CZ290330B6 - 2,6-Disubstituované pyridinové a 2,4-disubstituované pyrimidinové deriváty, způsob a meziprodukty pro jejich výrobu, jejich pouľití a herbicidní prostředky na jejich bázi a způsob potlačování růstu neľádoucích rostlin - Google Patents
2,6-Disubstituované pyridinové a 2,4-disubstituované pyrimidinové deriváty, způsob a meziprodukty pro jejich výrobu, jejich pouľití a herbicidní prostředky na jejich bázi a způsob potlačování růstu neľádoucích rostlin Download PDFInfo
- Publication number
- CZ290330B6 CZ290330B6 CZ1996175A CZ17596A CZ290330B6 CZ 290330 B6 CZ290330 B6 CZ 290330B6 CZ 1996175 A CZ1996175 A CZ 1996175A CZ 17596 A CZ17596 A CZ 17596A CZ 290330 B6 CZ290330 B6 CZ 290330B6
- Authority
- CZ
- Czechia
- Prior art keywords
- methyl
- pyrimidine
- yloxy
- trifluoromethylphenyl
- trifluoromethylpyrazol
- Prior art date
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- -1 2,6-Disubstituted pyridine Chemical class 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 20
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims abstract description 12
- 230000012010 growth Effects 0.000 title claims abstract description 7
- 239000000543 intermediate Substances 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 9
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000000033 alkoxyamino group Chemical group 0.000 claims abstract description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 47
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 39
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 9
- 150000003230 pyrimidines Chemical class 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
- KRBLZKALPKHYIC-UHFFFAOYSA-N 5-methyl-4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound CC1=CN=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1OC1=CC=CC(C(F)(F)F)=C1 KRBLZKALPKHYIC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- CWJFGKVASWBCPZ-UHFFFAOYSA-N 4-[4-methoxy-6-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazol-3-yl]oxypyrimidin-2-yl]benzonitrile Chemical compound COc1cc(Oc2cc(nn2C)C(F)(F)C(F)(F)F)nc(n1)-c1ccc(cc1)C#N CWJFGKVASWBCPZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- HXOGAPHLZJYSOJ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-4-methyl-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound Cc1cc(Oc2cc(nn2C)C(F)(F)F)nc(n1)-c1ccc(F)cc1F HXOGAPHLZJYSOJ-UHFFFAOYSA-N 0.000 claims description 2
- TWXGHYWKXQFGJG-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-4-methyl-6-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound N=1C(C=2C(=CC(F)=CC=2)F)=NC(C)=CC=1OC1=CC=CC(C(F)(F)F)=C1 TWXGHYWKXQFGJG-UHFFFAOYSA-N 0.000 claims description 2
- YSUUHPPBLYCHQP-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(methoxymethyl)-6-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound N=1C(C=2C=CC(Cl)=CC=2)=NC(COC)=CC=1OC1=CC=CC(C(F)(F)F)=C1 YSUUHPPBLYCHQP-UHFFFAOYSA-N 0.000 claims description 2
- SOBUEVWTQCGFLV-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methyl-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound Cc1cc(Oc2cc(nn2C)C(F)(F)F)nc(n1)-c1ccc(F)cc1 SOBUEVWTQCGFLV-UHFFFAOYSA-N 0.000 claims description 2
- OROSMKMJYBEVFM-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)oxy-2-(2,4-difluorophenyl)-5-methylpyrimidine Chemical compound CC1=CN=C(C=2C(=CC(F)=CC=2)F)N=C1OC1=CC=NC(Cl)=C1 OROSMKMJYBEVFM-UHFFFAOYSA-N 0.000 claims description 2
- DSAVNQIHUIJOSJ-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)oxy-5,6-dimethyl-2-[4-(trifluoromethoxy)phenyl]pyrimidine Chemical compound CC=1C(C)=NC(C=2C=CC(OC(F)(F)F)=CC=2)=NC=1OC1=CC=NC(Cl)=C1 DSAVNQIHUIJOSJ-UHFFFAOYSA-N 0.000 claims description 2
- JDDJPLHRFYGNIC-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)oxy-5-methyl-2-[4-(trifluoromethoxy)phenyl]pyrimidine Chemical compound CC1=CN=C(C=2C=CC(OC(F)(F)F)=CC=2)N=C1OC1=CC=NC(Cl)=C1 JDDJPLHRFYGNIC-UHFFFAOYSA-N 0.000 claims description 2
- RPONOTBYIOWOCQ-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)oxy-6-methyl-2-[4-(trifluoromethoxy)phenyl]pyrimidine Chemical compound N=1C(C=2C=CC(OC(F)(F)F)=CC=2)=NC(C)=CC=1OC1=CC=NC(Cl)=C1 RPONOTBYIOWOCQ-UHFFFAOYSA-N 0.000 claims description 2
- ODURFXFXRDEWNL-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)oxy-6-methyl-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound N=1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=CC=1OC1=CC=NC(Cl)=C1 ODURFXFXRDEWNL-UHFFFAOYSA-N 0.000 claims description 2
- PLJCPAJZBGUOCZ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 PLJCPAJZBGUOCZ-UHFFFAOYSA-N 0.000 claims description 2
- RWZWEEREJUPSJF-UHFFFAOYSA-N 4-[4-methyl-6-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazol-3-yl]oxypyrimidin-2-yl]benzonitrile Chemical compound Cc1cc(Oc2cc(nn2C)C(F)(F)C(F)(F)F)nc(n1)-c1ccc(cc1)C#N RWZWEEREJUPSJF-UHFFFAOYSA-N 0.000 claims description 2
- QMZYQVCGQKEEQS-UHFFFAOYSA-N 4-ethenyl-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound Cn1nc(cc1Oc1cc(C=C)nc(n1)-c1ccc(cc1)C(F)(F)F)C(F)(F)F QMZYQVCGQKEEQS-UHFFFAOYSA-N 0.000 claims description 2
- SDLCKLGYOKUNDV-UHFFFAOYSA-N 4-ethyl-6-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound N=1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(CC)=CC=1OC1=CC=CC(C(F)(F)F)=C1 SDLCKLGYOKUNDV-UHFFFAOYSA-N 0.000 claims description 2
- LKHVBRADJIVKEY-UHFFFAOYSA-N 4-methoxy-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound COc1cc(Oc2cc(nn2C)C(F)(F)F)nc(n1)-c1ccc(cc1)C(F)(F)F LKHVBRADJIVKEY-UHFFFAOYSA-N 0.000 claims description 2
- XJEMUQDQKSDFNP-UHFFFAOYSA-N 4-methyl-2-[4-(trifluoromethoxy)phenyl]-6-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound N=1C(C=2C=CC(OC(F)(F)F)=CC=2)=NC(C)=CC=1OC1=CC=CC(C(F)(F)F)=C1 XJEMUQDQKSDFNP-UHFFFAOYSA-N 0.000 claims description 2
- ZMZSYNRHUCYELN-UHFFFAOYSA-N 4-methyl-6-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazol-3-yl]oxy-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound Cc1cc(Oc2cc(nn2C)C(F)(F)C(F)(F)F)nc(n1)-c1ccc(cc1)C(F)(F)F ZMZSYNRHUCYELN-UHFFFAOYSA-N 0.000 claims description 2
- YOPRVERFOKDIHO-UHFFFAOYSA-N 4-methyl-6-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenoxy]pyrimidine Chemical compound CC1=CC(=NC(=N1)OC1=CC=C(C=C1)C(F)(F)F)OC1=CC(=CC=C1)C(F)(F)F YOPRVERFOKDIHO-UHFFFAOYSA-N 0.000 claims description 2
- BLYCEQPOONZTDJ-UHFFFAOYSA-N 5-methoxy-4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound COC1=CN=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1OC1=CC=CC(C(F)(F)F)=C1 BLYCEQPOONZTDJ-UHFFFAOYSA-N 0.000 claims description 2
- OQKAGNYSLSMLER-UHFFFAOYSA-N 5-methyl-2-(3-methylphenyl)-4-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound Cc1cccc(c1)-c1ncc(C)c(Oc2cc(nn2C)C(F)(F)F)n1 OQKAGNYSLSMLER-UHFFFAOYSA-N 0.000 claims description 2
- DTAIWEPZIOHGGQ-UHFFFAOYSA-N 5-methyl-2-(3-methylphenyl)-4-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound CC1=CC=CC(C=2N=C(OC=3C=C(C=CC=3)C(F)(F)F)C(C)=CN=2)=C1 DTAIWEPZIOHGGQ-UHFFFAOYSA-N 0.000 claims description 2
- FCONHXLFOKSECR-UHFFFAOYSA-N 5-methyl-4-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound Cc1cnc(nc1Oc1cc(nn1C)C(F)(F)F)-c1ccc(cc1)C(F)(F)F FCONHXLFOKSECR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- 230000001629 suppression Effects 0.000 claims description 2
- XBVMBWWRLJQWBN-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-4-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound Cc1cnc(nc1Oc1cc(nn1C)C(F)(F)F)-c1cccc(Cl)c1 XBVMBWWRLJQWBN-UHFFFAOYSA-N 0.000 claims 1
- LTGZKFLEMKMECN-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-4-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound CC1=CN=C(C=2C=C(Cl)C=CC=2)N=C1OC1=CC=CC(C(F)(F)F)=C1 LTGZKFLEMKMECN-UHFFFAOYSA-N 0.000 claims 1
- OVRPAAXFXYKMKB-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(methoxymethyl)-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound COCc1cc(Oc2cc(nn2C)C(F)(F)F)nc(n1)-c1ccc(Cl)cc1 OVRPAAXFXYKMKB-UHFFFAOYSA-N 0.000 claims 1
- KOFQPSOOZPOVKO-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methyl-6-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound N=1C(C=2C=CC(F)=CC=2)=NC(C)=CC=1OC1=CC=CC(C(F)(F)F)=C1 KOFQPSOOZPOVKO-UHFFFAOYSA-N 0.000 claims 1
- IFRRKAWDGMDMMU-UHFFFAOYSA-N 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-6-methyl-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound N=1C(C)=CC(C=2C=3OC(F)(F)OC=3C=CC=2)=NC=1C1=CC=C(C(F)(F)F)C=C1 IFRRKAWDGMDMMU-UHFFFAOYSA-N 0.000 claims 1
- LVVPQVIHVUAFCJ-UHFFFAOYSA-N 4-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound Cn1nc(cc1Oc1ccnc(n1)-c1ccc(cc1)C(F)(F)F)C(F)(F)F LVVPQVIHVUAFCJ-UHFFFAOYSA-N 0.000 claims 1
- IXFDLGLWSGIOHX-UHFFFAOYSA-N 4-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-6-prop-2-ynyl-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound Cn1nc(cc1Oc1cc(CC#C)nc(n1)-c1ccc(cc1)C(F)(F)F)C(F)(F)F IXFDLGLWSGIOHX-UHFFFAOYSA-N 0.000 claims 1
- SGAIFBIYFUJAHZ-UHFFFAOYSA-N 4-chloro-2-[4-(chloromethyl)phenyl]-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound Cn1nc(cc1Oc1cc(Cl)nc(n1)-c1ccc(CCl)cc1)C(F)(F)F SGAIFBIYFUJAHZ-UHFFFAOYSA-N 0.000 claims 1
- DSJWFHWYQHBTEC-UHFFFAOYSA-N 4-chloro-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound Cn1nc(cc1Oc1cc(Cl)nc(n1)-c1ccc(cc1)C(F)(F)F)C(F)(F)F DSJWFHWYQHBTEC-UHFFFAOYSA-N 0.000 claims 1
- UOPNDGYTGROQJP-UHFFFAOYSA-N 4-methyl-6-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazol-3-yl]oxy-2-(4-methylsulfonylphenyl)pyrimidine Chemical compound Cc1cc(Oc2cc(nn2C)C(F)(F)C(F)(F)F)nc(n1)-c1ccc(cc1)S(C)(=O)=O UOPNDGYTGROQJP-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- 125000001309 chloro group Chemical group Cl* 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
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- 239000000741 silica gel Substances 0.000 description 13
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- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 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 6
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- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20011783A CZ290340B6 (cs) | 1995-01-26 | 2001-05-22 | Pyrimidinové deriváty |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95101057 | 1995-01-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ17596A3 CZ17596A3 (en) | 1996-08-14 |
| CZ290330B6 true CZ290330B6 (cs) | 2002-07-17 |
Family
ID=8218937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ1996175A CZ290330B6 (cs) | 1995-01-26 | 1996-01-19 | 2,6-Disubstituované pyridinové a 2,4-disubstituované pyrimidinové deriváty, způsob a meziprodukty pro jejich výrobu, jejich pouľití a herbicidní prostředky na jejich bázi a způsob potlačování růstu neľádoucích rostlin |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5824624A (https=) |
| JP (1) | JP4049405B2 (https=) |
| KR (1) | KR100497135B1 (https=) |
| CN (1) | CN1135227C (https=) |
| AR (1) | AR000795A1 (https=) |
| AT (1) | ATE236124T1 (https=) |
| AU (1) | AU710816B2 (https=) |
| BR (1) | BR9600222A (https=) |
| CA (1) | CA2167982A1 (https=) |
| CZ (1) | CZ290330B6 (https=) |
| DE (1) | DE69627062T2 (https=) |
| HU (1) | HU221864B1 (https=) |
| IL (1) | IL116855A (https=) |
| MX (1) | MX9600347A (https=) |
| RU (1) | RU2134261C1 (https=) |
| SK (1) | SK284993B6 (https=) |
| TR (1) | TR199600065A2 (https=) |
| TW (1) | TW321639B (https=) |
| UA (1) | UA48112C2 (https=) |
| ZA (1) | ZA96529B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5972842A (en) * | 1996-12-12 | 1999-10-26 | American Cyanamid Company | Herbicidal cyanopyridines |
| US6310006B1 (en) | 1997-05-30 | 2001-10-30 | American Cyanamid Company | Herbicidal 3,5-difluoropyridines |
| WO1999024427A1 (en) * | 1997-11-07 | 1999-05-20 | American Cyanamid Company | Herbicidal furanyl- and thienyloxyazines |
| ES2240093T3 (es) * | 1999-04-15 | 2005-10-16 | Basf Aktiengesellschaft | Procedimiento para la preparacion de pirimidinas substituidas. |
| US6281358B1 (en) | 1999-04-15 | 2001-08-28 | American Cyanamid Company | Process for the preparation of substituted pyrimidines |
| AU775959B2 (en) | 1999-11-17 | 2004-08-19 | Bayer Cropscience Ag | Selective herbicides based upon 2,6-disubstituted pyridine derivatives |
| AR029489A1 (es) * | 2000-03-10 | 2003-07-02 | Euro Celtique Sa | Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento |
| DE60127249T2 (de) | 2000-05-19 | 2007-06-21 | Basf Ag | Methode zur bekämpfung unerwünschten pflanzenwuchses in getreide |
| US6894003B2 (en) | 2000-06-23 | 2005-05-17 | Basf Aktiengesellschaft | Enhancement of the activity of carotenoid biosynthesis inhibitor herbicides |
| AR037233A1 (es) | 2001-09-07 | 2004-11-03 | Euro Celtique Sa | Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento |
| WO2005047268A2 (en) * | 2003-11-10 | 2005-05-26 | X-Ceptor Therapeutics, Inc. | Substituted pyrimidine compositions and methods of use |
| JP2009514876A (ja) * | 2005-11-03 | 2009-04-09 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼのための化合物および組成物 |
| EP2279178B1 (en) * | 2008-04-18 | 2015-05-20 | Dow AgroSciences LLC | 2-(substituted phenyl)-6-hydroxy- or alkoxy-5-substituted-4-pyrimidinecarboxylates and their use as herbicides |
| CN119500263B (zh) * | 2024-11-18 | 2026-03-10 | 江苏金申医药科技有限公司 | 克氏反应制备5-甲氧基-4,6-二氯嘧啶的催化剂及方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1585950A (en) * | 1976-08-02 | 1981-03-11 | Ici Ltd | Pyrimidine compoudns and their use as herbicides |
| US4405743A (en) * | 1979-08-31 | 1983-09-20 | Hokko Chemical Industry Co., Ltd. | Pyrazolylpyrimidine derivatives |
| US4366189A (en) * | 1979-12-21 | 1982-12-28 | Ciba-Geigy Corporation | 4-Heterocyclyl-4'-vinylstilbenes |
| DOP1981004033A (es) * | 1980-12-23 | 1990-12-29 | Ciba Geigy Ag | Procedimiento para proteger plantas de cultivo de la accion fitotoxica de herbicidas. |
| GB8333477D0 (en) * | 1983-12-15 | 1984-01-25 | Shell Int Research | Heterocyclic herbicides |
| JPS63107966A (ja) * | 1986-05-22 | 1988-05-12 | Fujisawa Pharmaceut Co Ltd | ピリミジン誘導体 |
| US4849011A (en) * | 1986-09-16 | 1989-07-18 | Sumitomo Chemical Company, Ltd. | 4-substituted-2,6-diphenylpyridine compounds and herbicide containing the same as an active ingredient |
| JP2639049B2 (ja) * | 1988-07-08 | 1997-08-06 | 住友化学工業株式会社 | ピリジルピリミジン誘導体およびそれを有効成分とする農園芸用殺菌剤 |
| DE68910423T2 (de) * | 1988-08-09 | 1994-03-03 | Sumitomo Chemical Co | 5-Substituierte-2,4-Diphenylpyrimidin-Derivate, deren Herstellung und herbizide Verwendung. |
| CA2028341A1 (en) * | 1989-10-23 | 1991-04-24 | Junichi Sato | 5-substituted-2,4-diphenylpyrimidine derivatives, their production and use |
| IE74711B1 (en) * | 1990-07-27 | 1997-07-30 | Ici Plc | Fungicides |
| DE4029654A1 (de) * | 1990-09-19 | 1992-04-02 | Hoechst Ag | 2-phenyl-pyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| TW231258B (https=) * | 1992-05-27 | 1994-10-01 | Shell Internat Res Schappej B V | |
| TW234077B (https=) * | 1992-07-17 | 1994-11-11 | Shell Internat Res Schappej B V | |
| EP0723960B1 (en) * | 1995-01-26 | 2003-04-02 | Basf Aktiengesellschaft | Herbicidal 2,6-disubstituted pyridines and 2,4-disubstituted pyrimidines |
-
1996
- 1996-01-19 CZ CZ1996175A patent/CZ290330B6/cs not_active IP Right Cessation
- 1996-01-22 IL IL11685596A patent/IL116855A/xx not_active IP Right Cessation
- 1996-01-23 ZA ZA96529A patent/ZA96529B/xx unknown
- 1996-01-23 DE DE69627062T patent/DE69627062T2/de not_active Expired - Fee Related
- 1996-01-23 AT AT96300454T patent/ATE236124T1/de not_active IP Right Cessation
- 1996-01-23 UA UA96010278A patent/UA48112C2/uk unknown
- 1996-01-24 AR ARP960101141A patent/AR000795A1/es active IP Right Grant
- 1996-01-24 CA CA002167982A patent/CA2167982A1/en not_active Abandoned
- 1996-01-24 AU AU42164/96A patent/AU710816B2/en not_active Ceased
- 1996-01-24 MX MX9600347A patent/MX9600347A/es not_active IP Right Cessation
- 1996-01-25 RU RU96101815A patent/RU2134261C1/ru not_active IP Right Cessation
- 1996-01-25 JP JP03010196A patent/JP4049405B2/ja not_active Expired - Fee Related
- 1996-01-25 KR KR1019960001585A patent/KR100497135B1/ko not_active Expired - Fee Related
- 1996-01-25 BR BR9600222A patent/BR9600222A/pt not_active IP Right Cessation
- 1996-01-25 SK SK109-96A patent/SK284993B6/sk unknown
- 1996-01-25 HU HU9600161A patent/HU221864B1/hu not_active IP Right Cessation
- 1996-01-26 CN CNB961025476A patent/CN1135227C/zh not_active Expired - Fee Related
- 1996-01-26 TR TR96/00065A patent/TR199600065A2/xx unknown
- 1996-04-09 TW TW085104165A patent/TW321639B/zh active
- 1996-12-06 US US08/761,479 patent/US5824624A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1143078A (zh) | 1997-02-19 |
| ZA96529B (en) | 1997-07-23 |
| CZ17596A3 (en) | 1996-08-14 |
| RU2134261C1 (ru) | 1999-08-10 |
| JP4049405B2 (ja) | 2008-02-20 |
| CN1135227C (zh) | 2004-01-21 |
| BR9600222A (pt) | 1998-01-06 |
| HU221864B1 (hu) | 2003-02-28 |
| MX9600347A (es) | 1997-01-31 |
| TR199600065A2 (tr) | 1996-08-21 |
| IL116855A0 (en) | 1996-07-23 |
| AR000795A1 (es) | 1997-08-06 |
| JPH08277268A (ja) | 1996-10-22 |
| UA48112C2 (uk) | 2002-08-15 |
| ATE236124T1 (de) | 2003-04-15 |
| HUP9600161A2 (en) | 1997-02-28 |
| KR100497135B1 (ko) | 2005-11-16 |
| CA2167982A1 (en) | 1996-07-27 |
| AU710816B2 (en) | 1999-09-30 |
| IL116855A (en) | 2001-01-11 |
| HU9600161D0 (en) | 1996-03-28 |
| SK10996A3 (en) | 1997-09-10 |
| SK284993B6 (sk) | 2006-04-06 |
| TW321639B (https=) | 1997-12-01 |
| HUP9600161A3 (en) | 1997-08-28 |
| DE69627062T2 (de) | 2003-11-06 |
| US5824624A (en) | 1998-10-20 |
| AU4216496A (en) | 1996-08-01 |
| DE69627062D1 (de) | 2003-05-08 |
| KR960029330A (ko) | 1996-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20090119 |