JP2001516758A5 - - Google Patents
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- JP2001516758A5 JP2001516758A5 JP2000511765A JP2000511765A JP2001516758A5 JP 2001516758 A5 JP2001516758 A5 JP 2001516758A5 JP 2000511765 A JP2000511765 A JP 2000511765A JP 2000511765 A JP2000511765 A JP 2000511765A JP 2001516758 A5 JP2001516758 A5 JP 2001516758A5
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- Japan
- Prior art keywords
- group
- alkyl
- groups
- alkoxy
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- Prior art date
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- -1 Phenyl Chemical group 0.000 description 406
- 125000004093 cyano group Chemical group *C#N 0.000 description 266
- 125000005843 halogen group Chemical group 0.000 description 240
- 229910052736 halogen Inorganic materials 0.000 description 220
- 150000002367 halogens Chemical class 0.000 description 220
- 125000004438 haloalkoxy group Chemical group 0.000 description 209
- 229910052739 hydrogen Inorganic materials 0.000 description 208
- 239000001257 hydrogen Substances 0.000 description 208
- 150000002431 hydrogen Chemical class 0.000 description 178
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 173
- 125000003545 alkoxy group Chemical group 0.000 description 170
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 141
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 78
- 125000002950 monocyclic group Chemical group 0.000 description 78
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 74
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 60
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 52
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 49
- 229910052760 oxygen Inorganic materials 0.000 description 48
- 229910052717 sulfur Inorganic materials 0.000 description 48
- 150000001875 compounds Chemical class 0.000 description 45
- 125000003844 furanonyl group Chemical group 0.000 description 45
- 229910052757 nitrogen Inorganic materials 0.000 description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 35
- 125000004433 nitrogen atom Chemical group N* 0.000 description 32
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 30
- 229910052783 alkali metal Inorganic materials 0.000 description 28
- 150000001340 alkali metals Chemical class 0.000 description 28
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 28
- 150000001342 alkaline earth metals Chemical class 0.000 description 28
- 125000004076 pyridyl group Chemical group 0.000 description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 27
- 125000001544 thienyl group Chemical group 0.000 description 27
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 26
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 26
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 26
- 239000010941 cobalt Substances 0.000 description 26
- 229910017052 cobalt Inorganic materials 0.000 description 26
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 26
- 239000010949 copper Substances 0.000 description 26
- 229910052802 copper Inorganic materials 0.000 description 26
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 26
- 229910052759 nickel Inorganic materials 0.000 description 26
- 229910052709 silver Inorganic materials 0.000 description 26
- 239000004332 silver Substances 0.000 description 26
- 229910052725 zinc Inorganic materials 0.000 description 26
- 239000011701 zinc Substances 0.000 description 26
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 24
- 125000004043 oxo group Chemical group O=* 0.000 description 24
- 125000000464 thioxo group Chemical group S=* 0.000 description 24
- 125000001841 imino group Chemical group [H]N=* 0.000 description 23
- 150000002148 esters Chemical class 0.000 description 22
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 21
- DQPULKJUSYSTBM-UHFFFAOYSA-N 3-[3-(hydroxymethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2CO)C2=C1 DQPULKJUSYSTBM-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 125000004429 atom Chemical group 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 16
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 15
- 125000002541 furyl group Chemical group 0.000 description 15
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 15
- 229940022663 acetate Drugs 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 14
- 125000005646 oximino group Chemical group 0.000 description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 10
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 10
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 8
- KUVVDQSHRGBNOB-UHFFFAOYSA-N n-ethylsulfonyl-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)CC)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O KUVVDQSHRGBNOB-UHFFFAOYSA-N 0.000 description 8
- 229930192474 thiophene Chemical group 0.000 description 8
- RHTUQTQNJSARMD-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-methylsulfonyl-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(=O)NS(C)(=O)=O)C2=C1 RHTUQTQNJSARMD-UHFFFAOYSA-N 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 7
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 6
- KCYUZABVXQYVDE-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-propan-2-ylsulfonyl-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)C(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O KCYUZABVXQYVDE-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
- OCLHYIFKHVZMKE-UHFFFAOYSA-N n-(3-cyanophenyl)-2-[2-methyl-4-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetamide Chemical compound CC1=CC(C=2C3=CC(=CC=C3SN=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=CC=C1OCC(=O)NC1=CC=CC(C#N)=C1 OCLHYIFKHVZMKE-UHFFFAOYSA-N 0.000 description 6
- MWLNFERZNNTDAB-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-(propan-2-ylsulfamoyl)-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)NC(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O MWLNFERZNNTDAB-UHFFFAOYSA-N 0.000 description 5
- 125000005336 allyloxy group Chemical group 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 5
- 229940011051 isopropyl acetate Drugs 0.000 description 5
- VXRWWXRYBXFAQT-UHFFFAOYSA-N n-(dimethylsulfamoyl)-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)N(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O VXRWWXRYBXFAQT-UHFFFAOYSA-N 0.000 description 5
- RDEZGFOPFILMHL-UHFFFAOYSA-N n-[di(propan-2-yl)sulfamoyl]-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)N(C(C)C)C(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O RDEZGFOPFILMHL-UHFFFAOYSA-N 0.000 description 5
- WHHPDEBDOABGOO-UHFFFAOYSA-N n-benzylsulfonyl-6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C(C(=C1)F)=CC2=C1SN=C2C(=O)NS(=O)(=O)CC1=CC=CC=C1 WHHPDEBDOABGOO-UHFFFAOYSA-N 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- ZVHVSBUADWJVNH-UHFFFAOYSA-N methyl 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O ZVHVSBUADWJVNH-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 description 3
- TXFHGHFAGMKHQJ-UHFFFAOYSA-N 1-methyl-3-(3-methyl-1,2-benzothiazol-5-yl)-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C2C(C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O TXFHGHFAGMKHQJ-UHFFFAOYSA-N 0.000 description 3
- GYRNMIQMWDACOU-UHFFFAOYSA-N 1-methyl-3-[3-(3-methyl-4-prop-2-ynoxyphenyl)-1,2-benzothiazol-5-yl]-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C(OCC#C)C(C)=CC(C=2C3=CC(=CC=C3SN=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 GYRNMIQMWDACOU-UHFFFAOYSA-N 0.000 description 3
- GMALEPXBWHKPGD-UHFFFAOYSA-N 1-methyl-3-[3-(methylsulfonylmethyl)-1,2-benzothiazol-5-yl]-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2CS(C)(=O)=O)C2=C1 GMALEPXBWHKPGD-UHFFFAOYSA-N 0.000 description 3
- IMBUBZIBJJGWMN-UHFFFAOYSA-N 2-[2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetic acid Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C=3C(=CC=CC=3)OCC(O)=O)C2=C1 IMBUBZIBJJGWMN-UHFFFAOYSA-N 0.000 description 3
- NQJNXZVTGPQFCR-UHFFFAOYSA-N 2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]-n-methylsulfonylacetamide Chemical compound CC1=CC=C(OCC(=O)NS(C)(=O)=O)C=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 NQJNXZVTGPQFCR-UHFFFAOYSA-N 0.000 description 3
- TURQCINHOUHXNR-UHFFFAOYSA-N 2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]acetonitrile Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2CC#N)C2=C1 TURQCINHOUHXNR-UHFFFAOYSA-N 0.000 description 3
- NGWZBSODCAMNSC-UHFFFAOYSA-N 2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]butanenitrile Chemical compound C1=C2C(C(C#N)CC)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O NGWZBSODCAMNSC-UHFFFAOYSA-N 0.000 description 3
- PXYRXFVXICIDHZ-UHFFFAOYSA-N 3-(3-acetyl-1,2-benzothiazol-5-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C2C(C(=O)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O PXYRXFVXICIDHZ-UHFFFAOYSA-N 0.000 description 3
- GOTUUOPBTVKVDJ-UHFFFAOYSA-N 3-(6-fluoro-3-methyl-1,2-benzoxazol-5-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C2C(C)=NOC2=CC(F)=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O GOTUUOPBTVKVDJ-UHFFFAOYSA-N 0.000 description 3
- SILJXCPCJNNHNV-UHFFFAOYSA-N 3-[3-(dibromomethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(Br)Br)C2=C1 SILJXCPCJNNHNV-UHFFFAOYSA-N 0.000 description 3
- QIUOYHTVEPQZGW-UHFFFAOYSA-N 6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxylic acid Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C(C(=C1)F)=CC2=C1SN=C2C(O)=O QIUOYHTVEPQZGW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PSIRNESXBUMTDV-UHFFFAOYSA-N CC1=C(C=CC(=C1)C2=NSC3=C2C=C(C=C3)N4C(=O)C=C(N(C4=O)C)C(F)(F)F)OCC(=O)N5C=NC6=CC=CC=C65 Chemical compound CC1=C(C=CC(=C1)C2=NSC3=C2C=C(C=C3)N4C(=O)C=C(N(C4=O)C)C(F)(F)F)OCC(=O)N5C=NC6=CC=CC=C65 PSIRNESXBUMTDV-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 229940007550 benzyl acetate Drugs 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 3
- ARIOPGOVCUCLEU-UHFFFAOYSA-N n-[(3-chlorophenyl)methylsulfonyl]-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(=O)NS(=O)(=O)CC=3C=C(Cl)C=CC=3)C2=C1 ARIOPGOVCUCLEU-UHFFFAOYSA-N 0.000 description 3
- JAIYHPUVNLVDNJ-UHFFFAOYSA-N n-benzylsulfonyl-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(=O)NS(=O)(=O)CC=3C=CC=CC=3)C2=C1 JAIYHPUVNLVDNJ-UHFFFAOYSA-N 0.000 description 3
- OKWBLVIQIQGPNR-UHFFFAOYSA-N n-methoxy-2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetamide Chemical compound CONC(=O)COC1=CC=C(C)C(C=2C3=CC(=CC=C3SN=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OKWBLVIQIQGPNR-UHFFFAOYSA-N 0.000 description 3
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 3
- IABBFAWTTAULCO-UHFFFAOYSA-N 2-[2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 IABBFAWTTAULCO-UHFFFAOYSA-N 0.000 description 2
- OUPNXYMAOYOYCC-UHFFFAOYSA-N 2-[6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]acetonitrile Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C(C(=C1)F)=CC2=C1SN=C2CC#N OUPNXYMAOYOYCC-UHFFFAOYSA-N 0.000 description 2
- XUTXPSXTMHCTOY-UHFFFAOYSA-N 3-(6-fluoro-3-methyl-1,2-benzothiazol-5-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C2C(C)=NSC2=CC(F)=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O XUTXPSXTMHCTOY-UHFFFAOYSA-N 0.000 description 2
- JDMOZBSDGCVUAK-UHFFFAOYSA-N 3-[3-(1-hydroxyethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C2C(C(O)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O JDMOZBSDGCVUAK-UHFFFAOYSA-N 0.000 description 2
- PCGDIWWKQNSBHE-UHFFFAOYSA-N 3-[3-(1-methoxyethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C2C(C(C)OC)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O PCGDIWWKQNSBHE-UHFFFAOYSA-N 0.000 description 2
- XDUZZPZPRQWNGH-UHFFFAOYSA-N 3-[3-(2-methoxyphenyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 XDUZZPZPRQWNGH-UHFFFAOYSA-N 0.000 description 2
- AFKZDVNEXFUQCJ-UHFFFAOYSA-N 3-[6-fluoro-3-(methoxymethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C2C(COC)=NSC2=CC(F)=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O AFKZDVNEXFUQCJ-UHFFFAOYSA-N 0.000 description 2
- HBIHCBPICTXVKP-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carbaldehyde Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C=O)C2=C1 HBIHCBPICTXVKP-UHFFFAOYSA-N 0.000 description 2
- NZHSMVSTWJMYLE-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-[(4-methylphenyl)methylsulfonyl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=CC(C)=CC=C1CS(=O)(=O)NC(=O)C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 NZHSMVSTWJMYLE-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- LAULFZIZDHINAX-UHFFFAOYSA-N furan-2-carboxylic acid Chemical compound OC(=O)C1=CC=CO1.OC(=O)C1=CC=CO1 LAULFZIZDHINAX-UHFFFAOYSA-N 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- DMRKBTQZKOXGNF-UHFFFAOYSA-N n-benzylsulfonyl-n-(ethoxymethyl)-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)N(COCC)C(=O)C(C1=C2)=NSC1=CC=C2N1C(=O)C=C(C(F)(F)F)N(C)C1=O DMRKBTQZKOXGNF-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 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
- HZCDWHDRHCFBLV-UHFFFAOYSA-N 3-[3-(4-ethylphenyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=CC(CC)=CC=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 HZCDWHDRHCFBLV-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Chemical group 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93145197A | 1997-09-17 | 1997-09-17 | |
| US08/931,451 | 1997-09-17 | ||
| US12883198A | 1998-08-04 | 1998-08-04 | |
| US09/128,831 | 1998-08-04 | ||
| PCT/US1998/019251 WO1999014216A1 (en) | 1997-09-17 | 1998-09-15 | Substituted 3(-1,2-benzisothiazol or isoxazol-5 yl)-substituted pyrimidine as herbicides |
Publications (2)
| Publication Number | Publication Date |
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| JP2001516758A JP2001516758A (ja) | 2001-10-02 |
| JP2001516758A5 true JP2001516758A5 (https=) | 2006-01-05 |
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| JP2000511765A Pending JP2001516758A (ja) | 1997-09-17 | 1998-09-15 | 除草剤としての置換３（−１，２−ベンズイソチアゾールまたはイソオキサゾール−５イル）−置換ピリミジン |
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| EP (1) | EP0908457B1 (https=) |
| JP (1) | JP2001516758A (https=) |
| KR (1) | KR20010030612A (https=) |
| CN (1) | CN1273585A (https=) |
| AR (3) | AR015168A1 (https=) |
| AT (1) | ATE227721T1 (https=) |
| AU (2) | AU737864B2 (https=) |
| BG (1) | BG104336A (https=) |
| BR (1) | BR9813017A (https=) |
| CA (1) | CA2246221A1 (https=) |
| CZ (1) | CZ2000861A3 (https=) |
| DE (1) | DE69809370T2 (https=) |
| ES (1) | ES2185118T3 (https=) |
| HU (1) | HUP0004477A3 (https=) |
| IL (1) | IL125947A0 (https=) |
| MX (1) | MXPA00002661A (https=) |
| NZ (1) | NZ331825A (https=) |
| PL (1) | PL339350A1 (https=) |
| SK (1) | SK3552000A3 (https=) |
| TR (1) | TR200000679T2 (https=) |
| TW (1) | TW474927B (https=) |
| WO (1) | WO1999014216A1 (https=) |
| YU (1) | YU15800A (https=) |
| ZA (1) | ZA988435B (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6140270A (en) * | 1998-09-14 | 2000-10-31 | American Cyanamid Company | Process for the preparation of 6-(perfluoroalkyl) uracil compounds from 2-(N,N-disubstituted) amino-4-(perfluoroalkyl)-1,3-oxazin-6-one compounds |
| JP4619542B2 (ja) * | 1999-02-16 | 2011-01-26 | ワイス・ホールディングズ・コーポレイション | １，３−オキサジン−６−オン類およびウラシル類の製造のための方法および中間体 |
| AU2001263864A1 (en) * | 2000-04-17 | 2001-10-30 | Basf Aktiengesellschaft | Herbicidal 3-heterocyclic substituted benzisothiazole and benzisoxazole compounds |
| CA2421839A1 (en) * | 2000-09-08 | 2003-03-07 | Basf Aktiengesellschaft | Method for producing anellated tetrahydro-[1h]-triazoles |
| DE60232170D1 (de) | 2001-08-30 | 2009-06-10 | Alizyme Therapeutics Ltd | Thieno-(1,3)-oxazin-4-one mit lipase inhibierender wirkung |
| WO2003087072A1 (en) * | 2002-03-29 | 2003-10-23 | Mochida Pharmaceutical Co., Ltd. | Therapeutic agent for endothelial disorder |
| CA2504410C (en) | 2002-10-30 | 2012-03-20 | Basf Aktiengesellschaft | Bifunctional phenyliso(thio)cyanates; method and intermediate products for the production thereof |
| PL2710005T3 (pl) | 2011-05-17 | 2017-07-31 | Principia Biopharma Inc. | Inhibitory kinazy tyrozynowej |
| WO2012158795A1 (en) | 2011-05-17 | 2012-11-22 | Principia Biopharma Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| ES2770550T3 (es) | 2011-05-17 | 2020-07-02 | Univ California | Inhibidores de quinasa |
| SI2892900T1 (en) | 2012-09-10 | 2018-01-31 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| DE102013226249A1 (de) * | 2013-12-17 | 2015-06-18 | Wacker Chemie Ag | Polyetherreste aufweisende Organopolysiloxangele |
| CN112353806A (zh) | 2014-02-21 | 2021-02-12 | 普林斯匹亚生物制药公司 | Btk抑制剂的盐和固体形式 |
| SG11201704808VA (en) | 2014-12-18 | 2017-07-28 | Principia Biopharma Inc | Treatment of pemphigus |
| WO2016210165A1 (en) | 2015-06-24 | 2016-12-29 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| CN115054586B (zh) | 2016-06-29 | 2024-08-02 | 普林斯匹亚生物制药公司 | 改性的释放制剂 |
| EP3648605A1 (en) * | 2017-07-03 | 2020-05-13 | Bayer CropScience Aktiengesellschaft | Novel isothiazolo-based bicycles, processes for their preparation and their use as herbicides and/or plant growth regulators |
| CN109776302A (zh) * | 2017-11-13 | 2019-05-21 | 中国科学院化学研究所 | 一种由木质素为甲基源制备重要化学品的方法 |
| US20210106584A1 (en) | 2019-10-14 | 2021-04-15 | Principia Biopharma Inc. | Methods for treating immune thrombocytopenia by administering (r)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| US11814390B2 (en) | 2020-01-22 | 2023-11-14 | Principia Biopharma Inc. | Crystalline forms of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)-1H-pyrazolo[3,4-D]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| CN114276287B (zh) * | 2021-12-27 | 2023-10-03 | 浙江工业大学 | N-(取代苄氧基)酰胺类化合物及其制备方法和应用 |
| CN116354953B (zh) * | 2022-12-31 | 2024-07-16 | 西北农林科技大学 | 含苯并噻唑类化合物的除草组合物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| IL97102A0 (en) * | 1990-02-16 | 1992-03-29 | Ici Plc | Heterocyclic compounds |
| US5484763A (en) * | 1995-02-10 | 1996-01-16 | American Cyanamid Company | Substituted benzisoxazole and benzisothiazole herbicidal agents |
| US5753595A (en) * | 1995-08-31 | 1998-05-19 | Fmc Corporation | Herbicidal 3-(substituted benzoxazol-7-yl) and 3-(Substituted benzothiazol-7-yl)-1-substituted-6-trifluoromethyl-2 4-(1h 3h)pyrimidinediones |
| AU7253496A (en) * | 1995-10-04 | 1997-04-28 | Fmc Corporation | Herbicidal heterocyclic benzisoxazoles and benzisoxazolidinones |
-
1998
- 1998-08-27 IL IL12594798A patent/IL125947A0/xx unknown
- 1998-09-02 CA CA002246221A patent/CA2246221A1/en not_active Abandoned
- 1998-09-09 NZ NZ331825A patent/NZ331825A/xx unknown
- 1998-09-15 BR BR9813017-0A patent/BR9813017A/pt not_active IP Right Cessation
- 1998-09-15 PL PL98339350A patent/PL339350A1/xx unknown
- 1998-09-15 JP JP2000511765A patent/JP2001516758A/ja active Pending
- 1998-09-15 HU HU0004477A patent/HUP0004477A3/hu unknown
- 1998-09-15 CZ CZ2000861A patent/CZ2000861A3/cs unknown
- 1998-09-15 AU AU84239/98A patent/AU737864B2/en not_active Ceased
- 1998-09-15 AU AU93925/98A patent/AU9392598A/en not_active Abandoned
- 1998-09-15 WO PCT/US1998/019251 patent/WO1999014216A1/en not_active Ceased
- 1998-09-15 SK SK355-2000A patent/SK3552000A3/sk unknown
- 1998-09-15 CN CN98809898A patent/CN1273585A/zh active Pending
- 1998-09-15 TR TR2000/00679T patent/TR200000679T2/xx unknown
- 1998-09-15 YU YU15800A patent/YU15800A/sh unknown
- 1998-09-15 ZA ZA9808435A patent/ZA988435B/xx unknown
- 1998-09-16 EP EP98307495A patent/EP0908457B1/en not_active Expired - Lifetime
- 1998-09-16 AT AT98307495T patent/ATE227721T1/de not_active IP Right Cessation
- 1998-09-16 TW TW087115446A patent/TW474927B/zh not_active IP Right Cessation
- 1998-09-16 AR ARP980104611A patent/AR015168A1/es unknown
- 1998-09-16 DE DE69809370T patent/DE69809370T2/de not_active Expired - Fee Related
- 1998-09-16 ES ES98307495T patent/ES2185118T3/es not_active Expired - Lifetime
-
1999
- 1999-11-04 AR ARP990105578A patent/AR021081A2/es unknown
- 1999-11-04 AR ARP990105577A patent/AR021500A2/es unknown
-
2000
- 2000-03-16 MX MXPA00002661 patent/MXPA00002661A/es unknown
- 2000-03-16 KR KR20007002805A patent/KR20010030612A/ko not_active Withdrawn
- 2000-04-13 BG BG104336A patent/BG104336A/xx unknown
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