation method and application thereof | |
JPS6160666A (en) | Substituted arylsulfonylguanidine and acid addition |