CN1052478C - 1,4-二取代-5(4h)-四唑啉酮类的制备方法 - Google Patents
1,4-二取代-5(4h)-四唑啉酮类的制备方法 Download PDFInfo
- Publication number
- CN1052478C CN1052478C CN94116998A CN94116998A CN1052478C CN 1052478 C CN1052478 C CN 1052478C CN 94116998 A CN94116998 A CN 94116998A CN 94116998 A CN94116998 A CN 94116998A CN 1052478 C CN1052478 C CN 1052478C
- Authority
- CN
- China
- Prior art keywords
- group
- ethyl
- tetrazolinone
- general formula
- propyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 36
- -1 methylene-dioxy Chemical group 0.000 claims description 150
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical compound OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000006038 hexenyl group Chemical group 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 3
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 1
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical group CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000790917 Dioxys <bee> Species 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 4
- OWRABTHGOKNUDV-UHFFFAOYSA-N n,n-dipropylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)CCC OWRABTHGOKNUDV-UHFFFAOYSA-N 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
- 125000004995 haloalkylthio group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- CJENPNUXCMYXPT-UHFFFAOYSA-N 1-chloro-1,2-difluoroethene Chemical group FC=C(F)Cl CJENPNUXCMYXPT-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 125000000262 haloalkenyl group Chemical group 0.000 description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NTLCSWYRVIMNEI-UHFFFAOYSA-N 1-(2-chlorophenyl)-2h-tetrazol-5-one Chemical compound ClC1=CC=CC=C1N1C(=O)N=NN1 NTLCSWYRVIMNEI-UHFFFAOYSA-N 0.000 description 1
- LDKSCZJUIURGMW-UHFFFAOYSA-N 1-isothiocyanato-3-methylsulfanylpropane Chemical group CSCCCN=C=S LDKSCZJUIURGMW-UHFFFAOYSA-N 0.000 description 1
- IRNAEDHJBNPCEZ-UHFFFAOYSA-N 1-n,1-n,2-trimethylpropane-1,2-diamine Chemical compound CN(C)CC(C)(C)N IRNAEDHJBNPCEZ-UHFFFAOYSA-N 0.000 description 1
- LEWYUUYUTMWBIB-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydroindole-1-carbonyl chloride Chemical compound C1CCCC2N(C(=O)Cl)CCC21 LEWYUUYUTMWBIB-UHFFFAOYSA-N 0.000 description 1
- BHVDNQHSQZMQMJ-UHFFFAOYSA-N 2,3-dihydroindole-1-carbonyl chloride Chemical compound C1=CC=C2N(C(=O)Cl)CCC2=C1 BHVDNQHSQZMQMJ-UHFFFAOYSA-N 0.000 description 1
- ROBIABICEDEGND-UHFFFAOYSA-N 2,6-dimethylmorpholine-4-carbonyl chloride Chemical compound CC1CN(C(Cl)=O)CC(C)O1 ROBIABICEDEGND-UHFFFAOYSA-N 0.000 description 1
- JOPVMXGJULJMLT-UHFFFAOYSA-N 2,6-dimethylpiperidine-1-carbonyl chloride Chemical compound CC1CCCC(C)N1C(Cl)=O JOPVMXGJULJMLT-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- HHZMCYNIZCNDEN-UHFFFAOYSA-N 5-oxo-2h-tetrazole-1-carboxamide Chemical class NC(=O)N1N=NNC1=O HHZMCYNIZCNDEN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- MRLBJLFKPYKIEB-UHFFFAOYSA-N [1-(2-chloro-6-methylphenyl)tetrazol-5-yl] n,n-dipropylcarbamate Chemical compound CCCN(CCC)C(=O)OC1=NN=NN1C1=C(C)C=CC=C1Cl MRLBJLFKPYKIEB-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 125000006005 fluoroethoxy group Chemical group 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- MGQPJLWKFQNTOZ-UHFFFAOYSA-N n,n-bis(prop-2-enyl)carbamoyl chloride Chemical compound C=CCN(C(=O)Cl)CC=C MGQPJLWKFQNTOZ-UHFFFAOYSA-N 0.000 description 1
- RSAFAYLZKCYUQW-UHFFFAOYSA-N n,n-di(propan-2-yl)carbamoyl chloride Chemical compound CC(C)N(C(C)C)C(Cl)=O RSAFAYLZKCYUQW-UHFFFAOYSA-N 0.000 description 1
- OSWBZCCZJXCOGL-UHFFFAOYSA-N n,n-dibutylcarbamoyl chloride Chemical compound CCCCN(C(Cl)=O)CCCC OSWBZCCZJXCOGL-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- GECHIYCHFMSDEG-UHFFFAOYSA-N n-(3-methylphenyl)-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C1=CC=CC(C)=C1 GECHIYCHFMSDEG-UHFFFAOYSA-N 0.000 description 1
- TXPQWRDQZHUSRG-UHFFFAOYSA-N n-(4-chlorophenyl)-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C1=CC=C(Cl)C=C1 TXPQWRDQZHUSRG-UHFFFAOYSA-N 0.000 description 1
- XWHDZSVRJFJXOV-UHFFFAOYSA-N n-(4-fluorophenyl)-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C1=CC=C(F)C=C1 XWHDZSVRJFJXOV-UHFFFAOYSA-N 0.000 description 1
- UGDGWNIGGXSMLK-UHFFFAOYSA-N n-butan-2-yl-n-ethylcarbamoyl chloride Chemical compound CCC(C)N(CC)C(Cl)=O UGDGWNIGGXSMLK-UHFFFAOYSA-N 0.000 description 1
- BXUGIUJAIPSZHD-UHFFFAOYSA-N n-butyl-n-cyclopropylcarbamoyl chloride Chemical compound CCCCN(C(Cl)=O)C1CC1 BXUGIUJAIPSZHD-UHFFFAOYSA-N 0.000 description 1
- ONKIPJDBUYZQMP-UHFFFAOYSA-N n-cyclohexyl-n-ethylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1CCCCC1 ONKIPJDBUYZQMP-UHFFFAOYSA-N 0.000 description 1
- KHAMSOPQAFGFHX-UHFFFAOYSA-N n-cyclohexyl-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C1CCCCC1 KHAMSOPQAFGFHX-UHFFFAOYSA-N 0.000 description 1
- OIWLZSJMOSNWOC-UHFFFAOYSA-N n-cyclohexyl-n-propylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)C1CCCCC1 OIWLZSJMOSNWOC-UHFFFAOYSA-N 0.000 description 1
- YDQLTMBHLYQVNT-UHFFFAOYSA-N n-cyclopentyl-n-ethylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1CCCC1 YDQLTMBHLYQVNT-UHFFFAOYSA-N 0.000 description 1
- GWNFJNPQTPBLES-UHFFFAOYSA-N n-cyclopentyl-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C1CCCC1 GWNFJNPQTPBLES-UHFFFAOYSA-N 0.000 description 1
- LQABTSBNFVWXAB-UHFFFAOYSA-N n-cyclopentyl-n-propylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)C1CCCC1 LQABTSBNFVWXAB-UHFFFAOYSA-N 0.000 description 1
- DADCLFBPAHGHKB-UHFFFAOYSA-N n-ethoxy-n-propylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)OCC DADCLFBPAHGHKB-UHFFFAOYSA-N 0.000 description 1
- PHXNYRJTLCGBCS-UHFFFAOYSA-N n-ethyl-n-(2-methylpropyl)carbamoyl chloride Chemical compound CCN(C(Cl)=O)CC(C)C PHXNYRJTLCGBCS-UHFFFAOYSA-N 0.000 description 1
- XZVYDRLPXWFRIS-UHFFFAOYSA-N n-ethyl-n-methylcarbamoyl chloride Chemical compound CCN(C)C(Cl)=O XZVYDRLPXWFRIS-UHFFFAOYSA-N 0.000 description 1
- CDGCUPPKLDOYGV-UHFFFAOYSA-N n-ethyl-n-phenylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1=CC=CC=C1 CDGCUPPKLDOYGV-UHFFFAOYSA-N 0.000 description 1
- SVLNCPUVMJGVFR-UHFFFAOYSA-N n-ethyl-n-propan-2-ylcarbamoyl chloride Chemical compound CCN(C(C)C)C(Cl)=O SVLNCPUVMJGVFR-UHFFFAOYSA-N 0.000 description 1
- ZTBGJRUHDDPDEK-UHFFFAOYSA-N n-ethyl-n-propylcarbamoyl chloride Chemical compound CCCN(CC)C(Cl)=O ZTBGJRUHDDPDEK-UHFFFAOYSA-N 0.000 description 1
- LFGQCGXMPNCCRC-UHFFFAOYSA-N n-methoxy-n-propylcarbamoyl chloride Chemical compound CCCN(OC)C(Cl)=O LFGQCGXMPNCCRC-UHFFFAOYSA-N 0.000 description 1
- KAPFLERFQZXFBX-UHFFFAOYSA-N n-methyl-n-[2-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC=C1C(F)(F)F KAPFLERFQZXFBX-UHFFFAOYSA-N 0.000 description 1
- XQGGZMYUSYDFFV-UHFFFAOYSA-N n-methyl-n-[3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC(C(F)(F)F)=C1 XQGGZMYUSYDFFV-UHFFFAOYSA-N 0.000 description 1
- CPGWSLFYXMRNDV-UHFFFAOYSA-N n-methyl-n-phenylcarbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC=C1 CPGWSLFYXMRNDV-UHFFFAOYSA-N 0.000 description 1
- HXKLJAOQHIUGBC-UHFFFAOYSA-N n-phenyl-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C1=CC=CC=C1 HXKLJAOQHIUGBC-UHFFFAOYSA-N 0.000 description 1
- HIENBQZSBONJNN-UHFFFAOYSA-N n-phenyl-n-propylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)C1=CC=CC=C1 HIENBQZSBONJNN-UHFFFAOYSA-N 0.000 description 1
- HXYIGPLMKRWWIB-UHFFFAOYSA-N n-propan-2-yl-n-(3-propylphenyl)carbamoyl chloride Chemical compound CCCC1=CC=CC(N(C(C)C)C(Cl)=O)=C1 HXYIGPLMKRWWIB-UHFFFAOYSA-N 0.000 description 1
- KGWOPOPZYCZBTI-UHFFFAOYSA-N n-propan-2-yl-n-[3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C1=CC=CC(C(F)(F)F)=C1 KGWOPOPZYCZBTI-UHFFFAOYSA-N 0.000 description 1
- KMTHFGHAXJWFLL-UHFFFAOYSA-N n-propan-2-yl-n-propylcarbamoyl chloride Chemical compound CCCN(C(C)C)C(Cl)=O KMTHFGHAXJWFLL-UHFFFAOYSA-N 0.000 description 1
- OMSOVIPYSZIAKS-UHFFFAOYSA-N n-tert-butyl-n-ethylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C(C)(C)C OMSOVIPYSZIAKS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- GSQGGQTWPPNNGZ-UHFFFAOYSA-N thiomorpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCSCC1 GSQGGQTWPPNNGZ-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26541793A JP3390499B2 (ja) | 1993-09-30 | 1993-09-30 | テトラゾリノン類の製造方法 |
| JP265417/93 | 1993-09-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1102183A CN1102183A (zh) | 1995-05-03 |
| CN1052478C true CN1052478C (zh) | 2000-05-17 |
Family
ID=17416877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94116998A Expired - Fee Related CN1052478C (zh) | 1993-09-30 | 1994-09-30 | 1,4-二取代-5(4h)-四唑啉酮类的制备方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5767286A (enExample) |
| EP (1) | EP0646577B1 (enExample) |
| JP (1) | JP3390499B2 (enExample) |
| KR (1) | KR100345045B1 (enExample) |
| CN (1) | CN1052478C (enExample) |
| BR (1) | BR9403944A (enExample) |
| DE (1) | DE69410722T2 (enExample) |
| ES (1) | ES2116496T3 (enExample) |
| HU (1) | HU216275B (enExample) |
| TW (1) | TW245715B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3694051B2 (ja) * | 1994-07-12 | 2005-09-14 | バイエルクロップサイエンス株式会社 | １−ピリジルテトラゾリノン誘導体および除草剤 |
| JPH08193074A (ja) * | 1994-11-18 | 1996-07-30 | Nippon Bayeragrochem Kk | 除草性１−シクロプロピルテトラゾリノン類 |
| DE19504059A1 (de) * | 1995-02-08 | 1996-08-14 | Bayer Ag | Verfahren zur Herstellung von substituierten N-Carbamoyl-tetrazolinonen |
| JPH08225547A (ja) * | 1995-02-22 | 1996-09-03 | Nippon Bayeragrochem Kk | 除草性 １−シクロアルケニルテトラゾリノン類 |
| EP0732326A1 (en) * | 1995-03-13 | 1996-09-18 | Nihon Bayer Agrochem K.K. | Herbicidally active tetrazolinones |
| JPH08259547A (ja) * | 1995-03-20 | 1996-10-08 | Nippon Bayeragrochem Kk | 除草性１−アルケニルテトラゾリノン類 |
| JPH08259548A (ja) * | 1995-03-23 | 1996-10-08 | Nippon Bayeragrochem Kk | テトラゾリノン類及び除草剤 |
| DE19535242A1 (de) * | 1995-09-22 | 1997-03-27 | Bayer Ag | Verfahren zur Herstellung von 1-Aryl-4-carbamoyl-tetrazolinonen |
| US5874586A (en) * | 1995-09-22 | 1999-02-23 | Bayer Aktiengesellschaft | Process for preparing 1-aryl-4-carbamoyl-tetrazolinones |
| JPH09183770A (ja) * | 1995-10-31 | 1997-07-15 | Nippon Bayeragrochem Kk | １−アジン−テトラゾリノン類及び除草剤 |
| US6017853A (en) * | 1996-07-16 | 2000-01-25 | Nihon Bayer Agrochem K.K. | Herbicidal 1-substituted methyl-tetrazolinones |
| AU5519098A (en) * | 1996-12-13 | 1998-07-03 | E.I. Du Pont De Nemours And Company | Herbicidal heterocyclic amides |
| WO1999007702A1 (de) * | 1997-08-06 | 1999-02-18 | Basf Aktiengesellschaft | Substituierte herbizide tetrazolinoncarbonsäureamide |
| JP2000256331A (ja) * | 1999-01-08 | 2000-09-19 | Nippon Bayer Agrochem Co Ltd | テトラゾリノン誘導体および除草剤としてのその用途 |
| JP2000327668A (ja) * | 1999-05-21 | 2000-11-28 | Nippon Bayer Agrochem Co Ltd | テトラゾリノン誘導体 |
| WO2011140190A1 (en) * | 2010-05-05 | 2011-11-10 | Infinity Pharmaceuticals | Tetrazolones as inhibitors of fatty acid synthase |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4618365A (en) * | 1983-12-09 | 1986-10-21 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones and their use as herbicides |
| EP0202929A2 (en) * | 1985-05-23 | 1986-11-26 | UNIROYAL CHEMICAL COMPANY, Inc. | Substituted tetrazolinones |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4985065A (en) * | 1989-05-10 | 1991-01-15 | Fmc Corporation | Tetrazolinone herbicides |
| JP3102953B2 (ja) * | 1992-05-28 | 2000-10-23 | 日本バイエルアグロケム株式会社 | １−（３，４−ジ置換フェニル）テトラゾリノン誘導体、その製造法および除草剤としての用途 |
| JP3102952B2 (ja) * | 1992-05-28 | 2000-10-23 | 日本バイエルアグロケム株式会社 | 除草性１−（３−ハロ−４−トリフルオロメチルフェニル）テトラゾリノン誘導体 |
| JP3102954B2 (ja) * | 1992-06-03 | 2000-10-23 | 日本バイエルアグロケム株式会社 | 除草性１−（３−ハロ−４−置換フェニル）テトラゾリノン誘導体 |
| JP3505195B2 (ja) * | 1992-07-09 | 2004-03-08 | バイエルクロップサイエンス株式会社 | テトラゾリノン類の水田用除草剤としての利用 |
| JP2822143B2 (ja) * | 1993-02-25 | 1998-11-11 | 日本バイエルアグロケム株式会社 | テトラゾリノン類の水田用除草剤としての利用 |
-
1993
- 1993-09-30 JP JP26541793A patent/JP3390499B2/ja not_active Expired - Fee Related
-
1994
- 1994-09-01 TW TW083108036A patent/TW245715B/zh not_active IP Right Cessation
- 1994-09-19 ES ES94114714T patent/ES2116496T3/es not_active Expired - Lifetime
- 1994-09-19 EP EP94114714A patent/EP0646577B1/en not_active Expired - Lifetime
- 1994-09-19 DE DE69410722T patent/DE69410722T2/de not_active Expired - Fee Related
- 1994-09-23 US US08/311,643 patent/US5767286A/en not_active Expired - Fee Related
- 1994-09-26 KR KR1019940024213A patent/KR100345045B1/ko not_active Expired - Fee Related
- 1994-09-29 HU HU9402794A patent/HU216275B/hu not_active IP Right Cessation
- 1994-09-29 BR BR9403944A patent/BR9403944A/pt not_active IP Right Cessation
- 1994-09-30 CN CN94116998A patent/CN1052478C/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4618365A (en) * | 1983-12-09 | 1986-10-21 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones and their use as herbicides |
| EP0202929A2 (en) * | 1985-05-23 | 1986-11-26 | UNIROYAL CHEMICAL COMPANY, Inc. | Substituted tetrazolinones |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1102183A (zh) | 1995-05-03 |
| TW245715B (enExample) | 1995-04-21 |
| ES2116496T3 (es) | 1998-07-16 |
| KR100345045B1 (ko) | 2002-11-13 |
| JP3390499B2 (ja) | 2003-03-24 |
| EP0646577A1 (en) | 1995-04-05 |
| EP0646577B1 (en) | 1998-06-03 |
| DE69410722T2 (de) | 1998-10-01 |
| KR950008492A (ko) | 1995-04-17 |
| JPH07118246A (ja) | 1995-05-09 |
| US5767286A (en) | 1998-06-16 |
| BR9403944A (pt) | 1995-06-13 |
| HU9402794D0 (en) | 1994-12-28 |
| HUT69063A (en) | 1995-08-28 |
| DE69410722D1 (de) | 1998-07-09 |
| HU216275B (hu) | 1999-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1052478C (zh) | 1,4-二取代-5(4h)-四唑啉酮类的制备方法 | |
| CN1025981C (zh) | 除草剂组合物 | |
| CN1062726A (zh) | N-甲酰苯胺类杀节肢动物剂 | |
| CN1137103C (zh) | 制备三唑啉硫酮衍生物的方法 | |
| CN1347406A (zh) | 氨基甲酸衍生物及其作为促代谢谷氨酸受体配基的用途 | |
| CN1527812A (zh) | 具有除草活性的新的取代的苯胺衍生物 | |
| CN101080391A (zh) | 2－吡啶基乙基羧酰胺衍生物的制备方法 | |
| CN1819986A (zh) | 1,3－二苯基丙－2－烯－1－酮衍生物的制备 | |
| CN87104319A (zh) | 苯并吡喃衍生物 | |
| CN1344259A (zh) | 用于制备1,3－噁嗪－6－酮和尿嘧啶的方法以及中间体 | |
| CN101080390A (zh) | 2－乙基氨基吡啶衍生物的制备方法 | |
| CN1162405C (zh) | 取代的苯甲酰基酮,它们的制备方法和作为除草剂的用途 | |
| CN1280278C (zh) | 不对称的4,6－双(芳氧基)嘧啶衍生物的制备方法 | |
| CN1639096A (zh) | 反式－4－氨基－1－环己烷羧酸衍生物的制备方法 | |
| CN1221504C (zh) | 全氟异丙基苯衍生物 | |
| CN87107226A (zh) | 内酰胺衍生物及其制备 | |
| CN100338047C (zh) | 吡唑并嘧啶酮类的制备方法 | |
| CN1074765C (zh) | 制备3－(1－羟苯基－1－烷氧亚氨基甲基)二噁嗪的方法 | |
| CN1094713A (zh) | N-取代的苯基氨基甲酸衍生物及其制法和农业和园艺用杀菌剂 | |
| CN86102857A (zh) | 植物生长调节剂取代噻唑烷酮的制备方法 | |
| CN1028863C (zh) | 3-环烷基-丙-2-烯酰胺衍生物 | |
| CN88103413A (zh) | 吡喃化合物 | |
| CN1068822A (zh) | 取代的苯并噻唑衍生物，其制备和作为除草剂的应用 | |
| CN1104215A (zh) | 4-氰基苯基亚氨基杂环化合物 | |
| CN88102858A (zh) | 可用作抗高血压剂的肼衍生物的制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |