HRP20100077T1 - Spojevi piperazina sa herbicidnim djelovanjem - Google Patents
Spojevi piperazina sa herbicidnim djelovanjem Download PDFInfo
- Publication number
- HRP20100077T1 HRP20100077T1 HR20100077T HRP20100077T HRP20100077T1 HR P20100077 T1 HRP20100077 T1 HR P20100077T1 HR 20100077 T HR20100077 T HR 20100077T HR P20100077 T HRP20100077 T HR P20100077T HR P20100077 T1 HRP20100077 T1 HR P20100077T1
- Authority
- HR
- Croatia
- Prior art keywords
- ethyl
- benzyl
- dioxopiperazin
- fluorobenzyl
- nitrobenzyl
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims 2
- 150000004885 piperazines Chemical class 0.000 title 1
- -1 Piperazine Compound Chemical class 0.000 claims abstract 25
- 239000001257 hydrogen Substances 0.000 claims abstract 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 19
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract 14
- 150000002367 halogens Chemical class 0.000 claims abstract 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000001424 substituent group Chemical group 0.000 claims abstract 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 2
- 125000006413 ring segment Chemical group 0.000 claims abstract 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
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- YAJGVJLYXCZYRZ-UHFFFAOYSA-N 2-[(5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-yl)methyl]-3-fluorobenzonitrile Chemical compound O=C1N(C)C(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(F)C=CC=C1C#N YAJGVJLYXCZYRZ-UHFFFAOYSA-N 0.000 claims 1
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- VXDIDHJWQMYTTJ-UHFFFAOYSA-N 3-[(4-fluorophenyl)methyl]-6-[(2-methoxy-6-nitrophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound COC1=CC=CC([N+]([O-])=O)=C1CC1C(=O)NC(C)(CC=2C=CC(F)=CC=2)C(=O)N1C VXDIDHJWQMYTTJ-UHFFFAOYSA-N 0.000 claims 1
- RELXBSXKYAPEJF-UHFFFAOYSA-N 3-benzyl-1,3,4-trimethyl-6-[(2-methyl-6-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(C)C=CC=C1[N+]([O-])=O RELXBSXKYAPEJF-UHFFFAOYSA-N 0.000 claims 1
- LPCVTOUQOWKVOX-UHFFFAOYSA-N 3-benzyl-1,3,4-trimethyl-6-[(2-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=CC=CC=C1[N+]([O-])=O LPCVTOUQOWKVOX-UHFFFAOYSA-N 0.000 claims 1
- ILHMTZIVNSJMKU-UHFFFAOYSA-N 3-benzyl-1,3-dimethyl-6-[(2-methyl-6-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(C)C=CC=C1[N+]([O-])=O ILHMTZIVNSJMKU-UHFFFAOYSA-N 0.000 claims 1
- PUSITPADJOBTPW-UHFFFAOYSA-N 3-benzyl-1,3-dimethyl-6-[(2-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=CC=CC=C1[N+]([O-])=O PUSITPADJOBTPW-UHFFFAOYSA-N 0.000 claims 1
- WWFRVOSKVSSDJE-UHFFFAOYSA-N 3-benzyl-3-ethyl-1,4-dimethyl-6-[(2-methyl-6-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 WWFRVOSKVSSDJE-UHFFFAOYSA-N 0.000 claims 1
- ZUTQSSDAPMHRKI-UHFFFAOYSA-N 3-benzyl-3-ethyl-1,4-dimethyl-6-[(2-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 ZUTQSSDAPMHRKI-UHFFFAOYSA-N 0.000 claims 1
- JYJYSSPZPJWMEL-UHFFFAOYSA-N 3-benzyl-3-ethyl-1-methyl-6-[(2-methyl-6-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 JYJYSSPZPJWMEL-UHFFFAOYSA-N 0.000 claims 1
- IMGGQQUQTMRKOY-UHFFFAOYSA-N 3-benzyl-3-ethyl-1-methyl-6-[(2-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 IMGGQQUQTMRKOY-UHFFFAOYSA-N 0.000 claims 1
- MXJHXYQEXSARLT-UHFFFAOYSA-N 3-benzyl-3-ethyl-6-[(2-fluoro-6-nitrophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 MXJHXYQEXSARLT-UHFFFAOYSA-N 0.000 claims 1
- HXHUKXCCXIGRJZ-UHFFFAOYSA-N 3-benzyl-3-ethyl-6-[(2-fluoro-6-nitrophenyl)methyl]-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 HXHUKXCCXIGRJZ-UHFFFAOYSA-N 0.000 claims 1
- FXZGMIPFEKFFSI-UHFFFAOYSA-N 3-benzyl-3-ethyl-6-[(2-methoxy-6-nitrophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2OC)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 FXZGMIPFEKFFSI-UHFFFAOYSA-N 0.000 claims 1
- DMFZKROLVPCMLE-UHFFFAOYSA-N 3-benzyl-3-ethyl-6-[(2-methoxy-6-nitrophenyl)methyl]-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2OC)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 DMFZKROLVPCMLE-UHFFFAOYSA-N 0.000 claims 1
- FANVVTMHNPUIRF-UHFFFAOYSA-N 3-benzyl-6-[(2,3-difluoro-6-nitrophenyl)methyl]-1,3,4-trimethylpiperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(F)C(F)=CC=C1[N+]([O-])=O FANVVTMHNPUIRF-UHFFFAOYSA-N 0.000 claims 1
- HWFOBGYIAFHJAT-UHFFFAOYSA-N 3-benzyl-6-[(2,3-difluoro-6-nitrophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(F)C(F)=CC=C1[N+]([O-])=O HWFOBGYIAFHJAT-UHFFFAOYSA-N 0.000 claims 1
- FKYDOXJFCWONFS-UHFFFAOYSA-N 3-benzyl-6-[(2,3-difluoro-6-nitrophenyl)methyl]-3-ethyl-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=C(F)C=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 FKYDOXJFCWONFS-UHFFFAOYSA-N 0.000 claims 1
- NRRQPMBCGCMROY-UHFFFAOYSA-N 3-benzyl-6-[(2,3-difluoro-6-nitrophenyl)methyl]-3-ethyl-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=C(F)C=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 NRRQPMBCGCMROY-UHFFFAOYSA-N 0.000 claims 1
- UOUYSTVMDWILRM-UHFFFAOYSA-N 3-benzyl-6-[(2-ethenyl-6-nitrophenyl)methyl]-1,3,4-trimethylpiperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(C=C)C=CC=C1[N+]([O-])=O UOUYSTVMDWILRM-UHFFFAOYSA-N 0.000 claims 1
- APPUVLYWTJVDHA-UHFFFAOYSA-N 3-benzyl-6-[(2-ethenyl-6-nitrophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(C=C)C=CC=C1[N+]([O-])=O APPUVLYWTJVDHA-UHFFFAOYSA-N 0.000 claims 1
- QGHKRXHLAJZSRK-UHFFFAOYSA-N 3-benzyl-6-[(2-ethenyl-6-nitrophenyl)methyl]-3-ethyl-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2C=C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 QGHKRXHLAJZSRK-UHFFFAOYSA-N 0.000 claims 1
- ZFGSHHFBELDIGX-UHFFFAOYSA-N 3-benzyl-6-[(2-ethenyl-6-nitrophenyl)methyl]-3-ethyl-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2C=C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=CC=C1 ZFGSHHFBELDIGX-UHFFFAOYSA-N 0.000 claims 1
- HIEBOSRCZPWEHF-UHFFFAOYSA-N 3-benzyl-6-[(2-fluoro-6-nitrophenyl)methyl]-1,3,4-trimethylpiperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(F)C=CC=C1[N+]([O-])=O HIEBOSRCZPWEHF-UHFFFAOYSA-N 0.000 claims 1
- VTTCKZVRAMBALI-UHFFFAOYSA-N 3-benzyl-6-[(2-fluoro-6-nitrophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC=CC=2)C(=O)N(C)C1CC1=C(F)C=CC=C1[N+]([O-])=O VTTCKZVRAMBALI-UHFFFAOYSA-N 0.000 claims 1
- IQBXIAGLGKDFIV-UHFFFAOYSA-N 3-benzyl-6-[(2-methoxy-6-nitrophenyl)methyl]-1,3,4-trimethylpiperazine-2,5-dione Chemical compound COC1=CC=CC([N+]([O-])=O)=C1CC1C(=O)N(C)C(C)(CC=2C=CC=CC=2)C(=O)N1C IQBXIAGLGKDFIV-UHFFFAOYSA-N 0.000 claims 1
- JDLJQFBNSFNIKH-UHFFFAOYSA-N 3-benzyl-6-[(2-methoxy-6-nitrophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound COC1=CC=CC([N+]([O-])=O)=C1CC1C(=O)NC(C)(CC=2C=CC=CC=2)C(=O)N1C JDLJQFBNSFNIKH-UHFFFAOYSA-N 0.000 claims 1
- HKAXAQUIQIBEEJ-UHFFFAOYSA-N 3-ethenyl-2-[[5-[(4-fluorophenyl)methyl]-1,4,5-trimethyl-3,6-dioxopiperazin-2-yl]methyl]benzonitrile Chemical compound O=C1N(C)C(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(C=C)C=CC=C1C#N HKAXAQUIQIBEEJ-UHFFFAOYSA-N 0.000 claims 1
- LKNRLAWNZUPYTC-UHFFFAOYSA-N 3-ethenyl-2-[[5-[(4-fluorophenyl)methyl]-1,5-dimethyl-3,6-dioxopiperazin-2-yl]methyl]benzonitrile Chemical compound O=C1NC(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(C=C)C=CC=C1C#N LKNRLAWNZUPYTC-UHFFFAOYSA-N 0.000 claims 1
- UINVYPVXUCWMPS-UHFFFAOYSA-N 3-ethenyl-2-[[5-ethyl-5-[(4-fluorophenyl)methyl]-1,4-dimethyl-3,6-dioxopiperazin-2-yl]methyl]benzonitrile Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2C=C)C#N)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 UINVYPVXUCWMPS-UHFFFAOYSA-N 0.000 claims 1
- QLUYMTOFYDEBPE-UHFFFAOYSA-N 3-ethenyl-2-[[5-ethyl-5-[(4-fluorophenyl)methyl]-1-methyl-3,6-dioxopiperazin-2-yl]methyl]benzonitrile Chemical compound N1C(=O)C(CC=2C(=CC=CC=2C=C)C#N)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 QLUYMTOFYDEBPE-UHFFFAOYSA-N 0.000 claims 1
- MFUAKDCAJUSEGY-UHFFFAOYSA-N 3-ethyl-3-[(4-fluorophenyl)methyl]-1,4-dimethyl-6-[(2-methyl-6-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 MFUAKDCAJUSEGY-UHFFFAOYSA-N 0.000 claims 1
- KIAXIFQQDISDSN-UHFFFAOYSA-N 3-ethyl-3-[(4-fluorophenyl)methyl]-1,4-dimethyl-6-[(2-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 KIAXIFQQDISDSN-UHFFFAOYSA-N 0.000 claims 1
- VMSQGCVFJPYZHG-UHFFFAOYSA-N 3-ethyl-3-[(4-fluorophenyl)methyl]-1-methyl-6-[(2-methyl-6-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 VMSQGCVFJPYZHG-UHFFFAOYSA-N 0.000 claims 1
- DLDSVHAOCORHTA-UHFFFAOYSA-N 3-ethyl-3-[(4-fluorophenyl)methyl]-1-methyl-6-[(2-nitrophenyl)methyl]piperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 DLDSVHAOCORHTA-UHFFFAOYSA-N 0.000 claims 1
- DENVEBGXGLIDTB-UHFFFAOYSA-N 3-ethyl-3-[(4-fluorophenyl)methyl]-6-[(2-methoxy-6-nitrophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2OC)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 DENVEBGXGLIDTB-UHFFFAOYSA-N 0.000 claims 1
- JNLVHKNSRMBJLX-UHFFFAOYSA-N 3-ethyl-3-[(4-fluorophenyl)methyl]-6-[(2-methoxy-6-nitrophenyl)methyl]-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2OC)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 JNLVHKNSRMBJLX-UHFFFAOYSA-N 0.000 claims 1
- VGHVPWCEICQUQG-UHFFFAOYSA-N 3-ethyl-6-[(2-fluoro-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 VGHVPWCEICQUQG-UHFFFAOYSA-N 0.000 claims 1
- DLWHMRQJMNXIQA-UHFFFAOYSA-N 3-ethyl-6-[(2-fluoro-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 DLWHMRQJMNXIQA-UHFFFAOYSA-N 0.000 claims 1
- FOJGRNSAPSGSDD-UHFFFAOYSA-N 3-fluoro-2-[[5-[(4-fluorophenyl)methyl]-1,4,5-trimethyl-3,6-dioxopiperazin-2-yl]methyl]benzonitrile Chemical compound O=C1N(C)C(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(F)C=CC=C1C#N FOJGRNSAPSGSDD-UHFFFAOYSA-N 0.000 claims 1
- LUJOATDBVVIKNW-UHFFFAOYSA-N 3-fluoro-2-[[5-[(4-fluorophenyl)methyl]-1,5-dimethyl-3,6-dioxopiperazin-2-yl]methyl]benzonitrile Chemical compound O=C1NC(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(F)C=CC=C1C#N LUJOATDBVVIKNW-UHFFFAOYSA-N 0.000 claims 1
- ZIDITEJRTXNPLR-UHFFFAOYSA-N 6-[(2,3-difluoro-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1,3,4-trimethylpiperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(F)C(F)=CC=C1[N+]([O-])=O ZIDITEJRTXNPLR-UHFFFAOYSA-N 0.000 claims 1
- KJYFOJOATMIQKA-UHFFFAOYSA-N 6-[(2,3-difluoro-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(F)C(F)=CC=C1[N+]([O-])=O KJYFOJOATMIQKA-UHFFFAOYSA-N 0.000 claims 1
- MWYRIKPMRVIIME-UHFFFAOYSA-N 6-[(2,3-difluoro-6-nitrophenyl)methyl]-3-ethyl-3-[(4-fluorophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=C(F)C=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 MWYRIKPMRVIIME-UHFFFAOYSA-N 0.000 claims 1
- ANIMTDNHLDAJME-UHFFFAOYSA-N 6-[(2,3-difluoro-6-nitrophenyl)methyl]-3-ethyl-3-[(4-fluorophenyl)methyl]-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=C(F)C=2F)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 ANIMTDNHLDAJME-UHFFFAOYSA-N 0.000 claims 1
- NCWIQHJURLWUDU-UHFFFAOYSA-N 6-[(2-ethenyl-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1,3,4-trimethylpiperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(C=C)C=CC=C1[N+]([O-])=O NCWIQHJURLWUDU-UHFFFAOYSA-N 0.000 claims 1
- LIVGMDFWLOUQEP-UHFFFAOYSA-N 6-[(2-ethenyl-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(C=C)C=CC=C1[N+]([O-])=O LIVGMDFWLOUQEP-UHFFFAOYSA-N 0.000 claims 1
- JXKXXGHOTQRNCP-UHFFFAOYSA-N 6-[(2-ethenyl-6-nitrophenyl)methyl]-3-ethyl-3-[(4-fluorophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione Chemical compound CN1C(=O)C(CC=2C(=CC=CC=2C=C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 JXKXXGHOTQRNCP-UHFFFAOYSA-N 0.000 claims 1
- FURHVLYOHYKDNL-UHFFFAOYSA-N 6-[(2-ethenyl-6-nitrophenyl)methyl]-3-ethyl-3-[(4-fluorophenyl)methyl]-1-methylpiperazine-2,5-dione Chemical compound N1C(=O)C(CC=2C(=CC=CC=2C=C)[N+]([O-])=O)N(C)C(=O)C1(CC)CC1=CC=C(F)C=C1 FURHVLYOHYKDNL-UHFFFAOYSA-N 0.000 claims 1
- XRJZZYCXAQGWOJ-UHFFFAOYSA-N 6-[(2-fluoro-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1,3,4-trimethylpiperazine-2,5-dione Chemical compound O=C1N(C)C(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(F)C=CC=C1[N+]([O-])=O XRJZZYCXAQGWOJ-UHFFFAOYSA-N 0.000 claims 1
- IHMMUKVEAYRZJN-UHFFFAOYSA-N 6-[(2-fluoro-6-nitrophenyl)methyl]-3-[(4-fluorophenyl)methyl]-1,3-dimethylpiperazine-2,5-dione Chemical compound O=C1NC(C)(CC=2C=CC(F)=CC=2)C(=O)N(C)C1CC1=C(F)C=CC=C1[N+]([O-])=O IHMMUKVEAYRZJN-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000011814 protection agent Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07110125 | 2007-06-12 | ||
| PCT/EP2008/057328 WO2008152072A2 (de) | 2007-06-12 | 2008-06-11 | Piperazinverbindungen mit herbizider wirkung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100077T1 true HRP20100077T1 (hr) | 2010-04-30 |
Family
ID=39832461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100077T HRP20100077T1 (hr) | 2007-06-12 | 2010-02-15 | Spojevi piperazina sa herbicidnim djelovanjem |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US20100173777A1 (es) |
| EP (1) | EP2054394B1 (es) |
| JP (1) | JP2010529168A (es) |
| KR (1) | KR20100018065A (es) |
| CN (1) | CN101679316A (es) |
| AR (1) | AR068075A1 (es) |
| AT (1) | ATE449085T1 (es) |
| AU (1) | AU2008263901A1 (es) |
| BR (1) | BRPI0812877A2 (es) |
| CA (1) | CA2689529A1 (es) |
| CL (1) | CL2008001751A1 (es) |
| CY (1) | CY1109821T1 (es) |
| DE (1) | DE502008000206D1 (es) |
| DK (1) | DK2054394T3 (es) |
| EA (1) | EA200901659A1 (es) |
| ES (1) | ES2336390T3 (es) |
| HR (1) | HRP20100077T1 (es) |
| IL (1) | IL202074A0 (es) |
| PE (1) | PE20090334A1 (es) |
| PL (1) | PL2054394T3 (es) |
| PT (1) | PT2054394E (es) |
| RS (1) | RS51224B (es) |
| SI (1) | SI2054394T1 (es) |
| TW (1) | TW200906805A (es) |
| UY (1) | UY31140A1 (es) |
| WO (1) | WO2008152072A2 (es) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101702907A (zh) * | 2007-06-12 | 2010-05-05 | 巴斯夫欧洲公司 | 具有除草活性的哌嗪化合物 |
| CA2690072A1 (en) * | 2007-06-12 | 2008-12-18 | Eike Hupe | Herbicidally active composition |
| US8097712B2 (en) | 2007-11-07 | 2012-01-17 | Beelogics Inc. | Compositions for conferring tolerance to viral disease in social insects, and the use thereof |
| US20110130286A1 (en) * | 2008-07-29 | 2011-06-02 | Basf Se | Piperazine Compounds with Herbicidal Effect |
| US20110144336A1 (en) * | 2008-08-13 | 2011-06-16 | Basf Se | Method for Preparation of Piperazindione Derivatives |
| JP2012504576A (ja) * | 2008-10-02 | 2012-02-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草活性を有するピペラジン化合物 |
| WO2010069819A1 (de) * | 2008-12-19 | 2010-06-24 | Basf Se | Verfahren zur herstellung von piperazindion-derivaten |
| US9968085B2 (en) | 2008-12-31 | 2018-05-15 | Marrone Bio Innovations, Inc. | Uses of thaxtomin and thaxtomin compositions as herbicides |
| TW201024278A (en) * | 2008-12-31 | 2010-07-01 | Marrone Bio Innovations Inc | Uses of thaxtomin and thaxtomin compositions as herbicides |
| US8962584B2 (en) | 2009-10-14 | 2015-02-24 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Compositions for controlling Varroa mites in bees |
| ES2809679T3 (es) | 2010-03-08 | 2021-03-05 | Monsanto Technology Llc | Moléculas polinucleotídicas para la regulación génica en plantas |
| KR101278140B1 (ko) * | 2010-07-15 | 2013-06-27 | 공주대학교 산학협력단 | 2,5-다이케토피페라진 유도체를 활성성분으로 포함하는 농업용 약제 |
| US10760086B2 (en) | 2011-09-13 | 2020-09-01 | Monsanto Technology Llc | Methods and compositions for weed control |
| MX342856B (es) | 2011-09-13 | 2016-10-13 | Monsanto Technology Llc | Metodos y composiciones para el control de malezas. |
| WO2013040057A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control |
| EP2756083B1 (en) | 2011-09-13 | 2020-08-19 | Monsanto Technology LLC | Methods and compositions for weed control |
| BR112014005951A2 (pt) | 2011-09-13 | 2017-04-04 | Monsanto Technology Llc | métodos e composições para controle de erva daninha |
| US10829828B2 (en) | 2011-09-13 | 2020-11-10 | Monsanto Technology Llc | Methods and compositions for weed control |
| CN103974967A (zh) | 2011-09-13 | 2014-08-06 | 孟山都技术公司 | 用于杂草控制的方法和组合物 |
| US10806146B2 (en) | 2011-09-13 | 2020-10-20 | Monsanto Technology Llc | Methods and compositions for weed control |
| MX348495B (es) | 2011-09-13 | 2017-06-14 | Monsanto Technology Llc | Metodos y composiciones para el control de malezas. |
| EP3382027A3 (en) | 2011-09-13 | 2018-10-31 | Monsanto Technology LLC | Methods and compositions for weed control |
| US10240161B2 (en) | 2012-05-24 | 2019-03-26 | A.B. Seeds Ltd. | Compositions and methods for silencing gene expression |
| US10683505B2 (en) | 2013-01-01 | 2020-06-16 | Monsanto Technology Llc | Methods of introducing dsRNA to plant seeds for modulating gene expression |
| BR112015015976A2 (pt) | 2013-01-01 | 2018-04-10 | A. B. Seeds Ltd. | método para introduzir dsrna em sementes para modular a expressão genética |
| US10609930B2 (en) | 2013-03-13 | 2020-04-07 | Monsanto Technology Llc | Methods and compositions for weed control |
| WO2014164797A2 (en) | 2013-03-13 | 2014-10-09 | Monsanto Technology Llc | Methods and compositions for weed control |
| US8993762B2 (en) * | 2013-03-15 | 2015-03-31 | Marrone Bio Innovations, Inc. | Total synthesis of thaxtomin A analogues and their intermediates |
| US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| RU2703498C2 (ru) | 2013-07-19 | 2019-10-17 | Монсанто Текнолоджи Ллс | Композиции и способы борьбы с leptinotarsa |
| US9850496B2 (en) | 2013-07-19 | 2017-12-26 | Monsanto Technology Llc | Compositions and methods for controlling Leptinotarsa |
| UA120426C2 (uk) | 2013-11-04 | 2019-12-10 | Монсанто Текнолоджі Елелсі | Композиція та спосіб для боротьби з членистоногими паразитами та зараженням шкідниками |
| UA119253C2 (uk) | 2013-12-10 | 2019-05-27 | Біолоджикс, Інк. | Спосіб боротьби із вірусом у кліща varroa та у бджіл |
| MX368629B (es) | 2014-01-15 | 2019-10-08 | Monsanto Technology Llc | Metodos y composiciones para el control de malezas utilizando polinucleotidos de 5-enolpiruvilshikimato-3-fosfato sintasa (epsps). |
| WO2015153339A2 (en) | 2014-04-01 | 2015-10-08 | Monsanto Technology Llc | Compositions and methods for controlling insect pests |
| CN106795515B (zh) | 2014-06-23 | 2021-06-08 | 孟山都技术公司 | 用于经由rna干扰调控基因表达的组合物和方法 |
| US11807857B2 (en) | 2014-06-25 | 2023-11-07 | Monsanto Technology Llc | Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression |
| WO2016018887A1 (en) | 2014-07-29 | 2016-02-04 | Monsanto Technology Llc | Compositions and methods for controlling insect pests |
| PL3256589T3 (pl) | 2015-01-22 | 2022-02-21 | Monsanto Technology Llc | Kompozycje i sposoby kontrolowania leptinotarsa |
| EP3302053B1 (en) | 2015-06-02 | 2021-03-17 | Monsanto Technology LLC | Compositions and methods for delivery of a polynucleotide into a plant |
| WO2016196782A1 (en) | 2015-06-03 | 2016-12-08 | Monsanto Technology Llc | Methods and compositions for introducing nucleic acids into plants |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL150430A0 (en) * | 2000-01-18 | 2002-12-01 | Nereus Pharmaceuticals Inc | Cell division inhibitors and process for producing the same |
| US20030171379A1 (en) * | 2001-12-28 | 2003-09-11 | Jacobs Robert S. | Methods of treating, preventing, or inhibiting inflammation with Mactanamide compounds |
| AR058408A1 (es) * | 2006-01-02 | 2008-01-30 | Basf Ag | Compuestos de piperazina con accion herbicida |
| KR20080092407A (ko) * | 2006-01-05 | 2008-10-15 | 바스프 에스이 | 제초 작용을 갖는 피페라진 화합물 |
| CA2690072A1 (en) * | 2007-06-12 | 2008-12-18 | Eike Hupe | Herbicidally active composition |
| CN101702907A (zh) * | 2007-06-12 | 2010-05-05 | 巴斯夫欧洲公司 | 具有除草活性的哌嗪化合物 |
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2008
- 2008-06-11 RS RSP-2010/0033A patent/RS51224B/sr unknown
- 2008-06-11 SI SI200830010T patent/SI2054394T1/sl unknown
- 2008-06-11 JP JP2010511629A patent/JP2010529168A/ja not_active Withdrawn
- 2008-06-11 BR BRPI0812877-4A2A patent/BRPI0812877A2/pt not_active Application Discontinuation
- 2008-06-11 US US12/663,781 patent/US20100173777A1/en not_active Abandoned
- 2008-06-11 TW TW097121793A patent/TW200906805A/zh unknown
- 2008-06-11 ES ES08760876T patent/ES2336390T3/es active Active
- 2008-06-11 DK DK08760876.6T patent/DK2054394T3/da active
- 2008-06-11 PL PL08760876T patent/PL2054394T3/pl unknown
- 2008-06-11 KR KR1020107000613A patent/KR20100018065A/ko not_active Application Discontinuation
- 2008-06-11 CN CN200880019741A patent/CN101679316A/zh active Pending
- 2008-06-11 EP EP08760876A patent/EP2054394B1/de active Active
- 2008-06-11 AU AU2008263901A patent/AU2008263901A1/en not_active Abandoned
- 2008-06-11 UY UY31140A patent/UY31140A1/es unknown
- 2008-06-11 CA CA2689529A patent/CA2689529A1/en not_active Abandoned
- 2008-06-11 PT PT08760876T patent/PT2054394E/pt unknown
- 2008-06-11 EA EA200901659A patent/EA200901659A1/ru unknown
- 2008-06-11 DE DE502008000206T patent/DE502008000206D1/de active Active
- 2008-06-11 PE PE2008000995A patent/PE20090334A1/es not_active Application Discontinuation
- 2008-06-11 WO PCT/EP2008/057328 patent/WO2008152072A2/de active Application Filing
- 2008-06-11 AT AT08760876T patent/ATE449085T1/de active
- 2008-06-11 AR ARP080102494A patent/AR068075A1/es not_active Application Discontinuation
- 2008-06-12 CL CL2008001751A patent/CL2008001751A1/es unknown
-
2009
- 2009-11-12 IL IL202074A patent/IL202074A0/en unknown
-
2010
- 2010-02-15 HR HR20100077T patent/HRP20100077T1/hr unknown
- 2010-02-17 CY CY20101100156T patent/CY1109821T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008152072A2 (de) | 2008-12-18 |
| US20100173777A1 (en) | 2010-07-08 |
| PT2054394E (pt) | 2009-12-30 |
| EP2054394A2 (de) | 2009-05-06 |
| TW200906805A (en) | 2009-02-16 |
| CY1109821T1 (el) | 2014-09-10 |
| DK2054394T3 (da) | 2010-03-29 |
| RS51224B (sr) | 2010-12-31 |
| ATE449085T1 (de) | 2009-12-15 |
| KR20100018065A (ko) | 2010-02-16 |
| CA2689529A1 (en) | 2008-12-18 |
| BRPI0812877A2 (pt) | 2014-12-09 |
| AR068075A1 (es) | 2009-11-04 |
| WO2008152072A3 (de) | 2009-02-12 |
| CL2008001751A1 (es) | 2009-12-11 |
| EA200901659A1 (ru) | 2010-06-30 |
| DE502008000206D1 (de) | 2009-12-31 |
| IL202074A0 (en) | 2010-06-16 |
| SI2054394T1 (sl) | 2010-02-26 |
| JP2010529168A (ja) | 2010-08-26 |
| UY31140A1 (es) | 2009-01-05 |
| ES2336390T3 (es) | 2010-04-12 |
| PE20090334A1 (es) | 2009-04-26 |
| CN101679316A (zh) | 2010-03-24 |
| PL2054394T3 (pl) | 2010-04-30 |
| AU2008263901A1 (en) | 2008-12-18 |
| EP2054394B1 (de) | 2009-11-18 |
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