CA2312703A1 - Derives de 3-(benzazol-4-yle)dione de pyrimidine herbicides - Google Patents
Derives de 3-(benzazol-4-yle)dione de pyrimidine herbicides Download PDFInfo
- Publication number
- CA2312703A1 CA2312703A1 CA002312703A CA2312703A CA2312703A1 CA 2312703 A1 CA2312703 A1 CA 2312703A1 CA 002312703 A CA002312703 A CA 002312703A CA 2312703 A CA2312703 A CA 2312703A CA 2312703 A1 CA2312703 A1 CA 2312703A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- butyl
- carbonyl
- ethyl
- halogen
- 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.)
- Abandoned
Links
- 239000004009 herbicide Substances 0.000 title claims description 10
- -1 1,3-propylene- Chemical class 0.000 claims abstract description 915
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 47
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 46
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 40
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
- 150000002367 halogens Chemical class 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 55
- 230000008569 process Effects 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- 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 claims description 24
- 239000000460 chlorine Chemical group 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 229910052801 chlorine Chemical group 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 239000011737 fluorine Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 162
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 83
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 62
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 58
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 43
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000002585 base Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- 101150041968 CDC13 gene Proteins 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- 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
- 239000004480 active ingredient Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 125000005499 phosphonyl group Chemical group 0.000 description 21
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 18
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- 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
- 239000003085 diluting agent Substances 0.000 description 15
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 235000011167 hydrochloric acid Nutrition 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000002798 polar solvent Substances 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 10
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 150000004292 cyclic ethers Chemical class 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 150000002431 hydrogen Chemical group 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
- 229910017604 nitric acid Inorganic materials 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 150000001448 anilines Chemical class 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000004649 carbonic acid derivatives 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
- 239000012141 concentrate Substances 0.000 description 6
- 238000003379 elimination reaction Methods 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
- 150000008282 halocarbons Chemical class 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
- 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
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 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 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000006396 nitration reaction Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 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
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 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
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
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- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 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
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 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
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 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
- 150000008512 pyrimidinediones Chemical class 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
- 239000012266 salt solution Substances 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
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000012546 transfer Methods 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
- 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)
Abstract
L'invention concerne des dérivés 3-(benzazol-4-yle)dione de pyrimidine de la formule (I) et leurs sels. Dans cette formule, X = O, S; R?1¿ = H, NH¿2?, alkyle C¿1?-C¿6?, halogénure d'alkyle C¿1?-C¿6?; R?2¿ = H, halogène, alkyle C¿1?-C¿6?, halogénure d'alkyle, alkylthio C¿1?-C¿6?, alkylsulfinyle C¿1?-C¿6?, alkylsulfonyle C¿1?-C¿6?; R?3¿ = H, halogène, alkyle C¿1?-C¿6?; R?4¿ = H, halogène; R?5¿ = CN, halogène, alkyle C¿1?-C¿6?, halogénure d'alkyle C¿1?-C¿6?, alcoxy C¿1?-C¿6?, halogénure d'alcoxy C¿1?-C¿6?; =Y- = un groupe =N-N(R?6¿)-, =C(ZR?7¿)-N(R?6¿)-, =C(ZR?7¿)-O-, =C(ZR?7¿)-S-; R?6¿ = alkyle C¿1?-C¿6?, halogénure d'alkyle C¿1?-C¿4?, cycloalkyle C¿3?-C¿6?, alkényle C¿3?-C¿6?, alkinyle C¿3?-C¿6?, alkyle C¿1?-C¿6?-SO¿2?, alkyle C¿1?-C¿6?-CO, halogénure d'alkyle C¿1?-C¿6?-CO, alkyle C¿1?-C¿6?-CS, alcoxy C¿1?-C¿6?-CO, alcoxy C¿1?-C¿6?-CS ou alkyle C¿1?-C¿6? éventuellement substitué; Z = liaison chimique, O, S, -S(O)-, -SO¿2?-, -NH-, -N(R?8¿)-; R?7¿, R?8¿ = alkyle C¿1?-C¿6?, halogénure d'alkyle C¿1?-C¿6?, hydroxy-alkyle C¿1?-C¿4?, cyano-alkyle C¿1?-C¿4?, alcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?, halogénure d'alcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkényloxy C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkinyloxy C¿3?-C¿4?-alkyle C¿1?-C¿4?, cycloalkoxy C¿3?-C¿8?-alkyle C¿1?-C¿4?, amino-alkyle C¿1?-C¿4?, alkylamino C¿1?-C¿4?-alkyle C¿1?-C¿4?, di(alkyle C¿1?-C¿4?)amino-alkyle C¿1?-C¿4?, alkylthio C¿1?-C¿4?-alkyle C¿1?-C¿4?, halogénure d'alkylthio C¿1?-C¿4?, alkénylthio C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkinylthio C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkylsulfinyle C¿1?-C¿4?-alkyle C¿1?-C¿4?, halogénure d'alkylsulfinyle C¿1?-C¿4?-alkyle C¿1?-C¿4?-alkénylsulfinyle C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkinylsulfinyle C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkylsulfonyle C¿1?-C¿4?-alkyle C¿1?-C¿4?, halogénure d'alkylsulfonyle C¿1?-C¿4?-alkyle C¿1?-C¿4?, alkénylsulfonyle C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkinylsulfonyle C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkényle C¿3?-C¿6?, cyano-alkényle C¿3?-C¿6?, halogénure d'alkényle C¿3?-C¿6?, alkinyle C¿3?-C¿6?, cyano-alkinyle C¿3?-C¿6?, halogénure d'alkinyle C¿3?-C¿6?, HO-CO-alkyle C¿1?-C¿4?, (alcoxy C¿1?-C¿4?)CO-alkyle C¿1?-C¿4?, (alkyle C¿1?-C¿4?)CS-alkyle C¿1?-C¿4?, H¿2?N-CO-alkyle C¿1?-C¿4?, alkyle C¿1?-C¿4?-NHCO-alkyle C¿1?-C¿4?, di(alkyle C¿1?-C¿4?)NCO-alkyle C¿1?-C¿4?, di(alkyle C¿1?-C¿4?)phosphonyle-alkyle C¿1?-C¿4?, cycloalkyle C¿3?-C¿8? éventuellement substitué, cycloalkyle C¿3?-C¿8?-alkyle C¿1?-C¿4?, phényle, phényle-alkyle C¿1?-C¿4?, hétérocyclyle ayant entre 3 et 7 chaînons ou hétérocyclyle-alkyle C¿1?-C¿4?, chaque composé hétérocyclyle pouvant contenir un chaînon cyclique CS, ou si Z = liaison chimique, R?7¿ désigne également H, OH, CN, SH, NH¿2?, halogène, -CH(OH)-CH¿2?-R?9¿, -CH(halogène)-R?9¿, R?9¿ = COOH, (alcoxy C¿1?-C¿4?)carbonyle, (alkylthio C¿1?-C¿4?)carbonyle, CONH¿2?, alkyle C¿1?-C¿4?-NHCO ou di(alkyle C¿1?-C¿4?)NCO, ou R?7¿ + R?8¿ = chaîne de 1,3-propylène-tétraméthylène, de pentaméthylène ou d'oxyéthylène d'éthylène, éventuellement substituée.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19755926.3 | 1997-12-17 | ||
| DE19755926A DE19755926A1 (de) | 1997-12-17 | 1997-12-17 | Herbizide 3-(Benzazol-4-yl)pyrimidindion-Derivate |
| PCT/EP1998/008098 WO1999031091A1 (fr) | 1997-12-17 | 1998-12-11 | Derives de 3-(benzazol-4-yle)dione de pyrimidine herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2312703A1 true CA2312703A1 (fr) | 1999-06-24 |
Family
ID=7852130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002312703A Abandoned CA2312703A1 (fr) | 1997-12-17 | 1998-12-11 | Derives de 3-(benzazol-4-yle)dione de pyrimidine herbicides |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1047693A1 (fr) |
| JP (1) | JP2002508369A (fr) |
| KR (1) | KR20010033195A (fr) |
| CN (1) | CN1282331A (fr) |
| AR (1) | AR017885A1 (fr) |
| AU (1) | AU1878599A (fr) |
| BG (1) | BG104546A (fr) |
| BR (1) | BR9813613A (fr) |
| CA (1) | CA2312703A1 (fr) |
| DE (1) | DE19755926A1 (fr) |
| IL (1) | IL136309A0 (fr) |
| PL (1) | PL341306A1 (fr) |
| SK (1) | SK7502000A3 (fr) |
| WO (1) | WO1999031091A1 (fr) |
| ZA (1) | ZA9811490B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8124818B2 (en) | 2004-07-22 | 2012-02-28 | Basf Aktiengesellschaft | Method for the production of 3-phenyl(thio) uracils and dithiouracils |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1195753C (zh) | 1998-09-09 | 2005-04-06 | 石原产业株式会社 | 用作除草剂的稠合的苯衍生物 |
| EP1131319B1 (fr) * | 1998-11-16 | 2003-09-03 | Basf Aktiengesellschaft | 3- benz(ox/thi)azol-7-yl]-1h-pyrimidin-2,4-diones |
| DE19937772A1 (de) * | 1999-08-10 | 2001-02-15 | Bayer Ag | Substituierte Heterocyclyl-2GH-chromene |
| DE50001813D1 (de) * | 1999-08-12 | 2003-05-22 | Basf Ag | Substituierte benzoxazole |
| US20020111274A1 (en) * | 2000-07-15 | 2002-08-15 | Basf Aktiengesellschaft | 1-alkyl-3-[1-(substituted phenyl) benzotriazol-6-yl] uracils |
| US7153583B2 (en) | 2003-05-07 | 2006-12-26 | Shin-Etsu Chemical Co., Ltd. | Liquid silicone rubber coating composition and airbag |
| 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 |
| DK2499136T3 (en) | 2009-11-13 | 2014-03-03 | Basf Se | 3- (3,4-dihydro-2H-benzo [1,4] oxazin-6-yl) -1H-pyrimidine-2,4-dione COMPOUNDS AS HERBICIDES |
| 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 |
| CN114249710A (zh) | 2016-05-24 | 2022-03-29 | 巴斯夫欧洲公司 | 除草的尿嘧啶吡啶类 |
| WO2023205281A1 (fr) * | 2022-04-20 | 2023-10-26 | Siemens Healthcare Diagnostics Inc. | Quantification de composés d'éthoxylate d'alkylphénol dans des échantillons aqueux |
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| 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 |
| EP0853620A1 (fr) * | 1995-10-04 | 1998-07-22 | Fmc Corporation | Benzisoxazoles et benzisoxazolidinones heterocycliques herbicides |
| 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 |
| JP2001511140A (ja) * | 1997-02-04 | 2001-08-07 | ビーエーエスエフ アクチェンゲゼルシャフト | ２−（２，４（１ｈ，３ｈ）−ピリミジンジオン−３−イル）ベンゾチアゾールの置換体 |
| 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 WO PCT/EP1998/008098 patent/WO1999031091A1/fr not_active Application Discontinuation
- 1998-12-11 AU AU18785/99A patent/AU1878599A/en not_active Abandoned
- 1998-12-11 CA CA002312703A patent/CA2312703A1/fr not_active Abandoned
- 1998-12-11 JP JP2000539015A patent/JP2002508369A/ja not_active Withdrawn
- 1998-12-11 SK SK750-2000A patent/SK7502000A3/sk unknown
- 1998-12-11 PL PL98341306A patent/PL341306A1/xx unknown
- 1998-12-11 BR BR9813613-5A patent/BR9813613A/pt not_active Application Discontinuation
- 1998-12-11 EP EP98963564A patent/EP1047693A1/fr not_active Withdrawn
- 1998-12-11 KR KR1020007006580A patent/KR20010033195A/ko not_active Application Discontinuation
- 1998-12-11 CN CN98812332A patent/CN1282331A/zh active Pending
- 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 |
|---|---|---|---|---|
| US8124818B2 (en) | 2004-07-22 | 2012-02-28 | Basf Aktiengesellschaft | Method for the production of 3-phenyl(thio) uracils and dithiouracils |
| US8252925B2 (en) | 2004-07-22 | 2012-08-28 | Basf Aktiengesellschaft | Method for the production of 3-phenyl(thio)uracils and dithiouracils |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010033195A (ko) | 2001-04-25 |
| AR017885A1 (es) | 2001-10-24 |
| AU1878599A (en) | 1999-07-05 |
| PL341306A1 (en) | 2001-04-09 |
| ZA9811490B (en) | 2000-06-15 |
| IL136309A0 (en) | 2001-05-20 |
| JP2002508369A (ja) | 2002-03-19 |
| SK7502000A3 (en) | 2001-01-18 |
| EP1047693A1 (fr) | 2000-11-02 |
| CN1282331A (zh) | 2001-01-31 |
| BR9813613A (pt) | 2000-10-10 |
| BG104546A (en) | 2001-08-31 |
| WO1999031091A1 (fr) | 1999-06-24 |
| DE19755926A1 (de) | 1999-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |