CN1196353A - 哒嗪-3-酮衍生物及其应用 - Google Patents
哒嗪-3-酮衍生物及其应用 Download PDFInfo
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- CN1196353A CN1196353A CN98107744A CN98107744A CN1196353A CN 1196353 A CN1196353 A CN 1196353A CN 98107744 A CN98107744 A CN 98107744A CN 98107744 A CN98107744 A CN 98107744A CN 1196353 A CN1196353 A CN 1196353A
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- Prior art keywords
- alkenyl
- alkyl
- carbonyl
- hydrogen
- pyridazin
- Prior art date
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 45
- 229910052736 halogen Chemical group 0.000 claims abstract description 23
- 150000002367 halogens Chemical group 0.000 claims abstract description 23
- 239000001301 oxygen Substances 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 741
- -1 4Be hydrogen Chemical class 0.000 claims description 67
- 241000196324 Embryophyta Species 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 241001597008 Nomeidae Species 0.000 claims description 32
- 150000001721 carbon Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000005864 Sulphur Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 33
- 239000004009 herbicide Substances 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
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- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
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- 101150065749 Churc1 gene Proteins 0.000 description 42
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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- 241000192043 Echinochloa Species 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
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- 238000012360 testing method Methods 0.000 description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000013375 chromatographic separation Methods 0.000 description 8
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- 231100000674 Phytotoxicity Toxicity 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000012752 auxiliary agent Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 description 1
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 description 1
- KZENFXVDPUMQOE-UHFFFAOYSA-N ethyl 2-(triphenyl-$l^{5}-phosphanylidene)propanoate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C(C)C(=O)OCC)C1=CC=CC=C1 KZENFXVDPUMQOE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
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- 229940031815 mycocide Drugs 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
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- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
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- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 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
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 235000009165 saligot Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 229940001516 sodium nitrate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 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
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明提供了新的通式(1)的哒嗪-3-酮衍生物,其中R1是卤代烷基;R2和R3独立地是氢、烷基、卤代烷基或烷氧基烷基;X是氢或卤素;Y是卤素、硝基、氰基或三卤代甲基;Z1是氧、硫、CH2或NH;R4是氢、卤素、或烷基,和R5是环烷基、甲酰基、苄基、带有环氧基的烷基,或其它如说明书所定义的取代基;以及含有以该化合物为活性成分的除草剂。
Description
发明领域
本发明涉及具有优异除草活性的哒嗪-3-酮衍生物及其应用。
发明概述
本发明人广泛地致力于寻找具有优异除草活性的化合物,结果,发现如下所述的通式(1)哒嗪-3-酮衍生物具有优异的除草活性,从而完成了本发明。
R2和R3相同或不同,独立地是氢、C1-C3烷基、C1-C3卤代烷基或C1-C3烷氧基C1-C3烷基;
X是氢或卤素;
Y是卤素、硝基、氰基或三卤代甲基;
Z2是氧、硫、CH2或NH;
R4是氢、卤素或C1-C6烷基;以及
R5是C3-C8环烷基、甲酰基、苄基、带有环氧基的C2-C10烷基、C3-C8环烷基C1-C6烷基、甲酰基C1-C6烷基、C3-C8环烷基C2--C6链烯基、甲酰基C2--C6链烯基、在同一碳原子上被OR6和OR7取代的C1-C6烷基、在同一碳原子上被OR6和OR7取代的C2--C6链烯基、在同一碳原子上被SR6和SR7取代的C1-C6烷基、在同一碳原子上被SR6和SR7取代的C2--C6链烯基、羧基C2--C6链烯基、(C1-C8烷氧基)羰基C2--C6链烯基、(C1-C6卤代烷氧基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷氧基}羰基C2--C6链烯基、(C3-C8环烷氧基)羰基C2--C6链烯基、(C1-C6烷基)羰基C2--C6链烯基、(C1-C6卤代烷基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷基}羰基C2--C6链烯基或(C3-C8环烷基)羰基C2--C6链烯基;
R6和R7相同或不同,各自独立地是C1-C6烷基或C1-C6卤代烷基,或者R6和R7一起形成被卤素选择取代的亚乙基、被卤素选择取代的三亚甲基、被卤素选择取代的四亚甲基、被卤素选择取代的五亚甲基或被卤素选择取代的亚乙基氧基亚乙基;
本发明还提供了含有上述化合物作为活性成分的除草剂。发明的详细描述
本发明化合物的具体实例如下:
哒嗪-3-酮衍生物,其中Z1是氧、硫或NH;以及R5是甲酰基、甲酰基C1-C6烷基、甲酰基C2--C6链烯基、在同一碳原子上被OR6和OR7取代的C1-C6烷基、在同一碳原子上被OR6和OR7取代的C2--C6链烯基、在同一碳原子上被SR6和SR7取代的C1-C6烷基、在同一碳原子上被SR6和SR7取代的C2--C6链烯基、(C1-C6烷基)羰基C2--C6链烯基、(C1-C6卤代烷基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷基}羰基C2-C6链烯基或(C3-C8环烷基)羰基C2--C6链烯基;R6和R7相同或不同,各自独立地是C1-C6烷基或C1-C6卤代烷基;
哒嗪-3-酮衍生物,其中R1是三氟甲基,R2是甲基或氢,R3是氢,X是氟,Y是氯,R4是氢,以及R5是C3-C8环烷基、苄基、带有环氧基的C2-C10烷基、C3-C8环烷基C1-C6烷基、C3-C8环烷基C2--C6链烯基、在同一碳原子上被OR6和OR7取代的C1-C6烷基、在同一碳原子上被OR6和OR7取代的C2--C6链烯基、在同一碳原子上被SR6和SR7取代的C1-C6烷基、在同一碳原子上被SR6和SR7取代的C2-C6链烯基、羧基C2--C6链烯基、(C1-C8烷氧基)羰基C2--C6链烯基、(C1-C6卤代烷氧基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷氧基)羰基C2--C6链烯基或(C3-C8环烷氧基)羰基C2--C6链烯基,R6和R7一起形成亚乙基、三亚甲基、四亚甲基、五亚甲基或亚乙基氧基亚乙基;
哒嗪-3-酮衍生物,其中R1是三氟甲基,R2是甲基或氢,R3是氢,X是氟,Y是氯,R4是氢,R5是C3-C8环烷基、带有环氧基的C2-C10烷基、(C1-C8烷氧基)羰基C2--C6链烯基或在同一碳源子上被OR6和OR7取代的C1-C6烷基,R6和R7一起形成亚乙基或三亚甲基;
哒嗪-3-酮衍生物,其中R1是三氟甲基,R2是甲基或氢,R3是氢,X是氟,Y是氯,R4是氢,和R5是C3-C8环烷基;
哒嗪-3-酮衍生物,其中Z1是氧;
哒嗪-3-酮衍生物,其中Y是卤素,R1是三氟甲基,R2是氢或甲基,R3是氢,和R4是氢或甲基;
哒嗪-3-酮衍生物,其中X是氟;
哒嗪-3-酮衍生物,其中Z1是氧、硫或NH;
哒嗪-3-酮衍生物,其中R4是氢;和
哒嗪-3-酮衍生物,其中R5是甲酰基或在同一碳原子上被OR6和OR7取代的C1-C6烷基,R6和R7相同或不同,各自独立地是C1-C6烷基或C1-C6卤代烷基。
X和Y表示的卤素可以包括氯、氟和溴。
Y表示的三卤代甲基可包括三氟甲基。
R1表示的C1-C3卤代烷基可包括三氟甲基、一氯二氟甲基和五氟乙基。
R2或R3表示的C1-C3烷基可包括甲基、乙基和异丙基。
R2或R3表示的C1-C3卤代烷基可包括三氯甲基、三氟甲基、二氟甲基、一氯二氟甲基和五氟乙基。
R2或R3表示的C1-C3烷氧基C1-C8烷基可包括甲氧基甲基。
R4表示的C1-C6烷基可包括甲基、乙基、丙基、丁基和正戊基。
R4表示的卤素可包括氯、氟和溴。
R5表示的C3-C8环烷基可包括环丙基、环丁基、环戊基和环己基。
R5表示的带有环氧基的C2-C10烷基可包括1,2-环氧乙基、1,2-环氧丙基、2,3-环氧丙基和3,4-环氧丁基。
R5表示的C3-C8环烷基C1-C6烷基可包括环丙基甲基、2-(环丙基)乙基、环丁基甲基、环戊基甲基和环己基甲基。
R5表示的甲酰基C1-C6烷基可包括甲酰基甲基、2-甲酰基乙基和3-甲酰基丙基。
C3-C8环烷基C2--C6链烯基可包括2-(环丙基)乙烯基、3-(环丙基)-1-丙烯基和3-环丁基-1-丙烯基。
R5表示的甲酰基C2--C6链烯基可包括2-甲酰基乙烯基和2-甲酰基-1-丙烯基。
R5表示的在同一碳原子上被OR6和OR7取代的C1-C6烷基可包括二甲氧基甲基、二乙氧基甲基、二丙氧基甲基、亚乙二氧基甲基、三亚甲二氧基甲基、2,2-二甲氧基乙基、2,2-二乙氧基乙基、2,2-亚乙二氧基乙基、2,2-三亚甲二氧基乙基、3,3-二甲氧基丙基、3,3-二乙氧基丙基、3,3-亚乙二氧基丙基和3,3-三亚甲二氧基甲基。
R5表示的在同一碳原子上被OR6和OR7取代的C2--C6链烯基可包括3,3-二甲氧基-1-丙烯基和3,3-二乙氧基-1-丙烯基。
R5表示的在同一碳原子上被SR6和SR7取代的C1-C6烷基可包括二(甲硫基)甲基、二(乙硫基)甲基、二(丙硫基)甲基、亚乙二硫基甲基、三亚甲二硫基甲基、2,2-二(甲硫基)乙基、2,2-二(乙硫基)乙基、2,2-亚乙基二硫基乙基、2,2-三亚甲二硫基乙基、3,3-二(甲硫基)丙基、3,3-二(乙硫基)丙基、3,3-亚乙二硫基丙基和3,3-三亚甲二硫基甲基。
R5表示的在同一碳原子上被SR6和SR7取代的C2--C6链烯基可包括3,3-二甲硫基-1-丙烯基和3,3-二乙氧硫-1-丙烯基。
R5表示的羧基C2--C6链烯基可包括2-羧基乙烯基和2-羧基-1-丙烯基。
R5表示的(C1-C8烷氧基)羰基C2--C6链烯基可包括2-甲氧羰基乙烯基、2-乙氧羰基乙烯基、2-丙氧羰基乙烯基、2-异丙氧羰基乙烯基、2-甲氧羰基-1-丙烯基、2-乙氧羰基-1-丙烯基、2-丙氧羰基-1-丙烯基和2-异丙氧羰基-1-丙烯基。
R5表示的(C1-C6卤代烷氧基)羰基C2--C6链烯基可包括2-氯-2-乙氧羰基乙烯基。
R5表示的{(C1-C4烷氧基)C1-C4烷氧基}羰基C2--C6链烯基可包括2-甲氧基甲氧基羰基乙烯基和2-甲氧基甲氧基羰基-1-丙烯基。
R5表示的(C3-C8环烷氧基)羰基C2--C6链烯基可包括2-环丙氧羰基乙烯基、2-环丁氧羰基乙烯基、2-环戊氧羰基乙烯基、2-环丙氧羰基-1-丙烯基、2-环丁氧羰基-1-丙烯基和2-环戊氧羰基-1-丙烯基。
R5表示的(C1-C6烷基)羰基C2--C6链烯基可包括2-甲基羰基乙烯基。
R5表示的(C1-C6卤代烷基)羰基C2--C6链烯基可包括2-氯甲基羰基乙烯基。
R5表示的{(C1-C4烷氧基)C1-C4烷基}羰基C2--C6链烯基可包括2-(2-甲氧基乙基)羰基乙烯基。
R5表示的(C3-C8环烷基)羰基C2--C6链烯基可包括2-环丙基羰基乙烯基。
就除草活性而言,本发明化合物中优选取代基的实例如下:
X是氟、氯和氢,特别是氟;
Y是氯;
R1是CF2J,其中J是氢、氟、氯或三氟甲基,更优选三氟甲基;
R2是甲基和氢;
R3是甲基和氢;以及
R4是甲基和氢。
本发明化合物中特别优选的实例是具有下述定义的化合物:R1是三氟甲基,R2是甲基或氢,R3是氢,X是氟,Y是氯,Z1是氧,R4是氢以及R5是下式基团:
由于存在着双键,本发明化合物可能有几何异构体;由于至少有一个不对称碳原子存在,本发明可能有旋光异构体。当然,所有这些几何异构体和旋光异构体都包括在本发明的范围之内。
通过例如如下所述的制备方法1至3可制备本发明化合物。
(制备方法1)
此制备方法根据下述流程1进行:流程1其中X、Y、R1、R2、R3、R4和R5如上文定义,Z2是氧、硫或NH。
上述步骤的反应条件例举如下:
化合物[II]可用下述方法制备:必要时在碱的存在下,使化合物[I]与下述通式化合物反应:
CHZ(R4)R5其中Z是溴、氯、碘、甲磺酰氧基、三氟甲基磺酰氧基或对甲苯磺酰氧基,R4和R5如上文定义。
上述反应可在没有溶剂或在溶剂中完成。反应温度通常在-20℃至150℃的范围内。反应时间通常在瞬时至72小时的范围内。相对于1摩尔化合物[I],反应中所用试剂的量为1摩尔化合物CHZ(R4)R5,和必要时用1摩尔碱,该比例为化学计量比,根据反应条件可随意改变。
可用的溶剂包括指族烃,例如己烷、环己烷和石油醚;芳香烃,例如苯、甲苯和二甲苯;醚,例如二乙醚、1,4-二噁烷和四氢呋喃(下文称作THF);酰胺,例如甲酰胺和N,N-二甲基甲酰胺;叔胺,例如吡啶、三乙胺和N,N-二甲基苯胺;硫化合物,例如二甲基亚砜和sulforane;和它们的混合物。
必要时可用的碱可包括无机碱,如碳酸氢钠、碳酸氢钾、碳酸钠、碳酸钾、氢氧化钠、氢氧化钾、氢化钠和氢化钾;有机碱,如三乙胺、二异丙基乙胺、吡啶、4-二甲氨基吡啶、甲基吡啶和N,N-二甲基苯胺;和它们的混合物。
必要时,反应还涉及碘化合物,如碘化钠或碘化钾。
反应完成后,通过过滤收集生成的晶体(必要时通过加水来沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。
(制备方法2)
此方法根据下述流程2进行:流程2其中X、Y、R1、R2、R3、R4和Z2定义如上,R5-2是C2-C7链烯基,R5-3是R5-2的双键氧化裂解成为酮或醛部分后得到的取代基,例如甲酰基或甲酰基C1-C6烷基,R5-4是用醇或硫醇把酮或醛部分转化成缩醛或硫代缩醛部分后得到的取代基,即在同一碳原子上被OR6和OR7取代的C1-C6烷基或在同一碳源子上被SR6和SR7取代的C1-C6烷基,其中R6和R7如上文定义。
上述各步骤的反应条件例举如下:
由化合物[I]制备[IV]的步骤
化合物[IV]可按照制备方法1所述制备。
由化合物[IV]制备化合物[V]的步骤
将化合物[IV]先用臭氧(臭氧用发生器制备),再用还原剂处理可制备化合物[V]。
反应在溶剂中进行。反应温度通常在-78℃至-40℃的范围内。反应时间通常在瞬时至6小时的范围内。
可用的溶剂包括脂族烃,例如己烷、环己烷和石油醚;卤代烃,例如二氯甲烷、氯仿和1,2-二氯乙烷;芳香烃,例如苯、甲苯和二甲苯;酮,例如丙酮、甲乙酮、甲基异丁基酮和环己酮;酯,例如甲酸甲酯、乙酸乙酯和碳酸二乙酯;醇,例如甲醇、乙醇、异丙醇和丁醇;以及它们的混合物。
可用的还原剂包括金属,例如锌;二硫化物,例如甲硫醚、乙硫醚或丁硫醚;亚磷酸酯,例如亚磷酸三甲酯、亚磷酸三乙酯或亚磷酸三丁酯;三芳基膦,例如三苯膦;三烷基膦,例如三丁膦。
相对于1摩尔原料化合物[IV]所用还原剂的量通常是1摩尔至过量。
使化合物[IV]与四氧化锇或过氧化钠反应也可制得化合物[V]。
反应在溶剂中进行。反应温度通常在0℃至60℃的范围内。反应时间通常在瞬时至24小时的范围内。
可用的溶剂包括卤代烃,例如二氯甲烷、氯仿和1,2-二氯乙烷;醚,例如1,4-二噁烷、THF或乙醚;酮,例如丙酮、甲乙酮、甲基异丁基酮和环己酮;酯,例如甲酸甲酯、乙酸乙酯和碳酸二乙酯;醇,例如甲醇、乙醇、异丙醇和丁醇;以及它们的混合物。
相对于1摩尔化合物[IV]所用四氧化锇的量通常是催化剂量至1摩尔。相对于1摩尔化合物[IV]所用过氧化钠的量通常是1至10摩尔。
反应完成后,通过过滤收集生成的晶体(必要时通过加水沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。
由化合物[V]制备化合物[VI]的步骤
在酸催化剂的存在下,使化合物[V]与相应的醇(下述通式化合物:R6OH、R7OH,或HO-R6-R7-OH,其中R6和R7如上文定义,例如甲醇、乙醇、乙二醇和1,3-丙二醇)或硫醇(下述通式化合物:R6SH、R7SH,或HS-R6-R7-SH,其中R6和R7如上文定义)反应形成缩醛或硫缩醛可制备化合物[VI]。
反应在有或没有溶剂的情况进行。反应时间通常在瞬时至48小时的范围内。相对于1摩尔化合物[V]所用醇或硫醇的量为1摩尔至大大过量。
可用的溶剂包括脂族烃,例如己烷、环己烷和石油醚;芳香烃,例如苯、甲苯和二甲苯;卤代烃,例如二氯甲烷、氯仿和1,2-二氯乙烷;以及它们的混合物。
可用的酸催化剂包括磺酸,例如对甲苯磺酸、苯磺酸、甲磺酸或三氟甲磺酸;无机酸,例如硫酸、盐酸或氢溴酸;路易斯酸,例如氯化锌和三氟化硼-乙醚复合物;以及它们的混合物。
酸催化剂的用量相对于1摩尔化合物[V]为催化剂量至5摩尔的范围内。
反应完成后,通过过滤收集生成的晶体(必要时通过加水沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。
(制备方法3)
此方法根据下述流程3进行:流程3其中X、Y、R1、R2、R3、R4和Z2定义如上,R5-5是C2-C10链烯基,以及R5-6是带有环氧基的C2-C10烷基。
按照制备方法1所描述的方法可制备化合物[VII]。
在有或没有碱存在的条件下用氧化剂处理化合物[VII]可制得化合物[VIII]。
该反应在溶剂中进行。反应温度通常在-20℃至50℃的范围内。反应时间通常在瞬时至48小时的范围内。
可用的溶剂包括卤代烃,例如二氯甲烷、氯仿和1,2-二氯乙烷;醇,例如甲醇、乙醇、异丙醇和丁醇;苯;水;以及它们的混合物。
可以使用的碱包括氢氧化钠、碳酸氢钠、碳酸氢钾、碳酸钠、碳酸钾和三叔丁氧基铝。
可以使用的氧化剂包括过氧化氢、间氯过苯甲酸、三氟过乙酸、过乙酸、叔丁基化过氧氢和高亚氯酸钠。
相对于1摩尔化合物[VII]所用氧化剂的量通常是1至50摩尔。相对于1摩尔化合物[VII]所用碱的量通常是0.1至5摩尔。
反应完成后,通过过滤收集生成的晶体(必要时通过加水沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。
下面描述在本发明化合物的制备中使用的原料化合物的制备方法。
在上述流程中的表示为化合物[IX]的苯胺衍生物是现有技术中公知的,例如,见欧洲专利申请的公开说明书EP-61741-A,或者可以按照其中公开的方法制备。由化合物[IX]制备化合物[X]的步骤
化合物[X]可由化合物[IX]制得,例如,根据下述流程5(参见OrganicSynthesis Collective,第1卷,第442页)制备。流程5其中X、Y和Z0定义如上。由化合物[X]制备化合物[XI]的步骤
化合物[XI]可按下述方法制备:在碱存在下,使下述通式的α-二卤代化合物:
R1C(=O)CV2R3其中R1和R3定义如上,以及V是碘、溴或氯,与水进行反应得到下述通式的羰基衍生物(下文称作反应1):
R1C(=O)C(=O)R3其中R1和R3定义如上;然后使该羰基衍生物与肼衍生物[X]反应(下文称作反应2)。上述羰基衍生物R1C(=O)C(=O)R3还可在水中以水合物的形式或在醇中以缩醛衍生物的形式进行反应。
反应1通常在溶剂(例如水)中进行。反应温度通常在0℃至100℃的范围内。反应时间通常在瞬时至72小时的范围内。相对于1摩尔α-二卤代化合物R1C(=O)CV2R3,反应中所用试剂的量为2摩尔水和2摩尔碱(例如乙酸钠),该比例为化学计量比,但是根据反应条件可随意变化。
反应2通常在溶剂(例如THF)中进行。反应温度通常在0℃至100℃的范围内。反应时间通常在瞬时至72小时的范围内。相对于1摩尔反应1所用α-二卤代化合物,反应中所用肼衍生物[X]的量为1摩尔,该比例为化学计量比,但根据反应条件可随意变化。所述肼衍生物[X]还可以盐(例如盐酸盐或硫酸盐)的形式使用。
反应完成后,通过过滤收集生成的晶体(必要时通过加水来沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。由化合物[XI]制备化合物[XII]的步骤
通过使化合物[XI]与下式化合物反应可制得化合物[XII]:
Ph3P=C(R2)COOC2H5其中R2定义如上和Ph是苯基。
上述化合物Ph3P=C(R2)COOC2H5是市售的,或可按照例如在“Jikken KagakuKoza”(Maruzen Kabushiki Kaisha出版),第四版,第24卷,第259-260页所述的方法制备。
该反应通常在溶剂(例如THF)中进行。反应温度通常在-20℃至150℃的范围内。反应时间通常在瞬时至72小时的范围内。相对于1摩尔化合物[XI]反应中所用化合物Ph3P=C(R2)COOC2H5的量为1摩尔,该比例为化学计量比,但可根据反应条件随意变化。
反应完成后,通过过滤收集生成的晶体(必要时通过加水来沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。
按照由化合物[XIII]制备化合物[XII](流程4)相同的方式可制得化合物[XIV]。由化合物[XIV]制备化合物[XV]的步骤
通过硝化化合物[XIV]可制得化合物[XV]。该反应通常在溶剂中进行。反应温度通常在-10℃至室温的范围内。反应时间通常在瞬时至72小时的范围内。
硝化剂可包括硝酸和发烟硝酸。相对于1摩尔化合物[XIV]反应中所用硝化剂的量为1摩尔,该比例为化学计量比,但可根据反应条件随意改变。
反应中所用溶剂可包括脂族烃,例如己烷、环己烷和石油醚;醚,例如乙醚、1,4-二噁烷和THF;酸,例如硫酸和乙酸;及其混合物。
反应完成后,通过过滤收集生成的晶体(必要时通过加水来沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。由化合物[XV]制备化合物[XVI]的步骤
通过用金属,例如铁还原化合物[XV]可制得化合物[XVI]。
该反应通常在酸存在的溶剂中进行。反应温度的范围通常在室温至加热回流温度。反应时间通常在瞬时至72小时的范围内。
还原剂可包括铁、锌和锡。相对于1摩尔化合物[XV]反应中所用还原剂的量通常为3摩尔至大大过量,该比例为化学计量比,但可根据反应条件随意改变。
反应中可用的溶剂包括脂族烃,例如己烷、环己烷和石油醚;芳香烃,例如苯、甲苯和二甲苯;醚,例如乙醚、1,4-二噁烷和THF;酯,例如甲酸乙酯、乙酸乙酯和碳酸二乙酯;腈,例如乙腈和苄腈;水;及其混合物。
可用的酸可包括乙酸、盐酸和硫酸。
反应完成后,通过过滤收集生成的晶体(必要时通过加水来沉积),或对反应混合物进行通常的后处理,例如用有机溶剂萃取和浓缩。必要时,可通过色谱分离或重结晶技术进一步纯化;从而分离出目的化合物。
本发明化合物具有优异的除草活性,并可在作物和杂草间显示出优异的选择性。
例如,本发明化合物对下文所例举的各种杂草具有除草活性,这些杂草在以往的叶面处理和旱田土壤处理中存在困难。
蓼科杂草:
卷茎蓼(Polygonum convolvulus),酸模叶蓼(Polygonumlapathifolium),宾洲蓼(Polygonum pensylvanicum),春蓼(Polygonumpersicaria),皱叶酸模(Rumex crispus),钝叶酸模(Rumex obtusifolius),虎杖(Polygonum cuspidatum)马齿苋科杂草:
马齿苋(Portulaca oleracea)石竹科杂草:
繁缕(Stellaria media)藜科杂草:
藜(Chenopodium album),扫帚菜(Kochia scoparia)苋科杂草:
西风谷(Amaranthus retroflexus),绿穗苋(Amaranthus hybridus)Cruiferous(brassicaceous)杂草:
野生萝卜(Raphanus raphanistrum),野生芥末(Sinapis arvensis),荠菜(Capsella bursa-pastoris),豆科(fabaceous)杂草:
高田菁(Sesbania exaltata),加拿大筛子芥(Cassia obtusifolia),扭曲山马蝗(Desmodium tortuosum),白车轴草(trifolium repens)锦葵科杂草:
青麻(Abutilon theophrasti),刺黄花稔(Sida spinosa)堇菜科杂草:
田堇菜(Viola arvensis),三色堇(Viola tricolor)茜草科杂草:
猪殃殃(Galium aparine)旋花科杂草:
裂叶牵牛(Ipomoea hederacea),圆叶牵牛(Ipomoea purpurea),全叶裂叶牵牛(Ipomoea hederacea var.integriuscula),多洼牵牛(Ipomoealacunosa),田旋花(Convolvulus arvensis)唇形科杂草:
小野芝麻(Laminum purpureum),宝盖草(Lamium amplexicaule)茄科杂草:
曼陀罗(Datura stramonium),龙葵(Solanum nigrum)玄参科杂草:
波斯水苦苣(Veronica persica),常春藤叶婆婆纳(Veronicahederaefolia)菊科杂草:
宾州苍耳(Xanthium pensylvanicum),向日葵(Helianthus annuus),淡甘菊(Matricaria perforata or inodora),珍珠菊(Chrysanthemum segetum),香甘菊(Matricaria matricarioides),美洲豚草(Ambrosiaartemisiifolia),三裂叶豚草(Ambrosia trifida),加拿大飞蓬(Erigeroncanadensis),蒌蒿(Artemisia princeps),极高一枝黄花(Solidagoaltissima)紫草科杂草:
田野勿望草(Myosotis arvensis)萝摩科杂草:
叙利亚马利筋(Asclepias syriaca)大戟科杂草:
泽漆(Eurphorbia helioscopia),美洲地锦草(Euphorbia maculata)禾本科杂草:
稗草(Echinochla crus-galli),狗尾草(Setaria viridis),费氏狗尾草(Setaria faberi),马唐(Digitaria sanguinalis),牛筋草(Eleusineindica),早熟禾(Poa annua),看麦娘(Aloecurus myosuroides),野燕麦(Avenafatua),阿刺伯高粱(Sorghum halepense),匍匐冰草(Agropyron repens),旱雀麦(Bromus tectorum),狗牙根(Cynodon dactylon),秋稷(Panicumdichotomiflorum),得克萨斯稷(Panicum texanum),二色蜀黍(Sorghumvulgare)鸭跖草科杂草:
鸭跖草(Commelina communis)木贼科杂草:
问荆(Equisetum arvense)莎草科杂草:
碎米莎草(Cyperus iria),香附子(Cyperus rotundus),铁荸荠(Cyperusesculentus)
此外,本发明的一些化合物对主要农作物,园艺作物(如花和观赏植物)和菜蔬类作物无明显的植物毒性;其中的主要农作物如玉米(Zea mays),小麦(Triticum aestivum),大麦(Hordeum vulgare),稻(Oryza sativa),高粱(Sorghum bicolor),大豆(Glycine max),棉花(Gossypium spp.),甜菜(Betavulgaris),花生(Arachis hypogaea),向日葵(Helianthus annuus)和蔓菁(Brassica napus)。
此外,本发明化合物能够有效控制铲隙法栽植的大豆(Glycine max)、玉米(Zea mays)、小麦(Triticum aestivum)和其它作物间的各种有害杂草,并且,某些本发明化合物还显示出对作物无明显的植物毒性。
本发明化合物在水田漫灌处理情况下对如下文所列的各种有害杂草具有除草活性。禾本科杂草:
稗(Echinochloa oryzicola)玄参科杂草:
陌上草(Lindernia procumbens)千屈菜科杂草:
节节菜(Rotala indica),多花水苋(Ammannia multiflora)沟繁缕科杂草:
三蕊沟繁缕(Elatine triandra)莎草科杂草:
异型莎草(Cyperus difformis),萤蔺(Scirpus juncoides),牛毛毡(Eleocharis acicularis),水莎草(Cyperus serotinu),木贼状荸荠(Eleocharis kuroguwai)雨久花科杂草:
鸭舌草(Monochoria vaginalis)泽泻科杂草:
矮慈茹(Sagittaria pygaea),慈茹(Sagittaria trifolia),窄叶泽泻(Alisma canaliculatum)眼子菜科杂草:
眼子菜(Potamogeton distinctus)伞形科杂草:
水芹(Oenanthe javanica)
此外,本发明一些化合物对移植的水稻无明显的植物毒性。
本发明化合物能够有效控制果园、草地、空地、森林、排水沟、水道或其它非栽培地中的各种有害杂草。
本发明还对例如生长在排水沟、水道等地方的各种水生植物〔如风眼兰(Eichhornia crassipes)〕具有除草活性。
本发明化合物与国际专利申请WO95/34659公开的说明书中所述的除草化合物有着基本相同的特性。在栽培通过引入公开说明书所述的除草耐受性基因而获得具有耐受性的作物时,可使用比栽培无耐受性的常规作物所用施用量大得多的本发明化合物,因此能够更有效地防治其它有害植物。
当本发明化合物用作除草剂的活性成分时,通常将它们与固体或液体载体或稀释剂、表面活性剂和其它助剂混合配制成诸如乳油、可湿性粉剂、悬浮剂、颗粒剂、浓乳剂、水分散性颗粒剂,或其它制剂。
这些制剂可含有任一种本发明化合物作为活性成分,其用量按制剂总重量计为0.001-80%,优选0.005%-70%。
可使用的固体载体或稀释剂包括细粉或颗粒状的下述物质:矿物质,如高岭土、硅镁土、膨润土、酸性粘土、叶蜡石、滑石、硅藻土和方解石;有机物质,如胡桃核粉;水溶性有机物质,如尿素;无机盐,如硫酸铵;和合成水合氧化硅。可使用的液体载体或稀释剂包括芳香烃类,如甲基萘、苯基二甲苯基乙烷和烷基苯(如二甲苯);醇类,如异丙醇、乙二醇和2-乙氧基乙醇;酯类,如邻苯二甲酸二烷基酯;酮类,如丙酮、环己酮和异佛尔酮;矿物油,如机油;植物油,如豆油和棉籽油;二甲基亚砜,N,N-二甲基甲酰胺,乙腈,N-甲基吡咯烷酮和水等。
用于乳化、分散或扩散的表面活性剂可包括阴离子型表面活性剂,如烷基硫酸盐、烷基磺酸盐、烷芳基磺酸盐、磺基琥珀酸二烷基酯和聚氧乙烯烷基芳基醚的磷酸盐;和非离子型的表面活性剂,如聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯聚氧丙烯嵌段共聚物、脱水山梨糖醇脂肪酸酯和聚氧乙烯脱水山梨糖醇脂肪酸酯。
助剂的实例可包括木质素磺酸盐、藻酸盐、聚乙烯醇、阿拉伯胶、羧甲基纤维素(CMC)和磷酸异丙基酯(PAP)。
通常将本发明化合物配制成上述制剂,然后用于芽前或芽后经土壤、叶面或漫灌处理有害杂草。土壤处理包括土壤表面处理和拌土。叶面处理包括施用于植物整体和直接施用,直接施用是将化学品仅施用于杂草而不接触作物。
当把本发明化合物与其它除草剂混合使用时,本发明化合物常常使除草活性增强。本发明化合物可与杀虫剂、杀螨剂、杀线虫剂、杀真菌剂、杀菌剂、植物生长调节剂、肥料和土壤调节剂制成混合物使用。
可与本发明化合物形成上述混合物的除草剂的实例为阿特拉津,草净津,二甲丙乙净,嗪草酮,扑草净,西马津,西草净,氯麦隆,敌草隆,dymrone,伏草隆,异丙隆,利谷隆,甲基苯噻隆,溴苯腈,碘苯腈,乙丁烯氟灵,胺硝草,氟乐灵,氟锁草醚,氟锁草醚钠,甲羧除草醚,甲氧除草醚,氟黄胺草醚,克阔乐,草酮,氟硝草醚,carfentrazon-ethyl,flumiclorac-pentyl,flumioxazine,fluthiacet-methyl,sulfentrazone,thidiazimin,azafenidin,pyraflufen-ethyl,双苯唑快,敌草快,百草枯,2,4-D,2,4-D丁酸,氯酞酸甲酯,二甲四氯,二甲四氯丙酸,稗草胺,二氯吡啶酸,麦草畏,氟硫草定,氟草烟,二甲四氯丙酸盐,萘丙胺,二甲四氯乙硫酯,二氯喹啉酸,绿草定,thiazopyr,乙草胺,甲草胺,丁草胺,乙酰甲草胺,乙基乙草胺,丙草胺,扑草胺,苄嘧黄隆,氯黄隆,氯嘧黄隆,halosulfuron-methyl,甲磺隆,烟嘧磺隆,氟嘧磺隆,吡嘧磺隆,嘧磺隆,噻苯隆,醚苯黄隆,苯磺隆,磺隆,azimsulfuron,cloransulam-methyl,cyclosulfamuron,flumetsulam,flupyrsulfuron,啶嘧磺隆,imazosulfuron,metosulam,diclosulam,prosulfuron,rimsulfuron,triflusulfuron-methyl,ethoxysulfuron,sulfosulfuron,咪草酯,灭草烟,灭草喹,咪草烟,咪草酯,imazamox,bispyribac-sodium,pyriminobac-methyl,pyrithiobac-sodium,枯杀达,烯草酮,噻草酮,肟草酮,禾草灵,唑禾草灵-乙酯,高唑禾草灵,吡氟禾草灵,高吡氟禾草灵,吡氟氯禾灵,喹禾灵,cyhalofop-butyl,clodinafop-propargyl,吡草酮,异草胺,吡氟草胺,达草灭,吡唑特,苄草唑,呋草酮,isoxaflutole,sulcotrione,草铵膦,草甘膦,噻草平,杀草丹,溴丁酰草胺,抑草磷,丁草特,哌草丹,dimethenamid,甲胂钠,扑草灭,禾草畏,异草胺,苯噻草胺,草达灭,甲肾一钠,哌草磷,pyributicarb,敌稗,哒草特,野麦畏,cafenstrol,胺草唑,fluthiamide,diflufenzopyr,triaziflam,pentoxazone,epoprodam,metobenzuron和oxaziclomefon。
对上述化合物的描述见农业化学品手册目录(Catalog of Farm ChemicalHandbook)1995版(Meister Publishing Company出版);农药新化合物综述(AGCHEM NEW COMPOUND REVIEW),13或15卷,1995年(AG CHEM INFORMATIONSERVICE出版);“Josouzai Kenkyu Souran”(Hakuyu-sha出版);或除草剂手册(HERBICIDE HANDBOOK),第7版(Weed Science Society of America出版)。
下面描述这类组合混用的代表性实例,其中本发明化合物用下表1指出的各化合物编号表示。
1.选自268、269、271、272、274、291、294、295和327中的任意一种化合物和选自莠去净、草津浸、麦草畏、flumetsulam、halosulfuron-methyl和isoxaflutole中的任一种化合物以1∶0.05-1000的重量比混合。
2.选自化合物268、269、271、272、274、291、294、295和327中的任一种化合物与选自乙基乙草胺、乙草胺、dimethenamid、胺硝草和fluthiamid的任一种化合物以1∶0.1-1000的重量比混合。
3.选自化合物268、269、271、272、274、291、294、295和327的任一种化合物与选自cotoran、敌草隆和norflurazon的任一种化合物以1∶0.05-1000的重量比混合。
4.选自化合物268、269、271、272、274、291、294、295和327的任一种化合物与选自异丙隆和绿草隆的任一种化合物以1∶0.1-1000的重量比混合。
5.选自化合物268、269、271、272、274、291、294、295和327的任一种化合物与选自二甲四氯丙酸盐、甲磺隆、2,4-D、溴苯腈和碘苯腈的任一种化合物以1∶0.05-1000的重量比混合。
6.选自化合物268、269、271、272、274、291、294、295和327的任一种化合物与选自吡氟草胺、甲磺隆、唑禾草灵-乙酯和clodinafop-propargyl的任一种化合物以1∶0.001-100的重量比混合。
当本发明化合物用作除草剂的活性成分时,其施用量通常为每公顷0.01-10,000g,优选1-8000g,当然该用量可以依据气候条件、制剂类型、施用时间、施用方法、土壤状况、需保护的作物种类、需防治的杂草种类等而变化。在使用乳油、可湿性粉剂、悬浮剂、浓乳剂、水分散性颗粒剂或其它类似剂型时,一般是在加水稀释后以每公顷大约10-1000升的预定量施用(必要时,可以加入诸如分散剂之类的助剂)。在使用颗粒剂或某些类型的悬浮剂时,一般不需要任何稀释而直接施用。
必要时,除上述表面活性剂外,还可使用的助剂包括聚氧乙烯树脂酸(酯)、木质素磺酸盐、松香酯、甲二磺酸二萘基酯、作物油浓缩物和植物油,如豆油、玉米油、棉子油和葵花籽油。
本发明化合物还可用作收获助剂的活性成分,上述助剂如用于棉花(Gossipyum spp.)的脱叶剂和干燥剂,以及马铃薯(Solanum tuberosum)的干燥剂。在这些情况下,本发明化合物通常按与用作除草剂的活性成分的情况相同的方法配制,而且可以在作物收获之前单独或与其它收获助剂一起用于叶面处理。
实施例
通过以下制备实施例、制剂实施例和试验实施例进一步说明本发明,但是,本发明并不局限于这些实施例。
下面将表述本发明化合物及其制备中间体的制备实施例。制备实施例1
首先,将400mg(1.2mmol) 2-(4-氯-2-氟-5-羟基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(下文称为中间体1;在下文所述参考制备实施例中制备)溶于2.0ml N,N-二甲基甲酰胺,在其中加入257mg(1.86mmol)碳酸钾和286mg(1.36mmol)4-溴丁烯酸甲酯,混合物于室温搅拌3小时。把反应混合物倾入水中,用乙酸乙酯萃取。有机层用饱和氯化钠水溶液洗涤,无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到194mg(0.46mmol)2-{4-氯-2-氟-5-(E-3-甲氧基羰基-2-丙烯氧基)苯基}-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(为化合物327),m.p.153.2℃。制备实施例2
首先,将300mg(0.93mmol)2-(4-氯-2-氟-5-羟基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(中间体1)溶于1.5ml N,N-二甲基甲酰胺,在其中加入193mg(1.39mmol)碳酸钾、181mg(1.02mmol)(溴甲基)环己烷和154mg(0.93mmol)碘化钾,混合物于60℃搅拌2小时。把反应混合物倾入水中,用乙酸乙酯萃取。有机层用饱和氯化钠水溶液洗涤,无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到26mg(0.062mmol)2-(4-氯-2-氟-5-环己基甲氧基苯基)-4-甲基-5-三氟甲基-3-氯代-2,3-二氢哒嗪(为化合物271),m.p.90.2℃。制备实施例3
首先,将400mg(1.2mmol)2-(4-氯-2-氟-5-羟基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(中间体1)溶于2.0ml N,N-二甲基甲酰胺,在其中加入257mg(1.86mmol)碳酸钾、220mg(1.48mmol)(溴甲基)环丁烷和226mg(1.36mmol)碘化钾,混合物于60℃搅拌1小时。把反应混合物倾入水中,用乙酸乙酯萃取。有机层用饱和氯化钠水溶液洗涤,无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到66mg(0.17mmol)2-(4-氯-2-氟-5-环丁基甲氧基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(为化合物269),m.p.85.3℃。制备实施例4
首先,将400mg(1.2mmol) 2-(4-氯-2-氟-5-羟基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(中间体1)溶于2.0ml N,N-二甲基甲酰胺,在其中加入257mg(1.86mmol)碳酸钾、200mg(1.48mmol)(溴甲基)环丙烷和246mg(1.48mmol)碘化钾,混合物于60℃搅拌1小时。把反应混合物倾入水中,用乙酸乙酯萃取。有机层用饱和氯化钠水溶液洗涤,无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到115mg(0.31mmol)2-(4-氯-2-氟-5-环丙基甲氧基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(为化合物268),m.p.82.3℃。制备实施例5
首先,将400mg(1.2mmol) 2-(4-氯-2-氟-5-羟基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(中间体1)溶于2.0ml N,N-二甲基甲酰胺,在其中加入257mg(1.86mmol)碳酸钾和165mg(1.36mmol)烯丙基溴,混合物于室温搅拌30分钟。把反应混合物倾入水中,用乙酸乙酯萃取。有机层用饱和氯化钠水溶液洗涤,无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到405mg(1.1mmol)2-{4-氯-2-氟-5-(2-丙烯氧基)苯基}-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(下文称为中间体2),m.p.79.8℃。
然后,将182mg(0.50mmol)中间体2溶于5.0ml二氯甲烷,在其中加入1.5ml 0.2N的碳酸氢钠水溶液和123mg间氯过苯甲酸,混合物于室温搅拌3小时。反应完全后,反应混合物用氯仿萃取。有机层用无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到51mg(0.13mmol)2-{4-氯-2-氟-5-(2,3-环氧丙氧基)苯基}-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(为化合物274),m.p.127.2℃。制备实施例6
在0℃,用10分钟时间于363mg(1.0mmol)2-{4-氯-2-氟-5-(2-丙烯氧基)苯基}-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(中间体2)、1.2ml四氢呋喃、0.25ml水和137mg(0.01mmol)1.85%四氧化锇的水溶液的混合物中加入428mg(2.0mmol)高碘酸钠,将混合物搅拌30分钟后温热至室温,然后再搅拌1.5小时。通过硅藻土过滤该反应混合物,残余物用乙酸乙酯洗涤。合并滤液和乙酸乙酯,混合物依次用水和饱和氯化钠水溶液洗涤,无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到155mg(0.43mmol)2-(4-氯-2-氟-5-甲酰基甲氧基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(为化合物272),m.p.107.1℃。制备实施例7
将180mg(0.49mmol)2-(4-氯-2-氟-5-甲酰基甲氧基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(化合物272)、2.3mg(0.012mmol)对甲苯磺酸一水合物、398mg(3.8mmol)原甲酸三甲酯和0.41mg甲醇的混合物于室温搅拌1小时。加入饱和碳酸氢钠水溶液中和反应混合物,并用氯仿萃取。有机层用无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到98mg(0.24mmol)2-{4-氯-2-氟-5-(2,2-二甲氧基乙氧基)苯基}-4-甲基-5-三氟甲基-3-氧代-2,-二氢哒嗪(为化合物291),m.p.86.0℃。制备实施例8
将180mg(0.49mmol)2-(4-氯-2-氟-5-甲酰基甲氧基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(化合物272)、1.8mg(0.0093mmol)对甲苯磺酸一水合物、73mg(0.49mmol)原甲酸三甲酯和0.32g乙二醇的混合物于60℃搅拌3小时。使反应混合物的温度回至室温,然后加入饱和碳酸氢钠水溶液中和,并用氯仿萃取。有机层用无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到79mg(0.19mmol)2-{4-氯-2-氟-5-(2,5-二氧杂环戊基乙氧基)苯基}-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(为化合物294)。
1H-NMR(300MHz,CDCl3,TMS)δ(ppm):2.42(3H,q,J=1.7Hz),3.9-4.0(2H,m),4.0-4.1(4H,m),5.33(1H,t,J=3.4Hz),7.03(1H,d,J=6.3Hz),7.31(1H,d,J=9.0Hz),8.00(1H,s).制备实施例9
将180mg(0.49mmol)2-(4-氯-2-氟-5-甲酰基甲氧基苯基)-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(化合物272)、1.8mg(0.0093mmol)对甲苯磺酸一水合物、73mg(0.49mmol)原甲酸三甲酯和0.39g 1,3-丙二醇的混合物于60℃搅拌3小时。使反应混合物的温度回至室温,然后加入饱和碳酸氢钠水溶液中和,并用氯仿萃取。有机层用无水硫酸镁干燥和浓缩。残余物进行硅胶柱色谱纯化,得到163mg(0.39mmol)2-{4-氯-2-氟-5-(2,6-二噁烷基乙氧基)苯基}-4-甲基-5-三氟甲基-3-氧代-2,3-二氢哒嗪(为化合物295),m.p.112.4℃。
本发明化合物的某些实施例以通式(1)化合物的各取代基定义表示,和它们的化合物编号一起列于表1。表中的“n”、“i”和“c”分别表示正-、异-和环-,以及“(O)”是指氧原子与相邻的两个碳原子一起形成环氧化物。
表1
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
123456789101112131415161718192021222324 | HHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHH | cC3H5cC4H7cC5H8cC6H11CHOCH2C6H5CH(O)CH2CH(O)CHCH3CH2CH(O)CH2CH2CH2CH(O)CH2CH2cC3H5(CH2)2cC3H5CH2cC4H7CH2cC6H11CH2CHO(CH2)2CHO(CH2)3CHOCH(CH3)CHOCH=CHcC3H5CH=CHCH2cC3H5CH=CHCH2cC4H7CH=CHCHOCH=C(CH3)CHOCH(OR6)2 | CH3 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
2526272829303132333435363738394041424344454647484950515253 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH(OR6)2CH(OR6)2CH(OR6)(OR7)CH(OR6)(OR7)CH(OR6)(OR7)CH2CH(OR6)2CH2CH(OR6)2CH2CH(OR6)(OR7)CH2CH(OR6)(OR7)CH2CH2CH(OR6)2CH2CH2CH(OR6)2CH2CH2CH(OR6)(OR7)CH2CH2CH(OR6)(OR7)CH=CHCH(OR6)2CH=CHCH(OR6)2CH(CH3)CH(OR6)2CH(CH3)CH(OR6)(OR7)CH(SR6)2CH(SR6)2CH(SR6)2CH(SR6)(SR7)CH(SR6)(SR7)CH(SR6)(SR7)CH2CH(SR6)2CH2CH(SR6)2CH2CH(SR6)(SR7)CH2CH(SR6)(SR7)CH2CH2CH(SR6)2CH2CH2CH(SR6)2 | C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5CH3(CH2)2CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R8或R6-R7 |
5455565758596061626364656667686970717273747576777879808182 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH2CH2CH(SR6)(SR7)CH2CH2CH(SR6)(SR7)CH=CHCH(SR6)2CH=CHCH(SR6)3CH=CHCOOHCH=C(CH3)COOHCH=CHCOOCH3CH=CHCOOC2H5CH=CHCOOnC3H7CH=CHCOOiC3H7CH=C(CH3)COOCH3CH=C(CH3)COOC2H5CH=C(CH3)COOnC3H7CH=C(CH3)COOiC3H7CH=CHCOOCH2CH2ClCH=CHCOOCH2OCH3CH=C(CH3)COOCH2OCH3CH=CHCOOcC3H5CH=CHCOOcC4H7CH=CHCOOcC5H9CH=C(CH3)COOcC3H5CH=C(CH3)COOcC4H7CH=C(CH3)COOcC5H9CH=CHCOCH3CH=CHCOC2H5CH=C(CH3)COCH3CH=CHCOCH2ClCH=CHCOCH2CH2OCH3CH=CHCOcC3H5 | (CH2)2(CH2)3CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
8384858687888990919293949596979899100101102103104105106107108109110111 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHCH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHCH2CH3HHHHHHHHHHHHHHHHHHHHHH | CH=CHCOcC4H7CH=CHCOcC5H9CH=CHCOcC6H11CH=C(CH3)COcC5H9CH=C(CH3)COcC6H11CH=CHCOOCH3CH=CHCOOC2H5cC3H5cC4H7cC5H8cC6H11CHOCH2C6H5CH(O)CH2CH(O)CHCH3CH2CH(O)CH2CH2CH2CH(O)CH2CH2cC3H5(CH2)2cC3H5CH2cC4H7CH2cC6H11CH2CHO(CH2)2CHO(CH2)3CHOCH(CH3)CHOCH=CHcC3H5CH=CHCH2cC3H5CH=CHCH2cC4H7CH=CHCHO |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
112113114115116117118119120121122123124125126127128129130131132133134135136137138139140 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF6CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH=C(CH3)CHOCH(OR6)2CH(OR6)CH(OR6)CH(OR6)(OR7)CH(OR6)(OR7)CH(OR6)(OR7)CH2CH(OR6)2CH2CH(OR6)2CH2CH(OR6)(OR7)CH2CH(OR6)(OR7)CH2CH2CH(OR6)2CH2CH2CH(OR6)2CH2CH2CH(OR6)(OR7)CH2CH2CH(OR6)(OR7)CH=CHCH(OR6)2CH=CHCH(OR6)2CH(CH3)CH(OR6)2CH(CH3)CH(OR6)(OR7)CH(SR6)2CH(SR6)2CH(SR6)2CH(SR6)(SR7)CH(SR6)(SR7)CH(SR6)(SR7)CH2CH(SR6)2CH2CH(SR6)2CH2CH(SR6)(SR7)CH2CH(SR6)(SR7) | CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5CH3(CH2)2CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R2 | R4 | R5 | R6或R6-R7 |
141142143144145146147148149150151152153154155156157158159160161162163164165166167168169 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH2CH2CH(SR6)2CH2CH2CH(SR6)2CH2CH2CH(SR6)(SR7)CH2CH2CH(SR6)(SR7)CH=CHCH(SR6)2CH=CHCH(SR6)3CH=CHCOOHCH=C(CH3)COOHCH=CHCOOCH3CH=CHCOOC2H5CH=CHCOOnC3H7CH=CHCOOiC3H7CH=C(CH3)COOCH3CH=C(CH3)COOC2H5CH=C(CH3)COOnC3H7CH=C(CH3)COOiC3H7CH=CHCOOCH2CH2ClCH=CHCOOCH2OCH3CH=C(CH3)COOCH2OCH3CH=CHCOOcC3H5CH=CHCOOcC4H7CH=CHCOOcC5H9CH=C(CH3)COOcC3H5CH=C(CH3)COOcC4H7CH=C(CH3)COOcC5H9CH=CHCOCH3CH=CHCOC2H5CH=C(CH3)COCH3CH=CHCOCH2Cl | CH3C2H5(CH2)2(CH2)3CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
170171172173174175176177178179180181182183184185186187188189190191192193194195196197198 | HHHHHHHHHFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3HHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHCH3CH3HHHHHHHHHHHHHHHHHHHH | CH=CHCOCH2CH2OCH3CH=CHCOcC3H5CH=CHCOcC4H7CH=CHCOcC5H9CH=CHCOcC6H11CH=C(CH3)COcC5H9CH=C(CH3)COcC6H11CH=CHCOOCH3CH=CHCOOC2H5cC3H5cC4H7cC5H9cC6H11CHOCH2C6H5CH(O)CH2CH(O)CHCH3CH2CH(O)CH2CH2CH2CH(O)CH2CH2cC3H5(CH2)2cC3H5CH2cC4H7CH2cC6H11CH2CHO(CH2)2CHO(CH2)3CHOCH(CH3)CHOCH=CHcC3H5CH=CHCH2cC3H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
199200201202203204205206207208209210211212213214215216217218219220221222223224225226227 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH=CHCH2cC4H7CH=CHCHOCH=C(CH3)CHOCH(OR6)2CH(OR6)2CH(OR6)2CH(OR6)(OR7)CH(OR6)(OR7)CH(OR6)(OR7)CH2CH(OR6)2CH2CH(OR6)2CH2CH(OR6)(OR7)CH2CH(OR6)(OR7)CH2CH2CH(OR6)2CH2CH2CH(OR6)2CH2CH2CH(OR6)(OR7)CH2CH2CH(OR6)(OR7)CH=CHCH(OR6)2CH=CHCH(OR6)2CH(CH3)CH(OR6)2CH(CH3)CH(OR6)(OR7)CH(SR6)2CH(SR6)2CH(SR6)2CH(SR6)(SR7)CH(SR6)(SR7)CH(SR6)(SR7)CH2CH(SR6)2CH2CH(SR6)2 | CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5CH3(CH2)2CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
228229230231232233234235236237238239240241242243244245246247248249250251252253254255256 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH3CH(SR6)(SR7)CH2CH(SR6)(SR7)CH2CH2CH(SR6)2CH2CH2CH(SR6)2CH2CH2CH(SR6)(SR7)CH2CH2CH(SR6)(SR7)CH=CHCH(SR6)2CH=CHCH(SR6)3CH=CHCOOHCH=C(CH3)COOHCH=CHCOOCH3CH=CHCOOC2H5CH=CHCOOnC3H7CH=CHCOOiC3H7CH=C(CH3)COOCH3CH=C(CH3)COOC2H5CH=C(CH3)COOnC3H7CH=C(CH3)COOiC3H7CH=CHCOOCH2CH2ClCH=CHCOOCH2OCH3CH=C(CH3)COOCH2OCH3CH=CHCOOcC3H5CH=CHCOOcC4H7CH=CHCOOcC5H9CH=C(CH3)COOcC3H5CH=C(CH3)COOcC4H7CH=C(CH3)COOcC5H9CH=CHCOCH3CH=CHCOC2H5 | (CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
257258259260261262263264265266267268269270271272273274275276277278279280281282283284285 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHCH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHCH3CH3HHHHHHHHHHHHHHHHHH | CH=C(CH3)COCH3CH=CHCOCH3ClCH=CHCOCH2CH2OCH3CH=CHCOcC3H5CH=CHCOcC4H7CH=CHCOcC5H9CH=CHCOcC6H11CH=C(CH3)COcC5H9CH=C(CH3)COcC6H11CH=CHCOOCH3CH=CHCOOC2H5cC3H5cC4H7cC6H9cC6H11CHOCH2C6H5CH(O)CH2CH(O)CHCH3CH2CH(O)CH2CH2CH2CH(O)CH2CH2cC3H5(CH2)2cC3H5CH2cC4H7CH2cC6H11CH2CHO(CH2)2CHO(CH2)3CHOCH(CH3)CHO |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
286287288289290291292293294295296297298299300301302303304305306307308309310311312313314 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH=CHcC3H5CH=CHCH3cC2H5CH=CHCH2cC4H7CH=CHCHOCH=C(CH3)CHOCH(OR6)2CH(OR6)2CH(OR6)2CH(OR6)(OR7)CH(OR6)(OR7)CH(OR6)(OR7)CH2CH(OR6)2CH2CH(OR6)2CH2CH(OR6)(OR7)CH2CH(OR6)(OR7)CH2CH2CH(OR6)2CH2CH2CH(OR6)2CH2CH2CH(OR6)(OR7)CH2CH2CH(OR6)(OR7)CH=CHCH(OR6)2CH=CHCH(OR6)2CH(CH3)CH(OR6)2CH(CH3)CH(OR6)(OR7)CH(SR6)2CH(SR6)2CH(SR6)2CH(SR6)(SR7)CH(SR6)(SR7)CH(SR6)(SR7) | CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5CH3(CH2)2CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
315316317318319320321322323324325326327328329330331332333334335336337338339340341342343 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH2CH(SR6)2CH2CH(SR6)2CH2CH(SR6)(SR7)CH2CH(SR6)(SR7)CH2CH2CH(SR6)2CH2CH2CH(SR6)2CH2CH2CH(SR6)(SR7)CH2CH2CH(SR6)(SR7)CH=CHCH(SR6)2CH=CHCH(SR6)3CH=CHCOOHCH=C(CH3)COOHCH=CHCOOCH3CH=CHCOOC2H5CH=CHCOOnC3H7CH=CHCOOiC3H7CH=C(CH3)COOCH3CH=C(CH3)COOC2H5CH=C(CH3)COOnC3H7CH=C(CH3)COOiC3H7CH=CHCOOCH2CH2ClCH=CHCOOCH2OCH3CH=C(CH3)COOCH2OCH3CH=CHCOOcC3H5CH=CHCOOcC4H7CH=CHCOOcC5H9CH=C(CH3)COOcC3H5CH=C(CH3)COOcC4H7CH=C(CH3)COOcC5H9 | CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
344345346347348349350351352353354355356357358359360361362363364365366367368369370371372 | FFFFFFFFFFFFFClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3HHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHCH3CH3HHHHHHHHHHHHHHHH | CH=CHCOCH3CH=CHCOC2H5CH=C(CH3)COCH3CH=CHCOCH2ClCH=CHCOCH2CH2OCH3CH=CHCOcC3H5CH=CHCOcC4H7CH=CHCOcC5H9CH=CHCOcC6H11CH=C(CH3)COcC5H9CH=C(CH3)COcC6H11CH=CHCOOCH3CH=CHCOOC2H6cC3H5cC4H7cC5H9cC6H11CHOCH2C6H5CH(O)CH2CH(O)CHCH3CH2CH(O)CH2CH2CH2CH(O)CH2CH2cC3H5(CH2)2cC3H5CH2cC4H7CH2cC6H11CH2CHO(CH2)2CHO |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
373374375376377378379380381382383384385386387388389390391392393394395396397398399400401 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | (CH2)3CHOCH(CH3)CHOCH=CHcC3H5CH=CHCH2cC3H5CH=CHCH2cC4H7CH=CHCHOCH=C(CH3)CHOCH(OR6)2CH(OR6)2CH(OR6)2CH(OR6)(OR7)CH(OR6)(OR7)CH(OR6)(OR7)CH2CH(OR6)2CH2CH(OR6)2CH2CH(OR6)(OR7)CH2CH(OR6)(OR7)CH2CH2CH(OR6)2CH2CH2CH(OR6)2CH2CH2CH(OR6)(OR7)CH2CH2CH(OR6)(OR7)CH=CHCH(OR6)2CH=CHCH(OR6)2CH(CH3)CH(OR6)2CH(CH3)CH(OR6)(OR7)CH(SR6)2CH(SR6)2CH(SR6)2CH(SR6)(SR7) | CH3C2H5nC3H7(CH2)2(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5CH3(CH2)2CH3C2H5nC3H7(CH2)2 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
402403404405406407408409410411412413414415416417418419420421422423424425426427428429430 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH(SR6)(SR7)CH(SR6)(SR7)CH2CH(SR6)2CH2CH(SR6)2CH2CH(SR6)(SR7)CH2CH(SR6)(SR7)CH2CH2CH(SR6)2CH2CH2CH(SR6)2CH2CH2CH(SR6)(SR7)CH2CH2CH(SR6)(SR7)CH=CHCH(SR6)2CH=CHCH(SR6)3CH=CHCOOHCH=C(CH3)COOHCH=CHCOOCH2CH=CHCOOC2H5CH=CHCOOnC3H7CH=CHCOOiC3H7CH=C(CH3)OOOCH3CH=C(CH3)COOC2H5CH=C(CH3)COOnC3H7CH=C(CH3)COOiC3H7CH=CHCOOCH2CH2ClCH=CHCOOCH2OCH3CH=C(CH3)COOCH2OCH3CH=CHCOOcC3H5CH=CHCOOcC4H7CH=CHCOOcC5H9CH=C(CH3)COOcC3H5 | (CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
431432433434435436437438439440441442443444445446447448449450451452453454455456457458459 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHCH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHCH3CH3HHHHHHHHHHHHHH | CH=C(CH3)COOcC4H7CH=C(CH3)COOcC5H9CH=CHCOCH3CH=CHCOC2H5CH=C(CH3)COCH3CH=CHCOCH2ClCH=CHCOCH2CH2OCH3CH=CHCOcC3H6CH=CHCOcC4H7CH=CHCOcC5H9CH=CHCOcC6H11CH=C(CH3)COcC5H9CH=C(CH3)COcC6H11CH=CHCOOCH3CH=CHCOOC2H5cC3H5cC4H7cC5H9cC6H11CHOCH2C6H5CH(O)CH2CH(O)CHCH3CH2CH(O)CH2CH2CH2CH(O)CH2CH2cC3H5(CH2)2cC3H5CH2cC4H7CH2cC6H11 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
460461462463464465466467468469470471472473474475476477478479480481482483484485486487488 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH2CHO(CH2)2CHO(CH2)3CHOCH(CH3)CHOCH=CHcC3H5CH=CHCH2cC3H5CH=CHCH2cC4H7CH=CHCHOCH=C(CH3)CHOCH(OR6)2CH(OR6)2CH(OR6)2CH(OR6)(OR7)CH(OR6)(OR7)CH(OR6)(OR7)CH2CH(OR6)2CH2CH(OR6)2CH2CH(OR6)(OR7)CH2CH(OR6)(OR7)CH2CH2CH(OR6)2CH2CH2CH(OR6)2CH2CH2CH(OR6)(OR7)CH2CH2CH(OR6)(OR7)CH=CHCH(OR6)2CH=CHCH(OR6)2CH(CH3)CH(OR6)2CH(CH3)CH(OR6)(OR7)CH(SR6)2CH(SR6)2 | CH3C2H5nC3H7(CH2)3(CH2)3(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5CH3(CH2)2CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
489490491492493494495496497498499500501502503504505506507508509510511512513514515516517 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH(SR6)2CH(SR6)(SR7)CH(SR6)(SR7)CH(SR6)(SR7)CH2CH(SR6)2CH2CH(SR6)2CH2CH(SR6)(SR7)CH2CH(SR6)(SR7)CH2CH2CH(SR6)2CH2CH2CH(SR6)2CH2CH2CH(SR6)(SR7)CH2CH2CH(SR6)(SR7)CH=CHCH(SR6)2CH=CHCH(SR6)3CH=CHCOOHCH=C(CH3)COOHCH=CHCOOCH3CH=CHCOOC2H5CH=CHCOOnC3H7CH=CHCOOiC3H7CH=C(CH3)COOCH3CH=C(CH3)COOC2H5CH=C(CH3)COOnC3H7CH=C(CH3)COOiC3H7CH=CHCOOCH2CH2ClCH=CHCOOCH2OCH3CH=C(CH3)COOCH2OCH3CH=CHCOOcC3H5CH=CHCOOcC4H7 | nC3H7(CH2)2(CH2)2(CH2)4CH3C2H5(CH2)2(CH2)3CH3C2H5(CH2)2(CH2)3CH3C2H5 |
表1续
化合物编号 | X | Y | Z1 | R1 | R2 | R3 | R4 | R5 | R6或R6-R7 |
5l8519520521522523524525526527528529530531532533534 | ClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClCl | OOOOOOOOOOOOOOOOO | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHCH3CH3 | CH=CHCOOcC5H9CH=C(CH3)COOcC3H5CH=C(CH3)COOcC4H7CH=C(CH3)COOcC5H9CH=CHCOCH3CH=CHCOC2H5CH=C(CH3)COCH3CH=CHCOCH2ClCH=CHCOCH2CH2OCH3CH=CHCOcC3H5CH=CHCOcC4H7CH=CHCOcC5H9CH=CHCOcC6H11CH=C(CH2)COcC5H9CH=C(CH3)COcC6H11CH=CHCOOCH3CH=CHCOOC2H5 |
下面描述中间体1的参考制备例。参考制备例
首先,将32.3g 5-氨基-2-氯-4-氟苯酚(该化合物通过在欧洲专利申请公开EP-61741-A的说明书中所公开的方法制备)与150ml浓盐酸混合,并在50℃搅拌混合物30分钟。在0℃下,于10分钟期间,将15g硝酸钠的40ml水溶液逐滴加入该混合物,混合物在0℃搅拌1小时后冷却至-50℃。在-50℃下,向该混合物中快速滴加132g氯化锡(II)溶于132g浓盐酸所形成的溶液,并使混合物缓慢回到室温,随后在室温下再搅拌1小时。过滤收集生成的固体,在80℃减压干燥,得到75g 2-氟-4-氯-5-羟基苯肼盐酸盐晶体粗产物。
1H-NMR(DMSO-d6,TMS,δ(ppm)):3-5(2H,br),6.73(1H,d),7.22(1H,d),8.20(1H,s),9-11(2H,br).
然后,将49.2g乙酸钠和40.5g 1,1-二溴-3,3,3-三氟丙酮溶于400ml水中,并将溶液在80至90℃加热40分钟。溶液冷却至0℃后,向其中加入75g 2-氟-4-氯-5-羟基苯肼盐酸盐晶体粗产物。室温下搅拌该混合物70分钟,过滤收集生成的晶体,和减压干燥,得到35.4g 3,3,3-三氟-2-氧代丙醛1-(4-氯-2-氟-5-羟基苯腙)。
1H-NMR(300MHz,CDCl3,TMS,δ(ppm)):5.49(1H,s),7.15(1H,d,J=10.5Hz),7.24(1H,d,J=7.4Hz),7.38(1H,q,J=1.8Hz),8.75(1H,s).
然后,将如此得到的12.9g 3,3,3-三氟-2-氧代丙醛1-(4-氯-2-氟-5-羟基苯腙)和22.3g(乙酯基亚乙基)三苯基正膦溶于110ml THF,并将该溶液回流加热3小时。减压蒸除溶剂后,将残余物进行硅胶柱色谱纯化,得到8.8g 2-(2-氟-4-氯-5-羟基苯基)-4-甲基-5-三氟甲基哒嗪-3-酮(中间体1)。
以下将描述制剂实施例,其中本发明化合物由该化合物在表1中的化合物编号表示,份数按重量计。制剂实施例1
将50份本发明化合物1-534中的一种化合物、3份木质素磺酸钙、2份十二烷基硫酸钠与45份合成的水合氧化硅均匀粉碎和混合得到每种化合物的可湿性粉剂。制剂实施例2
将10份本发明化合物1-534中的一种化合物、14份聚氧乙烯苯乙烯基苯基醚、6份十二烷基苯磺酸钙、35份二甲苯与35份环己酮均匀混合得到每种化合物的乳油。制剂实施例3
将2份本发明化合物1-534中的一种化合物、2份合成的水合氧化硅、2份木质素磺酸钙、30份膨润土与64份高岭土均匀粉碎和混合,将该混合物与加入的水一起均匀捏制、造粒并干燥得到每种化合物的颗粒剂。制剂实施例4
将25份本发明化合物1-534中的一种化合物、50份10%聚乙烯醇水溶液与25份水混合并湿研磨,直到平均颗粒大小达到5μm或更小,得到每种化合物的悬浮剂。
下面的试验实施例将证明本发明化合物可用作除草剂的活性成分。本发明化合物用表1中所示的相应的化合物编号表示。
除草活性和植物毒性用指标0-5分6个等级评价,即用数字“0”,“1”,“2”,“3”,“4”或“5”表示,其中“0”是指在考察时已处理植物(即杂草和作物)与未处理植物之间的发芽或生长程度没有任何差别或只有很小差别,而“5”是指试验植物完全死亡或其发芽或生长被完全抑制。当评定等级为“4”或“5”时,表明除草活性优良,但当评定等级为“3”或更低的等级时,则表示除草活性不足。植物毒性当评定等级为“0”或“1”时,则表示实际应用时是可以耐受的,但当评定等级为“2”或更高级时,则表示不能耐受。
试验实施例1:旱田叶面处理
在直径10cm,深10cm的圆筒性塑料盆中填上土壤,在土壤中播种稗草(Echinochloa crus-galli),裂叶牵牛(Ipomoea hederacea)和苘麻(Abutilontheophrasti)的种子,并使试验植物在温室中生长19天。按照制剂实施例2,将下面所列的每种受试化合物配制成乳油,用含有分散剂的水稀释到预定浓度。利用喷雾器,以每公顷1000升的体积将稀释液均匀喷雾到受试植物的叶面上。喷完后,使试验植物在温室中生长19天,测定除草活性。结果示于表2。表2
试验混合物 | 活性成分的施加量(g/ha) | 除草活性 | ||
稗草 | 裂叶牵牛 | 尚麻 | ||
268269271272274291294295327 | 500500500500500500500500500 | 555545555 | 555555555 | 555555555 |
试验实施例2:旱田土壤表面处理
将直径10cm,深10cm的圆筒形塑料盆中填上土壤,在土壤中播种稗草(Echinochloa crus-galli),裂叶牵牛(Ipomoea hederacea)和苘麻(Abutilontheophrasti)的种子。按照制剂实施例2,将下面所列的每种受试化合物配制成乳油,用水稀释到预定浓度。利用喷雾器,以每公顷1000升的体积将稀释液均匀喷雾到盆中的土壤表面上。喷雾完后,使试验植物在温室中生长19天,测定除草活性。结果示于表3。
表3
试验混合物 | 活性成分的施加量(g/ha) | 除草活性 | ||
稗草 | 裂叶牵牛 | 尚麻 | ||
268269271272274291294295327 | 200020002000200020002000200020002000 | 555555555 | 555555555 | 555555555 |
试验实施例3:水田漫灌处理
将直径9cm,深11cm的圆筒形塑料盆中填上土壤,在土壤中播种上稗草(Echinochloa oryzicola)的种子。将这些盆灌上水形成水田,并使受试植物在温室中生长7天。按照制剂实施例2,将下面所列的每种受试化合物配制成乳油,用水稀释到预定浓度。以每公顷50升的体积将稀释液施加到盆中的水表面。施加完之后,使试验植物在温室中生长16天,测定除草活性。结果示于表4。表4
试验混合物 | 活性成分的施加量(g/ha) | 除草活性 |
稗草 | ||
268269271272274291294295327 | 250250250250250250250250250 | 555555555 |
试验实施例4:旱田叶面处理
将面积25×18cm2,深7cm的塑料盆中填上土壤,并在土壤中播种稻(Oryza sativa)和稗草(Echinochloa crus-galli)的种子,并使受试植物生长15天。按照制剂实施例2,将下面所列的每种受试化合物配制成乳油,用水稀释到预定浓度。以每公顷1000升的体积用喷雾器将稀释液均匀喷雾到受试植物的叶面上。尽管杂草和作物以不同阶段生长取决于其品种的不同,但是,此时这些有害杂草和作物为1-至3-叶期,植株高度为8-15cm。施药后24天测定除草活性和植物毒性。结果示于表5。此试验的整个周期在温室中进行。表5
试验化合物 | 活性成分的施加量(g/ha) | 作物的植物毒性 | 除草活性 |
稻 | 稗草 | ||
271 | 63 | 0 | 5 |
Claims (17)
R2和R3相同或不同,独立地是氢、C1-C3烷基、C1-C3卤代烷基或C1-C3烷氧基C1-C3烷基;
X是氢或卤素;
Y是卤素、硝基、氰基或三卤代甲基;
Z1是氧、硫、CH2或NH;
R4是氢、卤素或C1-C6烷基;以及
R5是C3-C8环烷基、甲酰基、苄基、带有环氧基的C2-C10烷基、C3-C8环烷基C1-C6烷基、甲酰基C1-C6烷基、C3-C8环烷基C2--C6链烯基、甲酰基C2--C6链烯基、在同一碳原子上被OR6和OR7取代的C1-C6烷基、在同一碳原子上被OR6和OR7取代的C2--C6链烯基、在同一碳原子上被SR6和SR7取代的C1-C6烷基、在同一碳原子上被SR6和SR7取代的C2--C6链烯基、羧基C2--C6链烯基、(C1-C8烷氧基)羰基C2--C6链烯基、(C1-C6卤代烷氧基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷氧基}羰基C2--C6链烯基、(C3-C8环烷氧基)羰基C2--C6链烯基、(C1-C6烷基)羰基C2--C6链烯基、(C1-C6卤代烷基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷基}羰基C2-C6链烯基或(C3--C8环烷基)羰基C2--C6链烯基;
R6和R7相同或不同,各自独立地是C1-C6烷基或C1-C6卤代烷基,或者R6和R7一起形成可被卤素选取代的亚乙基、可被卤素任选取代的三亚甲基、被卤素选择取代的四亚甲基、被卤素选择取代的五亚甲基或被卤素选择取代的亚乙基氧基亚乙基。
2.根据权利要求1的哒嗪-3-酮衍生物,其中Z1是氧、硫或NH;以及R5是甲酰基、甲酰基C1-C6烷基、甲酰基C2--C6链烯基、在同一碳原子上被OR6和OR7取代的C1-C6烷基、在同一碳原子上被OR6和OR7取代的C2--C6链烯基、在同一碳原子上被SR6和SR7取代的C1-C6烷基、在同一碳原子上被SR6和SR7取代的C2--C6链烯基、(C1-C6烷基)羰基C2--C6链烯基、(C1-C6卤代烷基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷基}羰基C2--C6链烯基或(C3-C8环烷基)羰基C2--C6链烯基;R6和R7相同或不同,各自独立地是C1-C6烷基或C1-C6卤代烷基。
3.根据权利要求1的哒嗪-3-酮衍生物,其中R1是三氟甲基,R2是甲基或氢,R3是氢,X是氟,Y是氯,R4是氢,以及R5是C3-C8环烷基、苄基、带有环氧基的C2-C10烷基、C3-C8环烷基C1-C6烷基、C3-C8环烷基C2--C6链烯基、在同一碳原子上被OR6和OR7取代的C1-C6烷基、在同一碳原子上被OR6和OR7取代的C2--C6链烯基、在同一碳原子上被SR6和SR7取代的C1-C6烷基、在同一碳原子上被SR6和SR7取代的C2--C6链烯基、羧基C2--C6链烯基、(C1-C8烷氧基)羰基C2--C6链烯基、(C1-C6卤代烷氧基)羰基C2--C6链烯基、{(C1-C4烷氧基)C1-C4烷氧基}羰基C2--C6链烯基、或(C3-C8环烷氧基)羰基C2--C6链烯基,R6和R7一起形成亚乙基、三亚甲基、四亚甲基、五亚甲基或亚乙基氧基亚乙基。
4.根据权利要求1的哒嗪-3-酮衍生物,其中R1是三氟甲基,R2是甲基或氢,R3是氢,X是氟,Y是氯,R4是氢,R5是C3-C8环烷基、带有环氧基的C2-C10烷基、(C1-C8烷氧基)羰基C2--C6链烯基或在同一碳原子上被OR6和OR7取代的C1-C6烷基,R6和R7一起形成亚乙基或三亚甲基。
5.根据权利要求1的哒嗪-3-酮衍生物,其中R1是三氟甲基,R2是甲基或氢,R3是氢,X是氟,Y是氯,R4是氢,和R5是C3-C8环烷基;
6.根据权利要求1至5之任一项的哒嗪-3-酮衍生物,其中Z1是氧。
7.根据权利要求1、2或6的哒嗪-3-酮衍生物,其中Y是卤素,R1是三氟甲基,R2是氢或甲基,R3是氢,和R4是氢或甲基。
8.根据权利要求7的哒嗪-3-酮衍生物,其中X是氟。
9.根据权利要求1、2、6、7或8的哒嗪-3-酮衍生物,其中R4是氢。
10.根据权利要求1、2、6、7、8或9的哒嗪-3-酮衍生物,其中R5是甲酰基或在同一碳原子上被OR6和OR7取代的C1-C6烷基,R6和R7相同或不同,各自独立地是C1-C6烷基。
11.根据权利要求1的哒嗪-3-酮衍生物,其中R1是CF2J基团,和J表示氢、氟、氯或三氟甲基。
12.根据权利要求2的哒嗪-3-酮衍生物,其中R1是CF2J基团,和J表示氢、氟、氯或三氟甲基。
13.根据权利要求1的的哒嗪-3-酮衍生物,其中R1是三氟甲基。
14.根据权利要求2的哒嗪-3-酮衍生物,其中R1是三氟甲基。
15.除草剂,该除草剂含有权利要求1至14中任一项所定义的哒嗪-3-酮衍生物作为活性成分。
16.控制杂草的方法,该方法包括将权利要求1至14中任一项所定义的哒嗪-3-酮衍生物施用于杂草或杂草生长或将要生长的地方。
17.权利要求1至14中任一项所定义的哒嗪-3-酮衍生物作为除草剂的用途。
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CN100473647C (zh) * | 2000-09-18 | 2009-04-01 | 卫材R&D管理有限公司 | 哒嗪酮和三嗪酮化合物及其作为药物制剂的用途 |
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DE3321007A1 (de) * | 1983-06-10 | 1984-12-13 | Basf Ag, 6700 Ludwigshafen | Substituierte 4,5-dimethoxypyridazone, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses als herbizide |
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