TW312692B - - Google Patents
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- TW312692B TW312692B TW085105110A TW85105110A TW312692B TW 312692 B TW312692 B TW 312692B TW 085105110 A TW085105110 A TW 085105110A TW 85105110 A TW85105110 A TW 85105110A TW 312692 B TW312692 B TW 312692B
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- 238000011049 filling Methods 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 description 150
- 125000001424 substituent group Chemical group 0.000 description 100
- -1 Ci-c6-halogenated alkyl Sulfur Chemical compound 0.000 description 83
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 60
- 229910052731 fluorine Inorganic materials 0.000 description 60
- 239000011737 fluorine Substances 0.000 description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 48
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 43
- 229910052801 chlorine Inorganic materials 0.000 description 43
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000012298 atmosphere Substances 0.000 description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 19
- 229910052794 bromium Inorganic materials 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 19
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 16
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 8
- 241001124076 Aphididae Species 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000607479 Yersinia pestis Species 0.000 description 8
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- 241000500437 Plutella xylostella Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 4
- 235000011613 Pinus brutia Nutrition 0.000 description 4
- 241000018646 Pinus brutia Species 0.000 description 4
- 241000256251 Spodoptera frugiperda Species 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 238000003971 tillage Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000239290 Araneae Species 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000006013 carbendazim Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000002079 cooperative effect Effects 0.000 description 3
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 3
- 229960003887 dichlorophen Drugs 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000005554 pyridyloxy group Chemical group 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 230000007480 spreading Effects 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000239223 Arachnida Species 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000238421 Arthropoda Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
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- 239000005895 Esfenvalerate Substances 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000005809 Metiram Substances 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
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- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 2
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- 238000002844 melting Methods 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
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- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000021108 sauerkraut Nutrition 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 239000009490 scorpio Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000004233 talus Anatomy 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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- C07—ORGANIC CHEMISTRY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
312892 A7 B7 五、發明説明(i ) 本發明相閫於一種5,6-二氫-1,3-哼哄類之新穎製法, 這類化合物有部分係新穎化合物,本發明也相《於新穎的 5,6-二氫-1,3-晖畊類,及其製備中之新穎中間物與Μ其 用於防治動物類有害生物之用途。 已知,5,6-二氫-1,3-垮畊類係令具式(Α)之胺基酵類與 具式(Β)之羧酸類,在脫水劑存在下反應而得,其反應方 程式為: Η,Ν
R. I • CH HO (A)
R"-COOH -2H2〇 RM 0
R_ IsT
(請先閲讀背面之注意事項再填寫本頁) •^. (B) (參考本說明文的 EP-A 0 635 500 與VO-A 94/14783)。 另種已知的5,6-二氫-1,3-晬畊類製法為,先將具式 (A)之胺基酵類與具式(〇之酸氯化物類反懕,接著Μ脫 水劑將所得具式(D)之醢胺基酵類環化,其反應方程式為 ,νβ Γ 經濟部中央標準局員H消費合作衽印製 Η2Ν
R· I • CH HO (A)
Rw-CO-CI
Base -HC!
R· I XH R" HN 一Λ
O HO -h2o R·
N又 R" O (C) (D) (參考本說明文的 EP-A 0 635 500 與WO-A 94/14783) -3 - 本紙張尺度逋用中國國家揉準(CNS ) A4规格(210X297公釐) 312692 A7 B7 五、發明説明(2 ) 此外,己知5,6-二氫-1,3-啐阱類可令具式(E)之胺基 酵類與具式(F)之腈類,在铑錯合物存在下,遘當地添加 二膦類下,使之反應而得,其反應方程式為:
H2hT RIV V ^rRv| rv»
+ RM-CN -HCN -h2o NΛ.
RIV RV
六中1 rVH (E) (F) (參考本說明文的JP-A 06 298 746)。 然而,上述已知的合成法中,產物的收率並不令人滿意 ,尤其是從整個製程來說,即,包括製備必需之起始物質 ,式(A)與式(E)之肢基酵類開始,经多重步驟與使用昂貴 的前驅物與适原劑下,產量仍不夠多,另外尚需克服額外 的适原劑與溶劑之實質用董的技術問題,且製程中的某些 步驟尚需於惰性氛睡下進行。 目前已發現,具式(I)之5,6-二氫-1,3-Bf畊類 經濟部中央橾準局員工消費合作社印製 式中
X ① A 代表經取代的苯基,或代表各情形選擇地经取代之萘 -4 - (請先閲讀背面之注意事項再填寫本頁)
本紙張A度適用中國國家榇準(CNS ) A4%格(210X297公釐) A7 B7 312692 五、發明説明(3 ) 基,吡啶基,噻吩基或吡唑基,且 B 代表氫,烷基,烷氧基烷基,烷硫基烷基,鹵代烷基, 烯基,選擇地经取代的環烷基,或代表各情形選擇地 經取代矣苯基,苯基烷基,苯基烯基,苯氧基烷基, 苯硫基烷基,吡啶基或2-或3-吡咯基。 可製自: 令具式(II)之醢胺衍生物類 B r1 a-co-nh-ch-n^ ^ (Π) R2 式中 A 與B的含義同前且 R1與R2為相同或相異基且於各情形代表烷基,或與連 结它們的N原子一起代表選擇經诹代的雜環 在氯化氫氣體與催化劑存在下,在遘當的稀釋劑中,使與 乙烯反懕。 令人驚異地,依本製法,即使因乙烯的低反應性而未見 明顯反懕之情況下,亦可製得高產率及高純度的具式(I) 之5,6-二氫-1,3-垮畊類。 故本發明的反應除了能改菩產率外,尚有容易進行之優 點,特別是K包括製備前驅物之全部製程而言(也請參考 製備實例)。 式(I)係本發明所要製備的化合物之化學式的一般定義。 上述及後面所提式中較佳的取代基或基團範圃述之於後文。 -5 - (請先閲讀背面之注意事項再填寫本萸) .4. 訂 經濟部中央標準局員工消費合作社印製 本紙張尺度適用中國國家揉準(CNS > A4规格(210X297公嫠} 312692 經濟部中央標準局員工消費合作社印製 Μ Β7 五、發明説明(4) A 宜代表苯基,其可帶有一至五個相同或相異的K下取 代基•·鹵素,C! -Cs -烷基,Ci -CB -烷氧基,Ci -C6 -鹵代烷基,Ci -C6 -鹵代烷氧基,Ci -C6 -鹵代 烷硫基,硝基,氰基或為可選擇地帶有一至五個相同 或相異Μ下取代基之苯基:鹵素,Ci -C6 -烷基,h -C6 -焼氧基,Cl -C6 -鹵代烧氧基,Cl -C6 -燒硫 基與Ci -c6 -鹵代烷硫基, 或代表可選擇地帶有一至三個相同或相異的K下取代 基之萘基:鹵素,Ci -C6 -烷基,Ci -c6 -烷氧基與 Ci -c6 -鹵代烷氣基, 或代表可選擇地帶有一至三個相同或相異的K下取代 基之吡啶基:鹵素,Ci -C6 -烷基,Ci -c6 -烷氧基 ,Ci -C6 -鹵代烷基,Ci -c6 -鹵代烷氧基與氰基, 或代表可選擇地帶有一至三個相同或相異的以下取代 基之唾吩基:鹵素與Ci -C6 -烷基, 或代表可選擇地帶有一至三個相同或相異的K下取代 基之蔡基:齒素與Cl -C3 -焼基。 B 宜代表氫,Ci -C6 -烷基,Cl -C6 -烷氧基-Cl -C6 -烧基,Cl -C6 _焼硫基-Cl -C6 -焼基,Cl -C6 -歯 代院基與C2 _C6 _稀基, 或代表可選擇地帶有一至五個相同或相異的M下取代 基之C3 -C7 -環烷基:鹵素,Ci -Cs -烷基,Ci -Cs “燒氧基,Ci -Cs -鹵代烷基與Ci -C6 -鹵代烷氧基, 或代表可選擇地帶有一至三個相同或相異的K下取代 -6 - (請先閲讀背面之注意事項再填寫本頁) 訂 線 本紙張尺度適用中國國家標準(CNS > A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(5 ) 基之吡啶基:鹵素,Ci -C6 -烷基,Q -c6 -烷氣基 ,Ci -C6 -鹵代烷基,Ci -c6 -鹵代烷氧基與氰基, 或代表各可選擇地帶有一至二俚相同或相異的鹵素與 Cl一-C4 _烷基之ct -吡咯基或冷-吡咯基, 或代表苯基,其可帶有K下取代基:羥基,CHO,氰 基,栽基,聚_Ci -Ce -焼氧基-Ci -Ce -烧基或Ci -Ce -烧氧基栽基 或代表苯基,苄基,苯乙-1-基,苯乙-2-基,苯氧甲 基,苯硫基甲基,苯硫乙-1-基,苯氧乙-1-基,苯氧 乙-2-基或苯乙基,其各可選擇地在其苯環上帶有一 至五個相同或相異之取代基,各情況下的遘當取代基 為 鹵素,
Cl -Cl 8 -燒基, "
Ci -燒氧基_Ci _Ce -焼基,
Ci -C8 -鹵代烷氧基,
Ci -C4 -鹵代烷基,
CdL -Ci 8 -烷氧基,其鍵間可選擇地另插入1至3個氧 原子,
Cl -Cl 8 -焼硫基,
Cl -C8 -鹵代烷硫基, 三_(Ci _Ce )-焼基砂烧基, 苯基-二-(Ci -Ce )*"燒基砂焼基》 3,4-二氟甲二氣基, -7 ~ 本紙張尺度適用中國國家標準(CNS > A4規格(210X297公羡) (請先閱讀背面之注意事項再填寫本頁)
T 經濟部中央標準局員工消費合作社印製 312692 a? _B7________ 五、發明说明(6 ) 3,4-四氟乙二氧基, 稠合的苯並基, 稠合的C3 -C4 -烷二基, 苄基亞胺基氧甲基,可選擇地經齒素,Ci -C4 -烷基 或C3 -c6 -環烷基取代, 瓖己基或環己氧基,各可選擇地經。-Cs -烷基,Ci -C6 -烷氧基,環己基或笨基取代, 吡啶氧基,其可番擇地帶有一或二個相同或相異之以 下取代基:鹵素,Ci -C4 -烷基與Ci -C4 -鹵代烷基, 苯基,笨基-Ci -c6 -烷基,苯氧基,苯硫基,苯基-Cjl -C6 -烷氧基或苄硫基,各可選擇地帶有一至五個 相同或相異之Μ下取代基:鹵素,Ci -CdL 2 -烷基與 Cl -C4 -鹵代烷基,Cl芄1 2 -烷氧基,Cl -鹵 代燒氧基,Ci -Ce -燒氧基-Ci〜C6 -燒基,Ci -Ce -烷氧基-乙烯氧基,Ci -C6 -烷硫基與Ci -C6 -鹵代 烷硫基。 A 尤宜代表苯基,其帶有一至四個相同或相異的Μ下取 代基:氣,氣,漠,Cl -C3 -燒基》Cl -C3 -燒氣基 ,Ci -c3 -烷硫基,選擇地帶有一至五個相同或相異 之氟與氯為取代基之C1 -C2 -烷基,帶有一至五個相 同或相異之氟與氛為取代基之。-C4 -烷氧基,scf3 ,schf2 ,硝基,気基,選擇地帶有一至四個相同或 相異Μ下取代基之苯基:氟,氯,溴,Cl -C4 -烷基 ,Cl -C4 -燒氧基,Cl -C4 -烧硫基,帶有一至五個 -8 _ 本纸張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) (請先閱讀背面之注$項再填寫本頁) 訂 - 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(7 ) 相同或相異之氟與氛為取代基之Ci -c2 -烷基,帶有 一至五個相同或相異之氟與氯為取代基之Cl -C4 -烷 氧基,SCF3 或 SCHF2, 或代表選擇地帶有一至三個相同或相異Μ下取代基之 萘基:氟,氛,Ci -Cb -烷基,Ci -C6 -烷氧基與h -c6-烷氧基,其可帶有一至三個相同或相異之氟與 氯為取代基, 或代表選擇地帶有一或二個相同或相異Μ下取代基之 吡啶基:氟,氯,Ci -C3 -烷基,Cl -c3 -烷氧基, CF3,OCF3與氰基, 或代表選擇地帶有一或二個相同或相異以下取代基之 噻吩基:氯,溴,甲基與乙基, 或代表選擇地帶有一至三個相同或相異K下取代基之 吡咯基:氟,氯,溴與Ci -C3t烷基。 B 尤宜代表氣,Ci -C4 -燒基,Ci -C4 -焼氧基-Ci - C4 -烷基,Ci -C4 -烷硫基-Cl -C4 -烷基,Ci -C4 -由代燒基或C2 -C6 -嫌基, 或代表環丙基,環戊基或環己基,其各可遘擇地帶有 一至三個相同或相異之K下取代基:氟,氯,溴,Ci -Ο烷基,Ci -C3 -烷氧基,CF3與OCF3 , 或代表吡啶基,其可選擇地帶有一或二個相同或相異 Μ下取代基:氟,氯,Ci -C3 -烷基,Ci -C3 -烷氧 基,cf3,ocf3與氰基, 或代表σ-吡咯基或/3-吡咯基,其各可選擇地帶有一 -9 - 本纸張尺度適用中國國家標準(CNS ) A4規格(210X297公嫠) (請先159'讀背面之注意事項再填寫本頁) 訂 A7 B7 312692 五、發明説明U ) 或二個相同或相異的K下取代基:氟,氯與Ci -c3 -烷基, 或代表帶有K下取代基之苯基:CHO,氰基,羥基, 羧基,聚-Ci -C8 -烷氧基-Ci -C6 -烷基與Ci -c8 -烷氧基羰基或, 或代表苯基,节基,苯乙-1-基,苯乙-2-基,苯氧甲 基,苯硫基甲基,苯硫乙-1-基,苯氧乙-1-基,苯氧 乙-2-基或苯乙基,其各可選擇地在其苯環上帶有一 至四個相同或相異之取代基,各情況下的逋當取代基 為 氟,氯,溴, C3L -Ci 8 -烷基,
Cl -C6 -烷氧基-Ci -c8 -烷基,
Ci -c8 -烷氧基,可帶有一至六個相同或相異的氟與 氛為取代基,
Ci -c2 -烷基,可帶有一至五涸相同或相異的氟與氛 為取代基,
Cl -Cl 8 -焼氧基或-(〇C2 H4 )1-3 _0-Cl -C6 -燒 基,
Ci -Ci 5 -烷碲基,
Ci -c8 -烷硫基,可帶有一至六個相同或相異的氟與 氛為取代基, 三-(Ci -c6 )-烷基矽烷基, 苯基-二-(Ci -c6 )-烷基矽烷基, 10· 請 閱 ik 意 事 項 再 訂 經濟部中央標準局員工消費合作社印製 本紙張尺度逋用中國國家操準(CNS ) Α4规格(210Χ297公釐) 312692 A7 ____B7 五、發明説明(3 ) 3.4- 二氟甲二氧基, 3.4- 四氟乙二氧基, 稠合的苯並基, 稠合的C4 -烷二基, Μ下基團
、CH: 、CH
(請先閲讀背面之注意事項再填寫本頁) -t 經濟部中央標準局貝工消費合作社印製 環己基或環己氧基,各可選擇地經。-C4 -烷基,Ci -C4 -烷氧基,環己基或苯基取代, 吡啶氧基,其可選擇地帶有一或二個相同或相異之Μ 下取代基:氟,氯與CF3 , 苯基,苯基-Ci -C6 -烷基,苯氧基,苯磙基,苯基-Ci -C6 -烷氣基或苄硫基,各可選擇地帶有一至四個 相同或相異之Μ下取代基:氟,氯,溴,Ci 2 - 烷基,Ci -C4 -烷基,其可帶有一至六個相同或相異 的氟與氯為取代基,Cl -Cl 2 -烷氧基,Cl -C4 -烷 氧基,其各帶有一至六個相同或相異的氟與氛為取代 基,Ci -C4 -烷氧基-Ci -C4 -烷基,Ci -C4 -烷氧 基乙烯氧基,Ci -c4 -烷硫基或。-C4 -烷硫基,其 -11- 訂 本紙張尺度逋用中國國家榡準(CNS ) A4規格(210X297公釐) 經濟部中央橾準局員工消費合作社印装
AJ B7___ 五、發明説明(1〇) 可帶有一至六個相同或相異的氟與氯為取代基, A 槿逋宜代表苯基,其帶有一至三個相同或相異的K下 取代基:氟,氯,溴,Ci -C3 -烷基,Ci -C3 -烷氧 基,Ci -C3 -烷硫基,濟有一至五個相同或相異之氟 與氯為取代基之Ci -C2 -烷基,帶有一至五個相同或 相異之氟與氮為取代基之Ci -C4 -烷氧基,SCF3 , SCHF2,硝基,氮基,或選擇地帶有一至四個相同或 相異之Μ下取代基之苯基:氟,氯,溴,Ci -C3 -烷 基,Ci -C3 -烷氧基,Ci -C3 -烷硫基,帶有一至五 個相同或相異之氟與氯為取代基之Ci -C2 -烷基,帶 有一至五個相同或相異之氟與氯為取代基之。-C4 -烷氧基,SCF3或SCHF2。 B 極適宜代表氫,Ci -C4 -烷基,Ci -C4 -烷氧基-Ci -C4 -烧基》Ci -C2 -焼硫基-C4 -烧基,Cl -C4 -鹵代烷基或C2 -C4 -烯基, 或代表環丙基,環戊基或環己基,其各可選擇地帶有 一至三個相同或相異之Μ下取代基:氟,氛,CH3 , C2 Hs , OCH3 , CF3 或 OCF3 , 或代表吡啶基,其可選擇地帶有一或二涸相同或相異 Μ下取代基:氟,氛,CH3 ,C2 H5,〇CH3,CF3, 〇CF3與氰基, 或代表α-吡咯基或/9-吡咯基,其各可選擇地帶有一 或二個相同或相異的K下取代基:氟,氛,CH3與 〇2 Ηδ » (請先閲讀背面之注$項再填寫本頁) 訂· 本紙張尺度適用中國國家標隼(CNS ) Α4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 B7 五、發明説明(n) 或代表帶有Μ下取代基之苯基:CHO,氰基,羥基, 羧基,二-Ci -C6 -烷氧基-Ci -C4 -烷基或Ci - 烷氧基羰基, 或代表苯基,苄基,苯乙-1-基,苯乙-2-基,苯氧甲 基,苯硫基甲基,苯硫乙-1-基,苯氧乙-1-基,苯氧 乙-2-基或苯乙基,其各可選擇地在其苯環上帶有一 至四個相同或相異之取代基,各情況下的遘當取代基 為 戴,氣,?舆,
Ci -Ci 8 -烷基,
Cl -Cs -烷氧基-Ci -C8 -烷基,
Ci -C8 -烷氧基,可帶有一至六個相同或相異的氟與 氯為取代基,
Ci -C2 -烷基,可帶有一至五'個相同或相異的氟與氛 為取代基,
Cl -Cl 8 -焼氧基或 _(〇C2 H4 )1-3 «1 -C6 -燒 基,
Ci -Ci 5 -烷硫基,
Cl -c8 -烷硫基,可帶有一至六個相同或相異的第與 氣為取代基, 三-(Ci -c6 )-烷基矽烷基, 苯基-二-(Ci -C6 )-烷基矽烷基, 3.4- 二氟甲二氧基, 3.4- 四氟乙二氧基, -13- 本紙張^度逋用中國國家標準(CNS ) A4规格(210X297公釐) (請先聞讀背面之注意事項再填寫本頁) -i· 訂- )12692 五、發明説明(12 ) 稠合的苯並基, 稠合的C4 -烷二基, K下基團
CH,
經濟部中央標準局員工消費合作社印製 A7 B7
?3H7-i
環己基或環己氧基,各可選擇地经Ci -C4 -烷基,Cl -C4 -烷氧基,環己基或苯基取代, 吡啶氧基,其可選擇地帶有一或二偁相同或相異之Μ 下取代基:氟,氛與CF3 , ^ 苯基,苯基-c6 -烷基,苯氧基,苯硫基,苯基-Cl -C6 -烷氧基或苄硫基,各可選擇地帶有一至四個 相同或相異之K下取代基:氟,氛,溴,Ci -Ci 2 - 烷基,Ci -c4 -烷基,其可帶有一至六個相同或相異 * 的氟與氯為取代基,Ci -Ci 2 -烷氧基,Ci -c4 -烷 氧基,帶有一至六個相同或相異的氟與氯為取代基, Ci -C4 -烷氧基-Ci -C4 -烷基,Ci -C4 -烷氧基乙 烯氧基,Cl -C4 -烷硫基或。-C4 -烷硫基,其帶有 一至六個相同或相異的氟與氛為取代基。 可依本法製得的較佳化合物類為具式(la)之物質 -14- (請先閲讀背面之注意事項再填寫本頁)
本紙張尺度適用中國國家揉準(CNS ) A4規格(210X297公釐) A7 B7 (la) 五、發明説明(丨3 )
B
Μ-S 人〕 式中 A具有如前述一般的、癱宜的、更適宜的與棰遘宜的定 義且 B1代表可帶有一至五個相同或相異取代基之苯基,遘當 的取代基如同前面B項下所定義之適宜的、更癰宜的 與極缠宜的苯基。 可依本法製得的極佳化合物類為具式(I)之下述化合物 ----------^Ί-- (請先閲讀背面之注意事項再填寫本頁y
A 〇 (I) i r
式中 A B 經濟部中央標準局員工消費合作社印製 代表被一或二個相同或相異的,_自氣與氛的取代基 取代的苯基且 代表可帶有一至三俚相同或相異的Μ下取代基之举基 ••氟,氯,溴,Ci -C8 -烷基,Ci -C8 -烷氧基,Ci -C4鹵代烷基,L -鹵代烷氧基,Cjl -C8 -烷硫 基與C3 _C6 -環烧基或 代表可帶有一至三個相同或相異的K下取代基之苯基 :氟,氯,溴,Ci -c8 -烷基,CdL -c8 -烷氧基,Ci -15- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公董) 312692 at B7 五、發明説明(14 ) -C4齒代焼基,Ci -C4 -齒代综氧基,Ci -Ce **焼硫 基與c3 -C6 -環烷基或 代表帶有一個K下取代基之苯基:苯基,苯基-Ci -c3 -烷基,苯氧基剪节氧基,於其苯環上各可選擇地帶 有一或二個相同或相異的K下取代基:氟,氯,溴, Cl -C6 -烷基,Cl -C6 -烷氧基,Cl -C4鹵代烷基 與Ci -C4 -鹵代烷氧基, 或代表吡啶基或2-或3-吡咯基,其各可帶有一或二個 相同或相異的Μ下取代基:氟,氯,甲基,乙基與三 氟甲基,或 代表经Κ下取代基取代之苯基:CHO,羥基,氰基, 羧基,二-Ci -C6 -烷氧基-Cl -C4 -烷基或Ci -Cs -烷氧基羰基。 如果,例如,在氯化氫氣體存在下,並K催四氱化鈦為 催化劑時,使用N-[嗎啉-4-基(4-特丁基苯基)-甲基]-2,6 -二氟苯醢胺與乙烯為起始物質之情況,依本發明的製法, 其反懕方程式為: (.請先閲讀背面之注意事項再填寫本頁)
T 經濟部中央標準局員工消費合作社印製
_16_ 本紙張尺度適用中國國家標準(CNS > A4规格(210X297公釐) 312692 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明(15 ) 本製法中被做為起始物質使用之酿胺衍生物,K化學式 (II)代表,並給予一般定義。於式(II)中,A與B宜,或 更濂宜具有如前面敘述依本製法可被製備出的式(I)化合 物中相闞的逋宜、更遘宜、極適宜的A與B。 R1 與R2為相同或相異基且缠宜代表h -C4 -烷基,特 別是甲基,乙基或正丙基或異丙基,或與其連结的氮 原子一起代表五元或六元雜環,其可選擇地帶有一至 五個,宜為一或兩個,相同或相異的取代基且取代基 上可選擇地含有一或兩個(較好為一個)的其他類雜原 子,例如0, S或NR,可被提及的取代基為,特別 是,Ci -C4 -烷基與Q -C4 -烷氧基,且R代表烷基 ,宜為G -C4 -烷基,或選擇經取代的芳基,特別是 苯基,其可選擇经一或兩個相同或相異的取代基取代 ,宜被提及的取代基為:鹵素ς Ci -C4 -烷基與L -C4 -鹵代烷基,Ci -C4 -烷氧基,Ci -C4 ·鹵代烷氧 基,Ci -C4 -烷硫基與。-C4 -鹵代烷硫基。 部分其B為氫之式(II)的醢胺衍生物類係已知者(參考, 例如,Liebigs Annalen 343. 207(1905) and Bull. Soc Chi丨· France 1979. II, 409-414) 0 新穎且為本發明之目的物係具式(Ila)之醢胺衍生物
B2 I A-CO-NH-CH-lsT ,R1 •、R2
Ola) (請先閱讀背面之注意事項再填寫本頁)
*1T 式中 -17- 本紙張尺度適用中國國家橾準(CNS >八4規格(2丨0X297公嫠) 經濟部中央樣準局員工消費合作社印製 A7 B7 五、發明説明(16 ) A, R1與R2的含義同前且 B2含義同前逑給B之定義,但不包括氬。 可製取具式(Ila)之醢胺衍生物之方法為,例如,令具 式(III)之醢胺類 A-CO-HH2 (III) 式中 A 含義周前 與式(IV)之醛反應 B2 -CHO (IV) 式中 B2含義同前 並與具式(V)之胺類 ,’ R1 H-H’ (V) 式中 R1與R2的含義同前, 在逋當的稀釋劑中反應。 如果,例如,使用2,6·•二氟苯醢胺,4-特丁基苄醛與 嗎啉做為起始物質時,製備此種式(II)的醢胺衍生物類的 反應遇程可摘逑如下: -18- 本紙張尺度適用中國國家揉準(CNS ) A4規格(210X297公釐) (請先聞讀背面之注意事項再填寫本頁) 訂 312692 A7 hi 五、發明説明(π )
F
CHO + HN O co-nh2 + (CH3)3C-r y
經濟部中央標準局員工消費合作社印製 製備此種式(II)的醯胺衍生物所需之起始物質,式(III) 的醢胺類,式(IV)的醛類與式(V)的叔胺類,係通常已知 且可使用習用方法製取者。 進行本製法製備式(II)之醢胺衍生物時,適用的稀釋劑 為所有適用於這類習用方法之惰性有機溶劑。較適宜者如 下:酵類,例如甲醇或乙醇;酯類r例如,乙酸甲酯或乙 酸乙酯;鲢類,例如,二乙醚,甲基特丁基醚,乙二酵 二甲醚,四氫呋喃或二噁烷,另外如腈類,例如,乙腈; 此外為選擇地经鹵化的脂族、環腊族或芳族烴類,例如, 二氯甲烷,氛仿,四氯化碳,己烷,環己烷,苯,甲苯, 二甲苯或氯苯;以及亞租類,例如,二甲亞理。 進行本製法製備式(II)之醢胺衍生物時,癯用的溫度範 圍甚廣。通常於介於0與120*C ,更宜於10*0至100*C的溫度 間使之反應。 進行本製法製備式(II)之醢胺衍生物時,厨每莫耳式( III)的醢胺類,通常使用1.0至1.5莫耳,更宜為使用1.0 -19- (請先閲讀背面之注$項再填寫本頁)
,1T 本紙張尺度適用中國國家標準(CNS ) Α4规格(210Χ297公釐) 經濟部中央標準局員工消费合作杜印製 A7 _B7__ 五、發明説明(18 ) 至1.2莫耳,的式(IV)之醛類與1.0至2.0莫耳,更宜為使 用1.0至1.2莫耳的式(V)之叔胺類進行反應。 本反應及反應產品的處理與單雛係依一般習用方式進行 〇 缠當地,式(II)之醢胺衍生物也可直接被反應,意指未 予先行單雛,即依本發明之製法使之與乙烯反懕,製取最 後具式(I)之產品(另請參見製備實例)。 當K之用於防治動物類有害生物時,具式(Ila)之新穎 醢胺衍生物也呈現良好的生物作用。 本發明供製備式(I)化合物之方法係於氯化氫氣體及某 種催化劑存在下進行。缠當的催化劑係路易士酸類,宜為 通渡金屬齒化物類,特別是四氯化鈦,四氯化錫與氯化鋅 〇 本發明之製法宜於稀釋劑存在下進行。 適用的稀釋劑為所有習用之有機溶劑類,例如選擇地經 鹵化的脂族、環腊族或芳族烴類。包括,例如,氛苯,二 氯苯,石油醚,己烷,環己烷,二氯甲烷,氯仿與四氛甲 烷.<> 進行本製法時,癱用的溫度範圍甚廣。通常,於介於 -120*0與+120*C ,較缠宜於10*0至100*0的溫度間反懕。 在此種溫度下,反應較好於密封容器內(加热釜中),於 反懕混合物自然產生的壓力下進行。然而,也可使用於常 壓下通入乙烯至混合物,再將未及作用的乙烯循環再通入 使用。 -20- (請先閲讀背面之注意事項再填寫本頁) 訂 本紙張尺度適用中國國家標準(CNS ) A4规格(2丨〇父297公董) 312692 五、發明説明(19 ) 另一方法為,在低溫(約-liot!)下將乙烯凝聚後,在此 種低溫下進行反應。 依本發明進行本製法時,對每莫耳式(II)之醢胺衍生物 ,通常使用介於1與5莫耳間,更逋宜使用介於1與3莫耳間 的乙烯,及使用介於1與5莫耳間,更遵宜使用介於1與4莫 耳間的氯化氫氣體與催化劑進行反懕。 反應產品的處理可依一般習用方式進行;較逋宜的方式 為,將反應混合物弄成鐮性,將其冷卻使介於0*C與10*C 間,再依習用方法將最後產品單離出來。 本發明所欲製備之式(I)的5,6-二氫-1,3-嗒畊類在大部 分情形下係已知者(參考,例如,EP-A 0 635 500與W0-A 94/14783)且被用於防治動物類有害生物。 新穎的且也為本發明之目的物係具式(lb)之化合物 (請先閲讀背面之注意事項再填寫本頁) • · 訂
D
經濟部中央標準局員工消費合作社印製 式中 A 的含義同前且 D 各代表番擇地經取代之2-或3-吡咯基,或帶Μ下取 代基之苯基:CH0,氰基,羧基,聚烷氧基烷基或烷 氧基羰基。 視取代基的本質,式(lb)的化合物可具有幾何及/或光 學異梅物或各種组成的異構物混合物。本發明涉及其各種 純態異構物及異構物混合物。 -21- 本紙張尺度適用中國國家橾準(CNS ) A4規格(210X297公釐) 經濟部中央標準局負工消費合作社印裝 A7 B7 五、發明説明(20 ) 此外,已發現,式(lb)的化合物由上述製法製得。 最後,已發現,此新穎的式(lb)化合物極適於被應用於 供防治動物類有害生物,特別是節肢戶物與線燊類。 令人驚異的,本發現之式(lb)化合物,相較於大部分其 他具類似结構的化合物,圼現更佳的防治動物類有害生物 之活性。 本發明之化合物,Μ式(lb)給予一般性定義。 之前與之後提到的化學式中,較缠宜的取代基或基團範 面,說明如後。 A 適宜代表帶有一至五個相同或相異Μ下取代基之苯基 :齒素,Ci -C6 -燒基,Ci -C6 -焼氧基,Cl -C6 -烷硫基,Ci -C6 -鹵代烷基,Cl -c6 -鹵代烷氧基^ Ci -c6 -烷硫基,硝基,氰基與苯基,其為選擇地帶 有一至五個相同或相異的Μ下取代基者:鹵素,Ci -C6 -烷基,Ci -C6 -鹵代烷基,C;L -C6 -烷氧基,Cl _齒代焼氧基,Ci -C6 -燒硫基與Ci **Ce -齒代 烷硫基, 或代表選擇地帶有一至三個相同或相異K下取代基之 吡啶基:鹵素,Ci -C6 -烷基,Ci -C6 -烷氧基,Ci -c6 -鹵代烷基,Ci -c6 -鹵代烷氧基與氰基, 或代表選擇地帶有一至三俚相同或相異Μ下取代基之 噻吩基:鹵素與Ci -c6 -烷基, 或代表選擇地帶有一至三個相同或相異Μ下取代基之 吡唑基:鹵素或Ci -C3 -烷基。 -22- (請先閱讀背面之注意事項再填寫本頁) .^Γ 訂 本紙張尺度速用中國國家橾準(CNS ) Α4規格(210Χ297公釐) 經濟部中央標準局員工消費合作社印裝 312892 a? B7 —------ " — 五、發明説明(21 ) D 遘宜代表選擇地帶有一或二個相同或相異K下取代基 之2-吡咯基或3-吡咯基:鹵素與Ci -C4 -烷基, 或代表經以下取代基取代之苯基·· CHO,羥基,氰基, 竣'基,聚-Ci -Ce -焼氧基-Ci -Cs -焼基或Ci -Ce -烷氣基羰基。 A 更缠宜代表帶有一至四個相同或相異Μ下取代基之苯 基:氟,氯,溴,Ci -C3 -烷基,h -C3 -烷氧基, Ci -C3烷硫基,Ci -C2 -烷基,其帶有一至五個相 同或相異Μ下取代基:氟與氛,Ci -C4 -烷氧基,其 帶有一至四俚相同或相異K下取代基:菝與氯,scf3 ,SCHF2 ,硝基,氰基與苯基i其為選擇地帶有一至 四個相同或相眞的以下取代基者:氟,氛,溴,Cjl -C4 -烷基,Ci -C4 -烷氧基,Ci -C4 -烷硫基,Cl --c2 -烷基,其帶有一至五個相同或相異的Μ下取代 基:氟與氛,d -C4 -烷氧基,其帶有一至五個相同 或相異的以下取代基:氟與氯,SCF3,SCHF2 , 或代表選擇地帶有一至三個相同或相異Μ下取代基之 萘基:氟,氛,溴,Ci -C6 -烷基,Ci -c6 -烷氧基 與Ci -C6 -烷氧基,其帶有一至三個相同或相異 下取代基:氟與氛, 或代表選擇地帶有一或二個相同或相異Μ下取代基之 吡啶基:氟,氯,Ci -C3 -烷基,Cn -c3 -烷氧基, cf3,ocf3與氰基, 或代表選擇地帶有一或二個相同或相異以下取代基之 -23- 本紙張尺度適用中國國家標準(CNS > Α4規格(210X297公釐) (諳先閲讀背面之注$項再填寫本頁) 、π- 經濟部中央樣準局員工消費合作社印製 A7 B7 五、發明説明(22 ) 睡吩基:氯,溴,甲基或乙基, 或代表選擇地帶有一至三俚相同或相異Μ下取代基之 吡唑基••氟,氯,溴與Ci -C3 -烷基。 D 更缠宜代表選擇地帶有一或二個相同或相異以下取代基 之2-吡咯基或3-吡咯基:氟,氯與Ci -C3 ·烷基, 或代表經K下取代基取代之苯基:CHO,羥基,氰基, 搂基,聚-Cl -C8 -焼氧基-Cl -C6 -烧基或Cl -C8 -烷氧基羰基。 A 極適宜代表帶有一至三個相同或相異Μ下取代基之苯 基:氟,氯,溴,Ci -C3 -烷基,Ci -C3 -烷氧基,
Cl -C3院硫基,Cl -C2 -烧基,其帶有一至五個相 同或相異之蕖與氯為取代基,Cl -C4 -烷氧基,其帶 有一至五個相同或相異K下取代基:氟與氯,scf3 , SCHF2 ,硝基,氰基與苯基,其選擇地帶有一至四個 相同或相異的Μ下取代基:氟,氯,溴,Ci -C3 -烷 基,Cl -C3 -燒氧基,Cl -C3 -烧硫基,Cl —C2 ~ 烷基,其帶有一至五個相同或相異的Μ下取代基:氟 與氯,Cl -C4 -燒氧基》其帶有一至五儸相同或相異 的Μ下取代基:氟與氯,SCF3,SCHF2。 B 極遘宜代表番擇地帶有一或二個相同或相異K下取代 基之2-吡咯基或3-吡咯基··氟,氯,CH3與C2 H5, 或代表經Μ下取代基取代之苯基:CHO,羥基,氰基, 羧基,二-Ci -C6 -烷氧基-Cji -C4 -烷基或Q -C6 -烷氧基羰基。 -24- 本紙張尺度適用中國國家揉準(CNS ) A4規格(210X297公釐) (請先閲讀背面之注意事項再填寫本頁〕 訂 經濟部中央樣準局員工消費合作社印製 A7 B7 _ 五、發明説明(£3 ) A 特別缠宜代表帶有一或二個相同或相異K下取代荽之 苯基:氟與氯。 D 特別癱宜代表選擇地帶有一或二個相同或相異K下取 代基之2-吡咯基或3-毗咯基:氟,氯,甲基與乙基, 或代表經Μ下取代基取代之苯基:CHO,羥基,氰基, 搂基,二-Cl _C6 -焼氧基-Cl -C4 -燒基或Cl -C6 -烷氧基羰基。 本活性化合物逋於供防治與農桊、林桊、農林產品及原 料之儲存,及衛生學領域上有鼷之動物性有害生物,特別 是節肢動物類與蜘蛛類,特別是昆蟲與蟎類。它們有效於 供防治通常為易於肪治與已具抗性之品種也逋於防治有害 生物衍化時之全部或部分階段。上述有害生物包括: 等足目,例如,球鼠婦(潮巖),鼠嫌與Porcellio scaber ° Λ 倍足網目,例如,具斑馬陸。 唇足網目,例如,食果地挨松(Geophilus carpophagus) 與家她挺屬諸種(Scutigera spec.) 〇 结閥绢目,例如,庭困么蚰。 瘅尾網目,例如,西洋衣魚。 理尾目,例如,白棘路蟲。 直翅目,例如,東方蜚蠊,美洲大蠊,馬得拉蜚蠊,徳 國蟑螂,家蟋蟀p螻蛄羼,熱帶飛蝗,殊種蚱蜢與荒地蚱 蜢。 革翅目,例如,歐洲球蠼。 -25- 本紙張尺度適用中國國家標準(CNS ) A4规格(210X297公釐) (請先閲讀背面之注意事項再填寫本頁) 訂 經濟部中央標準局員工消費合作社印製 A1 B7 五、發明説明(24 ) 等翅目,例如,網白蟻類。 目,例如》Vastatrix葡萄瘤姐,天泡瘡(Pemphigus) 厲,體蝨,盲蝨鵰與長顎蝨羼。 食毛目,例如,羽蝨屬(Trichodectes spp.)與羽蝨屬 (Danalinea spp.) 0 緦翅目,例如,溫室條蓟馬與Μ蓟馬。 異翅目,例如,椿象靥,紅椿羼(Dysdercus intermedius),甜菜擬網椿,臭盡,Rhodnius prolixus 與豬椿屬。 同翅目,例如,藿薑粉蝨,棉粉蝨,溫室粉蝨,撺蚜, 菜蚜,茶隱瘤額蚜,豆葉蚜巖,蘋果蚜蟲,桃大尾蚜,燕 麥長管蚜,瘤額蚜屬,忽布疣額蚜,管蚜(Rhopdlosiphun padi),微葉蟫靥,Mlobatus葉蟫,黑尾葉嬅,李蟠蚧, 油欖黑灰蚧,灰稻蝨,稻裼飛蝨,紅圓蚧,賀氐圓蚧,粉 蚧屬與木蝨屬。 鱗翅目,例如,[棉]釭螟蛉蟲,松尺蠖,Cheinatobia brumata, blancardella细蛾,藏[食果]巢蛾,小菜蛾, 天幕毛蟲,棕尾毒蛾,舞[毒]蛾屬,棉葉穿孔潛蛾,桔细 潛蛾》夜蛾屬,切根蟲属,地虎饜,梅斑實蛾,夜蛾羼, 甜菜夜蛾,甘藍夜蛾,松夜蛾,小夜蛾,(粘蟲)夜蛾,粉 纹夜蛾,薄果蠢蛾,粉蝶,蜞靥,瓦米蜞,地中海粉蜞, 大嫌螺,Podana捲葉蛾,reticulana捲葉蛾,霉杉捲葉蛾 ,葡萄果蠢餓,magnanima捲葉蛾與橡綠捲葉蛾。 鞘翅目,例如,[傢俱]具斑竊蠹,Rhizopertha -26- 本紙張尺度逋用中國國家揉準(CNS ) A4規格(2丨OX25»7公釐) (請先閲讀背面之注$項再填寫本頁) -^· -訂 經濟部中央標準局員工消費合作社印製 五、發明説明(25 ) doninica,(菜)大豆象,家天牛,赤楊紫 跳甲,馬鈐薯甲蟲,辣根猿葉蟲,葉甲屬,油菜藍跳甲, 墨西哥豆瓢蟲,食甲羼,鋸谷盜,象甲雇,米象雇,葡@ 黑象甲,香蕉蛀基象甲,甘藍莢象甲,苜蓿葉象甲,皮· 靥(Dernestes spp·),斑皮鼸羼,皮蠢靥(Anthrenus SPP· ),黑皮蠢靥,粉覼屬,油菜花露尾甲,蛛甲屬,金黃蛛 甲靥,麥蛛甲,擬毅盜靨,大黃粉蟲,Agriotes spp·, 金針蟲屬,鳃角金龜科,六月金龜與Costelytra zealandica ° 膜翅目,例如,角葉蜂屬,實葉蜂屬,蟻靥,櫥蟻與胡 蜂羼。 雙翅目,例如,伊蚊羼,按玟羼,庫蚊屬,黄猩猩果蠅 ,家蠅馬,廁摁屬,紅頭麗媚,錄蠅雇,Chrysomyian spp. > Cuterebra spp. , GastrophHus spp. , Hyppobosca spp.,廄螫镅靥,羊典蠅靥,皮蠅屬,牛虻屬, hortulanus毛蚊,瑞典麥桿蠅,種蠅屬,甜菜蠅靥,地中 海實媚,油攬實鎇與歐洲大蚊。 蚤目(微翅目),例如,東方鼠蚤與蚤雇。 姝形鑭目,例如,Scorpio naurus與黑寡婦球腹姝 蜱蟎目,例如,粗獅粉蟎,隱喙蜱靥,鈍緣蜱靥,雞剌 皮蟎,黑茶癭蟎,桔銹蟎,牛蜱屬,血紅扇斗蜱靥•花蛛 属,Hyalomma spp.,硬蛛屬,癯嫌(Psoroptes)靥,藩嫌 (Chorioptes)靥,疥蟎靥,媒蟎靥,苜蓿蟎,爪蟎屬與紅 葉蟥羼 -27- C#先閲讀背面之注意事項再填寫本頁) .^- 訂 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印裝 312692 at B7 五、發明説明(26 ) 這些活性化合物可被配製成習用的配方,例如溶液,乳 劑,可濕性粉劑,懸濁劑,粉劑,塵染劑,膏劑,可溶性 粉末劑,粒劑,懋浮-乳劑濃缩物,Μ活性化合物浸潤過 之中性及合成材料,與包裹於聚合物中之極细膠囊劑。 .這些配製劑係Κ已知的方法配製,例如以展延劑將活性 化合物混合,包括液態溶劑,及/或固態載劑,可選擇地 配合使用表面活性劑,例如乳化試劑及/或分散試劑,及/ 或泡沫形成劑。 使用水做為展延劑時,亦可加入,例如有機溶劑,做為 輔助溶劑。合遒的液態展延劑主要為··芳族類,例如二甲 苯,甲苯或烷基萘類;氯化的芳族與氯化的脂族烴類,例 如,氯苯類,氣乙烯類或二氯甲烷;脂族烴類,例如環己 烷或石蟠類,例如無櫬油分劃物,礦物與植物油類;酵類 ,例如丁醇或甘酵Μ及其醚類與酯類;醑類,例如丙酮, 甲基乙基酮,甲基異丁基酮或環己酮;強極性溶劑類,例 如二甲基甲醢胺與二甲亞强;Κ及水。 至於適當的固態載劑為:例如铵盥類與研细的天然礦物 類,如高嶺土、粘土、滑石、白堊土、石英、美國活性白 土、蒙脫土或矽藻土以及研细的合成確物類,例如高度分 散的矽石,鋁土與矽酸鹽類;通於製備顆粒體之固態載劑 為,例如,碾碎並分劃逯的天然岩石,如,方解石、大理 石、輕石、海泡石與白雲石,Μ及合成之有機與無機配料 之顆粒,與有機材料顆粒,例如,鋸屑、椰子殼、玉米穗 軸與菸草莖;至於適當的乳化用及/或泡沫-形成劑有:例
I -28- (請先閱讀背面之注^^項再填寫本頁) 訂 ^ 本紙張尺度適用中國國家標準(CNS ) Λ4规格(210Χ297公釐) A7 37 經濟部中央橾準局員工消费合作社印製 五、發明説明(27 ) 如,非離子與陰雄子的乳化劑類之聚氧乙烯脂肪酸酯類, 聚氧乙烯脂族酵醚類,例如,烷基芳基聚甘酵醚類,烷基 磺酸强類,烷基硫酸Μ類,芳基磺酸鹽類K及白蛋白水解 產物;至於適當的分戢劑有:例如,木質素-亞硫酸廢液 與甲基缵維素。 钻著劑類,例如,羧甲基纖維素與天然或合成的聚合物 ,圼粉狀、粒狀或乳膠態者,例如,阿拉伯膠,聚乙烯酵 與聚乙烯醋酸酯,Μ及天然磷脂質類,如腦磷脂與卵磷脂 ,Κ及合成的磷脂質類,均可被加於配方中。此外,尚可 添加無機油類或植物油類。 也有可能用及著色劑,例如,無楗色素類,如,氧化鐵 ,二氧化钛與普魯士藍,及有襪染料,如,茜素染料,偁 氮類染料與金厲酞花靑染料,以及微悬營養成分,例如鐵 '錳、硼、銅、鈷、鉬與鋅等的鹽類〇 配製劑裡通常包含介於0.1與95%重量計的活性化合物 ,Κ含有介於〇·5與90%重量計者為較佳。 本發明的活性化合物可呈供販售的配製劑,或Κ此配製 flllB成供使用的型態存在,或與其他活性化合物圼混合物 存在,其他的活性物質有如,殺盡劑,誘餌劑,消毒瑯, 殺菌劑,殺蟎爾,殺皞蟲劑,殺真菌劑,生長調節物質或 殺草劑。殺蟲劑類包括,例如磷酸路(醣)類,胺基甲酸酯 類,_酸靡類,氯化烴類,苯基脲類與微生物製劑等等。 混合物中的極佳组份為: 殺真菌劑類:-29- (請先閲讀背面之注再填寫本頁)
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T Γ 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 經濟部中央標準局負工消費合作社印製 A7 _B7_ 五、發明説明(28 ) 2-胺基丁烷;2-苯胺基-4-甲基-6-環丙基嘧啶;2’,6’-二 溴-2-甲基-4、三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-羧 苯胺;2,6-二氯-N-(4-三氟甲氧基苄基)苯醢胺;(E)-2-甲氧基亞胺-Η-甲基-2-(2-苯氧基苯基)-乙醢胺;卜羥基 喹啉硫酸Μ; (Ε)-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基氧 ]苯基卜3-甲氧基丙烯酸甲酯;(Ε)-甲氧基亞胺基[α-(鄰 甲苯氧基)-鄰-甲苯基]乙酸甲酯;2-苯基苯酚(ΟΡΡ),阿 得摩福(aldimorph),安丙基松(ampropylfos),苯胺精 (anilazine),窥雜克唾(azaconazole), 本達樂(benalaxyl),本達尼(benodanil),免賴得( benomyl),白挪巴克(binapacryl),聪苯(biphenyl), 比多農(bitertanol),保米徽素-S,溴克利(bromucon-azole),布瑞莫(bupirimate),得滅多(buthiobate)» 聚硫化鈣,四氯丹,蓋普丹,貝芬替(carbendazim), 卡保信(carboxin),快滅松,氣尼布(chloroneb),氣畢 克寧(chloropicrin),四氣異苯睛(chlorothaloni 1)» 氣唾林特(chlozolinate),古扶尼布(cufraneb),克絕, 普克力(cyproconazole),西普咲南(cyprofuram), 二氣芬(dichlorophen),二氛別唾(diclobutrazol),益 發轚,得克滅精,大克爝,二硫芬克(diethofencarb)» 待克力(difenoconazole),得滅利其(dimethirimol), 大滅芬(dimethomorph),得尼克嗤(diniconazole),大那 克(dinocap),二苯基胺,二比松(dipyrithion),普得松 (ditalimfos),睛硫現(dithianon),多寧(dodine),得 -30- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) (請先閲讀背面之注^^項再填寫本頁) 訂 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(29) 唾隆(drazoxolon), 護粒松,環氧克唑,依瑞莫,依得力(etridiazole), 芬瑞冥(fenarimol),芬布克唾(fenbuconazole),芬富南 (fenfuram),芬尼.唾盆(fenitropan),芬畢克尼(fenpi-clonil),芬普比汀(fenpropidin),芬普福(fenpropi-Borph),三苯醋錫(fentin acetate),三苯經錫(fentin hydroxide),富爾邦(ferbam),飛利隆(ferimzone), 伏寄南(fluazinam),伏二喔尼(fludioxonil),富羅寅( fluoromide),富快克睡(iluquinconazole),護砂唾( flusilazole),福碌醯胺(flusulfamide),福多寧(flu-tolanil),福採扶(flutriafol),富皮特(folpet),福 賽得·銘(fosetyl-aluminium),熱必斯(fthaiide),福 利達唑(fuberidazole),福達樂(furalaxyl),福滅克斯 (furmecyclox),克热淨(guazatirre), 六氣苯,菲克斯(hexaconazole),殺纹寧(hymexazol), 依滅列(imazalil),尹本克睡(imibenconazole),尹克他 丁(iminoctadine),丙基喜樂松(IBP),依普同(iprodi-one),亞賜圃(isoprothiolane), 嘉賜徽素,铜製劑,例如··氫氧化銅,萘酸鋦,鹼性氯氧 化鋦,硫酸飼,氧化鋦,快得寧-鋦與酸性棗紅混合物( Bordeaux mixture),錳鋦,鋅錳乃浦,錳乃浦,滅尼比 林(mepanipyrim),減普寧(mepronil),滅達樂(metala-xyl)» 滅克哩(metconazole),滅速克(methasulfocab), 滅扶連(methfuroxam),免得燸(metiram),滅硫斯(net- -31 一 本紙張尺度適用中國國家揉準(CNS ) A4規格(210X297公嫠) (請先閲讀背面之注項再填寫本頁) -i. 訂 經濟部中央標準局員工消費合作社印製 t ‘ A7 _B7_ 五、發明説明(3〇 ) sulfovax),邁克尼(ayclobutanil),二甲基二硫胺基甲 酸酯鎳,硝基塞-異丙基,尼瑞莫, 歡扶斯(ofurace),歐殺斯(oxadixyl),歐莫克(oxaao-carb),嘉保信(oxycarboxin), 平福哩(pefurazoate),平克哩(penconazole),賨克隆( pencycuron),碟二苯 Cphosdiphen),皮馬辛(pimaricin) » 派拉寧(piperalin),聚胺基甲酸醅(polycarbamate), 保粒徽素(polyoxin),撲殺熱(probenazole),撲拉克( prochloraz),撲滅寧(procymidone),普拔克(propamo-carb),普克利(propiconazole),甲基鲜乃浦(propineb〉 ,白粉松(pyrazophos),必芬諾克(pyrifenox),必滅寧 (pyrimethanil),百快隆(pyroquilon),快多淨(PCNB), 硫與硫磺製劑, 得克力(tebuconazole),得克安(t/fecloftalam),得那淨 (tecnazene),四克唾(tetraconazole),腐絕,噻安芬 (thicyofen),甲基-多保淨,得恩地(thiram),甲基-脘 克松(toclophos-methy 1),甲苯集尼得(tolyf luanid)» 三泰芬(triadimefon),三泰隆(triadimenol),三唾地 (triazoxide),三氛睡胺,三養唾(tricyclazole)» 三 得芬(tridemorph),賽福哩(triflumizole),養福寧( triforine)» 三地克唾(triticonazole), 维利徽素A,免克寧(vinclozolin), 辞乃浦,辞來(ziram)。 -32- 本紙張尺度適用中國國家標準(CNS ) A4规格(210X297公釐) (請先閲讀背面之注$項再填寫本頁) - 經濟部中央標準局員工消費合作社印製 ί12692 Α7 _Β7________ 五、發明説明(31 ) 殺菌劑類: 波諾坡(bronopol),二氣芬(dichlorphen),奈比寧(ni-trapyrin),二硫胺基甲酸二甲酯鎳,嘉賜徽素,八希力 酮(octhilinqne),呋哺羧酸,氧四環徽素,普苯唑(Pro-benazole),鍵擞素,鐵樂他拥(tecloftalam),硫酸銅及 其他鋦製劑。 殺蟲劑/殺蟎劑/殺線蟲劑類: 阿巴丁(amamectin), AC 303 630,歐殺松,克力寧,亞 蔔克(alanycarb),得滅克(aldicarb),亞滅寧(alphame-thrin),三亞媒(amitraz),亞滅汀(avermectin),AZ 60541,氮雜雷丁(azadirachtin),谷速松A,谷速松M, 亞環錫(azocyclotin), 蘇力菌,兔敵克,免扶克,免速達,貝路寧,畢芬寧,丁 滅益(BPMC),布芬普克(brofenprox),溴碟松A,必克益 ,布芬淨(buprofezin),布嘉信(butocarboxin),丁基比 達本(butylpyridaben), 卡丢松(cadusafos),加保力(carbaryl),加保扶(carbo-furan),加芬松(carbophenothion), 丁基加保扶(carbo-sulfan),培丹(cartap)» CGA 157 419, CGA 184 699»» 氛索克(chloethocarb),氣乙氧松(chlorethoxyfos), 氛芬松(chlorfenvinphos),氛福隆(chlorf luazuron), 氣滅寧(chlornephos),陶斯松(chlorpyrifos),陶斯松 Μ,順-雷滅寧(cis-resmethrin),環西寧(clocythrin), 克芬淨(clofentezine),氰松(cyanophos),環普寧(· -33- 本紙張尺度適用中國國家標準(CNS ) A4規格(2!〇Χ297公釐) (請先閲讀背面之注意事項再埃寫本頁) •飞· 訂 經濟部中央標準局員工消費合作社印製 A7 _ B7_ 五、發明説明(32 ) cycloprothrin),賽抉寧(cyfluthrin),賽洛寧( cyhalothrin),錫滿丹(cyhexatin),賽滅寧(cyper-aiethrin),克馬精(cyromazine), 第滅寧(deltamethrin),滅賜松-Μ,滅賜松-S,滅賜松-S-甲基,汰芬隆(diafenthiuron),大利松(diazinon), 二氣芬殺松(dichlofenthion),二氛松(dichlorvos), 待力松(dicliphos),雙特松(dicrotophos),二愛殺松 (diethion),二福隆(diflubenzuron),大滅松(dimetho-ate),二甲基文松(dimethylvinphos),二睡松(dioxa-thion),二硫松(disulfoton), 護粒松,伊邁丁(emamectin),愛芬化利(esfenvalerate) ,愛殺芬克(ethiofencarb),愛殺松(thion),依芬普克 (ethofenprox),依索普松(ethoprophos),依特減松( etrimphos), - 芬滅松(fenamiphos),芬雜寧(fenazaquin),芬佈賜(fenbutatin oxide)), 撲滅松 (fenitrothion), 丁基滅必益 (fenobucarb),芬硫克,芬殺克,芬普寧(fenpropathrin) ,芬皮拉(fenpyrad),芬普描(fenpyroximate),芬殺松, 芬化利(fenvalerate),懷普寧(fipronil),氟濟南(flu-azinan),福環隆(f lucycloxuron),謂賽寧(f lucythri-nate),氟芬殺隆(flufenoxuron),氣芬殺(flufenprox), 福化利(fluvalinate),大福松(fonophos),福木松(for-mothion),福賽热(fosthiazate),福芬普(fubfenprox), 福硫克(furathiocarb), -34- 本紙張尺度適用中國國家梂準(CNS ) A4規格(210Χ297公釐) (請先閲讀背面之注意事項再填寫本頁) -f.
、tT 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(33 ) HCH,飛達松(heptenophos),六福隆(hexaflumuron), 合賽多(hexythiazox), 米達克得(inidacloprid),丙基喜樂松(iprobenfos),愛 唾松(isazophos),亞芬松(isofenphos),滅必益(iso-procarb),加福松(isoxathion),沃美丁(ivermectin), λ-赛鹵寧,路芬隆(lufenuron), 馬拉松,減加松,美文松,美芬松,滅達醛,滅克松,達 馬松,滅大松,滅賜克,納乃得,治減蝨,米沃丁,亞素 番,莫克得丁(moxidectin), 乃立松,NC 184, NI 25,奈登比南(nitenpyram)» 歐滅松,歐殺滅,氧滅多松Μ,歐得普松, 巴拉松Α,巴拉松Μ,百滅寧,賽達松,福瑞松,裕必松 ,益滅松,福賜米松,巴饗松,比加普,西特松Μ,西特 松Α,佈飛松,普滅克,加護松,安丹,普硫松,普梭特 ,比美唑精,白克松,必芬松,必滅寧,畢雷念,畢達本 ,嘧啶芬,畢普芬,拜裕松, RH 5992, 饗力松,喜巴松,西拉扶芬,薩扶貼(sulfotep),薩普松, 鐵布芬得(tebufenozid),鐵芬比拉(tebufenpyrad),嫌 畢声松(tebupirimiphos),得福隆,得福寧,得滅松,特 辦(terbam),托福松,樂本松,養芬殺,硫敵克,硫划隆 thiofanox),硫滅松(thiomethon),硫那精(thionazin), 特靈精辛(thuringiensin),泰滅寧(tralonethrin),三 拉忍(triarathen),三落松(triazophos),三阿隆(tri- -35- 本紙張尺度適用中國國家橾準(CNS ) A4规格(2丨〇Χ297公釐) (請先閲讀背面之注意事項再填寫本頁) -i: 訂 A7 312692 B7 — 五、發明説明(_ ) azuron),三氛松(trichlorfon),三福隆(triflumuron), 三減沙克(trimethacarb), 繁米松(vamidothion), XMC,沙力克(xylylcarb), YI 5301/5302,热滅寧(zetamethrin)。 殺草劑類: 例如醢替苯胺頚,例如,二福芬肯(diflufenican)與除草 靈(propanil);芳基羧酸類,例如,二氯皮考林酸(dichl-oropicolinic),第卡巴(dicamba)與皮克隆(piclorm); 芳氧基烷氧酸類,例如,2,4-D, 2,4-DB, 2,4-DP,氟氛 比(fluroxypyr), MCPA, MCPP 與三氯比(triclopyr);芳 氧基-苯氧基-烷酸_類,例如,大克普-用基(diclofop-methyl),芬殺草(fenoxai>>〇i>-ethyl),伏寄普(fluazifop -buty 1),甲基合氣氟(haloxyfop-methyl)與快伏草( quizalofop-ethyl);偁氮酮類,例>如,克羅達棕(chlori-dazon)與諾伏棕(norflurazon);胺基甲酸酷類,例如, 氛普朋(chlorpropham)» 美地朋(desmedipham),氟美地 朋(phenmedipham)與普朋(propham);氣乙酿替苯胺類, 例如,拉草(alachlor),乙基拉草(acetochlor), 丁基拉 草(butachlor);甲基拉草(metazachlor),其多箪(meto-lachlor),普替拉草(preti lac^lor)與普派草(propa-chlor);二硝基苯胺類,例如,歐雜林(oryzalin),施得 圃(pendiiethalin)與三福林(trif luralin);二苯基醚類 ,例如,亞喜芬(acifluorfen),必芬諾(bifenox),氟革 芬(fluoroglycofen),福沙芬(fomesafen),鹵沙芬(halo- -36- 本紙張尺度適用中國國家標準(CNS ) A4規格(210 X 297公釐) ^1. -- — I—I —i. 1^1 I ^^1 11 I- --- ^^1 I I - — · -- >—i -11- .........- 1^1 (請先聞讀背面之注意事項再填寫本页) 經濟部中央標準局員工消費合作社印製 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(35 ) safen),樂特芬(lactofen)與復祿芬(oxyfluoorfen);脲 類,例如,氛多龍(chlortolruon),達有龍(diuron),氣 美龍(fluometuron),愛普龍(isoproturon),理有龍( 1 inuron)與甲苯塞龍(methabenzthiazuron);淫基肢類, 例如,亞汰草(alloxydim),施索定(clethodim),環氧定 (cycloxydin),西殺草(sethoxydim)與特殺箄(tralkoxy-dim);眯唑咐酮類,例如,眯沙比(imazethapyr),眯雜 本(imazamethabenz),蹄雜比(imazapyr)與蹄克林(imaza-quin;腈類,例如,溴氧尼(broaoxynil),二氯比尼(di-chlobenil)與依氧尼(ioxynil);氧乙醯胺類,例如,美 芬納特(mefemacet);磺醯脲類,例如,醯胺基速隆( amidosulphuron),苯速隆-甲基(bensulphuroji-methyi), 氣隆-乙基(chlorimuron-ethyl,氯速隆(chlorsulphuron) ,西諾速隆(cinosulphuron),美班修-甲基(netsulphuron-methyl),尼可速隆(nicosulphuron),普密速隆(primi-sulphuron),百速隆(pyrazosulphuron-ethyl),西分速 隆(thifensulphuron-methyl),三速隆(triasulphuron) 與三苯隆-甲基(tribenuron-methyl);硫胺基甲酸醅類, 例如,丁基酸酷(butylate),環酷(cycloate),二-稀丙 酸酷(di-allate), EPTC,益普克(esprocarb),棋林酯( Bolinate),普硫克(prosulfocarb),硫苯克(thioben-carb)與三-稀丙酯(tri-allate);三嗪類,例如,草脫淨 (atrazine),氰曉(cyanazine),草滅淨(simazine),席 美特林(simetryn),特比特林(terbutryn)與特丁基嚷( -37- 本纸張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) (請先閲讀背面之注意事項再填寫本頁) .飞: 、τ 經濟部中央揉準局員工消費合作社印製 …* A7 B7____ 五、發明説明(36 ) terbutylazine);三曉醑類,例如,菲殺淨(hexazinone), 滅必隆(metajuitron)與滅必淨(metribuzin);其他類殺草 劑,例如,胺基三哩,苯扶斯特(benfuresate),本達隆 (bentazone),西甲基林(cinmethylin),克馬稼( * - clomazone),克比拉地(clopyralid),待坐克(difenzo-quat),二硫比(dithiopyr),依富美特(ethofumesate), 氣氯醑(f luorochloridone),固殺草(glufosinate), 赛碟塞(glyphosate),愛索本(isoxaben),畢利得( pyridate),快克草(quinchlorac),快馬雷(quinmerac), 速殺箄(sulphosate)與三地芬(tridiphane)。 本發明的這頚活性化合物另可呈被販售之配製劑及K之 配製成之使用型式、與增效劑構成混合物之型式存在。增 效劑係一種可增加活性化合物之效力但本身並不具活性之 物質〇 - 由市售配方配製之圼使用型式製劑中的活性化合物含量 .範圍掻廣。使用型式的配製劑,其中的活性化合物濃度可 介於0 · 0000001至95¾重量計,宜介於0.0001與U重量計間 〇 這類化合物可依習用的通當使用方式被應用。 當被用於處理衛生方面及儲存產品方面之有害生物時, 本活性化合物之特點為,其對木料與泥土均具有極佳的持 鱭作用,且葑经施用石灰物質之鹼性有很好的安定性。 本發明的活性化合物之製備與用途可由下述實例看出。 -38- 本紙張尺度逋用中國國家標牟(CNS ) A4規格(21〇Χ297公釐) ----------1-------訂 J------飞 (請先閲讀背面之注意事項再填寫本頁) _ 312692 at B7 經濟部中央標準局員工消费合作社印製 五、發明説明(37 ) 郸備實俐 管例1
於殺菌釜中,將溶解於20奄升無水二氣甲烷中的3克( 7.7毫莫耳)N-[嗎啉-4-基-(4-特丁基苯基)-甲基]-2,6-二氟苯並醯胺之溶液(參考實例IIa-Ι),與25毫升(25毫 冥耳)的四氯化钛(溶解於二氯甲烷之一莫耳溶液),从乾 燥的氯化氫氣體在室溫下予K飽和其後,於約下通 入乙烯经約20至30分鐘,再將此混合物於及自然產 生的约14巴壓力下携拌24小時。接著授入約1〇〇奄升的冰 -水,使用氫氧化鈉溶液,於0*0下弄成鹼性後,反覆Μ二 氯甲烷萃取。將有襪層併合,利用硫酸鎂乾燁後湄缩之。 Κ層析法將油質殘存物纯化。 可製得0.83克(理論值之32.5%)的4-(4-特丁基苯基)-2-(2,6-二氟苯基)-5,6-二氫-4Η-1,3-噁嗪。 1 H HMR (ppm in CDC13 ): 7.42-6.90 (m,7H); 4.78(m, 1H); 4.41-4.30(m, 2H, 1H); 1.31(s, 9H)。 -39- 本紙張尺度適用中國國家揉準(CNS ) A4规格(210X297公釐) (請先閱讀背面之注意事項再填寫本頁) 飞: 訂 A7 B7 五、發明说明(38 ) g俐2 C(CH3)3
經濟部中央榡準局員工消費合作·社印製 (沒將式(Π)之化合物中間物予K單離) 於50*0, 40毫升的二氯甲烷中,將3.5克(20毫冥耳)的 2-氯-6-氟苯胺,與3.4克(21毫莫耳)的4-特丁基苄醛及 2.1克(24毫冥耳)的嗎啉,一起攪拌18小時。 冷卻後,K45毫升的四氯化鈦(溶解於二氛甲烷之一冥 耳溶液)處理,並於殺菌釜中,在室溫下飽和Μ乾煉的氯 化氫氣體在室溫下予Κ飽和。其後^於約0*C下通入乙烯 經約20至30分鐘,再將此混合物於70t:及自然產生的約 14巴壓力下攪拌24小時。接著於反應混合物中攪入約150 毫升的冰·水,使用氫氧化鈉溶液,於〇*C下弄成鹼性後, 反覆Μ二氯甲烷萃取。將有機層併合,利用硫酸鎂乾燥後 濃縮之。 可製得其logP為4.71,量為1.38克(理論值之30¾)的 4- (4-特丁基苯基)-2- (2-氯-6-氟苯基)-5,6-二氫-4H-1,3 -喔曉。 依類似於實例1與實例2的一般製法,可製得具化學式 (I)之下述化合物: -40- .紙張尺度適用中國國家標準(CNS ) A4規格(210Χ297公釐) (請先閱讀背面之注意事項再填寫本頁) 飞 •訂 蔚丨伸請案第851G5iq號 8^12.18 (民國85年12月Θ曰送呈)-附件二 严7 五、發明説明(39 ) 表1
經濟部中央標隼局員工消費合作社印製 實例編號 A B 3* P 4 5 P 6 7 --CHj-S-^-ocHjCtCH^a 8 P 9 各·. p -CH2-S-^C(CH3)3 10 F -ch2-s-<^f - 11 F -CHfS^^sCH^CH^ I ^裝 訂-I ^ Γ- (請先閱讀背面之注意事項再填寫本頁) *實例編號3之NMR資料如下: e-NMIKppm 於CDCh中):7.50-6.85(m,7H) ; 4.75(m, 1H) ; 4.45-4.25(m, 2H);2.32(m, 1H) ; 1.92(m, 1H) 〇 -41- 本紙張尺度適用中國國家標率(CNS ) A4規格(210X297公釐〉 A7 B7 五、發明説明(40 ) 經濟部中央標隼局員工消費合作社印製 (表1,續) 實例編號 12 A Ο1 F B 13 α1 Ρ *-ch2-〇-〇ch3 14 Ρ 15 ρ 16 -CH2-<2)-C(CH3)3 17 -CH2-O〇CH3 18 p -CH2-〇0CF3 19 a1 f -ch2-^3 20 F -ch2-h^-cf3 21 cf c -ch2-CC〇> 22 F -ch2-CH2> 23 ¥ F F -ch2-〇och3 -42- (請先閱讀背面之注意事項再填寫本頁) 本纸張尺度適用中國國家標準(CNS〉A4規格(210X297公釐) A7 B7 五、發明説明(μ ) 41 (表1,續) 經濟部中央標準局員工消費合作社印製 編號 A B 24 F -CH2-SHg)-ci 25 α1 -ch2-s-<2)h2)-ocf3 26 d F -ch2-sh^) 27 c -CH^SH^Br 28 F 29 厂 CH(CH3)-〇-^C(CH3)3 30 4 c -CH=CH-^C(CH3)3 31 _CH2CHrC^C(CH3)3 32 F p -0-0 33 F -〇och2-〇 (請先閱讀背面之注意事項再填寫本頁) -43- 本紙張尺度適用中國國家標準(CNS ) A4規格(2丨0X297公釐) A7 B7 五、發明説明(42 表2
Λ (Ia-l) 經濟部中央標準局員工消費合作社印製
實例編號 X„ 34 2,6-F, 4-C1 35 2,6-F2 H 36 2,6-F, 4-OCH3 37 2,6-F, 4-〇-CH-(CH3)2 38 2,6-F, 4>〇-C8H】» 39 2,6-F0 2-C1 40 2,6-F, 3-C1 41 2,6-F, 2,6-Cl2 42 2,6-F2 2,4-Cl2 43 2,6-F, 2,4,5-Cl3 44 2-C1, 6-F H 45 2-C1, 6-F 4-C1 46 2-C1, 6-F 4-OCH3 47 2-C1, 6-F .4-〇-CH-(CH3)2 48 2-Cl, 6-F 4-0-C8H]7(n) 49 2-Cl, 6-F . 2-C1 50 2-C1, 6-F 3-C1 51 2-C1, 6-F 2,6-Cl2 52 2-C1, 6-F 2,4-CU 53 2-C1, 6-F 2,4,5-d3 54 2,6-F, 4-F -44- (請先閱讀背面之注意事項再填寫本頁) 4 訂-— 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 312692 A7 B7 五、發明説明(43 )(表2,續)- 實例編號 v 5556575859606162636465666768697071727374757677787980818283 經濟部中央標準局員工消費合作杜印製 2.6- F2 2.6- F2 2.6- F2 2.6- F2 2.6- F, 2.6- F2 2.6- F2 2s6-F, 2.6- F2 2.6- F2 2-C1, 6-F 2-C1, 6-F 2.6- Cl-, 2.6- Cl; 2.6- 0½ 2.6- Cl, 2.6- Cl; 2.6- Cl0 2-Cl" 2.6- F, 2.6- F, 2.6- F, 2.6- F, 2.6- F, 2.6- F2 2.6- F2 2.6- F, 2.6- F2 2.6- F, -45- 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) 2-F^Η7(η) 4-OCF, 4-CF, 2- CF, 2,4-F2 2-C1, 4-F 2-C1, 6-F 2-OEt, 5-Br 2·α, 4*〇CH(CH3>2 4-CF3 2-C1, 6-F H 4-C1 3- CJ 2-C1 4-t-butyl 4-CF, 2-C1 2-Br 3- OPh 4- 〇Ph 2-OPh 4-N(CH3)2 4-SPh
2-S •o 2.3- Cl2 3.4- Cl, 3.5- Cl2
Cl I -II I »-1- I 1-- 1!I II II 1- IJI ΙΪ-1、tT-m !-1 -SI I j—α^ (請先閲讀背面之注意事項再填寫本頁) .
A
7 B 經濟部中央標準局員工消費合作社印製 五、發明説明(44 ) (表2,續) 實例編號 Xn 84 2,6-F2 2,5-Cl2 85 2,6-F2 2,6-F2 86 2,6-F2 2-F, 4-C1 87 2,6-F2 2-C1, 4-Br 88 2,6-F2 2-Br, 4-F 89 2,6-F2 2-Br, 6-F 90 2,6-F2 2-Br, 4-C1 91 2,6-F2 2-C1, 3-F 92 2,6-F2 2-Cl, 3-Br 93 2,6-F2 2-C1, 3-CH3 94 2,6-F2 2-C1, 4-OEt 95 2,6-F2 2-C1, 4-CH3 96 2,6-F2 2-C1, 3-OPh 97 2,6-F2 2-C1, 3-t-butyl 98 2,6-F2 2-F, 3-C1 99 2,6-F2 2-Br, 3-C1 100 2,6-F2 3-Br, 4-C1 101 2,6-F2 2-C1, 4-CF3 102 2,6-F2 為 2-C1, 4-t-butyl 103 2,6-F2 2-Cl, 4-OCH2CF3 104 2,6-F, 2-Br, 4-OEt 105 2,6-F2 2-F, 4-t-butyl 106 2,6-F2 2,4-(CH3)2 107 2,6-F2 2,3-(CH3)2 108 2,6-F2 3-Br, 4-OEt 109 2,6-F2 2-OEt, 4-C1 110 2,6-F2 2-OEt, 4-t-butyl 111 · 2,6-F2 2-OEt, 5-C1 112 2,6-F2 2-OEt, 5-Br 113 2,6-F2 2-OCH2-C2H5, 5-Br -46- (請先閲讀背面之注意事項再填寫本-!) ‘衣- 訂- 本紙張尺度適用中國國家標準(CNS ) A4規格(210Χ297公釐) 五、發明説明(45 ) (表2,續) A7 B7 貝緬辄 Ym Xn 114 2,6-F2 3,4-(〇Et)2 115 2,6-F2 3-OEt, 4-t-butyl 116 2,6-F2 3-t-butyl, 4-〇Et 117 2,6-F2 3-t-butyl, 4-O-n-Pr. 118 2,6-F2 Cl 4-七Cf% 119 2,6-F2 4-Ph 120 2,6-F2 4-OCH2Ph 121 2,6-F2 2,3-Cl2, 4-SCH3 122 2,6-F2 2,3-Cl2, 4-OEt 123 2,6-F2 2,3,4-Cl3 124 2,6-F2 2-OEt, 4,5-Cl2 125 2,6-F2 2-O-n-Pen., 4,5-Cl2 126 2,6-F2 2,4»C12, 5-Br 127 2,6-F2 2-OCH3, 4-C1, 5-Br 128 2,6-F2 2-OEt, 4-C1, 5-Br 129 2,6-F2 2-O-n-Pen., 4-C1, 5-Br 130 2,6*F2 2,5-(OCH^)2,4-t-butyI 131 2,6-F2 λ 2,5-Cl2, 4-OEt 132 2,6-F2 2,3,4,5,6-F5 133 2-C1, 6-F 2,3-Cl, 134 2-C1, 6-F 2,6-F2 135 2-C1, 6-F 4-Br 136 2-C1, 6-F 2,3,4-Cl2 137 2-C1, 6-F 2-OEt, 3,4-Cl2 138 2-C1, 6-F. 2-O-n Pen., 4,5-Cl2 139 2-C1, 6-F 2-OEt, 4-C1, 5-Br 140 2-C1, 6-F 2-O-n Pen., 4-C1, 5-Br I. ml - - : - - ...... '泰- - - - --J1 —^1,一ej-II i—I - - - 1 —II (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作杜印製 -47- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) A7 312692 B7 五、發明説明(46 ) (表2,續) .頁例漏鰥 Υ» x„ 141 2,6-Cl2 .ch3 4-〇< 3 142 2,6-Cl2 ch3 143 4-〇CgH】7⑻ 2,6-Cl2 2,3-Cl2 144 2,6-Cl2 2,4-Cl2 145 2,6-Cl2 2-0-nPr., 4-C1, 5-Br • 146 2-C1 4-C1 147 2-F 4-C1 148 2-CF3 4-C1 149 2-C02CH3 4-C1 — .— — — I— ^ ^ I —I—7-—訂- 1111^-^ (請先閎讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 -48- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(47 表
(la-2) 經濟部中央標準局員工消費合作社印製 實例編號 R* Rb (R% 150 Η F H 151 Η Cl H 152 F F H 153 Cl F H 154 Cl Cl H 155 H Cl 2-F 156 F F 2-F 157 Cl F Λ 2-F 158 F F 3-F 159 Cl F 3-F 160 H Cl 4-F 161 F F . 4-F 162 Cl F 4-F 163 F F 2-F, 4-F 164 Cl F 2-F, 4-F 165 F F 2-F, 4-C1 166 F F 2-F, 4-(CH2)4CH3 167 F F 2-F, 4-(CH2)5CH3 168 F F 2-F, 4-(CH2)6CH3 169 F F 2-F, 4-(CH2)7CH3 170 Cl F 2-F, 4-(CH2)7CH3 -49- (請先閲讀背面之注意事項再填寫本頁)
本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明(48 ) (表3,續) 實例編號 Ra Rb (Rc)q 171 Cl F 2-F, 4-OCH2CH3 172 F F 2-F, 4-0(CH2)3CH3 173 F F 2-f· 4-〇 174 F F 2-F, 4— 175 F F 2-F, 4— 176 Cl F 2-F, 4·—T_\-CH2CH3 177 F F 2-F, 4—^^-C^CHjCHa 178 F F 2'F· 4H^-CH(CH3)2 179 F F .2-F. 4-^Zy〇CF3 180 Cl F OCH2CH3 2.F. 181 F F 〇^CH3 2-F, 4-^-C(CH3)3 182 F F . 2-F, 5-F 183 F F 2-F, 5-C1 184 F F 2-F, 6-F 185 F F 3-F, 4-F 186 F F 3-F, 4-C1 187 Cl F 3-F, 4-C1 189 F F 3-F, 4-(CH2)5CH3 190 F F 3-F, 4-OCH3 191 Cl F 3-F, 4-0 -50 - (請先閱讀背面之注意事項再填寫本頁) .衣· 訂 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(49(表3,續) i例編號 R*
Rb 經濟部中央標準局員工消費合作社印製 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220
F F Cl H F Cl F Cl H F Cl Cl F Cl F H F Cl F F F F F F Cl F F F F
F F Cl F F F F F Cl F F Cl F F F Cl F F F F F F F F F F F F F 3-F, 4—If ')~CH,CH, ::3-F, 5-F 3-F, 5-F 2-C1 2-C1 2- C1 3- C1 3- C1 4- C1 4-C1 4-C1 4-C1· 2-C1, 3-C1 2-C1, 3-C1 2-C1, 4-F 2-C1, 4-C1 2-C1, 4-C1 2-C1, 4-C1 2-C1, 4-CH3 2-C1, 4-CH2CH3 2-C1, 4-CH2CH2CH3 2-C1, 4-(CH2)3CH3 2-C1, 4-CH2CH (CH3)2 2-C1, 4-C (CH3)3 2-C1, 4-C (CH3)3 2-C1, 4-(CH2)4CH3 2-C1, 4-(CH2)5CH3 2-C1, 4-(CH2)6CH3 2-C1, 4-(CH2)7CH3 ----------I农------訂----^----一冰 (請先閱讀背面之注意事項再填寫本頁) -51· 本紙張尺度適用中國國家標準(CNS > A4規格(2+10X297公釐) 五、發明説明(5〇 ) A7 B7 經濟部中央標準局員工消費合作社印製 (表3,續) 實例編號 R* Rb (Rc)q 221 C1 F 2-Cl, 4-(CH2)7CH3 222 F F 2-C1, 4-(CH2)9CH3 223 F F 2-C1,4^Η2)„(:Η3 224 F F 2-C1, 4-OCH2CH2CH3 225 C1 F 2-C1, 4-OCH2CH2CH3 226 F F 2-C1, 4-0(CH2)4CH3 227 F F 2-C1, 4-0(CH2)8CH3 228 F F 2-CI, 4-0 229 F F 2-CI, 4— 230 F F 2-CI, 4—<2>~CI 231 F F 2-CI, 4—^^-CH2CH2CH3 232 C1 F 2-CI, 4—^^-CH2CH2CH3 233 F F 2-CI, 4—^^-CH(CH3)2 234 F F 2-CI, 4-<^-C(CH3)3 235 F F . 2-d, 4-^>-(CH2)7CH3 236 F F 2-CI, 4—^^-〇cF3 237 - ··, F F 2-CI, 5-C1 238 F F 2-CI, 5-CF3 239 F F 3-C1, 4-F 240 C1 F 3-C1, 4-F 241 Η Cl 3-C1, 4-C1 242 F F 3-C1, 4-C1 243 F F 3-C1, 4-CH3 _52~ 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) ---------{裝-----—訂.—^----ί 線 (請先閱讀背面之注意事項再填寫本頁) 31S692 A7 B7 五、發明説明(SI ) (表3,續) 經濟部中央標隼局員工消費合作社印製 實例編號 R* Rb 244 F F 3-Cl, 4-CH2CH2CH3 245 F F 3-C1, 4-{CH2)5CH3 246 F F 3-Cl, 4-OCH2CH3 247 F F 3-a, 4— 248 F F 3-CI, 4—^^-CH2CH2CH3 249 C1 F 3-CI, 4—^^-CH2CH2CH3 250 C1 F 3-CI, 4-0-(^-01 251 F F 3-Cl, 5-C1 252 Η F 2-Br 253 F F 4-Br 254 Cl F 4-Br 255 F F 2-CH3 256 Η Cl · 3-CH3 257 F F 3-CH3 258 F F 4-¾ 259 F F 2-CH3, 4-F 260 F F . 2-CH3) 4-C1 261 Cl Cl 2-CH3> 4-C1 262 F F 2-CH3, 4-(CH2)7CH3 263 F F 2-CH3, 4-OCH2CH2CH3 264 Cl F 2-CH3, 4-OCH2CH2CH3 265 F F 2-CH3, 4— 266 F F 2-CH3, 4-<2>-CH2CH3 267 F F 2-CH3. 4-<^>-C(CH3)3 -53- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) ------.---.{裝------—1T-------4 線 (請先聞讀背面之注意事項再填寫本頁) 五、發明説明(52 ) A7 B7 經濟部中央標準局員工消費合作社印製 (表3,續) 實例編號 Ra Rb (Rc)q 268 F F 2-CH3. 4—^^>-〇cf3 269 CI F 2-CH3, 4—^^-0CF3 270 F F 2-CH3,4-〇-^^-ci 271 F F 2-CH3,4-〇-^)-(cH2)5CH3 272 F F 2-CH3,4-〇-^^-cF3 273 Cl ^ F 2-CH3,4-〇-^^_CF3 274 F F 2-CH3, 5-CH3 275 F F 2-CH3, 5-CH(CH3)2 276 Cl Cl 2-CH3, 5-C(CH3)3 277 F F 3-CH3,4-CH3 278 F F 3-CH3,Cl 279 Cl F 3-CH3,4一〇-^)-CH3 280 F F 3-ch3, 4 - 〇ch2-^~^- ch2ch3 281 F F 2-CH2CH3 282 F F 3-CH2CH3 283 F F 4-CH2CH3 284 F F 2-CH2CH3,4— -54- ---------一 裝-----^——訂.-------{線 (請先閲讀背面之注意事項再填寫本頁) 本紙張又度適用中國國家標準(CNS ) A4規格(210 X 297公釐) 五、發明説明(53 ) (表3,續) Μ Β7 經濟部中央標準局員工消費合作社印製 實例編號 R* Rb (Rc)q 285 F F 2-CH2CH3,CH2CH3 286 F F 2-CH2CH3,4_^HCH2)3CH3 287 F F 2-CH2CH3,0CF3 288 C1 F Cl 2-CH2CH3,4— 289 F F 2-CH2CH3,Cl 290 F F 2-ΟΗ2〇Ηβ14一0·^ OCF3 291 F F 2-CH2CH3, 5-C1 292 F F 2-CH2CH2CH3 293 F F 3-CH2CH2CH3 294 F F 4-CH2CH2CH3 295 C1 F 4-CH2CH2CH3 296 F F 2-CH2CH2CH3, 4-C1 297 F F 3-CH(CH3)2 298 F F 4-CH(CH3)2 299 C1 F 4-CH(CH3)2 300 F F 3-(CH2)3CH3 301 F F 4-(CH2)3CH3 -55_ ---------< 裝-----'--訂,--I-----{線 (請先閱讀背面之注意事項再填寫本頁). 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 312692 A7 B7 五、發明説明(54 ) (表3,續) 實例編號 R* Rb (Rc)q 302 F F 3-CH2CH(CH3)2 303 F F 4-CH2CH(CH3)2 304 F F 4-CH(CH3)CH2CH2 305 Η Cl 3-C(CH3)3 306 F F 3-C(CH3)3 307 Η F 4-C(CH3)3 308 Cl F 4~C(CH3)3 309 Cl Cl 4-C(CH3)3 310 F F 3-(CH2)4CH3 311 F F 4-(CH2)4CH3 312 F F 3-(CH2)2CH(CH3)2 313 F F Hcn^CHiCH^ 314 F F 3-C(CH3)2CH2CH3 315 F F 4-C(CH3)2CH2CH3 316 F F 3-CH2C(CH3)3 317 F F .4-CH2C(CH3)3 318 F F 3-(CH2)5CH3 319 Cl F 3-(CH2)5CH3 320 F F . 4-(CH2)5CH3 321 F F 3-(CH2)3CH(CH3)2 322 F F 4-(CH2)3CH(CH3)2 323 F F 3-(CH2)6CH3 324 Cl F 3-(CH2)6CH3 325 F F 4-(CH2)6CH3 -56- (請先閱讀背面之注意事項再填寫本頁) 裝, Ψ 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 五、發明説明(55 ) (表3,續) A7 B7 經濟部中央標準局員工消費合作社印製 實例編號 R* Rb (R\ 326 F F 3-(CH2)7CH3 327 F F 4-(CH2)7CH3 328 F F 3-(CH2)8CH3 329 C1 Cl 3-(CH2)8CH3 330 F F 4-(CH2)8CH3 331 F F 3-(CH2)9CH3 332 F F 3-(CH2)10CH3 333 F F 334 F F 4-(CH2)14CH3 335 F F 3-OCH3 336 C1 F 3-OCH3 337 F F 4-OCH3 338 F F 2-OCH3, 4-C(CH3)3 339 F F 2-OCH3, 4-(CH2)7CH3 340 F F 2-OCH3, 4-(CH2)8CH3 341 F F 2-OCH3, 4-CF3 342 F F 2-OCH3,4—^^-ci 343 F F 2-OCH3,4—CH2CH2CH3 344 F F 4-(CH2)9CH3 345 C1 F 2-OCH3,4—CH2CH2CH3 346 F F 2-OCH3.4—<^- CH(CH3)2 347 F F 2-OCH3,4—(^-〇(CH3)3 348 F F 2-OCH3,4-^)-〇CF3 本紙張尺度適用中國國家標準(CNS )八4規格(釐) (請先閱讀背面之注意事項再填寫本頁) 餐· 訂- 五、發明説明(56 ) A7 B7 經濟部中央標準局員工消費合作社印製 (表3,續) 實例編號 Ra Rh (Rc)q 349 F F 2-OCH3, 5-Cl 350 F F 2-OCH3, 5-C(CH3)3 351 F F 2-OCH3> 5~(CH2)6CH3 352 F F 2-OCH2CH3 353 Cl F 2-OCH2CH3 354 F F 3-OCH2CH3 355 F F 4-00¾¾ 356 F F 2-OCH2CH3j 4-F 357 H Cl 2-OCH2CH3j 4-C1 358 F « F 2-OCH2CH3, 4-C1 359 F F 2-OCH2CH3, 4-CH3, 360 F F 2-OCH2CH3, 4-CH(CH3)2 361 F F 2-OCH2CH3, 4-C(CH3)3 362 F F 2-OCH2CH3, 4-Si(CH3)3 363 Cl F 2-OCH2CH3, 4-Si(CH3)3 364 F F 2-OCH2CH3, 4—ci 365 F F 2-OCH2CH3, 4—<^-cH2CH2CH3 366 Cl F 2-OCH2CH3, 4~^^-CHjCH2CH3 367 F F 2-OCH2CH3. 4—<^-C(CH3)3 368 F F 2-OCH2CH3, 4—<2^〇CF3 369 Cl F 2-OCH2CH3, 4—<Q^〇CF3 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) (請先閱讀背面之注意事項再填寫本頁) 裝· 線 312692 A7 B7 五、發明説明.(57 ) (表3,續) 經濟部中央標準局員工消費合作社印製 實例編號 R* Rb (Rc)q 370 F F 2-OCH2CH3, 4-0〇CF3 371 F F 2-OCH2CH3, 5-C1 372 F F 2-OCH2CH3, 5-Br 373 F F 2-OCH2CH3, 5-C(CH3>3 374 F F 3-OCH2CH2CH3 375 F F 4-OCH2CH2CH3 376 F F 2-OCH2CH2CH3, 4-F 377 C1 F 2-OCH2CH2CH3, 4-F 378 F F 2-OCH2CH2CH3, 4-C1 379 F F 2-OCH2CH2CH3, 4-CH3 380 F F 2-OCH2CH2CH3, 4-CH(CH3)2 381 F F 2-OCH2CH2CH3, 5-(CH2)6CH3 382 F F 3-OCH(CH3)2 383 F F 4-OCH(CH3)2 384 C1 F 4-OCH(CH3)2 385 F F 4-OCH2CH(CH3)2 386 F F 4-0CH(CH3)CH2CH3 387 F F 3-0(CH2)4CH3 388 F F 4-0(CH2)4CH3 389 F F 4-0(CH2)2CH(CH3)2 390 F F 3-0(CH2)5CH3 391 F F 4-0(CH2)5CH3 392 C1 F 4-0(CH2)5CH3 393 F F 3-0(CH2)6CH3 394 F F 4-0(CH2)6CH3 395 F F 3-0(CH2)7CH3 396 F F 4-0(CH2)7CH3 397 C1 F 4-0(CH2)7CH3 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) (請先閱讀背面之注意事項再填寫本頁) 袈· 、-°- 經濟部中央標準局員工消費合作社印製 312692 A7 B7 五、發明説明(58 ) (表3,續) 實例編號 R* Rb (Rc)q 398 F F 4-0(CH2)8CH3 399 F F 4-0(CH2)9CH3 400 F F 4-O(CH2)10CH3 401 F F 4-0(CH2)uCH3 402 F F 3-0(CH2)14CH3 403 F F 4-SCH3 404 F F 4-SCH(CH3)2 405 F F 4-S(CH2)8CH3 406 F F 2-CF3 407 F <#· F 3-CF3 408 C1 F 3-CF3 409 F F 4-CF3 410 F F 3-OCF3 411 F F 4-OCF3 412 F F 3-OCH2CF3 413 C1 F 4-OCH2CF3 414 F F 3-Si(CH3)3 415 F F 4-Si(CH3)3 416 C1 F · 4-Si(CH3)3 417 F F 4-Si(CH2CH3)3 418 C1 F 4-Si(CH2CH3)3 419 F F 4-Si[C(CH3)3, (CH3)2] 420 F F 4HS> 421 C1 F 422 F F 4-<^)-C(CH3)3 -60· ---------<裝-----^——訂_-----」線 (請先聞讀背面之注意事項再填寫本頁) 本纸張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明L ) (表3,續) 經濟部中央標準局員工消費合作社印製 實例_號 R* Rb (Rc)q 423 C1 F ㈣3 424 F F 425 F F \=/ 4-0 426 C1 F 427 F F CIv 4-b 428 F / F Ci 429 F F 4-^^-Cl 430 F F 4-<^-〇H2CH3 431 F F .4-(^>-(CH2)3CH3 432 F F 4CH(CH3)CH2CH3 433 F F 4-<^-C(CH3)3 434 F F 4-O^-(ch2)4ch3 435 F F 4~O^OCH3 436 F F 4-^]^- OCH2CH2CH3 437 F F 4-^)*〇CH(CH3)2 本纸張尺度適用中國國家標準(CNS ) A4規格(2I0X 29*7公釐) -61" (請先閱讀背面之注意事項再填寫本頁) 訂 A7 B7 五、發明説明) 經濟部中央標準局員工消費合作社印製 (表3,續) 實例編號 R* Rb (R% 438 F F 4-〇-CF3 439 F Cl 4-〇-〇CF3 440 F F 4O"〇CF3 441 F F 442 C1 F 443 F F / 4 OCH2CH2CH3 444 F F Cl C! 445 Η Cl C! 4_C^ci 446 F F Cl N—— - / Cl 447 F F Cl 4-〇-ch3 448 F F Cl 4-0>-〇cf3 449 F F Cl Cl 一62_ (請先閲讀背面之注意事項再填寫本頁) 訂' 本紙張尺度適用中國國家標準(CNS〉A4規格(210X:297公釐) 31U92 A7 B7 五、發明説明(61 ) (表3,續) 經濟部中央標準局員工消費合作社印製 編號實例 R» Rb (R% 450 F F Br 4—^~^-OCF3 451 F F ch3 452 F F ch3 4-^^CH3 453 F F CH3 454 F "F OCH3 4~^3~C(CH3)3 455 F F och2ch3 456 F F ch3 4-^-CH3 ch3 457 F F . 4-Q F F 458 C1 F FWF 4-Q F F 459 C1 F 3-^^) ,4-0(CH2)3CH3 460 F F 4—CH2-<^^ -63- (請先閲讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 312B92 A7 B7 五、發明説明ς2 ) (表3,縉) 實例編號 Ra Rb (Rc)q 461 F F 4—CH 心 F 462 Cl F 463 F F Ci 4-CH2-(3 464 F F 4~CH2-^^-ci 465 F F 4~CH2~^r^CH2CH3 466 F F 4-CH2-^3^CH2CH2CH3 467 F F 4*~CH2-<^>-CH(CH3)2 468 F F 4_CH2-0"(CH2)3CH3 469 Cl F 4-CH2-^-(CH2)3CH3 470 F F 4 一 CH2~<^C(CH3)3 471 F F 4~CH2-<2>~(CH2)sCH3 472 F F ^ch2-^-(ch2)7ch3 473 F F —CH2~^3~〇CH3 474 F F 4~CH2~^3~〇CF3 -64- (請先閲讀背面之注意事項再填寫本頁) 衣- -訂- 本紙張尺度適用中國國家標準(CNS > A4規格(210X297公釐)
A B 經濟部中央標準局員工消費合作社印製 五、發明説明“) (表3,續)
(請先閲讀背面之注意事項再填寫本頁) 衣. 訂-- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(64 ) 經濟部中央標準局員工消費合作社印製 (表3,續) 實例編號 R» Rb (Rc)q 488 C1 F 4-CH2CH2CH2-<f3-CI 489 F F 4~OCH2— 490 F F Cl \ 4-〇CH2-T^ 491 F F 4-OCH2-^^-CH(CH3)3 492 F F 4-OCH2-^^- CH(CH3)3 493 F F F \ 4-OCH2-T^ F 494 F F 3-°-〇 495 C1 F 3-°-〇 496 F F 4—〇— 497 F F . 4-〇-^3^-CI 498 F F 4 - 499 F F 4 - 〇~0"CH3 500 F F 4~°~<2^CH2CH2CH3 -66_ (請先閱讀背面之注意事項再填寫本頁)
本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(65) 經濟部中央標準局員工消費合作社印裝 (表3,續) 實例編號 R* Rb (Rc)q 501 F F 4_〇~^^CH(CH3>CH2CH3 502 F F 4~°O~(CH^CH3 503 F F 4 一 0_^^〇CH3 504 F F cf3 4-°-〇 505 C1 F cf3 506 4-°~C5 F F 4 - 〇-〇^cf3 507 C1 F 4~〇H〇-〇CF3 508 F F C! 4-°-^CFz 519 C1 F Cl 4~〇~^CF3 510 F F Cl 4-°-0 511 F F Cl ^CH3 4-〇H^>〇(CH2)7CH3 CH, 512 F F 4-CH(CH3)-<2>-CH2CH3 -67- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明) (表3,續) 經濟部中央標準局員工消費合作社印製 實例編號 R· Rb (Rc)q 513 F F F 4-CH(CH3)F 514 C1 F F 4-CH(CH3)-^^F 515 F F F 4-CH(CH3) ch2ch2ch3 516 F F Cl 4-CH(CH3) ch2ch2ch3 517 F F 4-CH(CH2CH3)*^)-(CH2)7CH3 518 F F 4- CH[CH2CH(CH3)2] Cl 519 F F 4 - C(CH3)2-^^· 〇CH2CH3 520 F F 4-CH(CH3)CHr<2>-CH2CH3 521 F F -Si(CH3)2-<^) 522 C1 F 4-Si(CH3)2-<^3 523 F F 2-C1, 3-C1, 4-(CH2)4CH3 524 C1 F 2-C1, 4-CH3, 5-Br 525 F F 3-C1, 4-OCH2CH3, 5-C1 -68- (#先閲讀背面之注意事項再填寫本頁)
本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 五、發明説明(g7 ) (表3,續) A7 B7 經濟部中央梂準局員工消費合作社印製 實例編號 R* Rb (Rc)q 526 C1 Cl 3-Cl, 4-OCH2CH3, 5-C1 527 C1 F 2-OCH2CF3j 4-C1, 5-C1 528 F F 2-OCH2CH3, 4-C1, 5-Br 539 F F 2-OCH2CH2CH3, 4-C1, 5-Br 530 F F 2-OCH2CH2CH3, 4-C1, 5-CH2CH3 531 C1 F 2-OCH2CH2CH3, 4-C1, 5-CH2CH3 532 C1 F 3-CH2CH3, 4-C1, 5-CH2CH3 533 F .F 2-OCH3, 4-CH3, 5-C1 534 F F 2-OCH2CH3, 3-CH3, 5-C1 535 F F 2-CH3, 4-CH3, 5-CH3 536 F F 3-CH3, 4-OCH(CH3)2, 5-CH3 537 F F 3-CH3, 4-〇(CH2)2CH(CH3)2, 5-CH3 538 C1 F 3-CH3j 4-〇(CH2)2CH(CH3)2, 5-CH3 539 F F 2-OCH3, 3-C(CH3)3, 5-CH3 540 F. F 2-CH3, 3-CH3> 4-CH3, 5-CH3 541 F F 2-OCH3, 3-CH(CH3)2, 5-CH2CH3 542 C1 F 3-C(CH3)3, 4.OCH3, 5-C(CH3)3 543 F F 2-F, 4-(CH2)6CH3, 6-F 544 F F 2-C1, 3-F, 5-F 本紙張尺度適用中國國家標準(CNS ) A4規格(210'i?97公釐) (請先閱讀背面之注意事項再填寫本頁) 312682 A7 B7 、發明説明(68 ) ,續) 列編號 R* Rb (Rc)q 545 C1 F 2-C1, 3-F, 5-F 546 Η F 2-OCH2CH2CH3, 4-F, 5-F 547 F F 2-OCH2CH2CH3, 4-F, 5-F 548 Cl F 2-OCH2CH2CH3, 4-F, 5-Br, '6-F 549 F F 2-F, 3-F, 4-0(CH2)3CH3, 5-F, 6-F 5S0. F F 2-OGH2CH3,3-C(CH3)3 551 F F 3-〇 552 Cl F 553 F F 2-OCH2CH2CH3, 3-C1 554 Cl F 2-OCH2CH2CH3, 3-C1 (請先閲讀背面之注$項再填寫本頁) ¾. 寶例編號555 經濟部中央梯準局員工消費合作社印裝
och2ch2ci B.p.: 210°C/0.1 mm 下面爲表中所用縮寫字之含義: Me =甲基 έΐ =乙基 Pr =丙基 Bu = 丁基 Pen =戊基 Ph =苯基 -70- 本紙張尺度適用中國國家標隼(cns >A4規格(2丨0x297公釐) A7 B7 五、發明説明^ 表4
D
(lb)
經濟部中央標準局員工消費合作社印製 V 賁例編號. A D 物理常數 Ib-1 F ) Ib-2 F —^^-cooch3 '' ' Ib-3 F —<^~CHO / Ib-4 -~〇-〇h 1HNMR (ppm in DMSO) 9.30 (br, OH) 4.66 (dd, CH) Ib-5 F OH -d 1HNMR (ppm in DMSO) 9.44 (br, OH) 4.68 (dd, CH) -71- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) (請先閲讀背面之注意事項再填寫本頁) ;今 訂-:
____Ab 五、發明説明(7Q ) 雔備忒(TTa)之起始材料 g俐(TTa-1) Γ~\ CO-NH-CH-N Ο N~1 (Da-1) C(CH3)3 將13.6克(84奄莫耳)之4-特丁基T醛與8.5克(97.7¾莫 耳)的嗎琳加入至溶解於100牽升無水甲酵之12.8克(81.5 毫莫耳)之2,6-二氟苯醢胺溶液中,在約40至50Ό的溫度 下將反應混合物授拌24小時。接著與約100奄升的冰-水混 合攪拌,吸引漶下沈澱,K水洗遇後乾煉之。 可得21克(理綸值之67%)之K-[嗎啉-4^基r44-特丁基苯 基卜甲基]-2,6·二氟苯釀胺,溶點命199-200t:。 --------1 4 '^— — 1 —-—訂 (請先閲讀背面之注意事項再壤寫本頁) 經濟部-6-夬榡率局貝工消費合作枉印裂 本紙張尺度適用中國國家標準(CNS) A4規格(210x297公釐)
V 312692 A7 五、發明説明) g例 HTa-2)
將3.5克(20毫莫耳)之2-氛-6-氟苯醢胺,在50*C下與溶 )
解在30毫升甲酵中的3.4克(21奄莫耳)之4-特丁基苄醛及 2.1克(24.1毫萁耳)的嗎啉一起攪拌18小時。冷卻後,令 反應混合物與100毫升的冰-水混合授拌,吸引漶下沈澱》 Μ水洗逯後乾煉之。 V 可得6.3克(理論值之77.4¾)之N-[嗎啉-4-基-(4-特丁 基苯基)-甲基]-2-氯-6-氟-苯醢胺,熔點為180-181tl。 下逑的式(Ila)之起始化合物,係依類似於實例(IIa-1) 與(IIa-2)的製法通則製取者。 ---------/ ,衣-----r—^.^------iί/Ν (請先閲讀背面之注項再填寫本頁) 經濟部中夬椟準局貝工消費合作·社印裂 73 本紙張尺度適用中國國家榡準(CNS ) A4規格(210X297公釐) 31^692 A7 B7 五、發明説明Q )
表A B2 , I R1 A-CO-NH-CH-N〆 (na) 、R2 經濟部中央標準局員工消費合作杜印製
訂、 (請先閲讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準(CNS ) A4規格(210Χ297公釐) \ 31Z&92 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明石 ) 表A(續)
-----^----ί 裝-----:--.^1-I „---4 鉍 (請先閲讀背面之注意事項再填寫本頁) 本纸張尺度適用中國國家標準(CNS ) Α4規格(210Χ297公釐) 經濟部中央標準局員工消費合作社印製 3|?β92 Α? Β7 五、發明説明(74 ) 表Α(續)
-76- --------,ί 裝----!ΐτ-ί — ^---」沐 (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ297公釐) ^8692 Λ7 Β7 五、發明説明(75 ) 用途實例 實例 小菜蛾試驗 溶劑:7份重的二甲基甲醢胺 乳化劑:1份重的烷基芳基聚甘醇醚 為製備適當的活性化合物配製劑,令一份重的活性化合 物與所述量的溶劑及所述量的乳化劑混合,K水將此濃縮 物稀釋至所要湄度。 將甘藍菜葉(Brassica cTleracea)浸滴上所要濃度的活 性化合物配製劑,趁葉子仍潤濕的狀態下感染上(小)菜蛾 (Plutella maculipennis)之幼蟲0 經一特定時間後,測定毀損的百分比。100¾表示所有的 幼蟲均巳被殺死;0¾代表幼蟲沒被殺死。 於此試驗中,經七天後之结果,例如,在0.1%的活性化 合物濃度下,實例IIa-5的化合物配製劑,可達到1005K的 摧毀度。 ---------,Γ 裝------訂------4 線 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 本紙張尺度適用中國國家榡準(CNS ) Α4規格(210X297公釐)
Claims (1)
- 公3移6維申請專利範圍 A8 B8 C8 嗽12. 18 專利申請案第85105110號 ROC Patent Appln. No.85105110 修正之申請專利範圍中文本一附件一 Amended Claims in Chinese — Enel. I ~~(民國85年12月M日送呈)~~ (Submitted on December , 1996) 1.一種製備具式(I)之化合物的方法 B N- 人 (I) 式中 A代表經鹵素取代的苯基,且 B代表苯基,其可選擇地經匕-匕-烷基、鹵素、羥 基或G -G -鹵代烷氧基取代, 特點爲,令具式(II)之醯胺衍生物與乙烯 B , | p1 A-CO-NH-CH-N^ 、R2 (Π) 装 I,tr- 一 Γ 汉 (請先聞讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 式中 Α與Β的含義同前且 R1與R2為相同或相異基且各代表烷基,或與它柄所 連结的Η原子一起代表選擇地经取代的雜環 -78- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公嫠)在氯化氫氣體與催化劑存在下,若適當,在稀釋劑 中反應。2.具式(Ila)的化合物 I A-CO-NH-CH- R2 (Ha) (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印裝 式中 A, R1與R2的定義相同於申請專利範圍第1項所給定 我且 B2的定義同申請專利範圍第1項中所给B之定義。 -79-本纸張尺度適用中國國家標準(CNS ) A4規格(210X297公釐)
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DE19518681A DE19518681A1 (de) | 1995-05-22 | 1995-05-22 | Verfahren zur Herstellung von 5,6-Dihydro-1,3-oxazinen |
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JP (1) | JPH11505261A (zh) |
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CN (1) | CN1071322C (zh) |
AU (1) | AU5764096A (zh) |
BR (1) | BR9609218A (zh) |
DE (2) | DE19518681A1 (zh) |
ES (1) | ES2229266T3 (zh) |
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MX2013015058A (es) | 2011-06-24 | 2014-01-20 | Amgen Inc | Antagonistas de melastatina 8 de potencial receptor transitorio y su uso en tratamientos. |
CN103906733A (zh) | 2011-06-24 | 2014-07-02 | 安姆根有限公司 | Trpm8拮抗剂及其在治疗中的用途 |
US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
WO2014207601A1 (en) | 2013-06-27 | 2014-12-31 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
CN112789278A (zh) * | 2018-10-06 | 2021-05-11 | 先正达参股股份有限公司 | 杀微生物的喹啉二氢-(噻嗪)噁嗪衍生物 |
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DE1545671A1 (de) * | 1965-05-05 | 1969-08-07 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 4H-5,6-Dihydro-1,3-oxazinen |
DE1670475A1 (de) * | 1967-09-29 | 1971-01-28 | Huels Chemische Werke Ag | Verfahren zur Herstellung von in 4-Stellung substituierten 4H-5,6-Dihydro-1,3-oxazinen |
DE2049160C3 (de) * | 1970-10-07 | 1980-01-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 4,4-Dimethyl-5,6-dihydro-13-oxazinen |
DE3914155A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kgaa | Verfahren zur herstellung von 5,6-dihydro-4h-1,3-oxazinen |
DE4214746A1 (de) * | 1992-05-04 | 1993-11-11 | Henkel Kgaa | Verfahren zur Herstellung von substituierten Oxzolinen und/oder Oxazinen |
AU673881B2 (en) * | 1992-12-25 | 1996-11-28 | Nippon Soda Co., Ltd. | Heterocyclic derivative and pest control agent |
US5538967A (en) * | 1995-01-18 | 1996-07-23 | E. I. Du Pont De Nemours And Company | Arthropodicidal oxazines and thiazines |
-
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1996
- 1996-04-30 TW TW085105110A patent/TW312692B/zh active
- 1996-05-09 DE DE59611076T patent/DE59611076D1/de not_active Expired - Fee Related
- 1996-05-09 US US08/930,051 patent/US5892030A/en not_active Expired - Fee Related
- 1996-05-09 KR KR1019970708209A patent/KR100420159B1/ko not_active IP Right Cessation
- 1996-05-09 CN CN96195705A patent/CN1071322C/zh not_active Expired - Fee Related
- 1996-05-09 JP JP8535306A patent/JPH11505261A/ja active Pending
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KR19990014864A (ko) | 1999-02-25 |
DE19518681A1 (de) | 1996-11-28 |
EP0827499A1 (de) | 1998-03-11 |
DE59611076D1 (de) | 2004-10-07 |
BR9609218A (pt) | 1999-02-17 |
EP0827499B1 (de) | 2004-09-01 |
HUP9801229A2 (hu) | 1998-09-28 |
ES2229266T3 (es) | 2005-04-16 |
US5892030A (en) | 1999-04-06 |
CN1191532A (zh) | 1998-08-26 |
KR100420159B1 (ko) | 2004-05-31 |
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