CN103119019A - (4-卤代烷基-3-硫代苯甲酰基)环己二酮及其作为除草剂的用途 - Google Patents
(4-卤代烷基-3-硫代苯甲酰基)环己二酮及其作为除草剂的用途 Download PDFInfo
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- CN103119019A CN103119019A CN201180045550XA CN201180045550A CN103119019A CN 103119019 A CN103119019 A CN 103119019A CN 201180045550X A CN201180045550X A CN 201180045550XA CN 201180045550 A CN201180045550 A CN 201180045550A CN 103119019 A CN103119019 A CN 103119019A
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- 239000004009 herbicide Substances 0.000 title abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 94
- -1 phenyloxycarbonyl Chemical group 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 40
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000005864 Sulphur Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 244000038559 crop plants Species 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- 239000002917 insecticide Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 239000000642 acaricide Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 229940031815 mycocide Drugs 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 249
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 184
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 181
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 181
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 180
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 180
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 180
- 241000196324 Embryophyta Species 0.000 description 77
- 238000005160 1H NMR spectroscopy Methods 0.000 description 42
- 244000025254 Cannabis sativa Species 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 26
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 24
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- 244000037671 genetically modified crops Species 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000005562 Glyphosate Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 10
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000004562 water dispersible granule Substances 0.000 description 9
- 239000004563 wettable powder Substances 0.000 description 9
- 239000005630 Diquat Substances 0.000 description 8
- 239000005531 Flufenacet Substances 0.000 description 8
- 239000005564 Halosulfuron methyl Substances 0.000 description 8
- 239000005584 Metsulfuron-methyl Substances 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 8
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 8
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 8
- 235000006408 oxalic acid Nutrition 0.000 description 8
- 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 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000207783 Ipomoea Species 0.000 description 7
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- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 6
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 6
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 6
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 6
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 6
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- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 6
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- IRECWLYBCAZIJM-UHFFFAOYSA-N Flumiclorac pentyl Chemical group C1=C(Cl)C(OCC(=O)OCCCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F IRECWLYBCAZIJM-UHFFFAOYSA-N 0.000 description 6
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- 239000005566 Imazamox Substances 0.000 description 6
- JUJFQMPKBJPSFZ-UHFFFAOYSA-M Iodosulfuron-methyl-sodium Chemical compound [Na+].COC(=O)C1=CC=C(I)C=C1S(=O)(=O)[N-]C(=O)NC1=NC(C)=NC(OC)=N1 JUJFQMPKBJPSFZ-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 description 6
- XJCLWVXTCRQIDI-UHFFFAOYSA-N Sulfallate Chemical compound CCN(CC)C(=S)SCC(Cl)=C XJCLWVXTCRQIDI-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
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- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 6
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 description 6
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- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 description 6
- DNUAYCRATWAJQE-UHFFFAOYSA-N flufenpyr-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(N2C(C(C)=C(C=N2)C(F)(F)F)=O)=C1F DNUAYCRATWAJQE-UHFFFAOYSA-N 0.000 description 6
- ZCNQYNHDVRPZIH-UHFFFAOYSA-N fluthiacet-methyl Chemical compound C1=C(Cl)C(SCC(=O)OC)=CC(N=C2N3CCCCN3C(=O)S2)=C1F ZCNQYNHDVRPZIH-UHFFFAOYSA-N 0.000 description 6
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- 125000001188 haloalkyl group Chemical group 0.000 description 6
- MFSWTRQUCLNFOM-SECBINFHSA-N haloxyfop-P-methyl Chemical group C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 description 6
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 6
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 6
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 6
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
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- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
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- 229960003742 phenol Drugs 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000005097 photorespiration Effects 0.000 description 1
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- 108010001545 phytoene dehydrogenase Proteins 0.000 description 1
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- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
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Abstract
Description
本发明涉及除草剂的技术领域,特别是在有用植物作物中选择性防治阔叶杂草和禾本科杂草的除草剂技术领域。
已经从多种出版物得知某些苯甲酰环己二酮具有除草性能。例如,EP0338992A1和WO2011/012247A1各自公开了被不同基团取代的2-(3-烷硫基苯甲酰基)环己二酮。US2002/165096A1和DE19961465A1公开了在苯环的3位上带有直接键合的硫基的苯甲酰环己二酮。
然而,从这些出版物中已知的化合物的除草活性通常是不够的。因此,本发明的一个目标是提供具有改进的除草性质——相对于现有技术中已知的化合物而言——的除草活性化合物。
已经发现某些苯甲酰环己二酮特别适合用作除草剂,该苯甲酰环己二酮的环己二酮环被桥接且其苯环在3位上带有硫基和在4位上带有卤代烷基。本发明首先提供了通式(I)的(4-卤代烷基-3-硫代苯甲酰基)环己二酮或其盐
其中
X为(C1-C4)-烷基,
Y为(C1-C4)-卤代烷基,除了三氟甲基,
A和Z彼此独立地为氧、-S(O)m-、-N(R5)-、羰基或(C1-C4)-亚烷基,该(C1-C4)-亚烷基被选自氧、-S(O)m-、-N(R5)-和羰基的q个单元所间断,并且被s个R6基团所取代,
R1为(C1-C4)-烷基,
R2为羟基、SR7、NR8R9,
R3和R4彼此独立地为氢或(C1-C4)-烷基,
R5为氢、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-烷基羰基、(C1-C4)-烷氧基羰基、苯基羰基或苯氧基羰基,在两个最后提及的基团中苯环被最高达p个卤原子和最高达p个选自硝基、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基,和(C1-C4)-卤代烷氧基的基团所取代,
R6为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基或(C1-C4)-烷氧基-(C1-C4)-烷基,
R7为(C1-C4)-烷基或被p个卤原子或p个选自硝基、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基,和(C1-C4)-卤代烷氧基的基团所取代的苯基,
R8为氢、(C1-C4)-烷基、或(C1-C4)-烷氧基,
R9为氢、或(C1-C4)-烷基,
或
R8和R9与它们所连接的氮原子形成5元或6元饱和的,部分饱和的或完全不饱和的环,该环包含m个选自氧、硫和氮的其他杂原子,并且该环被最高达s个卤原子和最高达p个选自氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基,和(C1-C4)-卤代烷氧基的基团所取代,
m和n彼此独立地为0、1或2,
p为0、1、2、3、4或5,
q为0或1,
s为0、1、2、3、4、5、6、7或8。
当R2为羟基时,本发明的式(I)的化合物可以不同的互变异构体结构的形式存在,这取决于外部条件,例如溶剂和pH值,如下所示:
取决于取代基的性质,式(I)的化合物含有酸性质子,其可以通过与碱反应而除去。合适的碱的实例包括锂、钠、钾、镁和钙的氢化物、氢氧化物和碳酸盐,以及氨水和有机胺如三乙胺和吡啶。此外,可以通过与有机酸如甲酸或乙酸的反应,以及与无机酸如磷酸、盐酸或硫酸的反应形成盐。这样的盐同样由本发明提供。
在式(I)和所有随后的式中,具有多于两个的碳原子的烷基可以是直链或支链的。烷基是例如甲基、乙基、正丙基或异丙基、正丁基、异丁基、叔丁基或2-丁基、戊基、己基如正己基、异己基和1,3-二甲基丁基。卤素是氟、氯、溴或碘。
当一个基团被取代基团多取代时,这指的是所述基团被所指定的取代基团中的一个或多个相同的或不同的基团所取代。
取决于取代基的种类和连接,式(I)的化合物可以立体异构体的形式存在。例如,如果存在一个或多个不对称取代的碳原子或亚砜,则可能有对映异构体和非对映异构体。立体异构体可由制备过程所得的混合物由常规分离方法如色谱分离方法获得。也可通过使用光学活性的原料和/或助剂的立体选择性反应来选择性地制备立体异构体。本发明还涉及式(I)包含的但没有具体定义的所有立体异构体及其混合物。
特别关注的是式(I)的化合物,其中
X为(C1-C4)-烷基,
Y为(C1-C4)-卤代烷基,除了三氟甲基,
A和Z彼此独立地为氧或(C1-C4)-亚烷基,
R1为(C1-C4)-烷基,
R2为羟基,且
R3和R4彼此独立地为氢或(C1-C4)-烷基。
优选式(I)的化合物,其中
X为(C1-C4)-烷基,
Y为三氯甲基、二氟甲基、二氯氟甲基、氯二氟甲基、五氟乙基或七氟异丙基,
A和Z各自为(C1-C4)-亚烷基,
R1为(C1-C4)-烷基,
R2为羟基,且
R3和R4彼此独立地为氢或(C1-C4)-烷基。
特别优选式(I)的化合物,其中
X为甲基,
Y为氯二氟甲基、二氟甲基或五氟乙基,
A和Z彼此独立地各自为CH2或CH2CH2,
R1为甲基,
R2为羟基,
R3和R4各自为氢,且
n为1或2。
极特别优选式(I)的化合物,其中
X为甲基,
Y为五氟乙基,
A和Z彼此独立地各自为CH2或CH2CH2,
R1为甲基,
R2为羟基,
R3和R4为氢,且
n为1或2。
在所有下面给出的式子中,所述取代基和符号具有与式(I)中所述相同的定义,除非另作说明。
其中R2为羟基的本发明的化合物例如,可通过方案1中所示的方法制备:将苯甲酸衍生物(III)——其中L1为烷氧基或卤素——与环己二酮(IV)进行碱催化反应,然后重排,该方法已知于例如WO03/084912。中间体(V)也可以通过苯甲酸(II)与环己二酮(IV)在添加的活性缩合剂,例如N-(3-二甲基氨基丙基)-N'-乙基碳二亚胺盐酸盐的存在下直接反应而制备。
方案1
其中R2具有除羟基之外的含义的本发明的化合物,可根据方案2由根据方案1所得的化合物有用地制备。这类方法基本上为本领域技术人员已知,并描述于例如WO03/084912中。
方案2
式(IV)的环己二酮是市售的,或者可以根据本领域技术人员已知且记载于例如EP0338992和WO2008/071405中的方法制备。式(II)的苯甲酸的制备已知于例如WO2008125214。
苯甲酸(II)可通过一系列的本身由本领域技术人员已知的合成步骤制备。
例如,在4位上带有三氟甲基作为卤代烷基的苯甲酸的合成已知于WO2008125214。取决于卤代烷基的种类,在此文献描述的方法可用于苯甲酸(II)的合成。
其他的可能性是卤代烷基的引入。例如,将五氟乙基引入到苄腈的4位上记载于WO2006/43064和US2007/185058。苄腈可随后转化为相应的苯甲酸(US2007/185058)。还已知的是用卤代烷基取代碘代芳香族化合物,所述反应通过相应的卤代烷基铜化合物进行(A.A.Kolomeitsev et al.,J.Org.Chem.2008,73(7),2607.)。
或者,也可以由其他官能团产生卤代烷基。二氟甲基例如可从相应的甲酰基获得。对于4-甲酰基苄腈而言的这类转化由C.P.Andrieux et al.描述,(Journal of the American Chemical Society1997(119),40,9527)。然后,例如可以在碱性条件下由产物生成相应的苯甲酸(F.Mathey et.al.,Tetrahedron1975(31),391.)。
其他合成苯甲酸的方法——可用于苯甲酸(II)的合成——的可能性已知于WO03/014071。
在苯甲酰基的3位中的硫原子,为了生成n=1或2的化合物,不必在苯甲酸阶段被氧化;例如,这类氧化在烯醇酯或苯甲酰基环己二酮阶段可能也是有用的。
式(II)的苯甲酸是新的,且同样由本发明提供。
可以通过上述反应合成的通式(I)化合物和/或其盐类的集合也可以通过平行的方式制备,这可以手动实现或以半自动或全自动的方式实现。关于这一点,可以例如使反应过程、产物和/或中间体的后处理或纯化自动化。总而言之,这应理解为如例如D.Tiebes在CombinatorialChemistry–Synthesis,Analysis,Screening(Günther Jung编),VerlagWiley1999,第1-34页中所述的过程。
为进行平行的反应过程和后处理,可使用一系列的市售仪器,例如购自Barnstead International,Dubuque,Iowa52004-0797,USA的Calpyso反应模块,或购自Radleys,Shirehill,Saffron Walden,Essex,CB113AZ,England的反应站,或购自PerkinElmer,Waltham,Massachusetts02451,USA的多探针自动化工作站。为了对通式(I)的化合物及其盐类或制备过程中所获得的中间体进行平行纯化,尤其可以使用购自ISCO,Inc.,4700Superior Street,Lincoln,NE68504,USA的色谱设备。
上述设备形成一种模块过程,其中各个单独的方法步骤自动进行,但是在各步骤之间必须进行手动操作。这可通过使用部分或完全一体化的自动化系统而避免,其中所述各自动化模块由例如机器人操控。这类自动化系统可购自例如Caliper,Hopkinton,MA01748,USA。
可以通过使用聚合物负载试剂/清除树脂(scavenger resin)来辅助单个或多个合成步骤的实施。专业文献描述了一系列实验方案,例如在ChemFiles,第4卷,No.1,Polymer-Supported Scavengers and Reagentsfor Solution-Phase Synthesis(Sigma-Aldrich)中。
除了本文所述的方法之外,通式(I)的化合物及其盐的制备可以全部或部分地通过固相负载法进行。为此目的,将所述合成过程中的或适用于所述方法的合成过程中的各个单独的中间体或全部中间体结合至合成树脂上。固相负载合成法在专业文献中有充分的描述,例如Barry A.Bunin,“The Combinatorial Index”,Verlag Academic Press,1998和Combinatorial Chemistry–Synthesis,Analysis,Screening(Günther Jung编),Verlag Wiley,1999。使用固相负载合成法可以进行文献中已知的一系列方案,这些方案也可以通过手动或自动的方法实施。反应可以使用例如IRORI技术,在购自Nexus Biosystems,12140Community Road,Poway,CA92064,USA的微反应器中进行。
通过使用微波技术,在固相和液相上都可以辅助实施单独的或多个合成步骤的方法。专业文献中描述了一系列实验方案,例如在Microwaves in Organic and Medicinal Chemistry(C.O.Kappe和A.Stadler编),Verlag Wiley,2005中。
根据本文所述的方法的制备可以获得物质集合形式的通式(I)化合物及其盐,称为库(library)。本发明也提供了包括至少两种通式(I)化合物及其盐的库。
本发明的通式(I)化合物(和/或其盐)在下文中也被统称为“本发明的化合物”,其对宽范围的经济上重要的单子叶和双子叶一年生杂草植物具有优异的除草活性。所述活性化合物甚至能有效地作用于从根茎、根状茎和其他多年生器官中发芽的难以防治的多年生杂草。
因此,本发明也涉及一种防治不需要的植物或调节植物的生长的方法,优选用于植物作物中,其中将本发明的一种或多种化合物施用在植物上(例如有害植物,例如单子叶或双子叶杂草或不需要的作物植物)、施用于种子(例如谷物、种子或无性繁殖体,例如块茎或带有萌芽的枝条部分)或施用于植物生长区域(例如栽培区域)。在本文中,本发明化合物可以例如在播种前施用(如果合适的话,也可以通过引入土壤而施用)、苗前或苗后施用。可以提及的具体的实例为可以通过本发明的化合物防治的单子叶和双子叶杂草植物群的一些代表,而以下的列举并不限定于某些品种。
以下属的单子叶有害植物:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、假剪股颖属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的双子叶阔叶杂草:苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、单花葵属(Anoda)、春黄菊属(Anthemis)、蔷薇属(Aphanes)、艾属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、芙蓉属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、Mullugo属、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
如果在发芽前将本发明的化合物施用至土壤表面,则完全阻止杂草幼苗的发芽,或者使得杂草生长直至达到子叶期,但之后它们就停止生长,并最终在三至四周后完全死亡。
如果在苗后将所述活性化合物施用至植物的绿色部位,则在处理后生长停止,并且有害植物停留在施用时间点的生长期,或者在一段时间后完全死亡,从而以这种方式在非常早的时期并持续地消除对作物植物有害的杂草的竞争。
虽然本发明的化合物对单子叶和双子叶杂草显示出优异的除草活性,但只会轻微地或完全不损害经济上重要的作物的作物植物,这取决于本发明各个化合物的结构和其施用率,所述的经济上重要的作物例如,以下属的双子叶作物:花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea)、莴苣属(Lactuca)、亚麻属(Linum)、番茄属(Lycopersicon)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia),或以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea),特别是玉蜀黍属和小麦属。这就是本发明化合物极适于选择性地在植物作物中,例如农业有用植物或观赏植物中防治不想要的植物的生长的原因。
此外,本发明的化合物(取决于它们各自的结构和施用的施用率)对作物植物具有突出的生长调节性能。它们以调节的方式参与植物的新陈代谢,并且因此可以用于以定向的方式影响植物的成分,以及有助于收割,例如通过引发脱水和矮化生长。此外,它们也适用于广泛地防治和抑制不想要的营养生长而在这个过程中不损害植物。抑制营养生长在许多单子叶和双子叶作物中起到了非常重要的作用,因为例如可以减少或完全避免倒伏。
由于它们的除草和植物生长调节性能,所述活性化合物也可用于在已知的或待开发的基因修饰植物中防治有害植物。一般地,转基因植物特征在于具有一些特别有利的性质,例如对某些农药的抗性,主要是对于某些除草剂的抗性,对于植物疾病或植物疾病的致病生物的抗性,所述生物例如某些昆虫或微生物,例如真菌、细菌或病毒。其他具体性质涉及到例如采收物的产量、品质、储存性、组成,和具体成分。例如,已知具有提高的淀粉含量或改变的淀粉品质的转基因植物,或者在采收物中具有不同的脂肪酸组成的转基因植物。其他的具体特征可能在于对非生物应激物如热、冷、干旱、盐和紫外线辐射的耐受性或抗性。
优选在有用植物和观赏性植物的经济上重要的转基因作物上使用本发明式(I)的化合物或其盐类,所述植物例如谷物,例如小麦、大麦、黑麦、燕麦、黍、稻、木薯和玉米,或者甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆以及其他蔬菜的作物。
优选在对除草剂的植物毒性效果具有抗性或已通过重组方式产生抗性的有用植物作物中使用式(I)的化合物作为除草剂。
制备与已知的植物相比具有改进特性的新植物的常规方法包括例如常规育种方法和突变体产生法。或者,具有改进特性的新植物可借助重组方法产生(见,例如,EP0221044,EP0131624)。例如描述了以下几种情况:
-通过重组技术修饰作物植物,目的在于使植物中合成的淀粉改性(例如WO92/011376A、WO92/014827A、WO91/019806A);
-通过“基因叠加”对某些草铵磷(glufosinate)类除草剂(参见例如EP-A-0242236、EP-A-0242246)或草甘膦(gluphosate)类除草剂(WO92/00377A)或磺酰脲类除草剂(EP-A-0257993、US5,013,659)或这些除草剂的组合物或混合物具有抗性的转基因作物植物,例如商品名或名称为OptimumTM GATTM(耐草甘膦ALS)的转基因作物植物,例如玉米或大豆。
-能产生苏云金杆菌毒素(Bt毒素)从而使植物对某些害虫具有抗性的转基因作物植物,例如棉花(EP-A-0142924、EP-A-0193259);
-具有改性的脂肪酸组成的转基因作物植物(WO91/013972A),
-具有能够带来增强的抗病能力的新成分或次级代谢产物,例如新的植物抗毒素的基因修饰作物植物(EPA0309862,EPA0464461),
-具有降低的光呼吸的基因修饰植物,其具有较高的产量和较高的应激耐受性(EPA0305398),
-生产药学或诊断上的重要蛋白质的转基因作物植物(“分子药耕(molecular pharming)”)。
-特征在于更高产量或更好品质的转基因作物植物,
-特征在于具有例如上述新性能的组合(“基因叠加”)的转基因作物植物。
许多能够制备具有改进性质的新转基因植物的分子生物技术原则上是已知的,参见例如I.Potrykus and G.Spangenberg(编)Gene Transferto Plants,Springer Lab Manual(1995),Springer Verlag Berlin,Heidelberg或者Christou,"Trends in Plant Science"1(1996)423-431。
为了进行这类重组操作,可以将通过重组DNA序列而产生突变或产生序列改变的核酸分子引入质粒。例如借助于标准方法,可以进行碱基取代、可以移除部分序列或加入天然的或合成的序列。为了将DNA片段彼此连接,可以在片段上添加接头(adapter)或连接体(linker)。见,例如,Sambrook等人,1989,Molecular Cloning,A Laboratory Manual,第二版,Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY;或Winnacker"Gene und Klone",VCH Weinheim第二版,1996。
例如,基因产物活性降低的植物细胞的产生可以通过下列方法实现:通过表达至少一种相应的反义RNA、用于实现共抑制效应的正义RNA,或者通过表达至少一种能够特异性切割上述基因产物的转录物并具有合适结构的核酶。
为此目的,可以使用包括基因产物的完整编码序列——包括所有可能存在的侧翼序列——的DNA分子,也可以使用仅含有部分编码序列的DNA分子,但是所述部分编码序列必须足够长,以便在细胞中产生反义效果。也可以使用与所述基因产物的编码序列具有高度同源性但并不完全相同的DNA序列。
当在植物中表达核酸分子时,所合成的蛋白质可被定位至植物细胞的任何所需的区室中。然而,为了将其定位于特定区室,可以例如将编码区与确保在某一区室中定位的DNA序列相连接。这种序列是本领域中技术人员已知的(见,例如Braun et al.,EMBO J.11(1992),3219-3227;Wolter et al.,Proc.Natl.Acad.Sci.USA85(1988),846-850;Sonnewald等人,Plant J.1(1991),95-106)。核酸分子也可以在植物细胞中的细胞器中表达。
可以使用已知的技术使转基因植物细胞再生为整株植物。原则上,所述转基因植物可为任何所需的植物品种的植物,即不仅可为单子叶植物,也可为双子叶植物。
因此,可以通过对同源(即天然)基因或基因序列的过表达、阻抑或抑制,或者通过异源(即外源)基因或基因序列的表达而获得性质改变的转基因植物。
优选将本发明式(I)的化合物用于转基因作物中,所述转基因作物对生长调节剂例如2,4-D麦草畏(2,4D dicamba)具有抗性,或者对抑制必需的植物酶,例如乙酰乳酸合酶(acetolactate synthases,ALS)、5-烯醇式丙酮酰莽草酸-3-磷酸(EPSP)合酶、谷氨酰胺合酶(glutaminesynthases,GS)或羟基苯丙酮酸双加氧酶(hydroxyphenylpyruvatedioxygenases,HPPD)的除草剂具有抗性,或者对选自磺酰脲类、草甘膦类、草铵磷类或苯甲酰基异噁唑类以及类似的活性化合物的除草剂具有抗性,或对以上活性物质的任意结合物具有抗性。
特别优选地,本发明的化合物可以用于对草甘膦类和草铵磷类的结合、草甘膦类和磺酰脲类或咪唑啉酮类具有抗性的转基因作物植物。极特别优选地,本发明的化合物可以用于转基因作物,例如商品名或名称为OptimumTM GATTM的玉米或大豆(耐草甘膦乙酰乳酸合酶)。
当将本发明的活性化合物用于转基因作物时,除了可在其他作物中观察到的对于有害植物的效果之外,还经常发现施用于所述的转基因作物的特殊的效果,例如改变或特别是增宽的可以防治的杂草谱、改进的施用时可以使用的施用率、与转基因作物对其有抗性的除草剂的更良好的相容性,以及对转基因作物植物的生长和产率的影响。
本发明还涉及本发明式(I)的化合物作为除草剂用于防治转基因作物植物中的有害植物的用途。
本发明的化合物可以以常规剂型施用,所述常规剂型的形式有可湿性粉剂、乳油、可喷雾溶液剂、粉末剂或颗粒剂。因此,本发明还提供含有本发明的化合物的除草组合物和植物生长调节组合物。
根据所需的生物学和/或物理化学参数,可通过多种方式将本发明的化合物配制为制剂。可能的制剂的实例包括,例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、乳油(EC)、乳剂(EW)例如水包油乳剂和油包水乳剂、可喷雾溶液剂、悬浮浓缩剂(SC)、油基分散剂或水基分散剂、油混溶性溶液剂、胶囊悬浮剂(CS)、粉末剂(DP)、拌种产品、用于撒播和土壤施用的颗粒剂、微颗粒形式的颗粒剂(GR)、喷雾颗粒剂、包衣颗粒剂和吸附颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。这些制剂的各个类型原则上都是已知的,并在下列文献中有所描述,例如:Winnacker-Küchler,“ChemischeTechnologie”[Chemical Technology],Volume7,C.Hauser VerlagMunich,第4版,1986;Wade van Valkenburg,“PesticideFormulations”,Marcel Dekker,N.Y.,1973;K.Martens,“Spray Drying”Handbook,第3版.1979,G.Goodwin Ltd.London。
所需的制剂助剂,例如惰性物质、表面活性剂、溶剂和其他添加剂同样也是已知的,并在下列文献中有所描述,例如:Watkins,"Handbookof Insecticide Dust Diluents and Carriers",第二版,Darland Books,Caldwell N.J.;H.v.Olphen,"Introduction to Clay Colloid Chemistry";第二版,J.Wiley&Sons,N.Y.;C.Marsden,"Solvents Guide";第二版,Interscience,N.Y.1963;McCutcheon's"Detergents and EmulsifiersAnnual",MC Publ.Corp.,Ridgewood N.J.;Sisley and Wood,"Encyclopedia of Surface Active Agents",Chem.Publ.Co.Inc.,N.Y.1964;[Interface-active ethylene oxide adducts],Wiss.Verlagsgesell.,Stuttgart1976;Winnacker-Küchler,"Chemische Technologie",第7卷,C.HanserVerlag Munich,第四版,1986。
基于上述制剂,可以生产与其它农药活性物质——例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂——以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂或桶混物的形式。适当的安全剂是吡唑解草酯(mefenpyr-diethyl)、环丙磺酰胺(cyprosulfamide)、双苯噁唑酸(isoxadifen-ethyl)、解草酯(cloquintocet-mexyl)和二氯丙烯胺(dichlormid)。
可湿性粉剂为可均匀分散于水中,并且除了含有活性化合物和稀释剂或惰性物质之外,还含有离子型表面活性剂和/或非离子型表面活性剂(湿润剂、分散剂)的制剂,所述表面活性剂例如聚氧乙基化烷基酚、聚氧乙基化脂肪醇、聚氧乙基化脂肪胺、脂肪醇聚二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木素磺酸钠、2,2’-二萘基甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为了制备可湿性粉剂,例如在常规设备例如锤磨机、鼓风磨机和空气喷射磨机中将除草活性化合物磨细,并同时或随后与制剂助剂相混合。
乳油通过下述过程制备:将活性化合物溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或相对高沸点的芳香族化合物或烃类)或有机溶剂混合物中,并加入一种或多种离子型和/或非离子型表面活性剂(乳化剂)。使用的乳化剂为例如烷基芳基磺酸钙盐,例如十二烷基苯磺酸钙;或非离子型乳化剂,例如脂肪酸聚二醇酯、烷基芳基聚二醇醚、脂肪醇聚二醇醚、环氧丙烷-环氧乙烷缩合物、烷基聚醚、脱水山梨聚糖酯(例如脱水山梨聚糖脂肪酸酯)或聚氧乙烯脱水山梨聚糖酯(例如聚氧乙烯脱水山梨聚糖脂肪酸酯)。
粉剂可通过将活性化合物与细分散的固体物质研磨而制备,所述固体物质例如滑石、天然粘土(例如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮浓缩剂可为水基或油基的。它们可以通过例如使用市售的球磨机湿法研磨而制备,在制备过程中可以任选地加入上文在例如其他剂型中所述的表面活性剂。
乳剂例如水包油乳剂(EW),可以使用例如搅拌器、胶体磨机和/或静态混合器制备,使用水性有机溶剂以及任选的例如在上文其他剂型中所述的表面活性剂。
颗粒剂可以通过将所述活性化合物喷洒在能够吸附的颗粒状惰性材料上、或通过使用粘合剂将活性化合物浓缩剂施用到载体表面而制备,所述载体例如砂、高岭土或颗粒状惰性材料,所述粘合剂例如聚乙烯醇、聚丙烯酸钠或矿物油。合适的活性化合物也可以以制备肥料颗粒的常规方式——如果需要,可以与肥料相混合——而制备成颗粒。
水分散性颗粒剂通常可以通过常规方法制备,所述常规方法例如喷雾干燥法、流化床制粒法、盘式制粒法、使用高速混合器的混合法以及不使用固体惰性物质的挤出法。
关于盘式制粒、流化床制粒、挤出法制粒和喷雾法制粒,参见例如:"Spray-Drying Handbook"第三版,1979,G.Goodwin Ltd.,London;J.E.Browning,"Agglomeration",Chemical and Engineering1967,第147页及后文;"Perry's Chemical Engineer's Handbook",第5版,McGraw-Hill,New York1973,第8-57页中的方法。
关于作物保护组合物制剂的其他细节,参见例如G.C.Klingman,“Weed Control as a Science”,John Wiley and Sons.,Inc.,New York,1961,81-96页;和J.D.Freyer,S.A.Evans,“Weed Control Handbook”,第5版,Blackwell Scientific Publications,Oxford,1968,第101-103页。
所述农业化学制剂通常含有0.1至99重量%、特别地为0.1至95重量%的本发明的化合物。在可湿性粉剂中,活性化合物的浓度例如为约10至90重量%,达到100重量%的剩余部分由常规制剂成分组成。对于乳油,活性化合物的浓度可为约1至90重量%,优选地为5至80重量%。粉剂形式的制剂中含有1至30重量%的活性化合物,优选地通常含有5至20重量%的活性化合物;可喷雾溶液剂中含有约0.05至80重量%、优选地为2至50重量%的活性化合物。对于水分散性颗粒剂而言,活性化合物的含量部分地取决于所述活性化合物以液体形式还是固体形式存在,以及所使用的粒化助剂和填料等。在水分散性颗粒剂中,活性化合物的含量例如为1至95重量%,优选地为10至80重量%。
此外,所述活性化合物的制剂中任选含有各自常用的粘合剂、湿润剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填料、载体和染料、消泡剂、蒸发抑制剂和影响pH值及粘度的试剂。
基于上述制剂,也可以制备与其它农药活性物质——例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂——以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂或桶混物的形式。
可以与本发明的化合物以混合制剂或桶混形式结合使用的活性化合物为,例如,已知的基于抑制以下物质的活性化合物,所述物质是例如乙酰乳酸合酶、乙酰辅酶A羧化酶、纤维素合酶、烯醇式丙酮酰莽草酸-3-磷酸合酶、谷氨酰胺合酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光系统I、光系统II、原卟啉原氧化酶,例如记载于WeedResearch26(1986)441-445页或"The Pesticide Manual",第14版,TheBritish Crop Protection Council and the Royal Soc.of Chemistry,2006和其中引用的文献中。可以与本发明的化合物结合的已知的除草剂或植物生长调节剂是例如以下的活性物质(化合物以国际标准化组织(ISO)规定的通用名表示,或以化学名称、或其代号表示),它们总是包括其所有使用形式,例如酸、盐、酯和异构体,例如立体异构体和光学异构体。此处以示例的方式提及一种——在一些情况下多种——使用形式:
乙草胺(acetochlor)、苯并噻二唑(acibenzolar)、苯并噻二唑(acibenzolar-S-methyl)、三氟羧草醚(acifluorfen)、三氟羧草醚(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、草毒死(allidochlor)、禾草灭(alloxydim)、枯杀达(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、杀草强(amitrol)、氨基磺酸铵(ammoniumsulfamate)、环丙嘧啶醇(ancymidol)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin),四唑嘧磺隆(azimsulfurone)、叠氮津(aziprotryn)、氟丁酰草胺(beflubutamid),草除灵(benazolin)、草除灵(benazolin-ethyl)、bencarbazone、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、地散磷(bensulide)、苄嘧磺隆(bensulfuron、bensulfuron-methyl)、灭草松(bentazone)、双苯嘧草酮(benzfendizone)、双环磺草酮(benzobicyclon),吡草酮(benzofenap)、氟磺胺草(benzofluor)、新燕灵(benzoylprop)、bicyclopyrone、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠盐(bilanafos-sodium)、双草醚(bispyribac)、双草醚(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、莠谷隆(bromuron)、特克草(buminafos)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁氧环酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑酮草酯(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、甲氧除草醚(chlomethoxyfen)、草灭畏(chloramben)、chlorazifop、chlorazifop-butyl、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam)、伐草克(chlorfenac)、双氯酚酸钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurecol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、矮壮素(chlormequat-chloride)、草枯醚(chlornitrofen)、4-氯邻苯二甲酸(chlorophthalim)、氯酞酸甲酯(chlorthal-dimethyl)、绿麦隆(chlorotoluron)、氯磺隆(chlorsulfuron)、吲哚酮草酯(cinidon)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、杀雄嗪酸(clofencet)、异噁草松(clomazone)、氯甲酰草胺(clomeprop)、调果酸(cloprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环丙酰胺酸(cyclanilide)、环草敌(cycloate)、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、莎草快(cyperquat)、环丙津(cyprazine)、环唑草胺(cyprazole)、2,4-D、2,4-DB、杀草隆(daimuron/dymron)、茅草枯(dalapon)、丁酰肼(daminozide)、棉隆(dazomet)、正癸醇(n-decanol)、甜菜安(desmedipham)、敌草净(desmetryn)、detosyl-pyrazolate(DTP)、燕麦敌(diallate)、麦草畏(dicamba)、敌草腈(dichlobenil)、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸(dichlorprop-P)、二氯苯氧基丙酸(diclofop)、禾草灵(diclofop-methyl)、禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、乙酰甲草酸(diethatyl)、乙酰甲草胺(diethatyl-ethyl)、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、氟吡草腙(diflufenzopyr-sodium)、噁唑隆(dimefuron)、敌草克(dikegulac-sodium)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、甲酚噻草胺-P(dimethenamide-P)、噻节因(dimethipin)、dimetrasulfuron、氨氟灵(dinitramine)、地乐酚(dinoseb)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、异丙净(dipropetryn)、敌草快(diquat)、敌草快(diquat dibromide)、氟硫草定(dithiopyr)、敌草隆(diuron)、二硝酚(DNOC)、草止津(eglinazine-ethyl)、茵多酸(endothal)、扑草灭(EPTC)、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethamesulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙烯利(ethephon)、磺噻隆(ethidimuron)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-5331,即N-[2-氯-4-氟-5[4-(3-氟丙基)-4,5-二氢-5-氧-1H-四唑-1-基]苯基]乙磺酰胺、F-7967,即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮、2,4,5-涕丙酸(fenoprop)、噁唑禾草灵(fenoxaprop)、噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、精噁唑禾草灵(fenoxaprop-P-ethyl)、fenoxasulfone、四唑酰草胺(fentrazamide)、非草隆(fenuron)、麦草氟(flamprop)、麦草氟异丙酯(flamprop-M-isopropyl)、麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、异丙吡草酯(fluazolate)、氟唑磺隆(flucarbazone)、氟酮磺隆(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet(thiafluamide))、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、氟节胺(flumetralin)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、氟草隆(fluometuron)、三氟硝草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、氟胺草唑(flupoxam)、氟丙嘧草酯(flupropacil)、四氟丙酸(flupropanoate)、氟啶磺隆(flupyrsulfuron)、氟啶嘧磺隆(flupyrsulfuron-methyl-sodium))、抑草丁(flurenol)、芴丁酯(flurenol-butyl)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟草烟(fluroxypyr)、甲基庚酯(fluroxypyr-meptyl)、呋嘧醇(flurprimidol)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、氟噻乙草酯(fluthiacet-methyl)、噻唑草酰胺(fluthiamide)、氟磺胺草醚(fomesafen)、甲酰氨磺隆(foramsulfuron)、氯吡脲(forchlorfenuron)、杀木膦(fosamine)、呋氧草醚(furyloxyfen)、赤霉素(gibberillic acid)、草铵膦(glufosinate)、草铵磷(glufosinate-ammonium)、精草铵膦(glufosinate-P)、精草铵磷(glufosinate-P-ammonium)、glufosinate-P-sodium、草甘膦(glyphosate)、草甘膦异丙胺盐(glyphosate-isopropylammonium)、H-9201,即O-(2,4-二甲基-6-硝基苯基)-O-乙基-异丙基硫代磷酰胺、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氯氟乙禾灵(haloxyfop-ethoxyethyl)、氯氟乙禾灵(haloxyfop-P-ethoxyethyl)、氟吡甲禾灵(haloxyfop-methyl)、氟吡甲禾灵(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02,即(2,4-二氯苯氧基)乙酸1-(二甲氧基磷酰基)-乙基酯、咪草酸(imazamethabenz)、咪草酸(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、铵基咪草啶酸(imazamox-ammonium)、甲咪唑烟酸(imazapic)、咪唑烟酸(imazapyr)、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵(imazaquin-ammonium)、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸铵(imazethapyr-ammonium)、咪唑乙烟酸异丙基胺盐(imazethapyr-isopropylammonium)、唑吡嘧磺隆(imazosulfuron)、抗倒胺(inabenfide)、茚草酮(indanofan)、碘甲磺隆(indaziflam)、吲哚乙酸(indoleacetic acid(IAA))、4-吲哚-3-基丁酸(IBA)、碘甲磺隆钠盐(iodosulfuron)、碘甲磺隆钠盐(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、三哇苯胺除草剂(ipfencarbazone)、丁脒酰胺(isocarbamid)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异噁隆(isouron)、异噁酰草胺(isoxaben)、异噁氯草酮(isoxachlortole)、异噁唑草酮(isoxaflutole)、异噁草醚(isoxapyrifop)、KUH-043,即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-噁唑、特胺灵(karbutilate)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、马来酰肼(maleic hydrazide)、MCPA、MCPB、MCPB甲酯(MCPB-methyl)、MCPB乙酯(MCPB-ethyl)和MCPB钠(MCPB-sodium)、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠(mecoprop-sodium)、2甲4氯丙酸丁氧酯(mecoprop-butotyl)、2甲4氯丙酸丁氧酯(mecoprop-P-butotyl)、高2甲4氯丙酸二甲氨(mecoprop-P-dimethylammonium)、高2甲4氯丙酸2-乙基己酯(mecoprop-P-2-ethylhexyl)、高2甲4氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidide)、甲哌啶(mepiquat chloride)、甲磺胺磺隆(mesosulfuron)、甲磺胺磺隆(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、灭草唑(methazole)、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、苯草酮(methoxyphenone)、甲基杀草隆(methyldymron)、1-甲基环丙烯(1-methylcyclopropene)、异硫氰酸甲酯(methyl isothiocyanate)、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、庚酰草胺(monalide)、单脲(monocarbamide)、甲酰胺硫酸盐(monocarbamide dihydrogensulfate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-ester)、灭草隆(monuron)、MT128,即6-氯-N-[(2E)-3-氯丙-2-烯-1-基]-5-甲基-N-苯基哒嗪-3-胺、MT-5950,即N-[3-氯-4-(1-甲基乙基)苯基]2-甲基戊酰胺、NGGC-011、萘丙胺(naproanilide)、敌草胺(napropamide)、萘草胺(naptalam)、NC310,即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen)、复硝酚钠(nitrophenolate-sodium(异构体混合物))、硝氟草醚(nitrofluorfen)、正壬酸(nonanoic acid)、氟草敏(norflurazon)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、多效唑(paclobutrazol)、百草枯(paraquat)、百草枯(paraquat dichloride)、壬酸(pelargonic acid(nonanoic acid))、二甲戊灵(pendimethalin)、4-(叔丁基)-N-(1-乙基-丙基)-2,6-二硝基-苯胺(pendralin)、五氟磺草胺(penoxsulam)、甲氯酰草胺(pentanochlor)、环戊噁草酮(pentoxazone)、黄草伏(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、甜菜宁-乙酯(phenmedipham-ethyl)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、pirifenop、pirifenop-butyl、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆(primisulfuron-methyl)、烯丙苯噻唑(probenazole)、氟唑草胺(profluazole)、环丙氰津(procyazine)、氨氟乐灵(prodiamine)、环丙氟灵(profluralin)、环苯草酮(profoxydim)、调环酸(prohexadione)、调环酸(prohexadione-calcium)、茉莉酮(prohydrojasmon)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、噁草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、嗪咪唑嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、丙炔草胺(prynachlor)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚(pyraflufen-ethyl)、pyrasulfotole、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron、pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、异丙酯草醚(pyribambenz)、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、达草止(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚(pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、嘧草硫醚(pyrithiobac-sodium)、异噁草酮(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinchlorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、仲丁通(secbumeton)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SN-106279,即(2R)-2({7-[2-氯-4-(三氟甲基)苯氧基]-2-萘基}氧代)丙酸甲酯、磺草酮(sulcotrione)、草克死(sulfallate(CDEC))、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、草硫膦(sulfosate(glyphosate-trimesium))、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249,即5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基酯、SYP-300,即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫代咪唑烷-4,5-二酮、牧草胺(tebutam)、丁噻隆(tebuthiuron)、四氯硝基苯(tecnazene)、tefuryltrione、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、特丁通(terbumeton)、特丁津(terbuthylazine)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、氟噻草胺(thiafluamide)、噻氟隆(thiazafluron)、噻唑烟酸(thiazopyr)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、异草唑酮(thiencarbazone)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、野燕畏(triallate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、triazofenamide、苯磺隆(tribenuron)、苯磺隆(tribenuron-methyl)、三氯乙酸(trichloroacetic acid(TCA)),三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆(trifloxysulfuron-sodium)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、三甲隆(trimeturon)、抗倒酯(trinexapac)、抗倒酯(trinexapac-ethyl)、三氟甲磺隆(tritosulfuron)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)、灭草敌(vernolate)、ZJ-0862,即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧代]苄基}苯胺和以下化合物。
为了应用,以市售形式存在的制剂,如果合适,以常规的方式稀释,例如在可湿性粉剂、乳油、分散剂和水分散性颗粒剂的情况下,用水稀释。粉末剂、适于土壤施用的颗粒剂或适于撒播的颗粒剂和可喷雾溶液剂形式的制剂通常在施用前不再用其他惰性物质稀释。
通式(I)的化合物所需的施用率根据外界条件而有所不同,所述条件例如特别是温度、湿度和所用的除草剂类型。所述施用率可以在很宽的范围内变化,例如0.001至1.0kg/ha或更多的活性物质;然而,优选0.005至750g/ha。
下述实施例示例说明本发明:
A.化学实施例
3-(-2-甲基-3-甲基亚磺酰基-4-五氟乙基)苯甲酰基)双环[3.2.1]辛烷-2,4-二酮的制备(表中实施例编号1-153)
步骤1:3-氟-4-(五氟乙基)溴苯的合成
将13.2g(91.9mmol)溴化铜(I)在80ml无水N,N二甲基甲酰胺中冷却至-5℃。在氮气下,加入14.7g(76.7mmol)三甲基-(五氟乙基)硅烷。以一定的速率在30分钟的过程中分批加入4.45g(76.7mmol)氟化钾(喷雾干燥的),使得内部温度保持低于0℃。将该混合物在0℃下搅拌1小时,然后在12小时的过程中温热至20℃。之后加入10ml无水1,3-二甲基-2-咪唑啉酮和22g(73.1mmol)3-氟-4-碘-溴苯。将内容物在75℃下搅拌14小时。然后,蒸馏除去所有的挥发性成分至干燥,在液氮冷却的冷阱中收集馏出物。馏出物随后温热至20℃,并溶解在500ml乙醚中。该溶液用100ml水洗涤四次,然后用100ml饱和的NaCl水溶液洗涤两次。然后将有机相干燥,并在维格罗分馏柱上除去溶剂。随后在维格罗分馏柱上蒸馏残余物,得到16.1g纯度为99重量%的产物(沸点:86-87℃(75mm汞柱))。
步骤2:3-氟-4-(五氟乙基)苯甲酸的合成
将16.0g(99重量%;54.1mmol)3-氟-4-(五氟乙基)-溴苯在110ml四氢呋喃中的溶液冷却至-10℃。在30分钟的过程中逐滴加入36.8ml的2M(73.6mmol)异丙基氯化镁溶液。将该混合物在-10℃下搅拌2.5小时,然后将该混合物小心倒至过量的干冰中。然后,加入130ml水,并随后将混合物用10ml乙醚萃取一次。水相用半浓缩的盐酸酸化,然后用150ml乙醚萃取四次。合并的有机相被干燥,且溶剂从滤液中除去。将残余物用氯仿重结晶,得到10.7g纯度为98重量%的产物。
步骤3:3-氟-2-甲基-4-(五氟乙基)苯甲酸的合成
将5.00g(98重量%;19.0mmol)3-氟-4-(五氟乙基)苯甲酸加入至40ml无水四氢呋喃中。加入4.73g(40.7mmol)1,2-二(二甲基氨基)乙烷,然后将混合物冷却至-40℃。然后,16.3ml的2.5M正丁基锂的己烷溶液(40.7mmol)以一定的速率逐滴加入,使得温度在-33℃至-35℃的范围内。内容物在-35℃的温度下搅拌4小时。然后逐滴加入8.25g(58.1mmol)碘代甲烷在10ml无水四氢呋喃中的溶液,并且混合物在-35℃的温度下搅拌1小时。之后,将内容物温热至室温(RT),并在该温度下搅拌16小时。对于后处理,小心地加入50ml的2M盐酸,然后水相用乙醚萃取。将合并的有机相干燥,用旋转蒸发器移除溶剂。残余物在正庚烷中搅拌,然后过滤。这得到了作为干净产品的2.33g残余物。将滤液中的溶剂除去,残余物再在正庚烷中搅拌。过滤产生590mg残余物,鉴定为纯度为70重量%的产物。
步骤4:3-氟-2-甲基-4-(五氟乙基)苯甲酸甲酯的合成
将2.33g(8.56mmol)3-氟-2-甲基-4-(五氟乙基)苯甲酸引入至30ml甲醇中,并与2ml浓硫酸混合。随后将混合物加热回流直至通过HPLC表明完全转化。将内容物在旋转蒸发器上除去溶剂,并将残余物溶于水。该混合物用乙酸乙酯萃取两次,合并的有机相用饱和碳酸氢钠水溶液洗涤一次。将有机相干燥并除去溶剂。所得的残余物为2.1g干净产品。
步骤5:2-甲基-3-(甲硫基)-4-(五氟乙基)苯甲酸甲酯的合成
将2.1g(7.34mmol)3-氟-2-甲基-4-(五氟乙基)苯甲酸甲酯引入至20mlDMF中,然后与758mg(95重量%;10.3mmol)的甲硫醇钠混合。该混合物在室温下搅拌2小时,然后除去溶剂。将残余物溶于乙酸乙酯和水中,水相用乙酸乙酯萃取两次,并且,最后,将合并的有机相干燥,并除去溶剂。将残余物通过色谱法纯化,得到1.28g干净产品。
步骤6:2-甲基-3-(甲硫基)-4-(五氟乙基)苯甲酸的合成
(编号6-145)
将530mg(1.69mmol)2-甲基-3-(甲硫基)-4-(五氟乙基)苯甲酸甲酯引入至10ml甲醇中,并与0.5ml的20%浓度的氢氧化钠水溶液混合。将内容物在室温下搅拌,直至通过薄层色谱法监测反应表明完全转化。从混合物中除去溶剂,并将残余物溶于少量的水。混合物用1M盐酸酸化,然后搅拌5分钟,最后过滤。所得的残余物为470mg干净产品。
步骤7:2-甲基-3-甲硫基-4-(五氟乙基)苯甲酸4-氧代双环[3.2.1]辛-2-烯-2-基酯的合成
将235mg(0.783mmol)2-甲基-3-(甲硫基)-4-(五氟乙基)苯甲酸引入至20ml无水二氯甲烷中,并依次与129mg(1.02mmol)草酰氯以及两滴N,N-二甲基甲酰胺混合。在气体释放结束后,将混合物在回流下再加热10分钟。然后,将内容物冷却,并用旋转蒸发器浓缩。将残余物溶于20ml无水二氯甲烷中,并与119mg(0.861mmol)双环[3.2.1]辛烷-2,4-二酮和催化量的DMAP混合。然后逐滴加入158mg(1.57mmol)三乙胺。将该混合物在室温下搅拌16小时。对于后处理,加入3ml的1N盐酸。相分离之后,将有机相除去溶剂,并且残余物最后通过色谱法纯化。这得到了纯度为90重量%的280mg产物。
步骤8:2-甲基-3-甲基亚磺酰基-4-五氟乙基苯甲酸4-氧代双环[3.2.1]辛-2-烯-2-基酯的合成
将280mg(90重量%;0.599mmol)2-甲基-3-甲硫基-4-五氟乙基苯甲酸4-氧代双环[3.2.1]辛-2-烯-2-基酯引入至20ml二氯甲烷中,并与134mg(77重量%;0.599mmol)间氯过氧苯甲酸混合。将该混合物在室温下搅拌,直至通过薄层色谱法监测反应表明转化完全。对于后处理,将内容物用10%浓度的亚硫酸氢钠水溶液洗涤一次,然后用饱和碳酸氢钠水溶液洗涤两次。最后,将有机相除去溶剂。作为残余物,纯度为95重量%的250mg产物被回收。
步骤9:3-(2’-甲基-3-甲基亚磺酰基-4-五氟乙基苯甲酰基)双环[3.2.1]辛烷-2,4-二酮的合成(编号1-153)
将250mg(95重量%;0.544mmol)2-甲基-3-甲基亚磺酰基-4-五氟乙基苯甲酸4-氧代双环[3.2.1]辛-2-烯-2-基酯引入至15ml乙腈中,并依次与110mg(1.09mmol)三乙胺,和催化量的氰化钾,以及8滴三甲基氰硅烷混合。将该混合物在室温下搅拌16小时。对于后处理,对内容物进行浓缩,并将残余物溶于15ml二氯甲烷中。混合物与3ml的1M HCl混合,并在相分离后,将有机相除去溶剂。残余物最后通过色谱法纯化,这得到了纯度为95重量%的86.4mg产物。
在下表中列举的实施例通过与上述方法类似的方法制得,或可以通过与上述方法类似的方法获得。这些化合物是极特别优选的。
所用的简写具有以下含义:
Bu=丁基 Et=乙基 Me=甲基 Pr=丙基
i=异 s=仲 t=叔 Ph=苯基
表1:本发明的式(I)的化合物,其中R2为羟基,A为(CH2)且Z为(CH2)2,且R3和R4各自为氢
表2:本发明的式(I)的化合物,其中R2为羟基,A为氧,Z为(CH2)2,R3为甲基且R4为氢
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-1 | Me | Me | 0 | CF2Cl | |
2-2 | Me | Et | 0 | CF2Cl | |
2-3 | Me | n-Pr | 0 | CF2Cl | |
2-4 | Me | i-Pr | 0 | CF2Cl | |
2-5 | Me | n-Bu | 0 | CF2Cl | |
2-6 | Me | i-Bu | 0 | CF2Cl | |
2-7 | Me | s-Bu | 0 | CF2Cl | |
2-8 | Me | t-Bu | 0 | CF2Cl | |
2-9 | Me | Me | 1 | CF2Cl | |
2-10 | Me | Et | 1 | CF2Cl | |
2-11 | Me | n-Pr | 1 | CF2Cl | |
2-12 | Me | i-Pr | 1 | CF2Cl | |
2-13 | Me | n-Bu | 1 | CF2Cl | |
2-14 | Me | i-Bu | 1 | CF2Cl | |
2-15 | Me | s-Bu | 1 | CF2Cl | |
2-16 | Me | t-Bu | 1 | CF2Cl | |
2-17 | Me | Me | 2 | CF2Cl | |
2-18 | Me | Et | 2 | CF2Cl | |
2-19 | Me | n-Pr | 2 | CF2Cl | |
2-20 | Me | i-Pr | 2 | CF2Cl | |
2-21 | Me | n-Bu | 2 | CF2Cl | |
2-22 | Me | i-Bu | 2 | CF2Cl | |
2-23 | Me | s-Bu | 2 | CF2Cl | |
2-24 | Me | t-Bu | 2 | CF2Cl | |
2-25 | Et | Me | 0 | CF2Cl |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-26 | Et | Et | 0 | CF2Cl | |
2-27 | Et | n-Pr | 0 | CF2Cl | |
2-28 | Et | i-Pr | 0 | CF2Cl | |
2-29 | Et | n-Bu | 0 | CF2Cl | |
2-30 | Et | i-Bu | 0 | CF2Cl | |
2-31 | Et | s-Bu | 0 | CF2Cl | |
2-32 | Et | t-Bu | 0 | CF2Cl | |
2-33 | Et | Me | 1 | CF2Cl | |
2-34 | Et | Et | 1 | CF2Cl | |
2-35 | Et | n-Pr | 1 | CF2Cl | |
2-36 | Et | i-Pr | 1 | CF2Cl | |
2-37 | Et | n-Bu | 1 | CF2Cl | |
2-38 | Et | i-Bu | 1 | CF2Cl | |
2-39 | Et | s-Bu | 1 | CF2Cl | |
2-40 | Et | t-Bu | 1 | CF2Cl | |
2-41 | Et | Me | 2 | CF2Cl | |
2-42 | Et | Et | 2 | CF2Cl | |
2-43 | Et | n-Pr | 2 | CF2Cl | |
2-44 | Et | i-Pr | 2 | CF2Cl | |
2-45 | Et | n-Bu | 2 | CF2Cl | |
2-46 | Et | i-Bu | 2 | CF2Cl | |
2-47 | Et | s-Bu | 2 | CF2Cl | |
2-48 | Et | t-Bu | 2 | CF2Cl | |
2-49 | Me | Me | 0 | CFCl2 | |
2-50 | Me | Et | 0 | CFCl2 | |
2-51 | Me | n-Pr | 0 | CFCl2 | |
2-52 | Me | i-Pr | 0 | CFCl2 | |
2-53 | Me | n-Bu | 0 | CFCl2 | |
2-54 | Me | i-Bu | 0 | CFCl2 | |
2-55 | Me | s-Bu | 0 | CFCl2 | |
2-56 | Me | t-Bu | 0 | CFCl2 | |
2-57 | Me | Me | 1 | CFCl2 | |
2-58 | Me | Et | 1 | CFCl2 | |
2-59 | Me | n-Pr | 1 | CFCl2 | |
2-60 | Me | i-Pr | 1 | CFCl2 | |
2-61 | Me | n-Bu | 1 | CFCl2 | |
2-62 | Me | i-Bu | 1 | CFCl2 | |
2-63 | Me | s-Bu | 1 | CFCl2 | |
2-64 | Me | t-Bu | 1 | CFCl2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-65 | Me | Me | 2 | CFCl2 | |
2-66 | Me | Et | 2 | CFCl2 | |
2-67 | Me | n-Pr | 2 | CFCl2 | |
2-68 | Me | i-Pr | 2 | CFCl2 | |
2-69 | Me | n-Bu | 2 | CFCl2 | |
2-70 | Me | i-Bu | 2 | CFCl2 | |
2-71 | Me | s-Bu | 2 | CFCl2 | |
2-72 | Me | t-Bu | 2 | CFCl2 | |
2-73 | Et | Me | 0 | CFCl2 | |
2-74 | Et | Et | 0 | CFCl2 | |
2-75 | Et | n-Pr | 0 | CFCl2 | |
2-76 | Et | i-Pr | 0 | CFCl2 | |
2-77 | Et | n-Bu | 0 | CFCl2 | |
2-78 | Et | i-Bu | 0 | CFCl2 | |
2-79 | Et | s-Bu | 0 | CFCl2 | |
2-80 | Et | t-Bu | 0 | CFCl2 | |
2-81 | Et | Me | 1 | CFCl2 | |
2-82 | Et | Et | 1 | CFCl2 | |
2-83 | Et | n-Pr | 1 | CFCl2 | |
2-84 | Et | i-Pr | 1 | CFCl2 | |
2-85 | Et | n-Bu | 1 | CFCl2 | |
2-86 | Et | i-Bu | 1 | CFCl2 | |
2-87 | Et | s-Bu | 1 | CFCl2 | |
2-88 | Et | t-Bu | 1 | CFCl2 | |
2-89 | Et | Me | 2 | CFCl2 | |
2-90 | Et | Et | 2 | CFCl2 | |
2-91 | Et | n-Pr | 2 | CFCl2 | |
2-92 | Et | i-Pr | 2 | CFCl2 | |
2-93 | Et | n-Bu | 2 | CFCl2 | |
2-94 | Et | i-Bu | 2 | CFCl2 | |
2-95 | Et | s-Bu | 2 | CFCl2 | |
2-96 | Et | t-Bu | 2 | CFCl2 | |
2-97 | Me | Me | 0 | CCl3 | |
2-98 | Me | Et | 0 | CCl3 | |
2-99 | Me | n-Pr | 0 | CCl3 | |
2-100 | Me | i-Pr | 0 | CCl3 | |
2-101 | Me | n-Bu | 0 | CCl3 | |
2-102 | Me | i-Bu | 0 | CCl3 | |
2-103 | Me | s-Bu | 0 | CCl3 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-104 | Me | t-Bu | 0 | CCl3 | |
2-105 | Me | Me | 1 | CCl3 | |
2-106 | Me | Et | 1 | CCl3 | |
2-107 | Me | n-Pr | 1 | CCl3 | |
2-108 | Me | i-Pr | 1 | CCl3 | |
2-109 | Me | n-Bu | 1 | CCl3 | |
2-110 | Me | i-Bu | 1 | CCl3 | |
2-111 | Me | s-Bu | 1 | CCl3 | |
2-112 | Me | t-Bu | 1 | CCl3 | |
2-113 | Me | Me | 2 | CCl3 | |
2-114 | Me | Et | 2 | CCl3 | |
2-115 | Me | n-Pr | 2 | CCl3 | |
2-116 | Me | i-Pr | 2 | CCl3 | |
2-117 | Me | n-Bu | 2 | CCl3 | |
2-118 | Me | i-Bu | 2 | CCl3 | |
2-119 | Me | s-Bu | 2 | CCl3 | |
2-120 | Me | t-Bu | 2 | CCl3 | |
2-121 | Et | Me | 0 | CCl3 | |
2-122 | Et | Et | 0 | CCl3 | |
2-123 | Et | n-Pr | 0 | CCl3 | |
2-124 | Et | i-Pr | 0 | CCl3 | |
2-125 | Et | n-Bu | 0 | CCl3 | |
2-126 | Et | i-Bu | 0 | CCl3 | |
2-127 | Et | s-Bu | 0 | CCl3 | |
2-128 | Et | t-Bu | 0 | CCl3 | |
2-129 | Et | Me | 1 | CCl3 | |
2-130 | Et | Et | 1 | CCl3 | |
2-131 | Et | n-Pr | 1 | CCl3 | |
2-132 | Et | i-Pr | 1 | CCl3 | |
2-133 | Et | n-Bu | 1 | CCl3 | |
2-134 | Et | i-Bu | 1 | CCl3 | |
2-135 | Et | s-Bu | 1 | CCl3 | |
2-136 | Et | t-Bu | 1 | CCl3 | |
2-137 | Et | Me | 2 | CCl3 | |
2-138 | Et | Et | 2 | CCl3 | |
2-139 | Et | n-Pr | 2 | CCl3 | |
2-140 | Et | i-Pr | 2 | CCl3 | |
2-141 | Et | n-Bu | 2 | CCl3 | |
2-142 | Et | i-Bu | 2 | CCl3 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-143 | Et | s-Bu | 2 | CCl3 | |
2-144 | Et | t-Bu | 2 | CCl3 | |
2-145 | Me | Me | 0 | C2F5 | |
2-146 | Me | Et | 0 | C2F5 | |
2-147 | Me | n-Pr | 0 | C2F5 | |
2-148 | Me | i-Pr | 0 | C2F5 | |
2-149 | Me | n-Bu | 0 | C2F5 | |
2-150 | Me | i-Bu | 0 | C2F5 | |
2-151 | Me | s-Bu | 0 | C2F5 | |
2-152 | Me | t-Bu | 0 | C2F5 | |
2-153 | Me | Me | 1 | C2F5 | |
2-154 | Me | Et | 1 | C2F5 | |
2-155 | Me | n-Pr | 1 | C2F5 | |
2-156 | Me | i-Pr | 1 | C2F5 | |
2-157 | Me | n-Bu | 1 | C2F5 | |
2-158 | Me | i-Bu | 1 | C2F5 | |
2-159 | Me | s-Bu | 1 | C2F5 | |
2-160 | Me | t-Bu | 1 | C2F5 | |
2-161 | Me | Me | 2 | C2F5 | |
2-162 | Me | Et | 2 | C2F5 | |
2-163 | Me | n-Pr | 2 | C2F5 | |
2-164 | Me | i-Pr | 2 | C2F5 | |
2-165 | Me | n-Bu | 2 | C2F5 | |
2-166 | Me | i-Bu | 2 | C2F5 | |
2-167 | Me | s-Bu | 2 | C2F5 | |
2-168 | Me | t-Bu | 2 | C2F5 | |
2-169 | Et | Me | 0 | C2F5 | |
2-170 | Et | Et | 0 | C2F5 | |
2-171 | Et | n-Pr | 0 | C2F5 | |
2-172 | Et | i-Pr | 0 | C2F5 | |
2-173 | Et | n-Bu | 0 | C2F5 | |
2-174 | Et | i-Bu | 0 | C2F5 | |
2-175 | Et | s-Bu | 0 | C2F5 | |
2-176 | Et | t-Bu | 0 | C2F5 | |
2-177 | Et | Me | 1 | C2F5 | |
2-178 | Et | Et | 1 | C2F5 | |
2-179 | Et | n-Pr | 1 | C2F5 | |
2-180 | Et | i-Pr | 1 | C2F5 | |
2-181 | Et | n-Bu | 1 | C2F5 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-182 | Et | i-Bu | 1 | C2F5 | |
2-183 | Et | s-Bu | 1 | C2F5 | |
2-184 | Et | t-Bu | 1 | C2F5 | |
2-185 | Et | Me | 2 | C2F5 | |
2-186 | Et | Et | 2 | C2F5 | |
2-187 | Et | n-Pr | 2 | C2F5 | |
2-188 | Et | i-Pr | 2 | C2F5 | |
2-189 | Et | n-Bu | 2 | C2F5 | |
2-190 | Et | i-Bu | 2 | C2F5 | |
2-191 | Et | s-Bu | 2 | C2F5 | |
2-192 | Et | t-Bu | 2 | C2F5 | |
2-193 | Me | Me | 0 | CF(CF3)2 | |
2-194 | Me | Et | 0 | CF(CF3)2 | |
2-195 | Me | n-Pr | 0 | CF(CF3)2 | |
2-196 | Me | i-Pr | 0 | CF(CF3)2 | |
2-197 | Me | n-Bu | 0 | CF(CF3)2 | |
2-198 | Me | i-Bu | 0 | CF(CF3)2 | |
2-199 | Me | s-Bu | 0 | CF(CF3)2 | |
2-200 | Me | t-Bu | 0 | CF(CF3)2 | |
2-201 | Me | Me | 1 | CF(CF3)2 | |
2-202 | Me | Et | 1 | CF(CF3)2 | |
2-203 | Me | n-Pr | 1 | CF(CF3)2 | |
2-204 | Me | i-Pr | 1 | CF(CF3)2 | |
2-205 | Me | n-Bu | 1 | CF(CF3)2 | |
2-206 | Me | i-Bu | 1 | CF(CF3)2 | |
2-207 | Me | s-Bu | 1 | CF(CF3)2 | |
2-208 | Me | t-Bu | 1 | CF(CF3)2 | |
2-209 | Me | Me | 2 | CF(CF3)2 | |
2-210 | Me | Et | 2 | CF(CF3)2 | |
2-211 | Me | n-Pr | 2 | CF(CF3)2 | |
2-212 | Me | i-Pr | 2 | CF(CF3)2 | |
2-213 | Me | n-Bu | 2 | CF(CF3)2 | |
2-214 | Me | i-Bu | 2 | CF(CF3)2 | |
2-215 | Me | s-Bu | 2 | CF(CF3)2 | |
2-216 | Me | t-Bu | 2 | CF(CF3)2 | |
2-217 | Et | Me | 0 | CF(CF3)2 | |
2-218 | Et | Et | 0 | CF(CF3)2 | |
2-219 | Et | n-Pr | 0 | CF(CF3)2 | |
2-220 | Et | i-Pr | 0 | CF(CF3)2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-221 | Et | n-Bu | 0 | CF(CF3)2 | |
2-222 | Et | i-Bu | 0 | CF(CF3)2 | |
2-223 | Et | s-Bu | 0 | CF(CF3)2 | |
2-224 | Et | t-Bu | 0 | CF(CF3)2 | |
2-225 | Et | Me | 1 | CF(CF3)2 | |
2-226 | Et | Et | 1 | CF(CF3)2 | |
2-227 | Et | n-Pr | 1 | CF(CF3)2 | |
2-228 | Et | i-Pr | 1 | CF(CF3)2 | |
2-229 | Et | n-Bu | 1 | CF(CF3)2 | |
2-230 | Et | i-Bu | 1 | CF(CF3)2 | |
2-231 | Et | s-Bu | 1 | CF(CF3)2 | |
2-232 | Et | t-Bu | 1 | CF(CF3)2 | |
2-233 | Et | Me | 2 | CF(CF3)2 | |
2-234 | Et | Et | 2 | CF(CF3)2 | |
2-235 | Et | n-Pr | 2 | CF(CF3)2 | |
2-236 | Et | i-Pr | 2 | CF(CF3)2 | |
2-237 | Et | n-Bu | 2 | CF(CF3)2 | |
2-238 | Et | i-Bu | 2 | CF(CF3)2 | |
2-239 | Et | s-Bu | 2 | CF(CF3)2 | |
2-240 | Et | t-Bu | 2 | CF(CF3)2 | |
2-241 | Me | Me | 0 | CHF2 | |
2-242 | Me | Et | 0 | CHF2 | |
2-243 | Me | n-Pr | 0 | CHF2 | |
2-244 | Me | i-Pr | 0 | CHF2 | |
2-245 | Me | n-Bu | 0 | CHF2 | |
2-246 | Me | i-Bu | 0 | CHF2 | |
2-247 | Me | s-Bu | 0 | CHF2 | |
2-248 | Me | t-Bu | 0 | CHF2 | |
2-249 | Me | Me | 1 | CHF2 | |
2-250 | Me | Et | 1 | CHF2 | |
2-251 | Me | n-Pr | 1 | CHF2 | |
2-252 | Me | i-Pr | 1 | CHF2 | |
2-253 | Me | n-Bu | 1 | CHF2 | |
2-254 | Me | i-Bu | 1 | CHF2 | |
2-255 | Me | s-Bu | 1 | CHF2 | |
2-256 | Me | t-Bu | 1 | CHF2 | |
2-257 | Me | Me | 2 | CHF2 | |
2-258 | Me | Et | 2 | CHF2 | |
2-259 | Me | n-Pr | 2 | CHF2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
2-260 | Me | i-Pr | 2 | CHF2 | |
2-261 | Me | n-Bu | 2 | CHF2 | |
2-262 | Me | i-Bu | 2 | CHF2 | |
2-263 | Me | s-Bu | 2 | CHF2 | |
2-264 | Me | t-Bu | 2 | CHF2 | |
2-265 | Et | Me | 0 | CHF2 | |
2-266 | Et | Et | 0 | CHF2 | |
2-267 | Et | n-Pr | 0 | CHF2 | |
2-268 | Et | i-Pr | 0 | CHF2 | |
2-269 | Et | n-Bu | 0 | CHF2 | |
2-270 | Et | i-Bu | 0 | CHF2 | |
2-271 | Et | s-Bu | 0 | CHF2 | |
2-272 | Et | t-Bu | 0 | CHF2 | |
2-273 | Et | Me | 1 | CHF2 | |
2-274 | Et | Et | 1 | CHF2 | |
2-275 | Et | n-Pr | 1 | CHF2 | |
2-276 | Et | i-Pr | 1 | CHF2 | |
2-277 | Et | n-Bu | 1 | CHF2 | |
2-278 | Et | i-Bu | 1 | CHF2 | |
2-279 | Et | s-Bu | 1 | CHF2 | |
2-280 | Et | t-Bu | 1 | CHF2 | |
2-281 | Et | Me | 2 | CHF2 | |
2-282 | Et | Et | 2 | CHF2 | |
2-283 | Et | n-Pr | 2 | CHF2 | |
2-284 | Et | i-Pr | 2 | CHF2 | |
2-285 | Et | n-Bu | 2 | CHF2 | |
2-286 | Et | i-Bu | 2 | CHF2 | |
2-287 | Et | s-Bu | 2 | CHF2 | |
2-288 | Et | t-Bu | 2 | CHF2 |
表3:本发明的式(I)的化合物,其中R2为苯硫基,A为(CH2),Z为(CH2)2,且R3和R4各自为氢
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-1 | Me | Me | 0 | CF2Cl | |
3-2 | Me | Et | 0 | CF2Cl | |
3-3 | Me | n-Pr | 0 | CF2Cl | |
3-4 | Me | i-Pr | 0 | CF2Cl | |
3-5 | Me | n-Bu | 0 | CF2Cl | |
3-6 | Me | i-Bu | 0 | CF2Cl | |
3-7 | Me | s-Bu | 0 | CF2Cl | |
3-8 | Me | t-Bu | 0 | CF2Cl | |
3-9 | Me | Me | 1 | CF2Cl | |
3-10 | Me | Et | 1 | CF2Cl | |
3-11 | Me | n-Pr | 1 | CF2Cl | |
3-12 | Me | i-Pr | 1 | CF2Cl | |
3-13 | Me | n-Bu | 1 | CF2Cl | |
3-14 | Me | i-Bu | 1 | CF2Cl | |
3-15 | Me | s-Bu | 1 | CF2Cl | |
3-16 | Me | t-Bu | 1 | CF2Cl | |
3-17 | Me | Me | 2 | CF2Cl | |
3-18 | Me | Et | 2 | CF2Cl | |
3-19 | Me | n-Pr | 2 | CF2Cl | |
3-20 | Me | i-Pr | 2 | CF2Cl | |
3-21 | Me | n-Bu | 2 | CF2Cl | |
3-22 | Me | i-Bu | 2 | CF2Cl | |
3-23 | Me | s-Bu | 2 | CF2Cl | |
3-24 | Me | t-Bu | 2 | CF2Cl | |
3-25 | Et | Me | 0 | CF2Cl | |
3-26 | Et | Et | 0 | CF2Cl | |
3-27 | Et | n-Pr | 0 | CF2Cl | |
3-28 | Et | i-Pr | 0 | CF2Cl | |
3-29 | Et | n-Bu | 0 | CF2Cl | |
3-30 | Et | i-Bu | 0 | CF2Cl |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-31 | Et | s-Bu | 0 | CF2Cl | |
3-32 | Et | t-Bu | 0 | CF2Cl | |
3-33 | Et | Me | 1 | CF2Cl | |
3-34 | Et | Et | 1 | CF2Cl | |
3-35 | Et | n-Pr | 1 | CF2Cl | |
3-36 | Et | i-Pr | 1 | CF2Cl | |
3-37 | Et | n-Bu | 1 | CF2Cl | |
3-38 | Et | i-Bu | 1 | CF2Cl | |
3-39 | Et | s-Bu | 1 | CF2Cl | |
3-40 | Et | t-Bu | 1 | CF2Cl | |
3-41 | Et | Me | 2 | CF2Cl | |
3-42 | Et | Et | 2 | CF2Cl | |
3-43 | Et | n-Pr | 2 | CF2Cl | |
3-44 | Et | i-Pr | 2 | CF2Cl | |
3-45 | Et | n-Bu | 2 | CF2Cl | |
3-46 | Et | i-Bu | 2 | CF2Cl | |
3-47 | Et | s-Bu | 2 | CF2Cl | |
3-48 | Et | t-Bu | 2 | CF2Cl | |
3-49 | Me | Me | 0 | CFCl2 | |
3-50 | Me | Et | 0 | CFCl2 | |
3-51 | Me | n-Pr | 0 | CFCl2 | |
3-52 | Me | i-Pr | 0 | CFCl2 | |
3-53 | Me | n-Bu | 0 | CFCl2 | |
3-54 | Me | i-Bu | 0 | CFCl2 | |
3-55 | Me | s-Bu | 0 | CFCl2 | |
3-56 | Me | t-Bu | 0 | CFCl2 | |
3-57 | Me | Me | 1 | CFCl2 | |
3-58 | Me | Et | 1 | CFCl2 | |
3-59 | Me | n-Pr | 1 | CFCl2 | |
3-60 | Me | i-Pr | 1 | CFCl2 | |
3-61 | Me | n-Bu | 1 | CFCl2 | |
3-62 | Me | i-Bu | 1 | CFCl2 | |
3-63 | Me | s-Bu | 1 | CFCl2 | |
3-64 | Me | t-Bu | 1 | CFCl2 | |
3-65 | Me | Me | 2 | CFCl2 | |
3-66 | Me | Et | 2 | CFCl2 | |
3-67 | Me | n-Pr | 2 | CFCl2 | |
3-68 | Me | i-Pr | 2 | CFCl2 | |
3-69 | Me | n-Bu | 2 | CFCl2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-70 | Me | i-Bu | 2 | CFCl2 | |
3-71 | Me | s-Bu | 2 | CFCl2 | |
3-72 | Me | t-Bu | 2 | CFCl2 | |
3-73 | Et | Me | 0 | CFCl2 | |
3-74 | Et | Et | 0 | CFCl2 | |
3-75 | Et | n-Pr | 0 | CFCl2 | |
3-76 | Et | i-Pr | 0 | CFCl2 | |
3-77 | Et | n-Bu | 0 | CFCl2 | |
3-78 | Et | i-Bu | 0 | CFCl2 | |
3-79 | Et | s-Bu | 0 | CFCl2 | |
3-80 | Et | t-Bu | 0 | CFCl2 | |
3-81 | Et | Me | 1 | CFCl2 | |
3-82 | Et | Et | 1 | CFCl2 | |
3-83 | Et | n-Pr | 1 | CFCl2 | |
3-84 | Et | i-Pr | 1 | CFCl2 | |
3-85 | Et | n-Bu | 1 | CFCl2 | |
3-86 | Et | i-Bu | 1 | CFCl2 | |
3-87 | Et | s-Bu | 1 | CFCl2 | |
3-88 | Et | t-Bu | 1 | CFCl2 | |
3-89 | Et | Me | 2 | CFCl2 | |
3-90 | Et | Et | 2 | CFCl2 | |
3-91 | Et | n-Pr | 2 | CFCl2 | |
3-92 | Et | i-Pr | 2 | CFCl2 | |
3-93 | Et | n-Bu | 2 | CFCl2 | |
3-94 | Et | i-Bu | 2 | CFCl2 | |
3-95 | Et | s-Bu | 2 | CFCl2 | |
3-96 | Et | t-Bu | 2 | CFCl2 | |
3-97 | Me | Me | 0 | CCl3 | |
3-98 | Me | Et | 0 | CCl3 | |
3-99 | Me | n-Pr | 0 | CCl3 | |
3-100 | Me | i-Pr | 0 | CCl3 | |
3-101 | Me | n-Bu | 0 | CCl3 | |
3-102 | Me | i-Bu | 0 | CCl3 | |
3-103 | Me | s-Bu | 0 | CCl3 | |
3-104 | Me | t-Bu | 0 | CCl3 | |
3-105 | Me | Me | 1 | CCl3 | |
3-106 | Me | Et | 1 | CCl3 | |
3-107 | Me | n-Pr | 1 | CCl3 | |
3-108 | Me | i-Pr | 1 | CCl3 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-109 | Me | n-Bu | 1 | CCl3 | |
3-110 | Me | i-Bu | 1 | CCl3 | |
3-111 | Me | s-Bu | 1 | CCl3 | |
3-112 | Me | t-Bu | 1 | CCl3 | |
3-113 | Me | Me | 2 | CCl3 | |
3-114 | Me | Et | 2 | CCl3 | |
3-115 | Me | n-Pr | 2 | CCl3 | |
3-116 | Me | i-Pr | 2 | CCl3 | |
3-117 | Me | n-Bu | 2 | CCl3 | |
3-118 | Me | i-Bu | 2 | CCl3 | |
3-119 | Me | s-Bu | 2 | CCl3 | |
3-120 | Me | t-Bu | 2 | CCl3 | |
3-121 | Et | Me | 0 | CCl3 | |
3-122 | Et | Et | 0 | CCl3 | |
3-123 | Et | n-Pr | 0 | CCl3 | |
3-124 | Et | i-Pr | 0 | CCl3 | |
3-125 | Et | n-Bu | 0 | CCl3 | |
3-126 | Et | i-Bu | 0 | CCl3 | |
3-127 | Et | s-Bu | 0 | CCl3 | |
3-128 | Et | t-Bu | 0 | CCl3 | |
3-129 | Et | Me | 1 | CCl3 | |
3-130 | Et | Et | 1 | CCl3 | |
3-131 | Et | n-Pr | 1 | CCl3 | |
3-132 | Et | i-Pr | 1 | CCl3 | |
3-133 | Et | n-Bu | 1 | CCl3 | |
3-134 | Et | i-Bu | 1 | CCl3 | |
3-135 | Et | s-Bu | 1 | CCl3 | |
3-136 | Et | t-Bu | 1 | CCl3 | |
3-137 | Et | Me | 2 | CCl3 | |
3-138 | Et | Et | 2 | CCl3 | |
3-139 | Et | n-Pr | 2 | CCl3 | |
3-140 | Et | i-Pr | 2 | CCl3 | |
3-141 | Et | n-Bu | 2 | CCl3 | |
3-142 | Et | i-Bu | 2 | CCl3 | |
3-143 | Et | s-Bu | 2 | CCl3 | |
3-144 | Et | t-Bu | 2 | CCl3 | |
3-145 | Me | Me | 0 | C2F5 | |
3-146 | Me | Et | 0 | C2F5 | |
3-147 | Me | n-Pr | 0 | C2F5 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-148 | Me | i-Pr | 0 | C2F5 | |
3-149 | Me | n-Bu | 0 | C2F5 | |
3-150 | Me | i-Bu | 0 | C2F5 | |
3-151 | Me | s-Bu | 0 | C2F5 | |
3-152 | Me | t-Bu | 0 | C2F5 | |
3-153 | Me | Me | 1 | C2F5 | |
3-154 | Me | Et | 1 | C2F5 | |
3-155 | Me | n-Pr | 1 | C2F5 | |
3-156 | Me | i-Pr | 1 | C2F5 | |
3-157 | Me | n-Bu | 1 | C2F5 | |
3-158 | Me | i-Bu | 1 | C2F5 | |
3-159 | Me | s-Bu | 1 | C2F5 | |
3-160 | Me | t-Bu | 1 | C2F5 | |
3-161 | Me | Me | 2 | C2F5 | |
3-162 | Me | Et | 2 | C2F5 | |
3-163 | Me | n-Pr | 2 | C2F5 | |
3-164 | Me | i-Pr | 2 | C2F5 | |
3-165 | Me | n-Bu | 2 | C2F5 | |
3-166 | Me | i-Bu | 2 | C2F5 | |
3-167 | Me | s-Bu | 2 | C2F5 | |
3-168 | Me | t-Bu | 2 | C2F5 | |
3-169 | Et | Me | 0 | C2F5 | |
3-170 | Et | Et | 0 | C2F5 | |
3-171 | Et | n-Pr | 0 | C2F5 | |
3-172 | Et | i-Pr | 0 | C2F5 | |
3-173 | Et | n-Bu | 0 | C2F5 | |
3-174 | Et | i-Bu | 0 | C2F5 | |
3-175 | Et | s-Bu | 0 | C2F5 | |
3-176 | Et | t-Bu | 0 | C2F5 | |
3-177 | Et | Me | 1 | C2F5 | |
3-178 | Et | Et | 1 | C2F5 | |
3-179 | Et | n-Pr | 1 | C2F5 | |
3-180 | Et | i-Pr | 1 | C2F5 | |
3-181 | Et | n-Bu | 1 | C2F5 | |
3-182 | Et | i-Bu | 1 | C2F5 | |
3-183 | Et | s-Bu | 1 | C2F5 | |
3-184 | Et | t-Bu | 1 | C2F5 | |
3-185 | Et | Me | 2 | C2F5 | |
3-186 | Et | Et | 2 | C2F5 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-187 | Et | n-Pr | 2 | C2F5 | |
3-188 | Et | i-Pr | 2 | C2F5 | |
3-189 | Et | n-Bu | 2 | C2F5 | |
3-190 | Et | i-Bu | 2 | C2F5 | |
3-191 | Et | s-Bu | 2 | C2F5 | |
3-192 | Et | t-Bu | 2 | C2F5 | |
3-193 | Me | Me | 0 | CF(CF3)2 | |
3-194 | Me | Et | 0 | CF(CF3)2 | |
3-195 | Me | n-Pr | 0 | CF(CF3)2 | |
3-196 | Me | i-Pr | 0 | CF(CF3)2 | |
3-197 | Me | n-Bu | 0 | CF(CF3)2 | |
3-198 | Me | i-Bu | 0 | CF(CF3)2 | |
3-199 | Me | s-Bu | 0 | CF(CF3)2 | |
3-200 | Me | t-Bu | 0 | CF(CF3)2 | |
3-201 | Me | Me | 1 | CF(CF3)2 | |
3-202 | Me | Et | 1 | CF(CF3)2 | |
3-203 | Me | n-Pr | 1 | CF(CF3)2 | |
3-204 | Me | i-Pr | 1 | CF(CF3)2 | |
3-205 | Me | n-Bu | 1 | CF(CF3)2 | |
3-206 | Me | i-Bu | 1 | CF(CF3)2 | |
3-207 | Me | s-Bu | 1 | CF(CF3)2 | |
3-208 | Me | t-Bu | 1 | CF(CF3)2 | |
3-209 | Me | Me | 2 | CF(CF3)2 | |
3-210 | Me | Et | 2 | CF(CF3)2 | |
3-211 | Me | n-Pr | 2 | CF(CF3)2 | |
3-212 | Me | i-Pr | 2 | CF(CF3)2 | |
3-213 | Me | n-Bu | 2 | CF(CF3)2 | |
3-214 | Me | i-Bu | 2 | CF(CF3)2 | |
3-215 | Me | s-Bu | 2 | CF(CF3)2 | |
3-216 | Me | t-Bu | 2 | CF(CF3)2 | |
3-217 | Et | Me | 0 | CF(CF3)2 | |
3-218 | Et | Et | 0 | CF(CF3)2 | |
3-219 | Et | n-Pr | 0 | CF(CF3)2 | |
3-220 | Et | i-Pr | 0 | CF(CF3)2 | |
3-221 | Et | n-Bu | 0 | CF(CF3)2 | |
3-222 | Et | i-Bu | 0 | CF(CF3)2 | |
3-223 | Et | s-Bu | 0 | CF(CF3)2 | |
3-224 | Et | t-Bu | 0 | CF(CF3)2 | |
3-225 | Et | Me | 1 | CF(CF3)2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-226 | Et | Et | 1 | CF(CF3)2 | |
3-227 | Et | n-Pr | 1 | CF(CF3)2 | |
3-228 | Et | i-Pr | 1 | CF(CF3)2 | |
3-229 | Et | n-Bu | 1 | CF(CF3)2 | |
3-230 | Et | i-Bu | 1 | CF(CF3)2 | |
3-231 | Et | s-Bu | 1 | CF(CF3)2 | |
3-232 | Et | t-Bu | 1 | CF(CF3)2 | |
3-233 | Et | Me | 2 | CF(CF3)2 | |
3-234 | Et | Et | 2 | CF(CF3)2 | |
3-235 | Et | n-Pr | 2 | CF(CF3)2 | |
3-236 | Et | i-Pr | 2 | CF(CF3)2 | |
3-237 | Et | n-Bu | 2 | CF(CF3)2 | |
3-238 | Et | i-Bu | 2 | CF(CF3)2 | |
3-239 | Et | s-Bu | 2 | CF(CF3)2 | |
3-240 | Et | t-Bu | 2 | CF(CF3)2 | |
3-241 | Me | Me | 0 | CHF2 | |
3-242 | Me | Et | 0 | CHF2 | |
3-243 | Me | n-Pr | 0 | CHF2 | |
3-244 | Me | i-Pr | 0 | CHF2 | |
3-245 | Me | n-Bu | 0 | CHF2 | |
3-246 | Me | i-Bu | 0 | CHF2 | |
3-247 | Me | s-Bu | 0 | CHF2 | |
3-248 | Me | t-Bu | 0 | CHF2 | |
3-249 | Me | Me | 1 | CHF2 | |
3-250 | Me | Et | 1 | CHF2 | |
3-251 | Me | n-Pr | 1 | CHF2 | |
3-252 | Me | i-Pr | 1 | CHF2 | |
3-253 | Me | n-Bu | 1 | CHF2 | |
3-254 | Me | i-Bu | 1 | CHF2 | |
3-255 | Me | s-Bu | 1 | CHF2 | |
3-256 | Me | t-Bu | 1 | CHF2 | |
3-257 | Me | Me | 2 | CHF2 | |
3-258 | Me | Et | 2 | CHF2 | |
3-259 | Me | n-Pr | 2 | CHF2 | |
3-260 | Me | i-Pr | 2 | CHF2 | |
3-261 | Me | n-Bu | 2 | CHF2 | |
3-262 | Me | i-Bu | 2 | CHF2 | |
3-263 | Me | s-Bu | 2 | CHF2 | |
3-264 | Me | t-Bu | 2 | CHF2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
3-265 | Et | Me | 0 | CHF2 | |
3-266 | Et | Et | 0 | CHF2 | |
3-267 | Et | n-Pr | 0 | CHF2 | |
3-268 | Et | i-Pr | 0 | CHF2 | |
3-269 | Et | n-Bu | 0 | CHF2 | |
3-270 | Et | i-Bu | 0 | CHF2 | |
3-271 | Et | s-Bu | 0 | CHF2 | |
3-272 | Et | t-Bu | 0 | CHF2 | |
3-273 | Et | Me | 1 | CHF2 | |
3-274 | Et | Et | 1 | CHF2 | |
3-275 | Et | n-Pr | 1 | CHF2 | |
3-276 | Et | i-Pr | 1 | CHF2 | |
3-277 | Et | n-Bu | 1 | CHF2 | |
3-278 | Et | i-Bu | 1 | CHF2 | |
3-279 | Et | s-Bu | 1 | CHF2 | |
3-280 | Et | t-Bu | 1 | CHF2 | |
3-281 | Et | Me | 2 | CHF2 | |
3-282 | Et | Et | 2 | CHF2 | |
3-283 | Et | n-Pr | 2 | CHF2 | |
3-284 | Et | i-Pr | 2 | CHF2 | |
3-285 | Et | n-Bu | 2 | CHF2 | |
3-286 | Et | i-Bu | 2 | CHF2 | |
3-287 | Et | s-Bu | 2 | CHF2 | |
3-288 | Et | t-Bu | 2 | CHF2 |
表4:本发明的式(I)的化合物,其中R2为苯硫基,A为氧,Z为(CH2)2,R3为甲基,且R4为氢
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-1 | Me | Me | 0 | CF2Cl |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-2 | Me | Et | 0 | CF2Cl | |
4-3 | Me | n-Pr | 0 | CF2Cl | |
4-4 | Me | i-Pr | 0 | CF2Cl | |
4-5 | Me | n-Bu | 0 | CF2Cl | |
4-6 | Me | i-Bu | 0 | CF2Cl | |
4-7 | Me | s-Bu | 0 | CF2Cl | |
4-8 | Me | t-Bu | 0 | CF2Cl | |
4-9 | Me | Me | 1 | CF2Cl | |
4-10 | Me | Et | 1 | CF2Cl | |
4-11 | Me | n-Pr | 1 | CF2Cl | |
4-12 | Me | i-Pr | 1 | CF2Cl | |
4-13 | Me | n-Bu | 1 | CF2Cl | |
4-14 | Me | i-Bu | 1 | CF2Cl | |
4-15 | Me | s-Bu | 1 | CF2Cl | |
4-16 | Me | t-Bu | 1 | CF2Cl | |
4-17 | Me | Me | 2 | CF2Cl | |
4-18 | Me | Et | 2 | CF2Cl | |
4-19 | Me | n-Pr | 2 | CF2Cl | |
4-20 | Me | i-Pr | 2 | CF2Cl | |
4-21 | Me | n-Bu | 2 | CF2Cl | |
4-22 | Me | i-Bu | 2 | CF2Cl | |
4-23 | Me | s-Bu | 2 | CF2Cl | |
4-24 | Me | t-Bu | 2 | CF2Cl | |
4-25 | Et | Me | 0 | CF2Cl | |
4-26 | Et | Et | 0 | CF2Cl | |
4-27 | Et | n-Pr | 0 | CF2Cl | |
4-28 | Et | i-Pr | 0 | CF2Cl | |
4-29 | Et | n-Bu | 0 | CF2Cl | |
4-30 | Et | i-Bu | 0 | CF2Cl | |
4-31 | Et | s-Bu | 0 | CF2Cl | |
4-32 | Et | t-Bu | 0 | CF2Cl | |
4-33 | Et | Me | 1 | CF2Cl | |
4-34 | Et | Et | 1 | CF2Cl | |
4-35 | Et | n-Pr | 1 | CF2Cl | |
4-36 | Et | i-Pr | 1 | CF2Cl | |
4-37 | Et | n-Bu | 1 | CF2Cl | |
4-38 | Et | i-Bu | 1 | CF2Cl | |
4-39 | Et | s-Bu | 1 | CF2Cl | |
4-40 | Et | t-Bu | 1 | CF2Cl |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-41 | Et | Me | 2 | CF2Cl | |
4-42 | Et | Et | 2 | CF2Cl | |
4-43 | Et | n-Pr | 2 | CF2Cl | |
4-44 | Et | i-Pr | 2 | CF2Cl | |
4-45 | Et | n-Bu | 2 | CF2Cl | |
4-46 | Et | i-Bu | 2 | CF2Cl | |
4-47 | Et | s-Bu | 2 | CF2Cl | |
4-48 | Et | t-Bu | 2 | CF2Cl | |
4-49 | Me | Me | 0 | CFCl2 | |
4-50 | Me | Et | 0 | CFCl2 | |
4-51 | Me | n-Pr | 0 | CFCl2 | |
4-52 | Me | i-Pr | 0 | CFCl2 | |
4-53 | Me | n-Bu | 0 | CFCl2 | |
4-54 | Me | i-Bu | 0 | CFCl2 | |
4-55 | Me | s-Bu | 0 | CFCl2 | |
4-56 | Me | t-Bu | 0 | CFCl2 | |
4-57 | Me | Me | 1 | CFCl2 | |
4-58 | Me | Et | 1 | CFCl2 | |
4-59 | Me | n-Pr | 1 | CFCl2 | |
4-60 | Me | i-Pr | 1 | CFCl2 | |
4-61 | Me | n-Bu | 1 | CFCl2 | |
4-62 | Me | i-Bu | 1 | CFCl2 | |
4-63 | Me | s-Bu | 1 | CFCl2 | |
4-64 | Me | t-Bu | 1 | CFCl2 | |
4-65 | Me | Me | 2 | CFCl2 | |
4-66 | Me | Et | 2 | CFCl2 | |
4-67 | Me | n-Pr | 2 | CFCl2 | |
4-68 | Me | i-Pr | 2 | CFCl2 | |
4-69 | Me | n-Bu | 2 | CFCl2 | |
4-70 | Me | i-Bu | 2 | CFCl2 | |
4-71 | Me | s-Bu | 2 | CFCl2 | |
4-72 | Me | t-Bu | 2 | CFCl2 | |
4-73 | Et | Me | 0 | CFCl2 | |
4-74 | Et | Et | 0 | CFCl2 | |
4-75 | Et | n-Pr | 0 | CFCl2 | |
4-76 | Et | i-Pr | 0 | CFCl2 | |
4-77 | Et | n-Bu | 0 | CFCl2 | |
4-78 | Et | i-Bu | 0 | CFCl2 | |
4-79 | Et | s-Bu | 0 | CFCl2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-80 | Et | t-Bu | 0 | CFCl2 | |
4-81 | Et | Me | 1 | CFCl2 | |
4-82 | Et | Et | 1 | CFCl2 | |
4-83 | Et | n-Pr | 1 | CFCl2 | |
4-84 | Et | i-Pr | 1 | CFCl2 | |
4-85 | Et | n-Bu | 1 | CFCl2 | |
4-86 | Et | i-Bu | 1 | CFCl2 | |
4-87 | Et | s-Bu | 1 | CFCl2 | |
4-88 | Et | t-Bu | 1 | CFCl2 | |
4-89 | Et | Me | 2 | CFCl2 | |
4-90 | Et | Et | 2 | CFCl2 | |
4-91 | Et | n-Pr | 2 | CFCl2 | |
4-92 | Et | i-Pr | 2 | CFCl2 | |
4-93 | Et | n-Bu | 2 | CFCl2 | |
4-94 | Et | i-Bu | 2 | CFCl2 | |
4-95 | Et | s-Bu | 2 | CFCl2 | |
4-96 | Et | t-Bu | 2 | CFCl2 | |
4-97 | Me | Me | 0 | CCl3 | |
4-98 | Me | Et | 0 | CCl3 | |
4-99 | Me | n-Pr | 0 | CCl3 | |
4-100 | Me | i-Pr | 0 | CCl3 | |
4-101 | Me | n-Bu | 0 | CCl3 | |
4-102 | Me | i-Bu | 0 | CCl3 | |
4-103 | Me | s-Bu | 0 | CCl3 | |
4-104 | Me | t-Bu | 0 | CCl3 | |
4-105 | Me | Me | 1 | CCl3 | |
4-106 | Me | Et | 1 | CCl3 | |
4-107 | Me | n-Pr | 1 | CCl3 | |
4-108 | Me | i-Pr | 1 | CCl3 | |
4-109 | Me | n-Bu | 1 | CCl3 | |
4-110 | Me | i-Bu | 1 | CCl3 | |
4-111 | Me | s-Bu | 1 | CCl3 | |
4-112 | Me | t-Bu | 1 | CCl3 | |
4-113 | Me | Me | 2 | CCl3 | |
4-114 | Me | Et | 2 | CCl3 | |
4-115 | Me | n-Pr | 2 | CCl3 | |
4-116 | Me | i-Pr | 2 | CCl3 | |
4-117 | Me | n-Bu | 2 | CCl3 | |
4-118 | Me | i-Bu | 2 | CCl3 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-119 | Me | s-Bu | 2 | CCl3 | |
4-120 | Me | t-Bu | 2 | CCl3 | |
4-121 | Et | Me | 0 | CCl3 | |
4-122 | Et | Et | 0 | CCl3 | |
4-123 | Et | n-Pr | 0 | CCl3 | |
4-124 | Et | i-Pr | 0 | CCl3 | |
4-125 | Et | n-Bu | 0 | CCl3 | |
4-126 | Et | i-Bu | 0 | CCl3 | |
4-127 | Et | s-Bu | 0 | CCl3 | |
4-128 | Et | t-Bu | 0 | CCl3 | |
4-129 | Et | Me | 1 | CCl3 | |
4-130 | Et | Et | 1 | CCl3 | |
4-131 | Et | n-Pr | 1 | CCl3 | |
4-132 | Et | i-Pr | 1 | CCl3 | |
4-133 | Et | n-Bu | 1 | CCl3 | |
4-134 | Et | i-Bu | 1 | CCl3 | |
4-135 | Et | s-Bu | 1 | CCl3 | |
4-136 | Et | t-Bu | 1 | CCl3 | |
4-137 | Et | Me | 2 | CCl3 | |
4-138 | Et | Et | 2 | CCl3 | |
4-139 | Et | n-Pr | 2 | CCl3 | |
4-140 | Et | i-Pr | 2 | CCl3 | |
4-141 | Et | n-Bu | 2 | CCl3 | |
4-142 | Et | i-Bu | 2 | CCl3 | |
4-143 | Et | s-Bu | 2 | CCl3 | |
4-144 | Et | t-Bu | 2 | CCl3 | |
4-145 | Me | Me | 0 | C2F5 | |
4-146 | Me | Et | 0 | C2F5 | |
4-147 | Me | n-Pr | 0 | C2F5 | |
4-148 | Me | i-Pr | 0 | C2F5 | |
4-149 | Me | n-Bu | 0 | C2F5 | |
4-150 | Me | i-Bu | 0 | C2F5 | |
4-151 | Me | s-Bu | 0 | C2F5 | |
4-152 | Me | t-Bu | 0 | C2F5 | |
4-153 | Me | Me | 1 | C2F5 | |
4-154 | Me | Et | 1 | C2F5 | |
4-155 | Me | n-Pr | 1 | C2F5 | |
4-156 | Me | i-Pr | 1 | C2F5 | |
4-157 | Me | n-Bu | 1 | C2F5 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-158 | Me | i-Bu | 1 | C2F5 | |
4-159 | Me | s-Bu | 1 | C2F5 | |
4-160 | Me | t-Bu | 1 | C2F5 | |
4-161 | Me | Me | 2 | C2F5 | |
4-162 | Me | Et | 2 | C2F5 | |
4-163 | Me | n-Pr | 2 | C2F5 | |
4-164 | Me | i-Pr | 2 | C2F5 | |
4-165 | Me | n-Bu | 2 | C2F5 | |
4-166 | Me | i-Bu | 2 | C2F5 | |
4-167 | Me | s-Bu | 2 | C2F5 | |
4-168 | Me | t-Bu | 2 | C2F5 | |
4-169 | Et | Me | 0 | C2F5 | |
4-170 | Et | Et | 0 | C2F5 | |
4-171 | Et | n-Pr | 0 | C2F5 | |
4-172 | Et | i-Pr | 0 | C2F5 | |
4-173 | Et | n-Bu | 0 | C2F5 | |
4-174 | Et | i-Bu | 0 | C2F5 | |
4-175 | Et | s-Bu | 0 | C2F5 | |
4-176 | Et | t-Bu | 0 | C2F5 | |
4-177 | Et | Me | 1 | C2F5 | |
4-178 | Et | Et | 1 | C2F5 | |
4-179 | Et | n-Pr | 1 | C2F5 | |
4-180 | Et | i-Pr | 1 | C2F5 | |
4-181 | Et | n-Bu | 1 | C2F5 | |
4-182 | Et | i-Bu | 1 | C2F5 | |
4-183 | Et | s-Bu | 1 | C2F5 | |
4-184 | Et | t-Bu | 1 | C2F5 | |
4-185 | Et | Me | 2 | C2F5 | |
4-186 | Et | Et | 2 | C2F5 | |
4-187 | Et | n-Pr | 2 | C2F5 | |
4-188 | Et | i-Pr | 2 | C2F5 | |
4-189 | Et | n-Bu | 2 | C2F5 | |
4-190 | Et | i-Bu | 2 | C2F5 | |
4-191 | Et | s-Bu | 2 | C2F5 | |
4-192 | Et | t-Bu | 2 | C2F5 | |
4-193 | Me | Me | 0 | CF(CF3)2 | |
4-194 | Me | Et | 0 | CF(CF3)2 | |
4-195 | Me | n-Pr | 0 | CF(CF3)2 | |
4-196 | Me | i-Pr | 0 | CF(CF3)2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-197 | Me | n-Bu | 0 | CF(CF3)2 | |
4-198 | Me | i-Bu | 0 | CF(CF3)2 | |
4-199 | Me | s-Bu | 0 | CF(CF3)2 | |
4-200 | Me | t-Bu | 0 | CF(CF3)2 | |
4-201 | Me | Me | 1 | CF(CF3)2 | |
4-202 | Me | Et | 1 | CF(CF3)2 | |
4-203 | Me | n-Pr | 1 | CF(CF3)2 | |
4-204 | Me | i-Pr | 1 | CF(CF3)2 | |
4-205 | Me | n-Bu | 1 | CF(CF3)2 | |
4-206 | Me | i-Bu | 1 | CF(CF3)2 | |
4-207 | Me | s-Bu | 1 | CF(CF3)2 | |
4-208 | Me | t-Bu | 1 | CF(CF3)2 | |
4-209 | Me | Me | 2 | CF(CF3)2 | |
4-210 | Me | Et | 2 | CF(CF3)2 | |
4-211 | Me | n-Pr | 2 | CF(CF3)2 | |
4-212 | Me | i-Pr | 2 | CF(CF3)2 | |
4-213 | Me | n-Bu | 2 | CF(CF3)2 | |
4-214 | Me | i-Bu | 2 | CF(CF3)2 | |
4-215 | Me | s-Bu | 2 | CF(CF3)2 | |
4-216 | Me | t-Bu | 2 | CF(CF3)2 | |
4-217 | Et | Me | 0 | CF(CF3)2 | |
4-218 | Et | Et | 0 | CF(CF3)2 | |
4-219 | Et | n-Pr | 0 | CF(CF3)2 | |
4-220 | Et | i-Pr | 0 | CF(CF3)2 | |
4-221 | Et | n-Bu | 0 | CF(CF3)2 | |
4-222 | Et | i-Bu | 0 | CF(CF3)2 | |
4-223 | Et | s-Bu | 0 | CF(CF3)2 | |
4-224 | Et | t-Bu | 0 | CF(CF3)2 | |
4-225 | Et | Me | 1 | CF(CF3)2 | |
4-226 | Et | Et | 1 | CF(CF3)2 | |
4-227 | Et | n-Pr | 1 | CF(CF3)2 | |
4-228 | Et | i-Pr | 1 | CF(CF3)2 | |
4-229 | Et | n-Bu | 1 | CF(CF3)2 | |
4-230 | Et | i-Bu | 1 | CF(CF3)2 | |
4-231 | Et | s-Bu | 1 | CF(CF3)2 | |
4-232 | Et | t-Bu | 1 | CF(CF3)2 | |
4-233 | Et | Me | 2 | CF(CF3)2 | |
4-234 | Et | Et | 2 | CF(CF3)2 | |
4-235 | Et | n-Pr | 2 | CF(CF3)2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-236 | Et | i-Pr | 2 | CF(CF3)2 | |
4-237 | Et | n-Bu | 2 | CF(CF3)2 | |
4-238 | Et | i-Bu | 2 | CF(CF3)2 | |
4-239 | Et | s-Bu | 2 | CF(CF3)2 | |
4-240 | Et | t-Bu | 2 | CF(CF3)2 | |
4-241 | Me | Me | 0 | CHF2 | |
4-242 | Me | Et | 0 | CHF2 | |
4-243 | Me | n-Pr | 0 | CHF2 | |
4-244 | Me | i-Pr | 0 | CHF2 | |
4-245 | Me | n-Bu | 0 | CHF2 | |
4-246 | Me | i-Bu | 0 | CHF2 | |
4-247 | Me | s-Bu | 0 | CHF2 | |
4-248 | Me | t-Bu | 0 | CHF2 | |
4-249 | Me | Me | 1 | CHF2 | |
4-250 | Me | Et | 1 | CHF2 | |
4-251 | Me | n-Pr | 1 | CHF2 | |
4-252 | Me | i-Pr | 1 | CHF2 | |
4-253 | Me | n-Bu | 1 | CHF2 | |
4-254 | Me | i-Bu | 1 | CHF2 | |
4-255 | Me | s-Bu | 1 | CHF2 | |
4-256 | Me | t-Bu | 1 | CHF2 | |
4-257 | Me | Me | 2 | CHF2 | |
4-258 | Me | Et | 2 | CHF2 | |
4-259 | Me | n-Pr | 2 | CHF2 | |
4-260 | Me | i-Pr | 2 | CHF2 | |
4-261 | Me | n-Bu | 2 | CHF2 | |
4-262 | Me | i-Bu | 2 | CHF2 | |
4-263 | Me | s-Bu | 2 | CHF2 | |
4-264 | Me | t-Bu | 2 | CHF2 | |
4-265 | Et | Me | 0 | CHF2 | |
4-266 | Et | Et | 0 | CHF2 | |
4-267 | Et | n-Pr | 0 | CHF2 | |
4-268 | Et | i-Pr | 0 | CHF2 | |
4-269 | Et | n-Bu | 0 | CHF2 | |
4-270 | Et | i-Bu | 0 | CHF2 | |
4-271 | Et | s-Bu | 0 | CHF2 | |
4-272 | Et | t-Bu | 0 | CHF2 | |
4-273 | Et | Me | 1 | CHF2 | |
4-274 | Et | Et | 1 | CHF2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
4-275 | Et | n-Pr | 1 | CHF2 | |
4-276 | Et | i-Pr | 1 | CHF2 | |
4-277 | Et | n-Bu | 1 | CHF2 | |
4-278 | Et | i-Bu | 1 | CHF2 | |
4-279 | Et | s-Bu | 1 | CHF2 | |
4-280 | Et | t-Bu | 1 | CHF2 | |
4-281 | Et | Me | 2 | CHF2 | |
4-282 | Et | Et | 2 | CHF2 | |
4-283 | Et | n-Pr | 2 | CHF2 | |
4-284 | Et | i-Pr | 2 | CHF2 | |
4-285 | Et | n-Bu | 2 | CHF2 | |
4-286 | Et | i-Bu | 2 | CHF2 | |
4-287 | Et | s-Bu | 2 | CHF2 | |
4-288 | Et | t-Bu | 2 | CHF2 |
表5:本发明的式(I)的化合物,其中R2为苯硫基,A为氧,Z为(CH2)2,R3为氢,且R4为甲基
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-1 | Me | Me | 0 | CF2Cl | |
5-2 | Me | Et | 0 | CF2Cl | |
5-3 | Me | n-Pr | 0 | CF2Cl | |
5-4 | Me | i-Pr | 0 | CF2Cl | |
5-5 | Me | n-Bu | 0 | CF2Cl | |
5-6 | Me | i-Bu | 0 | CF2Cl | |
5-7 | Me | s-Bu | 0 | CF2Cl | |
5-8 | Me | t-Bu | 0 | CF2Cl | |
5-9 | Me | Me | 1 | CF2Cl | |
5-10 | Me | Et | 1 | CF2Cl | |
5-11 | Me | n-Pr | 1 | CF2Cl | |
5-12 | Me | i-Pr | 1 | CF2Cl | |
5-13 | Me | n-Bu | 1 | CF2Cl |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-14 | Me | i-Bu | 1 | CF2Cl | |
5-15 | Me | s-Bu | 1 | CF2Cl | |
5-16 | Me | t-Bu | 1 | CF2Cl | |
5-17 | Me | Me | 2 | CF2Cl | |
5-18 | Me | Et | 2 | CF2Cl | |
5-19 | Me | n-Pr | 2 | CF2Cl | |
5-20 | Me | i-Pr | 2 | CF2Cl | |
5-21 | Me | n-Bu | 2 | CF2Cl | |
5-22 | Me | i-Bu | 2 | CF2Cl | |
5-23 | Me | s-Bu | 2 | CF2Cl | |
5-24 | Me | t-Bu | 2 | CF2Cl | |
5-25 | Et | Me | 0 | CF2Cl | |
5-26 | Et | Et | 0 | CF2Cl | |
5-27 | Et | n-Pr | 0 | CF2Cl | |
5-28 | Et | i-Pr | 0 | CF2Cl | |
5-29 | Et | n-Bu | 0 | CF2Cl | |
5-30 | Et | i-Bu | 0 | CF2Cl | |
5-31 | Et | s-Bu | 0 | CF2Cl | |
5-32 | Et | t-Bu | 0 | CF2Cl | |
5-33 | Et | Me | 1 | CF2Cl | |
5-34 | Et | Et | 1 | CF2Cl | |
5-35 | Et | n-Pr | 1 | CF2Cl | |
5-36 | Et | i-Pr | 1 | CF2Cl | |
5-37 | Et | n-Bu | 1 | CF2Cl | |
5-38 | Et | i-Bu | 1 | CF2Cl | |
5-39 | Et | s-Bu | 1 | CF2Cl | |
5-40 | Et | t-Bu | 1 | CF2Cl | |
5-41 | Et | Me | 2 | CF2Cl | |
5-42 | Et | Et | 2 | CF2Cl | |
5-43 | Et | n-Pr | 2 | CF2Cl | |
5-44 | Et | i-Pr | 2 | CF2Cl | |
5-45 | Et | n-Bu | 2 | CF2Cl | |
5-46 | Et | i-Bu | 2 | CF2Cl | |
5-47 | Et | s-Bu | 2 | CF2Cl | |
5-48 | Et | t-Bu | 2 | CF2Cl | |
5-49 | Me | Me | 0 | CFCl2 | |
5-50 | Me | Et | 0 | CFCl2 | |
5-51 | Me | n-Pr | 0 | CFCl2 | |
5-52 | Me | i-Pr | 0 | CFCl2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-53 | Me | n-Bu | 0 | CFCl2 | |
5-54 | Me | i-Bu | 0 | CFCl2 | |
5-55 | Me | s-Bu | 0 | CFCl2 | |
5-56 | Me | t-Bu | 0 | CFCl2 | |
5-57 | Me | Me | 1 | CFCl2 | |
5-58 | Me | Et | 1 | CFCl2 | |
5-59 | Me | n-Pr | 1 | CFCl2 | |
5-60 | Me | i-Pr | 1 | CFCl2 | |
5-61 | Me | n-Bu | 1 | CFCl2 | |
5-62 | Me | i-Bu | 1 | CFCl2 | |
5-63 | Me | s-Bu | 1 | CFCl2 | |
5-64 | Me | t-Bu | 1 | CFCl2 | |
5-65 | Me | Me | 2 | CFCl2 | |
5-66 | Me | Et | 2 | CFCl2 | |
5-67 | Me | n-Pr | 2 | CFCl2 | |
5-68 | Me | i-Pr | 2 | CFCl2 | |
5-69 | Me | n-Bu | 2 | CFCl2 | |
5-70 | Me | i-Bu | 2 | CFCl2 | |
5-71 | Me | s-Bu | 2 | CFCl2 | |
5-72 | Me | t-Bu | 2 | CFCl2 | |
5-73 | Et | Me | 0 | CFCl2 | |
5-74 | Et | Et | 0 | CFCl2 | |
5-75 | Et | n-Pr | 0 | CFCl2 | |
5-76 | Et | i-Pr | 0 | CFCl2 | |
5-77 | Et | n-Bu | 0 | CFCl2 | |
5-78 | Et | i-Bu | 0 | CFCl2 | |
5-79 | Et | s-Bu | 0 | CFCl2 | |
5-80 | Et | t-Bu | 0 | CFCl2 | |
5-81 | Et | Me | 1 | CFCl2 | |
5-82 | Et | Et | 1 | CFCl2 | |
5-83 | Et | n-Pr | 1 | CFCl2 | |
5-84 | Et | i-Pr | 1 | CFCl2 | |
5-85 | Et | n-Bu | 1 | CFCl2 | |
5-86 | Et | i-Bu | 1 | CFCl2 | |
5-87 | Et | s-Bu | 1 | CFCl2 | |
5-88 | Et | t-Bu | 1 | CFCl2 | |
5-89 | Et | Me | 2 | CFCl2 | |
5-90 | Et | Et | 2 | CFCl2 | |
5-91 | Et | n-Pr | 2 | CFCl2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-92 | Et | i-Pr | 2 | CFCl2 | |
5-93 | Et | n-Bu | 2 | CFCl2 | |
5-94 | Et | i-Bu | 2 | CFCl2 | |
5-95 | Et | s-Bu | 2 | CFCl2 | |
5-96 | Et | t-Bu | 2 | CFCl2 | |
5-97 | Me | Me | 0 | CCl3 | |
5-98 | Me | Et | 0 | CCl3 | |
5-99 | Me | n-Pr | 0 | CCl3 | |
5-100 | Me | i-Pr | 0 | CCl3 | |
5-101 | Me | n-Bu | 0 | CCl3 | |
5-102 | Me | i-Bu | 0 | CCl3 | |
5-103 | Me | s-Bu | 0 | CCl3 | |
5-104 | Me | t-Bu | 0 | CCl3 | |
5-105 | Me | Me | 1 | CCl3 | |
5-106 | Me | Et | 1 | CCl3 | |
5-107 | Me | n-Pr | 1 | CCl3 | |
5-108 | Me | i-Pr | 1 | CCl3 | |
5-109 | Me | n-Bu | 1 | CCl3 | |
5-110 | Me | i-Bu | 1 | CCl3 | |
5-111 | Me | s-Bu | 1 | CCl3 | |
5-112 | Me | t-Bu | 1 | CCl3 | |
5-113 | Me | Me | 2 | CCl3 | |
5-114 | Me | Et | 2 | CCl3 | |
5-115 | Me | n-Pr | 2 | CCl3 | |
5-116 | Me | i-Pr | 2 | CCl3 | |
5-117 | Me | n-Bu | 2 | CCl3 | |
5-118 | Me | i-Bu | 2 | CCl3 | |
5-119 | Me | s-Bu | 2 | CCl3 | |
5-120 | Me | t-Bu | 2 | CCl3 | |
5-121 | Et | Me | 0 | CCl3 | |
5-122 | Et | Et | 0 | CCl3 | |
5-123 | Et | n-Pr | 0 | CCl3 | |
5-124 | Et | i-Pr | 0 | CCl3 | |
5-125 | Et | n-Bu | 0 | CCl3 | |
5-126 | Et | i-Bu | 0 | CCl3 | |
5-127 | Et | s-Bu | 0 | CCl3 | |
5-128 | Et | t-Bu | 0 | CCl3 | |
5-129 | Et | Me | 1 | CCl3 | |
5-130 | Et | Et | 1 | CCl3 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-131 | Et | n-Pr | 1 | CCl3 | |
5-132 | Et | i-Pr | 1 | CCl3 | |
5-133 | Et | n-Bu | 1 | CCl3 | |
5-134 | Et | i-Bu | 1 | CCl3 | |
5-135 | Et | s-Bu | 1 | CCl3 | |
5-136 | Et | t-Bu | 1 | CCl3 | |
5-137 | Et | Me | 2 | CCl3 | |
5-138 | Et | Et | 2 | CCl3 | |
5-139 | Et | n-Pr | 2 | CCl3 | |
5-140 | Et | i-Pr | 2 | CCl3 | |
5-141 | Et | n-Bu | 2 | CCl3 | |
5-142 | Et | i-Bu | 2 | CCl3 | |
5-143 | Et | s-Bu | 2 | CCl3 | |
5-144 | Et | t-Bu | 2 | CCl3 | |
5-145 | Me | Me | 0 | C2F5 | |
5-146 | Me | Et | 0 | C2F5 | |
5-147 | Me | n-Pr | 0 | C2F5 | |
5-148 | Me | i-Pr | 0 | C2F5 | |
5-149 | Me | n-Bu | 0 | C2F5 | |
5-150 | Me | i-Bu | 0 | C2F5 | |
5-151 | Me | s-Bu | 0 | C2F5 | |
5-152 | Me | t-Bu | 0 | C2F5 | |
5-153 | Me | Me | 1 | C2F5 | |
5-154 | Me | Et | 1 | C2F5 | |
5-155 | Me | n-Pr | 1 | C2F5 | |
5-156 | Me | i-Pr | 1 | C2F5 | |
5-157 | Me | n-Bu | 1 | C2F5 | |
5-158 | Me | i-Bu | 1 | C2F5 | |
5-159 | Me | s-Bu | 1 | C2F5 | |
5-160 | Me | t-Bu | 1 | C2F5 | |
5-161 | Me | Me | 2 | C2F5 | |
5-162 | Me | Et | 2 | C2F5 | |
5-163 | Me | n-Pr | 2 | C2F5 | |
5-164 | Me | i-Pr | 2 | C2F5 | |
5-165 | Me | n-Bu | 2 | C2F5 | |
5-166 | Me | i-Bu | 2 | C2F5 | |
5-167 | Me | s-Bu | 2 | C2F5 | |
5-168 | Me | t-Bu | 2 | C2F5 | |
5-169 | Et | Me | 0 | C2F5 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-170 | Et | Et | 0 | C2F5 | |
5-171 | Et | n-Pr | 0 | C2F5 | |
5-172 | Et | i-Pr | 0 | C2F5 | |
5-173 | Et | n-Bu | 0 | C2F5 | |
5-174 | Et | i-Bu | 0 | C2F5 | |
5-175 | Et | s-Bu | 0 | C2F5 | |
5-176 | Et | t-Bu | 0 | C2F5 | |
5-177 | Et | Me | 1 | C2F5 | |
5-178 | Et | Et | 1 | C2F5 | |
5-179 | Et | n-Pr | 1 | C2F5 | |
5-180 | Et | i-Pr | 1 | C2F5 | |
5-181 | Et | n-Bu | 1 | C2F5 | |
5-182 | Et | i-Bu | 1 | C2F5 | |
5-183 | Et | s-Bu | 1 | C2F5 | |
5-184 | Et | t-Bu | 1 | C2F5 | |
5-185 | Et | Me | 2 | C2F5 | |
5-186 | Et | Et | 2 | C2F5 | |
5-187 | Et | n-Pr | 2 | C2F5 | |
5-188 | Et | i-Pr | 2 | C2F5 | |
5-189 | Et | n-Bu | 2 | C2F5 | |
5-190 | Et | i-Bu | 2 | C2F5 | |
5-191 | Et | s-Bu | 2 | C2F5 | |
5-192 | Et | t-Bu | 2 | C2F5 | |
5-193 | Me | Me | 0 | CF(CF3)2 | |
5-194 | Me | Et | 0 | CF(CF3)2 | |
5-195 | Me | n-Pr | 0 | CF(CF3)2 | |
5-196 | Me | i-Pr | 0 | CF(CF3)2 | |
5-197 | Me | n-Bu | 0 | CF(CF3)2 | |
5-198 | Me | i-Bu | 0 | CF(CF3)2 | |
5-199 | Me | s-Bu | 0 | CF(CF3)2 | |
5-200 | Me | t-Bu | 0 | CF(CF3)2 | |
5-201 | Me | Me | 1 | CF(CF3)2 | |
5-202 | Me | Et | 1 | CF(CF3)2 | |
5-203 | Me | n-Pr | 1 | CF(CF3)2 | |
5-204 | Me | i-Pr | 1 | CF(CF3)2 | |
5-205 | Me | n-Bu | 1 | CF(CF3)2 | |
5-206 | Me | i-Bu | 1 | CF(CF3)2 | |
5-207 | Me | s-Bu | 1 | CF(CF3)2 | |
5-208 | Me | t-Bu | 1 | CF(CF3)2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-209 | Me | Me | 2 | CF(CF3)2 | |
5-210 | Me | Et | 2 | CF(CF3)2 | |
5-211 | Me | n-Pr | 2 | CF(CF3)2 | |
5-212 | Me | i-Pr | 2 | CF(CF3)2 | |
5-213 | Me | n-Bu | 2 | CF(CF3)2 | |
5-214 | Me | i-Bu | 2 | CF(CF3)2 | |
5-215 | Me | s-Bu | 2 | CF(CF3)2 | |
5-216 | Me | t-Bu | 2 | CF(CF3)2 | |
5-217 | Et | Me | 0 | CF(CF3)2 | |
5-218 | Et | Et | 0 | CF(CF3)2 | |
5-219 | Et | n-Pr | 0 | CF(CF3)2 | |
5-220 | Et | i-Pr | 0 | CF(CF3)2 | |
5-221 | Et | n-Bu | 0 | CF(CF3)2 | |
5-222 | Et | i-Bu | 0 | CF(CF3)2 | |
5-223 | Et | s-Bu | 0 | CF(CF3)2 | |
5-224 | Et | t-Bu | 0 | CF(CF3)2 | |
5-225 | Et | Me | 1 | CF(CF3)2 | |
5-226 | Et | Et | 1 | CF(CF3)2 | |
5-227 | Et | n-Pr | 1 | CF(CF3)2 | |
5-228 | Et | i-Pr | 1 | CF(CF3)2 | |
5-229 | Et | n-Bu | 1 | CF(CF3)2 | |
5-230 | Et | i-Bu | 1 | CF(CF3)2 | |
5-231 | Et | s-Bu | 1 | CF(CF3)2 | |
5-232 | Et | t-Bu | 1 | CF(CF3)2 | |
5-233 | Et | Me | 2 | CF(CF3)2 | |
5-234 | Et | Et | 2 | CF(CF3)2 | |
5-235 | Et | n-Pr | 2 | CF(CF3)2 | |
5-236 | Et | i-Pr | 2 | CF(CF3)2 | |
5-237 | Et | n-Bu | 2 | CF(CF3)2 | |
5-238 | Et | i-Bu | 2 | CF(CF3)2 | |
5-239 | Et | s-Bu | 2 | CF(CF3)2 | |
5-240 | Et | t-Bu | 2 | CF(CF3)2 | |
5-241 | Me | Me | 0 | CHF2 | |
5-242 | Me | Et | 0 | CHF2 | |
5-243 | Me | n-Pr | 0 | CHF2 | |
5-244 | Me | i-Pr | 0 | CHF2 | |
5-245 | Me | n-Bu | 0 | CHF2 | |
5-246 | Me | i-Bu | 0 | CHF2 | |
5-247 | Me | s-Bu | 0 | CHF2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-248 | Me | t-Bu | 0 | CHF2 | |
5-249 | Me | Me | 1 | CHF2 | |
5-250 | Me | Et | 1 | CHF2 | |
5-251 | Me | n-Pr | 1 | CHF2 | |
5-252 | Me | i-Pr | 1 | CHF2 | |
5-253 | Me | n-Bu | 1 | CHF2 | |
5-254 | Me | i-Bu | 1 | CHF2 | |
5-255 | Me | s-Bu | 1 | CHF2 | |
5-256 | Me | t-Bu | 1 | CHF2 | |
5-257 | Me | Me | 2 | CHF2 | |
5-258 | Me | Et | 2 | CHF2 | |
5-259 | Me | n-Pr | 2 | CHF2 | |
5-260 | Me | i-Pr | 2 | CHF2 | |
5-261 | Me | n-Bu | 2 | CHF2 | |
5-262 | Me | i-Bu | 2 | CHF2 | |
5-263 | Me | s-Bu | 2 | CHF2 | |
5-264 | Me | t-Bu | 2 | CHF2 | |
5-265 | Et | Me | 0 | CHF2 | |
5-266 | Et | Et | 0 | CHF2 | |
5-267 | Et | n-Pr | 0 | CHF2 | |
5-268 | Et | i-Pr | 0 | CHF2 | |
5-269 | Et | n-Bu | 0 | CHF2 | |
5-270 | Et | i-Bu | 0 | CHF2 | |
5-271 | Et | s-Bu | 0 | CHF2 | |
5-272 | Et | t-Bu | 0 | CHF2 | |
5-273 | Et | Me | 1 | CHF2 | |
5-274 | Et | Et | 1 | CHF2 | |
5-275 | Et | n-Pr | 1 | CHF2 | |
5-276 | Et | i-Pr | 1 | CHF2 | |
5-277 | Et | n-Bu | 1 | CHF2 | |
5-278 | Et | i-Bu | 1 | CHF2 | |
5-279 | Et | s-Bu | 1 | CHF2 | |
5-280 | Et | t-Bu | 1 | CHF2 | |
5-281 | Et | Me | 2 | CHF2 | |
5-282 | Et | Et | 2 | CHF2 | |
5-283 | Et | n-Pr | 2 | CHF2 | |
5-284 | Et | i-Pr | 2 | CHF2 | |
5-285 | Et | n-Bu | 2 | CHF2 | |
5-286 | Et | i-Bu | 2 | CHF2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[CDCl3] |
5-287 | Et | s-Bu | 2 | CHF2 | |
5-288 | Et | t-Bu | 2 | CHF2 |
表6:本发明的式(II)的化合物
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-1 | Me | Me | 0 | CF2Cl | |
6-2 | Me | Et | 0 | CF2Cl | |
6-3 | Me | n-Pr | 0 | CF2Cl | |
6-4 | Me | i-Pr | 0 | CF2Cl | |
6-5 | Me | n-Bu | 0 | CF2Cl | |
6-6 | Me | i-Bu | 0 | CF2Cl | |
6-7 | Me | s-Bu | 0 | CF2Cl | |
6-8 | Me | t-Bu | 0 | CF2Cl | |
6-9 | Me | Me | 1 | CF2Cl | |
6-10 | Me | Et | 1 | CF2Cl | |
6-11 | Me | n-Pr | 1 | CF2Cl | |
6-12 | Me | i-Pr | 1 | CF2Cl | |
6-13 | Me | n-Bu | 1 | CF2Cl | |
6-14 | Me | i-Bu | 1 | CF2Cl | |
6-15 | Me | s-Bu | 1 | CF2Cl | |
6-16 | Me | t-Bu | 1 | CF2Cl | |
6-17 | Me | Me | 2 | CF2Cl | |
6-18 | Me | Et | 2 | CF2Cl | |
6-19 | Me | n-Pr | 2 | CF2Cl | |
6-20 | Me | i-Pr | 2 | CF2Cl | |
6-21 | Me | n-Bu | 2 | CF2Cl | |
6-22 | Me | i-Bu | 2 | CF2Cl | |
6-23 | Me | s-Bu | 2 | CF2Cl | |
6-24 | Me | t-Bu | 2 | CF2Cl | |
6-25 | Et | Me | 0 | CF2Cl | |
6-26 | Et | Et | 0 | CF2Cl | |
6-27 | Et | n-Pr | 0 | CF2Cl | |
6-28 | Et | i-Pr | 0 | CF2Cl |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-29 | Et | n-Bu | 0 | CF2Cl | |
6-30 | Et | i-Bu | 0 | CF2Cl | |
6-31 | Et | s-Bu | 0 | CF2Cl | |
6-32 | Et | t-Bu | 0 | CF2Cl | |
6-33 | Et | Me | 1 | CF2Cl | |
6-34 | Et | Et | 1 | CF2Cl | |
6-35 | Et | n-Pr | 1 | CF2Cl | |
6-36 | Et | i-Pr | 1 | CF2Cl | |
6-37 | Et | n-Bu | 1 | CF2Cl | |
6-38 | Et | i-Bu | 1 | CF2Cl | |
6-39 | Et | s-Bu | 1 | CF2Cl | |
6-40 | Et | t-Bu | 1 | CF2Cl | |
6-41 | Et | Me | 2 | CF2Cl | |
6-42 | Et | Et | 2 | CF2Cl | |
6-43 | Et | n-Pr | 2 | CF2Cl | |
6-44 | Et | i-Pr | 2 | CF2Cl | |
6-45 | Et | n-Bu | 2 | CF2Cl | |
6-46 | Et | i-Bu | 2 | CF2Cl | |
6-47 | Et | s-Bu | 2 | CF2Cl | |
6-48 | Et | t-Bu | 2 | CF2Cl | |
6-49 | Me | Me | 0 | CFCl2 | |
6-50 | Me | Et | 0 | CFCl2 | |
6-51 | Me | n-Pr | 0 | CFCl2 | |
6-52 | Me | i-Pr | 0 | CFCl2 | |
6-53 | Me | n-Bu | 0 | CFCl2 | |
6-54 | Me | i-Bu | 0 | CFCl2 | |
6-55 | Me | s-Bu | 0 | CFCl2 | |
6-56 | Me | t-Bu | 0 | CFCl2 | |
6-57 | Me | Me | 1 | CFCl2 | |
6-58 | Me | Et | 1 | CFCl2 | |
6-59 | Me | n-Pr | 1 | CFCl2 | |
6-60 | Me | i-Pr | 1 | CFCl2 | |
6-61 | Me | n-Bu | 1 | CFCl2 | |
6-62 | Me | i-Bu | 1 | CFCl2 | |
6-63 | Me | s-Bu | 1 | CFCl2 | |
6-64 | Me | t-Bu | 1 | CFCl2 | |
6-65 | Me | Me | 2 | CFCl2 | |
6-66 | Me | Et | 2 | CFCl2 | |
6-67 | Me | n-Pr | 2 | CFCl2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-68 | Me | i-Pr | 2 | CFCl2 | |
6-69 | Me | n-Bu | 2 | CFCl2 | |
6-70 | Me | i-Bu | 2 | CFCl2 | |
6-71 | Me | s-Bu | 2 | CFCl2 | |
6-72 | Me | t-Bu | 2 | CFCl2 | |
6-73 | Et | Me | 0 | CFCl2 | |
6-74 | Et | Et | 0 | CFCl2 | |
6-75 | Et | n-Pr | 0 | CFCl2 | |
6-76 | Et | i-Pr | 0 | CFCl2 | |
6-77 | Et | n-Bu | 0 | CFCl2 | |
6-78 | Et | i-Bu | 0 | CFCl2 | |
6-79 | Et | s-Bu | 0 | CFCl2 | |
6-80 | Et | t-Bu | 0 | CFCl2 | |
6-81 | Et | Me | 1 | CFCl2 | |
6-82 | Et | Et | 1 | CFCl2 | |
6-83 | Et | n-Pr | 1 | CFCl2 | |
6-84 | Et | i-Pr | 1 | CFCl2 | |
6-85 | Et | n-Bu | 1 | CFCl2 | |
6-86 | Et | i-Bu | 1 | CFCl2 | |
6-87 | Et | s-Bu | 1 | CFCl2 | |
6-88 | Et | t-Bu | 1 | CFCl2 | |
6-89 | Et | Me | 2 | CFCl2 | |
6-90 | Et | Et | 2 | CFCl2 | |
6-91 | Et | n-Pr | 2 | CFCl2 | |
6-92 | Et | i-Pr | 2 | CFCl2 | |
6-93 | Et | n-Bu | 2 | CFCl2 | |
6-94 | Et | i-Bu | 2 | CFCl2 | |
6-95 | Et | s-Bu | 2 | CFCl2 | |
6-96 | Et | t-Bu | 2 | CFCl2 | |
6-97 | Me | Me | 0 | CCl3 | |
6-98 | Me | Et | 0 | CCl3 | |
6-99 | Me | n-Pr | 0 | CCl3 | |
6-100 | Me | i-Pr | 0 | CCl3 | |
6-101 | Me | n-Bu | 0 | CCl3 | |
6-102 | Me | i-Bu | 0 | CCl3 | |
6-103 | Me | s-Bu | 0 | CCl3 | |
6-104 | Me | t-Bu | 0 | CCl3 | |
6-105 | Me | Me | 1 | CCl3 | |
6-106 | Me | Et | 1 | CCl3 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-107 | Me | n-Pr | 1 | CCl3 | |
6-108 | Me | i-Pr | 1 | CCl3 | |
6-109 | Me | n-Bu | 1 | CCl3 | |
6-110 | Me | i-Bu | 1 | CCl3 | |
6-111 | Me | s-Bu | 1 | CCl3 | |
6-112 | Me | t-Bu | 1 | CCl3 | |
6-113 | Me | Me | 2 | CCl3 | |
6-114 | Me | Et | 2 | CCl3 | |
6-115 | Me | n-Pr | 2 | CCl3 | |
6-116 | Me | i-Pr | 2 | CCl3 | |
6-117 | Me | n-Bu | 2 | CCl3 | |
6-118 | Me | i-Bu | 2 | CCl3 | |
6-119 | Me | s-Bu | 2 | CCl3 | |
6-120 | Me | t-Bu | 2 | CCl3 | |
6-121 | Et | Me | 0 | CCl3 | |
6-122 | Et | Et | 0 | CCl3 | |
6-123 | Et | n-Pr | 0 | CCl3 | |
6-124 | Et | i-Pr | 0 | CCl3 | |
6-125 | Et | n-Bu | 0 | CCl3 | |
6-126 | Et | i-Bu | 0 | CCl3 | |
6-127 | Et | s-Bu | 0 | CCl3 | |
6-128 | Et | t-Bu | 0 | CCl3 | |
6-129 | Et | Me | 1 | CCl3 | |
6-130 | Et | Et | 1 | CCl3 | |
6-131 | Et | n-Pr | 1 | CCl3 | |
6-132 | Et | i-Pr | 1 | CCl3 | |
6-133 | Et | n-Bu | 1 | CCl3 | |
6-134 | Et | i-Bu | 1 | CCl3 | |
6-135 | Et | s-Bu | 1 | CCl3 | |
6-136 | Et | t-Bu | 1 | CCl3 | |
6-137 | Et | Me | 2 | CCl3 | |
6-138 | Et | Et | 2 | CCl3 | |
6-139 | Et | n-Pr | 2 | CCl3 | |
6-140 | Et | i-Pr | 2 | CCl3 | |
6-141 | Et | n-Bu | 2 | CCl3 | |
6-142 | Et | i-Bu | 2 | CCl3 | |
6-143 | Et | s-Bu | 2 | CCl3 | |
6-144 | Et | t-Bu | 2 | CCl3 | |
6-145 | Me | Me | 0 | C2F5 | 7.84(d,1H),7.65(d,1H),2.76(s,3H),2.27(s,3H) |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-146 | Me | Et | 0 | C2F5 | |
6-147 | Me | n-Pr | 0 | C2F5 | |
6-148 | Me | i-Pr | 0 | C2F5 | |
6-149 | Me | n-Bu | 0 | C2F5 | |
6-150 | Me | i-Bu | 0 | C2F5 | |
6-151 | Me | s-Bu | 0 | C2F5 | |
6-152 | Me | t-Bu | 0 | C2F5 | |
6-153 | Me | Me | 1 | C2F5 | |
6-154 | Me | Et | 1 | C2F5 | |
6-155 | Me | n-Pr | 1 | C2F5 | |
6-156 | Me | i-Pr | 1 | C2F5 | |
6-157 | Me | n-Bu | 1 | C2F5 | |
6-158 | Me | i-Bu | 1 | C2F5 | |
6-159 | Me | s-Bu | 1 | C2F5 | |
6-160 | Me | t-Bu | 1 | C2F5 | |
6-161 | Me | Me | 2 | C2F5 | 8.03(d,1H),7.82(d,1H),3.44(s,3H),2.74(s,3H) |
6-162 | Me | Et | 2 | C2F5 | |
6-163 | Me | n-Pr | 2 | C2F5 | |
6-164 | Me | i-Pr | 2 | C2F5 | |
6-165 | Me | n-Bu | 2 | C2F5 | |
6-166 | Me | i-Bu | 2 | C2F5 | |
6-167 | Me | s-Bu | 2 | C2F5 | |
6-168 | Me | t-Bu | 2 | C2F5 | |
6-169 | Et | Me | 0 | C2F5 | |
6-170 | Et | Et | 0 | C2F5 | |
6-171 | Et | n-Pr | 0 | C2F5 | |
6-172 | Et | i-Pr | 0 | C2F5 | |
6-173 | Et | n-Bu | 0 | C2F5 | |
6-174 | Et | i-Bu | 0 | C2F5 | |
6-175 | Et | s-Bu | 0 | C2F5 | |
6-176 | Et | t-Bu | 0 | C2F5 | |
6-177 | Et | Me | 1 | C2F5 | |
6-178 | Et | Et | 1 | C2F5 | |
6-179 | Et | n-Pr | 1 | C2F5 | |
6-180 | Et | i-Pr | 1 | C2F5 | |
6-181 | Et | n-Bu | 1 | C2F5 | |
6-182 | Et | i-Bu | 1 | C2F5 | |
6-183 | Et | s-Bu | 1 | C2F5 | |
6-184 | Et | t-Bu | 1 | C2F5 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-185 | Et | Me | 2 | C2F5 | |
6-186 | Et | Et | 2 | C2F5 | |
6-187 | Et | n-Pr | 2 | C2F5 | |
6-188 | Et | i-Pr | 2 | C2F5 | |
6-189 | Et | n-Bu | 2 | C2F5 | |
6-190 | Et | i-Bu | 2 | C2F5 | |
6-191 | Et | s-Bu | 2 | C2F5 | |
6-192 | Et | t-Bu | 2 | C2F5 | |
6-193 | Me | Me | 0 | CF(CF3)2 | |
6-194 | Me | Et | 0 | CF(CF3)2 | |
6-195 | Me | n-Pr | 0 | CF(CF3)2 | |
6-196 | Me | i-Pr | 0 | CF(CF3)2 | |
6-197 | Me | n-Bu | 0 | CF(CF3)2 | |
6-198 | Me | i-Bu | 0 | CF(CF3)2 | |
6-199 | Me | s-Bu | 0 | CF(CF3)2 | |
6-200 | Me | t-Bu | 0 | CF(CF3)2 | |
6-201 | Me | Me | 1 | CF(CF3)2 | |
6-202 | Me | Et | 1 | CF(CF3)2 | |
6-203 | Me | n-Pr | 1 | CF(CF3)2 | |
6-204 | Me | i-Pr | 1 | CF(CF3)2 | |
6-205 | Me | n-Bu | 1 | CF(CF3)2 | |
6-206 | Me | i-Bu | 1 | CF(CF3)2 | |
6-207 | Me | s-Bu | 1 | CF(CF3)2 | |
6-208 | Me | t-Bu | 1 | CF(CF3)2 | |
6-209 | Me | Me | 2 | CF(CF3)2 | |
6-210 | Me | Et | 2 | CF(CF3)2 | |
6-211 | Me | n-Pr | 2 | CF(CF3)2 | |
6-212 | Me | i-Pr | 2 | CF(CF3)2 | |
6-213 | Me | n-Bu | 2 | CF(CF3)2 | |
6-214 | Me | i-Bu | 2 | CF(CF3)2 | |
6-215 | Me | s-Bu | 2 | CF(CF3)2 | |
6-216 | Me | t-Bu | 2 | CF(CF3)2 | |
6-217 | Et | Me | 0 | CF(CF3)2 | |
6-218 | Et | Et | 0 | CF(CF3)2 | |
6-219 | Et | n-Pr | 0 | CF(CF3)2 | |
6-220 | Et | i-Pr | 0 | CF(CF3)2 | |
6-221 | Et | n-Bu | 0 | CF(CF3)2 | |
6-222 | Et | i-Bu | 0 | CF(CF3)2 | |
6-223 | Et | s-Bu | 0 | CF(CF3)2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-224 | Et | t-Bu | 0 | CF(CF3)2 | |
6-225 | Et | Me | 1 | CF(CF3)2 | |
6-226 | Et | Et | 1 | CF(CF3)2 | |
6-227 | Et | n-Pr | 1 | CF(CF3)2 | |
6-228 | Et | i-Pr | 1 | CF(CF3)2 | |
6-229 | Et | n-Bu | 1 | CF(CF3)2 | |
6-230 | Et | i-Bu | 1 | CF(CF3)2 | |
6-231 | Et | s-Bu | 1 | CF(CF3)2 | |
6-232 | Et | t-Bu | 1 | CF(CF3)2 | |
6-233 | Et | Me | 2 | CF(CF3)2 | |
6-234 | Et | Et | 2 | CF(CF3)2 | |
6-235 | Et | n-Pr | 2 | CF(CF3)2 | |
6-236 | Et | i-Pr | 2 | CF(CF3)2 | |
6-237 | Et | n-Bu | 2 | CF(CF3)2 | |
6-238 | Et | i-Bu | 2 | CF(CF3)2 | |
6-239 | Et | s-Bu | 2 | CF(CF3)2 | |
6-240 | Et | t-Bu | 2 | CF(CF3)2 | |
6-241 | Me | Me | 0 | CHF2 | |
6-242 | Me | Et | 0 | CHF2 | |
6-243 | Me | n-Pr | 0 | CHF2 | |
6-244 | Me | i-Pr | 0 | CHF2 | |
6-245 | Me | n-Bu | 0 | CHF2 | |
6-246 | Me | i-Bu | 0 | CHF2 | |
6-247 | Me | s-Bu | 0 | CHF2 | |
6-248 | Me | t-Bu | 0 | CHF2 | |
6-249 | Me | Me | 1 | CHF2 | |
6-250 | Me | Et | 1 | CHF2 | |
6-251 | Me | n-Pr | 1 | CHF2 | |
6-252 | Me | i-Pr | 1 | CHF2 | |
6-253 | Me | n-Bu | 1 | CHF2 | |
6-254 | Me | i-Bu | 1 | CHF2 | |
6-255 | Me | s-Bu | 1 | CHF2 | |
6-256 | Me | t-Bu | 1 | CHF2 | |
6-257 | Me | Me | 2 | CHF2 | |
6-258 | Me | Et | 2 | CHF2 | |
6-259 | Me | n-Pr | 2 | CHF2 | |
6-260 | Me | i-Pr | 2 | CHF2 | |
6-261 | Me | n-Bu | 2 | CHF2 | |
6-262 | Me | i-Bu | 2 | CHF2 |
编号 | X | R1 | n | Y | 物理数据:1H-NMR:δ[DMSO-d6] |
6-263 | Me | s-Bu | 2 | CHF2 | |
6-264 | Me | t-Bu | 2 | CHF2 | |
6-265 | Et | Me | 0 | CHF2 | |
6-266 | Et | Et | 0 | CHF2 | |
6-267 | Et | n-Pr | 0 | CHF2 | |
6-268 | Et | i-Pr | 0 | CHF2 | |
6-269 | Et | n-Bu | 0 | CHF2 | |
6-270 | Et | i-Bu | 0 | CHF2 | |
6-271 | Et | s-Bu | 0 | CHF2 | |
6-272 | Et | t-Bu | 0 | CHF2 | |
6-273 | Et | Me | 1 | CHF2 | |
6-274 | Et | Et | 1 | CHF2 | |
6-275 | Et | n-Pr | 1 | CHF2 | |
6-276 | Et | i-Pr | 1 | CHF2 | |
6-277 | Et | n-Bu | 1 | CHF2 | |
6-278 | Et | i-Bu | 1 | CHF2 | |
6-279 | Et | s-Bu | 1 | CHF2 | |
6-280 | Et | t-Bu | 1 | CHF2 | |
6-281 | Et | Me | 2 | CHF2 | |
6-282 | Et | Et | 2 | CHF2 | |
6-283 | Et | n-Pr | 2 | CHF2 | |
6-284 | Et | i-Pr | 2 | CHF2 | |
6-285 | Et | n-Bu | 2 | CHF2 | |
6-286 | Et | i-Bu | 2 | CHF2 | |
6-287 | Et | s-Bu | 2 | CHF2 | |
6-288 | Et | t-Bu | 2 | CHF2 |
B.制剂实施例
1.粉末剂
粉末剂通过以下方式获得:将10重量份的式(I)的化合物与90重量份的作为惰性物质的滑石混合,并将混合物在锤磨机中粉碎。
2.分散性粉剂
易分散于水中的可湿性粉剂通过以下方式获得:将25重量份的式(I)的化合物、64重量份的作为惰性物质的含高岭土的石英、10重量份的木素磺酸钾和1重量份的作为湿润剂和分散剂的油酰基甲基牛磺酸钠混合,将混合物在销盘式研磨机(pinned-disk mill)中研磨。
3.分散浓缩剂
易分散于水中的分散浓缩剂通过以下方式获得:将20重量份的式(I)的化合物与6重量份的烷基酚聚乙二醇醚3重量份的异十三烷醇聚乙二醇醚(8EO)和71重量份的石蜡矿物油(沸程例如约255℃至277℃以上)混合,并将混合物在球磨中研磨至低于5微米的细度。
4.乳油
乳油通过以下方式获得:将15重量份的式(I)的化合物、75重量份的作为溶剂的环己酮和10重量份的作为乳化剂的氧乙基化壬基苯酚混合。
5.水分散性颗粒剂
通过将下述物质混合制备水分散性颗粒剂,:
75重量份的式(I)的化合物、
10重量份的木素磺酸钙、
5重量份的十二烷基硫酸钠、
3重量份的聚乙烯醇和
7重量份的高岭土,
将混合物在销盘式研磨机中研磨,并在流化床中通过在其上喷雾作为制粒液体的水而粒化该粉末。
还通过将下述物质在胶体磨机中均匀化并预粉碎制备水分散性颗粒剂:
25重量份的式(I)的化合物、
5重量份的2,2’-二萘基甲烷-6,6’-二磺酸钠、
2重量份的油酰基甲基牛磺酸钠、
1重量份的聚乙烯醇、
17重量份的碳酸钙、和
50重量份的水,
随后在球磨机中研磨该混合物,并在喷雾塔中通过单流体喷嘴将所得悬浮液雾化并干燥。
C.生物实施例
1.抵抗杂草植物的苗前除草作用
将单子叶和双子叶杂草植物的种子或根茎部分置于盛有砂质壤土的9厘米至13厘米直径的盆中,并用土壤覆盖。配制为乳油或粉剂的形式的除草剂以水分散液或悬浮液或乳液的形式施用至覆盖土壤的表面,水施用率为300至800l/ha(经换算)。将盆置于温室中并保持在对植物的进一步培育而言最优的条件下。在温室中的最优生长条件下3周至4周后,通过与现有技术公开的化合物比较,评估本发明的化合物对测试植物的效果。对比表的结果显示,所选的本发明化合物与现有技术公开的化合物相比,对广谱的经济上重要的单子叶和双子叶杂草具有更好的除草活性。
在下面的比较表中使用的缩写的含义如下:
ALOMY大穗看麦娘(Alopecurus myosuroides)
AMARE反枝苋(Amaranthus retroflexus)
AVEFA野燕麦(Avena fatua)
ECHCG稗草(Echinochloa crus galli)
MATIN无臭母菊(Matricaria inodora)
PHBPU圆叶牵牛(Pharbitis purpureum)
SETVI狗尾草(Setaria viridis)
VIOTR三色堇(Viola tricolor)
对比表1:苗前
对比表2:苗前
对比表3:苗前
对比表4:苗前
对比表5:苗前
2.对杂草植物的苗后除草作用
将单子叶和双子叶杂草植物的种子置于盛有砂质壤土的纸板盆中,用土壤覆盖并置于温室中,在良好生长条件下栽培。在播种两到三周后,在三叶期处理测试植物。将配制为可湿性粉剂或乳油的本发明化合物喷洒至植物的绿色部位的表面,水施用率为600至800l/ha(经换算)。将测试植物在温室中于最佳生长条件下保持3周至4周后,通过与现有技术公开的化合物比较,评估本发明化合物的活性。对比表的结果显示,所选的本发明化合物与现有技术公开的化合物相比,对广谱的经济上重要的单子叶和双子叶杂草具有更好的除草活性。
对比表6:苗后
对比表7:苗后
对比表8:苗后
对比表9:苗后
对比表10:苗后
对比表11:苗后
Claims (15)
1.式(I)的(4-卤代烷基-3-硫代苯甲酰基)环己二酮或其盐
其中
X为(C1-C4)-烷基,
Y为(C1-C4)-卤代烷基,除了三氟甲基,
A和Z彼此独立地为氧、-S(O)m-、-N(R5)-、羰基或(C1-C4)-亚烷基,该(C1-C4)-亚烷基被选自氧、-S(O)m-、-N(R5)-和羰基的q个单元所间断,并且被s个R6基团所取代,
R1为(C1-C4)-烷基,
R2为羟基、SR7、NR8R9,
R3和R4彼此独立地为氢或(C1-C4)-烷基,
R5为氢、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-烷基羰基、(C1-C4)-烷氧基羰基、苯基羰基或苯氧基羰基,在两个最后提及的基团中苯环被最高达p个卤原子和最高达p个选自硝基、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基,和(C1-C4)-卤代烷氧基的基团所取代,
R6为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基或(C1-C4)-烷氧基-(C1-C4)-烷基,
R7为(C1-C4)-烷基或被p个卤原子或p个选自硝基、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基,和(C1-C4)-卤代烷氧基的基团所取代的苯基,
R8为氢、(C1-C4)-烷基、或(C1-C4)-烷氧基,
R9为氢、或(C1-C4)-烷基,
或
R8和R9与它们所连接的氮原子形成5元或6元饱和的,部分饱和的或完全不饱和的环,该环包含m个选自氧、硫和氮的其他杂原子,并且该环被最高达s个卤原子和最高达p个选自氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、和(C1-C4)-卤代烷氧基的基团所取代,
m和n彼此独立地为0、1或2,
p为0、1、2、3、4或5,
q为0或1,
s为0、1、2、3、4、5、6、7或8。
2.权利要求1的式(I)的(4-卤代烷基-3-硫代苯甲酰基)环己二酮,其中
X为(C1-C4)-烷基,
Y为(C1-C4)-卤代烷基,除了三氟甲基,
A和Z彼此独立地为氧或(C1-C4)-亚烷基,
R1为(C1-C4)-烷基,
R2为羟基,且
R3和R4彼此独立地为氢或(C1-C4)-烷基。
3.权利要求1的式(I)的(4-卤代烷基-3-硫代苯甲酰基)环己二酮,其中
X为(C1-C4)-烷基,
Y为三氯甲基、二氟甲基、二氯氟甲基、氯二氟甲基、五氟乙基或七氟异丙基,
A和Z各自为(C1-C4)-亚烷基,
R1为(C1-C4)-烷基,
R2为羟基,且
R3和R4彼此独立地为氢或(C1-C4)-烷基。
4.权利要求1-3中任一项的(4-卤代烷基-3-硫代苯甲酰基)环己二酮,其中
X为甲基,
Y为氯二氟甲基、二氟甲基或五氟乙基,
A和Z彼此独立地各自为CH2或CH2CH2,
R1为甲基,
R2为羟基,
R3和R4各自为氢,且
n为1或2。
5.权利要求1-4中任一项的(4-卤代烷基-3-硫代苯甲酰基)环己二酮,其中
X为甲基,
Y为五氟乙基,
A和Z彼此独立地各自为CH2或CH2CH2,
R1为甲基,
R2为羟基,
R3和R4各自为氢,且
n为1或2。
6.一种除草组合物,其包含除草有效量的至少一种权利要求1至5中任一项所述的式(I)的化合物。
7.权利要求6的除草组合物,其与制剂助剂混合。
8.权利要求6或7的除草组合物,其包含至少一种其他的选自杀昆虫剂、杀螨剂、除草剂、杀真菌剂、安全剂和生长调节剂的杀虫活性化合物。
9.权利要求8的除草组合物,其包括安全剂。
10.权利要求8或9的除草组合物,其包括其他的除草剂。
11.一种防治不想要的植物的方法,包括将有效量的至少一种权利要求1至5中任一项所述的式(I)的化合物或权利要求6至10中任一项所述的除草组合物施用于植物或施用于不想要的植物生长的场所。
12.权利要求1至5中任一项的式(I)化合物或权利要求6至10中任一项所述的除草组合物用于防治不想要的植物的用途。
13.权利要求12的用途,其中式(I)化合物用于在有用植物作物中防治不想要的植物。
14.权利要求13的用途,其中有用植物是转基因有用植物。
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CN106008290A (zh) * | 2016-05-16 | 2016-10-12 | 安徽久易农业股份有限公司 | 一种环磺酮的制备方法 |
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BR112013001406B1 (pt) * | 2010-07-21 | 2018-10-09 | Bayer Ip Gmbh | (4-trifluor-metil-3-tiobenzoil)ciclohe-hexa-nodionas, seu uso, agentes herbicidas, e processo para combater plantas indesejadas |
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JP2013532647A (ja) | 2013-08-19 |
BR112013001567B1 (pt) | 2019-01-29 |
US8603947B2 (en) | 2013-12-10 |
KR101911761B1 (ko) | 2018-10-25 |
EP2595955B1 (de) | 2016-11-30 |
IL224316A0 (en) | 2013-03-05 |
BR112013001567A2 (pt) | 2016-05-10 |
JP5890831B2 (ja) | 2016-03-22 |
EP2595955A1 (de) | 2013-05-29 |
KR20130091747A (ko) | 2013-08-19 |
MX2013000798A (es) | 2013-02-27 |
US20120021904A1 (en) | 2012-01-26 |
IL224316A (en) | 2017-08-31 |
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