CN1330649A - 3-[苯并(噁/噻)唑-7-基]-1h-嘧啶-2,4-二酮化合物 - Google Patents
3-[苯并(噁/噻)唑-7-基]-1h-嘧啶-2,4-二酮化合物 Download PDFInfo
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- CN1330649A CN1330649A CN99814526A CN99814526A CN1330649A CN 1330649 A CN1330649 A CN 1330649A CN 99814526 A CN99814526 A CN 99814526A CN 99814526 A CN99814526 A CN 99814526A CN 1330649 A CN1330649 A CN 1330649A
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- Prior art keywords
- alkyl
- base
- hydrogen
- oxygen
- pyrimidine
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- 125000005605 benzo group Chemical group 0.000 title claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
- 239000001301 oxygen Substances 0.000 claims abstract description 34
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 3
- -1 nitro, amino, hydroxyl Chemical group 0.000 claims description 87
- 239000000203 mixture Substances 0.000 claims description 61
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 27
- 229930192474 thiophene Natural products 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 11
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- 230000001473 noxious effect Effects 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 abstract 1
- 239000002585 base Substances 0.000 description 130
- 150000001875 compounds Chemical class 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 208000032826 Ring chromosome 3 syndrome Diseases 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 208000002991 Ring chromosome 4 syndrome Diseases 0.000 description 7
- 238000005576 amination reaction Methods 0.000 description 7
- 235000013877 carbamide Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 229960001777 castor oil Drugs 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 238000001816 cooling 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
- 238000009333 weeding Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 239000003337 fertilizer Substances 0.000 description 4
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- 230000012010 growth Effects 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
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- 125000000217 alkyl group Chemical group 0.000 description 3
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
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- 235000010469 Glycine max Nutrition 0.000 description 2
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- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- 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
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- 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
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- C07C271/54—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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Abstract
本发明涉及具有除草活性的式(Ⅰ)3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮及其农业上可用的盐,其中:X=氧或硫;Y=为氧或硫;Z=化学键,C1-4-亚烷基,0,S,SO,SO2;R1=氢,NH2,C1-C6-烷基,C1-C6-卤代烷基;R2=氢,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷硫基,C1-C6-烷基亚磺酰基或C1-C6-烷磺酰基;R3=氢,卤素,C1-C6-烷基;R4=氢,卤素;R5=CN,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基或C1-C6-卤代烷氧基;R6=氢,C3-C7-环烷基,包含1个或多个氧和/或硫原子的3-7元饱和杂环基,其中每个环烷基或每个杂环基环均可以含有羰基或硫代羰基环组成部分。
Description
本发明涉及式I的3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物及其农业上可用的盐:其中:X 为氧或硫;Y 为氧或硫;Z 为化学键,C1-4-亚烷基,氧,硫,SO或SO2;R1 为氢,氨基,C1-C6-烷基或C1-C6-卤代烷基;R2 为氢,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷硫基,C1-C6-烷基亚磺酰基或C1-C6-烷磺酰基;R3 为氢,卤素或C1-C6-烷基;R4 为氢或卤素;R5 为氰基,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基或C1-C6-卤代烷氧基;R6 为氢,C3-C7-环烷基或包含1个或多个氧和/或硫原子的3-7元饱和杂环基,其中每个环烷基或每个杂环基环均可以含有羰基或硫代羰基环组成部分,并且其中的每一环烷基和杂环基环均可以是未取代的,或者可以带有1-4个独立选自如下的取代基:氰基,硝基,氨基,羟基,卤素,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-氰基烷基,C1-C4-羟基烷基,C1-C4-氨基烷基,C1-C4-烷氧基,C1-C4-卤代烷氧基,C1-C4-烷硫基,C1-C4-卤代烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷基磺酰基,C1-C4-卤代烷基磺酰基,(C1-C4-烷氧基)羰基,(C1-C4-烷基)羰基,(C1-C4-卤代烷基)羰基,(C1-C4-烷基)羰氧基,(C1-C4-卤代烷基)羰氧基,二(C1-C4-烷基)氨基,C3-C6-链烯基,C3-C6-炔基,C3-C4-链烯氧基,C3-C4-链烯硫基,C3-C4-炔氧基和C3-C4-炔硫基,条件是当Y为氧且Z为化学键时,R6只能为氢,以及当Y为硫时,R6不能为C3-C6-环烷基。
WO97/08170描述了一些用作除草剂的3-(苯并(噁/噻)唑-7-基)-6-(三氟甲基)尿嘧啶化合物。WO97/08171中描述了另外一些3-(苯并噻唑-7-基)尿嘧啶化合物,它们用作除草剂并用于植物的干燥/落叶。特别是WO97/12886提供了一些据说具有除草和干燥剂作用的3-苯并异噁唑-7-基-2,4-(1H,3H)嘧啶二酮化合物。
本发明的目的是提供一类具有除草活性的新型尿嘧啶化合物。较之已知的尿嘧啶化合物,它们对有害植物的防治具有更好的针对性。
我们已经发现,这一目的可由本发明的式I3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮类化合物实现。
而且,我们进一步发现了包含式I化合物并且具有十分优良除草活性的除草组合物。另外,我们也发现了制备这些组合物的方法以及应用化合物I防治有害植物的方法。
根据取代方式,式I化合物可以含有一个或多个手性中心。在这种情况下它们以对映体或非对映体混合物形式存在。本发明不仅提供了纯对映体或非对映体,而且还提供了它们的混合物。
适宜的农业上可用的盐特别为这样一些阳离子的盐,或这样一些酸的酸加成盐,即它们的阳离子或阴离子各自不会对化合物I的除草活性产生不利影响。因此,合适的阳离子尤其为碱金属(优选钠和钾)离子,碱土金属(优选钙、镁和钡)离子,和过渡金属(优选锰、铜、锌和铁)离子,以及铵离子,并且如果需要的话,所述铵离子可带有1-4个C1-C4-烷基取代基和/或一个苯基或苄基取代基(优选二异丙基铵、四甲铵、四丁铵、三甲基苄基铵离子);此外,还可以为磷鎓离子,锍离子[优选三(C1-C4-烷基)锍离子]和氧化锍离子[优选三(C1-C4-烷基)氧化锍离子]。
适用的酸加成盐的阴离子主要为氯、溴、氟离子,硫酸氢根,硫酸根,磷酸二氢根,磷酸氢根,磷酸根,硝酸根,碳酸氢根,碳酸根,六氟硅酸根,六氟磷酸根,苯甲酸根以及C1-C4-链烷酸的阴离子,优选甲酸根,乙酸根,丙酸根和丁酸根。它们可通过I与相应阴离子的酸反应生成,所述酸优选盐酸、氢溴酸、硫酸、磷酸或硝酸。
取代基R1、R2、R3、R5和R6的定义中所述的或作为位于饱和环烷基或饱和杂环上基团的有机基团-如术语卤素-是单独列举的具体基团成员的集合术语。所有烃链,即所有的烷基、卤代烷基、氰基烷基、羟基烷基、氨基烷基、烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、链烯基、链烯氧基、链烯硫基、炔基、炔氧基和炔硫基部分均可以是直链或支链的。卤代取代基优选带有1-5个相同或不同的卤原子,在每种情况下卤素均表示氟、氯、溴或碘。
其它术语的实例包括:- C1-C4-烷基:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基;- C1-C4-亚烷基:亚甲基、1,2-亚乙基、1,1-亚乙基、1,3-亚丙基、1,2-亚丙基、2,2-亚丙基、1,4-亚丁基或2,3-亚丁基;- C1-C4-卤代烷基:部分或全部被氟、氯、溴和/或碘取代的上述C1-C4-烷基,亦即,例如,CH2F、CHF2、CF3、CH2Cl、CH(Cl)2、C(Cl)3、氯氟甲基、二氯氟甲基、氯二氟甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、C2F5、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、CH2-C2F5、CF2-C2F5、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基或九氟丁基;- C1-C6-烷基:如上所述的C1-C4-烷基,或者,例如正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基,1-乙基-1-甲基丙基或1-乙基-2-甲基丙基,其中优选CH3,C2H5,CH2-C2H5,CH(CH3)2,正丁基,C(CH3)3,正戊基或正己基;- C1-C6-卤代烷基:部分或全部被氟、氯、溴和/或碘取代的上述C1-C6-烷基,亦即,例如上述C1-C4-卤代烷基中所述的任一基团,或5-氟-1-戊基,5-氯-1-戊基,5-溴-1-戊基,5-碘-1-戊基,5,5,5-三氯-1-戊基,十一氟戊基,6-氟-1-己基,6-氯-1-己基,6-溴-1-己基,6-碘-1-己基,6,6,6-三氯-1-己基或十二氟代己基;- 氰基-C1-C4-烷基:CH2CN,1-氰基乙基,2-氰基乙基,1-氰基丙-1-基,2-氰基丙-1-基,3-氰基丙-1-基,1-氰基丁-1-基,2-氰基丁-1-基,3-氰基丁-1-基,4-氰基丁-1-基,1-氰基丁-2-基,2-氰基丁-2-基,3-氰基丁-2-基,4-氰基丁-2-基,1-(CH2CN)乙-1-基,1-(CH2CN)-1-(CH3)乙-1-基或1-(CH2CN)丙-1-基;- 羟基C1-C4-烷基:CH2OH,1-羟基乙基,2-羟基乙基,1-羟基丙-1-基,2-羟基丙-1-基,3-羟基丙-1-基,1-羟基丁-1-基,2-羟基丁-1-基,3-羟基丁-1-基,4-羟基丁-1-基,1-羟基丁-2-基,2-羟基丁-2-基,3-羟基丁-2-基,4-羟基丁-2-基,1-(CH2OH)乙-1-基,1-(CH2OH)-1-(CH3)乙-1-基或1-(CH2OH)丙-1-基;- 氨基C1-C4-烷基:CH2NH2,1-氨基乙基,2-氨基乙基,1-氨基丙-1-基,2-氨基丙-1-基,3-氨基丙-1-基,1-氨基丁-1-基,2-氨基丁-1-基,3-氨基丁-1-基,4-氨基丁-1-基,1-氨基丁-2-基,2-氨基丁-2-基,3-氨基丁-2-基,4-氨基丁-2-基,1-(CH2NH2)乙-1-基,1-(CH2NH2)-1-(CH3)乙-1-基或1-(CH2NH2)丙-1-基;- C1-C4-烷氧基:OCH3、OC2H5、OCH2-C2H5、OCH(CH3)2、正丁氧基、OCH(CH3)-C2H5、OCH2-CH(CH3)2或C(CH3)3,优选OCH3、OC2H5或OCH(CH3)2。- C1-C4-卤代烷氧基:部分或全部由氟、氯、溴和/或碘取代的上述C1-C4-烷氧基,亦即,例如,OCH2F、OCHF2、OCF3、OCH2Cl、OCH(Cl)2、OC(Cl)3、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、2-氟乙氧基、2-氯乙氧基、2-溴乙氧基、2-碘乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、OC2F5、2-氟丙氧基、3-氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、2-氯丙氧基、3-氯丙氧基、2,3-二氯丙氧基、2-溴丙氧基、3-溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氯丙氧基、OCH2-C2F5、OCF2-C2F5、1-(CH2F)-2-氟乙氧基、1-(CH2Cl)-2-氯乙氧基、1-(CH2Br)-2-溴乙氧基、4-氟丁氧基、4-氯丁氧基、4-溴丁氧基或九氟丁氧基;优选OCHF2、OCF3、二氯氟甲氧基、氯二氟甲氧基或2,2,2-三氟乙氧基;- C1-C6-烷氧基:上述C1-C4-烷氧基,或者,例如正戊氧基,1-甲基丁氧基,2-甲基丁氧基,3-甲基丁氧基,2,2-二甲基丙氧基,1-乙基丙氧基,正己氧基,1,1-二甲基丙氧基,1,2-二甲基丙氧基,1-甲基戊氧基,2-甲基戊氧基,3-甲基戊氧基,4-甲基戊氧基,1,1-二甲基丁氧基,1,2-二甲基丁氧基,1,3-二甲基丁氧基,2,2-二甲基丁氧基,2,3-二甲基丁氧基,3,3-二甲基丁氧基,1-乙基丁氧基,2-乙基丁氧基,1,1,2-三甲基丙氧基,1,2,2-三甲基丙氧基,1-乙基-1-甲基丙氧基或1-乙基-2-甲基丙氧基,优选OCH3、OC2H5、OCH2-C2H5、OCH(CH3)2、正丁氧基、OC(CH3)3、正戊氧基或正己氧基;- C1-C6-卤代烷氧基:部分或全部被氟、氯、溴和/碘取代的上述C1-C6-烷氧基,,亦即,例如,上述C1-C4-卤代烷氧基定义中所述的任一基团,或5-氟-1-戊氧基,5-氯-1-戊氧基,5-溴-1-戊氧基,5-碘-1-戊氧基,5,5,5-三氯-1-戊氧基,十一氟戊氧基,6-氟-1-己氧基,6-氯-1-己氧基,6-溴-1-己氧基,6-碘-1-己氧基,6,6,6-三氯-1-己氧基或十二氟代己氧基;- C1-C4-烷硫基:SCH3、SC2H5、SCH2-C2H5、SCH(CH3)2、正丁硫基、SCH(CH3)-C2H5、SCH2-CH(CH3)2或SC(CH3)3,优选SCH3或SC2H5;- C1-C4-卤代烷硫基:部分或全部由氟、氯、溴和/或碘取代的上述C1-C4-烷硫基,亦即,例如,SCH2F、SCHF2、SCF3、SCH2Cl、SCH(Cl)2、SC(Cl)3、氯氟甲硫基、二氯氟甲硫基、氯二氟甲硫基、2-氟乙硫基、2-氯乙硫基、2-溴乙硫基、2-碘乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、2,2,2-三氯乙硫基、SC2F5、2-氟丙硫基、3-氟丙硫基、2,2-二氟丙硫基、2,3-二氟丙硫基、2-氯丙硫基、3-氯丙硫基、2,3-二氯丙硫基、2-溴丙硫基、3-溴丙硫基、3,3,3-三氟丙硫基、3,3,3-三氯丙硫基、SCH2-C2F5、SCF2-C2F5、1-(CH2F)-2-氟乙硫基、1-(CH2Cl)-2-氯乙硫基、1-(CH2Br)-2-溴乙硫基、4-氟丁硫基、4-氯丁硫基、4-溴丁硫基或SCF2-CF2-C2F5;优选SCHF2、SCF3、二氯氟甲硫基、氯二氟甲硫基或2,2,2-三氟乙硫基;- C1-C6-烷硫基:上述C1-C4-烷硫基,或者,例如正戊硫基,1-甲基丁硫基,2-甲基丁硫基,3-甲基丁硫基,2,2-二甲基丙硫基,1-乙基丙硫基,正己硫基,1,1-二甲基丙硫基,1,2-二甲基丙硫基,1-甲基戊硫基,2-甲基戊硫基,3-甲基戊硫基,4-甲基戊硫基,1,1-二甲基丁硫基,1,2-二甲基丁硫基,1,3-二甲基丁硫基,2,2-二甲基丁硫基,2,3-二甲基丁硫基,3,3-二甲基丁硫基,1-乙基丁硫基,2-乙基丁硫基,1,1,2-三甲基丙硫基,1,2,2-三甲基丙硫基,1-乙基-1-甲基丙硫基或1-乙基-2-甲基丙硫基,优选SCH3、SC2H5、SCH2-C2H5、SCH(CH3)2、正丁硫基、SC(CH3)3、正戊硫基或正己硫基;- (C1-C4-烷基)羰基,CO-CH3、CO-C2H5、CO-CH2-C2H5、CO-CH(CH3)2、正丁基羰基、CO-CH(CH3)-C2H5、CO-CH2-CH(CH3)2或CO-C(CH3)3,优选CO-CH3或CO-C2H5;- (C1-C4-卤代烷基)羰基:被氟、氯、溴和/或碘部分或全部取代的上述(C1-C4-烷基)羰基,亦即例如CO-CH2F,CO-CHF2,CO-CF3,CO-CH2Cl,CO-CH(Cl)2,CO-C(Cl)3,氯氟甲基羰基,二氯氟甲基羰基,氯二氟甲基羰基,2-氟乙基羰基,2-氯乙基羰基,2-溴乙基羰基,2-碘乙基羰基,2,2-二氟乙基羰基,2,2,2-三氟乙基羰基,2-氯-2-氟乙基羰基,2-氯-2,2-二氟乙基羰基,2,2-二氯-2-氟乙基羰基,2,2,2-三氯乙基羰基,CO-C2F5,2-氟丙基羰基,3-氟丙基羰基,2,2-二氟丙基羰基,2,3-二氟丙基羰基,2-氯丙基羰基,3-氯丙基羰基,2,3-二氯丙基羰基,2-溴丙基羰基,3-溴丙基羰基,3,3,3-三氟丙基羰基,3,3,3-三氯丙基羰基,CO-CH2-C2F5,CO-CF2-C2F5,1-(CH2F)-2-氟乙基羰基,1-(CH2Cl)-2-氯乙基羰基,1-(CH2Br)-2-溴乙基羰基,4-氟丁基羰基,4-氯丁基羰基,4-溴丁基羰基或CO-(n-C4H9),优选CO-CF3、CO-CH2Cl或2,2,2-三氟乙基羰基;- (C1-C4-烷基)羰氧基:O-CO-CH3、O-CO-C2H5、O-CO-CH2-C2H5、O-CO-CH(CH3)2、O-CO-CH2-CH2-C2H5、O-CO-CH(CH3)-C2H5、O-CO-CH2-CH(CH3)2或O-CO-C(CH3)3,优选O-CO-CH3或O-CO-C2H5;- (C1-C4-卤代烷基)羰氧基:被氟、氯、溴和/或碘部分或全部取代的上述(C1-C4-烷基)羰基,亦即例如O-CO-CH2F,O-CO-CHF2,O-CO-CF3,O-CO-CH2Cl,O-CO-CH(Cl)2,O-CO-C(Cl)3,氯氟甲基羰氧基,二氯氟甲基羰氧基,氯二氟甲基羰氧基,2-氟乙基羰氧基,2-氯乙基羰氧基,2-溴乙基羰氧基,2-碘乙基羰氧基,2,2-二氟乙基羰氧基,2,2,2-三氟乙基羰氧基,2-氯-2-氟乙基羰氧基,2-氯-2,2-二氟乙基羰氧基,2,2-二氯-2-氟乙基羰氧基,2,2,2-三氯乙基羰氧基,O-CO-C2F5,2-氟丙基羰氧基,3-氟丙基羰氧基,2,2-二氟丙基羰氧基,2,3-二氟丙基羰氧基,2-氯丙基羰氧基,3-氯丙基羰氧基,2,3-二氯丙基羰氧基,2-溴丙基羰氧基,3-溴丙基羰氧基,3,3,3-三氟丙基羰氧基,3,3,3-三氯丙基羰氧基,O-CO-CH2-C2F5,O-CO-CF2-C2F5,1-(CH2F)-2-氟乙基羰氧基,1-(CH2Cl)-2-氯乙基羰氧基,1-(CH2Br)-2-溴乙基羰氧基,4-氟丁基羰氧基,4-氯丁基羰氧基,4-溴丁基羰氧基或九氟丁基羰氧基,优选O-CO-CF3、O-CO-CH2Cl或2,2,2-三氟乙基羰氧基;- (C1-C4-烷氧基)羰基:CO-OCH3,CO-OC2H5,CO-OCH2-C2H5,CO-OCH(CH3)2,正丁氧基羰基,CO-OCH(CH3)-C2H5,CO-OCH2-CH(CH3)2或CO-OC(CH3)3,优选CO-OCH3或CO-OC2H5;- C1-C4-烷基亚磺酰基:SO-CH3,SO-C2H5,SO-CH2-C2H5,SO-CH(CH3)2,SO-(n-C4H9),SO-CH(CH3)-C2H5,SO-CH2-CH(CH3)2或SO-C(CH3)3;- C1-C6-烷基亚磺酰基:上述C1-C4-烷基亚磺酰基或SO-(n-C5H11),1-甲基丁基-SO,2-甲基丁基-SO,3-甲基丁基-SO,2,2-二甲基丙基-SO,1-乙基丙基-SO,正己基-SO,1,1-二甲基丙基-SO,1,2-二甲基丙基-SO,1-甲基戊基-SO,2-甲基戊基-SO,3-甲基戊基-SO,4-甲基戊基-SO,1,1-二甲基丁基-SO,1,2-二甲基丁基-SO,1,3-二甲基丁基-SO,2,2-二甲基丁基-SO,2,3-二甲基丁基-SO,3,3-二甲基丁基-SO,1-乙基丁基-SO,2-乙基丁基-SO,1,1,2-三甲基丙基-SO,l,2,2-三甲基丙基-SO,1-乙基-1-甲基丙基-SO或1-乙基-2-甲基丙基-SO,优选SO-CH3,SO-C2H5,SO-CH2-C2H5,SO-CH(CH3)2,SO-(n-C4H9),SO-C(CH3)3,SO-(n-C5H11)或SO-(n-C6H13);- C1-C4-烷基磺酰基:SO2-CH3,SO2-C2H5,SO2-CH2-C2H5,SO2-CH(CH3)2,SO2-(n-C4H9),SO2-CH(CH3)-C2H5,SO2-CH2-CH(CH3)2或SO2-C(CH3)3;- C1-C6-烷基磺酰基:上述C1-C4-烷基磺酰基或SO2-(n-C5H11),1-甲基丁基-SO2,2-甲基丁基-SO2,3-甲基丁基-SO2,2,2-二甲基丙基-SO2,1-乙基丙基-SO2,正己基-SO2,1,1-二甲基丙基-SO2,1,2-二甲基丙基-SO2,1-甲基戊基-SO2,2-甲基戊基-SO2,3-甲基戊基-SO2,4-甲基戊基-SO2,1,1-二甲基丁基-SO2,1,2-二甲基丁基-SO2,1,3-二甲基丁基-SO2,2,2-二甲基丁基-SO2,2,3-二甲基丁基-SO2,3,3-二甲基丁基-SO2,1-乙基丁基-SO2,2-乙基丁基-SO2,1,1,2-三甲基丙基-SO2,1,2,2-三甲基丙基-SO2,1-乙基-1-甲基丙基-SO2或1-乙基-2-甲基丙基-SO2,优选SO2-CH3,SO2-C2H5,SO2-CH2-C2H5,SO2-CH(CH3)2,SO2-(n-C4H9),SO2-C(CH3)3,SO2-(n-C5H11)或SO2-(n-C6H13);- C1-C4-卤代烷基磺酰基:被氟、氯、溴和/或碘部分或全部取代的上述C1-C4-烷基磺酰基,亦即,例如SO2-CH2F,SO2-CHF2,SO2-CF3,SO2-CH2Cl,SO2-CH(Cl)2,SO2-C(Cl)3,氯氟甲基磺酰基,二氯氟甲基磺酰基,氯二氟甲基磺酰基,2-氟乙基磺酰基,2-氯乙基磺酰基,2-溴乙基磺酰基,2-碘乙基磺酰基,2,2-二氟乙基磺酰基,2,2,2-三氟乙基磺酰基,2-氯-2-氟乙基磺酰基,2-氯-2,2-二氟乙基磺酰基,2,2-二氯-2-氟乙基磺酰基,2,2,2-三氯乙基磺酰基,SO2-C2F5,2-氟丙基磺酰基,3-氟丙基磺酰基,2,2-二氟丙基磺酰基,2,3-二氟丙基磺酰基,2-氯丙基磺酰基,3-氯丙基磺酰基,2,3-二氯丙基磺酰基,2-溴丙基磺酰基,3-溴丙基磺酰基,3,3,3-三氟丙基磺酰基,3,3,3-三氯丙基磺酰基,SO2-CH2-C2F5,SO2-CF2-C2F5,1-(氟甲基)-2-氟乙基磺酰基,1-(氯甲基)-2-氯乙基磺酰基,1-(溴甲基)-2-溴乙基磺酰基,4-氟丁基磺酰基,4-氯丁基磺酰基,4-溴丁基磺酰基或九氟丁基磺酰基,优选SO2-CH2Cl,SO2-CF3或2,2,2-三氟乙基磺酰基;- 二(C1-C4-烷基)氨基:N(CH3)2,N(C2H5)2,N(CH2-C2H5)2,N[CH(CH3)2]2,N,N-二丁基氨基,N,N-二(1-甲基丙基)氨基,N,N-二(2-甲基丙基)氨基,N[C(CH3)3]2,N-乙基-N-甲基氨基,N-甲基-N-丙基氨基,N-甲基-N-(1-甲基乙基)氨基,N-丁基-N-甲基氨基,N-甲基-N-(1-甲基丙基)氨基,N-甲基-N-(2-甲基丙基)氨基,N-(1,1-二甲基乙基)-N-甲基氨基,N-乙基-N-丙基氨基,N-乙基-N-(1-甲基乙基)氨基,N-丁基-N-乙基氨基,N-乙基-N-(1-甲基丙基)氨基,N-乙基-N-(2-甲基丙基)氨基,N-乙基-N-(1,1-二甲基乙基)氨基,N-(1-甲基乙基)-N-丙基氨基,N-丁基-N-丙基氨基,N-(1-甲基丙基)-N-丙基氨基,N-(2-甲基丙基)-N-丙基氨基,N-(1,1-二甲基乙基)-N-丙基氨基,N-丁基-N-(1-甲基乙基)氨基,N-(1-甲基乙基)-N-(1-甲基丙基)氨基,N-(1-甲基乙基)-N-(2-甲基丙基)氨基,N-(1,1-二甲基乙基)-N-(1-甲基乙基)氨基,N-丁基-N-(1-甲基丙基)氨基,N-丁基-N-(2-甲基丙基)氨基,N-丁基-N-(1,1-二甲基乙基)氨基,N-(1-甲基丙基)-N-(2-甲基丙基)氨基,N-(1,1-二甲基乙基)-N-(1-甲基丙基)氨基或N-(1,1-二甲基乙基)-N-(2-甲基丙基)氨基,优选N(CH3)2或N(C2H5)2,- C3-C6-链烯基:丙-1-烯-1-基、烯丙基、1-甲基乙烯基、1-丁烯-1-基、1-丁烯-2-基、1-丁烯-3-基、2-丁烯-1-基、1-甲基-丙-1-烯-1-基、2-甲基-丙-1-烯-1-基、1-甲基-丙-2-烯-1-基、2-甲基-丙-2-烯-1-基、正戊烯-1-基、正戊烯-2-基、正戊烯-3-基、正戊烯-4-基、1-甲基丁-1-烯-1-基、2-甲基丁-1-烯-1-基、3-甲基丁-1-烯-1-基、1-甲基丁-2-烯-1-基、2-甲基丁-2-烯-1-基、3-甲基丁-2-烯-1-基、1-甲基丁-3-烯-1-基、2-甲基丁-3-烯-1-基、3-甲基丁-3-烯-1-基、1,1-二甲基丙-2-烯-1-基、1,2-二甲基丙-1-烯-1-基、1,2-二甲基丙-2-烯-1-基、1-乙基丙-1-烯-2-基、1-乙基丙-2-烯-1-基、n-己-1-烯-1-基、n-己-2-烯-1-基、n-己-3-烯-1-基、n-己-4-烯-1-基、n-己-5-烯-1-基、1-甲基戊-1-烯-1-基、2-甲基戊-1-烯-1-基、3-甲基戊-1-烯-1-基、4-甲基戊-1-烯-1-基、1-甲基戊-2-烯-1-基、2-甲基戊-2-烯-1-基、3-甲基戊-2-烯-1-基、4-甲基戊-2-烯-1-基、1-甲基戊-3-烯-1-基、2-甲基戊-3-烯-1-基、3-甲基戊-3-烯-1-基、4-甲基戊-3-烯-1-基、1-甲基戊-4-烯-1-基、2-甲基戊-4-烯-1-基、3-甲基戊-4-烯-1-基、4-甲基戊-4-烯-1-基、1,1-二甲基丁-2-烯-1-基、1,1-二甲基丁-3-烯-1-基、1,2-二甲基丁-1-烯-1-基、1,2-二甲基丁-2-烯-1-基、1,2-二甲基丁-3-烯-1-基、1,3-二甲基丁-1-烯-1-基、1,3-二甲基丁-2-烯-1-基、1,3-二甲基丁-3-烯-1-基、2,2-二甲基丁-3-烯-1-基、2,3-二甲基丁-1-烯-1-基、2,3-二甲基丁-2-烯-1-基、2,3-二甲基丁-3-烯-1-基、3,3-二甲基丁-1-烯-1-基、3,3-二甲基丁-2-烯-1-基、1-乙基丁-1-烯-1-基、1-乙基丁-2-烯-1-基、1-乙基丁-3-烯-1-基、2-乙基丁-1-烯-1-基、2-乙基丁-2-烯-1-基、2-乙基丁-3-烯-1-基、1,1,2-三甲基丙-2-烯-1-基、1-乙基-1-甲基丙-2-烯-1-基、1-乙基-2-甲基丙-1-烯-1-基和1-乙基-2-甲基丙-2-烯-1-基;- C3-C6-炔基:丙-1-炔-1-基,丙-2-炔-1-基,n-丁-1-炔-1-基,n-丁-1-炔-3-基,n-丁-1-炔-4-基,n-丁-2-炔-1-基,n-戊-1-炔-1-基,n-戊-1-炔-3-基,n-戊-1-炔-4-基,n-戊-1-炔-5-基,n-戊-2-炔-1-基,n-戊-2-炔-4-基,n-戊-2-炔-5-基,3-甲基丁-1-炔-3-基,3-甲基丁-1-炔-4-基,n-己-1-炔-1-基,n-己-1-炔-3-基,n-己-1-炔-4-基,n-己-1-炔-5-基,n-己-1-炔-6-基,n-己-2-炔-1-基,n-己-2-炔-4-基,n-己-2-炔-5-基,n-己-2-炔-6-基,n-己-3-炔-1-基,n-己-3-炔-2-基,3-甲基戊-1-炔-1-基,3-甲基戊-1-炔-3-基,3-甲基戊-1-炔-4-基,3-甲基戊-1-炔-5-基,4-甲基戊-1-炔-1-基,4-甲基戊-2-炔-4-基和4-甲基戊-2-炔-5-基,优选丙-2-炔-1-基;- C3-C4-链烯氧基:烯丙氧基,丁-1-烯-3-基氧基,丁-1-烯-4-基氧基,丁-2-烯-1-基氧基,1-甲基丙-2-烯基氧基或2-甲基丙-2-烯基氧基,优选烯丙氧基;- C3-C4-炔氧基:炔丙氧基,丁-1-炔-3-基氧基,丁-1-炔-4-基氧基,丁-2-炔-1-基氧基,1-甲基丙-2-炔基氧基或2-甲基丙-2-炔基氧基,优选炔丙氧基;- C3-C4-炔硫基:炔丙硫基,丁-1-炔-3-基硫基,丁-1-炔-4-基硫基,丁-2-炔-1-基硫基,1-甲基丙-2-炔基硫基或2-甲基丙-2-炔基硫基,优选炔丙硫基;- C3-C4-链烯硫基:烯丙硫基,丁-1-烯-3-基硫基,丁-1-烯-4-基硫基,丁-2-烯-1-基硫基,1-甲基丙-2-烯基硫基或2-甲基丙-2-烯基硫基,优选烯丙硫基;- C3-C7-环烷基:环丙基、环丁基、环戊基、环己基或环庚基;优选环丙基;3-至7-元饱和杂环体系特别是指具有:- 一个或两个氧和/或- 一个或两个硫原子的杂环体系。
可以含有羰基或硫代羰基环组成部分的饱和杂环的实例有:环氧乙烷基,硫杂丙环基,氧杂环丁烷-2-基,氧杂环丁烷-3-基,硫杂环丁烷-2-基,硫杂环丁烷-3-基,四氢呋喃-2-基,四氢呋喃-3-基,四氢噻吩-2-基,四氢噻吩-3-基,1,3-二氧戊环-2-基,1,3-二氧戊环-4-基,1,3-氧硫杂戊环(Oxathiolan)-2-基,1,3-氧硫杂戊环-4-基,1,3-氧硫杂戊环-5-基,1,3-二硫戊环-2-基,1,3-二硫戊环-4-基,四氢吡喃-2-基,四氢吡喃-3-基,四氢吡喃-4-基,四氢噻喃-2-基,四氢噻喃-3-基,四氢吡喃-4-基,1,3-二噁烷-2-基,1,3-二噁烷-4-基,1,3-二噁烷-5-基,1,4-二噁烷-2-基,1,3-氧硫杂环己烷-2-基,1,3-氧硫杂环己烷-4-基,1,3-氧硫杂环己烷-5-基,1,3-氧硫杂环己烷-6-基,1,4-氧硫杂环己烷-2-基,1,4-氧硫杂环己烷-3-基,氧杂庚环(Oxepan)-2-基,氧杂庚环-3-基,氧杂庚环-4-基,噻庚环(Thiepan)-2-基,噻庚环-3-基,噻庚环-4-基,1,3-二氧杂庚环(Dioxepan)-2-基,1,3-二氧杂庚环-4-基,1,3-二氧杂庚环-5-基,1,3-二氧杂庚环-6-基,1,3-二噻庚环(Dithiepan)-2-基,1,3-二噻庚环-4-基,1,3-二噻庚环-5-基,1,3-二噻庚环-6-基,1,4-二氧杂庚环-2-基和1,4-二氧杂庚环-7-基。
所有环烷基和杂环基环均优选为未取代的,或者带有一个取代基。
根据本发明3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物I作为除草剂的用途,优选这些化合物I,其中各变量无论是单独存在还是组合存在均定义如下:X 为氧;Y 为氧;Z 为化学键,C1-C4-亚烷基,氧或硫;R1 为氢,氨基或C1-C6-烷基;R2 为氢,卤素,C1-C6-烷基,C1-C6-卤代烷基或C1-C6-烷磺酰基;R3 为氢;R4 为氢,氟或氯;R5 为氰基或卤素;R6 为氢,C3-C6-环烷基或包含一个氧或硫原子的3-7元饱和杂环基,其中每个环烷基或每个杂环基环均可以含有羰基或硫代羰基环组成部分,并且其中的每一环烷基和杂环基环均可以为未取代的,或者可以带有1-4个独立选自如下的取代基:氰基,硝基,氨基,羟基,卤素,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-氰基烷基,C1-C4-羟基烷基,C1-C4-氨基烷基,C1-C4-烷氧基,C1-C4-卤代烷氧基,C1-C4-烷硫基,C1-C4-卤代烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷基磺酰基,C1-C4-卤代烷基磺酰基,(C1-C4-烷氧基)羰基,(C1-C4-烷基)羰基,(C1-C4-卤代烷基)羰基,(C1-C4-烷基)羰氧基,(C1-C4-卤代烷基)羰氧基,二(C1-C4-烷基)氨基,C3-C6-链烯基,C3-C6-炔基,C3-C4-链烯氧基,C3-C4-链烯硫基,C3-C4-炔氧基和C3-C4-炔硫基,R6 特别为氢,C3-C6-环烷基或包含一个氧或硫原子的3-7元饱和杂环基,其中各环烷基或各杂环基环均可以含有羰基或硫代羰基环组成部分。
更特别优选式Ia的3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物{=I,其中X和Y=氧,R1=甲基,R2=三氟甲基,R3=氢,R4=氟,R5=氯和Z=化学键}尤其是下表1中所列的化合物Ia.1-Ia.51:表1
序号 | R6 |
1a.1 | 环丙基 |
1a.2 | 环丁基 |
1a.3 | 环戊基 |
1a.4 | 环己基 |
1a.5 | 环庚基 |
1a.6 | 环氧乙烷-2-基 |
1a.7 | 氧杂环丁烷-2-基 |
1a.8 | 四氢呋喃-2-基 |
1a.9 | 四氢吡喃-2-基 |
1a.10 | 氧杂庚环-2-基 |
1a.11 | 硫杂丙环-2-基 |
1a.12 | 硫杂环丁烷-2-基 |
1a.13 | 四氢噻吩-2-基 |
1a.14 | 四氢噻喃-2-基 |
1a.15 | 噻庚环-2-基 |
1a.16 | 氧杂环丁烷-3-基 |
1a.17 | 四氢呋喃-3-基 |
1a.18 | 四氢吡喃-3-基 |
1a.19 | 氧杂庚环-3-基 |
1a.20 | 硫杂环丁烷-3-基 |
1a.21 | 四氢噻吩-3-基 |
1a.22 | 四氢噻喃-3-基 |
1a.23 | 噻庚环-3-基 |
1a.24 | 四氢吡喃-4-基 |
1a.25 | 氧杂庚环-4-基 |
1a.26 | 四氢噻喃-4-基 |
1a.27 | 噻庚环-4-基 |
1a.28 | 2-氧代环丙基 |
1a.29 | 2-氧代环丁基 |
1a.30 | 2-氧代环戊基 |
1a.31 | 2-氧代环己基 |
1a.32 | 2-氧代环庚基 |
1a.33 | 2-硫代环丙基 |
1a.34 | 2-硫代环丁基 |
1a.35 | 2-氧代氧杂环丁烷-3-基 |
1a.36 | 2-氧代四氢呋喃-3-基 |
1a.37 | 2-氧代-四氢吡喃-3-基 |
1a.38 | 2-氧代氧杂庚环-3-基 |
1a.39 | 2-硫代硫杂环丁烷-3-基 |
1a.40 | 2-硫代四氢噻吩-3-基 |
1a.41 | 2-硫代四氢噻喃-3-基 |
1a.42 | 2-硫代噻庚环-3-基 |
1a.43 | 2-硫代氧杂环丁烷-3-基 |
1a.44 | 2-硫代四氢呋喃-3-基 |
1a.45 | 2-硫代四氢吡喃-3-基 |
1a.46 | 2-硫代氧杂庚环-3-基 |
1a.47 | 2-氧代硫杂环丁烷-3-基 |
1a.48 | 2-氧代四氢噻吩-3-基 |
1a.49 | 2-氧代四氢噻喃-3-基 |
1a.50 | 2-氧代噻庚环-3-基 |
1a.51 | H |
此外亦特别优选下列式Ib-Ip的3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物,尤其是:- 化合物Ib.1-Ib.51,它们与相应的化合物Ia.1-Ia.51的区别仅在于R1为氢:- 化合物Ic.5-Ic.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于Y为硫:- 化合物Id.5-Id.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于R1为氢而Y为硫:- 化合物Ie.1-Ie.51,它们与相应的化合物Ia.1-Ia.51的区别仅在于Z为CH2:- 化合物If.1-If.51,它们与相应的化合物Ia.1-Ia.51的区别仅在于R1为氢以及Z为CH2:- 化合物Ig.5-Ig.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于Y为硫且Z为CH2:- 化合物Ih.5-Ih.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于R1为氢、Y为硫以及Z为CH2:- 化合物Ii.1-Ii.51,它们与相应的化合物Ia.1-Ia.51的区别仅在于Z为氧:- 化合物Ij.1-Ij.51,它们与相应的化合物Ia.1-Ia.51的区别仅在于R1为氢以及Z为氧:- 化合物Ik.5-Ik.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于Y为硫以及Z为氧:- 化合物I1.5-I1.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于R1为氢、Y为硫以及Z为氧:- 化合物Im.1-Im.51,它们与相应的化合物Ia.1-Ia.51的区别仅在于Z为硫:- 化合物In.1-In.51,它们与相应的化合物Ia.1-Ia.51的区别仅在于R1为氢和Z为硫:- 化合物Io.5-Io.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于Y和Z各自均为硫:- 化合物Ip.5-Ip.50,它们与相应的化合物Ia.5-Ia.50的区别仅在于R1为氢以及Y和Z各自均为硫:
本发明的式I 3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物可以通过各种途径制备,例如下列方法之一:方法A)
缩合取代的2-氨基苯酚或2-氨基苯硫酚与碳酸衍生物或羧酸衍生物:
双官能苯VII与碳酸衍生物或羧酸衍生物的缩合可以按照本领域公知的方式进行(例如参见Houben-Weyl,Methoden derorganischen Chemie,Georg,Thieme Verlag Stuttgart,Vol.E8c,第一版,1994,pp.247-284;Vol.E8b,第一版,1994,pp.881-901;Vol.E8a,第一版,1993,pp.1032-1078)。优选的碳酸衍生物或羧酸衍生物为相应的酯、酸酐、酰氯、原酸酯,二酰亚胺,腈类,亚氨基酯,三氯甲基-取代的化合物,异氰酸酯及其硫代类似物。
合适的溶剂/稀释剂尤为有机溶剂,例如芳烃(如苯、甲苯和邻-、间-、对-二甲苯),卤代烃(如二氯甲烷、氯仿和二氯乙烷),低级醇(如甲醇和乙醇),脂族或环状醚(如二甲氧基乙烷、四氢呋喃和二噁烷),羧酸酯(如乙酸乙酯),或非质子极性溶剂(如二甲基甲酰胺和二甲亚砜)。
如果需要,可以加入催化量的酸促进上述反应。适宜的酸尤为无机酸(如盐酸),或磺酸(如对-甲苯磺酸),或它们与含氮有机碱(如吡啶)形成的盐。酸的用量按VII的量计为0.01-5mol%。
反应温度优选为20℃-所述反应混合物的回流温度,特别是60℃-回流温度。
可以使用大约化学计算量或者过量的碳酸衍生物或羧酸衍生物。在适当情况下,它们的用量也可以大大过量,或者可以在无溶剂的情况下进行上述反应。以所用VII的量为基准,优选使用大约化学计算量或多至10摩尔当量过量的上述碳酸或羧酸衍生物。
取代的2-氨基苯酚和-苯硫酚能够很方便地通过还原相应的2-硝基苯酚或-苯硫酚VIII制得(参见例如Houben-Weyl,Methoden derorganischen Chemie,Georg Thieme Verlag,Stuttgart,Vol.XI/1,第四版,1957,p.431等)。
合适的还原剂尤其为:- 元素金属,如铁、锡和锌,- 氢/适宜催化剂,如钯或铂-碳或阮内镍,或者- 复合氢化物,如LiAlH4和NaBH4,如果合适的话还存在有催化剂。
依据所用还原剂,合适的溶剂通常为羧酸(如乙酸和丙酸),无机酸(如盐酸或硫酸),醇类(如甲醇和乙醇),醚类(如乙醚、甲基叔丁基醚、四氢呋喃和二噁烷),芳族化合物(如苯和甲苯),以及这些溶剂的混合物。
反应可以在(-100)℃-所述反应混合物沸点的温度下进行。
一般使用大约化学计算量的起始化合物。然而,在特殊情况下,宜使用多倍过量的一种或另一种组分。
适宜的消去试剂尤其为:- 对于未取代或取代的烷基苯酚类:三甲基甲硅烷基碘、三溴化硼、三氯化硼、三氯化铝、氯化锂或溴化氢;- 对于未取代或取代的苄基苯酚或苯硫酚类:三氟化硼、氢氟酸或氢/催化剂,优选贵金属催化剂,如钯或铂;- 对于未取代或取代的芳基酯或芳基硫酯类:碳酸氢钠、碳酸钠、碳酸钾、氢氧化钠、氢氧化钾、甲醇钠、氯化氢、硫酸、氨、肼或锌。
优先选择对所述消去试剂呈惰性的溶剂/稀释剂。当使用卤化物三甲基甲硅烷基碘、三溴化硼、三氯化硼或三氯化铝时,特别优选卤化溶剂,如二氯甲烷、氯仿、四氯化碳和二氯乙烷。溴化氢优选以水溶液形式使用,更特别优选48%重量浓度的溶液形式;氯化锂优选在极性溶剂(如低级醇、二甲亚砜和二甲基甲酰胺)中使用;氢解方法优选在低级醇或羧酸中进行,如果合适的话加入氢转移剂,如环己烯和环己二烯。无机碱或无机酸以及含氮碱优选在含水介质中使用。依据所用试剂的溶解性,如果合适的话可以加入有机溶剂,例如低级醇。
消去反应的温度优选为0℃-所述反应混合物的沸点。
优选使用大约化学计算量或者过量的消去试剂。特别优选1-10摩尔当量的过量(以所用IX的量为基准)方法B)
氧或硫亲核试剂对芳香性结合的氟的交换反应按本领域公知的方式进行(例如,参见Houben-Weyl,Methoden der organischenChemie,Georg Thieme Verlag,Stuttgart,1976,Vol.6/1c pp.146-202和Vol.IX,第四版,1955,pp.7-18)。
下列试剂为该反应的优选反应参与物:- 对于用OR交换F的反应:苯甲酸钾、亚硝酸钠、氢氧化钠、氢氧化钾、碳酸钾、苯甲醛肟、乙酸钠、乙酸钾、甲醇钠、甲醇钾、三甲基硅烷醇钠、苹果酸二甲酯。- 对于用SR交换F的反应:硫化钠、硫化氢钠、硫化氢钾、苄基硫醇。
在某些情况下,反应可以在无溶剂/稀释剂存在的情况下进行。如果使用溶剂/稀释剂,则优选使用能充分溶解氧或硫转移试剂的那些溶剂。特别优选醇类(如乙醇、丙醇或叔丁醇),非质子极性溶剂(如二甲基甲酰胺或二甲基乙酰胺),环醚(如二噁烷或四氢呋喃),或脂族醚(如二甲氧基乙烷)。
反应温度优选20℃至所述反应混合物的回流温度,特别是60℃至回流温度。
可以使用大约化学计算量或者过量的氧或硫转移试剂。在适当情况下,它们的用量也可以大大过量。以所用VI的量为基准,优选使用大约化学计算量或多至10摩尔当量过量的上述转移试剂。
新的硝基苯基尿嘧啶VI可以按照本领域公知的方式通过硝化苯基尿嘧啶V制得(参见,例如,Houben-Weyl,Methoden der organischenChemie,Georg Thieme Verlag Stuttgart,Vol.10/1,1971,p.479以后):
适宜的硝化试剂尤其为硝酸(与硫酸或乙酸酐形成的混合物形式),或硝鎓盐,具体为四氟硼酸硝。硝酸与硫酸的混合物可以由这两种组分以任何需要比例组成;优选其中硫酸比例极高或用作溶剂的这些混合物。类似的约定也适用于硝酸与乙酸酐的混合物。四氟硼酸硝优选在非质子极性溶剂(例如乙腈或硝基甲烷)中使用。
反应温通常为(-80)至80℃,特别是(-20)℃-30℃。
当硝化反应中使用硝酸试剂时,该方法优选使用等摩尔量或者特别优选使用过量的硝化试剂来进行。这种过量可以是V用量的多倍。四氟硼酸硝的用量优选与V等摩尔量,或者为介于1.1和1.5摩尔当量之间的轻微过量。
苯基尿嘧啶V为新化合物。它们可以按照本领域公知的方法由式III的芳基脲制备:或者由式IV的N-芳基酰苯胺制备:(L2=离去基团,例如C1-C4-烷基或苯基)。相应的方法记载于例如WO97/02253中。这一申请还描述了许多方法,根据这些方法可以类似地制备芳基脲III或N-芳基酰苯胺IV。详情参见这一申请。芳基脲III和N-芳基酰苯胺IV均为新的,并且也构成了本发明主题的一部分。方法C):
按照本领域公知的方式使3-苯基嘧啶二酮衍生物I(其中R1为氢)与烷基化化合物II反应:L1为常规离去基团,如卤素(优选氯、溴或碘),(卤代)烷基磺酰氧基(优选甲磺酰氧基或三氟甲基磺酰氧基),芳基磺酰氧基(优选甲苯磺酰氧基),和烷氧基磺酰氧基(优选甲氧基磺酰氧基或乙氧基磺酰氧基)。
该方法通常在惰性有机溶剂中进行,例如质子性溶剂(如低级醇,优选甲醇或乙醇),如果需要以含水的混合物形式使用,或者非质子传递溶剂(例如脂族或环状醚,如甲基叔丁基醚、1,2-二甲氧基乙烷、四氢呋喃和二噁烷),脂族酮(如丙酮、二乙酮和甲乙酮),酰胺(如二甲基甲酰胺和N-甲基吡咯烷酮),亚砜(如二甲亚砜),脲(如四甲基脲和1,3-二甲基四氢-2(1H)-嘧啶酮),羧酸酯(如乙酸乙酯),或卤代脂族或芳族烃(如二氯甲烷、二氯乙烷、氯苯和二氯苯)。
如果需要,该方法可以在碱存在下进行。适宜的碱不仅可以为无机碱,例如碳酸盐(如碳酸钠和碳酸钾)、碳酸氢盐(如碳酸氢钠和碳酸氢钾)和碱金属氢化物(如氢化钠和氢化钾),而且还可以为有机碱,例如胺(如三乙胺、吡啶和N,N-二乙基苯胺),或碱金属醇盐(如甲醇钠、乙醇钠和叔丁醇钾)。
按起始物质I(其中R1=氢)的用量计,碱和烷基化剂II的用量各自优选为0.5倍至两倍摩尔量。
一般来讲,反应温度为0℃-反应混合物的沸点,特别是0-60℃。
特别有利的是制备苯基嘧啶二酮衍生物I的钠盐,即通过使用大约等当量的苯基嘧啶二酮衍生物I(其中R1=H)和氢氧化钠,在20-25℃将苯基嘧啶二酮衍生物I(其中R1=H)溶于氢氧化钠水溶液中进行。然后可以通过例如利用合适的惰性溶剂沉淀或者蒸发溶剂来分离苯基嘧啶二酮衍生物I的相应钠盐。
其金属离子不为碱金属离子的苯基嘧啶二酮衍生物I的盐通常可以通过在水溶液中复分解相应的碱金属盐制备,而铵盐、磷鎓盐、锍盐和氧化锍盐的制备则采用氨和磷鎓、锍或氧化锍的氢氧化物完成。方法D)
迄今所知能够提供特别良好的胺化作用的胺化试剂为2,4-二硝基苯氧基胺,但也可以使用例如羟胺-O-磺酸(HOSA),即一种文献中早已公知的胺化试剂(参见,例如,E.Hofer等,Synthesis(合成)1983,466;W.Friedrichsen等,Heterocycles(杂环化合物)20(1983)1271;H.Hart等,Tetrahedron Lett.(四面体通讯)25(1984)2073;B.Vercek等,Monatsh.Chem.114(1983)789;G.Sosnousky等,Z.Naturforsch.38(1983)884;R.S.Atkinson等,J.Chem.Soc.Perkin Trans.1987,2787)。
胺化作用以本领域公知的方式进行(例如,参见T.Sheradsky,Tetrahedron Lett.1968,1909;M.P.Wentland等,J.Med.Chem.(药物化学杂志)27(1984),1103,以及特别是EP-A240 194,EP-A476 697和EP-A517 181,这些文献公开了尿嘧啶的胺化作用)。
反应通常在极性溶剂中进行,例如二甲基甲酰胺、N-甲基吡咯烷酮、二甲亚砜或乙酸乙酯,而且这些溶剂是迄今被证实特别适宜的溶剂。
适宜的碱例如为碱金属碳酸盐(如碳酸钾),碱金属醇盐(如甲醇钠和叔丁醇钾),或碱金属氢化物(如氢化钠)。
按起始物质的量计,碱和胺化试剂的用量各自优选为0.5倍至两倍摩尔量。方法E)
硫化其中X为氧的式I3-(苯并唑-7-基)嘧啶二酮衍生物:
硫化反应通常在惰性溶剂或稀释剂中进行,例如在芳烃(如甲苯和二甲苯),醚(如乙醚、1,2-二甲氧基乙烷和四氢呋喃),或有机胺(如吡啶)中进行。
特别适宜的硫化试剂为硫化磷(V)和2,4-双(4-甲氧基苯基)-1,3,2,4-二硫二磷杂丁环(dithiadiphosphetan)-2,4-二硫酮(“Lawesson试剂”)。
按要进行硫化的起始物质计,通常1-5倍摩尔量,所述转化就基本上能够完全进行。
反应温度一般为20-200℃,优选40℃-反应混合物的沸点。
除另有说明外,所有上述方法均可以在常压或所述反应混合物的自生压力下方便地进行。通常所用反应物的摩尔比为0.95∶1-5∶1。
一般来讲,反应混合物的后处理采用本领域公知的方式进行。例如,加水稀释反应溶液,随后通过过滤、结晶或溶剂提取的方式分离产物,或者可以按照下述方式进行:除去溶剂,将残留物分配到水和适宜的有机溶剂混合物内,然后处理有机相,得到所要产物。
无论是其异构体混合物形式还是纯净立体异构体形式,式I化合物及其农业上可用的盐都适合作为除草剂。包含式I化合物的除草组合物在控制非耕地的植物方面非常有效,特别是在高施用量的情况下更是如此。它们可以用来防治诸如小麦、稻、玉米、大豆和棉花之类作物中的阔叶杂草和禾本科杂草,而不会对作物造成明显的伤害。这种效果特别是出现在低施用量的情况下。
根据施用方法的不同,本发明化合物或含有它们的除草组合物也可以用于其它许多作物,用于消灭有害植物。适合的作物的实例是:洋葱、凤梨、花生、芦笋、甜菜(Beta vulgaris spec.altissima)、芜菁甜菜(Beta vulgaris spec.rapa)、蔓菁(Brassica napus var.napus)、芜菁甘蓝(Brassica napus var.napobrassica)、芜菁(Brassica rapa var.silvestris)、茶、红花、美洲山核桃、柠檬、甜橙、小果咖啡(中果咖啡、大果咖啡)、黄瓜、狗牙根、胡萝卜、油棕、欧洲草莓、大豆、陆地棉、(鸡脚棉、草棉、Gossypium vitifolium)、向日葵、巴西橡校、大麦、啤酒花、甘蓝、核桃、兵豆、亚麻、蕃茄、苹果属、木薯、紫花苜蓿、芭蕉属、烟草(黄花烟草)、油橄榄、稻、雪豆、菜豆、欧洲云杉、松属、豌豆、欧洲甜樱桃、桃、西洋梨、红醋栗、蓖麻、甘蔗、黑麦、马铃薯、芦黍(蜀黍)、可可、红车轴草、普通小麦、硬粒小麦、蚕豆、葡萄和玉米。
另外,化合物I也可以用在通过育种(包括基因工程方法育种)方式对除草剂产生耐药性的作物上。
本发明的组合物或活性成分可以在苗前或苗后进行。如果这种活性化合物对某种农作物是较不耐受的,那么可以采用这样的施用技术,即借助喷洒设备喷洒该除草组合物,以便尽可能地不要喷洒到敏感性农作物的叶片上,同时使活性成分到达生长于其下的不希望的植物的叶面上或到达未覆盖的土表上(苗后直接处理、铺施)。
化合物I或含有它们的除草组合物可以例如以可直接喷雾水溶液、粉剂、悬浮液(包括高浓度水悬剂、油悬剂或其它悬浮剂或分散液)、乳剂、油性分散液、糊剂、喷粉剂、撒施物或颗粒剂的形式,通过喷雾、弥雾、喷粉、撒施或浇泼方式施用。施用形式取决于预定目的;但在每种情况下,都应确保本发明的活性成分的分散尽可能的细微和均匀。
合适的惰性助剂主要包括:中至高沸点的矿物油馏分如煤油和柴油,进一步包括煤焦油和动植物油,脂族烃、环烃和芳烃,例如,石蜡、四氢化萘、烷基化萘及其衍生物、烷基化苯及其衍生物,醇如甲醇、乙醇、丙醇、丁醇和环己醇,酮如环己酮或强极性溶剂,例如胺,如N-甲基吡咯烷酮和水。
含水的使用形式是由乳油、悬浮液、糊剂、可湿性粉剂或可以用水分散的颗粒通过添加水而制备的。为了制备乳液、糊剂或油分散液,可以借助于润湿剂、粘附剂、分散剂或乳化剂,将3-(苯并唑-7-基)嘧啶二酮衍生物原药或其溶解在油或溶剂中的溶液在水中均化。另一方面,同样可以制备包含活性物质、润湿剂、粘附剂、分散剂或乳化剂以及(如需要的话)溶剂或油的浓缩物,这些浓缩物均适合用水稀释。
合适的表面活性剂为芳族磺酸(例如木质素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸)以及脂肪酸、烷基-和烷基芳基磺酸、烷基硫酸、十二烷基醚硫酸和脂肪醇硫酸的碱金属盐、碱土金属盐和铵盐,以及硫酸化的十六烷基醇、十七烷基醇和十八烷基醇以及脂肪醇乙二醇醚的盐,磺化的萘和其衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基苯酚醚,乙氧基化异辛基-、辛基-或壬基苯酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,烷芳基聚醚醇,异十三烷基醇、脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,十二烷基醇聚乙二醇醚乙酸酯,山梨醇酯、木素亚硫酸盐废液或甲基纤维素。
粉剂、撒施物和喷粉剂可以通过活性物质与固态载体的混合或混磨来制备。
颗粒剂例如包衣颗粒剂、浸渍颗粒剂和匀质颗粒剂可以通过将活性物质粘合在固态载体上来制备。固态载体是矿质土类如硅酸、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁、研碎的合成物质、肥料如硫酸铵、磷酸铵、硝酸铵、尿素和植物产品如谷类作物粉末、树皮、木材粉和核桃壳粉,纤维素粉或其他固态载体。
活性成分I在现用型制剂中的浓度可以在较宽的范围内变化。一般说来,制剂包含约0.001~98重量%、优选0.01~95重量%的至少一种活性成分。所用活性成分的纯度是90~100%,优选95~100%(根据NMR-光谱确定)。
例如,本发明化合物I可按下所述加工配制:I. 将20重量份的化合物I溶于如下组成的混合物:80重量份的烷基化苯、10重量份的8至10摩尔环氧乙烷与1摩尔油酸N-单乙醇酰胺的加合物、5重量份的十二烷基苯磺酸钙盐和5重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加合物。将溶液倒入到100,000重量份的水中,并使之细微分散,从而得到含0.02%重量活性成分的水分散液。II. 将20重量份的化合物I溶于如下组成的混合物:40重量份的环己酮、30重量份的异丁醇、20重量份的7摩尔环氧乙烷与1摩尔异辛基酚的加合物以及10重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加合物。将溶液倒入到100,000重量份的水中,使之细微分散,从而得到含0.02%(重量)活性成分的水分散液。III. 将20重量份的活性成分I溶于如下组成的混合物:25重量份的环己酮、65重量份沸点为210至280℃的矿物油馏分以及10重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加合物。将溶液倒入到100,000重量份的水中,使之细微分散,从而得到含0.02%(重量)活性成分的水分散液。IV. 将20重量份的活性成分I与3重量份的二异丁基萘磺酸钠、17重量份的来源于亚硫酸盐废液的木素磺酸钠盐和60重量份的粉状硅胶充分混合,并在锤磨中磨碎。通过将混合物细微分散于20,000重量份的水中,获得含有0.1%(重量)活性成分的喷雾混合物。V. 将3重量份的活性成分I与97重量份细分散的高岭土混合。从而获得含有3%(重量)活性成分的喷粉组合物。VI. 将20重量份的活性成分I与2重量份的十二烷基苯磺酸钙、8重量份的脂肪醇聚乙二醇醚、2重量份的酚/脲/甲醛缩合物的钠盐以及68重量份的石蜡样矿物油均匀混合。由此获得稳定的油分散剂。VII. 将1重量份的化合物I溶于如下组成的混合物:70重量份的环己酮、20重量份的乙氧基化异辛基苯酚和10重量份的乙氧基化蓖麻油。从而获得稳定的乳油。VIII. 将1重量份的化合物I溶于由80重量份的环己酮和20重量份的WettolEM31(基于乙氧基化蓖麻油的非离子乳化剂P33所组成的混合物,从而获得稳定的乳油。
为了拓宽作用谱和获得协同效应,本发明的[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物可以与众多的具有代表性的其他除草剂或生长调节活性成分混合并联合使用。例如合适的混合组分是1,2,4-噻二唑类、1,3,4-噻二唑类,酰胺类、氨基磷酸和其衍生物,氨基三唑类,N-酰苯胺、芳氧基/杂芳氧基链烷酸和它们的衍生物、苯甲酸及其衍生物、苯并噻二嗪酮类、2-芳酰基-1,3-环己二酮类、杂芳基芳基酮、苄基异噁唑烷酮类、间-CF3-苯基衍生物、氨基甲酸酯类、喹啉羧酸及其衍生物、氯乙酰苯胺类、环己烷-1,3-二酮衍生物、二嗪类、二氯丙酸及其衍生物、二氢苯并呋喃类、二氢呋喃-3-酮类、二硝基苯胺类、二硝基苯酚类、二苯基醚、联吡啶类、卤代羧酸和其衍生物、脲类、3-苯基尿嘧啶类、咪唑类、咪唑啉酮类、N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺类、噁二唑类、环氧乙烷类、苯酚类、芳氧基-和杂芳氧基苯氧基丙酸酯、苯基乙酸和其衍生物、苯基丙酸及其衍生物、吡唑类、苯基吡唑类、哒嗪类、吡啶羧酸及其衍生物、嘧啶基醚、磺酰胺类、磺酰脲类、三嗪类、三嗪酮类、三唑啉酮类、三唑甲酰胺类和尿嘧啶类。
此外,有利的是化合物I可以单独或与其他的除草剂联合施用,也可以以含其他作物保护剂的混剂形式使用,例如含杀虫剂或用于防治植物病原真菌或细菌的药剂的混剂。此外,有意义的是与无机盐溶液的可混溶性,该无机盐溶液可用来消除营养和微量元素的缺乏。同样可以加入无植物毒性的油和油的浓缩物。
根据防治目的、季节、靶体植物和生长期的不同,活性成分I的施用量是0.001至3.0,优选0.01至1.0kg/ha活性物质(a.s.)。
制备实施例
实施例13-[4-氯-2-环戊基-6-氟苯并噁唑-7-基]-1-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮(表1中的化合物Ia.3)
首先在30ml无水二甲苯内加入0.48g 3-[3-氨基-4-氯-6-氟-2-羟基苯基]-1-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮(中间体7)和0.14g三乙胺,然后在0℃下滴加0.18g环戊烷羰基氯与上述混合物混合。10分钟后,温热所得混合物至20℃,加入0.1g对甲苯磺酸吡啶鎓,加热回流混合物6小时。冷却后,甲苯相用水洗涤三次(每次30ml),硫酸钠干燥并减压除去溶剂。粗产物通过中压液相色谱(MPLC)纯化;流动相:环己烷/乙酸乙酯(9∶1)。产量:0.27g。1H-NMR(200 MHz,in CDCl3):δ[ppm]=7.25(d,1H),6.40(s,1H),3.60(s,3H),3.30(quin,1H),1.50-2.25(m,8H).中间体14-氯-2,6-二氟苯胺
混合35.5g 2,6-二氟苯胺与200ml浓乙酸,加热此混合物至80℃。混合42.4g磺酰氯与大约相同量的浓乙酸,并将此混合物逐滴加到上述加热溶液内。然后加热回流所得混合物6小时。冷却后,减压浓缩溶液,残留物与水和戊烷一同搅拌。滤出固体残留物,用水洗涤。将所得固体与200ml浓盐酸混合,加热回流2小时。冷却之后,溶液用氢氧化钠水溶液小心调节至弱碱性,并用乙酸乙酯(每次100ml)提取所得混合物三次。有机相用硫酸钠干燥,然后除去溶剂。产量:40g;1H-NMR(270 MHz,in CDCl3):δ[ppm]=6.85(d,2H),3.5-3.9(br,2H).中间体24-氯-2,6-二氟苯基异氰酸酯
将40g 4-氯-2,6-二氟苯胺溶于300ml无水甲苯。搅拌下,于20℃逐滴加入100ml氯甲酸三氯甲酯。缓慢加热混合物至回流状态。3.5小时后,浓缩混合物,所得异氰酸酯直接用于中间体3的合成。中间体33-[4-氯-2,6-二氟苯基]-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮
首先向300ml无水二甲基甲酰胺中加入7.2g氰化钠,然后在0℃下逐滴加入44g 3-氨基-4,4,4-三氟丁-2-烯酸乙酯(溶在少量二甲基甲酰胺内)。在此温度下搅拌混合物2小时。冷却混合物至(-20)℃,逐滴加入溶在少量无水四氢呋喃中的异氰酸酯(中间体2)。加毕后,温热混合物至20℃,搅拌18小时。减压除去挥发性组组份,然后将混合物与稀盐酸混合,用甲基叔丁基醚提取(三次,100ml)。以硫酸钠干燥有机相,进而除去溶剂。产量:72.0g;1H-NMR(270 MHz,CDCl3):δ[ppm]=7.10(d,2H),6.25(s,1H).中间体43-[4-氯-2,6-二氟苯基]-1-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮
首先向200ml无水二甲基甲酰胺中加入71g 3-[4-氯-2,6-二氟苯基]-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮,然后在20℃下加入29.0g碳酸钾,接着再逐滴加入29.8g甲基碘。搅拌混合物18小时。减压除去溶剂,将残留物与水混合,用甲基叔丁基醚提取所得混合物。提取物用硫酸钠干燥,然后减压除去溶剂。产量:58.0g.1H-NMR(270 MHz,in CDCl3):δ[ppm]=7.10(d,2H),6.40(s,1H),3.55(s,3H).中间体53-[4-氯-2,6-二氟-3-硝基苯基]-1-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮
将58g 3-[4-氯-2,6-二氟苯基]-1-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮溶于400ml浓硫酸,0℃下与逐滴加入的含10.7g 98%强度的硝酸和10ml浓硫酸的混合液混合。0℃搅拌所得混合物30分钟,然后20℃搅拌18小时。再于0℃下逐滴加入10.7g上述酸混合液。20℃搅拌混合物2小时,然后倒入冰水内,抽滤出所生成的沉淀物,水洗至中性。在真空干燥箱内干燥所得固体物。产量:58.0g;1H-NMR(270 MHz,in CDCl3):δ[ppm]=7.30(d,1H),6.40(s,1H),3.60(s,3H).中间体63-[4-氯-6-氟-2-羟基-3-硝基苯基]-]-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮
将30g 3-[4-氯-2,6-二氟-3-硝基苯基]-1-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮溶于100ml无水二甲基甲酰胺,与25.2g乙酸钠混合,100℃加热4小时。冷却后,减压除去溶剂,残留物与水混合;通过加稀盐酸调节pH到酸性范围,然后用甲基叔丁基醚提取混合物(三次,每次75ml)。得到含所需产物和通过交换硝基对位上的氟原子而形成的异构体的混合物。总产量:28.3g。粗产物的纯化在后续步骤(中间体7)中进行。 1H-NMR(270MHz,in CDCl3):δ[ppm]=7.05(d,1H),6.40(s,1H),3.55(s,3H).中间体73-[3-氨基-4-氯-6-氟-2-羟基苯基]-1-甲基-6-三氟甲基-2,4-(1H,3H)-嘧啶二酮
将28g粗产物(中间体6)溶于含260ml水、50ml乙醇和26.7ml浓盐酸的混合物。加热混合物至65℃,每批少量分多批加入20.7g铁粉。回流混合物6小时。冷却后,用乙酸乙酯(300ml)提取混合物。减压除去溶剂所得到的粗产物进而通过柱色谱纯化(流动相:环己烷/乙酸乙酯=8∶2)。产量:2.8g;1H-NMR(270MHz,in CDCl3):δ[ppm]=6.80(d,1H),6.30(s,1H),4.6-5.2(br,2H),3.50(s,3H).
除上述化合物外,下表2中列出了按照类似方法制备的其它3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物:I{z=化学键;R1=CH3;R2=CF3;R3=H;R5=Cl}表2:
实施例序号 | X | R4 | R6 | m.p.[℃] |
1 | O | F | 环戊基 | 油状物 |
2 | O | F | 环己基 | 油状物 |
3 | O | F | 四氢吡喃-3-基 | 油状物 |
4 | O | F | H | 185 |
5 | O | F | 环丙基 | 油状物 |
6 | O | F | 四氢吡喃-4-基 | 油状物 |
7 | O | F | 四氢噻喃-4-基 | 油状物 |
8 | O | F | 环丁基 | 油状物 |
9 | S | F | 环丁基 | 油状物 |
10 | O | H | 环戊基 | 油状物 |
11 | O | H | 环丙基 | 油状物 |
式I 3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮化合物的除草活性由下列温室试验证实:
所用的栽培容器为塑料花盆,盆中装有腐殖质含量约为3.0%的壤砂土作为基质。根据不同物种,分别播种不同试验植物的种子。
在苗前处理的情况下,播种后随即用分布性能良好的喷嘴喷施悬浮或乳化于水中的活性成分。花盆稍微浇些水,以促使种子萌发和生长,随后覆盖上透明塑料地膜,直到植物生根。除非受到活性成分的不利影响,覆盖应会使试验植物均匀的萌发。
对于苗后处理,根据植物的生长形式,先使试验植物生长至3至15cm高,此时方用悬浮或乳化于水中的活性成分处理。为此,可以直接播种试验植物并在同一花盆中生长,或者先以秧苗分开生长,然后在处理前几天将它们移栽到试验花盆中。苗后处理的施药量仅为15.6或7.8kg/ha a.s.(活性物质)。
根据物种的不同,将植物分别维持在10-25℃或20-35℃下。试验期历经2至4周。在此期间,悉心照料植物,并评价它们对具体处理物的反应。
以0至100的等级进行评价。这里100是指没有植物出苗或至少地上部分完全毁灭,而0是指无伤害或生长正常。温室实验中所用的植物由下列种类组成:
学名 | 通用名称 |
Abutilon theophrasti | 青麻 |
Amaranthus retroflexus | 西风谷 |
Chenopodium album | 藜 |
Solanum nigrum | 龙葵 |
在仅仅15.6或7.8kg/ha的施用量下,化合物Ia.3能完全毁灭上述4种试验植物(效力100%)。
Claims (11)
其中:
X 为氧或硫;
Y 为氧或硫;
Z 为化学键,C1-4-亚烷基,氧,硫,SO或SO2;
R1 为氢,氨基,C1-C6-烷基或C1-C6-卤代烷基;
R2 为氢,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷硫基,C1-C6-烷基亚磺酰基或C1-C6-烷磺酰基;
R3 为氢,卤素或C1-C6-烷基;
R4 为氢或卤素;
R5 为氰基,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基或C1-C6-卤代烷氧基;
R6 为氢,C3-C7-环烷基或包含1个或多个氧和/或硫原子的3-7元饱和杂环基,其中每个环烷基或每个杂环基环均可以含有羰基或硫代羰基环组成部分,
并且其中的每一环烷基和杂环基环均可以为未取代的,或者可以带有1-4个独立选自如下的取代基:氰基,硝基,氨基,羟基,卤素,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-氰基烷基,C1-C4-羟基烷基,C1-C4-氨基烷基,C1-C4-烷氧基,C1-C4-卤代烷氧基,C1-C4-烷硫基,C1-C4-卤代烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷基磺酰基,C1-C4-卤代烷基磺酰基,(C1-C4-烷氧基)羰基,(C1-C4-烷基)羰基,(C1-C4-卤代烷基)羰基,(C1-C4-烷基)羰氧基,(C1-C4-卤代烷基)羰氧基,二(C1-C4-烷基)氨基,C3-C6-链烯基,C3-C6-炔基,C3-C4-链烯氧基,C3-C4-链烯硫基,C3-C4-炔氧基和C3-C4-炔硫基,
条件是当Y为氧且Z为化学键时,则R6只能为氢,以及当Y为硫时,则R6不能为C3-C6-环烷基。
2.权利要求1所述的式I 3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮,其中
X 为氧;
Z 为化学键,C1-4-亚烷基,氧或硫;
R1 为氢,氨基或C1-C6-烷基;
R2 为氢,卤素,C1-C6-烷基,C1-C6-卤代烷基或C1-C6-烷磺酰基;
R3 为氢;
R4 为氢,氟或氯,以及
R5 为氰基或卤素。
3.权利要求1中所述的3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮I或其农业上可用的盐作为除草剂的应用
4.除草组合物,其包括除草有效量的至少一种权利要求1中所述的式I3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮或I的农业上可用的盐,和至少一种液体和/或固体载体,以及如果需要的话至少一种表面活性剂。
5.制备除草组合物的方法,该方法包括将除草有效量的至少一种权利要求1中所述的式I3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮或I的农业上可用的盐与至少一种液体和/或固体载体,以及如果需要的话至少一种表面活性剂混合。
6.防治有害植物的方法,它包括使除草有效量的至少一种权利要求1中所述的式I 3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮或I的农业上可用的盐作用于植物、其环境或作用于种子。
9.式V的三取代苯基尿嘧啶:
其中变量X以及R1-R5各自如权利要求1中定义。
11.制备权利要求1中所述的3-[苯并(噁/噻)唑-7-基]-1H-嘧啶-2,4-二酮的方法,该方法包括缩合式VII的氨基苯酚或氨基苯硫酚:
其中变量X以及R1-R5各自如权利要求1中定义,与羧酸衍生物或碳酸衍生物。
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TWI659016B (zh) * | 2011-11-25 | 2019-05-11 | 德商亞德維瑞醫藥有限公司 | 製備經取代之5-氟-1h-吡唑并吡啶類之中間體的方法 |
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DE50001813D1 (de) * | 1999-08-12 | 2003-05-22 | Basf Ag | Substituierte benzoxazole |
US20110160232A1 (en) | 2007-10-04 | 2011-06-30 | Pingda Ren | Certain chemical entities and therapeutic uses thereof |
WO2009114874A2 (en) | 2008-03-14 | 2009-09-17 | Intellikine, Inc. | Benzothiazole kinase inhibitors and methods of use |
US8637542B2 (en) | 2008-03-14 | 2014-01-28 | Intellikine, Inc. | Kinase inhibitors and methods of use |
CN102124009B (zh) | 2008-07-08 | 2014-07-23 | 因特利凯公司 | 激酶抑制剂及其使用方法 |
US8476431B2 (en) | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
IN2012DN01961A (zh) | 2009-08-17 | 2015-08-21 | Intellikine Llc | |
US9295673B2 (en) | 2011-02-23 | 2016-03-29 | Intellikine Llc | Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof |
WO2014153509A1 (en) | 2013-03-22 | 2014-09-25 | Millennium Pharmaceuticals, Inc. | Combination of catalytic mtorc 1/2 inhibitors and selective inhibitors of aurora a kinase |
CN103288683B (zh) * | 2013-06-20 | 2015-09-16 | 郑州福源动物药业有限公司 | 一种“一锅法”制备尼卡巴嗪的方法 |
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JPH0525143A (ja) * | 1991-07-15 | 1993-02-02 | Nissan Chem Ind Ltd | 3−フエニルウラシル誘導体および除草剤 |
US5169430A (en) * | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
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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 |
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US6077812A (en) * | 1997-02-26 | 2000-06-20 | Fmc Corporation | Cycloimido-substituted benzofused heterocyclic herbicides |
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JP2002529481A (ja) | 2002-09-10 |
AU1965500A (en) | 2000-06-05 |
IL142912A0 (en) | 2002-04-21 |
DE59906902D1 (de) | 2003-10-09 |
PL348187A1 (en) | 2002-05-06 |
HUP0105063A2 (hu) | 2002-04-29 |
MA25264A1 (fr) | 2001-10-01 |
WO2000028822A2 (de) | 2000-05-25 |
NO20012386D0 (no) | 2001-05-15 |
TR200101359T2 (tr) | 2001-11-21 |
NO20012386L (no) | 2001-05-15 |
ZA200104913B (en) | 2002-08-28 |
ATE248834T1 (de) | 2003-09-15 |
ID28945A (id) | 2001-07-19 |
BG105519A (en) | 2002-01-31 |
EP1131319A2 (de) | 2001-09-12 |
BR9915370A (pt) | 2001-08-14 |
US6624119B1 (en) | 2003-09-23 |
AR031062A1 (es) | 2003-09-10 |
EA200100523A1 (ru) | 2001-10-22 |
EP1131319B1 (de) | 2003-09-03 |
CZ20011711A3 (cs) | 2002-02-13 |
SK6722001A3 (en) | 2001-12-03 |
WO2000028822A3 (de) | 2000-11-16 |
CA2351564A1 (en) | 2000-05-25 |
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