DE19755926A1 - Herbizide 3-(Benzazol-4-yl)pyrimidindion-Derivate - Google Patents
Herbizide 3-(Benzazol-4-yl)pyrimidindion-DerivateInfo
- Publication number
- DE19755926A1 DE19755926A1 DE19755926A DE19755926A DE19755926A1 DE 19755926 A1 DE19755926 A1 DE 19755926A1 DE 19755926 A DE19755926 A DE 19755926A DE 19755926 A DE19755926 A DE 19755926A DE 19755926 A1 DE19755926 A1 DE 19755926A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- carbonyl
- butyl
- ethyl
- methyl
- 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.)
- Withdrawn
Links
- BTRZCXUPKJCHIB-UHFFFAOYSA-N 3-(1h-indol-4-yl)-1h-pyrimidine-2,4-dione Chemical class O=C1C=CNC(=O)N1C1=CC=CC2=C1C=CN2 BTRZCXUPKJCHIB-UHFFFAOYSA-N 0.000 title claims description 25
- 230000002363 herbicidal effect Effects 0.000 title claims description 15
- -1 1,3-propylene- Chemical class 0.000 claims abstract description 881
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 47
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
- 150000002367 halogens Chemical class 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 52
- 239000000460 chlorine Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- 150000001448 anilines Chemical class 0.000 claims description 11
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 11
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 10
- 239000004009 herbicide Substances 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 81
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 60
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 56
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 21
- 125000005499 phosphonyl group Chemical group 0.000 description 21
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 235000019441 ethanol Nutrition 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 16
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 12
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 150000004292 cyclic ethers Chemical class 0.000 description 11
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 150000001340 alkali metals Chemical class 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 229960004756 ethanol Drugs 0.000 description 9
- 235000011167 hydrochloric acid Nutrition 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000002798 polar solvent Substances 0.000 description 9
- 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 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 229960001701 chloroform Drugs 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000000802 nitrating effect Effects 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WLOOYFSUYWVINT-UHFFFAOYSA-N 3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=C(N)C(O)=C(Cl)C=C1F WLOOYFSUYWVINT-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004324 thiepan-2-yl group Chemical group [H]C1([H])SC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004275 thietan-2-yl group Chemical group [H]C1([H])SC([H])(*)C1([H])[H] 0.000 description 1
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 239000012749 thinning agent Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19755926A DE19755926A1 (de) | 1997-12-17 | 1997-12-17 | Herbizide 3-(Benzazol-4-yl)pyrimidindion-Derivate |
IL13630998A IL136309A0 (en) | 1997-12-17 | 1998-11-12 | Herbicidal 3-(benzazol-4-yl) pyrimidine-dione derivatives |
JP2000539015A JP2002508369A (ja) | 1997-12-17 | 1998-12-11 | 除草剤3−(ベンゾアゾール−4−イル)ピリミジンジオン誘導体 |
PCT/EP1998/008098 WO1999031091A1 (de) | 1997-12-17 | 1998-12-11 | Herbizide 3-(benzazol-4-yl)pyrimidindion-derivate |
BR9813613-5A BR9813613A (pt) | 1997-12-17 | 1998-12-11 | Derivado 3-(benzazol-4-il) pirimidinadiona, uso de um derivado i de 3-(benzazol-4-il) pirimidinadiona ou um sal agriculturalmente útil do mesmo, composição herbicida, processos para a preparação de composições herbicidamente ativas e de controle de vegetação indispensável, ariluréia, arilanilida, e, 2-aminofenol substituìdo, -tiofenol ou -anilina |
CA002312703A CA2312703A1 (en) | 1997-12-17 | 1998-12-11 | Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives |
KR1020007006580A KR20010033195A (ko) | 1997-12-17 | 1998-12-11 | 제초제 3-(벤즈아졸-4-일)피리미딘디온 유도체 |
EP98963564A EP1047693A1 (de) | 1997-12-17 | 1998-12-11 | Herbizide 3-(benzazol-4-yl)pyrimidindion-derivate |
PL98341306A PL341306A1 (en) | 1997-12-17 | 1998-12-11 | Herbicidal derivatives of 3-(benzazol-4-lyl) pyrimidinone |
SK750-2000A SK7502000A3 (en) | 1997-12-17 | 1998-12-11 | Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives |
CN98812332A CN1282331A (zh) | 1997-12-17 | 1998-12-11 | 除草的3-(吲哚-4-基)嘧啶二酮衍生物 |
AU18785/99A AU1878599A (en) | 1997-12-17 | 1998-12-11 | Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives |
ZA9811490A ZA9811490B (en) | 1997-12-17 | 1998-12-15 | Herbicidal 3-(benzazol-4-yl)pyrimidinedione derivatives. |
ARP980106442A AR017885A1 (es) | 1997-12-17 | 1998-12-17 | Derivados de 3-(benzazol-4-il)pirimidindiona, herbicidas preparados con dichos derivados, procedimiento para controlar el crecimiento de plantasindeseables, mediante la aplicacion de dichos herbicidas y compuestos intermediarios utilizables en la preparacion de dichos derivados. |
BG104546A BG104546A (en) | 1997-12-17 | 2000-06-19 | Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19755926A DE19755926A1 (de) | 1997-12-17 | 1997-12-17 | Herbizide 3-(Benzazol-4-yl)pyrimidindion-Derivate |
Publications (1)
Publication Number | Publication Date |
---|---|
DE19755926A1 true DE19755926A1 (de) | 1999-06-24 |
Family
ID=7852130
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19755926A Withdrawn DE19755926A1 (de) | 1997-12-17 | 1997-12-17 | Herbizide 3-(Benzazol-4-yl)pyrimidindion-Derivate |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP1047693A1 (zh) |
JP (1) | JP2002508369A (zh) |
KR (1) | KR20010033195A (zh) |
CN (1) | CN1282331A (zh) |
AR (1) | AR017885A1 (zh) |
AU (1) | AU1878599A (zh) |
BG (1) | BG104546A (zh) |
BR (1) | BR9813613A (zh) |
CA (1) | CA2312703A1 (zh) |
DE (1) | DE19755926A1 (zh) |
IL (1) | IL136309A0 (zh) |
PL (1) | PL341306A1 (zh) |
SK (1) | SK7502000A3 (zh) |
WO (1) | WO1999031091A1 (zh) |
ZA (1) | ZA9811490B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002006219A2 (en) * | 2000-07-15 | 2002-01-24 | Basf Aktiengesellschaft | 1-alkyl-3-[1-(substituted phenyl) benzotriazol-6-yl] uracils |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU6018799A (en) | 1998-09-09 | 2000-03-27 | Ishihara Sangyo Kaisha Ltd. | Fused-benzene derivatives useful as herbicides |
JP2002529481A (ja) * | 1998-11-16 | 2002-09-10 | ビーエーエスエフ アクチェンゲゼルシャフト | 除草剤3−[ベンゾ(オキサ/チア)ゾール−7−イル]−1h−ピリミジン−2,4−ジオン類 |
DE19937772A1 (de) * | 1999-08-10 | 2001-02-15 | Bayer Ag | Substituierte Heterocyclyl-2GH-chromene |
AU6994600A (en) * | 1999-08-12 | 2001-03-13 | Basf Aktiengesellschaft | Substituted benzoxazoles |
US7153583B2 (en) | 2003-05-07 | 2006-12-26 | Shin-Etsu Chemical Co., Ltd. | Liquid silicone rubber coating composition and airbag |
AU2005266622B8 (en) | 2004-07-22 | 2011-05-19 | Basf Aktiengesellschaft | Method for the production of 3-phenyl(thio)uracils and dithiouracils |
CN100398523C (zh) * | 2005-06-13 | 2008-07-02 | 上海师范大学 | 2,4-二氯苯氧乙酰胺嘧啶衍生物及其制备方法和农药组合物 |
MX2012005501A (es) | 2009-11-13 | 2012-07-10 | Basf Se | Compuestos 3- (3, 4- dihidro-2h-benzo [1, 4] -oxazin-6-il)-1h-piri midin-2, 4-diona como herbicidas. |
CN105294671B (zh) * | 2014-06-10 | 2018-03-20 | 华中师范大学 | 一种嘧啶二酮类化合物及其应用 |
CR20180596A (es) | 2016-05-24 | 2019-04-09 | Basf Se | Uracilpiridinas herbicidas |
WO2023205281A1 (en) * | 2022-04-20 | 2023-10-26 | Siemens Healthcare Diagnostics Inc. | Quantitation of alkylphenol ethoxylate compounds in aqueous samples |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE795549A (fr) * | 1972-02-18 | 1973-08-16 | Bayer Ag | Nouveaux 1-aminouraciles et leurs sels, leur procede de preparation et leur application comme herbicides |
JPH05262765A (ja) * | 1992-03-18 | 1993-10-12 | Sumitomo Chem Co Ltd | ベンゾフラン誘導体およびそれを有効成分とする除草剤 |
DE4329096A1 (de) * | 1993-08-30 | 1995-03-02 | Bayer Ag | Heterocyclylbenzoheterocyclen |
US5753595A (en) * | 1995-08-31 | 1998-05-19 | Fmc Corporation | Herbicidal 3-(substituted benzoxazol-7-yl) and 3-(Substituted benzothiazol-7-yl)-1-substituted-6-trifluoromethyl-2 4-(1h 3h)pyrimidinediones |
DE19532048A1 (de) * | 1995-08-31 | 1997-03-06 | Basf Ag | Substituierte Benzthiazole als Pflanzenschutzmittel |
CN1198745A (zh) * | 1995-10-04 | 1998-11-11 | Fmc有限公司 | 苯并异噁唑和苯并异噁唑烷酮杂环除草剂 |
WO1997042188A1 (fr) * | 1996-05-08 | 1997-11-13 | Kumiai Chemical Industry Co., Ltd. | Derives d'uracile a substitution indolyle et herbicides contenant ces derives en tant qu'ingredients actifs |
CA2279644A1 (en) * | 1997-02-04 | 1998-08-06 | Basf Aktiengesellschaft | Substituted 2-(2,4(1h,3h)-pyrimidindion-3-yl) benzthiazoles |
US6077812A (en) * | 1997-02-26 | 2000-06-20 | Fmc Corporation | Cycloimido-substituted benzofused heterocyclic herbicides |
-
1997
- 1997-12-17 DE DE19755926A patent/DE19755926A1/de not_active Withdrawn
-
1998
- 1998-11-12 IL IL13630998A patent/IL136309A0/xx unknown
- 1998-12-11 AU AU18785/99A patent/AU1878599A/en not_active Abandoned
- 1998-12-11 BR BR9813613-5A patent/BR9813613A/pt not_active Application Discontinuation
- 1998-12-11 JP JP2000539015A patent/JP2002508369A/ja not_active Withdrawn
- 1998-12-11 EP EP98963564A patent/EP1047693A1/de not_active Withdrawn
- 1998-12-11 WO PCT/EP1998/008098 patent/WO1999031091A1/de not_active Application Discontinuation
- 1998-12-11 CN CN98812332A patent/CN1282331A/zh active Pending
- 1998-12-11 CA CA002312703A patent/CA2312703A1/en not_active Abandoned
- 1998-12-11 PL PL98341306A patent/PL341306A1/xx unknown
- 1998-12-11 KR KR1020007006580A patent/KR20010033195A/ko not_active Application Discontinuation
- 1998-12-11 SK SK750-2000A patent/SK7502000A3/sk unknown
- 1998-12-15 ZA ZA9811490A patent/ZA9811490B/xx unknown
- 1998-12-17 AR ARP980106442A patent/AR017885A1/es unknown
-
2000
- 2000-06-19 BG BG104546A patent/BG104546A/xx unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002006219A2 (en) * | 2000-07-15 | 2002-01-24 | Basf Aktiengesellschaft | 1-alkyl-3-[1-(substituted phenyl) benzotriazol-6-yl] uracils |
WO2002006219A3 (en) * | 2000-07-15 | 2004-02-19 | Basf Ag | 1-alkyl-3-[1-(substituted phenyl) benzotriazol-6-yl] uracils |
Also Published As
Publication number | Publication date |
---|---|
PL341306A1 (en) | 2001-04-09 |
JP2002508369A (ja) | 2002-03-19 |
BR9813613A (pt) | 2000-10-10 |
CN1282331A (zh) | 2001-01-31 |
ZA9811490B (en) | 2000-06-15 |
BG104546A (en) | 2001-08-31 |
AU1878599A (en) | 1999-07-05 |
AR017885A1 (es) | 2001-10-24 |
CA2312703A1 (en) | 1999-06-24 |
SK7502000A3 (en) | 2001-01-18 |
KR20010033195A (ko) | 2001-04-25 |
IL136309A0 (en) | 2001-05-20 |
WO1999031091A1 (de) | 1999-06-24 |
EP1047693A1 (de) | 2000-11-02 |
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