JP3498372B2 - Semicarbazone compound - Google Patents
Semicarbazone compoundInfo
- Publication number
- JP3498372B2 JP3498372B2 JP15499194A JP15499194A JP3498372B2 JP 3498372 B2 JP3498372 B2 JP 3498372B2 JP 15499194 A JP15499194 A JP 15499194A JP 15499194 A JP15499194 A JP 15499194A JP 3498372 B2 JP3498372 B2 JP 3498372B2
- Authority
- JP
- Japan
- Prior art keywords
- hhhho
- group
- ocf
- ochf
- oso
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 Semicarbazone compound Chemical class 0.000 title claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 99
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
- 230000000749 insecticidal effect Effects 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 3
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 820
- 239000000460 chlorine Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 26
- 239000000126 substance Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000000034 method Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- 241000607479 Yersinia pestis Species 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000012442 inert solvent Substances 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 241000221785 Erysiphales Species 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 206010039509 Scab Diseases 0.000 description 9
- 230000009969 flowable effect Effects 0.000 description 9
- 241000238876 Acari Species 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 206010027146 Melanoderma Diseases 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 241000251468 Actinopterygii Species 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 231100000989 no adverse effect Toxicity 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
- 229910000105 potassium hydride Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000213004 Alternaria solani Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 239000001692 EU approved anti-caking agent Substances 0.000 description 2
- 241000125117 Elsinoe Species 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000131448 Mycosphaerella Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241000985245 Spodoptera litura Species 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- MIJZKZQWQXKSPA-UHFFFAOYSA-N n-phenacylbenzamide Chemical compound C=1C=CC=CC=1C(=O)CNC(=O)C1=CC=CC=C1 MIJZKZQWQXKSPA-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- LGPKFIGMLPDYEA-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(N=C=O)C=C1 LGPKFIGMLPDYEA-UHFFFAOYSA-N 0.000 description 1
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 description 1
- UWTRFYHBXHDISN-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1.NCC(=O)C1=CC=CC=C1 UWTRFYHBXHDISN-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241001163841 Albugo ipomoeae-panduratae Species 0.000 description 1
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- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
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- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
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- 241001674044 Blattodea Species 0.000 description 1
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
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- 241000222290 Cladosporium Species 0.000 description 1
- BQDYOFYIEIHEOH-UHFFFAOYSA-N Clc1cccc(c1)C(=O)CNC(=O)c1cccc(Cl)c1 Chemical compound Clc1cccc(c1)C(=O)CNC(=O)c1cccc(Cl)c1 BQDYOFYIEIHEOH-UHFFFAOYSA-N 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
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- 239000000642 acaricide Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000006792 halocycloalkyloxycarbonyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004676 n-butylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000003094 perturbing effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なセミカルバゾン化
合物ならびに該化合物を有効成分として含有する有害生
物防除剤に関するものである。TECHNICAL FIELD The present invention relates to a novel semicarbazone compound and a pest control agent containing the compound as an active ingredient.
【０００２】[0002]
【従来の技術】従来、特開平５−４９５８号公報及び国
際特許公報（ＷＯ）９２−０６０７６号公報には殺虫活
性を有するセミカルバゾン化合物が開示されているが、
これらはベンジルフェニルケトンのセミカルバゾン化合
物であり、α−ベンゾイルアミノアセトフェノンのセミ
カルバゾン化合物に関しては何ら開示されていない。2. Description of the Related Art Conventionally, JP-A-5-4958 and International Patent Publication (WO) 92-06076 disclose semicarbazone compounds having insecticidal activity.
These are semicarbazone compounds of benzyl phenyl ketone, and nothing is disclosed regarding the semicarbazone compound of α-benzoylaminoacetophenone.
【０００３】[0003]
【発明が解決しようとする課題】殺虫剤の長年にわたる
使用により、近年、害虫が抵抗性を獲得し、従来の殺虫
剤による防除が困難になっている。また殺虫剤の一部は
毒性が高く、あるものは残留性により生態系を乱しつつ
ある。よって低毒性かつ低残留性の新規な殺虫剤の開発
が常に期待されている。また植物疾患に対して有用な農
園芸用殺菌剤の開発も常に要望されている。Due to the long-term use of insecticides, pests have acquired resistance in recent years, making it difficult to control them with conventional insecticides. In addition, some insecticides are highly toxic, and some are perturbing the ecosystem due to persistence. Therefore, the development of new insecticides with low toxicity and low residue is always expected. There is also a constant demand for the development of fungicides for agricultural and horticultural use against plant diseases.
【０００４】本発明者らはセミカルバゾン化合物につい
て鋭意研究を重ねた結果、新規なα−ベンゾイルアミノ
アセトフェノンのセミカルバゾン化合物が低薬量で優れ
た殺虫活性および殺菌活性を示し、かつホ乳動物、魚類
および益虫に対してはほとんど悪影響がない極めて有用
な化合物であることを見出し本発明を完成した。As a result of intensive studies on the semicarbazone compound, the present inventors have found that the novel semicarbazone compound of α-benzoylaminoacetophenone exhibits excellent insecticidal activity and bactericidal activity at a low dose, and is effective for mammals, fish and fish. The inventors have completed the present invention by discovering that they are extremely useful compounds that have almost no adverse effect on beneficial insects.
【０００５】[0005]
【課題を解決するための手段】本発明は一般式［Ｉ］The present invention has the general formula [I]
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】〔式中、Ｗは酸素原子又はイオウ原子を示
し、Ｘ、Ｙ、Ｚは各々独立してハロゲン原子、水酸基、
シアノ基、ニトロ基、ＳＣＮ基、トリメチルシリル基、
Ｒ9 、ＯＲ9、Ｓ（Ｏ）pＲ9基、ＯＳ（Ｏ）2Ｒ9基、Ｏ
Ｃ（Ｏ）Ｒ9基、Ｃ（Ｏ）Ｒ9基、ＣＯ2Ｒ9基、Ｃ（Ｏ）
Ｎ（Ｒ9）Ｒ10基、ＳＯ2Ｎ（Ｒ9）Ｒ10基、ＮＨＣ
（Ｏ）Ｒ9基、Ｎ（Ｒ9）Ｒ10基、隣あった炭素原子間で
形成する−ＣＨ＝ＣＨ−ＣＨ＝ＣＨ−基、−ＯＣＨ2Ｏ
−基、−ＯＣＨ2ＣＨ2Ｏ−基、−ＯＣＦ2Ｏ−基、−Ｏ
ＣＦ2ＣＦ2Ｏ−基又は−ＯＣＦ2ＣＦ2−基を示し、Ｒ1
は水素原子、Ｒ5、Ｒ5によって置換されていてもよいＣ
1〜Ｃ6アルキル基又は（Ｒ5）qによって置換されていて
もよいフェニル基を示し、Ｒ2、Ｒ3、Ｒ4は各々独立し
て水素原子、Ｃ1〜Ｃ6アルキル基、Ｃ2〜Ｃ6アルケニル
基、Ｃ2〜Ｃ6アルキニル基、Ｃ1〜Ｃ6ハロアルキル基、
Ｃ2〜Ｃ6アルコキシアルキル基、Ｃ2〜Ｃ6アルキルカル
ボニル基、Ｃ2〜Ｃ6アルコキシカルボニル基、Ｃ2〜Ｃ6
ハロアルキルカルボニル基、Ｃ1〜Ｃ6アルキルチオ基、
Ｃ1〜Ｃ6ハロアルキルチオ基、Ｒ6ＯＣ（Ｏ）Ｎ（Ｒ7）
Ｓ−基、Ｒ7（Ｒ8）ＮＳ−基又は（Ｒ5）qによって置換
されていてもよいベンジル基を示し、Ｒ5はハロゲン原
子、水酸基、シアノ基、ニトロ基、Ｃ1〜Ｃ6アルキル
基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6アルコキシ基、
Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6アルキルチオ基、
Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1〜Ｃ6アルキルスルホ
ニル基、Ｃ1〜Ｃ6ハロアルキルスルホニル基、Ｃ2〜Ｃ6
アルコキシカルボニル基、アミノ基又はジＣ1〜Ｃ6アル
キルアミノ基を示し、Ｒ6、Ｒ7、Ｒ8は各々独立してＣ1
〜Ｃ6アルキル基、（Ｒ5）qによって置換されていても
よいフェニル基又は（Ｒ5）qによって置換されていても
よいベンジル基を示し、Ｒ9はＣ1〜Ｃ6アルキル基、Ｃ1
〜Ｃ6ハロアルキル基、Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ
6ハロアルケニル基、Ｃ2〜Ｃ6アルキニル基、Ｃ2〜Ｃ6
ハロアルキニル基、Ｃ3〜Ｃ6シクロアルキル基、Ｃ3〜
Ｃ6ハロシクロアルキル基、Ｃ4〜Ｃ7シクロアルキルア
ルキル基、Ｃ2〜Ｃ6アルコキシアルキル基、Ｃ2〜Ｃ6ア
ルキルチオアルキル基、Ｃ2〜Ｃ6アルコキシカルボニル
アルキル基、Ｃ2〜Ｃ6シアノアルキル基、（Ｒ5）qによ
って置換されていてもよいフェニル基、（Ｒ5）qによっ
て置換されていてもよいベンジル基又は（Ｒ5）rによっ
て置換されていてもよいピリジル基を示し、Ｒ10は水素
原子又はＣ1〜Ｃ6アルキル基を示し、ｌは０〜５の整数
（ただし、ｌが２〜５の場合Ｘは同一であっても異なっ
ていてもよい）を示し、ｍは０〜５の整数（ただし、ｍ
が２〜５の場合Ｙは同一であっても異なっていてもよ
い）を示し、ｎは１〜５の整数（ただし、ｎが２〜５の
場合Ｚは同一であっても異なっていてもよい）を示し、
ｐは０〜２の整数を示し、ｑは０〜５の整数（ただし、
ｑが２〜５の場合Ｒ5は同一であっても異なっていても
よい）を示し、ｒは０〜４の整数（ただし、ｒが２〜４
の場合Ｒ5は同一であっても異なっていてもよい）を示
す。〕で表わされるセミカルバゾン化合物及び該化合物
の１種又は２種以上を有効成分として含有する有害生物
防除剤に関するものである。[In the formula, W represents an oxygen atom or a sulfur atom, X, Y and Z are each independently a halogen atom, a hydroxyl group,
Cyano group, nitro group, SCN group, trimethylsilyl group,
R 9 , OR 9 , S (O) p R 9 group, OS (O) 2 R 9 group, O
C (O) R 9 group, C (O) R 9 group, CO 2 R 9 group, C (O)
N (R 9 ) R 10 group, SO 2 N (R 9 ) R 10 group, NHC
(O) R 9 group, N (R 9 ) R 10 group, —CH═CH—CH═CH— group formed between adjacent carbon atoms, —OCH 2 O
- group, -OCH 2 CH 2 O- group, -OCF 2 O-groups, -O
CF 2 CF 2 O- group or -OCF 2 CF 2 - represents a group, R 1
Is a hydrogen atom, C 5 , which may be substituted by R 5 , R 5
1 to C 6 alkyl group or phenyl group optionally substituted by (R 5 ) q is shown, and R 2 , R 3 and R 4 are each independently a hydrogen atom, C 1 to C 6 alkyl group, C 2 To C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group,
C 2 -C 6 alkoxyalkyl group, C 2 -C 6 alkylcarbonyl group, C 2 -C 6 alkoxycarbonyl group, C 2 -C 6
A haloalkylcarbonyl group, a C 1 -C 6 alkylthio group,
C 1 -C 6 haloalkylthio group, R 6 OC (O) N (R 7)
S-group, R 7 (R 8 ) NS-group or benzyl group optionally substituted by (R 5 ) q is shown, wherein R 5 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, C 1 to C 6 Alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group,
A C 1 -C 6 haloalkoxy group, a C 1 -C 6 alkylthio group,
C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, C 2 -C 6
An alkoxycarbonyl group, an amino group or a di C 1 -C 6 alkylamino group, wherein R 6 , R 7 and R 8 are each independently C 1
-C 6 alkyl group, (R 5) a phenyl group or optionally substituted by q (R 5) shows a benzyl group which may be substituted by q, R 9 is C 1 -C 6 alkyl groups, C 1
To C 6 haloalkyl group, C 2 to C 6 alkenyl group, C 2 to C
6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6
Haloalkynyl group, C 3 -C 6 cycloalkyl group, C 3 ~
C 6 halocycloalkyl group, C 4 -C 7 cycloalkylalkyl, C 2 -C 6 alkoxyalkyl group, C 2 -C 6 alkylthioalkyl group, C 2 -C 6 alkoxycarbonyl group, C 2 -C 6 cyanoalkyl group, a (R 5) a phenyl group optionally substituted by q, (R 5) good benzyl group or optionally substituted by q (R 5) pyridyl group which may be substituted by r , R 10 represents a hydrogen atom or a C 1 -C 6 alkyl group, and l represents an integer of 0 to 5 (provided that when 1 is 2 to 5, X may be the same or different), m is an integer from 0 to 5 (however, m
Is 2 to 5, Y may be the same or different, and n is an integer of 1 to 5 (provided that when n is 2 to 5, Z is the same or different). Good),
p represents an integer of 0 to 2, and q is an integer of 0 to 5 (however,
When q is 2 to 5, R 5 may be the same or different, and r is an integer of 0 to 4 (provided that r is 2 to 4).
In the case of, R 5 may be the same or different). ] It is related with the semicarbazone compound represented by these, and the pest control agent which contains 1 type, or 2 or more types of this compound as an active ingredient.
【０００８】本明細書において示した各置換基の例を以
下に示す。なお、各置換基のうち炭素鎖は、直鎖、分岐
鎖又は環状の何れでもよい。以下、ｎ−はノルマル、ｉ
−はイソ、ｓｅｃ−はセカンダリー、ｔ−はターシャリ
ー、ｃ−はシクロを意味する。Examples of each substituent shown in the present specification are shown below. The carbon chain of each substituent may be linear, branched or cyclic. Hereinafter, n- is normal, i
-Is iso, sec- is secondary, t- is tertiary, and c- is cyclo.
【０００９】Ｃ1〜Ｃ6アルキル基としては、メチル基、
エチル基、ｎ−プロピル基、ｉ−プロピル基、ｃ−プロ
ピル基、ｎ−ブチル基、ｉ−ブチル基、ｓｅｃ−ブチル
基、ｔ−ブチル基、ｃ−ブチル基、ｎ−ペンチル基、ｃ
−ペンチル基、ｎ−ヘキシル基、ｃ−ヘキシル基等が挙
げられる。As the C 1 -C 6 alkyl group, a methyl group,
Ethyl group, n-propyl group, i-propyl group, c-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, c-butyl group, n-pentyl group, c
-Pentyl group, n-hexyl group, c-hexyl group and the like.
【００１０】Ｃ2〜Ｃ6アルケニル基としては、エテニル
基、２−プロペニル基、２−メチル−２−プロペニル
基、２−ブテニル基等が挙げられる。Examples of the C 2 -C 6 alkenyl group include ethenyl group, 2-propenyl group, 2-methyl-2-propenyl group and 2-butenyl group.
【００１１】Ｃ2〜Ｃ6アルキニル基としては、エチニル
基、２−プロピニル基、２−ブチニル基等が挙げられ
る。Examples of the C 2 -C 6 alkynyl group include ethynyl group, 2-propynyl group and 2-butynyl group.
【００１２】Ｃ2〜Ｃ6アルコキシアルキル基としては、
メトキシメチル基、エトキシメチル基、１−メトキシエ
チル基等が挙げられる。As the C 2 -C 6 alkoxyalkyl group,
Examples thereof include a methoxymethyl group, an ethoxymethyl group and a 1-methoxyethyl group.
【００１３】Ｃ2〜Ｃ6アルキルカルボニル基としては、
メチルカルボニル基、エチルカルボニル基、ｎ−プロピ
ルカルボニル基、ｉ−プロピルカルボニル基、ｃ−プロ
ピルカルボニル基、ｎ−ブチルカルボニル基、ｉ−ブチ
ルカルボニル基、ｓｅｃ−ブチルカルボニル基、ｔ−ブ
チルカルボニル基、ｃ−ブチルカルボニル基等が挙げら
れる。As the C 2 -C 6 alkylcarbonyl group,
Methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, i-propylcarbonyl group, c-propylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group, sec-butylcarbonyl group, t-butylcarbonyl group, Examples thereof include c-butylcarbonyl group.
【００１４】Ｃ2〜Ｃ6アルコキシカルボニル基として
は、メトキシカルボニル基、エトキシカルボニル基、ｎ
−プロポキシカルボニル基、ｉ−プロポキシカルボニル
基、ｃ−プロポキシカルボニル基、ｎ−ブトキシカルボ
ニル基、ｉ−ブトキシカルボニル基、ｓｅｃ−ブトキシ
カルボニル基、ｔ−ブトキシカルボニル基、ｃ−ブトキ
シカルボニル基等が挙げられる。The C 2 -C 6 alkoxycarbonyl group includes methoxycarbonyl group, ethoxycarbonyl group, n
-Propoxycarbonyl group, i-propoxycarbonyl group, c-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, t-butoxycarbonyl group, c-butoxycarbonyl group and the like. .
【００１５】ハロゲン原子としては、フッ素原子、塩素
原子、臭素原子、ヨウ素原子が挙げられる。Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
【００１６】Ｗとしては酸素原子とイオウ原子が挙げら
れるが、好ましくは酸素原子が挙げられる。Examples of W include an oxygen atom and a sulfur atom, preferably an oxygen atom.
【００１７】Ｘ、Ｙ、Ｚとしては各々独立してハロゲン
原子、水酸基、シアノ基、ニトロ基、ＳＣＮ基、トリメ
チルシリル基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアル
キル基、Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ6ハロアルケニ
ル基、Ｃ2〜Ｃ6アルキニル基、Ｃ2〜Ｃ6ハロアルキニル
基、Ｃ3〜Ｃ6シクロアルキル基、Ｃ3〜Ｃ6ハロシクロア
ルキル基、Ｃ4〜Ｃ7シクロアルキルアルキル基、Ｃ2〜
Ｃ6アルコキシアルキル基、Ｃ2〜Ｃ6アルキルチオアル
キル基、Ｃ2〜Ｃ6アルコキシカルボニルアルキル基、Ｃ
2〜Ｃ6シアノアルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1
〜Ｃ6ハロアルコキシ基、Ｃ2〜Ｃ6アルケニルオキシ
基、Ｃ2〜Ｃ6ハロアルケニルオキシ基、Ｃ2〜Ｃ6アルキ
ニルオキシ基、Ｃ2〜Ｃ6ハロアルキニルオキシ基、Ｃ3
〜Ｃ6シクロアルキルオキシ基、Ｃ3〜Ｃ6ハロシクロア
ルキルオキシ基、Ｃ4〜Ｃ7シクロアルキルアルキルオキ
シ基、Ｃ2〜Ｃ6アルコキシアルキルオキシ基、Ｃ2〜Ｃ6
アルキルチオアルキルオキシ基、Ｃ3〜Ｃ6アルコキシカ
ルボニルアルキルオキシ基、Ｃ2〜Ｃ6シアノアルキルオ
キシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキ
ルチオ基、Ｃ2〜Ｃ6アルケニルチオ基、Ｃ2〜Ｃ6ハロア
ルケニルチオ基、Ｃ2〜Ｃ6アルキニルチオ基、Ｃ2〜Ｃ6
ハロアルキニルチオ基、Ｃ3〜Ｃ6シクロアルキルチオ
基、Ｃ3〜Ｃ6ハロシクロアルキルチオ基、Ｃ4〜Ｃ7シク
ロアルキルアルキルチオ基、Ｃ2〜Ｃ6アルコキシアルキ
ルチオ基、Ｃ2〜Ｃ6アルキルチオアルキルチオ基、Ｃ2
〜Ｃ6アルコキシカルボニルアルキルチオ基、Ｃ2〜Ｃ6
シアノアルキルチオ基、Ｃ1〜Ｃ6アルキルスルフィニル
基、Ｃ1〜Ｃ6ハロアルキルスルフィニル基、Ｃ2〜Ｃ6ア
ルケニルスルフィニル基、Ｃ2〜Ｃ6ハロアルケニルスル
フィニル基、Ｃ2〜Ｃ6アルキニルスルフィニル基、Ｃ2
〜Ｃ6ハロアルキニルスルフィニル基、Ｃ3〜Ｃ6シクロ
アルキルスルフィニル基、Ｃ3〜Ｃ6ハロシクロアルキル
スルフィニル基、Ｃ4〜Ｃ7シクロアルキルアルキルスル
フィニル基、Ｃ2〜Ｃ6アルコキシアルキルスルフィニル
基、Ｃ2〜Ｃ6アルキルチオアルキルスルフィニル基、Ｃ
1〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6ハロアルキルス
ルホニル基、Ｃ2〜Ｃ6アルケニルスルホニル基、Ｃ2〜
Ｃ6ハロアルケニルスルホニル基、Ｃ2〜Ｃ6アルキニル
スルホニル基、Ｃ2〜Ｃ6ハロアルキニルスルホニル基、
Ｃ3〜Ｃ6シクロアルキルスルホニル基、Ｃ3〜Ｃ6ハロシ
クロアルキルスルホニル基、Ｃ4〜Ｃ7シクロアルキルア
ルキルスルホニル基、Ｃ2〜Ｃ6アルコキシアルキルスル
ホニル基、Ｃ2〜Ｃ6アルキルチオアルキルスルホニル
基、Ｃ2〜Ｃ6アルコキシカルボニルアルキルスルホニル
基、Ｃ2〜Ｃ6シアノアルキルスルホニル基、Ｃ1〜Ｃ6ア
ルキルスルホニルオキシ基、Ｃ1〜Ｃ6ハロアルキルスル
ホニルオキシ基、Ｃ3〜Ｃ6シクロアルキルスルホニルオ
キシ基、Ｃ3〜Ｃ6ハロシクロアルキルスルホニルオキシ
基、Ｃ2〜Ｃ6シアノアルキルスルホニルオキシ基、Ｃ2
〜Ｃ7アルキルカルボニルオキシ基、Ｃ2〜Ｃ7ハロアル
キルカルボニルオキシ基、Ｃ4〜Ｃ7シクロアルキルカル
ボニルオキシ基、Ｃ4〜Ｃ7ハロシクロアルキルカルボニ
ルオキシ基、Ｃ 3〜Ｃ7シアノアルキルカルボニルオキシ
基、Ｃ2〜Ｃ7アルキルカルボニル基、Ｃ 2〜Ｃ7ハロアル
キルカルボニル基、Ｃ4〜Ｃ7シクロアルキルカルボニル
基、Ｃ4〜Ｃ7ハロシクロアルキルカルボニル基、Ｃ3〜
Ｃ7シアノアルキルカルボニル基、Ｃ2〜Ｃ7アルコキシ
カルボニル基、Ｃ2〜Ｃ7ハロアルコキシカルボニル基、
Ｃ 4〜Ｃ7シクロアルキルオキシカルボニル基、Ｃ4〜Ｃ7
ハロシクロアルキルオキシカルボニル基、Ｃ3〜Ｃ7シア
ノアルキルオキシカルボニル基、モノＣ1〜Ｃ6アルキル
アミノカルボニル基、モノＣ1〜Ｃ6ハロアルキルアミノ
カルボニル基、ジＣ 1〜Ｃ6アルキルアミノカルボニル
基、ジＣ1〜Ｃ6ハロアルキルアミノカルボニル基、モノ
Ｃ1〜Ｃ6アルキルアミノスルホニル基、モノＣ1〜Ｃ6ハ
ロアルキルアミノスルホニル基、ジＣ1〜Ｃ6アルキルア
ミノスルホニル基、ジＣ1〜Ｃ6ハロアルキルアミノスル
ホニル基、アミノカルボニル基、アミノスルホニル基、
ホルミルアミノ基、Ｃ2〜Ｃ7アルキルカルボニルアミノ
基、Ｃ2〜Ｃ7ハロアルキルカルボニルアミノ基、アミノ
基、モノＣ1〜Ｃ6アルキルアミノ基、モノＣ1〜Ｃ6ハロ
アルキルアミノ基、ジＣ1〜Ｃ6アルキルアミノ基、ジＣ
1〜Ｃ6ハロアルキルアミノ基、隣あった炭素原子間で形
成する−ＣＨ＝ＣＨ−ＣＨ＝ＣＨ−基、−ＯＣＨ2Ｏ−
基、−ＯＣＨ2ＣＨ2Ｏ−基、−ＯＣＦ2Ｏ−基、−ＯＣ
Ｆ2ＣＦ2Ｏ−基、−ＯＣＦ2ＣＦ2−基、置換されていて
もよいフェニル基、置換されていてもよいフェノキシ
基、置換されていてもよいフェニルチオ基、置換されて
いてもよいフェニルスルフィニル基、置換されていても
よいフェニルスルホニル基、置換されていてもよいフェ
ニルスルホニルオキシ基、置換されていてもよいフェニ
ルカルボニルオキシ基、置換されていてもよいフェニル
カルボニル基、置換されていてもよいフェノキシカルボ
ニル基、置換されていてもよいフェニルアミノカルボニ
ル基、置換されていてもよいフェニルスルホニルアミノ
基、置換されていてもよいフェニルカルボニルアミノ
基、置換されていてもよいフェニルアミノ基、置換され
ていてもよいベンジル基、置換されていてもよいベンジ
ルオキシ基、置換されていてもよいベンジルチオ基、置
換されていてもよいベンジルスルフィニル基、置換され
ていてもよいベンジルスルホニル基、置換されていても
よいベンジルスルホニルオキシ基、置換されていてもよ
いベンジルカルボニルオキシ基、置換されていてもよい
ベンジルカルボニル基、置換されていてもよいベンジル
オキシカルボニル基、置換されていてもよいベンジルア
ミノカルボニル基、置換されていてもよいベンジルスル
ホニルアミノ基、置換されていてもよいベンジルカルボ
ニルアミノ基、置換されていてもよいベンジルアミノ
基、置換されていてもよいピリジル基、置換されていて
もよいピリジルオキシ基、置換されていてもよいピリジ
ルチオ基、置換されていてもよいピリジルスルフィニル
基、置換されていてもよいピリジルスルホニル基、置換
されていてもよいピリジルスルホニルオキシ基、置換さ
れていてもよいピリジルカルボニルオキシ基、置換され
ていてもよいピリジルカルボニル基、置換されていても
よいピリジルオキシカルボニル基、置換されていてもよ
いピリジルアミノカルボニル基、置換されていてもよい
ピリジルスルホニルアミノ基、置換されていてもよいピ
リジルカルボニルアミノ基又は置換されていてもよいピ
リジルアミノ基（ただし置換されていてもよい置換基と
しては、ハロゲン原子、水酸基、シアノ基、ニトロ基、
Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜
Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1
〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6ハロアルキルス
ルホニル基、Ｃ1〜Ｃ6アルコキシカルボニル基、アミノ
基又はジＣ1〜Ｃ6アルキルアミノ基が挙げられる。）が
挙げられる。X, Y and Z are each independently halogen.
Atom, hydroxyl group, cyano group, nitro group, SCN group, trime
Cylsilyl group, C1~ C6Alkyl group, C1~ C6Halo al
Kill group, C2~ C6Alkenyl group, C2~ C6Halo archeni
Lu group, C2~ C6Alkynyl group, C2~ C6Haloalkynyl
Base, C3~ C6Cycloalkyl group, C3~ C6Halo cycloa
Rukiru group, CFour~ C7Cycloalkylalkyl group, C2~
C6Alkoxyalkyl group, C2~ C6Alkyl thioal
Kill group, C2~ C6Alkoxycarbonylalkyl group, C
2~ C6Cyanoalkyl group, C1~ C6Alkoxy group, C1
~ C6Haloalkoxy group, C2~ C6Alkenyloxy
Base, C2~ C6Haloalkenyloxy group, C2~ C6Archi
Nyloxy group, C2~ C6Haloalkynyloxy group, C3
~ C6Cycloalkyloxy group, C3~ C6Halo cycloa
Rualkyloxy group, CFour~ C7Cycloalkyl alkyl oki
Shi group, C2~ C6Alkoxyalkyloxy group, C2~ C6
Alkylthioalkyloxy group, C3~ C6Alkoxyca
Rubonylalkyloxy group, C2~ C6Cyanoalkyl
Xy group, C1~ C6Alkylthio group, C1~ C6Halo Archi
Ruthio group, C2~ C6Alkenylthio group, C2~ C6Haloa
Lucenylthio group, C2~ C6Alkynylthio group, C2~ C6
Haloalkynylthio group, C3~ C6Cycloalkylthio
Base, C3~ C6Halocycloalkylthio group, CFour~ C7Shiku
Roalkylalkylthio group, C2~ C6Alkoxy alk
Ruthio group, C2~ C6Alkylthio alkylthio group, C2
~ C6Alkoxycarbonylalkylthio group, C2~ C6
Cyanoalkylthio group, C1~ C6Alkylsulfinyl
Base, C1~ C6Haloalkylsulfinyl group, C2~ C6A
Lucenylsulfinyl group, C2~ C6Haloalkenyl sul
Finyl group, C2~ C6Alkynylsulfinyl group, C2
~ C6Haloalkynylsulfinyl group, C3~ C6Cyclo
Alkylsulfinyl group, C3~ C6Halocycloalkyl
Sulfinyl group, CFour~ C7Cycloalkyl alkyl sul
Finyl group, C2~ C6Alkoxyalkyl sulfinyl
Base, C2~ C6Alkylthioalkylsulfinyl group, C
1~ C6Alkylsulfonyl group, C1~ C6Haloalkyls
Ruphonyl group, C2~ C6Alkenylsulfonyl group, C2~
C6Haloalkenylsulfonyl group, C2~ C6Alkynyl
Sulfonyl group, C2~ C6A haloalkynylsulfonyl group,
C3~ C6Cycloalkylsulfonyl group, C3~ C6Haroshi
Chloroalkylsulfonyl group, CFour~ C7Cycloalkyl
Rukylsulphonyl group, C2~ C6Alkoxyalkyl sulphate
Honyl group, C2~ C6Alkylthioalkylsulfonyl
Base, C2~ C6Alkoxycarbonylalkylsulfonyl
Base, C2~ C6Cyanoalkylsulfonyl group, C1~ C6A
Rukylsulphonyloxy group, C1~ C6Haloalkyl sul
Honyloxy group, C3~ C6Cycloalkylsulfonyl
Xy group, C3~ C6Halocycloalkylsulfonyloxy
Base, C2~ C6Cyanoalkylsulfonyloxy group, C2
~ C7Alkylcarbonyloxy group, C2~ C7Halo al
Killcarbonyloxy group, CFour~ C7Cycloalkylcal
Bonyloxy group, CFour~ C7Halocycloalkylcarboni
Luoxy group, C 3~ C7Cyanoalkylcarbonyloxy
Base, C2~ C7Alkylcarbonyl group, C 2~ C7Halo al
Killcarbonyl group, CFour~ C7Cycloalkyl carbonyl
Base, CFour~ C7Halocycloalkylcarbonyl group, C3~
C7Cyanoalkylcarbonyl group, C2~ C7Alkoxy
Carbonyl group, C2~ C7A haloalkoxycarbonyl group,
C Four~ C7Cycloalkyloxycarbonyl group, CFour~ C7
Halocycloalkyloxycarbonyl group, C3~ C7Shea
Noalkyloxycarbonyl group, Mono C1~ C6Alkyl
Aminocarbonyl group, Mono C1~ C6Haloalkylamino
Carbonyl group, di-C 1~ C6Alkylaminocarbonyl
Group, di-C1~ C6Haloalkylaminocarbonyl group, mono
C1~ C6Alkylaminosulfonyl group, Mono C1~ C6Ha
Roalkylaminosulfonyl group, di-C1~ C6Alkyla
Minosulfonyl group, di-C1~ C6Haloalkylaminosul
Sulfonyl group, aminocarbonyl group, aminosulfonyl group,
Formylamino group, C2~ C7Alkylcarbonylamino
Base, C2~ C7Haloalkylcarbonylamino group, amino
Group, Mono C1~ C6Alkylamino group, Mono C1~ C6Halo
Alkylamino group, di-C1~ C6Alkylamino group, di-C
1~ C6Haloalkylamino group, formed between adjacent carbon atoms
Formed -CH = CH-CH = CH- group, -OCH2O-
Group, -OCH2CH2O-group, -OCF2O-group, -OC
F2CF2O-group, -OCF2CF2-Group, substituted
Optionally phenyl group, optionally substituted phenoxy
Group, optionally substituted phenylthio group, substituted
Phenylsulfinyl group which may be present, which may be substituted
Good phenylsulfonyl group, optionally substituted phenyl
Nylsulfonyloxy group, optionally substituted phenyl
Lucarbonyloxy group, optionally substituted phenyl
Carbonyl group, optionally substituted phenoxycarbo
Nyl group, optionally substituted phenylaminocarbonyl
Group, optionally substituted phenylsulfonylamino
Group, optionally substituted phenylcarbonylamino
Group, optionally substituted phenylamino group, substituted
Optionally substituted benzyl group, optionally substituted benzyl
Ruoxy group, optionally substituted benzylthio group,
Optionally substituted benzylsulfinyl group, substituted
Optionally substituted benzylsulfonyl group, optionally substituted
Good benzylsulfonyloxy group, optionally substituted
A benzylcarbonyloxy group, which may be substituted
Benzylcarbonyl group, optionally substituted benzyl
Oxycarbonyl group, optionally substituted benzyl group
Minocarbonyl group, optionally substituted benzylsul
Fonylamino group, optionally substituted benzylcarbo
Nylamino group, optionally substituted benzylamino
Group, optionally substituted pyridyl group, optionally substituted
Optionally pyridyloxy group, optionally substituted pyridi
Ruthio group, optionally substituted pyridylsulfinyl
Group, optionally substituted pyridylsulfonyl group, substituted
Optionally substituted pyridylsulfonyloxy group, substituted
Optionally substituted pyridylcarbonyloxy group, substituted
Optionally substituted pyridylcarbonyl group, optionally substituted
Good pyridyloxycarbonyl group, which may be substituted
A pyridylaminocarbonyl group, which may be substituted
Pyridylsulfonylamino group, optionally substituted
Lysylcarbonylamino group or optionally substituted
Lysylamino group (provided that an optionally substituted substituent
Then, halogen atom, hydroxyl group, cyano group, nitro group,
C1~ C6Alkyl group, C1~ C6Haloalkyl group, C1~
C6Alkylthio group, C1~ C6Haloalkylthio group, C1
~ C6Alkylsulfonyl group, C1~ C6Haloalkyls
Ruphonyl group, C1~ C6Alkoxycarbonyl group, amino
Group or di-C1~ C6An alkylamino group is mentioned. )But
Can be mentioned.
【００１８】Ｘとして好ましくは、ハロゲン原子、シア
ノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロア
ルキル基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6ハロア
ルキルチオ基、Ｃ1〜Ｃ6ハロアルキルスルホニルオキシ
基が挙げられる。X is preferably a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 haloalkoxy group, or a C 1 -C 6 haloalkylthio group. , C 1 to C 6 haloalkylsulfonyloxy groups.
【００１９】Ｙとして好ましくは、ハロゲン原子、シア
ノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロア
ルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1〜Ｃ6ハロアルコ
キシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキ
ルチオ基、Ｃ1〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6ハ
ロアルキルスルホニル基、Ｃ1〜Ｃ6ハロアルキルスルホ
ニルオキシ基、隣あった炭素原子間で形成する−ＯＣＦ
2Ｏ−基又は−ＯＣＦ2ＣＦ2Ｏ−基が挙げられる。Y is preferably a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, the adjoining carbon atoms Formed between -OCF
2 O- group or -OCF 2 CF 2 O- group.
【００２０】Ｚとして好ましくは、ハロゲン原子、シア
ノ基、ニトロ基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6ハ
ロアルコキシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハ
ロアルキルチオ基、Ｃ1〜Ｃ6アルキルスルフィニル基、
Ｃ1〜Ｃ6ハロアルキルスルフィニル基、Ｃ1〜Ｃ6アルキ
ルスルホニル基、Ｃ1〜Ｃ6ハロアルキルスルホニル基、
Ｃ1〜Ｃ6アルキルスルホニルオキシ基、Ｃ1〜Ｃ6ハロア
ルキルスルホニルオキシ基、隣あった炭素原子間で形成
する−ＯＣＦ2Ｏ−基、−ＯＣＦ2ＣＦ2Ｏ−基又は−Ｏ
ＣＦ2ＣＦ2−基が挙げられる。Z is preferably a halogen atom, a cyano group, a nitro group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 haloalkoxy group, a C 1 -C 6 alkylthio group or a C 1 -C 6 haloalkylthio group. A C 1 -C 6 alkylsulfinyl group,
A C 1 -C 6 haloalkylsulfinyl group, a C 1 -C 6 alkylsulfonyl group, a C 1 -C 6 haloalkylsulfonyl group,
C 1 -C 6 alkylsulfonyloxy group, C 1 -C 6 haloalkylsulfonyl group, next there was -OCF 2 O-group formed between carbon atoms, -OCF 2 CF 2 O- group or -O
CF 2 CF 2 - group.
【００２１】Ｒ1としては、ハロゲン原子、水酸基、シ
アノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロ
アルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1〜Ｃ6ハロアル
コキシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアル
キルチオ基、Ｃ1〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6
ハロアルキルスルホニル基、Ｃ2〜Ｃ6アルコキシカルボ
ニル基、アミノ基、ジＣ1〜Ｃ6アルキルアミノ基又は置
換されていてもよいフェニル基（ただし、置換されてい
てもよい置換基としては、ハロゲン原子、水酸基、シア
ノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロア
ルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1〜Ｃ6ハロアルコ
キシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキ
ルチオ基、Ｃ1〜Ｃ6アルキルスルホニル基、Ｃ2〜Ｃ6ア
ルコキシカルボニル基、アミノ基又はジＣ1〜Ｃ6アルキ
ルアミノ基が挙げられる）が挙げられる。R 1 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, or a C 1 -C 6 haloalkoxy. Group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6
Haloalkylsulfonyl group, C 2 -C 6 alkoxycarbonyl group, an amino group, di C 1 -C 6 alkylamino group or an optionally substituted phenyl group (wherein, as the optionally substituted substituent, a halogen atom , A hydroxyl group, a cyano group, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkoxy group, a C 1 to C 6 haloalkoxy group, a C 1 to C 6 alkylthio group, And C 1 to C 6 haloalkylthio group, C 1 to C 6 alkylsulfonyl group, C 2 to C 6 alkoxycarbonyl group, amino group or di C 1 to C 6 alkylamino group).
【００２２】Ｒ1として好ましくは、水素原子又はＣ1〜
Ｃ6アルキル基が挙げられる。R 1 is preferably a hydrogen atom or C 1
C 6 alkyl group.
【００２３】Ｒ2、Ｒ3及びＲ4としては、水素原子、Ｃ1
〜Ｃ6アルキル基、Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ6ア
ルキニル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ2〜Ｃ6アルコ
キシアルキル基、Ｃ2〜Ｃ6アルキルカルボニル基、Ｃ2
〜Ｃ6アルコキシカルボニル基、Ｃ2〜Ｃ6ハロアルキル
カルボニル基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロ
アルキルチオ基、Ｃ2〜Ｃ12ジアルキルアミノチオ基、
Ｃ3〜Ｃ12（アルキル）アルコキシカルボニルアミノチ
オ基又は置換されていてもよいベンジル基（ただし、置
換されていてもよい置換基としては、ハロゲン原子、水
酸基、シアノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1
〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1〜Ｃ
6ハロアルコキシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ
6ハロアルキルチオ基、Ｃ1〜Ｃ6アルキルスルホニル
基、Ｃ2〜Ｃ6アルコキシカルボニル基、アミノ基又はジ
Ｃ1〜Ｃ6アルキルアミノ基が挙げられる）が挙げられ
る。R 2 , R 3 and R 4 are a hydrogen atom, C 1
-C 6 alkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 alkynyl group, C 1 -C 6 haloalkyl group, C 2 -C 6 alkoxyalkyl group, C 2 -C 6 alkylcarbonyl group, C 2
To C 6 alkoxycarbonyl group, C 2 to C 6 haloalkylcarbonyl group, C 1 to C 6 alkylthio group, C 1 to C 6 haloalkylthio group, C 2 to C 12 dialkylaminothio group,
A C 3 -C 12 (alkyl) alkoxycarbonylaminothio group or an optionally substituted benzyl group (provided that the optionally substituted substituents are a halogen atom, a hydroxyl group, a cyano group, a nitro group, C 1 to C 6 alkyl group, C 1
To C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C
6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C
And 6 haloalkylthio groups, C 1 -C 6 alkylsulfonyl groups, C 2 -C 6 alkoxycarbonyl groups, amino groups or di-C 1 -C 6 alkylamino groups).
【００２４】Ｒ2、Ｒ3及びＲ4として好ましくは、水素
原子又はＣ1〜Ｃ6アルキル基があげられる。R 2 , R 3 and R 4 are preferably a hydrogen atom or a C 1 -C 6 alkyl group.
【００２５】ｌは０〜２の整数が好ましい。L is preferably an integer of 0 to 2.
【００２６】ｍは０〜２の整数が好ましい。M is preferably an integer of 0-2.
【００２７】ｎは１〜３の整数が好ましい。N is preferably an integer of 1 to 3.
【００２８】好ましい本発明化合物としては、Ｗが酸素
原子を示し、Ｘが、ハロゲン原子、シアノ基、ニトロ
基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ
1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6ハロアルキルチオ基
又はＣ 1〜Ｃ6ハロアルキルスルホニルオキシ基を示し、
Ｙが、ハロゲン原子、シアノ基、ニトロ基、Ｃ1〜Ｃ6ア
ルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6アルコキ
シ基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6アルキルチ
オ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1〜Ｃ6アルキル
スルホニル基、Ｃ1〜Ｃ6ハロアルキルスルホニル基、Ｃ
1〜Ｃ6ハロアルキルスルホニルオキシ基、隣あった炭素
原子間で形成する−ＯＣＦ2Ｏ−基又は−ＯＣＦ2ＣＦ2
Ｏ−基を示し、Ｚが、ハロゲン原子、シアノ基、ニトロ
基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6ハロアルコキシ
基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキルチ
オ基、Ｃ1〜Ｃ6アルキルスルフィニル基、Ｃ1〜Ｃ6ハロ
アルキルスルフィニル基、Ｃ 1〜Ｃ6アルキルスルホニル
基、Ｃ1〜Ｃ6ハロアルキルスルホニル基、Ｃ1〜Ｃ6アル
キルスルホニルオキシ基、Ｃ1〜Ｃ6ハロアルキルスルホ
ニルオキシ基、隣あった炭素原子間で形成する−ＯＣＦ
2Ｏ−基、−ＯＣＦ2ＣＦ2Ｏ−基又は−ＯＣＦ2ＣＦ2−
基を示し、Ｒ1、Ｒ2、Ｒ3、Ｒ4が各々独立して水素原子
又はＣ1〜Ｃ6アルキル基を示し、ｌおよびｍが各々独立
して０〜２の整数を示し、ｎが１〜３の整数を示すセミ
カルバゾン化合物［Ｉ］が挙げられる。As the preferred compound of the present invention, W is oxygen
Represents an atom, X is a halogen atom, a cyano group, nitro
Base, C1~ C6Alkyl group, C1~ C6Haloalkyl group, C
1~ C6Haloalkoxy group, C1~ C6Haloalkylthio group
Or C 1~ C6Represents a haloalkylsulfonyloxy group,
Y is a halogen atom, cyano group, nitro group, C1~ C6A
Rukiru group, C1~ C6Haloalkyl group, C1~ C6Arcoki
Shi group, C1~ C6Haloalkoxy group, C1~ C6Alkylchi
O group, C1~ C6Haloalkylthio group, C1~ C6Alkyl
Sulfonyl group, C1~ C6Haloalkylsulfonyl group, C
1~ C6Haloalkylsulfonyloxy group, adjacent carbon
-OCF formed between atoms2O-group or -OCF2CF2
Represents an O- group, Z is a halogen atom, a cyano group, nitro
Base, C1~ C6Haloalkyl group, C1~ C6Haloalkoxy
Base, C1~ C6Alkylthio group, C1~ C6Haloalkyl
O group, C1~ C6Alkylsulfinyl group, C1~ C6Halo
Alkylsulfinyl group, C 1~ C6Alkylsulfonyl
Base, C1~ C6Haloalkylsulfonyl group, C1~ C6Al
Killsulfonyloxy group, C1~ C6Haloalkyl sulfo
Nyloxy group, -OCF formed between adjacent carbon atoms
2O-group, -OCF2CF2O-group or -OCF2CF2−
Group, R1, R2, R3, RFourAre each independently a hydrogen atom
Or C1~ C6Represents an alkyl group, and l and m are independent of each other
And an integer of 0 to 2, and n is a semi of an integer of 1 to 3.
Carbazone compound [I] is mentioned.
【００２９】尚、一般式［Ｉ］で表される本発明化合物
は、Ｅ体及びＺ体の異性体が存在するが、本発明は、こ
れらのＥ体、Ｚ体並びにＥ体及びＺ体を任意の割合で含
む混合物を包含する。また不斉炭素原子を有する化合物
の場合には、Ｒ体及びＳ体が含まれる。更に、立体配置
異性体が存在する場合には、Ｅ体及びＺ体が含まれる。The compound of the present invention represented by the general formula [I] has isomers of E isomer and Z isomer, and the present invention includes the E isomer, Z isomer and E isomer and Z isomer. It includes a mixture containing it in any ratio. In the case of a compound having an asymmetric carbon atom, R form and S form are included. Further, when there are configurational isomers, the E form and the Z form are included.
【００３０】本発明に包含される化合物としては、具体
的には例えば、第１表の示す化合物が挙げられる。但
し、第１表の化合物は例示のためのものであって、本発
明はこれらのみに限定されるものではない。Specific examples of the compounds included in the present invention include the compounds shown in Table 1. However, the compounds in Table 1 are for exemplification, and the present invention is not limited to these.
【００３１】第１表のＱ１〜Ｑ７は次の式で表される基
である。Q1 to Q7 in Table 1 are groups represented by the following formula.
【００３２】[0032]
【化３】 [Chemical 3]
【００３３】第 １ 表Table 1
【００３４】[0034]
【化４】 [Chemical 4]
【００３５】[0035]
【表１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 2-F H H H H O 3-F 4-F 3-F H H H H O 3-F 4-F 4-F H H H H O 3-F 4-F 2-Cl H H H H O 3-F 4-F 3-Cl H H H H O 3-F 4-F 4-Cl H H H H O 3-F 4-F 3-Br H H H H O 3-F 4-F 4-Br H H H H O 3-F 4-F 4-I H H H H O 3-F 4-F 4-CH3 H H H H O 3-F 4-F 4-CH2CH3 H H H H O 3-F 4-F 4-CH(CH3)2 H H H H O 3-F 4-F 4-CH2CH2CH2CH3 H H H H O 3-F 4-F 4-C(CH3)3 H H H H O 3-F 4-F 4-CH2CH=CH2 H H H H O 3-F 4-F 4-C≡CH H H H H O 3-F 4-F 4-CH2Ｃ≡CH H H H H O 3-F 4-F 4-Q1 H H H H O 3-F 4-F 4-Q2 H H H H O 3-F 4-F 4-Q3 H H H H O 3-F 4-F 4-Q4 H H H H O 3-F 4-F 4-CHF2 H H H H O 3-F 4-F 4-CH2Br ───────────────────────────────────[Table 1] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 2-FHHHHO 3- F 4-F 3-FHHHHO 3-F 4-F 4-FHHHHO 3-F 4-F 2-Cl HHHHO 3-F 4-F 3-Cl HHHHO 3-F 4-F 4-Cl HHHHO 3-F 4 -F 3-Br HHHHO 3-F 4-F 4-Br HHHHO 3-F 4-F 4-IHHHHO 3-F 4-F 4-CH 3 HHHHO 3-F 4-F 4-CH 2 CH 3 HHHHO 3 -F 4-F 4-CH (CH 3 ) 2 HHHHO 3-F 4-F 4-CH 2 CH 2 CH 2 CH 3 HHHHO 3-F 4-F 4-C (CH 3 ) 3 HHHHO 3-F 4 -F 4-CH 2 CH = CH 2 HHHHO 3-F 4-F 4-C ≡ CH HHHHO 3-F 4-F 4-CH 2 C ≡ CH HHHHO 3-F 4-F 4-Q1 HHHHO 3-F 4-F 4-Q2 HHHHO 3-F 4-F 4-Q3 HHHHO 3-F 4-F 4-Q4 HHHHO 3-F 4-F 4-CHF 2 HHHHO 3-F 4-F 4-CH 2 Br ─ ──────────────────────────────────
【００３６】[0036]
【表２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 4-CH2Cl H H H H O 3-F 4-F 2-CF3 H H H H O 3-F 4-F 3-CF3 H H H H O 3-F 4-F 4-CF3 H H H H O 3-F 4-F 4-CH2CH=CHCl H H H H O 3-F 4-F 4-CH=C(Cl)CF3 H H H H O 3-F 4-F 4-CH2Ｃ≡CBr H H H H O 3-F 4-F 4-(Q4-1-Cl) H H H H O 3-F 4-F 4-CH2CN H H H H O 3-F 4-F 4-CH2CH(CH3)CN H H H H O 3-F 4-F 4-CH2OH H H H H O 3-F 4-F 4-CH2CO2H H H H H O 3-F 4-F 4-OCH3 H H H H O 3-F 4-F 4-OCH2CH3 H H H H O 3-F 4-F 4-OCH(CH3)2 H H H H O 3-F 4-F 4-OC(CH3)3 H H H H O 3-F 4-F 4-OCH2CH=CH2 H H H H O 3-F 4-F 4-OCH2C≡CH H H H H O 3-F 4-F 4-O(Q4) H H H H O 3-F 4-F 4-OCHF2 H H H H O 3-F 4-F 4-OCF2Br H H H H O 3-F 4-F 2-OCF3 H H H H O 3-F 4-F 3-OCF3 ───────────────────────────────────[Table 2] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 4-CH 2 Cl HHHHO 3-F 4-F 2-CF 3 HHHHO 3-F 4-F 3-CF 3 HHHHO 3-F 4-F 4-CF 3 HHHHO 3-F 4-F 4-CH 2 CH = CHCl HHHHO 3- F 4-F 4-CH = C (Cl) CF 3 HHHHO 3-F 4-F 4-CH 2 C ≡ CBr HHHHO 3-F 4-F 4- (Q4-1-Cl) HHHHO 3-F 4- F 4-CH 2 CN HHHHO 3-F 4-F 4-CH 2 CH (CH 3 ) CN HHHHO 3-F 4-F 4-CH 2 OH HHHHO 3-F 4-F 4-CH 2 CO 2 HHHHHO 3 -F 4-F 4-OCH 3 HHHHO 3-F 4-F 4-OCH 2 CH 3 HHHHO 3-F 4-F 4-OCH (CH 3 ) 2 HHHHO 3-F 4-F 4-OC (CH 3 ) 3 HHHHO 3-F 4-F 4-OCH 2 CH = CH 2 HHHHO 3-F 4-F 4-OCH 2 C ≡ CH HHHHO 3-F 4-F 4-O (Q4) HHHHO 3-F 4- F 4-OCHF 2 HHHHO 3-F 4-F 4-OCF 2 Br HHHHO 3-F 4-F 2-OCF 3 HHHHO 3-F 4-F 3-OCF 3 ──────────── ────────────────────────
【００３７】[0037]
【表３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 4-OCF3 H H H H O 3-F 4-F 4-OCH2CF3 H H H H O 3-F 4-F 4-OCF2CF3 H H H H O 3-F 4-F 4-OCF2CHF2 H H H H O 3-F 4-F 4-OCF2CHCl2 H H H H O 3-F 4-F 4-OCF2CHFCl H H H H O 3-F 4-F 4-OCF2CHFBr H H H H O 3-F 4-F 4-0CF2CF2CF3 H H H H O 3-F 4-F 4-OCH2CH=CHCl H H H H O 3-F 4-F 4-OCH2C≡CBr H H H H O 3-F 4-F 4-O(Q4-2,2-Cl2) H H H H O 3-F 4-F 4-SCH3 H H H H O 3-F 4-F 4-SCH2CH=CH2 H H H H O 3-F 4-F 4-SCH2C≡CH H H H H O 3-F 4-F 4-S(Q4) H H H H O 3-F 4-F 4-SCHF2 H H H H O 3-F 4-F 4-SCF2Br H H H H O 3-F 4-F 4-SCF3 H H H H O 3-F 4-F 4-SOCH3 H H H H O 3-F 4-F 4-SOCH2CH=CH2 H H H H O 3-F 4-F 4-S0CH2Ｃ≡CH H H H H O 3-F 4-F 4-S0(Q4) H H H H O 3-F 4-F 4-SOCF3 ───────────────────────────────────[Table 3] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 4-OCF 3 HHHHO 3-F 4-F 4-OCH 2 CF 3 HHHHO 3-F 4-F 4-OCF 2 CF 3 HHHHO 3-F 4-F 4-OCF 2 CHF 2 HHHHO 3-F 4-F 4-OCF 2 CHCl 2 HHHHO 3-F 4-F 4-OCF 2 CHFCl HHHHO 3-F 4-F 4-OCF 2 CHFBr HHHHO 3-F 4-F 4-0CF 2 CF 2 CF 3 HHHHO 3-F 4-F 4-OCH 2 CH = CHCl HHHHO 3-F 4-F 4-OCH 2 C ≡ CBr HHHHO 3-F 4-F 4-O (Q4-2,2-Cl 2 ) HHHHO 3-F 4-F 4-SCH 3 HHHHO 3-F 4-F 4-SCH 2 CH = CH 2 HHHHO 3-F 4-F 4-SCH 2 C ≡ CH HHHHO 3-F 4-F 4-S (Q4) HHHHO 3-F 4-F 4- SCHF 2 HHHHO 3-F 4-F 4-SCF 2 Br HHHHO 3-F 4-F 4-SCF 3 HHHHO 3-F 4-F 4-SOCH 3 HHHHO 3-F 4-F 4-SOCH 2 CH = CH 2 HHHHO 3-F 4-F 4-S0CH 2 C ≡ CH HHHHO 3-F 4-F 4-S0 (Q4) HHHHO 3-F 4-F 4-SOCF 3 ──────────── ────────────────────────
【００３８】[0038]
【表４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 4-SO2CH3 H H H H O 3-F 4-F 4-SO2CH2CH=CH2 H H H H O 3-F 4-F 4-S02CH2C≡CH H H H H O 3-F 4-F 4-S02(Q4) H H H H O 3-F 4-F 4-SO2CF3 H H H H O 3-F 4-F 4-CH2OCH3 H H H H O 3-F 4-F 4-OCH2CH2OCH3 H H H H O 3-F 4-F 4-CH2OCH2CF3 H H H H O 3-F 4-F 4-OCF2CHFOCF3 H H H H O 3-F 4-F 4-CH2SCH3 H H H H O 3-F 4-F 4-OCH2CH2SCH3 H H H H O 3-F 4-F 4-CH2CO2CH3 H H H H O 3-F 4-F 4-CH2CO2CH2CF3 H H H H O 3-F 4-F 4-CH2COCH3 H H H H O 3-F 4-F 4-OCO2CH3 H H H H O 3-F 4-F 4-OCOCH3 H H H H O 3-F 4-F 4-COCH3 H H H H O 3-F 4-F 4-COCH2CH=CH2 H H H H O 3-F 4-F 4-C0CH2Ｃ≡CH H H H H O 3-F 4-F 4-CO(Q3) H H H H O 3-F 4-F 4-COCF3 H H H H O 3-F 4-F 4-CO2CH2CH3 H H H H O 3-F 4-F 4-CO2C(CH3)3 ───────────────────────────────────[Table 4] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 4-SO 2 CH 3 HHHHO 3-F 4-F 4-SO 2 CH 2 CH = CH 2 HHHHO 3-F 4-F 4-S0 2 CH 2 C ≡ CH HHHHO 3-F 4-F 4-S0 2 (Q4) HHHHO 3 -F 4-F 4-SO 2 CF 3 HHHHO 3-F 4-F 4-CH 2 OCH 3 HHHHO 3-F 4-F 4-OCH 2 CH 2 OCH 3 HHHHO 3-F 4-F 4-CH 2 OCH 2 CF 3 HHHHO 3-F 4-F 4-OCF 2 CHFOCF 3 HHHHO 3-F 4-F 4-CH 2 SCH 3 HHHHO 3-F 4-F 4-OCH 2 CH 2 SCH 3 HHHHO 3-F 4 -F 4-CH 2 CO 2 CH 3 HHHHO 3-F 4-F 4-CH 2 CO 2 CH 2 CF 3 HHHHO 3-F 4-F 4-CH 2 COCH 3 HHHHO 3-F 4-F 4-OCO 2 CH 3 HHHHO 3-F 4-F 4-OCOCH 3 HHHHO 3-F 4-F 4-COCH 3 HHHHO 3-F 4-F 4-COCH 2 CH = CH 2 HHHHO 3-F 4-F 4-C0CH 2 C ≡ CH HHHHO 3-F 4-F 4-CO (Q3) HHHHO 3-F 4-F 4-COCF 3 HHHHO 3-F 4-F 4-CO 2 CH 2 CH 3 HHHHO 3-F 4-F 4-CO 2 C (CH 3 ) 3 ───────────────────────── ─────────
【００３９】[0039]
【表５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 4-CO2CH2CF3 H H H H O 3-F 4-F 4-OCH2CO2CH3 H H H H O 3-F 4-F 4-NO2 H H H H O 3-F 4-F 4-CN H H H H O 3-F 4-F 4-OH H H H H O 3-F 4-F 4-CO2H H H H H O 3-F 4-F 4-SCN H H H H O 3-F 4-F 4-OSO2CH3 H H H H O 3-F 4-F 4-CSCH3 H H H H O 3-F 4-F 4-NH2 H H H H O 3-F 4-F 4-N(CH3)2 H H H H O 3-F 4-F 4-N(CH3)CH2CH3 H H H H O 3-F 4-F 4-N(CH3)CH2CH=CH2 H H H H O 3-F 4-F 4-N(CH3)CH2Ｃ≡CH H H H H O 3-F 4-F 4-N(CH3)CH2C6H5 H H H H O 3-F 4-F 4-CON(CH3)2 H H H H O 3-F 4-F 4-0CON(CH3)2 H H H H O 3-F 4-F 4-NHCOCH3 H H H H O 3-F 4-F 4-NHCSCH3 H H H H O 3-F 4-F 4-SO2N(CH3)2 H H H H O 3-F 4-F 4-Si(CH3)3 H H H H O 3-F 4-F 4-C6H5 H H H H O 3-F 4-F 4-(C6H4-4-Cl) ───────────────────────────────────[Table 5] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 4-CO 2 CH 2 CF 3 HHHHO 3-F 4-F 4-OCH 2 CO 2 CH 3 HHHHO 3-F 4-F 4-NO 2 HHHHO 3-F 4-F 4-CN HHHHO 3-F 4-F 4-OH HHHHO 3-F 4-F 4-CO 2 HHHHHO 3-F 4-F 4-SCN HHHHO 3-F 4-F 4-OSO 2 CH 3 HHHHO 3-F 4-F 4-CSCH 3 HHHHO 3-F 4- F 4-NH 2 HHHHO 3-F 4-F 4-N (CH 3 ) 2 HHHHO 3-F 4-F 4-N (CH 3 ) CH 2 CH 3 HHHHO 3-F 4-F 4-N (CH 3 ) CH 2 CH = CH 2 HHHHO 3-F 4-F 4-N (CH 3 ) CH 2 C ≡ CH HHHHO 3-F 4-F 4-N (CH 3 ) CH 2 C 6 H 5 HHHHO 3- F 4-F 4-CON ( CH 3) 2 HHHHO 3-F 4-F 4-0CON (CH 3) 2 HHHHO 3-F 4-F 4-NHCOCH 3 HHHHO 3-F 4-F 4-NHCSCH 3 HHHHO 3-F 4-F 4-SO 2 N (CH 3 ) 2 HHHHO 3-F 4-F 4-Si (CH 3 ) 3 HHHHO 3-F 4-F 4-C 6 H 5 HHHHO 3-F 4- F 4- (C 6 H 4 -4-Cl) ────────────────────────────────────
【００４０】[0040]
【表６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 4-OC6H5 H H H H O 3-F 4-F 4-O(C6H4-4-CF3) H H H H O 3-F 4-F 4-O(C6H4-4-OCF3) H H H H O 3-F 4-F 4-O(C6H3-2,4-F2) H H H H O 3-F 4-F 4-O(C6H3-3,5-Cl2) H H H H O 3-F 4-F 3-O(C6H4-4-CF3) H H H H O 3-F 4-F 4-S(C6H3-2-Cl-4-CF3) H H H H O 3-F 4-F 4-SO2C6H5 H H H H O 3-F 4-F 4-NH(C6H3-2-Cl-4-CF3) H H H H O 3-F 4-F 4-N(CH2CH3)(C6H4-4-Cl) H H H H O 3-F 4-F 4-CH2C6H5 H H H H O 3-F 4-F 4-CF2(C6H4-4-Br) H H H H O 3-F 4-F 4-COC6H5 H H H H O 3-F 4-F 4-OCH2(C6H4-4-CF3) H H H H O 3-F 4-F 4-CH2OC6H5 H H H H O 3-F 4-F 4-NHCH2C6H5 H H H H O 3-F 4-F 4-CH2CH2C6H5 H H H H O 3-F 4-F 4-CH=CH(C6H3-2,4-Cl2) H H H H O 3-F 4-F 4-N=NC6H5 H H H H O 3-F 4-F 4-OCH2CH2C6H5 H H H H O 3-F 4-F 4-NHCON(CH3)(C6H4-4-Cl) H H H H O 3-F 4-F 4-OCH2CH2OC6H5 H H H H O 3-F 4-F 4-NHCSNHC6H5 ──────────────────────────────────[Table 6] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 4-OC 6 H 5 HHHHO 3-F 4-F 4-O (C 6 H 4 -4-CF 3 ) HHHHO 3-F 4-F 4-O (C 6 H 4 -4-OCF 3 ) HHHHO 3-F 4-F 4-O (C 6 H 3 -2,4-F 2 ) HHHHO 3-F 4-F 4-O (C 6 H 3 -3,5-Cl 2 ) HHHHO 3-F 4-F 3-O ( C 6 H 4 -4-CF 3 ) HHHHO 3-F 4-F 4-S (C 6 H 3 -2-Cl-4-CF 3 ) HHHHO 3-F 4-F 4-SO 2 C 6 H 5 HHHHO 3-F 4-F 4-NH (C 6 H 3 -2-Cl-4-CF 3 ) HHHHO 3-F 4-F 4-N (CH 2 CH 3 ) (C 6 H 4 -4-Cl ) HHHHO 3-F 4-F 4-CH 2 C 6 H 5 HHHHO 3-F 4-F 4-CF 2 (C 6 H 4 -4-Br) HHHHO 3-F 4-F 4-COC 6 H 5 HHHHO 3-F 4-F 4-OCH 2 (C 6 H 4 -4-CF 3 ) HHHHO 3-F 4-F 4-CH 2 OC 6 H 5 HHHHO 3-F 4-F 4-NHCH 2 C 6 H 5 HHHHO 3-F 4-F 4-CH 2 CH 2 C 6 H 5 HHHHO 3-F 4-F 4-CH = CH (C 6 H 3 -2,4-Cl 2 ) HHHHO 3-F 4- F 4-N = NC 6 H 5 HHHHO 3-F 4-F 4-OCH 2 CH 2 C 6 H 5 HHHHO 3-F 4-F 4-NHCON (CH 3 ) (C 6 H 4 -4-Cl) HHHH O 3-F 4-F 4-OCH 2 CH 2 OC 6 H 5 HHHHO 3-F 4-F 4-NHCSNHC 6 H 5 ───────────────────── ──────────────
【００４１】[0041]
【表７】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 2,4-F2 H H H H O 3-F 4-F 3,5-F2 H H H H O 3-F 4-F 2,3-Cl2 H H H H O 3-F 4-F 2,4-Cl2 H H H H O 3-F 4-F 2,5-Cl2 H H H H O 3-F 4-F 2,6-Cl2 H H H H O 3-F 4-F 3,4-Cl2 H H H H O 3-F 4-F 3,5-Cl2 H H H H O 3-F 4-F 3,4-Br2 H H H H O 3-F 4-F 2,4-I2 H H H H O 3-F 4-F 2,4-(CH3)2 H H H H O 3-F 4-F 3,4-(OCH3)2 H H H H O 3-F 4-F 2-F-4-Cl H H H H O 3-F 4-F 2-F-4-Br H H H H O 3-F 4-F 2-F-4-OCH(CH3)2 H H H H O 3-F 4-F 2-F-4-OCHF2 H H H H O 3-F 4-F 2-F-4-OCF3 H H H H O 3-F 4-F 2-F-4-OCF2CHF2 H H H H O 3-F 4-F 2-F-4-OCF2CHFCl H H H H O 3-F 4-F 2-F-4-OCF2CHFCF3 H H H H O 3-F 4-F 2-F-4-OCF2CHFOCF3 H H H H O 3-F 4-F 2-F-4-SO2CF2CHFCl H H H H O 3-F 4-F 2-F-4-O(C6H4-4-Cl) ───────────────────────────────────[Table 7] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 2,4-F 2 HHHHO 3-F 4-F 3,5-F 2 HHHHO 3-F 4-F 2,3-Cl 2 HHHHO 3-F 4-F 2,4-Cl 2 HHHHO 3-F 4-F 2,5 -Cl 2 HHHHO 3-F 4-F 2,6-Cl 2 HHHHO 3-F 4-F 3,4-Cl 2 HHHHO 3-F 4-F 3,5-Cl 2 HHHHO 3-F 4-F 3 , 4-Br 2 HHHHO 3-F 4-F 2,4-I 2 HHHHO 3-F 4-F 2,4- (CH 3 ) 2 HHHHO 3-F 4-F 3,4- (OCH 3 ) 2 HHHHO 3-F 4-F 2-F-4-Cl HHHHO 3-F 4-F 2-F-4-Br HHHHO 3-F 4-F 2-F-4-OCH (CH 3 ) 2 HHHHO 3- F 4-F 2-F-4-OCHF 2 HHHHO 3-F 4-F 2-F-4-OCF 3 HHHHO 3-F 4-F 2-F-4-OCF 2 CHF 2 HHHHO 3-F 4- F 2-F-4-OCF 2 CHFCl HHHHO 3-F 4-F 2-F-4-OCF 2 CHFCF 3 HHHHO 3-F 4-F 2-F-4-OCF 2 CHFOCF 3 HHHHO 3-F 4- F 2-F-4-SO 2 CF 2 CHFCl HHHHO 3-F 4-F 2-F-4-O (C 6 H 4 -4-Cl) ────────────── ─────────────────────
【００４２】[0042]
【表８】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 2-F-4-O(Q5-3-Cl-5-CF3) H H H H O 3-F 4-F 3-F-4-O(Q5-3-Cl-5-CF3) H H H H O 3-F 4-F 2-Cl-4-CF3 H H H H O 3-F 4-F 2-Cl-4-SCF2CHF2 H H H H O 3-F 4-F 3-Cl-4-CF3 H H H H O 3-F 4-F 3-F-4-OCF3 H H H H O 3-F 4-F 3-Cl-4-OCF3 H H H H O 3-F 4-F 3-Cl-4-OCHF2 H H H H O 3-F 4-F 3-Cl-4-OCF2CHF2 H H H H O 3-F 4-F 3-Cl-4-OCF2CHFOCF3 H H H H O 3-F 4-F 3-Cl-4-SCHF2 H H H H O 3-F 4-F 3-Cl-4-CO2CH3 H H H H O 3-F 4-F 3-Cl-4-CO2CH(CH2F)2 H H H H O 3-F 4-F 3-Cl-4-O(C6H4-4-CF3) H H H H O 3-F 4-F 3-Cl-4-O(Q5-5-CF3) H H H H O 3-F 4-F 3-Cl-4-NH(Q5-5-CF3) H H H H O 3-F 4-F 3-Br-4-OCF3 H H H H O 3-F 4-F 3-CH3-4-OCF2CHF2 H H H H O 3-F 4-F 3-CF3-4-Cl H H H H O 3-F 4-F 3-CF3-4-OCF2CHF2 H H H H O 3-F 4-F 3-CF3-4-OCF2CHFBr H H H H O 3-F 4-F 3,4-(CF3)2 H H H H O 3-F 4-F 3,4-(OCF3)2 ───────────────────────────────────[Table 8] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 2-F-4 -O (Q5-3-Cl-5-CF 3 ) HHHHO 3-F 4-F 3-F-4-O (Q5-3-Cl-5-CF 3 ) HHHHO 3-F 4-F 2-Cl -4-CF 3 HHHHO 3-F 4-F 2-Cl-4-SCF 2 CHF 2 HHHHO 3-F 4-F 3-Cl-4-CF 3 HHHHO 3-F 4-F 3-F-4- OCF 3 HHHHO 3-F 4-F 3-Cl-4-OCF 3 HHHHO 3-F 4-F 3-Cl-4-OCHF 2 HHHHO 3-F 4-F 3-Cl-4-OCF 2 CHF 2 HHHHO 3-F 4-F 3-Cl-4-OCF 2 CHFOCF 3 HHHHO 3-F 4-F 3-Cl-4-SCHF 2 HHHHO 3-F 4-F 3-Cl-4-CO 2 CH 3 HHHHO 3 -F 4-F 3-Cl-4-CO 2 CH (CH 2 F) 2 HHHHO 3-F 4-F 3-Cl-4-O (C 6 H 4 -4-CF 3 ) HHHHO 3-F 4 -F 3-Cl-4-O (Q5-5-CF 3 ) HHHHO 3-F 4-F 3-Cl-4-NH (Q5-5-CF 3 ) HHHHO 3-F 4-F 3-Br- 4-OCF 3 HHHHO 3-F 4-F 3-CH 3 -4-OCF 2 CHF 2 HHHHO 3-F 4-F 3-CF 3 -4-Cl HHHHO 3-F 4-F 3-CF 3 -4 -OCF 2 CHF 2 HHHHO 3-F 4-F 3-CF 3 -4-OCF 2 CHFBr HHHHO 3-F 4-F 3,4- (CF 3 ) 2 HHHHO 3-F 4-F 3,4- ( OCF 3) 2 ─ ─────────────────────────────────
【００４３】[0043]
【表９】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 2,3-F2-4-OCF3 H H H H O 3-F 4-F 2,5-F2-4-Cl H H H H O 3-F 4-F 2,5-F2-4-Br H H H H O 3-F 4-F 2,5-F2-4-OCF3 H H H H O 3-F 4-F 3,5-F2-4-CF3 H H H H O 3-F 4-F 2,5-Cl2-4-OCF2CHF2 H H H H O 3-F 4-F 2,5-Cl2-4-O(Q5-3,5-Cl2) H H H H O 3-F 4-F 2,6-Cl2-4-CF3 H H H H O 3-F 4-F 2,3,4-F3 H H H H O 3-F 4-F 2,4,5-F3 H H H H O 3-F 4-F 2,3,4-Cl3 H H H H O 3-F 4-F 2,4,5-Cl3 H H H H O 3-F 4-F 2,4,6-Cl3 H H H H O 3-F 4-F 3,4,5-Cl3 H H H H O 3-F 4-F 2-F-4,5-Cl2 H H H H O 3-F 4-F 3,5-Cl2-4-O(Q5-5-CF3) H H H H O 3-F 4-F 3,5-Cl2-4-O(C6H4-4-CF3) H H H H O 3-F 4-F 3,5-Cl2-4-OCH2CH=CH2 H H H H O 3-F 4-F 3,5-Cl2-4-OCF2CHF2 H H H H O 3-F 4-F 3,5-Cl2-4-OCF2CHFOCF3 H H H H O 3-F 4-F 3,5-Cl2-4-SCF2CHF2 H H H H O 3-F 4-F 3,5-Cl2-4-N(CH3)CH2CH2CH3 H H H H O 3-F 4-F 3,5-Cl2-4-N(CH3)CH2C6H5 ───────────────────────────────────[Table 9] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 2,3-F 2 -4-OCF 3 HHHHO 3-F 4-F 2,5-F 2 -4-Cl HHHHO 3-F 4-F 2,5-F 2 -4-Br HHHHO 3-F 4-F 2,5 -F 2 -4-OCF 3 HHHHO 3-F 4-F 3,5-F 2 -4-CF 3 HHHHO 3-F 4-F 2,5-Cl 2 -4-OCF 2 CHF 2 HHHHO 3-F 4-F 2,5-Cl 2 -4-O (Q5-3,5-Cl 2 ) HHHHO 3-F 4-F 2,6-Cl 2 -4-CF 3 HHHHO 3-F 4-F 2, 3,4-F 3 HHHHO 3-F 4-F 2,4,5-F 3 HHHHO 3-F 4-F 2,3,4-Cl 3 HHHHO 3-F 4-F 2,4,5-Cl 3 HHHHO 3-F 4-F 2,4,6-Cl 3 HHHHO 3-F 4-F 3,4,5-Cl 3 HHHHO 3-F 4-F 2-F-4,5-Cl 2 HHHHO 3 -F 4-F 3,5-Cl 2 -4-O (Q5-5-CF 3 ) HHHHO 3-F 4-F 3,5-Cl 2 -4-O (C 6 H 4 -4-CF 3 ) HHHHO 3-F 4-F 3,5-Cl 2 -4-OCH 2 CH = CH 2 HHHHO 3-F 4-F 3,5-Cl 2 -4-OCF 2 CHF 2 HHHHO 3-F 4-F 3,5-Cl 2 -4-OCF 2 CHFOCF 3 HHHHO 3-F 4-F 3,5-Cl 2 -4-SCF 2 CHF 2 HHHHO 3-F 4-F 3,5-Cl 2 -4-N (CH 3 ) CH 2 CH 2 CH 3 HHHHO 3-F 4-F 3,5-Cl 2 -4-N (CH 3 ) CH 2 C 6 H 5 ────────────────────────────────────
【００４４】[0044]
【表１０】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-F 2-F-3-CF3-5-Cl H H H H O 3-F 4-F 2-F-4-OCF3-5-Cl H H H H O 3-F 4-F 2-F-4-OCF2CHF2-5-Cl H H H H O 3-F 4-F 2-CF3-4,6-(NO2)2 H H H H O 3-F 4-F 2,3,4,5-F4 H H H H O 3-F 4-F 2,3,5,6-F4 H H H H O 3-F 4-F 2,3,4,5-Cl4 H H H H O 3-F 4-F 2,4-F2-3,5-Cl2 H H H H O 3-F 4-F 2,6-F2-3,5-Cl2 H H H H O 3-F 4-F 2,3,5-F3-4-OCF3 H H H H O 3-F 4-F 2-F-3,5-Cl2-4-OCF2CHF2 H H H H O 3-F 4-F 2,3,4,5,6-F5 H H H H O 3-F 4-F 2,3,5,6-F4-4-CN H H H H O 3-F 4-F 2,4,6-F3-3,5-Cl2 H H H H O 3-F 4-F 3-Cl-4-F H H H H O 3-F 4-F 4-OSO2CF3 H H H H O 3-F 4-F 4-(Q1-2,2-Cl2) H H H H O 3-F 4-F 4-SO2CF2CF2CF3 H H H H O 3-F 4-F 4-SOCF2CHF2 H H H H O 3-F 4-F 4-SO2CHF2 H H H H O 3-F 4-F 3-OCF2O-4 H H H H O 3-F 4-F 3-OCH2O-4 H H H H O 3-F 4-F 3-OCF2CF2O-4 ───────────────────────────────────[Table 10] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-F 2-F-3 -CF 3 -5-Cl HHHHO 3-F 4-F 2-F-4-OCF 3 -5-Cl HHHHO 3-F 4-F 2-F-4-OCF 2 CHF 2 -5-Cl HHHHO 3- F 4-F 2-CF 3 -4,6- (NO 2 ) 2 HHHHO 3-F 4-F 2,3,4,5-F 4 HHHHO 3-F 4-F 2,3,5,6- F 4 HHHHO 3-F 4- F 2,3,4,5-Cl 4 HHHHO 3-F 4-F 2,4-F 2 -3,5-Cl 2 HHHHO 3-F 4-F 2,6- F 2 -3,5-Cl 2 HHHHO 3-F 4-F 2,3,5-F 3 -4-OCF 3 HHHHO 3-F 4-F 2-F-3,5-Cl 2 -4-OCF 2 CHF 2 HHHHO 3-F 4-F 2,3,4,5,6-F 5 HHHHO 3-F 4-F 2,3,5,6-F 4 -4-CN HHHHO 3-F 4-F 2,4,6-F 3 -3,5-Cl 2 HHHHO 3-F 4-F 3-Cl-4-FHHHHO 3-F 4-F 4-OSO 2 CF 3 HHHHO 3-F 4-F 4- (Q1-2,2-Cl 2 ) HHHHO 3-F 4-F 4-SO 2 CF 2 CF 2 CF 3 HHHHO 3-F 4-F 4-SOCF 2 CHF 2 HHHHO 3-F 4-F 4-SO 2 CHF 2 HHHHO 3-F 4-F 3-OCF 2 O-4 HHHHO 3-F 4-F 3-OCH 2 O-4 HHHHO 3-F 4-F 3-OCF 2 CF 2 O-4 ─── ────────── ──────────────────────
【００４５】[0045]
【表１１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 4-F 4-F H H H H O 3-CF3 4-F 3-Cl H H H H O 3-CF3 4-F 4-Cl H H H H O 3-CF3 4-F 4-Br H H H H O 3-CF3 4-F 4-I H H H H O 3-CF3 4-F 4-CH3 H H H H O 3-CF3 4-F 4-C(CH3)3 H H H H O 3-CF3 4-F 4-CHF2 H H H H O 3-CF3 4-F 3-CF3 H H H H O 3-CF3 4-F 4-CF3 H H H H O 3-CF3 4-F 4-OCH3 H H H H O 3-CF3 4-F 4-OCH2CH3 H H H H O 3-CF3 4-F 4-OCHF2 H H H H O 3-CF3 4-F 4-OCF2Br H H H H O 3-CF3 4-F 3-OCF3 H H H H O 3-CF3 4-F 4-OCF3 H H H H O 3-CF3 4-F 4-OCH2CF3 H H H H O 3-CF3 4-F 4-OCF2CF3 H H H H O 3-CF3 4-F 4-OCF2CHF2 H H H H O 3-CF3 4-F 4-OCF2CHFCl H H H H O 3-CF3 4-F 4-0CF2CF2CF3 H H H H O 3-CF3 4-F 4-SCH3 H H H H O 3-CF3 4-F 4-SCHF2 ───────────────────────────────────[Table 11] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 4-F 4-FHHHHO 3 -CF 3 4-F 3-Cl HHHHO 3-CF 3 4-F 4-Cl HHHHO 3-CF 3 4-F 4-Br HHHHO 3-CF 3 4-F 4-IHHHHO 3-CF 3 4-F 4 -CH 3 HHHHO 3-CF 3 4-F 4-C (CH 3 ) 3 HHHHO 3-CF 3 4-F 4-CHF 2 HHHHO 3-CF 3 4-F 3-CF 3 HHHHO 3-CF 3 4- F 4-CF 3 HHHHO 3-CF 3 4-F 4-OCH 3 HHHHO 3-CF 3 4-F 4-OCH 2 CH 3 HHHHO 3-CF 3 4-F 4-OCHF 2 HHHHO 3-CF 3 4- F 4-OCF 2 Br HHHHO 3-CF 3 4-F 3-OCF 3 HHHHO 3-CF 3 4-F 4-OCF 3 HHHHO 3-CF 3 4-F 4-OCH 2 CF 3 HHHHO 3-CF 3 4 -F 4-OCF 2 CF 3 HHHHO 3-CF 3 4-F 4-OCF 2 CHF 2 HHHHO 3-CF 3 4-F 4-OCF 2 CHFCl HHHHO 3-CF 3 4-F 4-0CF 2 CF 2 CF 3 HHHHO 3-CF 3 4-F 4-SCH 3 HHHHO 3-CF 3 4-F 4-SCHF 2 ────────────────────────── ──────────
【００４６】[0046]
【表１２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 4-F 4-SCF2Br H H H H O 3-CF3 4-F 4-SCF3 H H H H O 3-CF3 4-F 4-SOCH3 H H H H O 3-CF3 4-F 4-SOCF3 H H H H O 3-CF3 4-F 4-SO2CH3 H H H H O 3-CF3 4-F 4-SO2CF3 H H H H O 3-CF3 4-F 4-SO2CF2CHF2 H H H H O 3-CF3 4-F 4-OCO2CH3 H H H H O 3-CF3 4-F 4-OCF2CHFOCF3 H H H H O 3-CF3 4-F 4-OCOCH3 H H H H O 3-CF3 4-F 4-COCH3 H H H H O 3-CF3 4-F 4-COCF3 H H H H O 3-CF3 4-F 4-CO2CH2CH3 H H H H O 3-CF3 4-F 4-CO2CH2CF3 H H H H O 3-CF3 4-F 4-NO2 H H H H O 3-CF3 4-F 4-CN H H H H O 3-CF3 4-F 4-OH H H H H O 3-CF3 4-F 4-CO2H H H H H O 3-CF3 4-F 4-OSO2CH3 H H H H O 3-CF3 4-F 4-OSO2CF3 H H H H O 3-CF3 4-F 4-N(CH3)2 H H H H O 3-CF3 4-F 4-Si(CH3)3 H H H H O 3-CF3 4-F 4-C6H5 ───────────────────────────────────[Table 12] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 4-F 4-SCF 2 Br HHHHO 3-CF 3 4-F 4-SCF 3 HHHHO 3-CF 3 4-F 4-SOCH 3 HHHHO 3-CF 3 4-F 4-SOCF 3 HHHHO 3-CF 3 4-F 4-SO 2 CH 3 HHHHO 3-CF 3 4-F 4-SO 2 CF 3 HHHHO 3-CF 3 4-F 4-SO 2 CF 2 CHF 2 HHHHO 3-CF 3 4-F 4-OCO 2 CH 3 HHHHO 3-CF 3 4-F 4-OCF 2 CHFOCF 3 HHHHO 3-CF 3 4-F 4-OCOCH 3 HHHHO 3-CF 3 4-F 4-COCH 3 HHHHO 3-CF 3 4-F 4-COCF 3 HHHHO 3-CF 3 4-F 4-CO 2 CH 2 CH 3 HHHHO 3-CF 3 4-F 4-CO 2 CH 2 CF 3 HHHHO 3-CF 3 4-F 4-NO 2 HHHHO 3-CF 3 4-F 4-CN HHHHO 3-CF 3 4-F 4-OH HHHHO 3-CF 3 4-F 4-CO 2 HHHHHO 3-CF 3 4-F 4-OSO 2 CH 3 HHHHO 3-CF 3 4-F 4-OSO 2 CF 3 HHHHO 3-CF 3 4-F 4-N (CH 3 ) 2 HHHHO 3-CF 3 4-F 4-Si (CH 3 ) 3 HHHHO 3-CF 3 4-F 4-C 6 H 5 ─── ──────────────────────────── ────
【００４７】[0047]
【表１３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 4-F 4-OC6H5 H H H H O 3-CF3 4-F 4-O(C6H4-4-CF3) H H H H O 3-CF3 4-F 4-O(Q5-5-CF3) H H H H O 3-CF3 4-F 4-SO2C6H5 H H H H O 3-CF3 4-F 4-CH2C6H5 H H H H O 3-CF3 4-F 4-COC6H5 H H H H O 3-CF3 4-F 2,4-F2 H H H H O 3-CF3 4-F 3,4-Cl2 H H H H O 3-CF3 4-F 3,4-Br2 H H H H O 3-CF3 4-F 2-F-4-Cl H H H H O 3-CF3 4-F 2-F-4-OCF3 H H H H O 3-CF3 4-F 2-F-4-OCF2CHF2 H H H H O 3-CF3 4-F 3-Cl-4-CF3 H H H H O 3-CF3 4-F 3-F-4-OCF3 H H H H O 3-CF3 4-F 2-F-4-OCF2CHF2 H H H H O 3-CF3 4-F 3-Cl-4-OCF2CHFOCF3 H H H H O 3-CF3 4-F 3-Cl-4-SCHF2 H H H H O 3-CF3 4-F 2,5-F2-4-OCF3 H H H H O 3-CF3 4-F 2-F-4,5-Cl2 H H H H O 3-CF3 4-F 3,5-Cl2-4-OCF2CHF2 H H H H O 3-CF3 4-F 3,4,5-Cl3 H H H H O 3-CF3 4-F 2-F-4-OCF2CHF2-5-Cl H H H H O 3-CF3 4-F 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 13] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 4-F 4-OC 6 H 5 HHHHO 3-CF 3 4-F 4-O (C 6 H 4 -4-CF 3 ) HHHHO 3-CF 3 4-F 4-O (Q5-5-CF 3 ) HHHHO 3-CF 3 4- F 4-SO 2 C 6 H 5 HHHHO 3-CF 3 4-F 4-CH 2 C 6 H 5 HHHHO 3-CF 3 4-F 4-COC 6 H 5 HHHHO 3-CF 3 4-F 2,4 -F 2 HHHHO 3-CF 3 4-F 3,4-Cl 2 HHHHO 3-CF 3 4-F 3,4-Br 2 HHHHO 3-CF 3 4-F 2-F-4-Cl HHHHO 3-CF 3 4-F 2-F-4-OCF 3 HHHHO 3-CF 3 4-F 2-F-4-OCF 2 CHF 2 HHHHO 3-CF 3 4-F 3-Cl-4-CF 3 HHHHO 3-CF 3 4-F 3-F-4-OCF 3 HHHHO 3-CF 3 4-F 2-F-4-OCF 2 CHF 2 HHHHO 3-CF 3 4-F 3-Cl-4-OCF 2 CHFOCF 3 HHHHO 3 -CF 3 4-F 3-Cl-4-SCHF 2 HHHHO 3-CF 3 4-F 2,5-F 2 -4-OCF 3 HHHHO 3-CF 3 4-F 2-F-4,5-Cl 2 HHHHO 3-CF 3 4-F 3,5-Cl 2 -4-OCF 2 CHF 2 HHHHO 3-CF 3 4-F 3,4,5-Cl 3 HHHHO 3-CF 3 4-F 2-F- 4-OCF 2 CHF 2 -5- Cl HHHHO 3-CF 3 4-F 2,4-F 2 -3,5-Cl 2 ─── ───────────────────────────────
【００４８】[0048]
【表１４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-Cl 4-F 4-Cl H H H H O 3-Cl 4-F 4-Br H H H H O 3-Cl 4-F 4-CF3 H H H H O 3-Cl 4-F 4-OCH2CH3 H H H H O 3-Cl 4-F 4-OCHF2 H H H H O 3-Cl 4-F 4-OCF2Br H H H H O 3-Cl 4-F 4-OCF2CHF2 H H H H O 3-Cl 4-F 4-OCF3 H H H H O 3-Cl 4-F 4-SCHF2 H H H H O 3-Cl 4-F 4-SCF2Br H H H H O 3-Cl 4-F 4-SCF3 H H H H O 3-Cl 4-F 4-O(Q6-6-Cl) H H H H O 3-Cl 4-F 4-O(Q7) H H H H O 3-Cl 4-F 4-O(Q5-5-CF3) H H H H O 3-Cl 4-F 4-OCF2CHFOCF3 H H H H O 3-Cl 4-F 4-COCF3 H H H H O 3-Cl 4-F 4-CO2CH2CH3 H H H H O 3-Cl 4-F 4-NO2 H H H H O 3-Cl 4-F 4-CN H H H H O 3-Cl 4-F 4-OSO2CF3 H H H H O 3-Cl 4-F 3,4-Cl2 H H H H O 3-Cl 4-F 3-Cl-4-OCF2CHF2 H H H H O 3-Cl 4-F 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 14] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-Cl 4-F 4-Cl HHHHO 3 -Cl 4-F 4-Br HHHHO 3-Cl 4-F 4-CF 3 HHHHO 3-Cl 4-F 4-OCH 2 CH 3 HHHHO 3-Cl 4-F 4-OCHF 2 HHHHO 3-Cl 4-F 4-OCF 2 Br HHHHO 3-Cl 4-F 4-OCF 2 CHF 2 HHHHO 3-Cl 4-F 4-OCF 3 HHHHO 3-Cl 4-F 4-SCHF 2 HHHHO 3-Cl 4-F 4-SCF 2 Br HHHHO 3-Cl 4-F 4-SCF 3 HHHHO 3-Cl 4-F 4-O (Q6-6-Cl) HHHHO 3-Cl 4-F 4-O (Q7) HHHHO 3-Cl 4-F 4-O (Q5-5-CF 3 ) HHHHO 3-Cl 4-F 4-OCF 2 CHFOCF 3 HHHHO 3-Cl 4-F 4-COCF 3 HHHHO 3-Cl 4-F 4-CO 2 CH 2 CH 3 HHHHO 3-Cl 4-F 4-NO 2 HHHHO 3-Cl 4-F 4-CN HHHHO 3-Cl 4-F 4-OSO 2 CF 3 HHHHO 3-Cl 4-F 3,4-Cl 2 HHHHO 3- Cl 4-F 3-Cl-4-OCF 2 CHF 2 HHHHO 3-Cl 4-F 2,4-F 2 -3,5-Cl 2 ───────────────── ────────────────────
【００４９】[0049]
【表１５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-Cl 3-Cl 4-Cl H H H H O 3-Cl 3-Cl 4-Br H H H H O 3-Cl 3-Cl 4-CF3 H H H H O 3-Cl 3-Cl 4-OCH2CH3 H H H H O 3-Cl 3-Cl 4-OCHF2 H H H H O 3-Cl 3-Cl 4-OCF2Br H H H H O 3-Cl 3-Cl 4-OCF2CHF2 H H H H O 3-Cl 3-Cl 4-OCF3 H H H H O 3-Cl 3-Cl 4-SCHF2 H H H H O 3-Cl 3-Cl 4-SCF2Br H H H H O 3-Cl 3-Cl 4-SCF3 H H H H O 3-Cl 3-Cl 4-O(Q6-6-Cl) H H H H O 3-Cl 3-Cl 4-O(Q7) H H H H O 3-Cl 3-Cl 4-O(Q5-5-CF3) H H H H O 3-Cl 3-Cl 4-OCF2CHFOCF3 H H H H O 3-Cl 3-Cl 4-COCF3 H H H H O 3-Cl 3-Cl 4-CO2CH2CH3 H H H H O 3-Cl 3-Cl 4-NO2 H H H H O 3-Cl 3-Cl 4-CN H H H H O 3-Cl 3-Cl 4-OSO2CF3 H H H H O 3-Cl 3-Cl 3,4-Cl2 H H H H O 3-Cl 3-Cl 3-Cl-4-OCF2CHF2 H H H H O 3-Cl 3-Cl 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 15] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-Cl 3-Cl 4-Cl HHHHO 3 -Cl 3-Cl 4-Br HHHHO 3-Cl 3-Cl 4-CF 3 HHHHO 3-Cl 3-Cl 4-OCH 2 CH 3 HHHHO 3-Cl 3-Cl 4-OCHF 2 HHHHO 3-Cl 3-Cl 4-OCF 2 Br HHHHO 3-Cl 3-Cl 4-OCF 2 CHF 2 HHHHO 3-Cl 3-Cl 4-OCF 3 HHHHO 3-Cl 3-Cl 4-SCHF 2 HHHHO 3-Cl 3-Cl 4-SCF 2 Br HHHHO 3-Cl 3-Cl 4-SCF 3 HHHHO 3-Cl 3-Cl 4-O (Q6-6-Cl) HHHHO 3-Cl 3-Cl 4-O (Q7) HHHHO 3-Cl 3-Cl 4-O (Q5-5-CF 3 ) HHHHO 3-Cl 3-Cl 4-OCF 2 CHFOCF 3 HHHHO 3-Cl 3-Cl 4-COCF 3 HHHHO 3-Cl 3-Cl 4-CO 2 CH 2 CH 3 HHHHO 3-Cl 3-Cl 4-NO 2 HHHHO 3-Cl 3-Cl 4-CN HHHHO 3-Cl 3-Cl 4-OSO 2 CF 3 HHHHO 3-Cl 3-Cl 3,4-Cl 2 HHHHO 3- Cl 3-Cl 3-Cl-4-OCF 2 CHF 2 HHHHO 3-Cl 3-Cl 2,4-F 2 -3,5-Cl 2 ───────────────── ────────────────────
【００５０】[0050]
【表１６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-Cl 3-F 4-Cl H H H H O 3-Cl 3-F 4-Br H H H H O 3-Cl 3-F 4-CF3 H H H H O 3-Cl 3-F 4-OCH2CH3 H H H H O 3-Cl 3-F 4-OCHF2 H H H H O 3-Cl 3-F 4-OCF2Br H H H H O 3-Cl 3-F 4-OCF2CHF2 H H H H O 3-Cl 3-F 4-OCF3 H H H H O 3-Cl 3-F 4-SCHF2 H H H H O 3-Cl 3-F 4-SCF2Br H H H H O 3-Cl 3-F 4-SCF3 H H H H O 3-Cl 3-F 4-O(Q6-6-Cl) H H H H O 3-Cl 3-F 4-O(Q7) H H H H O 3-Cl 3-F 4-O(Q5-5-CF3) H H H H O 3-Cl 3-F 4-OCF2CHFOCF3 H H H H O 3-Cl 3-F 4-COCF3 H H H H O 3-Cl 3-F 4-CO2CH2CH3 H H H H O 3-Cl 3-F 4-NO2 H H H H O 3-Cl 3-F 4-CN H H H H O 3-Cl 3-F 4-OSO2CF3 H H H H O 3-Cl 3-F 3,4-Cl2 H H H H O 3-Cl 3-F 3-Cl-4-OCF2CHF2 H H H H O 3-Cl 3-F 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 16] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-Cl 3-F 4-Cl HHHHO 3 -Cl 3-F 4-Br HHHHO 3-Cl 3-F 4-CF 3 HHHHO 3-Cl 3-F 4-OCH 2 CH 3 HHHHO 3-Cl 3-F 4-OCHF 2 HHHHO 3-Cl 3-F 4-OCF 2 Br HHHHO 3-Cl 3-F 4-OCF 2 CHF 2 HHHHO 3-Cl 3-F 4-OCF 3 HHHHO 3-Cl 3-F 4-SCHF 2 HHHHO 3-Cl 3-F 4-SCF 2 Br HHHHO 3-Cl 3-F 4-SCF 3 HHHHO 3-Cl 3-F 4-O (Q6-6-Cl) HHHHO 3-Cl 3-F 4-O (Q7) HHHHO 3-Cl 3-F 4-O (Q5-5-CF 3 ) HHHHO 3-Cl 3-F 4-OCF 2 CHFOCF 3 HHHHO 3-Cl 3-F 4-COCF 3 HHHHO 3-Cl 3-F 4-CO 2 CH 2 CH 3 HHHHO 3-Cl 3-F 4-NO 2 HHHHO 3-Cl 3-F 4-CN HHHHO 3-Cl 3-F 4-OSO 2 CF 3 HHHHO 3-Cl 3-F 3,4-Cl 2 HHHHO 3- Cl 3-F 3-Cl-4-OCF 2 CHF 2 HHHHO 3-Cl 3-F 2,4-F 2 -3,5-Cl 2 ───────────────── ────────────────────
【００５１】[0051]
【表１７】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 3-Cl 4-Cl H H H H O 3-F 3-Cl 4-Br H H H H O 3-F 3-Cl 4-CF3 H H H H O 3-F 3-Cl 4-OCH2CH3 H H H H O 3-F 3-Cl 4-OCHF2 H H H H O 3-F 3-Cl 4-OCF2Br H H H H O 3-F 3-Cl 4-OCF2CHF2 H H H H O 3-F 3-Cl 4-OCF3 H H H H O 3-F 3-Cl 4-SCHF2 H H H H O 3-F 3-Cl 4-SCF2Br H H H H O 3-F 3-Cl 4-SCF3 H H H H O 3-F 3-Cl 4-O(Q6-6-Cl) H H H H O 3-F 3-Cl 4-O(Q7) H H H H O 3-F 3-Cl 4-O(Q5-5-CF3) H H H H O 3-F 3-Cl 4-OCF2CHFOCF3 H H H H O 3-F 3-Cl 4-COCF3 H H H H O 3-F 3-Cl 4-CO2CH2CH3 H H H H O 3-F 3-Cl 4-NO2 H H H H O 3-F 3-Cl 4-CN H H H H O 3-F 3-Cl 4-OSO2CF3 H H H H O 3-F 3-Cl 3,4-Cl2 H H H H O 3-F 3-Cl 3-Cl-4-OCF2CHF2 H H H H O 3-F 3-Cl 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 17] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 3-Cl 4-Cl HHHHO 3 -F 3-Cl 4-Br HHHHO 3-F 3-Cl 4-CF 3 HHHHO 3-F 3-Cl 4-OCH 2 CH 3 HHHHO 3-F 3-Cl 4-OCHF 2 HHHHO 3-F 3-Cl 4-OCF 2 Br HHHHO 3-F 3-Cl 4-OCF 2 CHF 2 HHHHO 3-F 3-Cl 4-OCF 3 HHHHO 3-F 3-Cl 4-SCHF 2 HHHHO 3-F 3-Cl 4-SCF 2 Br HHHHO 3-F 3-Cl 4-SCF 3 HHHHO 3-F 3-Cl 4-O (Q6-6-Cl) HHHHO 3-F 3-Cl 4-O (Q7) HHHHO 3-F 3-Cl 4-O (Q5-5-CF 3 ) HHHHO 3-F 3-Cl 4-OCF 2 CHFOCF 3 HHHHO 3-F 3-Cl 4-COCF 3 HHHHO 3-F 3-Cl 4-CO 2 CH 2 CH 3 HHHHO 3-F 3-Cl 4-NO 2 HHHHO 3-F 3-Cl 4-CN HHHHO 3-F 3-Cl 4-OSO 2 CF 3 HHHHO 3-F 3-Cl 3,4-Cl 2 HHHHO 3- F 3-Cl 3-Cl-4-OCF 2 CHF 2 HHHHO 3-F 3-Cl 2,4-F 2 -3,5-Cl 2 ───────────────── ────────────────────
【００５２】[0052]
【表１８】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 3-F 4-Cl H H H H O 3-F 3-F 4-Br H H H H O 3-F 3-F 4-CF3 H H H H O 3-F 3-F 4-OCH2CH3 H H H H O 3-F 3-F 4-OCHF2 H H H H O 3-F 3-F 4-OCF2Br H H H H O 3-F 3-F 4-OCF2CHF2 H H H H O 3-F 3-F 4-OCF3 H H H H O 3-F 3-F 4-SCHF2 H H H H O 3-F 3-F 4-SCF2Br H H H H O 3-F 3-F 4-SCF3 H H H H O 3-F 3-F 4-O(Q6-6-Cl) H H H H O 3-F 3-F 4-O(Q7) H H H H O 3-F 3-F 4-O(Q5-5-CF3) H H H H O 3-F 3-F 4-OCF2CHFOCF3 H H H H O 3-F 3-F 4-COCF3 H H H H O 3-F 3-F 4-CO2CH2CH3 H H H H O 3-F 3-F 4-NO2 H H H H O 3-F 3-F 4-CN H H H H O 3-F 3-F 4-OSO2CF3 H H H H O 3-F 3-F 3,4-Cl2 H H H H O 3-F 3-F 3-Cl-4-OCF2CHF2 H H H H O 3-F 3-F 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 18] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 3-F 4-Cl HHHHO 3 -F 3-F 4-Br HHHHO 3-F 3-F 4-CF 3 HHHHO 3-F 3-F 4-OCH 2 CH 3 HHHHO 3-F 3-F 4-OCHF 2 HHHHO 3-F 3-F 4-OCF 2 Br HHHHO 3-F 3-F 4-OCF 2 CHF 2 HHHHO 3-F 3-F 4-OCF 3 HHHHO 3-F 3-F 4-SCHF 2 HHHHO 3-F 3-F 4-SCF 2 Br HHHHO 3-F 3-F 4-SCF 3 HHHHO 3-F 3-F 4-O (Q6-6-Cl) HHHHO 3-F 3-F 4-O (Q7) HHHHO 3-F 3-F 4-O (Q5-5-CF 3 ) HHHHO 3-F 3-F 4-OCF 2 CHFOCF 3 HHHHO 3-F 3-F 4-COCF 3 HHHHO 3-F 3-F 4-CO 2 CH 2 CH 3 HHHHO 3-F 3-F 4-NO 2 HHHHO 3-F 3-F 4-CN HHHHO 3-F 3-F 4-OSO 2 CF 3 HHHHO 3-F 3-F 3,4-Cl 2 HHHHO 3- F 3-F 3-Cl-4-OCF 2 CHF 2 HHHHO 3-F 3-F 2,4-F 2 -3,5-Cl 2 ───────────────── ────────────────────
【００５３】[0053]
【表１９】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-Cl 3-CF3 4-Cl H H H H O 3-Cl 3-CF3 4-Br H H H H O 3-Cl 3-CF3 4-CF3 H H H H O 3-Cl 3-CF3 4-OCH2CH3 H H H H O 3-Cl 3-CF3 4-OCHF2 H H H H O 3-Cl 3-CF3 4-OCF2Br H H H H O 3-Cl 3-CF3 4-OCF2CHF2 H H H H O 3-Cl 3-CF3 4-OCF3 H H H H O 3-Cl 3-CF3 4-SCHF2 H H H H O 3-Cl 3-CF3 4-SCF2Br H H H H O 3-Cl 3-CF3 4-SCF3 H H H H O 3-Cl 3-CF3 4-O(Q6-6-Cl) H H H H O 3-Cl 3-CF3 4-O(Q7) H H H H O 3-Cl 3-CF3 4-O(Q5-5-CF3) H H H H O 3-Cl 3-CF3 4-OCF2CHFOCF3 H H H H O 3-Cl 3-CF3 4-COCF3 H H H H O 3-Cl 3-CF3 4-CO2CH2CH3 H H H H O 3-Cl 3-CF3 4-NO2 H H H H O 3-Cl 3-CF3 4-CN H H H H O 3-Cl 3-CF3 4-OSO2CF3 H H H H O 3-Cl 3-CF3 3,4-Cl2 H H H H O 3-Cl 3-CF3 3-Cl-4-OCF2CHF2 H H H H O 3-Cl 3-CF3 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 19] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-Cl 3-CF 3 4-Cl HHHHO 3-Cl 3-CF 3 4-Br HHHHO 3-Cl 3-CF 3 4-CF 3 HHHHO 3-Cl 3-CF 3 4-OCH 2 CH 3 HHHHO 3-Cl 3-CF 3 4-OCHF 2 HHHHO 3 -Cl 3-CF 3 4-OCF 2 Br HHHHO 3-Cl 3-CF 3 4-OCF 2 CHF 2 HHHHO 3-Cl 3-CF 3 4-OCF 3 HHHHO 3-Cl 3-CF 3 4-SCHF 2 HHHHO 3-Cl 3-CF 3 4-SCF 2 Br HHHHO 3-Cl 3-CF 3 4-SCF 3 HHHHO 3-Cl 3-CF 3 4-O (Q6-6-Cl) HHHHO 3-Cl 3-CF 3 4-O (Q7) HHHHO 3-Cl 3-CF 3 4-O (Q5-5-CF 3 ) HHHHO 3-Cl 3-CF 3 4-OCF 2 CHFOCF 3 HHHHO 3-Cl 3-CF 3 4-COCF 3 HHHHO 3-Cl 3-CF 3 4-CO 2 CH 2 CH 3 HHHHO 3-Cl 3-CF 3 4-NO 2 HHHHO 3-Cl 3-CF 3 4-CN HHHHO 3-Cl 3-CF 3 4- OSO 2 CF 3 HHHHO 3-Cl 3-CF 3 3,4-Cl 2 HHHHO 3-Cl 3-CF 3 3-Cl-4-OCF 2 CHF 2 HHHHO 3-Cl 3-CF 3 2,4-F 2 -3,5-Cl 2 ────────────────────────── ─────────
【００５４】[0054]
【表２０】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 3-Cl 4-Cl H H H H O 3-CF3 3-Cl 4-Br H H H H O 3-CF3 3-Cl 4-CF3 H H H H O 3-CF3 3-Cl 4-OCH2CH3 H H H H O 3-CF3 3-Cl 4-OCHF2 H H H H O 3-CF3 3-Cl 4-OCF2Br H H H H O 3-CF3 3-Cl 4-OCF2CHF2 H H H H O 3-CF3 3-Cl 4-OCF3 H H H H O 3-CF3 3-Cl 4-SCHF2 H H H H O 3-CF3 3-Cl 4-SCF2Br H H H H O 3-CF3 3-Cl 4-SCF3 H H H H O 3-CF3 3-Cl 4-O(Q6-6-Cl) H H H H O 3-CF3 3-Cl 4-O(Q7) H H H H O 3-CF3 3-Cl 4-O(Q5-5-CF3) H H H H O 3-CF3 3-Cl 4-OCF2CHFOCF3 H H H H O 3-CF3 3-Cl 4-COCF3 H H H H O 3-CF3 3-Cl 4-CO2CH2CH3 H H H H O 3-CF3 3-Cl 4-NO2 H H H H O 3-CF3 3-Cl 4-CN H H H H O 3-CF3 3-Cl 4-OSO2CF3 H H H H O 3-CF3 3-Cl 3,4-Cl2 H H H H O 3-CF3 3-Cl 3-Cl-4-OCF2CHF2 H H H H O 3-CF3 3-Cl 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 20] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 3-Cl 4-Cl HHHHO 3-CF 3 3-Cl 4-Br HHHHO 3-CF 3 3-Cl 4-CF 3 HHHHO 3-CF 3 3-Cl 4-OCH 2 CH 3 HHHHO 3-CF 3 3-Cl 4-OCHF 2 HHHHO 3 -CF 3 3-Cl 4-OCF 2 Br HHHHO 3-CF 3 3-Cl 4-OCF 2 CHF 2 HHHHO 3-CF 3 3-Cl 4-OCF 3 HHHHO 3-CF 3 3-Cl 4-SCHF 2 HHHHO 3-CF 3 3-Cl 4-SCF 2 Br HHHHO 3-CF 3 3-Cl 4-SCF 3 HHHHO 3-CF 3 3-Cl 4-O (Q6-6-Cl) HHHHO 3-CF 3 3-Cl 4-O (Q7) HHHHO 3-CF 3 3-Cl 4-O (Q5-5-CF 3 ) HHHHO 3-CF 3 3-Cl 4-OCF 2 CHFOCF 3 HHHHO 3-CF 3 3-Cl 4-COCF 3 HHHHO 3-CF 3 3-Cl 4-CO 2 CH 2 CH 3 HHHHO 3-CF 3 3-Cl 4-NO 2 HHHHO 3-CF 3 3-Cl 4-CN HHHHO 3-CF 3 3-Cl 4- OSO 2 CF 3 HHHHO 3-CF 3 3-Cl 3,4-Cl 2 HHHHO 3-CF 3 3-Cl 3-Cl-4-OCF 2 CHF 2 HHHHO 3-CF 3 3-Cl 2,4-F 2 -3,5-Cl 2 ────────────────────────── ─────────
【００５５】[0055]
【表２１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 3-F 4-Cl H H H H O 3-CF3 3-F 4-Br H H H H O 3-CF3 3-F 4-CF3 H H H H O 3-CF3 3-F 4-OCH2CH3 H H H H O 3-CF3 3-F 4-OCHF2 H H H H O 3-CF3 3-F 4-OCF2Br H H H H O 3-CF3 3-F 4-OCF2CHF2 H H H H O 3-CF3 3-F 4-OCF3 H H H H O 3-CF3 3-F 4-SCHF2 H H H H O 3-CF3 3-F 4-SCF2Br H H H H O 3-CF3 3-F 4-SCF3 H H H H O 3-CF3 3-F 4-O(Q6-6-Cl) H H H H O 3-CF3 3-F 4-O(Q7) H H H H O 3-CF3 3-F 4-O(Q5-5-CF3) H H H H O 3-CF3 3-F 4-OCF2CHFOCF3 H H H H O 3-CF3 3-F 4-COCF3 H H H H O 3-CF3 3-F 4-CO2CH2CH3 H H H H O 3-CF3 3-F 4-NO2 H H H H O 3-CF3 3-F 4-CN H H H H O 3-CF3 3-F 4-OSO2CF3 H H H H O 3-CF3 3-F 3,4-Cl2 H H H H O 3-CF3 3-F 3-Cl-4-OCF2CHF2 H H H H O 3-CF3 3-F 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 21] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 3-F 4-Cl HHHHO 3-CF 3 3-F 4-Br HHHHO 3-CF 3 3-F 4-CF 3 HHHHO 3-CF 3 3-F 4-OCH 2 CH 3 HHHHO 3-CF 3 3-F 4-OCHF 2 HHHHO 3 -CF 3 3-F 4-OCF 2 Br HHHHO 3-CF 3 3-F 4-OCF 2 CHF 2 HHHHO 3-CF 3 3-F 4-OCF 3 HHHHO 3-CF 3 3-F 4-SCHF 2 HHHHO 3-CF 3 3-F 4-SCF 2 Br HHHHO 3-CF 3 3-F 4-SCF 3 HHHHO 3-CF 3 3-F 4-O (Q6-6-Cl) HHHHO 3-CF 3 3-F 4-O (Q7) HHHHO 3-CF 3 3-F 4-O (Q5-5-CF 3 ) HHHHO 3-CF 3 3-F 4-OCF 2 CHFOCF 3 HHHHO 3-CF 3 3-F 4-COCF 3 HHHHO 3-CF 3 3-F 4-CO 2 CH 2 CH 3 HHHHO 3-CF 3 3-F 4-NO 2 HHHHO 3-CF 3 3-F 4-CN HHHHO 3-CF 3 3-F 4- OSO 2 CF 3 HHHHO 3-CF 3 3-F 3,4-Cl 2 HHHHO 3-CF 3 3-F 3-Cl-4-OCF 2 CHF 2 HHHHO 3-CF 3 3-F 2,4-F 2 -3,5-Cl 2 ───────────────────────────────── ─
【００５６】[0056]
【表２２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O H 3-CF3 4-Cl H H H H O H 3-CF3 4-Br H H H H O H 3-CF3 4-CF3 H H H H O H 3-CF3 4-OCH2CH3 H H H H O H 3-CF3 4-OCHF2 H H H H O H 3-CF3 4-OCF2Br H H H H O H 3-CF3 4-OCF2CHF2 H H H H O H 3-CF3 4-OCF3 H H H H O H 3-CF3 4-SCHF2 H H H H O H 3-CF3 4-SCF2Br H H H H O H 3-CF3 4-SCF3 H H H H O H 3-CF3 4-O(Q6-6-Cl) H H H H O H 3-CF3 4-O(Q7) H H H H O H 3-CF3 4-O(Q5-5-CF3) H H H H O H 3-CF3 4-OCF2CHFOCF3 H H H H O H 3-CF3 4-COCF3 H H H H O H 3-CF3 4-CO2CH2CH3 H H H H O H 3-CF3 4-NO2 H H H H O H 3-CF3 4-CN H H H H O H 3-CF3 4-OSO2CF3 H H H H O H 3-CF3 3,4-Cl2 H H H H O H 3-CF3 3-Cl-4-OCF2CHF2 H H H H O H 3-CF3 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 22] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHOH 3-CF 3 4-Cl HHHHOH 3-CF 3 4-Br HHHHOH 3-CF 3 4-CF 3 HHHHOH 3-CF 3 4-OCH 2 CH 3 HHHHOH 3-CF 3 4-OCHF 2 HHHHOH 3-CF 3 4-OCF 2 Br HHHHOH 3-CF 3 4- OCF 2 CHF 2 HHHHOH 3-CF 3 4-OCF 3 HHHHOH 3-CF 3 4-SCHF 2 HHHHOH 3-CF 3 4-SCF 2 Br HHHHOH 3-CF 3 4-SCF 3 HHHHOH 3-CF 3 4-O ( Q6-6-Cl) HHHHOH 3-CF 3 4-O (Q7) HHHHOH 3-CF 3 4-O (Q5-5-CF 3 ) HHHHOH 3-CF 3 4-OCF 2 CHFOCF 3 HHHHOH 3-CF 3 4 -COCF 3 HHHHOH 3-CF 3 4-CO 2 CH 2 CH 3 HHHHOH 3-CF 3 4-NO 2 HHHHOH 3-CF 3 4-CN HHHHOH 3-CF 3 4-OSO 2 CF 3 HHHHOH 3-CF 3 3 , 4-Cl 2 HHHHOH 3-CF 3 3-Cl-4-OCF 2 CHF 2 HHHHOH 3-CF 3 2,4-F 2 -3,5-Cl 2 ───────────── ───────────────────────
【００５７】[0057]
【表２３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O H H 4-Cl H H H H O H H 4-Br H H H H O H H 4-CF3 H H H H O H H 4-OCHF2 H H H H O H H 4-OCF2Br H H H H O H H 4-OCF2CHF2 H H H H O H H 4-OCF3 H H H H O H H 4-SCF3 H H H H O H H 4-OSO2CF3 H H H H O H H 3,4-Cl2 H H H H O H 4-F 4-Cl H H H H O H 4-F 4-Br H H H H O H 4-F 4-CF3 H H H H O H 4-F 4-OCHF2 H H H H O H 4-F 4-OCF2Br H H H H O H 4-F 4-OCF2CHF2 H H H H O H 4-F 4-OCF3 H H H H O H 4-F 4-SCF3 H H H H O H 4-F 4-OSO2CF3 H H H H O H 4-F 3,4-Cl2 H H H H O H 4-CN 4-Cl H H H H O H 4-CN 4-Br H H H H O H 4-CN 4-CF3 ───────────────────────────────────[Table 23] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHOHH 4-Cl HHHHOHH 4-Br HHHHOHH 4-CF 3 HHHHOHH 4-OCHF 2 HHHHOHH 4-OCF 2 Br HHHHOHH 4-OCF 2 CHF 2 HHHHOHH 4-OCF 3 HHHHOHOH 4-SCF 3 HHHHOHH 4-OSO 2 CF 3 HHHHOHH 3,4-Cl 2 HHHHOH 4-F 4-Cl HHHHOH 4-F 4-Br HHHHOH 4-F 4-CF 3 HHHHOH 4-F 4-OCHF 2 HHHHOH 4-F 4-OCF 2 Br HHHHOH 4-F 4-OCF 2 CHF 2 HHHHOH 4-F 4-OCF 3 HHHHOH 4-F 4-SCF 3 HHHHOH 4-F 4-OSO 2 CF 3 HHHHOH 4-F 3,4-Cl 2 HHHHOH 4-CN 4-Cl HHHHOH 4-CN 4-Br HHHHOH 4-CN 4-CF 3 ───────────────────────────────────
【００５８】[0058]
【表２４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O H 4-CN 4-OCHF2 H H H H O H 4-CN 4-OCF2Br H H H H O H 4-CN 4-OCF2CHF2 H H H H O H 4-CN 4-OCF3 H H H H O H 4-CN 4-SCF3 H H H H O H 4-CN 4-OSO2CF3 H H H H O H 4-CN 3,4-Cl2 H H H H O H 4-Cl 4-Cl H H H H O H 4-Cl 4-Br H H H H O H 4-Cl 4-CF3 H H H H O H 4-Cl 4-OCHF2 H H H H O H 4-Cl 4-OCF2Br H H H H O H 4-Cl 4-OCF2CHF2 H H H H O H 4-Cl 4-OCF3 H H H H O H 4-Cl 4-SCF3 H H H H O H 4-Cl 4-OSO2CF3 H H H H O H 4-Cl 3,4-Cl2 H H H H O H 4-CF3 4-Cl H H H H O H 4-CF3 4-Br H H H H O H 4-CF3 4-CF3 H H H H O H 4-CF3 4-OCHF2 H H H H O H 4-CF3 4-OCF2Br H H H H O H 4-CF3 4-OCF2CHF2 ───────────────────────────────────[Table 24] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHOH 4-CN 4-OCHF 2 HHHHOH 4-CN 4-OCF 2 Br HHHHOH 4-CN 4-OCF 2 CHF 2 HHHHOH 4-CN 4-OCF 3 HHHHOH 4-CN 4-SCF 3 HHHHOH 4-CN 4-OSO 2 CF 3 HHHHOH 4-CN 3,4-Cl 2 HHHHOH 4-Cl 4-Cl HHHHOH 4-Cl 4-Br HHHHOH 4-Cl 4-CF 3 HHHHOH 4-Cl 4-OCHF 2 HHHHOH 4-Cl 4-OCF 2 Br HHHHOH 4-Cl 4-OCF 2 CHF 2 HHHHOH 4-Cl 4-OCF 3 HHHHOH 4-Cl 4-SCF 3 HHHHOH 4-Cl 4-OSO 2 CF 3 HHHHOH 4-Cl 3,4-Cl 2 HHHHOH 4-CF 3 4-Cl HHHHOH 4-CF 3 4 -Br HHHHOH 4-CF 3 4-CF 3 HHHHOH 4-CF 3 4-OCHF 2 HHHHOH 4-CF 3 4-OCF 2 Br HHHHOHOH 4-CF 3 4-OCF 2 CHF 2 ────────── ──────────────────────────
【００５９】[0059]
【表２５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O H 4-CF3 4-OCF3 H H H H O H 4-CF3 4-SCF3 H H H H O H 4-CF3 4-OSO2CF3 H H H H O H 4-CF3 3,4-Cl2 H H H H O H 4-OSO2CF3 4-Cl H H H H O H 4-OSO2CF3 4-Br H H H H O H 4-OSO2CF3 4-CF3 H H H H O H 4-OSO2CF3 4-OCHF2 H H H H O H 4-OSO2CF3 4-OCF2Br H H H H O 3-F 4-OSO2CF3 4-OCF2CHF2 H H H H O 3-F 4-OSO2CF3 4-OCF3 H H H H O 3-F 4-OSO2CF3 4-SCF3 H H H H O 3-F 4-OSO2CF3 4-OSO2CF3 H H H H O 3-F 4-OSO2CF3 3,4-Cl2 H H H H O 3-F 4-Cl 4-Cl H H H H O 3-F 4-Cl 4-Br H H H H O 3-F 4-Cl 4-CF3 H H H H O 3-F 4-Cl 4-OCHF2 H H H H O 3-F 4-Cl 4-OCF2Br H H H H O 3-F 4-Cl 4-OCF2CHF2 H H H H O 3-F 4-Cl 4-OCF3 H H H H O 3-F 4-Cl 4-SCF3 H H H H O 3-F 4-Cl 4-OSO2CF3 ───────────────────────────────────[Table 25] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHOH 4-CF 3 4-OCF 3 HHHHOH 4- CF 3 4-SCF 3 HHHHOH 4-CF 3 4-OSO 2 CF 3 HHHHOH 4-CF 3 3,4-Cl 2 HHHHOH 4-OSO 2 CF 3 4-Cl HHHHOH 4-OSO 2 CF 3 4-Br HHHHOH 4 -OSO 2 CF 3 4-CF 3 HHHHOH 4-OSO 2 CF 3 4-OCHF 2 HHHHOH 4-OSO 2 CF 3 4-OCF 2 Br HHHHO 3-F 4-OSO 2 CF 3 4-OCF 2 CHF 2 HHHHO 3 -F 4-OSO 2 CF 3 4-OCF 3 HHHHO 3-F 4-OSO 2 CF 3 4-SCF 3 HHHHO 3-F 4-OSO 2 CF 3 4-OSO 2 CF 3 HHHHO 3-F 4-OSO 2 CF 3 3,4-Cl 2 HHHHO 3-F 4-Cl 4-Cl HHHHO 3-F 4-Cl 4-Br HHHHO 3-F 4-Cl 4-CF 3 HHHHO 3-F 4-Cl 4-OCHF 2 HHHHO 3-F 4-Cl 4-OCF 2 Br HHHHO 3-F 4-Cl 4-OCF 2 CHF 2 HHHHO 3-F 4-Cl 4-OCF 3 HHHHO 3-F 4-Cl 4-SCF 3 HHHHO 3- F 4-Cl 4-OSO 2 CF 3 ───────────────────────────────────
【００６０】[0060]
【表２６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-Cl 3,4-Cl2 H H H H O 3-F 4-OCF3 4-Cl H H H H O 3-F 4-OCF3 4-Br H H H H O 3-F 4-OCF3 4-CF3 H H H H O 3-F 4-OCF3 4-OCHF2 H H H H O 3-F 4-OCF3 4-OCF2Br H H H H O 3-F 4-OCF3 4-OCF2CHF2 H H H H O 3-F 4-OCF3 4-OCF3 H H H H O 3-F 4-OCF3 4-SCF3 H H H H O 3-F 4-OCF3 4-OSO2CF3 H H H H O 3-F 4-OCF3 3,4-Cl2 H H H H O 3-F 4-OCHF2 4-Cl H H H H O 3-F 4-OCHF2 4-Br H H H H O 3-F 4-OCHF2 4-CF3 H H H H O 3-F 4-OCHF2 4-OCHF2 H H H H O 3-F 4-OCHF2 4-OCF2Br H H H H O 3-F 4-OCHF2 4-OCF2CHF2 H H H H O 3-F 4-OCHF2 4-OCF3 H H H H O 3-F 4-OCHF2 4-SCF3 H H H H O 3-F 4-OCHF2 4-OSO2CF3 H H H H O 3-F 4-OCHF2 3,4-Cl2 H H H H O 3-F 4-Br 4-Cl H H H H O 3-F 4-Br 4-Br ───────────────────────────────────[Table 26] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-Cl 3,4-Cl 2 HHHHO 3-F 4-OCF 3 4-Cl HHHHO 3-F 4-OCF 3 4-Br HHHHO 3-F 4-OCF 3 4-CF 3 HHHHO 3-F 4-OCF 3 4-OCHF 2 HHHHO 3- F 4-OCF 3 4-OCF 2 Br HHHHO 3-F 4-OCF 3 4-OCF 2 CHF 2 HHHHO 3-F 4-OCF 3 4-OCF 3 HHHHO 3-F 4-OCF 3 4-SCF 3 HHHHO 3 -F 4-OCF 3 4-OSO 2 CF 3 HHHHO 3-F 4-OCF 3 3,4-Cl 2 HHHHO 3-F 4-OCHF 2 4-Cl HHHHO 3-F 4-OCHF 2 4-Br HHHHO 3 -F 4-OCHF 2 4-CF 3 HHHHO 3-F 4-OCHF 2 4-OCHF 2 HHHHO 3-F 4-OCHF 2 4-OCF 2 Br HHHHO 3-F 4-OCHF 2 4-OCF 2 CHF 2 HHHHO 3-F 4-OCHF 2 4-OCF 3 HHHHO 3-F 4-OCHF 2 4-SCF 3 HHHHO 3-F 4-OCHF 2 4-OSO 2 CF 3 HHHHO 3-F 4-OCHF 2 3,4-Cl 2 HHHHO 3-F 4-Br 4-Cl HHHHO 3-F 4-Br 4-Br ────────────────────────────── ──────
【００６１】[0061]
【表２７】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 4-Br 4-CF3 H H H H O 3-F 4-Br 4-OCHF2 H H H H O 3-F 4-Br 4-OCF2Br H H H H O 3-F 4-Br 4-OCF2CHF2 H H H H O 3-F 4-Br 4-OCF3 H H H H O 3-F 4-Br 4-SCF3 H H H H O 3-F 4-Br 4-OSO2CF3 H H H H O 3-F 4-Br 3,4-Cl2 H H H H O 3-Br 4-F 4-Cl H H H H O 3-Br 4-F 4-Br H H H H O 3-Br 4-F 4-CF3 H H H H O 3-Br 4-F 4-OCHF2 H H H H O 3-Br 4-F 4-OCF2Br H H H H O 3-Br 4-F 4-OCF2CHF2 H H H H O 3-Br 4-F 4-OCF3 H H H H O 3-Br 4-F 4-SCF3 H H H H O 3-Br 4-F 4-OSO2CF3 H H H H O 3-Br 4-F 3,4-Cl2 H H H H O 3-OCHF2 4-F 4-Cl H H H H O 3-OCHF2 4-F 4-Br H H H H O 3-OCHF2 4-F 4-CF3 H H H H O 3-OCHF2 4-F 4-OCHF2 H H H H O 3-OCHF2 4-F 4-OCF2Br ───────────────────────────────────[Table 27] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 4-Br 4-CF 3 HHHHO 3-F 4-Br 4-OCHF 2 HHHHO 3-F 4-Br 4-OCF 2 Br HHHHO 3-F 4-Br 4-OCF 2 CHF 2 HHHHO 3-F 4-Br 4-OCF 3 HHHHO 3-F 4-Br 4-SCF 3 HHHHO 3-F 4-Br 4-OSO 2 CF 3 HHHHO 3-F 4-Br 3,4-Cl 2 HHHHO 3-Br 4-F 4-Cl HHHHO 3-Br 4-F 4-Br HHHHO 3-Br 4-F 4-CF 3 HHHHO 3-Br 4-F 4-OCHF 2 HHHHO 3-Br 4-F 4-OCF 2 Br HHHHO 3-Br 4-F 4-OCF 2 CHF 2 HHHHO 3-Br 4-F 4-OCF 3 HHHHO 3-Br 4-F 4-SCF 3 HHHHO 3-Br 4-F 4-OSO 2 CF 3 HHHHO 3-Br 4-F 3,4-Cl 2 HHHHO 3 -OCHF 2 4-F 4-Cl HHHHO 3-OCHF 2 4-F 4-Br HHHHO 3-OCHF 2 4-F 4-CF 3 HHHHO 3-OCHF 2 4-F 4-OCHF 2 HHHHO 3-OCHF 2 4 -F 4-OCF 2 Br ────────────────────────────────────
【００６２】[0062]
【表２８】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-OCHF2 4-F 4-OCF2CHF2 H H H H O 3-OCHF2 4-F 4-OCF3 H H H H O 3-OCHF2 4-F 4-SCF3 H H H H O 3-OCHF2 4-F 4-OSO2CF3 H H H H O 3-OCHF2 4-F 3,4-Cl2 H H H H O 3-OCHF2 4-F 4-Cl H H H H O 3-OSO2CF3 4-F 4-Br H H H H O 3-OSO2CF3 4-F 4-CF3 H H H H O 3-OSO2CF3 4-F 4-OCHF2 H H H H O 3-OSO2CF3 4-F 4-OCF2Br H H H H O 3-OSO2CF3 4-F 4-OCF2CHF2 H H H H O 3-OSO2CF3 4-F 4-OCF3 H H H H O 3-OSO2CF3 4-F 4-SCF3 H H H H O 3-OSO2CF3 4-F 4-OSO2CF3 H H H H O 3-OSO2CF3 4-F 3,4-Cl2 H H H H O 3-OCF3 4-F 4-Cl H H H H O 3-OCF3 4-F 4-Br H H H H O 3-OCF3 4-F 4-CF3 H H H H O 3-OCF3 4-F 4-OCHF2 H H H H O 3-OCF3 4-F 4-OCF2Br H H H H O 3-OCF3 4-F 4-OCF2CHF2 H H H H O 3-OCF3 4-F 4-OCF3 H H H H O 3-OCF3 4-F 4-SCF3 ───────────────────────────────────[Table 28] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-OCHF 2 4-F 4-OCF 2 CHF 2 HHHHO 3-OCHF 2 4-F 4-OCF 3 HHHHO 3-OCHF 2 4-F 4-SCF 3 HHHHO 3-OCHF 2 4-F 4-OSO 2 CF 3 HHHHO 3-OCHF 2 4-F 3, 4-Cl 2 HHHHO 3-OCHF 2 4-F 4-Cl HHHHO 3-OSO 2 CF 3 4-F 4-Br HHHHO 3-OSO 2 CF 3 4-F 4-CF 3 HHHHO 3-OSO 2 CF 3 4 -F 4-OCHF 2 HHHHO 3-OSO 2 CF 3 4-F 4-OCF 2 Br HHHHO 3-OSO 2 CF 3 4-F 4-OCF 2 CHF 2 HHHHO 3-OSO 2 CF 3 4-F 4-OCF 3 HHHHO 3-OSO 2 CF 3 4-F 4-SCF 3 HHHHO 3-OSO 2 CF 3 4-F 4-OSO 2 CF 3 HHHHO 3-OSO 2 CF 3 4-F 3,4-Cl 2 HHHHO 3- OCF 3 4-F 4-Cl HHHHO 3-OCF 3 4-F 4-Br HHHHO 3-OCF 3 4-F 4-CF 3 HHHHO 3-OCF 3 4-F 4-OCHF 2 HHHHO 3-OCF 3 4- F 4-OCF 2 Br HHHHO 3-OCF 3 4-F 4-OCF 2 CHF 2 HHHHO 3-OCF 3 4-F 4-OCF 3 HHHHO 3-OCF 3 4-F 4-SCF 3 ────── ───────────────── ───────────
【００６３】[0063]
【表２９】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-OCF3 4-F 4-OSO2CF3 H H H H O 3-OCF3 4-F 3,4-Cl2 H H H H O 3-Cl 4-CN 4-Cl H H H H O 3-Cl 4-CN 4-Br H H H H O 3-Cl 4-CN 4-CF3 H H H H O 3-Cl 4-CN 4-OCHF2 H H H H O 3-Cl 4-CN 4-OCF2Br H H H H O 3-Cl 4-CN 4-OCF2CHF2 H H H H O 3-Cl 4-CN 4-OCF3 H H H H O 3-Cl 4-CN 4-SCF3 H H H H O 3-Cl 4-CN 4-OSO2CF3 H H H H O 3-Cl 4-CN 3,4-Cl2 H H H H O 3-CF3 4-CN 4-Cl H H H H O 3-CF3 4-CN 4-Br H H H H O 3-CF3 4-CN 4-CF3 H H H H O 3-CF3 4-CN 4-OCHF2 H H H H O 3-CF3 4-CN 4-OCF2Br H H H H O 3-CF3 4-CN 4-OCF2CHF2 H H H H O 3-CF3 4-CN 4-OCF3 H H H H O 3-CF3 4-CN 4-SCF3 H H H H O 3-CF3 4-CN 4-OSO2CF3 H H H H O 3-CF3 4-CN 3,4-Cl2 H H H H O 3-OCF2CHF2 4-F 4-Cl ───────────────────────────────────[Table 29] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-OCF 3 4-F 4-OSO 2 CF 3 HHHHO 3-OCF 3 4-F 3,4-Cl 2 HHHHO 3-Cl 4-CN 4-Cl HHHHO 3-Cl 4-CN 4-Br HHHHO 3-Cl 4-CN 4-CF 3 HHHHO 3- Cl 4-CN 4-OCHF 2 HHHHO 3-Cl 4-CN 4-OCF 2 Br HHHHO 3-Cl 4-CN 4-OCF 2 CHF 2 HHHHO 3-Cl 4-CN 4-OCF 3 HHHHO 3-Cl 4- CN 4-SCF 3 HHHHO 3-Cl 4-CN 4-OSO 2 CF 3 HHHHO 3-Cl 4-CN 3,4-Cl 2 HHHHO 3-CF 3 4-CN 4-Cl HHHHO 3-CF 3 4-CN 4-Br HHHHO 3-CF 3 4-CN 4-CF 3 HHHHO 3-CF 3 4-CN 4-OCHF 2 HHHHO 3-CF 3 4-CN 4-OCF 2 Br HHHHO 3-CF 3 4-CN 4- OCF 2 CHF 2 HHHHO 3-CF 3 4-CN 4-OCF 3 HHHHO 3-CF 3 4-CN 4-SCF 3 HHHHO 3-CF 3 4-CN 4-OSO 2 CF 3 HHHHO 3-CF 3 4-CN 3,4-Cl 2 HHHHO 3-OCF 2 CHF 2 4-F 4-Cl ──────────────────────────────── ────
【００６４】[0064]
【表３０】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-OCF2CHF2 4-F 4-Br H H H H O 3-OCF2CHF2 4-F 4-CF3 H H H H O 3-OCF2CHF2 4-F 4-OCHF2 H H H H O 3-OCF2CHF2 4-F 4-OCF2Br H H H H O 3-OCF2CHF2 4-F 4-OCF2CHF2 H H H H O 3-OCF2CHF2 4-F 4-OCF3 H H H H O 3-OCF2CHF2 4-F 4-SCF3 H H H H O 3-OCF2CHF2 4-F 4-OSO2CF3 H H H H O 3-OCF2CHF2 4-F 3,4-Cl2 H H H H O 4-F 4-F 4-Cl H H H H O 4-F 4-F 4-Br H H H H O 4-F 4-F 4-CF3 H H H H O 4-F 4-F 4-OCHF2 H H H H O 4-F 4-F 4-OCF2Br H H H H O 4-F 4-F 4-OCF2CHF2 H H H H O 4-F 4-F 4-OCF3 H H H H O 4-F 4-F 4-SCF3 H H H H O 4-F 4-F 4-OSO2CF3 H H H H O 4-F 4-F 3,4-Cl2 H H H H O 3-CN 4-F 4-Cl H H H H O 3-CN 4-F 4-Br H H H H O 3-CN 4-F 4-CF3 H H H H O 3-CN 4-F 4-OCHF2 ───────────────────────────────────[Table 30] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-OCF 2 CHF 2 4-F 4- Br HHHHO 3-OCF 2 CHF 2 4-F 4-CF 3 HHHHO 3-OCF 2 CHF 2 4-F 4-OCHF 2 HHHHO 3-OCF 2 CHF 2 4-F 4-OCF 2 Br HHHHO 3-OCF 2 CHF 2 4-F 4-OCF 2 CHF 2 HHHHO 3-OCF 2 CHF 2 4-F 4-OCF 3 HHHHO 3-OCF 2 CHF 2 4-F 4-SCF 3 HHHHO 3-OCF 2 CHF 2 4-F 4- OSO 2 CF 3 HHHHO 3-OCF 2 CHF 2 4-F 3,4-Cl 2 HHHHO 4-F 4-F 4-Cl HHHHO 4-F 4-F 4-Br HHHHO 4-F 4-F 4-CF 3 HHHHO 4-F 4-F 4-OCHF 2 HHHHO 4-F 4-F 4-OCF 2 Br HHHHO 4-F 4-F 4-OCF 2 CHF 2 HHHHO 4-F 4-F 4-OCF 3 HHHHO 4 -F 4-F 4-SCF 3 HHHHO 4-F 4-F 4-OSO 2 CF 3 HHHHO 4-F 4-F 3,4-Cl 2 HHHHO 3-CN 4-F 4-Cl HHHHO 3-CN 4 -F 4-Br HHHHO 3-CN 4-F 4-CF 3 HHHHO 3-CN 4-F 4-OCHF 2 ──────────────────────── ─────────────
【００６５】[0065]
【表３１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CN 4-F 4-OCF2Br H H H H O 3-CN 4-F 4-OCF2CHF2 H H H H O 3-CN 4-F 4-OCF3 H H H H O 3-CN 4-F 4-SCF3 H H H H O 3-CN 4-F 4-OSO2CF3 H H H H O 3-CN 4-F 3,4-Cl2 H H H H O 4-OCHF2 4-F 4-Cl H H H H O 4-OCHF2 4-F 4-Br H H H H O 4-OCHF2 4-F 4-CF3 H H H H O 4-OCHF2 4-F 4-OCHF2 H H H H O 4-OCHF2 4-F 4-OCF2Br H H H H O 4-OCHF2 4-F 4-OCF2CHF2 H H H H O 4-OCHF2 4-F 4-OCF3 H H H H O 4-OCHF2 4-F 4-SCF3 H H H H O 4-OCHF2 4-F 4-OSO2CF3 H H H H O 4-OCHF2 4-F 3,4-Cl2 H H H H O 4-OCHF2 4-F 4-Cl H H H H O 3-F 2,4-F2 4-Br H H H H O 3-F 2,4-F2 4-CF3 H H H H O 3-F 2,4-F2 4-OCHF2 H H H H O 3-F 2,4-F2 4-OCF2Br H H H H O 3-F 2,4-F2 4-OCF2CHF2 H H H H O 3-F 2,4-F2 4-OCF3 ───────────────────────────────────[Table 31] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CN 4-F 4-OCF 2 Br HHHHO 3-CN 4-F 4-OCF 2 CHF 2 HHHHO 3-CN 4-F 4-OCF 3 HHHHO 3-CN 4-F 4-SCF 3 HHHHO 3-CN 4-F 4-OSO 2 CF 3 HHHHO 3 -CN 4-F 3,4-Cl 2 HHHHO 4-OCHF 2 4-F 4-Cl HHHHO 4-OCHF 2 4-F 4-Br HHHHO 4-OCHF 2 4-F 4-CF 3 HHHHO 4-OCHF 2 4-F 4-OCHF 2 HHHHO 4-OCHF 2 4-F 4-OCF 2 Br HHHHO 4-OCHF 2 4-F 4-OCF 2 CHF 2 HHHHO 4-OCHF 2 4-F 4-OCF 3 HHHHO 4-OCHF 2 4-F 4-SCF 3 HHHHO 4-OCHF 2 4-F 4-OSO 2 CF 3 HHHHO 4-OCHF 2 4-F 3,4-Cl 2 HHHHO 4-OCHF 2 4-F 4-Cl HHHHO 3- F 2,4-F 2 4-Br HHHHO 3-F 2,4-F 2 4-CF 3 HHHHO 3-F 2,4-F 2 4-OCHF 2 HHHHO 3-F 2,4-F 2 4- OCF 2 Br HHHHO 3-F 2,4-F 2 4-OCF 2 CHF 2 HHHHO 3-F 2,4-F 2 4-OCF 3 ────────────────── ──────────────────
【００６６】[0066]
【表３２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 2,4-F2 4-SCF3 H H H H O 3-F 2,4-F2 4-OSO2CF3 H H H H O 3-F 2,4-F2 3,4-Cl2 H H H H O 3-F 3,4-F2 4-Cl H H H H O 3-F 3,4-F2 4-Br H H H H O 3-F 3,4-F2 4-CF3 H H H H O 3-F 3,4-F2 4-OCHF2 H H H H O 3-F 3,4-F2 4-OCF2Br H H H H O 3-F 3,4-F2 4-OCF2CHF2 H H H H O 3-F 3,4-F2 4-OCF3 H H H H O 3-F 3,4-F2 4-SCF3 H H H H O 3-F 3,4-F2 4-OSO2CF3 H H H H O 3-F 3,4-F2 3,4-Cl2 H H H H O 3,4-F2 4-F 4-Cl H H H H O 3,4-F2 4-F 4-Br H H H H O 3,4-F2 4-F 4-CF3 H H H H O 3,4-F2 4-F 4-OCHF2 H H H H O 3,4-F2 4-F 4-OCF2Br H H H H O 3,4-F2 4-F 4-OCF2CHF2 H H H H O 3,4-F2 4-F 4-OCF3 H H H H O 3,4-F2 4-F 4-SCF3 H H H H O 3,4-F2 4-F 4-OSO2CF3 H H H H O 3,4-F2 4-F 3,4-Cl2 ───────────────────────────────────[Table 32] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 2,4-F 2 4- SCF 3 HHHHO 3-F 2,4-F 2 4-OSO 2 CF 3 HHHHO 3-F 2,4-F 2 3,4-Cl 2 HHHHO 3-F 3,4-F 2 4-Cl HHHHO 3- F 3,4-F 2 4-Br HHHHO 3-F 3,4-F 2 4-CF 3 HHHHO 3-F 3,4-F 2 4-OCHF 2 HHHHO 3-F 3,4-F 2 4- OCF 2 Br HHHHO 3-F 3,4-F 2 4-OCF 2 CHF 2 HHHHO 3-F 3,4-F 2 4-OCF 3 HHHHO 3-F 3,4-F 2 4-SCF 3 HHHHO 3- F 3,4-F 2 4-OSO 2 CF 3 HHHHO 3-F 3,4-F 2 3,4-Cl 2 HHHHO 3,4-F 2 4-F 4-Cl HHHHO 3,4-F 2 4 -F 4-Br HHHHO 3,4-F 2 4-F 4-CF 3 HHHHO 3,4-F 2 4-F 4-OCHF 2 HHHHO 3,4-F 2 4-F 4-OCF 2 Br HHHHO 3 , 4-F 2 4-F 4-OCF 2 CHF 2 HHHHO 3,4-F 2 4-F 4-OCF 3 HHHHO 3,4-F 2 4-F 4-SCF 3 HHHHO 3,4-F 2 4 -F 4-OSO 2 CF 3 HHHHO 3,4-F 2 4-F 3,4-Cl 2 ─────────────────────────── ─────────
【００６７】[0067]
【表３３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 H 4-Cl H H H H O 3-CF3 2-F 4-CF3 H H H H O 3-CF3 3-F 4-OCF3 H H H H O 3-CF3 2-Cl 4-Cl H H H H O 3-CF3 3-Cl 4-CF3 H H H H O 3-CF3 4-Cl 4-OCF3 H H H H O 3-CF3 3-Br 4-Cl H H H H O 3-CF3 4-Br 4-CF3 H H H H O 3-CF3 3-I 4-OCF3 H H H H O 3-CF3 4-I 4-Cl H H H H O 3-CF3 4-CH3 4-CF3 H H H H O 3-CF3 4-CH2CH3 4-OCF3 H H H H O 3-CF3 4-CH(CH3)2 4-Cl H H H H O 3-CF3 4-CH2CH2CH2CH3 4-CF3 H H H H O 3-CF3 4-C(CH3)3 4-OCF3 H H H H O 3-CF3 4-CH2CH=CH2 4-Cl H H H H O 3-CF3 4-Q1 4-CF3 H H H H O 3-CF3 4-Q2 4-OCF3 H H H H O 3-CF3 4-Q3 4-Cl H H H H O 3-CF3 4-Q4 4-CF3 H H H H O 3-CF3 4-CHF2 4-OCF3 H H H H O 3-CF3 4-CH2Br 4-Cl H H H H O 3-CF3 4-CH2Cl 4-CF3 ───────────────────────────────────[Table 33] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 H 4-Cl HHHHO 3- CF 3 2-F 4-CF 3 HHHHO 3-CF 3 3-F 4-OCF 3 HHHHO 3-CF 3 2-Cl 4-Cl HHHHO 3-CF 3 3-Cl 4-CF 3 HHHHO 3-CF 3 4 -Cl 4-OCF 3 HHHHO 3-CF 3 3-Br 4-Cl HHHHO 3-CF 3 4-Br 4-CF 3 HHHHO 3-CF 3 3-I 4-OCF 3 HHHHO 3-CF 3 4-I 4 -Cl HHHHO 3-CF 3 4-CH 3 4-CF 3 HHHHO 3-CF 3 4-CH 2 CH 3 4-OCF 3 HHHHO 3-CF 3 4-CH (CH 3 ) 2 4-Cl HHHHO 3-CF 3 4-CH 2 CH 2 CH 2 CH 3 4-CF 3 HHHHO 3-CF 3 4-C (CH 3 ) 3 4-OCF 3 HHHHO 3-CF 3 4-CH 2 CH = CH 2 4-Cl HHHHO 3 -CF 3 4-Q1 4-CF 3 HHHHO 3-CF 3 4-Q2 4-OCF 3 HHHHO 3-CF 3 4-Q3 4-Cl HHHHO 3-CF 3 4-Q4 4-CF 3 HHHHO 3-CF 3 4-CHF 2 4-OCF 3 HHHHO 3-CF 3 4-CH 2 Br 4-Cl HHHHO 3-CF 3 4-CH 2 Cl 4-CF 3 ──────────────── ────────────────────
【００６８】[0068]
【表３４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 2-CF3 4-Cl H H H H O 3-CF3 3-CF3 4-CF3 H H H H O 3-CF3 4-CF3 4-OCF3 H H H H O 3-CF3 4-CH=C(Cl)CF3 4-Cl H H H H O 3-CF3 4-(Q4-1-Cl) 4-CF3 H H H H O 3-CF3 4-CH2CN 4-OCF3 H H H H O 3-CF3 4-CH2OH 4-Cl H H H H O 3-CF3 4-CH2CO2H 4-CF3 H H H H O 3-CF3 4-OCH3 4-OCF3 H H H H O 3-CF3 4-OCH2CH3 4-Cl H H H H O 3-CF3 4-OCH(CH3)2 4-CF3 H H H H O 3-CF3 4-OCH2CH2CH2CH3 4-OCF3 H H H H O 3-CF3 4-OC(CH3)3 4-Cl H H H H O 3-CF3 4-O(Q4) 4-CF3 H H H H O 3-CF3 4-OCHF2 4-OCF3 H H H H O 3-CF3 4-OCF2Br 4-Cl H H H H O 3-CF3 2-OCF3 4-CF3 H H H H O 3-CF3 3-OCF3 4-OCF3 H H H H O 3-CF3 4-OCF3 4-Cl H H H H O 3-CF3 4-OCH2CF3 4-CF3 H H H H O 3-CF3 4-OCF2CF3 4-OCF3 H H H H O 3-CF3 4-OCF2CHF2 4-Cl H H H H O 3-CF3 4-OCF2CHFCl 4-CF3 ───────────────────────────────────[Table 34] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 2-CF 3 4-Cl HHHHO 3-CF 3 3-CF 3 4-CF 3 HHHHO 3-CF 3 4-CF 3 4-OCF 3 HHHHO 3-CF 3 4-CH = C (Cl) CF 3 4-Cl HHHHO 3-CF 3 4 -(Q4-1-Cl) 4-CF 3 HHHHO 3-CF 3 4-CH 2 CN 4-OCF 3 HHHHO 3-CF 3 4-CH 2 OH 4-Cl HHHHO 3-CF 3 4-CH 2 CO 2 H 4-CF 3 HHHHO 3-CF 3 4-OCH 3 4-OCF 3 HHHHO 3-CF 3 4-OCH 2 CH 3 4-Cl HHHHO 3-CF 3 4-OCH (CH 3 ) 2 4-CF 3 HHHHO 3-CF 3 4-OCH 2 CH 2 CH 2 CH 3 4-OCF 3 HHHHO 3-CF 3 4-OC (CH 3 ) 3 4-Cl HHHHO 3-CF 3 4-O (Q4) 4-CF 3 HHHHO 3-CF 3 4-OCHF 2 4-OCF 3 HHHHO 3-CF 3 4-OCF 2 Br 4-Cl HHHHO 3-CF 3 2-OCF 3 4-CF 3 HHHHO 3-CF 3 3-OCF 3 4-OCF 3 HHHHO 3-CF 3 4-OCF 3 4-Cl HHHHO 3-CF 3 4-OCH 2 CF 3 4-CF 3 HHHHO 3-CF 3 4-OCF 2 CF 3 4-OCF 3 HHHHO 3-CF 3 4- OCF 2 CHF 2 4-Cl HHHHO 3-CF 3 4-OCF 2 CHFCl 4-CF 3 ────────── ────────────────────────
【００６９】[0069]
【表３５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 4-OCF2CHFBr 4-Cl H H H H O 3-CF3 4-OCF2CF2CF3 4-CF3 H H H H O 3-CF3 4-OCH2CH=CHCl 4-OCF3 H H H H O 3-CF3 4-O(Q4-2,2-Cl2) 4-Cl H H H H O 3-CF3 4-SCH3 4-CF3 H H H H O 3-CF3 4-SCHF2 4-OCF3 H H H H O 3-CF3 4-SCF2Br 4-Cl H H H H O 3-CF3 4-SCF3 4-CF3 H H H H O 3-CF3 4-SCF2CHF2 4-OCF3 H H H H O 3-CF3 4-SOCH3 4-Cl H H H H O 3-CF3 4-SOCF3 4-CF3 H H H H O 3-CF3 4-SOCF2CHF2 4-OCF3 H H H H O 3-CF3 4-SO2CH3 4-Cl H H H H O 3-CF3 4-SO2CF3 4-CF3 H H H H O 3-CF3 4-SO2CHF2 4-OCF3 H H H H O 3-CF3 4-SO2CF2Br 4-Cl H H H H O 3-CF3 4-CH2OCH3 4-CF3 H H H H O 3-CF3 4-OCF2CHFOCF3 4-OCF3 H H H H O 3-CF3 4-CH2SCH3 4-Cl H H H H O 3-CF3 4-CH2COCH3 4-CF3 H H H H O 3-CF3 4-CH2CO2CH3 4-OCF3 H H H H O 3-CF3 4-OCO2CH3 4-Cl H H H H O 3-CF3 4-OCOCH3 4-CF3 ───────────────────────────────────[Table 35] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 4-OCF 2 CHFBr 4- Cl HHHHO 3-CF 3 4-OCF 2 CF 2 CF 3 4-CF 3 HHHHO 3-CF 3 4-OCH 2 CH = CHCl 4-OCF 3 HHHHO 3-CF 3 4-O (Q4-2,2-Cl 2 ) 4-Cl HHHHO 3-CF 3 4-SCH 3 4-CF 3 HHHHO 3-CF 3 4-SCHF 2 4-OCF 3 HHHHO 3-CF 3 4-SCF 2 Br 4-Cl HHHHO 3-CF 3 4 -SCF 3 4-CF 3 HHHHO 3-CF 3 4-SCF 2 CHF 2 4-OCF 3 HHHHO 3-CF 3 4-SOCH 3 4-Cl HHHHO 3-CF 3 4-SOCF 3 4-CF 3 HHHHO 3- CF 3 4-SOCF 2 CHF 2 4-OCF 3 HHHHO 3-CF 3 4-SO 2 CH 3 4-Cl HHHHO 3-CF 3 4-SO 2 CF 3 4-CF 3 HHHHO 3-CF 3 4-SO 2 CHF 2 4-OCF 3 HHHHO 3-CF 3 4-SO 2 CF 2 Br 4-Cl HHHHO 3-CF 3 4-CH 2 OCH 3 4-CF 3 HHHHO 3-CF 3 4-OCF 2 CHFOCF 3 4-OCF 3 HHHHO 3-CF 3 4-CH 2 SCH 3 4-Cl HHHHO 3-CF 3 4-CH 2 COCH 3 4-CF 3 HHHHO 3-CF 3 4-CH 2 CO 2 CH 3 4-OCF 3 HHHHO 3- CF 3 4-OCO 2 CH 3 4-Cl HHHHO 3-CF 3 4-OCOCH 3 4 -CF 3 ───────────────────────────────────
【００７０】[0070]
【表３６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 4-COCH3 4-Cl H H H H O 3-CF3 4-COCF3 4-CF3 H H H H O 3-CF3 4-CO2CH2CH3 4-OCF3 H H H H O 3-CF3 4-CO2C(CH3)3 4-Cl H H H H O 3-CF3 4-CO2CH2CF3 4-CF3 H H H H O 3-CF3 4-OCH2CO2CH3 4-OCF3 H H H H O 3-CF3 4-NO2 4-Cl H H H H O 3-CF3 4-OH 4-CF3 H H H H O 3-CF3 4-CO2H 4-OCF3 H H H H O 3-CF3 4-SCN 4-Cl H H H H O 3-CF3 4-OSO2CH3 4-CF3 H H H H O 3-CF3 4-OSO2CF3 4-OCF3 H H H H O 3-CF3 4-CSCH3 4-Cl H H H H O 3-CF3 4-NH2 4-CF3 H H H H O 3-CF3 4-N(CH3)2 4-OCF3 H H H H O 3-CF3 4-N(CH3)CH2CH=CH2 4-Cl H H H H O 3-CF3 4-CON(CH3)2 4-CF3 H H H H O 3-CF3 4-OCON(CH3)2 4-OCF3 H H H H O 3-CF3 4-NHCOCH3 4-Cl H H H H O 3-CF3 4-SO2N(CH3)2 4-CF3 H H H H O 3-CF3 4-Si(CH3)3 4-OCF3 H H H H O 3-CF3 4-C6H5 4-Cl H H H H O 3-CF3 4-(C6H4-4-Cl) 4-CF3 ───────────────────────────────────[Table 36] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 4-COCH 3 4-Cl HHHHO 3-CF 3 4-COCF 3 4-CF 3 HHHHO 3-CF 3 4-CO 2 CH 2 CH 3 4-OCF 3 HHHHO 3-CF 3 4-CO 2 C (CH 3 ) 3 4-Cl HHHHO 3 -CF 3 4-CO 2 CH 2 CF 3 4-CF 3 HHHHO 3-CF 3 4-OCH 2 CO 2 CH 3 4-OCF 3 HHHHO 3-CF 3 4-NO 2 4-Cl HHHHO 3-CF 3 4 -OH 4-CF 3 HHHHO 3-CF 3 4-CO 2 H 4-OCF 3 HHHHO 3-CF 3 4-SCN 4-Cl HHHHO 3-CF 3 4-OSO 2 CH 3 4-CF 3 HHHHO 3-CF 3 4-OSO 2 CF 3 4-OCF 3 HHHHO 3-CF 3 4-CSCH 3 4-Cl HHHHO 3-CF 3 4-NH 2 4-CF 3 HHHHO 3-CF 3 4-N (CH 3 ) 2 4 -OCF 3 HHHHO 3-CF 3 4-N (CH 3 ) CH 2 CH = CH 2 4-Cl HHHHO 3-CF 3 4-CON (CH 3 ) 2 4-CF 3 HHHHO 3-CF 3 4-OCON ( CH 3 ) 2 4-OCF 3 HHHHO 3-CF 3 4-NHCOCH 3 4-Cl HHHHO 3-CF 3 4-SO 2 N (CH 3 ) 2 4-CF 3 HHHHO 3-CF 3 4-Si (CH 3 ) 3 4-OCF 3 HHHHO 3-CF 3 4-C 6 H 5 4-Cl HHHHO 3-CF 3 4- (C 6 H 4 -4-Cl) 4-CF 3 ───────────────────────────────────
【００７１】[0071]
【表３７】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 4-OC6H5 4-Cl H H H H O 3-CF3 4-O(C6H4-4-CF3) 4-CF3 H H H H O 3-CF3 3-O(C6H4-4-CF3) 4-OCF3 H H H H O 3-CF3 4-S(C6H4-4-CF3) 4-Cl H H H H O 3-CF3 4-SO2C6H5 4-CF3 H H H H O 3-CF3 4-NH(C6H4-4-Cl) 4-OCF3 H H H H O 3-CF3 4-CH2C6H5 4-Cl H H H H O 3-CF3 4-COC6H5 4-CF3 H H H H O 3-CF3 4-OCH2(C6H4-4-CF3) 4-OCF3 H H H H O 3-CF3 4-CH2OC6H5 4-Cl H H H H O 3-CF3 4-NHCH2C6H5 4-CF3 H H H H O 3-CF3 4-CH2CH2C6H5 4-OCF3 H H H H O 3-CF3 4-N=NC6H5 4-Cl H H H H O 3-CF3 4-CH=CHC6H5 4-CF3 H H H H O 3-CF3 2-CH=CH-CH=CH-3 4-OCF3 H H H H O 3-CF3 3-CH=CH-CH=CH-4 4-Cl H H H H O 3-CF3 3-OCH2O-4 4-CF3 H H H H O 3-CF3 3-OCF2O-4 4-OCF3 H H H H O 3-CF3 3-OCH2CH2O-4 4-Cl H H H H O 3-CF3 3-OCF2CF2O-4 4-CF3 H H H H O 3-CF3 3-OCF2CF2-4 4-OCF3 H H H H O 3-CF3 3-CF2CF2O-4 4-Cl H H H H O 3-CF3 4-NHSO2CH3 4-CF3 ───────────────────────────────────[Table 37] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 4-OC 6 H 5 4 -Cl HHHHO 3-CF 3 4-O (C 6 H 4 -4-CF 3 ) 4-CF 3 HHHHO 3-CF 3 3-O (C 6 H 4 -4-CF 3 ) 4-OCF 3 HHHHO 3 -CF 3 4-S (C 6 H 4 -4-CF 3 ) 4-Cl HHHHO 3-CF 3 4-SO 2 C 6 H 5 4-CF 3 HHHHO 3-CF 3 4-NH (C 6 H 4 -4-Cl) 4-OCF 3 HHHHO 3-CF 3 4-CH 2 C 6 H 5 4-Cl HHHHO 3-CF 3 4-COC 6 H 5 4-CF 3 HHHHO 3-CF 3 4-OCH 2 ( C 6 H 4 -4-CF 3 ) 4-OCF 3 HHHHO 3-CF 3 4-CH 2 OC 6 H 5 4-Cl HHHHO 3-CF 3 4-NHCH 2 C 6 H 5 4-CF 3 HHHHO 3- CF 3 4-CH 2 CH 2 C 6 H 5 4-OCF 3 HHHHO 3-CF 3 4-N = NC 6 H 5 4-Cl HHHHO 3-CF 3 4-CH = CHC 6 H 5 4-CF 3 HHHHO 3-CF 3 2-CH = CH-CH = CH-3 4-OCF 3 HHHHO 3-CF 3 3-CH = CH-CH = CH-4 4-Cl HHHHO 3-CF 3 3-OCH 2 O-4 4-CF 3 HHHHO 3-CF 3 3-OCF 2 O-4 4-OCF 3 HHHHO 3-CF 3 3-OCH 2 CH 2 O-4 4-Cl HHHHO 3-CF 3 3-OCF 2 CF 2 O- 4 4-CF 3 HHHHO 3-CF 3 3 -OCF 2 CF 2 -4 4-OCF 3 HHHHO 3-CF 3 3-CF 2 CF 2 O-4 4-Cl HHHHO 3-CF 3 4-NHSO 2 CH 3 4-CF 3 ──────── ────────────────────────────
【００７２】[0072]
【表３８】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 2,3-F2 4-Cl H H H H O 3-CF3 2,4-F2 4-CF3 H H H H O 3-CF3 2,5-F2 4-OCF3 H H H H O 3-CF3 2,6-F2 4-Cl H H H H O 3-CF3 3,4-F2 4-CF3 H H H H O 3-CF3 3,5-F2 4-OCF3 H H H H O 3-CF3 2,4-Cl2 4-Cl H H H H O 3-CF3 3,4-Cl2 4-CF3 H H H H O 3-CF3 3,4-Br2 4-OCF3 H H H H O 3-CF3 2,4-I2 4-Cl H H H H O 3-CF3 2,4-(CH3)2 4-CF3 H H H H O 3-CF3 3,4-(OCH3)2 4-OCF3 H H H H O 3-CF3 2-F-4-Cl 4-Cl H H H H O 3-CF3 2-F-4-Br 4-CF3 H H H H O 3-CF3 2-F-4-CF3 4-OCF3 H H H H O 3-CF3 2-F-4-OCHF2 4-Cl H H H H O 3-CF3 2-F-4-OSO2CF3 4-CF3 H H H H O 3-CF3 2-F-4-O(C6H4-4-Cl) 4-OCF3 H H H H O 3-CF3 2-F-4-O(Q5-5-CF3) 4-Cl H H H H O 3-CF3 3-Cl-4-CF3 4-CF3 H H H H O 3-CF3 3-F-4-OCF3 4-OCF3 H H H H O 3-CF3 3,4-(CF3)2 4-Cl H H H H O 3-CF3 3,4-(OCF3)2 4-CF3 ───────────────────────────────────[Table 38] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 2,3-F 2 4 -Cl HHHHO 3-CF 3 2,4-F 2 4-CF 3 HHHHO 3-CF 3 2,5-F 2 4-OCF 3 HHHHO 3-CF 3 2,6-F 2 4-Cl HHHHO 3-CF 3 3,4-F 2 4-CF 3 HHHHO 3-CF 3 3,5-F 2 4-OCF 3 HHHHO 3-CF 3 2,4-Cl 2 4-Cl HHHHO 3-CF 3 3,4-Cl 2 4-CF 3 HHHHO 3-CF 3 3,4-Br 2 4-OCF 3 HHHHO 3-CF 3 2,4-I 2 4-Cl HHHHO 3-CF 3 2,4- (CH 3 ) 2 4- CF 3 HHHHO 3-CF 3 3,4- (OCH 3 ) 2 4-OCF 3 HHHHO 3-CF 3 2-F-4-Cl 4-Cl HHHHO 3-CF 3 2-F-4-Br 4-CF 3 HHHHO 3-CF 3 2-F-4-CF 3 4-OCF 3 HHHHO 3-CF 3 2-F-4-OCHF 2 4-Cl HHHHO 3-CF 3 2-F-4-OSO 2 CF 3 4 -CF 3 HHHHO 3-CF 3 2-F-4-O (C 6 H 4 -4-Cl) 4-OCF 3 HHHHO 3-CF 3 2-F-4-O (Q5-5-CF 3 ) 4 -Cl HHHHO 3-CF 3 3-Cl-4-CF 3 4-CF 3 HHHHO 3-CF 3 3-F-4-OCF 3 4-OCF 3 HHHHO 3-CF 3 3,4- (CF 3 ) 2 4-Cl HHHHO 3-CF 3 3,4- (OCF 3) 2 4-CF 3 ──────── ──────────────────────────
【００７３】[0073]
【表３９】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-CF3 3-CN 4-Cl H H H H O 3-CF3 2-Cl-4-CN 4-CF3 H H H H O 3-CF3 3-Cl-4-CN 4-OCF3 H H H H O 3-CF3 2-CH3-4-CN 4-Cl H H H H O 3-CF3 3-CH3-4-CN 4-CF3 H H H H O 3-CF3 3,4-(CN)2 4-OCF3 H H H H O 3-CF3 2,5-F2-4-Cl 4-Cl H H H H O 3-CF3 3,5-F2-4-CF3 4-CF3 H H H H O 3-CF3 2,3,4-F3 4-OCF3 H H H H O 3-CF3 2,4,5-F3 4-Cl H H H H O 3-CF3 3,4,5-F3 4-CF3 H H H H O 3-CF3 2,3,4-Cl3 4-OCF3 H H H H O 3-CF3 2,4,5-Cl3 4-Cl H H H H O 3-CF3 2,4,6-Cl3 4-CF3 H H H H O 3-CF3 2-F-4,5-Cl2 4-OCF3 H H H H O 3-CF3 3-Cl-4-F 4-Cl H H H H O 3-CF3 2-F-4-OCHF2-5-Cl 4-CF3 H H H H O 3-CF3 2,3,4,5-F4 4-OCF3 H H H H O 3-CF3 2,3,5,6-F4 4-Cl H H H H O 3-CF3 2,4-F2-3,5-Cl2 4-CF3 H H H H O 3-CF3 2,3,4,5,6-F5 4-OCF3 H H H H O 3-CF3 2,3,5,6-F4-4-CN 4-Cl H H H H O 3-CF3 4-NHCONHCH3 4-CF3 ───────────────────────────────────[Table 39] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-CF 3 3-CN 4-Cl HHHHO 3-CF 3 2-Cl-4-CN 4-CF 3 HHHHO 3-CF 3 3-Cl-4-CN 4-OCF 3 HHHHO 3-CF 3 2-CH 3 -4-CN 4-Cl HHHHO 3- CF 3 3-CH 3 -4-CN 4-CF 3 HHHHO 3-CF 3 3,4- (CN) 2 4-OCF 3 HHHHO 3-CF 3 2,5-F 2 -4-Cl 4-Cl HHHHO 3-CF 3 3,5-F 2 -4-CF 3 4-CF 3 HHHHO 3-CF 3 2,3,4-F 3 4-OCF 3 HHHHO 3-CF 3 2,4,5-F 3 4 -Cl HHHHO 3-CF 3 3,4,5-F 3 4-CF 3 HHHHO 3-CF 3 2,3,4-Cl 3 4-OCF 3 HHHHO 3-CF 3 2,4,5-Cl 3 4 -Cl HHHHO 3-CF 3 2,4,6-Cl 3 4-CF 3 HHHHO 3-CF 3 2-F-4,5-Cl 2 4-OCF 3 HHHHO 3-CF 3 3-Cl-4-F 4-Cl HHHHO 3-CF 3 2-F-4-OCHF 2 -5-Cl 4-CF 3 HHHHO 3-CF 3 2,3,4,5-F 4 4-OCF 3 HHHHO 3-CF 3 2, 3,5,6-F 4 4-Cl HHHHO 3-CF 3 2,4-F 2 -3,5-Cl 2 4-CF 3 HHHHO 3-CF 3 2,3,4,5,6-F 5 4-OCF 3 HHHHO 3-CF 3 2,3,5,6-F 4 -4-CN 4-Cl HHHHO 3-CF 3 4-NHCONHCH 3 4-CF 3 ─── ────────────────────────────────
【００７４】[0074]
【表４０】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-F 3-F 4-Cl H H H H O 3-F 3-Cl 4-CF3 H H H H O 3-F 3-Br 4-OCF3 H H H H O 3-F 4-CN 4-Cl H H H H O 3-F 4-NO2 4-CF3 H H H H O 3-F 4-CH3 4-OCF3 H H H H O 3-F 4-CF3 4-Cl H H H H O 3-F 4-OCH2CH3 4-CF3 H H H H O 3-F 4-OCHF2 4-OCF3 H H H H O 3-F 4-OCH2CF3 4-Cl H H H H O 3-F 4-OCF2Br 4-CF3 H H H H O 3-F 4-OCF2CHF2 4-OCF3 H H H H O 3-F 4-OSO2CF3 4-Cl H H H H O 3-F 4-SCHF2 4-CF3 H H H H O 3-F 4-SCF3 4-OCF3 H H H H O 3-F 4-SCH3 4-Cl H H H H O 3-F 4-SOCH3 4-CF3 H H H H O 3-F 4-SO2CH3 4-OCF3 H H H H O 3-F 4-OSO2CH3 4-Cl H H H H O 3-F 4-NHCOCH3 4-CF3 H H H H O 3-F 4-NHSO2CH3 4-OCF3 H H H H O 3-F 2,4-Cl2 4-Cl H H H H O 3-F 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 40] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-F 3-F 4-Cl HHHHO 3 -F 3-Cl 4-CF 3 HHHHO 3-F 3-Br 4-OCF 3 HHHHO 3-F 4-CN 4-Cl HHHHO 3-F 4-NO 2 4-CF 3 HHHHO 3-F 4-CH 3 4-OCF 3 HHHHO 3-F 4-CF 3 4-Cl HHHHO 3-F 4-OCH 2 CH 3 4-CF 3 HHHHO 3-F 4-OCHF 2 4-OCF 3 HHHHO 3-F 4-OCH 2 CF 3 4-Cl HHHHO 3-F 4-OCF 2 Br 4-CF 3 HHHHO 3-F 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-F 4-OSO 2 CF 3 4-Cl HHHHO 3-F 4- SCHF 2 4-CF 3 HHHHO 3-F 4-SCF 3 4-OCF 3 HHHHO 3-F 4-SCH 3 4-Cl HHHHO 3-F 4-SOCH 3 4-CF 3 HHHHO 3-F 4-SO 2 CH 3 4-OCF 3 HHHHO 3- F 4-OSO 2 CH 3 4-Cl HHHHO 3-F 4-NHCOCH 3 4-CF 3 HHHHO 3-F 4-NHSO 2 CH 3 4-OCF 3 HHHHO 3-F 2, 4-Cl 2 4-Cl HHHHO 3-F 3-OCF 2 O-4 4-CF 3 ───────────────────────────── ───────
【００７５】[0075]
【表４１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-OCHF2 3-F 4-Cl H H H H O 3-OCHF2 4-Cl 4-CF3 H H H H O 3-OCHF2 4-Br 4-OCF3 H H H H O 3-OCHF2 4-CN 4-Cl H H H H O 3-OCHF2 4-NO2 4-CF3 H H H H O 3-OCHF2 4-CH3 4-OCF3 H H H H O 3-OCHF2 4-CF3 4-Cl H H H H O 3-OCHF2 4-OCH2CH3 4-CF3 H H H H O 3-OCHF2 4-OCHF2 4-OCF3 H H H H O 3-OCHF2 4-OCH2CF3 4-Cl H H H H O 3-OCHF2 4-OCF2Br 4-CF3 H H H H O 3-OCHF2 4-OCF2CHF2 4-OCF3 H H H H O 3-OCHF2 4-OSO2CF3 4-Cl H H H H O 3-OCHF2 4-SCHF2 4-CF3 H H H H O 3-OCHF2 4-SCF3 4-OCF3 H H H H O 3-OCHF2 4-SCH3 4-Cl H H H H O 3-OCHF2 4-SOCH3 4-CF3 H H H H O 3-OCHF2 4-SO2CH3 4-OCF3 H H H H O 3-OCHF2 4-OSO2CH3 4-Cl H H H H O 3-OCHF2 4-NHCOCH3 4-CF3 H H H H O 3-OCHF2 4-NHSO2CH3 4-OCF3 H H H H O 3-OCHF2 2,4-Cl2 4-Cl H H H H O 3-OCHF2 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 41] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-OCHF 2 3-F 4-Cl HHHHO 3-OCHF 2 4-Cl 4-CF 3 HHHHO 3-OCHF 2 4-Br 4-OCF 3 HHHHO 3-OCHF 2 4-CN 4-Cl HHHHO 3-OCHF 2 4-NO 2 4-CF 3 HHHHO 3- OCHF 2 4-CH 3 4-OCF 3 HHHHO 3-OCHF 2 4-CF 3 4-Cl HHHHO 3-OCHF 2 4-OCH 2 CH 3 4-CF 3 HHHHO 3-OCHF 2 4-OCHF 2 4-OCF 3 HHHHO 3-OCHF 2 4-OCH 2 CF 3 4-Cl HHHHO 3-OCHF 2 4-OCF 2 Br 4-CF 3 HHHHO 3-OCHF 2 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-OCHF 2 4- OSO 2 CF 3 4-Cl HHHHO 3-OCHF 2 4-SCHF 2 4-CF 3 HHHHO 3-OCHF 2 4-SCF 3 4-OCF 3 HHHHO 3-OCHF 2 4-SCH 3 4-Cl HHHHO 3-OCHF 2 4-SOCH 3 4-CF 3 HHHHO 3-OCHF 2 4-SO 2 CH 3 4-OCF 3 HHHHO 3-OCHF 2 4-OSO 2 CH 3 4-Cl HHHHO 3-OCHF 2 4-NHCOCH 3 4-CF 3 HHHHO 3-OCHF 2 4-NHSO 2 CH 3 4-OCF 3 HHHHO 3-OCHF 2 2,4-Cl 2 4-Cl HHHHO 3-OCHF 2 3-OCF 2 O-4 4-CF 3 ───── ──── ─────────────────────────
【００７６】[0076]
【表４２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-OCHF2 3-F 4-Cl H H H H O 4-OCHF2 4-Cl 4-CF3 H H H H O 4-OCHF2 4-Br 4-OCF3 H H H H O 4-OCHF2 4-CN 4-Cl H H H H O 4-OCHF2 4-NO2 4-CF3 H H H H O 4-OCHF2 4-CH3 4-OCF3 H H H H O 4-OCHF2 4-CF3 4-Cl H H H H O 4-OCHF2 4-OCH2CH3 4-CF3 H H H H O 4-OCHF2 4-OCHF2 4-OCF3 H H H H O 4-OCHF2 4-OCH2CF3 4-Cl H H H H O 4-OCHF2 4-OCF2Br 4-CF3 H H H H O 4-OCHF2 4-OCF2CHF2 4-OCF3 H H H H O 4-OCHF2 4-OSO2CF3 4-Cl H H H H O 4-OCHF2 4-SCHF2 4-CF3 H H H H O 4-OCHF2 4-SCF3 4-OCF3 H H H H O 4-OCHF2 4-SCH3 4-Cl H H H H O 4-OCHF2 4-SOCH3 4-CF3 H H H H O 4-OCHF2 4-SO2CH3 4-OCF3 H H H H O 4-OCHF2 4-OSO2CH3 4-Cl H H H H O 4-OCHF2 4-NHCOCH3 4-CF3 H H H H O 4-OCHF2 4-NHSO2CH3 4-OCF3 H H H H O 4-OCHF2 2,4-Cl2 4-Cl H H H H O 4-OCHF2 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 42] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-OCHF 2 3-F 4-Cl HHHHO 4-OCHF 2 4-Cl 4-CF 3 HHHHO 4-OCHF 2 4-Br 4-OCF 3 HHHHO 4-OCHF 2 4-CN 4-Cl HHHHO 4-OCHF 2 4-NO 2 4-CF 3 HHHHO 4- OCHF 2 4-CH 3 4-OCF 3 HHHHO 4-OCHF 2 4-CF 3 4-Cl HHHHO 4-OCHF 2 4-OCH 2 CH 3 4-CF 3 HHHHO 4-OCHF 2 4-OCHF 2 4-OCF 3 HHHHO 4-OCHF 2 4-OCH 2 CF 3 4-Cl HHHHO 4-OCHF 2 4-OCF 2 Br 4-CF 3 HHHHO 4-OCHF 2 4-OCF 2 CHF 2 4-OCF 3 HHHHO 4-OCHF 2 4- OSO 2 CF 3 4-Cl HHHHO 4-OCHF 2 4-SCHF 2 4-CF 3 HHHHO 4-OCHF 2 4-SCF 3 4-OCF 3 HHHHO 4-OCHF 2 4-SCH 3 4-Cl HHHHO 4-OCHF 2 4-SOCH 3 4-CF 3 HHHHO 4-OCHF 2 4-SO 2 CH 3 4-OCF 3 HHHHO 4-OCHF 2 4-OSO 2 CH 3 4-Cl HHHHO 4-OCHF 2 4-NHCOCH 3 4-CF 3 HHHHO 4-OCHF 2 4-NHSO 2 CH 3 4-OCF 3 HHHHO 4-OCHF 2 2,4-Cl 2 4-Cl HHHHO 4-OCHF 2 3-OCF 2 O-4 4-CF 3 ───── ──── ─────────────────────────
【００７７】[0077]
【表４３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-Cl H 4-Cl H H H H O 3-Cl 4-Cl 4-CF3 H H H H O 3-Cl 4-Br 4-OCF3 H H H H O 3-Cl 4-CN 4-Cl H H H H O 3-Cl 4-NO2 4-CF3 H H H H O 3-Cl 4-CH3 4-OCF3 H H H H O 3-Cl 4-CF3 4-Cl H H H H O 3-Cl 4-OCH2CH3 4-CF3 H H H H O 3-Cl 4-OCHF2 4-OCF3 H H H H O 3-Cl 4-OCH2CF3 4-Cl H H H H O 3-Cl 4-OCF2Br 4-CF3 H H H H O 3-Cl 4-OCF2CHF2 4-OCF3 H H H H O 3-Cl 4-OSO2CF3 4-Cl H H H H O 3-Cl 4-SCHF2 4-CF3 H H H H O 3-Cl 4-SCF3 4-OCF3 H H H H O 3-Cl 4-SCH3 4-Cl H H H H O 3-Cl 4-SOCH3 4-CF3 H H H H O 3-Cl 4-SO2CH3 4-OCF3 H H H H O 3-Cl 4-OSO2CH3 4-Cl H H H H O 3-Cl 4-NHCOCH3 4-CF3 H H H H O 3-Cl 4-NHSO2CH3 4-OCF3 H H H H O 3-Cl 2,4-Cl2 4-Cl H H H H O 3-Cl 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 43] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-Cl H 4-Cl HHHHO 3-Cl 4-Cl 4-CF 3 HHHHO 3-Cl 4-Br 4-OCF 3 HHHHO 3-Cl 4-CN 4-Cl HHHHO 3-Cl 4-NO 2 4-CF 3 HHHHO 3-Cl 4-CH 3 4- OCF 3 HHHHO 3-Cl 4-CF 3 4-Cl HHHHO 3-Cl 4-OCH 2 CH 3 4-CF 3 HHHHO 3-Cl 4-OCHF 2 4-OCF 3 HHHHO 3-Cl 4-OCH 2 CF 3 4 -Cl HHHHO 3-Cl 4-OCF 2 Br 4-CF 3 HHHHO 3-Cl 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-Cl 4-OSO 2 CF 3 4-Cl HHHHO 3-Cl 4-SCHF 2 4-CF 3 HHHHO 3-Cl 4-SCF 3 4-OCF 3 HHHHO 3-Cl 4-SCH 3 4-Cl HHHHO 3-Cl 4-SOCH 3 4-CF 3 HHHHO 3-Cl 4-SO 2 CH 3 4 -OCF 3 HHHHO 3-Cl 4- OSO 2 CH 3 4-Cl HHHHO 3-Cl 4-NHCOCH 3 4-CF 3 HHHHO 3-Cl 4-NHSO 2 CH 3 4-OCF 3 HHHHO 3-Cl 2,4- Cl 2 4-Cl HHHHO 3-Cl 3-OCF 2 O-4 4-CF 3 ─────────────────────────────── ─────
【００７８】[0078]
【表４４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-Br H 4-Cl H H H H O 3-Br 4-Cl 4-CF3 H H H H O 3-Br 4-Br 4-OCF3 H H H H O 3-Br 4-CN 4-Cl H H H H O 3-Br 4-NO2 4-CF3 H H H H O 3-Br 4-CH3 4-OCF3 H H H H O 3-Br 4-CF3 4-Cl H H H H O 3-Br 4-OCH2CH3 4-CF3 H H H H O 3-Br 4-OCHF2 4-OCF3 H H H H O 3-Br 4-OCH2CF3 4-Cl H H H H O 3-Br 4-OCF2Br 4-CF3 H H H H O 3-Br 4-OCF2CHF2 4-OCF3 H H H H O 3-Br 4-OSO2CF3 4-Cl H H H H O 3-Br 4-SCHF2 4-CF3 H H H H O 3-Br 4-SCF3 4-OCF3 H H H H O 3-Br 4-SCH3 4-Cl H H H H O 3-Br 4-SOCH3 4-CF3 H H H H O 3-Br 4-SO2CH3 4-OCF3 H H H H O 3-Br 4-OSO2CH3 4-Cl H H H H O 3-Br 4-NHCOCH3 4-CF3 H H H H O 3-Br 4-NHSO2CH3 4-OCF3 H H H H O 3-Br 2,4-Cl2 4-Cl H H H H O 3-Br 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 44] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-Br H 4-Cl HHHHO 3-Br 4-Cl 4-CF 3 HHHHO 3-Br 4-Br 4-OCF 3 HHHHO 3-Br 4-CN 4-Cl HHHHO 3-Br 4-NO 2 4-CF 3 HHHHO 3-Br 4-CH 3 4- OCF 3 HHHHO 3-Br 4-CF 3 4-Cl HHHHO 3-Br 4-OCH 2 CH 3 4-CF 3 HHHHO 3-Br 4-OCHF 2 4-OCF 3 HHHHO 3-Br 4-OCH 2 CF 3 4 -Cl HHHHO 3-Br 4-OCF 2 Br 4-CF 3 HHHHO 3-Br 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-Br 4-OSO 2 CF 3 4-Cl HHHHO 3-Br 4-SCHF 2 4-CF 3 HHHHO 3-Br 4-SCF 3 4-OCF 3 HHHHO 3-Br 4-SCH 3 4-Cl HHHHO 3-Br 4-SOCH 3 4-CF 3 HHHHO 3-Br 4-SO 2 CH 3 4 -OCF 3 HHHHO 3-Br 4- OSO 2 CH 3 4-Cl HHHHO 3-Br 4-NHCOCH 3 4-CF 3 HHHHO 3-Br 4-NHSO 2 CH 3 4-OCF 3 HHHHO 3-Br 2,4- Cl 2 4-Cl HHHHO 3-Br 3-OCF 2 O-4 4-CF 3 ─────────────────────────────── ─────
【００７９】[0079]
【表４５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3,4-F2 H 4-Cl H H H H O 3,4-F2 4-Cl 4-CF3 H H H H O 3,4-F2 4-Br 4-OCF3 H H H H O 3,4-F2 4-CN 4-Cl H H H H O 3,4-F2 4-NO2 4-CF3 H H H H O 3,4-F2 4-CH3 4-OCF3 H H H H O 3,4-F2 4-CF3 4-Cl H H H H O 3,4-F2 4-OCH2CH3 4-CF3 H H H H O 3,4-F2 4-OCHF2 4-OCF3 H H H H O 3,4-F2 4-OCH2CF3 4-Cl H H H H O 3,4-F2 4-OCF2Br 4-CF3 H H H H O 3,4-F2 4-OCF2CHF2 4-OCF3 H H H H O 3,4-F2 4-OSO2CF3 4-Cl H H H H O 3,4-F2 4-SCHF2 4-CF3 H H H H O 3,4-F2 4-SCF3 4-OCF3 H H H H O 3,4-F2 4-SCH3 4-Cl H H H H O 3,4-F2 4-SOCH3 4-CF3 H H H H O 3,4-F2 4-SO2CH3 4-OCF3 H H H H O 3,4-F2 4-OSO2CH3 4-Cl H H H H O 3,4-F2 4-NHCOCH3 4-CF3 H H H H O 3,4-F2 4-NHSO2CH3 4-OCF3 H H H H O 3,4-F2 2,4-Cl2 4-Cl H H H H O 3,4-F2 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 45] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3,4-F 2 H 4-Cl HHHHO 3,4-F 2 4-Cl 4-CF 3 HHHHO 3,4-F 2 4-Br 4-OCF 3 HHHHO 3,4-F 2 4-CN 4-Cl HHHHO 3,4-F 2 4-NO 2 4-CF 3 HHHHO 3,4-F 2 4-CH 3 4-OCF 3 HHHHO 3,4-F 2 4-CF 3 4-Cl HHHHO 3,4-F 2 4-OCH 2 CH 3 4-CF 3 HHHHO 3,4-F 2 4-OCHF 2 4-OCF 3 HHHHO 3,4-F 2 4-OCH 2 CF 3 4-Cl HHHHO 3,4-F 2 4-OCF 2 Br 4-CF 3 HHHHO 3 , 4-F 2 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3,4-F 2 4-OSO 2 CF 3 4-Cl HHHHO 3,4-F 2 4-SCHF 2 4-CF 3 HHHHO 3,4 -F 2 4-SCF 3 4-OCF 3 HHHHO 3,4-F 2 4-SCH 3 4-Cl HHHHO 3,4-F 2 4-SOCH 3 4-CF 3 HHHHO 3,4-F 2 4-SO 2 CH 3 4-OCF 3 HHHHO 3,4-F 2 4-OSO 2 CH 3 4-Cl HHHHO 3,4-F 2 4-NHCOCH 3 4-CF 3 HHHHO 3,4-F 2 4-NHSO 2 CH 3 4-OCF 3 HHHHO 3,4-F 2 2,4-Cl 2 4-Cl HHHHO 3,4-F 2 3-OCF 2 O-4 4-CF 3 ──────────── ────── ─────────────────
【００８０】[0080]
【表４６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-Cl 4-F 4-Cl H H H H O 4-Cl 4-Cl 4-CF3 H H H H O 4-Cl 4-Br 4-OCF3 H H H H O 4-Cl 4-CN 4-Cl H H H H O 4-Cl 4-NO2 4-CF3 H H H H O 4-Cl 4-CH3 4-OCF3 H H H H O 4-Cl 4-CF3 4-Cl H H H H O 4-Cl 4-OCH2CH3 4-CF3 H H H H O 4-Cl 4-OCHF2 4-OCF3 H H H H O 4-Cl 4-OCH2CF3 4-Cl H H H H O 4-Cl 4-OCF2Br 4-CF3 H H H H O 4-Cl 4-OCF2CHF2 4-OCF3 H H H H O 4-Cl 4-OSO2CF3 4-Cl H H H H O 4-Cl 4-SCHF2 4-CF3 H H H H O 4-Cl 4-SCF3 4-OCF3 H H H H O 4-Cl 4-SCH3 4-Cl H H H H O 4-Cl 4-SOCH3 4-CF3 H H H H O 4-Cl 4-SO2CH3 4-OCF3 H H H H O 4-Cl 4-OSO2CH3 4-Cl H H H H O 4-Cl 4-NHCOCH3 4-CF3 H H H H O 4-Cl 4-NHSO2CH3 4-OCF3 H H H H O 4-Cl 2,4-Cl2 4-Cl H H H H O 4-Cl 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 46] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-Cl 4-F 4-Cl HHHHO 4 -Cl 4-Cl 4-CF 3 HHHHO 4-Cl 4-Br 4-OCF 3 HHHHO 4-Cl 4-CN 4-Cl HHHHO 4-Cl 4-NO 2 4-CF 3 HHHHO 4-Cl 4-CH 3 4-OCF 3 HHHHO 4-Cl 4-CF 3 4-Cl HHHHO 4-Cl 4-OCH 2 CH 3 4-CF 3 HHHHO 4-Cl 4-OCHF 2 4-OCF 3 HHHHO 4-Cl 4-OCH 2 CF 3 4-Cl HHHHO 4-Cl 4-OCF 2 Br 4-CF 3 HHHHO 4-Cl 4-OCF 2 CHF 2 4-OCF 3 HHHHO 4-Cl 4-OSO 2 CF 3 4-Cl HHHHO 4-Cl 4- SCHF 2 4-CF 3 HHHHO 4-Cl 4-SCF 3 4-OCF 3 HHHHO 4-Cl 4-SCH 3 4-Cl HHHHO 4-Cl 4-SOCH 3 4-CF 3 HHHHO 4-Cl 4-SO 2 CH 3 4-OCF 3 HHHHO 4-Cl 4-OSO 2 CH 3 4-Cl HHHHO 4-Cl 4-NHCOCH 3 4-CF 3 HHHHO 4-Cl 4-NHSO 2 CH 3 4-OCF 3 HHHHO 4-Cl 2, 4-Cl 2 4-Cl HHHHO 4-Cl 3-OCF 2 O-4 4-CF 3 ───────────────────────────── ───────
【００８１】[0081]
【表４７】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 2-F 4-F 4-Cl H H H H O 2-Cl 4-F 4-CF3 H H H H O 4-Cl 4-F 4-OCF3 H H H H O 4-Br 4-F 4-Cl H H H H O 3-I 4-F 4-CF3 H H H H O 4-I 4-F 4-OCF3 H H H H O 3-CH3 4-F 4-Cl H H H H O 4-CH3 4-F 4-CF3 H H H H O 4-CH2CH3 4-F 4-OCF3 H H H H O 3-CH(CH3)2 4-F 4-Cl H H H H O 4-CH2CH2CH2CH3 4-F 4-CF3 H H H H O 4-C(CH3)3 4-F 4-OCF3 H H H H O 3-CH2CH=CH2 4-F 4-Cl H H H H O 4-Q1 4-F 4-CF3 H H H H O 4-Q2 4-F 4-OCF3 H H H H O 4-Q3 4-F 4-Cl H H H H O 4-Q4 4-F 4-CF3 H H H H O 3-CHF2 4-F 4-OCF3 H H H H O 4-CHF2 4-F 4-Cl H H H H O 3-CH2Br 4-F 4-CF3 H H H H O 3-CH2Cl 4-F 4-OCF3 H H H H O 2-CF3 4-F 4-Cl H H H H O 4-CF3 4-F 4-CF3 ───────────────────────────────────[Table 47] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 2-F 4-F 4-Cl HHHHO 2 -Cl 4-F 4-CF 3 HHHHO 4-Cl 4-F 4-OCF 3 HHHHO 4-Br 4-F 4-Cl HHHHO 3-I 4-F 4-CF 3 HHHHO 4-I 4-F 4- OCF 3 HHHHO 3-CH 3 4-F 4-Cl HHHHO 4-CH 3 4-F 4-CF 3 HHHHO 4-CH 2 CH 3 4-F 4-OCF 3 HHHHO 3-CH (CH 3 ) 2 4- F 4-Cl HHHHO 4-CH 2 CH 2 CH 2 CH 3 4-F 4-CF 3 HHHHO 4-C (CH 3 ) 3 4-F 4-OCF 3 HHHHO 3-CH 2 CH = CH 2 4-F 4-Cl HHHHO 4-Q1 4-F 4-CF 3 HHHHO 4-Q2 4-F 4-OCF 3 HHHHO 4-Q3 4-F 4-Cl HHHHO 4-Q4 4-F 4-CF 3 HHHHO 3-CHF 2 4-F 4-OCF 3 HHHHO 4-CHF 2 4-F 4-Cl HHHHO 3-CH 2 Br 4-F 4-CF 3 HHHHO 3-CH 2 Cl 4-F 4-OCF 3 HHHHO 2-CF 3 4-F 4-Cl HHHHO 4-CF 3 4-F 4-CF 3 ───────────────────────────────── ───
【００８２】[0082]
【表４８】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-CH2CN 4-F 4-Cl H H H H O 4-CH2OH 4-F 4-CF3 H H H H O 4-CH2CO2H 4-F 4-OCF3 H H H H O 3-OCH3 4-F 4-Cl H H H H O 4-OCH3 4-F 4-CF3 H H H H O 3-OCH2CH3 4-F 4-OCF3 H H H H O 4-OCH(CH3)2 4-F 4-Cl H H H H O 4-OC(CH3)3 4-F 4-CF3 H H H H O 2-OCHF2 4-F 4-OCF3 H H H H O 3-OCF2Br 4-F 4-Cl H H H H O 4-OCF2Br 4-F 4-CF3 H H H H O 4-OCF3 4-F 4-OCF3 H H H H O 3-OCH2CF3 4-F 4-Cl H H H H O 4-OCH2CF3 4-F 4-CF3 H H H H O 3-OCF2CF3 4-F 4-OCF3 H H H H O 4-OCF2CF3 4-F 4-Cl H H H H O 2-OCF2CHF2 4-F 4-CF3 H H H H O 4-OCF2CHF2 4-F 4-OCF3 H H H H O 3-OCF2CHFCl 4-F 4-Cl H H H H O 4-OCF2CHFBr 4-F 4-CF3 H H H H O 3-OCF2CF2CF3 4-F 4-OCF3 H H H H O 3-OCH2CH=CHCl 4-F 4-Cl H H H H O 3-O(Q1-2,2-Cl2) 4-F 4-CF3 ───────────────────────────────────[Table 48] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-CH 2 CN 4-F 4-Cl HHHHO 4-CH 2 OH 4-F 4-CF 3 HHHHO 4-CH 2 CO 2 H 4-F 4-OCF 3 HHHHO 3-OCH 3 4-F 4-Cl HHHHO 4-OCH 3 4-F 4-CF 3 HHHHO 3-OCH 2 CH 3 4-F 4-OCF 3 HHHHO 4-OCH (CH 3 ) 2 4-F 4-Cl HHHHO 4-OC (CH 3 ) 3 4-F 4-CF 3 HHHHO 2-OCHF 2 4-F 4-OCF 3 HHHHO 3-OCF 2 Br 4-F 4-Cl HHHHO 4-OCF 2 Br 4-F 4-CF 3 HHHHO 4-OCF 3 4-F 4-OCF 3 HHHHO 3-OCH 2 CF 3 4-F 4-Cl HHHHO 4-OCH 2 CF 3 4-F 4-CF 3 HHHHO 3-OCF 2 CF 3 4-F 4-OCF 3 HHHHO 4-OCF 2 CF 3 4-F 4-Cl HHHHO 2-OCF 2 CHF 2 4-F 4-CF 3 HHHHO 4-OCF 2 CHF 2 4-F 4-OCF 3 HHHHO 3-OCF 2 CHFCl 4-F 4-Cl HHHHO 4-OCF 2 CHFBr 4-F 4- CF 3 HHHHO 3-OCF 2 CF 2 CF 3 4-F 4-OCF 3 HHHHO 3-OCH 2 CH = CHCl 4-F 4-Cl HHHHO 3-O (Q1-2,2-Cl 2 ) 4-F 4 -CF 3 ─────────────────────── ───────────
【００８３】[0083]
【表４９】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-SCH3 4-F 4-Cl H H H H O 4-SCH3 4-F 4-CF3 H H H H O 3-SCHF2 4-F 4-OCF3 H H H H O 4-SCHF2 4-F 4-Cl H H H H O 3-SCF3 4-F 4-CF3 H H H H O 4-SCF3 4-F 4-OCF3 H H H H O 3-SOCH3 4-F 4-Cl H H H H O 4-SOCH3 4-F 4-CF3 H H H H O 3-SO2CH3 4-F 4-OCF3 H H H H O 4-SO2CH3 4-F 4-Cl H H H H O 3-SO2CHF2 4-F 4-CF3 H H H H O 4-CH2OCH3 4-F 4-OCF3 H H H H O 3-OCF2CHFOCF3 4-F 4-Cl H H H H O 4-OCF2CHFOCF3 4-F 4-CF3 H H H H O 4-CH2COCH3 4-F 4-OCF3 H H H H O 4-CH2CO2CH3 4-F 4-Cl H H H H O 4-OCO2CH3 4-F 4-CF3 H H H H O 3-OCOCH3 4-F 4-OCF3 H H H H O 4-COCH3 4-F 4-Cl H H H H O 4-COCF3 4-F 4-CF3 H H H H O 4-CO2CH2CH3 4-F 4-OCF3 H H H H O 4-CO2C(CH3)3 4-F 4-Cl H H H H O 3-CO2CH2CF3 4-F 4-CF3 ───────────────────────────────────[Table 49] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-SCH 3 4-F 4-Cl HHHHO 4-SCH 3 4-F 4-CF 3 HHHHO 3-SCHF 2 4-F 4-OCF 3 HHHHO 4-SCHF 2 4-F 4-Cl HHHHO 3-SCF 3 4-F 4-CF 3 HHHHO 4-SCF 3 4-F 4-OCF 3 HHHHO 3-SOCH 3 4-F 4-Cl HHHHO 4-SOCH 3 4-F 4-CF 3 HHHHO 3-SO 2 CH 3 4-F 4-OCF 3 HHHHO 4-SO 2 CH 3 4-F 4-Cl HHHHO 3-SO 2 CHF 2 4-F 4-CF 3 HHHHO 4-CH 2 OCH 3 4-F 4-OCF 3 HHHHO 3-OCF 2 CHFOCF 3 4-F 4-Cl HHHHO 4-OCF 2 CHFOCF 3 4-F 4-CF 3 HHHHO 4-CH 2 COCH 3 4-F 4-OCF 3 HHHHO 4-CH 2 CO 2 CH 3 4-F 4-Cl HHHHO 4-OCO 2 CH 3 4 -F 4-CF 3 HHHHO 3-OCOCH 3 4-F 4-OCF 3 HHHHO 4-COCH 3 4-F 4-Cl HHHHO 4-COCF 3 4-F 4-CF 3 HHHHO 4-CO 2 CH 2 CH 3 4-F 4-OCF 3 HHHHO 4-CO 2 C (CH 3 ) 3 4-F 4-Cl HHHHO 3-CO 2 CH 2 CF 3 4-F 4-CF 3 ─────────── ────────────────── ──────
【００８４】[0084]
【表５０】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-NO2 4-F 4-Cl H H H H O 4-NO2 4-F 4-CF3 H H H H O 3-CN 4-F 4-OCF3 H H H H O 4-CN 4-F 4-Cl H H H H O 3-OH 4-F 4-CF3 H H H H O 4-OH 4-F 4-OCF3 H H H H O 4-SCN 4-F 4-Cl H H H H O 3-OSO2CH3 4-F 4-CF3 H H H H O 4-OSO2CH3 4-F 4-OCF3 H H H H O 3-OSO2CF3 4-F 4-Cl H H H H O 4-OSO2CF3 4-F 4-CF3 H H H H O 4-CSCH3 4-F 4-OCF3 H H H H O 4-NH2 4-F 4-Cl H H H H O 4-N(CH3)2 4-F 4-CF3 H H H H O 4-CON(CH3)2 4-F 4-OCF3 H H H H O 3-OCON(CH3)2 4-F 4-Cl H H H H O 4-NHCOCH3 4-F 4-CF3 H H H H O 4-SO2N(CH3)2 4-F 4-OCF3 H H H H O 4-Si(CH3)3 4-F 4-Cl H H H H O 4-C6H5 4-F 4-CF3 H H H H O 3-OC6H5 4-F 4-OCF3 H H H H O 4-OC6H5 4-F 4-Cl H H H H O 3-SC6H5 4-F 4-CF3 ───────────────────────────────────[Table 50] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-NO 2 4-F 4-Cl HHHHO 4-NO 2 4-F 4-CF 3 HHHHO 3-CN 4-F 4-OCF 3 HHHHO 4-CN 4-F 4-Cl HHHHO 3-OH 4-F 4-CF 3 HHHHO 4-OH 4-F 4-OCF 3 HHHHO 4-SCN 4-F 4-Cl HHHHO 3-OSO 2 CH 3 4-F 4-CF 3 HHHHO 4-OSO 2 CH 3 4-F 4-OCF 3 HHHHO 3-OSO 2 CF 3 4 -F 4-Cl HHHHO 4-OSO 2 CF 3 4-F 4-CF 3 HHHHO 4-CSCH 3 4-F 4-OCF 3 HHHHO 4-NH 2 4-F 4-Cl HHHHO 4-N (CH 3 ) 2 4-F 4-CF 3 HHHHO 4-CON (CH 3 ) 2 4-F 4-OCF 3 HHHHO 3-OCON (CH 3 ) 2 4-F 4-Cl HHHHO 4-NHCOCH 3 4-F 4-CF 3 HHHHO 4-SO 2 N (CH 3 ) 2 4-F 4-OCF 3 HHHHO 4-Si (CH 3 ) 3 4-F 4-Cl HHHHO 4-C 6 H 5 4-F 4-CF 3 HHHHO 3 -OC 6 H 5 4-F 4-OCF 3 HHHHO 4-OC 6 H 5 4-F 4-Cl HHHHO 3-SC 6 H 5 4-F 4-CF 3 ──────────── ────────────────────────
【００８５】[0085]
【表５１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3-SO2C6H5 4-F 4-Cl H H H H O 3-NHC6H5 4-F 4-CF3 H H H H O 3-CH2C6H5 4-F 4-OCF3 H H H H O 3-COC6H5 4-F 4-Cl H H H H O 3-NHSO2CH3 4-F 4-CF3 H H H H O 2-CH=CH-CH=CH-3 4-F 4-OCF3 H H H H O 3-CH=CH-CH=CH-4 4-F 4-Cl H H H H O 3-OCH2O-4 4-F 4-CF3 H H H H O 3-OCF2O-4 4-F 4-OCF3 H H H H O 3-OCH2CH2O-4 4-F 4-Cl H H H H O 3-OCF2CF2O-4 4-F 4-CF3 H H H H O 2,3-F2 4-F 4-OCF3 H H H H O 2,4-F2 4-F 4-Cl H H H H O 2,5-F2 4-F 4-CF3 H H H H O 3,5-F2 4-F 4-OCF3 H H H H O 3,4-Cl2 4-F 4-Cl H H H H O 3,5-Cl2 4-F 4-CF3 H H H H O 3,4-Br2 4-F 4-OCF3 H H H H O 3,5-I2 4-F 4-Cl H H H H O 2,4-(CH3)2 4-F 4-CF3 H H H H O 3,4-(OCH3)2 4-F 4-OCF3 H H H H O 3,4-(OCF3)2 4-F 4-Cl H H H H O 3,5-(OCHF2)2 4-F 4-CF3 ───────────────────────────────────[Table 51] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3-SO 2 C 6 H 5 4-F 4-Cl HHHHO 3-NHC 6 H 5 4-F 4-CF 3 HHHHO 3-CH 2 C 6 H 5 4-F 4-OCF 3 HHHHO 3-COC 6 H 5 4-F 4-Cl HHHHO 3-NHSO 2 CH 3 4-F 4-CF 3 HHHHO 2-CH = CH-CH = CH-3 4-F 4-OCF 3 HHHHO 3-CH = CH-CH = CH-4 4-F 4-Cl HHHHO 3- OCH 2 O-4 4-F 4-CF 3 HHHHO 3-OCF 2 O-4 4-F 4-OCF 3 HHHHO 3-OCH 2 CH 2 O-4 4-F 4-Cl HHHHO 3-OCF 2 CF 2 O-4 4-F 4-CF 3 HHHHO 2,3-F 2 4-F 4-OCF 3 HHHHO 2,4-F 2 4-F 4-Cl HHHHO 2,5-F 2 4-F 4-CF 3 HHHHO 3,5-F 2 4-F 4-OCF 3 HHHHO 3,4-Cl 2 4-F 4-Cl HHHHO 3,5-Cl 2 4-F 4-CF 3 HHHHO 3,4-Br 2 4 -F 4-OCF 3 HHHHO 3,5-I 2 4-F 4-Cl HHHHO 2,4- (CH 3 ) 2 4-F 4-CF 3 HHHHO 3,4- (OCH 3 ) 2 4-F 4 -OCF 3 HHHHO 3,4- (OCF 3 ) 2 4-F 4-Cl HHHHO 3,5- (OCHF 2 ) 2 4-F 4-CF 3 ─────────────── ─────────── ─────────
【００８６】[0086]
【表５２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 3,4-(CF3)2 4-F 4-Cl H H H H O 3,5-(CF3)2 4-F 4-CF3 H H H H O 2-F-4-Cl 4-F 4-OCF3 H H H H O 3-F-5-Cl 4-F 4-Cl H H H H O 3-F-5-CF3 4-F 4-CF3 H H H H O 3-F-5-OCHF2 4-F 4-OCF3 H H H H O 3-Cl-5-CF3 4-F 4-Cl H H H H O 3-Cl-4-OCHF2 4-F 4-CF3 H H H H O 3-Cl-4-CN 4-F 4-OCF3 H H H H O 3-Cl-4-F 4-F 4-Cl H H H H O 3-Cl-5-OSO2CF3 4-F 4-CF3 H H H H O 3-F-4-OSO2CF3 4-F 4-OCF3 H H H H O 2,3,4-F3 4-F 4-Cl H H H H O 3,4,5-F3 4-F 4-CF3 H H H H O 2,4,5-Cl3 4-F 4-OCF3 H H H H O 2,4,6-Cl3 4-F 4-Cl H H H H O 2-F-4,5-Cl2 4-F 4-CF3 H H H H O 3,5-Cl2-4-CF3 4-F 4-OCF3 H H H H O 2,3,4,5-F4 4-F 4-Cl H H H H O 2,3,5,6-F4 4-F 4-CF3 H H H H O 2,4-F2-3,5-Cl2 4-F 4-OCF3 H H H H O 2,3,4,5,6-F5 4-F 4-Cl H H H H O 2,3,5,6-F4-4-CN 4-F 4-CF3 ───────────────────────────────────[Table 52] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 3,4- (CF 3 ) 2 4- F 4-Cl HHHHO 3,5- (CF 3 ) 2 4-F 4-CF 3 HHHHO 2-F-4-Cl 4-F 4-OCF 3 HHHHO 3-F-5-Cl 4-F 4-Cl HHHHO 3-F-5-CF 3 4-F 4-CF 3 HHHHO 3-F-5-OCHF 2 4-F 4-OCF 3 HHHHO 3-Cl-5-CF 3 4-F 4-Cl HHHHO 3- Cl-4-OCHF 2 4-F 4-CF 3 HHHHO 3-Cl-4-CN 4-F 4-OCF 3 HHHHO 3-Cl-4-F 4-F 4-Cl HHHHO 3-Cl-5-OSO 2 CF 3 4-F 4-CF 3 HHHHO 3-F-4-OSO 2 CF 3 4-F 4-OCF 3 HHHHO 2,3,4-F 3 4-F 4-Cl HHHHO 3,4,5- F 3 4-F 4-CF 3 HHHHO 2,4,5-Cl 3 4-F 4-OCF 3 HHHHO 2,4,6-Cl 3 4-F 4-Cl HHHHO 2-F-4,5-Cl 2 4-F 4-CF 3 HHHHO 3,5-Cl 2 -4-CF 3 4-F 4-OCF 3 HHHHO 2,3,4,5-F 4 4-F 4-Cl HHHHO 2,3,5 , 6-F 4 4-F 4-CF 3 HHHHO 2,4-F 2 -3,5-Cl 2 4-F 4-OCF 3 HHHHO 2,3,4,5,6-F 5 4-F 4 -Cl HHHHO 2,3,5,6-F 4 -4- CN 4-F 4-CF 3 ───────────────────── ─────────────
【００８７】[0087]
【表５３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 4-Cl 4-Cl H H H H O 3-Cl 4-Cl 4-CF3 H H H H O 4-Cl 4-Cl 4-OCF3 H H H H O 3-Br 4-Cl 4-Cl H H H H O 3-CH3 4-Cl 4-CF3 H H H H O 4-CF3 4-Cl 4-OCF3 H H H H O 3-OCH3 4-Cl 4-Cl H H H H O 3-OCHF2 4-Cl 4-CF3 H H H H O 4-OCHF2 4-Cl 4-OCF3 H H H H O 3-OCF2Br 4-Cl 4-Cl H H H H O 3-OCF3 4-Cl 4-CF3 H H H H O 3-OCH2CF3 4-Cl 4-OCF3 H H H H O 3-OCF2CHF2 4-Cl 4-Cl H H H H O 3-SCHF2 4-Cl 4-CF3 H H H H O 3-SCF3 4-Cl 4-OCF3 H H H H O 3-NO2 4-Cl 4-Cl H H H H O 3-CN 4-Cl 4-CF3 H H H H O 3-OSO2CH3 4-Cl 4-OCF3 H H H H O 3-OSO2CF3 4-Cl 4-Cl H H H H O 4-OSO2CF3 4-Cl 4-CF3 H H H H O 3,4-F2 4-Cl 4-OCF3 H H H H O 3,5-F2 4-Cl 4-Cl H H H H O 3-Cl-4-F 4-Cl 4-CF3 ───────────────────────────────────[Table 53] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 4-Cl 4-Cl HHHHO 3 -Cl 4-Cl 4-CF 3 HHHHO 4-Cl 4-Cl 4-OCF 3 HHHHO 3-Br 4-Cl 4-Cl HHHHO 3-CH 3 4-Cl 4-CF 3 HHHHO 4-CF 3 4-Cl 4-OCF 3 HHHHO 3-OCH 3 4-Cl 4-Cl HHHHO 3-OCHF 2 4-Cl 4-CF 3 HHHHO 4-OCHF 2 4-Cl 4-OCF 3 HHHHO 3-OCF 2 Br 4-Cl 4- Cl HHHHO 3-OCF 3 4-Cl 4-CF 3 HHHHO 3-OCH 2 CF 3 4-Cl 4-OCF 3 HHHHO 3-OCF 2 CHF 2 4-Cl 4-Cl HHHHO 3-SCHF 2 4-Cl 4- CF 3 HHHHO 3-SCF 3 4-Cl 4-OCF 3 HHHHO 3-NO 2 4-Cl 4-Cl HHHHO 3-CN 4-Cl 4-CF 3 HHHHO 3-OSO 2 CH 3 4-Cl 4-OCF 3 HHHHO 3-OSO 2 CF 3 4-Cl 4-Cl HHHHO 4-OSO 2 CF 3 4-Cl 4-CF 3 HHHHO 3,4-F 2 4-Cl 4-OCF 3 HHHHO 3,5-F 2 4- Cl 4-Cl HHHHO 3-Cl-4-F 4-Cl 4-CF 3 ──────────────────────────────── ────
【００８８】[0088]
【表５４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 4-Br 4-Cl H H H H O 3-Cl 4-Br 4-CF3 H H H H O 4-Cl 4-Br 4-OCF3 H H H H O 3-Br 4-Br 4-Cl H H H H O 3-CH3 4-Br 4-CF3 H H H H O 4-CF3 4-Br 4-OCF3 H H H H O 3-OCH3 4-Br 4-Cl H H H H O 3-OCHF2 4-Br 4-CF3 H H H H O 4-OCHF2 4-Br 4-OCF3 H H H H O 3-OCF2Br 4-Br 4-Cl H H H H O 3-OCF3 4-Br 4-CF3 H H H H O 3-OCH2CF3 4-Br 4-OCF3 H H H H O 3-OCF2CHF2 4-Br 4-Cl H H H H O 3-SCHF2 4-Br 4-CF3 H H H H O 3-SCF3 4-Br 4-OCF3 H H H H O 3-NO2 4-Br 4-Cl H H H H O 3-CN 4-Br 4-CF3 H H H H O 3-OSO2CH3 4-Br 4-OCF3 H H H H O 3-OSO2CF3 4-Br 4-Cl H H H H O 4-OSO2CF3 4-Br 4-CF3 H H H H O 3,4-F2 4-Br 4-OCF3 H H H H O 3,5-F2 4-Br 4-Cl H H H H O 3-Cl-4-F 4-Br 4-CF3 ───────────────────────────────────[Table 54] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 4-Br 4-Cl HHHHO 3 -Cl 4-Br 4-CF 3 HHHHO 4-Cl 4-Br 4-OCF 3 HHHHO 3-Br 4-Br 4-Cl HHHHO 3-CH 3 4-Br 4-CF 3 HHHHO 4-CF 3 4-Br 4-OCF 3 HHHHO 3-OCH 3 4-Br 4-Cl HHHHO 3-OCHF 2 4-Br 4-CF 3 HHHHO 4-OCHF 2 4-Br 4-OCF 3 HHHHO 3-OCF 2 Br 4-Br 4- Cl HHHHO 3-OCF 3 4-Br 4-CF 3 HHHHO 3-OCH 2 CF 3 4-Br 4-OCF 3 HHHHO 3-OCF 2 CHF 2 4-Br 4-Cl HHHHO 3-SCHF 2 4-Br 4- CF 3 HHHHO 3-SCF 3 4-Br 4-OCF 3 HHHHO 3-NO 2 4-Br 4-Cl HHHHO 3-CN 4-Br 4-CF 3 HHHHO 3-OSO 2 CH 3 4-Br 4-OCF 3 HHHHO 3-OSO 2 CF 3 4-Br 4-Cl HHHHO 4-OSO 2 CF 3 4-Br 4-CF 3 HHHHO 3,4-F 2 4-Br 4-OCF 3 HHHHO 3,5-F 2 4- Br 4-Cl HHHHO 3-Cl-4-F 4-Br 4-CF 3 ──────────────────────────────── ────
【００８９】[0089]
【表５５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 4-CN 4-Cl H H H H O 2-Cl 4-CN 4-CF3 H H H H O 4-Cl 4-CN 4-OCF3 H H H H O 3-Br 4-CN 4-Cl H H H H O 3-CH3 4-CN 4-CF3 H H H H O 4-CF3 4-CN 4-OCF3 H H H H O 3-OCH3 4-CN 4-Cl H H H H O 3-OCHF2 4-CN 4-CF3 H H H H O 4-OCHF2 4-CN 4-OCF3 H H H H O 3-OCF2Br 4-CN 4-Cl H H H H O 3-OCF3 4-CN 4-CF3 H H H H O 3-OCH2CF3 4-CN 4-OCF3 H H H H O 3-OCF2CHF2 4-CN 4-Cl H H H H O 3-SCHF2 4-CN 4-CF3 H H H H O 3-SCF3 4-CN 4-OCF3 H H H H O 3-NO2 4-CN 4-Cl H H H H O 3-CN 4-CN 4-CF3 H H H H O 3-OSO2CH3 4-CN 4-OCF3 H H H H O 3-OSO2CF3 4-CN 4-Cl H H H H O 4-OSO2CF3 4-CN 4-CF3 H H H H O 3,4-F2 4-CN 4-OCF3 H H H H O 3,5-F2 4-CN 4-Cl H H H H O 3-Cl-4-F 4-CN 4-CF3 ───────────────────────────────────[Table 55] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 4-CN 4-Cl HHHHO 2 -Cl 4-CN 4-CF 3 HHHHO 4-Cl 4-CN 4-OCF 3 HHHHO 3-Br 4-CN 4-Cl HHHHO 3-CH 3 4-CN 4-CF 3 HHHHO 4-CF 3 4-CN 4-OCF 3 HHHHO 3-OCH 3 4-CN 4-Cl HHHHO 3-OCHF 2 4-CN 4-CF 3 HHHHO 4-OCHF 2 4-CN 4-OCF 3 HHHHO 3-OCF 2 Br 4-CN 4- Cl HHHHO 3-OCF 3 4-CN 4-CF 3 HHHHO 3-OCH 2 CF 3 4-CN 4-OCF 3 HHHHO 3-OCF 2 CHF 2 4-CN 4-Cl HHHHO 3-SCHF 2 4-CN 4- CF 3 HHHHO 3-SCF 3 4-CN 4-OCF 3 HHHHO 3-NO 2 4-CN 4-Cl HHHHO 3-CN 4-CN 4-CF 3 HHHHO 3-OSO 2 CH 3 4-CN 4-OCF 3 HHHHO 3-OSO 2 CF 3 4-CN 4-Cl HHHHO 4-OSO 2 CF 3 4-CN 4-CF 3 HHHHO 3,4-F 2 4-CN 4-OCF 3 HHHHO 3,5-F 2 4- CN 4-Cl HHHHO 3-Cl-4-F 4-CN 4-CF 3 ──────────────────────────────── ────
【００９０】[0090]
【表５６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 4-OHCF2 4-Cl H H H H O 3-Cl 4-OHCF2 4-CF3 H H H H O 4-Cl 4-OHCF2 4-OCF3 H H H H O 3-Br 4-OHCF2 4-Cl H H H H O 3-CH3 4-OHCF2 4-CF3 H H H H O 4-CF3 4-OHCF2 4-OCF3 H H H H O 3-OCH3 4-OHCF2 4-Cl H H H H O 3-OCHF2 4-OHCF2 4-CF3 H H H H O 4-OCHF2 4-OHCF2 4-OCF3 H H H H O 3-OCF2Br 4-OHCF2 4-Cl H H H H O 3-OCF3 4-OHCF2 4-CF3 H H H H O 3-OCH2CF3 4-OHCF2 4-OCF3 H H H H O 3-OCF2CHF2 4-OHCF2 4-Cl H H H H O 3-SCHF2 4-OHCF2 4-CF3 H H H H O 3-SCF3 4-OHCF2 4-OCF3 H H H H O 3-NO2 4-OHCF2 4-Cl H H H H O 3-CN 4-OHCF2 4-CF3 H H H H O 3-OSO2CH3 4-OHCF2 4-OCF3 H H H H O 3-OSO2CF3 4-OHCF2 4-Cl H H H H O 4-OSO2CF3 4-OHCF2 4-CF3 H H H H O 3,4-F2 4-OHCF2 4-OCF3 H H H H O 3,5-F2 4-OHCF2 4-Cl H H H H O 3-Cl-4-F 4-OHCF2 4-CF3 ───────────────────────────────────[Table 56] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 4-OHCF 2 4-Cl HHHHO 3-Cl 4-OHCF 2 4-CF 3 HHHHO 4-Cl 4-OHCF 2 4-OCF 3 HHHHO 3-Br 4-OHCF 2 4-Cl HHHHO 3-CH 3 4-OHCF 2 4-CF 3 HHHHO 4- CF 3 4-OHCF 2 4-OCF 3 HHHHO 3-OCH 3 4-OHCF 2 4-Cl HHHHO 3-OCHF 2 4-OHCF 2 4-CF 3 HHHHO 4-OCHF 2 4-OHCF 2 4-OCF 3 HHHHO 3 -OCF 2 Br 4-OHCF 2 4-Cl HHHHO 3-OCF 3 4-OHCF 2 4-CF 3 HHHHO 3-OCH 2 CF 3 4-OHCF 2 4-OCF 3 HHHHO 3-OCF 2 CHF 2 4-OHCF 2 4-Cl HHHHO 3-SCHF 2 4-OHCF 2 4-CF 3 HHHHO 3-SCF 3 4-OHCF 2 4-OCF 3 HHHHO 3-NO 2 4-OHCF 2 4-Cl HHHHO 3-CN 4-OHCF 2 4 -CF 3 HHHHO 3-OSO 2 CH 3 4-OHCF 2 4-OCF 3 HHHHO 3-OSO 2 CF 3 4-OHCF 2 4-Cl HHHHO 4-OSO 2 CF 3 4-OHCF 2 4-CF 3 HHHHO 3, 4-F 2 4-OHCF 2 4-OCF 3 HHHHO 3,5-F 2 4-OHCF 2 4-Cl HHHHO 3-Cl-4-F 4-OHCF 2 4-CF 3 ───────── ──────── ────────────────────
【００９１】[0091]
【表５７】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 4-OSO2CF3 4-Cl H H H H O 3-Cl 4-OSO2CF3 4-CF3 H H H H O 4-Cl 4-OSO2CF3 4-OCF3 H H H H O 3-Br 4-OSO2CF3 4-Cl H H H H O 3-CH3 4-OSO2CF3 4-CF3 H H H H O 4-CF3 4-OSO2CF3 4-OCF3 H H H H O 3-OCH3 4-OSO2CF3 4-Cl H H H H O 3-OCHF2 4-OSO2CF3 4-CF3 H H H H O 4-OCHF2 4-OSO2CF3 4-OCF3 H H H H O 3-OCF2Br 4-OSO2CF3 4-Cl H H H H O 3-OCF3 4-OSO2CF3 4-CF3 H H H H O 3-OCH2CF3 4-OSO2CF3 4-OCF3 H H H H O 3-OCF2CHF2 4-OSO2CF3 4-Cl H H H H O 3-SCHF2 4-OSO2CF3 4-CF3 H H H H O 3-SCF3 4-OSO2CF3 4-OCF3 H H H H O 3-NO2 4-OSO2CF3 4-Cl H H H H O 3-CN 4-OSO2CF3 4-CF3 H H H H O 3-OSO2CH3 4-OSO2CF3 4-OCF3 H H H H O 3-OSO2CF3 4-OSO2CF3 4-Cl H H H H O 4-OSO2CF3 4-OSO2CF3 4-CF3 H H H H O 3,4-F2 4-OSO2CF3 4-OCF3 H H H H O 3,5-F2 4-OSO2CF3 4-Cl H H H H O 3-Cl-4-F 4-OSO2CF3 4-CF3 ───────────────────────────────────[Table 57] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 4-OSO 2 CF 3 4- Cl HHHHO 3-Cl 4-OSO 2 CF 3 4-CF 3 HHHHO 4-Cl 4-OSO 2 CF 3 4-OCF 3 HHHHO 3-Br 4-OSO 2 CF 3 4-Cl HHHHO 3-CH 3 4-OSO 2 CF 3 4-CF 3 HHHHO 4-CF 3 4-OSO 2 CF 3 4-OCF 3 HHHHO 3-OCH 3 4-OSO 2 CF 3 4-Cl HHHHO 3-OCHF 2 4-OSO 2 CF 3 4-CF 3 HHHHO 4-OCHF 2 4-OSO 2 CF 3 4-OCF 3 HHHHO 3-OCF 2 Br 4-OSO 2 CF 3 4-Cl HHHHO 3-OCF 3 4-OSO 2 CF 3 4-CF 3 HHHHO 3-OCH 2 CF 3 4-OSO 2 CF 3 4-OCF 3 HHHHO 3-OCF 2 CHF 2 4-OSO 2 CF 3 4-Cl HHHHO 3-SCHF 2 4-OSO 2 CF 3 4-CF 3 HHHHO 3-SCF 3 4 -OSO 2 CF 3 4-OCF 3 HHHHO 3-NO 2 4-OSO 2 CF 3 4-Cl HHHHO 3-CN 4-OSO 2 CF 3 4-CF 3 HHHHO 3-OSO 2 CH 3 4-OSO 2 CF 3 4-OCF 3 HHHHO 3-OSO 2 CF 3 4-OSO 2 CF 3 4-Cl HHHHO 4-OSO 2 CF 3 4-OSO 2 CF 3 4-CF 3 HHHHO 3,4-F 2 4-OSO 2 CF 3 4-OCF 3 HHHHO 3,5-F 2 4-OSO 2 C F 3 4-Cl HHHHO 3-Cl-4-F 4-OSO 2 CF 3 4-CF 3 ──────────────────────────── ────────
【００９２】[0092]
【表５８】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 4-OCF2CHF2 4-Cl H H H H O 3-Cl 4-OCF2CHF2 4-CF3 H H H H O 4-Cl 4-OCF2CHF2 4-OCF3 H H H H O 3-Br 4-OCF2CHF2 4-Cl H H H H O 3-CH3 4-OCF2CHF2 4-CF3 H H H H O 4-CF3 4-OCF2CHF2 4-OCF3 H H H H O 3-OCH3 4-OCF2CHF2 4-Cl H H H H O 3-OCHF2 4-OCF2CHF2 4-CF3 H H H H O 4-OCHF2 4-OCF2CHF2 4-OCF3 H H H H O 3-OCF2Br 4-OCF2CHF2 4-Cl H H H H O 3-OCF3 4-OCF2CHF2 4-CF3 H H H H O 3-OCH2CF3 4-OCF2CHF2 4-OCF3 H H H H O 3-OCF2CHF2 4-OCF2CHF2 4-Cl H H H H O 3-SCHF2 4-OCF2CHF2 4-CF3 H H H H O 3-SCF3 4-OCF2CHF2 4-OCF3 H H H H O 3-NO2 4-OCF2CHF2 4-Cl H H H H O 3-CN 4-OCF2CHF2 4-CF3 H H H H O 3-OSO2CH3 4-OCF2CHF2 4-OCF3 H H H H O 3-OSO2CF3 4-OCF2CHF2 4-Cl H H H H O 4-OSO2CF3 4-OCF2CHF2 4-CF3 H H H H O 3,4-F2 4-OCF2CHF2 4-OCF3 H H H H O 3,5-F2 4-OCF2CHF2 4-Cl H H H H O 3-Cl-4-F 4-OCF2CHF2 4-CF3 ───────────────────────────────────[Table 58] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 4-OCF 2 CHF 2 4- Cl HHHHO 3-Cl 4-OCF 2 CHF 2 4-CF 3 HHHHO 4-Cl 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-Br 4-OCF 2 CHF 2 4-Cl HHHHO 3-CH 3 4-OCF 2 CHF 2 4-CF 3 HHHHO 4-CF 3 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-OCH 3 4-OCF 2 CHF 2 4-Cl HHHHO 3-OCHF 2 4-OCF 2 CHF 2 4-CF 3 HHHHO 4-OCHF 2 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-OCF 2 Br 4-OCF 2 CHF 2 4-Cl HHHHO 3-OCF 3 4-OCF 2 CHF 2 4-CF 3 HHHHO 3-OCH 2 CF 3 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-OCF 2 CHF 2 4-OCF 2 CHF 2 4-Cl HHHHO 3-SCHF 2 4-OCF 2 CHF 2 4-CF 3 HHHHO 3-SCF 3 4 -OCF 2 CHF 2 4-OCF 3 HHHHO 3-NO 2 4-OCF 2 CHF 2 4-Cl HHHHO 3-CN 4-OCF 2 CHF 2 4-CF 3 HHHHO 3-OSO 2 CH 3 4-OCF 2 CHF 2 4-OCF 3 HHHHO 3-OSO 2 CF 3 4-OCF 2 CHF 2 4-Cl HHHHO 4-OSO 2 CF 3 4-OCF 2 CHF 2 4-CF 3 HHHHO 3,4-F 2 4-OCF 2 CHF 2 4-OCF 3 HH HHO 3,5-F 2 4-OCF 2 CHF 2 4-Cl HHHHO 3-Cl-4-F 4-OCF 2 CHF 2 4-CF 3 ───────────────── ────────────────────
【００９３】[0093]
【表５９】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 2,4-F2 4-Cl H H H H O 3-Cl 2,4-F2 4-CF3 H H H H O 4-Cl 2,4-F2 4-OCF3 H H H H O 3-Br 2,4-F2 4-Cl H H H H O 3-CH3 2,4-F2 4-CF3 H H H H O 4-CF3 2,4-F2 4-OCF3 H H H H O 3-OCH3 2,4-F2 4-Cl H H H H O 3-OCHF2 2,4-F2 4-CF3 H H H H O 4-OCHF2 2,4-F2 4-OCF3 H H H H O 3-OCF2Br 2,4-F2 4-Cl H H H H O 3-OCF3 2,4-F2 4-CF3 H H H H O 3-OCH2CF3 2,4-F2 4-OCF3 H H H H O 3-OCF2CHF2 2,4-F2 4-Cl H H H H O 3-SCHF2 2,4-F2 4-CF3 H H H H O 3-SCF3 2,4-F2 4-OCF3 H H H H O 3-NO2 2,4-F2 4-Cl H H H H O 3-CN 2,4-F2 4-CF3 H H H H O 3-OSO2CH3 2,4-F2 4-OCF3 H H H H O 3-OSO2CF3 2,4-F2 4-Cl H H H H O 4-OSO2CF3 2,4-F2 4-CF3 H H H H O 3,4-F2 2,4-F2 4-OCF3 H H H H O 3,5-F2 2,4-F2 4-Cl H H H H O 3-Cl-4-F 2,4-F2 4-CF3 ───────────────────────────────────[Table 59] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 2,4-F 2 4- Cl HHHHO 3-Cl 2,4-F 2 4-CF 3 HHHHO 4-Cl 2,4-F 2 4-OCF 3 HHHHO 3-Br 2,4-F 2 4-Cl HHHHO 3-CH 3 2,4 -F 2 4-CF 3 HHHHO 4-CF 3 2,4-F 2 4-OCF 3 HHHHO 3-OCH 3 2,4-F 2 4-Cl HHHHO 3-OCHF 2 2,4-F 2 4-CF 3 HHHHO 4-OCHF 2 2,4-F 2 4-OCF 3 HHHHO 3-OCF 2 Br 2,4-F 2 4-Cl HHHHO 3-OCF 3 2,4-F 2 4-CF 3 HHHHO 3-OCH 2 CF 3 2,4-F 2 4-OCF 3 HHHHO 3-OCF 2 CHF 2 2,4-F 2 4-Cl HHHHO 3-SCHF 2 2,4-F 2 4-CF 3 HHHHO 3-SCF 3 2 , 4-F 2 4-OCF 3 HHHHO 3-NO 2 2,4-F 2 4-Cl HHHHO 3-CN 2,4-F 2 4-CF 3 HHHHO 3-OSO 2 CH 3 2,4-F 2 4-OCF 3 HHHHO 3-OSO 2 CF 3 2,4-F 2 4-Cl HHHHO 4-OSO 2 CF 3 2,4-F 2 4-CF 3 HHHHO 3,4-F 2 2,4-F 2 4-OCF 3 HHHHO 3,5-F 2 2,4-F 2 4-Cl HHHHO 3-Cl-4-F 2,4-F 2 4-CF 3 ──────────── ─────────── ───────────
【００９４】[0094]
【表６０】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H O 4-F 3,4-F2 4-Cl H H H H O 3-Cl 3,4-F2 4-CF3 H H H H O 4-Cl 3,4-F2 4-OCF3 H H H H O 3-Br 3,4-F2 4-Cl H H H H O 3-CH3 3,4-F2 4-CF3 H H H H O 4-CF3 3,4-F2 4-OCF3 H H H H O 3-OCH3 3,4-F2 4-Cl H H H H O 3-OCHF2 3,4-F2 4-CF3 H H H H O 4-OCHF2 3,4-F2 4-OCF3 H H H H O 3-OCF2Br 3,4-F2 4-Cl H H H H O 3-OCF3 3,4-F2 4-CF3 H H H H O 3-OCH2CF3 3,4-F2 4-OCF3 H H H H O 3-OCF2CHF2 3,4-F2 4-Cl H H H H O 3-SCHF2 3,4-F2 4-CF3 H H H H O 3-SCF3 3,4-F2 4-OCF3 H H H H O 3-NO2 3,4-F2 4-Cl H H H H O 3-CN 3,4-F2 4-CF3 H H H H O 3-OSO2CH3 3,4-F2 4-OCF3 H H H H O 3-OSO2CF3 3,4-F2 4-Cl H H H H O 4-OSO2CF3 3,4-F2 4-CF3 H H H H O 3,4-F2 3,4-F2 4-OCF3 H H H H O 3,5-F2 3,4-F2 4-Cl H H H H O 3-Cl-4-F 3,4-F2 4-CF3 ───────────────────────────────────[Table 60] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHO 4-F 3,4-F 2 4- Cl HHHHO 3-Cl 3,4-F 2 4-CF 3 HHHHO 4-Cl 3,4-F 2 4-OCF 3 HHHHO 3-Br 3,4-F 2 4-Cl HHHHO 3-CH 3 3,4 -F 2 4-CF 3 HHHHO 4-CF 3 3,4-F 2 4-OCF 3 HHHHO 3-OCH 3 3,4-F 2 4-Cl HHHHO 3-OCHF 2 3,4-F 2 4-CF 3 HHHHO 4-OCHF 2 3,4-F 2 4-OCF 3 HHHHO 3-OCF 2 Br 3,4-F 2 4-Cl HHHHO 3-OCF 3 3,4-F 2 4-CF 3 HHHHO 3-OCH 2 CF 3 3,4-F 2 4-OCF 3 HHHHO 3-OCF 2 CHF 2 3,4-F 2 4-Cl HHHHO 3-SCHF 2 3,4-F 2 4-CF 3 HHHHO 3-SCF 3 3 , 4-F 2 4-OCF 3 HHHHO 3-NO 2 3,4-F 2 4-Cl HHHHO 3-CN 3,4-F 2 4-CF 3 HHHHO 3-OSO 2 CH 3 3,4-F 2 4-OCF 3 HHHHO 3-OSO 2 CF 3 3,4-F 2 4-Cl HHHHO 4-OSO 2 CF 3 3,4-F 2 4-CF 3 HHHHO 3,4-F 2 3,4-F 2 4-OCF 3 HHHHO 3,5-F 2 3,4-F 2 4-Cl HHHHO 3-Cl-4-F 3,4-F 2 4-CF 3 ──────────── ─────────── ───────────
【００９５】[0095]
【表６１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H H S 3-F 4-F 4-Cl H H H H S 3-F 4-F 4-Br H H H H S 3-F 4-F 4-CF3 H H H H S 3-F 4-F 4-OCF3 H H H H S 3-F 4-F 4-OCHF2 H H H H S 3-F 4-F 4-OCF2Br H H H H S 3-F 4-F 4-OCF2CHF2 H H H H S 3-F 4-F 4-OSO2CF3 H H H H S H 4-F 4-OCF3 H H H H S 4-F 4-F 4-Cl H H H H S 3-Cl 4-F 4-CF3 H H H H S 3-Br 4-F 4-OCF3 H H H H S 3-CF3 4-F 4-Cl H H H H S 3-OCF3 4-F 4-CF3 H H H H S 3-OCHF2 4-F 4-OCF3 H H H H S 4-OCHF2 4-F 4-Cl H H H H S 3-F 4-Cl 4-CF3 H H H H S 3-F 4-Br 4-OCF3 H H H H S 3-F 4-CF3 4-Cl H H H H S 3-F 4-OSO2CF3 4-CF3 H H H H S 3-F 4-CN 4-OCF3 H H H H S 3-F 3,4-F2 4-Cl H H H H S 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 61] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHHHS 3-F 4-F 4-Cl HHHHS 3 -F 4-F 4-Br HHHHS 3-F 4-F 4-CF 3 HHHHS 3-F 4-F 4-OCF 3 HHHHS 3-F 4-F 4-OCHF 2 HHHHS 3-F 4-F 4- OCF 2 Br HHHHS 3-F 4-F 4-OCF 2 CHF 2 HHHHS 3-F 4-F 4-OSO 2 CF 3 HHHHSH 4-F 4-OCF 3 HHHHS 4-F 4-F 4-Cl HHHHS 3- Cl 4-F 4-CF 3 HHHHS 3-Br 4-F 4-OCF 3 HHHHS 3-CF 3 4-F 4-Cl HHHHS 3-OCF 3 4-F 4-CF 3 HHHHS 3-OCHF 2 4-F 4-OCF 3 HHHHS 4-OCHF 2 4-F 4-Cl HHHHS 3-F 4-Cl 4-CF 3 HHHHS 3-F 4-Br 4-OCF 3 HHHHS 3-F 4-CF 3 4-Cl HHHHS 3 -F 4-OSO 2 CF 3 4-CF 3 HHHHS 3-F 4-CN 4-OCF 3 HHHHS 3-F 3,4-F 2 4-Cl HHHHS 3-CF 3 4-CN 4-CF 3 ── ──────────────────────────────────
【００９６】[0096]
【表６２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H CH3 O 3-F 4-F 4-Cl H H H CH3 O 3-F 4-F 4-Br H H H CH3 O 3-F 4-F 4-CF3 H H H CH3 O 3-F 4-F 4-OCF3 H H H CH3 O 3-F 4-F 4-OCHF2 H H H CH3 O 3-F 4-F 4-OCF2Br H H H CH3 O 3-F 4-F 4-OCF2CHF2 H H H CH3 O 3-F 4-F 4-OSO2CF3 H H H CH3 O H 4-F 4-OCF3 H H H CH3 S 4-F 4-F 4-Cl H H H CH3 O 3-Cl 4-F 4-CF3 H H H CH3 O 3-Br 4-F 4-OCF3 H H H CH3 O 3-CF3 4-F 4-Cl H H H CH3 O 3-OCF3 4-F 4-CF3 H H H CH3 O 3-OCHF2 4-F 4-OCF3 H H H CH3 O 4-OCHF2 4-F 4-Cl H H H CH3 S 3-F 4-Cl 4-CF3 H H H CH3 O 3-F 4-Br 4-OCF3 H H H CH3 O 3-F 4-CF3 4-Cl H H H CH3 O 3-F 4-OSO2CF3 4-CF3 H H H CH3 O 3-F 4-CN 4-OCF3 H H H CH3 O 3-F 3,4-F2 4-Cl H H H CH3 O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 62] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHH CH 3 O 3-F 4-F 4- Cl HHH CH 3 O 3-F 4-F 4-Br HHH CH 3 O 3-F 4-F 4-CF 3 HHH CH 3 O 3-F 4-F 4-OCF 3 HHH CH 3 O 3-F 4 -F 4-OCHF 2 HHH CH 3 O 3-F 4-F 4-OCF 2 Br HHH CH 3 O 3-F 4-F 4-OCF 2 CHF 2 HHH CH 3 O 3-F 4-F 4-OSO 2 CF 3 HHH CH 3 OH 4-F 4-OCF 3 HHH CH 3 S 4-F 4-F 4-Cl HHH CH 3 O 3-Cl 4-F 4-CF 3 HHH CH 3 O 3-Br 4- F 4-OCF 3 HHH CH 3 O 3-CF 3 4-F 4-Cl HHH CH 3 O 3-OCF 3 4-F 4-CF 3 HHH CH 3 O 3-OCHF 2 4-F 4-OCF 3 HHH CH 3 O 4-OCHF 2 4-F 4-Cl HHH CH 3 S 3-F 4-Cl 4-CF 3 HHH CH 3 O 3-F 4-Br 4-OCF 3 HHH CH 3 O 3-F 4- CF 3 4-Cl HHH CH 3 O 3-F 4-OSO 2 CF 3 4-CF 3 HHH CH 3 O 3-F 4-CN 4-OCF 3 HHH CH 3 O 3-F 3,4-F 2 4 -Cl HHH CH 3 O 3-CF 3 4-CN 4-CF 3 ─────────────────────────────── ───
【００９７】[0097]
【表６３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H CH3 H O 3-F 4-F 4-Cl H H CH3 H O 3-F 4-F 4-Br H H CH3 H O 3-F 4-F 4-CF3 H H CH3 H O 3-F 4-F 4-OCF3 H H CH3 H O 3-F 4-F 4-OCHF2 H H CH3 H O 3-F 4-F 4-OCF2Br H H CH3 H O 3-F 4-F 4-OCF2CHF2 H H CH3 H O 3-F 4-F 4-OSO2CF3 H H CH3 H O H 4-F 4-OCF3 H H CH3 H S 4-F 4-F 4-Cl H H CH3 H O 3-Cl 4-F 4-CF3 H H CH3 H O 3-Br 4-F 4-OCF3 H H CH3 H O 3-CF3 4-F 4-Cl H H CH3 H O 3-OCF3 4-F 4-CF3 H H CH3 H O 3-OCHF2 4-F 4-OCF3 H H CH3 H O 4-OCHF2 4-F 4-Cl H H CH3 H S 3-F 4-Cl 4-CF3 H H CH3 H O 3-F 4-Br 4-OCF3 H H CH3 H O 3-F 4-CF3 4-Cl H H CH3 H O 3-F 4-OSO2CF3 4-CF3 H H CH3 H O 3-F 4-CN 4-OCF3 H H CH3 H O 3-F 3,4-F2 4-Cl H H CH3 H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 63] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HH CH 3 HO 3-F 4-F 4- Cl HH CH 3 HO 3-F 4-F 4-Br HH CH 3 HO 3-F 4-F 4-CF 3 HH CH 3 HO 3-F 4-F 4-OCF 3 HH CH 3 HO 3-F 4 -F 4-OCHF 2 HH CH 3 HO 3-F 4-F 4-OCF 2 Br HH CH 3 HO 3-F 4-F 4-OCF 2 CHF 2 HH CH 3 HO 3-F 4-F 4-OSO 2 CF 3 HH CH 3 HOH 4-F 4-OCF 3 HH CH 3 HS 4-F 4-F 4-Cl HH CH 3 HO 3-Cl 4-F 4-CF 3 HH CH 3 HO 3-Br 4- F 4-OCF 3 HH CH 3 HO 3-CF 3 4-F 4-Cl HH CH 3 HO 3-OCF 3 4-F 4-CF 3 HH CH 3 HO 3-OCHF 2 4-F 4-OCF 3 HH CH 3 HO 4-OCHF 2 4-F 4-Cl HH CH 3 HS 3-F 4-Cl 4-CF 3 HH CH 3 HO 3-F 4-Br 4-OCF 3 HH CH 3 HO 3-F 4- CF 3 4-Cl HH CH 3 HO 3-F 4-OSO 2 CF 3 4-CF 3 HH CH 3 HO 3-F 4-CN 4-OCF 3 HH CH 3 HO 3-F 3,4-F 2 4 -Cl HH CH 3 HO 3-CF 3 4-CN 4-CF 3 ─────────────────────────────── ───
【００９８】[0098]
【表６４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H CH3 H H O 3-F 4-F 4-Cl H CH3 H H O 3-F 4-F 4-Br H CH3 H H O 3-F 4-F 4-CF3 H CH3 H H O 3-F 4-F 4-OCF3 H CH3 H H O 3-F 4-F 4-OCHF2 H CH3 H H O 3-F 4-F 4-OCF2Br H CH3 H H O 3-F 4-F 4-OCF2CHF2 H CH3 H H O 3-F 4-F 4-OSO2CF3 H CH3 H H O H 4-F 4-OCF3 H CH3 H H S 4-F 4-F 4-Cl H CH3 H H O 3-Cl 4-F 4-CF3 H CH3 H H O 3-Br 4-F 4-OCF3 H CH3 H H O 3-CF3 4-F 4-Cl H CH3 H H O 3-OCF3 4-F 4-CF3 H CH3 H H O 3-OCHF2 4-F 4-OCF3 H CH3 H H O 4-OCHF2 4-F 4-Cl H CH3 H H S 3-F 4-Cl 4-CF3 H CH3 H H O 3-F 4-Br 4-OCF3 H CH3 H H O 3-F 4-CF3 4-Cl H CH3 H H O 3-F 4-OSO2CF3 4-CF3 H CH3 H H O 3-F 4-CN 4-OCF3 H CH3 H H O 3-F 3,4-F2 4-Cl H CH3 H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 64] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── H CH 3 HHO 3-F 4-F 4- Cl H CH 3 HHO 3-F 4-F 4-Br H CH 3 HHO 3-F 4-F 4-CF 3 H CH 3 HHO 3-F 4-F 4-OCF 3 H CH 3 HHO 3-F 4 -F 4-OCHF 2 H CH 3 HHO 3-F 4-F 4-OCF 2 Br H CH 3 HHO 3-F 4-F 4-OCF 2 CHF 2 H CH 3 HHO 3-F 4-F 4-OSO 2 CF 3 H CH 3 HHOH 4-F 4-OCF 3 H CH 3 HHS 4-F 4-F 4-Cl H CH 3 HHO 3-Cl 4-F 4-CF 3 H CH 3 HHO 3-Br 4- F 4-OCF 3 H CH 3 HHO 3-CF 3 4-F 4-Cl H CH 3 HHO 3-OCF 3 4-F 4-CF 3 H CH 3 HHO 3-OCHF 2 4-F 4-OCF 3 H CH 3 HHO 4-OCHF 2 4-F 4-Cl H CH 3 HHS 3-F 4-Cl 4-CF 3 H CH 3 HHO 3-F 4-Br 4-OCF 3 H CH 3 HHO 3-F 4- CF 3 4-Cl H CH 3 HHO 3-F 4-OSO 2 CF 3 4-CF 3 H CH 3 HHO 3-F 4-CN 4-OCF 3 H CH 3 HHO 3-F 3,4-F 2 4 -Cl H CH 3 HHO 3-CF 3 4-CN 4-CF 3 ─────────────────────────────── ───
【００９９】[0099]
【表６５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── CH3 H H H O 3-F 4-F 4-Cl CH3 H H H O 3-F 4-F 4-Br CH3 H H H O 3-F 4-F 4-CF3 CH3 H H H O 3-F 4-F 4-OCF3 CH3 H H H O 3-F 4-F 4-OCHF2 CH3 H H H O 3-F 4-F 4-OCF2Br CH3 H H H O 3-F 4-F 4-OCF2CHF CH3 H H H O 3-F 4-F 4-OSO2CF3 CH3 H H H O H 4-F 4-OCF3 CH3 H H H S 4-F 4-F 4-Cl CH3 H H H O 3-Cl 4-F 4-CF3 CH3 H H H O 3-Br 4-F 4-OCF3 CH3 H H H O 3-CF3 4-F 4-Cl CH3 H H H O 3-OCF3 4-F 4-CF3 CH3 H H H O 3-OCHF2 4-F 4-OCF3 CH3 H H H O 4-OCHF2 4-F 4-Cl CH3 H H H S 3-F 4-Cl 4-CF3 CH3 H H H O 3-F 4-Br 4-OCF3 CH3 H H H O 3-F 4-CF3 4-Cl CH3 H H H O 3-F 4-OSO2CF3 4-CF3 CH3 H H H O 3-F 4-CN 4-OCF3 CH3 H H H O 3-F 3,4-F2 4-Cl CH3 H H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 65] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── CH 3 HHHO 3-F 4-F 4-Cl CH 3 HHHO 3-F 4-F 4-Br CH 3 HHHO 3-F 4-F 4-CF 3 CH 3 HHHO 3-F 4-F 4-OCF 3 CH 3 HHHO 3-F 4-F 4-OCHF 2 CH 3 HHHO 3-F 4-F 4-OCF 2 Br CH 3 HHHO 3-F 4-F 4-OCF 2 CHF CH 3 HHHO 3-F 4-F 4-OSO 2 CF 3 CH 3 HHHOH 4-F 4-OCF 3 CH 3 HHHS 4-F 4-F 4-Cl CH 3 HHHO 3-Cl 4-F 4-CF 3 CH 3 HHHO 3-Br 4-F 4-OCF 3 CH 3 HHHO 3-CF 3 4 -F 4-Cl CH 3 HHHO 3-OCF 3 4-F 4-CF 3 CH 3 HHHO 3-OCHF 2 4-F 4-OCF 3 CH 3 HHHO 4-OCHF 2 4-F 4-Cl CH 3 HHHS 3 -F 4-Cl 4-CF 3 CH 3 HHHO 3-F 4-Br 4-OCF 3 CH 3 HHHO 3-F 4-CF 3 4-Cl CH 3 HHHO 3-F 4-OSO 2 CF 3 4-CF 3 CH 3 HHHO 3-F 4-CN 4-OCF 3 CH 3 HHHO 3-F 3,4-F 2 4-Cl CH 3 HHHO 3-CF 3 4-CN 4-CF 3 ──────── ────────────────────────────
【０１００】[0100]
【表６６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H H CH2CH3 O 3-F 4-F 4-Cl H H H CH2CH2CH3 O 3-F 4-F 4-Br H H H CH2CH2CH2CH3 O 3-F 4-F 4-CF3 H H H CH(CH3)2 O 3-F 4-F 4-OCF3 H H H C(CH3)3 O 3-F 4-F 4-OCHF2 H H H CH2CH=CH2 O 3-F 4-F 4-OCF2Br H H H CH2Ｃ≡CH O 3-F 4-F 4-OCF2CHF2 H H H CH2OCH3 O 3-F 4-F 4-OSO2CF3 H H H CH2OCH2CH3 O H 4-F 4-OCF3 H H H CH2CH2OCH3 O 4-F 4-F 4-Cl H H H CHF2 O 3-Cl 4-F 4-CF3 H H H CBrF2 O 3-Br 4-F 4-OCF3 H H H CF3 O 3-CF3 4-F 4-Cl H H H COCH3 O 3-OCF3 4-F 4-CF3 H H H COCF3 O 3-OCHF2 4-F 4-OCF3 H H H CO2CH3 O 4-OCHF2 4-F 4-Cl H H H CH2C6H5 O 3-F 4-Cl 4-CF3 H H H SC6H5 O 3-F 4-Br 4-OCF3 H H H SCCl3 O 3-F 4-CF3 4-Cl H H H SCO2CH2CH3 O 3-F 4-OSO2CF3 4-CF3 H H H S(C6H4-2-NO2) O 3-F 4-CN 4-OCF3 H H H SN(CH2CH2CH2CH3)2 O 3-F 3,4-F2 4-Cl H H H SN(CH3)CO2CH2CH3 O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 66] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HHH CH 2 CH 3 O 3-F 4-F 4-Cl HHH CH 2 CH 2 CH 3 O 3-F 4-F 4-Br HHH CH 2 CH 2 CH 2 CH 3 O 3-F 4-F 4-CF 3 HHH CH (CH 3 ) 2 O 3- F 4-F 4-OCF 3 HHHC (CH 3 ) 3 O 3-F 4-F 4-OCHF 2 HHH CH 2 CH = CH 2 O 3-F 4-F 4-OCF 2 Br HHH CH 2 C≡CH O 3-F 4-F 4-OCF 2 CHF 2 HHH CH 2 OCH 3 O 3-F 4-F 4-OSO 2 CF 3 HHH CH 2 OCH 2 CH 3 OH 4-F 4-OCF 3 HHH CH 2 CH 2 OCH 3 O 4-F 4-F 4-Cl HHH CHF 2 O 3-Cl 4-F 4-CF 3 HHH CBrF 2 O 3-Br 4-F 4-OCF 3 HHH CF 3 O 3-CF 3 4 -F 4-Cl HHH COCH 3 O 3-OCF 3 4-F 4-CF 3 HHH COCF 3 O 3-OCHF 2 4-F 4-OCF 3 HHH CO 2 CH 3 O 4-OCHF 2 4-F 4- Cl HHH CH 2 C 6 H 5 O 3-F 4-Cl 4-CF 3 HHH SC 6 H 5 O 3-F 4-Br 4-OCF 3 HHH SCCl 3 O 3-F 4-CF 3 4-Cl HHH SCO 2 CH 2 CH 3 O 3-F 4-OSO 2 CF 3 4-CF 3 HHHS (C 6 H 4 -2-NO 2 ) O 3-F 4-CN 4-OCF 3 HHH SN (CH 2 CH 2 CH 2 CH 3 ) 2 O 3-F 3,4-F 2 4-Cl HHH SN (CH 3 ) CO 2 CH 2 CH 3 O 3-CF 3 4-CN 4-CF 3 ─────── ─────────────────────────────
【０１０１】[0101]
【表６７】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H CH2CH3 H O 3-F 4-F 4-Cl H H CH2CH2CH3 H O 3-F 4-F 4-Br H H CH2CH2CH2CH3 H O 3-F 4-F 4-CF3 H H CH(CH3)2 H O 3-F 4-F 4-OCF3 H H C(CH3)3 H O 3-F 4-F 4-OCHF2 H H CH2CH=CH2 H O 3-F 4-F 4-OCF2Br H H CH2Ｃ≡CH H O 3-F 4-F 4-OCF2CHF2 H H CH2OCH3 H O 3-F 4-F 4-OSO2CF3 H H CH2OCH2CH3 H O H 4-F 4-OCF3 H H CH2CH2OCH3 H O 4-F 4-F 4-Cl H H CHF2 H O 3-Cl 4-F 4-CF3 H H CBrF2 H O 3-Br 4-F 4-OCF3 H H CF3 H O 3-CF3 4-F 4-Cl H H COCH3 H O 3-OCF3 4-F 4-CF3 H H COCF3 H O 3-OCHF2 4-F 4-OCF3 H H CO2CH3 H O 4-OCHF2 4-F 4-Cl H H CH2C6H5 H O 3-F 4-Cl 4-CF3 H H SC6H5 H O 3-F 4-Br 4-OCF3 H H SCCl3 H O 3-F 4-CF3 4-Cl H H SCO2CH2CH3 H O 3-F 4-OSO2CF3 4-CF3 H H S(C6H4-2-NO2) H O 3-F 4-CN 4-OCF3 H H SN(CH2CH2CH2CH3)2 H O 3-F 3,4-F2 4-Cl H H SN(CH3)CO2CH2CH3 H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 67] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HH CH 2 CH 3 HO 3-F 4-F 4-Cl HH CH 2 CH 2 CH 3 HO 3-F 4-F 4-Br HH CH 2 CH 2 CH 2 CH 3 HO 3-F 4-F 4-CF 3 HH CH (CH 3 ) 2 HO 3- F 4-F 4-OCF 3 HHC (CH 3 ) 3 HO 3-F 4-F 4-OCHF 2 HH CH 2 CH = CH 2 HO 3-F 4-F 4-OCF 2 Br HH CH 2 C≡CH HO 3-F 4-F 4-OCF 2 CHF 2 HH CH 2 OCH 3 HO 3-F 4-F 4-OSO 2 CF 3 HH CH 2 OCH 2 CH 3 HOH 4-F 4-OCF 3 HH CH 2 CH 2 OCH 3 HO 4-F 4-F 4-Cl HH CHF 2 HO 3-Cl 4-F 4-CF 3 HH CBrF 2 HO 3-Br 4-F 4-OCF 3 HH CF 3 HO 3-CF 3 4 -F 4-Cl HH COCH 3 HO 3-OCF 3 4-F 4-CF 3 HH COCF 3 HO 3-OCHF 2 4-F 4-OCF 3 HH CO 2 CH 3 HO 4-OCHF 2 4-F 4- Cl HH CH 2 C 6 H 5 HO 3-F 4-Cl 4-CF 3 HH SC 6 H 5 HO 3-F 4-Br 4-OCF 3 HH SCCl 3 HO 3-F 4-CF 3 4-Cl HH SCO 2 CH 2 CH 3 HO 3-F 4-OSO 2 CF 3 4-CF 3 HHS (C 6 H 4 -2-NO 2 ) HO 3-F 4-CN 4-OCF 3 HH SN (CH 2 CH 2 CH 2 CH 3 ) 2 HO 3-F 3,4-F 2 4-Cl HH SN (CH 3 ) CO 2 CH 2 CH 3 HO 3-CF 3 4-CN 4-CF 3 ──────── ────────────────────────────
【０１０２】[0102]
【表６８】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H CH2CH3 H H O 3-F 4-F 4-Cl H CH2CH2CH3 H H O 3-F 4-F 4-Br H CH2CH2CH2CH3 H H O 3-F 4-F 4-CF3 H CH(CH3)2 H H O 3-F 4-F 4-OCF3 H C(CH3)3 H H O 3-F 4-F 4-OCHF2 H CH2CH=CH2 H H O 3-F 4-F 4-OCF2Br H CH2Ｃ≡CH H H O 3-F 4-F 4-OCF2CHF2 H CH2OCH3 H H O 3-F 4-F 4-OSO2CF3 H CH2OCH2CH3 H H O H 4-F 4-OCF3 H CH2CH2OCH3 H H O 4-F 4-F 4-Cl H CHF2 H H O 3-Cl 4-F 4-CF3 H CBrF2 H H O 3-Br 4-F 4-OCF3 H CF3 H H O 3-CF3 4-F 4-Cl H CH2CH3 H H O 3-OCF3 4-F 4-CF3 H COCF3 H H O 3-OCHF2 4-F 4-OCF3 H CO2CH2CH3 H H O 4-OCHF2 4-F 4-Cl H CH2C6H5 H H O 3-F 4-Cl 4-CF3 H SC6H5 H H O 3-F 4-Br 4-OCF3 H SCCl3 H H O 3-F 4-CF3 4-Cl H SCO2CH2CH3 H H O 3-F 4-OSO2CF3 4-CF3 H S(C6H4-2-NO2) H H O 3-F 4-CN 4-OCF3 H SN(CH2CH2CH2CH3)2 H H O 3-F 3,4-F2 4-Cl H SN(CH3)CO2CH2CH3 H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 68] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── H CH 2 CH 3 HHO 3-F 4-F 4-Cl H CH 2 CH 2 CH 3 HHO 3-F 4-F 4-Br H CH 2 CH 2 CH 2 CH 3 HHO 3-F 4-F 4-CF 3 H CH (CH 3 ) 2 HHO 3- F 4-F 4-OCF 3 HC (CH 3 ) 3 HHO 3-F 4-F 4-OCHF 2 H CH 2 CH = CH 2 HHO 3-F 4-F 4-OCF 2 Br H CH 2 C≡CH HHO 3-F 4-F 4-OCF 2 CHF 2 H CH 2 OCH 3 HHO 3-F 4-F 4-OSO 2 CF 3 H CH 2 OCH 2 CH 3 HHOH 4-F 4-OCF 3 H CH 2 CH 2 OCH 3 HHO 4-F 4-F 4-Cl H CHF 2 HHO 3-Cl 4-F 4-CF 3 H CBrF 2 HHO 3-Br 4-F 4-OCF 3 H CF 3 HHO 3-CF 3 4 -F 4-Cl H CH 2 CH 3 HHO 3-OCF 3 4-F 4-CF 3 H COCF 3 HHO 3-OCHF 2 4-F 4-OCF 3 H CO 2 CH 2 CH 3 HHO 4-OCHF 2 4 -F 4-Cl H CH 2 C 6 H 5 HHO 3-F 4-Cl 4-CF 3 H SC 6 H 5 HHO 3-F 4-Br 4-OCF 3 H SCCl 3 HHO 3-F 4-CF 3 4-Cl H SCO 2 CH 2 CH 3 HHO 3-F 4-OSO 2 CF 3 4-CF 3 HS (C 6 H 4 -2-NO 2 ) HHO 3-F 4-CN 4-OCF 3 H SN ( CH 2 CH 2 CH 2 CH 3 ) 2 HHO 3-F 3,4-F 2 4-Cl H SN (CH 3 ) CO 2 CH 2 CH 3 HHO 3-CF 3 4-CN 4-CF 3 ──── ───────────────────────────────
【０１０３】[0103]
【表６９】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H COCH3 H H O 3-F 4-F 4-Cl H COCH3 H H O 3-F 4-F 4-Br H COCH3 H H O 3-F 4-F 4-CF3 H COCH3 H H O 3-F 4-F 4-OCF3 H COCH3 H H O 3-F 4-F 4-OCHF2 H COCH3 H H O 3-F 4-F 4-OCF2Br H COCH3 H H O 3-F 4-F 4-OCF2CHF2 H COCH3 H H O 3-F 4-F 4-OSO2CF3 H COCH3 H H O H 4-F 4-OCF3 H COCH3 H H O 4-F 4-F 4-Cl H COCH3 H H O 3-Cl 4-F 4-CF3 H COCH3 H H O 3-Br 4-F 4-OCF3 OSO2CF3 H H H O 3-CF3 4-F 4-Cl CO2CH2CH3 H H H O 3-OCF3 4-F 4-CF3 CO2CH3 H H H O 3-OCHF2 4-F 4-OCF3 NH2 H H H O 4-OCHF2 4-F 4-Cl N(CH3)2 H H H O 3-F 4-Cl 4-CF3 C6H5 H H H O 3-F 4-Br 4-OCF3 C6H4-4-F H H H O 3-F 4-CF3 4-Cl C6H4-4-Cl H H H O 3-F 4-OSO2CF3 4-CF3 C6H4-4-CN H H H O 3-F 4-CN 4-OCF3 C6H4-4-CF3 H H H O 3-F 3,4-F2 4-Cl CH2C6H5 H H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 69] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── H COCH 3 HHO 3-F 4-F 4- Cl H COCH 3 HHO 3-F 4-F 4-Br H COCH 3 HHO 3-F 4-F 4-CF 3 H COCH 3 HHO 3-F 4-F 4-OCF 3 H COCH 3 HHO 3-F 4 -F 4-OCHF 2 H COCH 3 HHO 3-F 4-F 4-OCF 2 Br H COCH 3 HHO 3-F 4-F 4-OCF 2 CHF 2 H COCH 3 HHO 3-F 4-F 4-OSO 2 CF 3 H COCH 3 HHOH 4-F 4-OCF 3 H COCH 3 HHO 4-F 4-F 4-Cl H COCH 3 HHO 3-Cl 4-F 4-CF 3 H COCH 3 HHO 3-Br 4- F 4-OCF 3 OSO 2 CF 3 HHHO 3-CF 3 4-F 4-Cl CO 2 CH 2 CH 3 HHHO 3-OCF 3 4-F 4-CF 3 CO 2 CH 3 HHHO 3-OCHF 2 4-F 4-OCF 3 NH 2 HHHO 4-OCHF 2 4-F 4-Cl N (CH 3 ) 2 HHHO 3-F 4-Cl 4-CF 3 C 6 H 5 HHHO 3-F 4-Br 4-OCF 3 C 6 H 4 -4-FHHHO 3-F 4-CF 3 4-Cl C 6 H 4 -4-Cl HHHO 3-F 4-OSO 2 CF 3 4-CF 3 C 6 H 4 -4-CN HHHO 3- F 4-CN 4-OCF 3 C 6 H 4 -4-CF 3 HHHO 3-F 3,4-F 2 4-Cl CH 2 C 6 H 5 HHHO 3-CF 3 4-CN 4-CF 3 ── ────────────────────────────────
【０１０４】[0104]
【表７０】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── CH2CH3 H H H O 3-F 4-F 4-Cl CH2CH2CH3 H H H O 3-F 4-F 4-Br CH2CH2CH2CH3 H H H O 3-F 4-F 4-CF3 CH(CH3)2 H H H O 3-F 4-F 4-OCF3 C(CH3)3 H H H O 3-F 4-F 4-OCHF2 Q1 H H H O 3-F 4-F 4-OCF2Br Q4 H H H O 3-F 4-F 4-OCF2CHF2 F H H H O 3-F 4-F 4-OSO2CF3 Cl H H H O H 4-F 4-OCF3 Br H H H O 4-F 4-F 4-Cl I H H H O 3-Cl 4-F 4-CF3 OH H H H O 3-Br 4-F 4-OCF3 CN H H H O 3-CF3 4-F 4-Cl NO2 H H H O 3-OCF3 4-F 4-CF3 CH2F H H H O 3-OCHF2 4-F 4-OCF3 CF3 H H H O 4-OCHF2 4-F 4-Cl OCH3 H H H O 3-F 4-Cl 4-CF3 OCH2CH3 H H H O 3-F 4-Br 4-OCF3 OCF3 H H H O 3-F 4-CF3 4-Cl SCH3 H H H O 3-F 4-OSO2CF3 4-CF3 SCF3 H H H O 3-F 4-CN 4-OCF3 SO2CH3 H H H O 3-F 3,4-F2 4-Cl SO2CF3 H H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 70] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── CH 2 CH 3 HHHO 3-F 4-F 4 -Cl CH 2 CH 2 CH 3 HHHO 3-F 4-F 4-Br CH 2 CH 2 CH 2 CH 3 HHHO 3-F 4-F 4-CF 3 CH (CH 3 ) 2 HHHO 3-F 4-F 4-OCF 3 C (CH 3 ) 3 HHHO 3-F 4-F 4-OCHF 2 Q1 HHHO 3-F 4-F 4-OCF 2 Br Q4 HHHO 3-F 4-F 4-OCF 2 CHF 2 FHHHO 3 -F 4-F 4-OSO 2 CF 3 Cl HHHOH 4-F 4-OCF 3 Br HHHO 4-F 4-F 4-Cl IHHHO 3-Cl 4-F 4-CF 3 OH HHHO 3-Br 4-F 4-OCF 3 CN HHHO 3-CF 3 4-F 4-Cl NO 2 HHHO 3-OCF 3 4-F 4-CF 3 CH 2 FHHHO 3-OCHF 2 4-F 4-OCF 3 CF 3 HHHO 4-OCHF 2 4-F 4-Cl OCH 3 HHHO 3-F 4-Cl 4-CF 3 OCH 2 CH 3 HHHO 3-F 4-Br 4-OCF 3 OCF 3 HHHO 3-F 4-CF 3 4-Cl SCH 3 HHHO 3-F 4-OSO 2 CF 3 4-CF 3 SCF 3 HHHO 3-F 4-CN 4-OCF 3 SO 2 CH 3 HHHO 3-F 3,4-F 2 4-Cl SO 2 CF 3 HHHO 3 -CF 3 4-CN 4-CF 3 ──────────────────────── ──────────
【０１０５】[0105]
【表７１】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H CH3 CH3 O 3-F 4-F 4-Cl H H CH3 CH3 O 3-F 4-F 4-Br H H CH3 CH3 O 3-F 4-F 4-CF3 H H CH3 CH3 O 3-F 4-F 4-OCF3 H H CH3 CH3 O 3-F 4-F 4-OCHF2 H H CH3 CH3 O 3-F 4-F 4-OCF2Br H H CH3 CH3 O 3-F 4-F 4-OCF2CHF2 H H CH3 CH3 O 3-F 4-F 4-OSO2CF3 H H CH3 CH3 O H 4-F 4-OCF3 H H CH3 CH3 O 4-F 4-F 4-Cl H H CH3 CH3 O 3-Cl 4-F 4-CF3 H H CH3 CH3 O 3-Br 4-F 4-OCF3 H H CH3 CH3 O 3-CF3 4-F 4-Cl CH3 CH3 H H O 3-OCF3 4-F 4-CF3 CH3 CH3 H H O 3-OCHF2 4-F 4-OCF3 CH3 CH3 H H O 4-OCHF2 4-F 4-Cl CH3 CH3 H H O 3-F 4-Cl 4-CF3 CH3 CH3 H H O 3-F 4-Br 4-OCF3 CH3 CH3 H H O 3-F 4-CF3 4-Cl CH3 CH3 H H O 3-F 4-OSO2CF3 4-CF3 CH3 CH3 H H O 3-F 4-CN 4-OCF3 CH3 CH3 H H O 3-F 3,4-F2 4-Cl CH3 CH3 H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 71] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HH CH 3 CH 3 O 3-F 4-F 4-Cl HH CH 3 CH 3 O 3-F 4-F 4-Br HH CH 3 CH 3 O 3-F 4-F 4-CF 3 HH CH 3 CH 3 O 3-F 4-F 4-OCF 3 HH CH 3 CH 3 O 3-F 4-F 4-OCHF 2 HH CH 3 CH 3 O 3-F 4-F 4-OCF 2 Br HH CH 3 CH 3 O 3-F 4-F 4-OCF 2 CHF 2 HH CH 3 CH 3 O 3-F 4-F 4-OSO 2 CF 3 HH CH 3 CH 3 OH 4-F 4-OCF 3 HH CH 3 CH 3 O 4-F 4-F 4-Cl HH CH 3 CH 3 O 3-Cl 4-F 4-CF 3 HH CH 3 CH 3 O 3-Br 4-F 4-OCF 3 HH CH 3 CH 3 O 3-CF 3 4-F 4-Cl CH 3 CH 3 HHO 3-OCF 3 4-F 4-CF 3 CH 3 CH 3 HHO 3-OCHF 2 4-F 4-OCF 3 CH 3 CH 3 HHO 4-OCHF 2 4-F 4-Cl CH 3 CH 3 HHO 3-F 4-Cl 4-CF 3 CH 3 CH 3 HHO 3-F 4-Br 4-OCF 3 CH 3 CH 3 HHO 3-F 4-CF 3 4-Cl CH 3 CH 3 HHO 3-F 4-OSO 2 CF 3 4-CF 3 CH 3 CH 3 HHO 3-F 4-CN 4-OCF 3 CH 3 CH 3 HHO 3-F 3,4-F 2 4-Cl CH 3 CH 3 HHO 3-CF 3 4-CN 4 -CF 3 ──── ──────────────────────────────
【０１０６】[0106]
【表７２】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H H CH2OCH3 CH3 O 3-F 4-F 4-Cl H H COCH3 CH3 O 3-F 4-F 4-Br H H CO2CH3 CH3 O 3-F 4-F 4-CF3 H H CHF2 CH3 O 3-F 4-F 4-OCF3 H H CH2C6H5 CH3 O 3-F 4-F 4-OCHF2 H H SC6H5 CH3 O 3-F 4-F 4-OCF2Br H H CH3 CH2OCH3 O 3-F 4-F 4-OCF2CHF2 H H CH3 COCH3 O 3-F 4-F 4-OSO2CF3 H H CH3 CO2CH3 O H 4-F 4-OCF3 H H CH3 CHF2 O 4-F 4-F 4-Cl H H CH3 CH2C6H5 O 3-Cl 4-F 4-CF3 H H CH3 SC6H5 O 3-Br 4-F 4-OCF3 Br CH3 H H O 3-CF3 4-F 4-Cl CN CH3 H H O 3-OCF3 4-F 4-CF3 OH CH3 H H O 3-OCHF2 4-F 4-OCF3 C6H5 CH3 H H O 4-OCHF2 4-F 4-Cl CH2C6H5 CH3 H H O 3-F 4-Cl 4-CF3 C6H5 CO2CH3 H H O 3-F 4-Br 4-OCF3 CH3 CH2OCH3 H H O 3-F 4-CF3 4-Cl CH3 COCH3 H H O 3-F 4-OSO2CF3 4-CF3 CH3 CO2CH3 H H O 3-F 4-CN 4-OCF3 CH3 CHF2 H H O 3-F 3,4-F2 4-Cl CH3 CH2C6H5 H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 72] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── HH CH 2 OCH 3 CH 3 O 3-F 4 -F 4-Cl HH COCH 3 CH 3 O 3-F 4-F 4-Br HH CO 2 CH 3 CH 3 O 3-F 4-F 4-CF 3 HH CHF 2 CH 3 O 3-F 4-F 4-OCF 3 HH CH 2 C 6 H 5 CH 3 O 3-F 4-F 4-OCHF 2 HH SC 6 H 5 CH 3 O 3-F 4-F 4-OCF 2 Br HH CH 3 CH 2 OCH 3 O 3-F 4-F 4-OCF 2 CHF 2 HH CH 3 COCH 3 O 3-F 4-F 4-OSO 2 CF 3 HH CH 3 CO 2 CH 3 OH 4-F 4-OCF 3 HH CH 3 CHF 2 O 4-F 4-F 4-Cl HH CH 3 CH 2 C 6 H 5 O 3-Cl 4-F 4-CF 3 HH CH 3 SC 6 H 5 O 3-Br 4-F 4-OCF 3 Br CH 3 HHO 3-CF 3 4-F 4-Cl CN CH 3 HHO 3-OCF 3 4-F 4-CF 3 OH CH 3 HHO 3-OCHF 2 4-F 4-OCF 3 C 6 H 5 CH 3 HHO 4-OCHF 2 4-F 4-Cl CH 2 C 6 H 5 CH 3 HHO 3-F 4-Cl 4-CF 3 C 6 H 5 CO 2 CH 3 HHO 3-F 4-Br 4-OCF 3 CH 3 CH 2 OCH 3 HHO 3-F 4-CF 3 4-Cl CH 3 COCH 3 HHO 3-F 4-OSO 2 CF 3 4-CF 3 CH 3 CO 2 CH 3 HHO 3-F 4-CN 4-OCF 3 CH 3 CHF 2 HHO 3-F 3,4-F 2 4-Cl CH 3 CH 2 C 6 H 5 HHO 3-CF 3 4-CN 4-CF 3 ────────────── ──────────────────────
【０１０７】[0107]
【表７３】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── CH3 CO2CH3 H H O 3-F 4-F 4-Cl CH3 CO2CH3 H H O 3-F 4-F 4-Br CH3 CO2CH3 H H O 3-F 4-F 4-CF3 CH3 CO2CH3 H H O 3-F 4-F 4-OCF3 CH3 CO2CH3 H H O 3-F 4-F 4-OCHF2 CH3 CO2CH3 H H O 3-F 4-F 4-OCF2Br CH3 CO2CH3 H H O 3-F 4-F 4-OCF2CHF2 CH3 CO2CH3 H H O 3-F 4-F 4-OSO2CF3 CH3 CO2CH3 H H O H 4-F 4-OCF3 CH3 CO2CH3 H H S 4-F 4-F 4-Cl CH3 CO2CH3 H H O 3-Cl 4-F 4-CF3 CH3 CO2CH3 H H O 3-Br 4-F 4-OCF3 CH3 CO2CH3 H H O 3-CF3 4-F 4-Cl CH3 CO2CH3 H H O 3-OCF3 4-F 4-CF3 CH3 CO2CH3 H H O 3-OCHF2 4-F 4-OCF3 CH3 CO2CH3 H H O 4-OCHF2 4-F 4-Cl CH3 CO2CH3 H H S 3-F 4-Cl 4-CF3 CH3 CO2CH3 H H O 3-F 4-Br 4-OCF3 CH3 CO2CH3 H H O 3-F 4-CF3 4-Cl CH3 CO2CH3 H H O 3-F 4-OSO2CF3 4-CF3 CH3 CO2CH3 H H O 3-F 4-CN 4-OCF3 CH3 CO2CH3 H H O 3-F 3,4-F2 4-Cl CH3 CO2CH3 H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 73] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── CH 3 CO 2 CH 3 HHO 3-F 4- F 4-Cl CH 3 CO 2 CH 3 HHO 3-F 4-F 4-Br CH 3 CO 2 CH 3 HHO 3-F 4-F 4-CF 3 CH 3 CO 2 CH 3 HHO 3-F 4-F 4-OCF 3 CH 3 CO 2 CH 3 HHO 3-F 4-F 4-OCHF 2 CH 3 CO 2 CH 3 HHO 3-F 4-F 4-OCF 2 Br CH 3 CO 2 CH 3 HHO 3-F 4 -F 4-OCF 2 CHF 2 CH 3 CO 2 CH 3 HHO 3-F 4-F 4-OSO 2 CF 3 CH 3 CO 2 CH 3 HHOH 4-F 4-OCF 3 CH 3 CO 2 CH 3 HHS 4- F 4-F 4-Cl CH 3 CO 2 CH 3 HHO 3-Cl 4-F 4-CF 3 CH 3 CO 2 CH 3 HHO 3-Br 4-F 4-OCF 3 CH 3 CO 2 CH 3 HHO 3- CF 3 4-F 4-Cl CH 3 CO 2 CH 3 HHO 3-OCF 3 4-F 4-CF 3 CH 3 CO 2 CH 3 HHO 3-OCHF 2 4-F 4-OCF 3 CH 3 CO 2 CH 3 HHO 4-OCHF 2 4-F 4-Cl CH 3 CO 2 CH 3 HHS 3-F 4-Cl 4-CF 3 CH 3 CO 2 CH 3 HHO 3-F 4-Br 4-OCF 3 CH 3 CO 2 CH 3 HHO 3-F 4-CF 3 4-Cl CH 3 CO 2 CH 3 HHO 3-F 4-OSO 2 CF 3 4-CF 3 CH 3 CO 2 CH 3 HHO 3- F 4-CN 4-OCF 3 CH 3 CO 2 CH 3 HHO 3-F 3,4-F 2 4-Cl CH 3 CO 2 CH 3 HHO 3-CF 3 4-CN 4-CF 3 ───── ──────────────────────────────
【０１０８】[0108]
【表７４】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H CO2CH3 H CH3 O 3-F 4-F 4-Cl H CO2CH3 H CH3 O 3-F 4-F 4-Br H CO2CH3 H CH3 O 3-F 4-F 4-CF3 H CO2CH3 H CH3 O 3-F 4-F 4-OCF3 H CO2CH3 H CH3 O 3-F 4-F 4-OCHF2 H CO2CH3 H CH3 O 3-F 4-F 4-OCF2Br H CO2CH3 H CH3 O 3-F 4-F 4-OCF2CHF2 H CO2CH3 H CH3 O 3-F 4-F 4-OSO2CF3 H CO2CH3 H CH3 O H 4-F 4-OCF3 H CO2CH3 H CH3 S 4-F 4-F 4-Cl H CO2CH3 H CH3 O 3-Cl 4-F 4-CF3 H CO2CH3 H CH3 O 3-Br 4-F 4-OCF3 H CO2CH3 H CH3 O 3-CF3 4-F 4-Cl H CO2CH3 H CH3 O 3-OCF3 4-F 4-CF3 H CO2CH3 H CH3 O 3-OCHF2 4-F 4-OCF3 H CO2CH3 H CH3 O 4-OCHF2 4-F 4-Cl H CO2CH3 H CH3 S 3-F 4-Cl 4-CF3 H CO2CH3 H CH3 O 3-F 4-Br 4-OCF3 H CO2CH3 H CH3 O 3-F 4-CF3 4-Cl H CO2CH3 H CH3 O 3-F 4-OSO2CF3 4-CF3 H CO2CH3 H CH3 O 3-F 4-CN 4-OCF3 H CO2CH3 H CH3 O 3-F 3,4-F2 4-Cl H CO2CH3 H CH3 O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 74] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── H CO 2 CH 3 H CH 3 O 3-F 4-F 4-Cl H CO 2 CH 3 H CH 3 O 3-F 4-F 4-Br H CO 2 CH 3 H CH 3 O 3-F 4-F 4-CF 3 H CO 2 CH 3 H CH 3 O 3-F 4-F 4-OCF 3 H CO 2 CH 3 H CH 3 O 3-F 4-F 4-OCHF 2 H CO 2 CH 3 H CH 3 O 3-F 4-F 4-OCF 2 Br H CO 2 CH 3 H CH 3 O 3-F 4-F 4-OCF 2 CHF 2 H CO 2 CH 3 H CH 3 O 3-F 4-F 4-OSO 2 CF 3 H CO 2 CH 3 H CH 3 OH 4-F 4-OCF 3 H CO 2 CH 3 H CH 3 S 4-F 4-F 4-Cl H CO 2 CH 3 H CH 3 O 3-Cl 4-F 4-CF 3 H CO 2 CH 3 H CH 3 O 3-Br 4-F 4-OCF 3 H CO 2 CH 3 H CH 3 O 3-CF 3 4-F 4-Cl H CO 2 CH 3 H CH 3 O 3-OCF 3 4-F 4-CF 3 H CO 2 CH 3 H CH 3 O 3-OCHF 2 4-F 4-OCF 3 H CO 2 CH 3 H CH 3 O 4-OCHF 2 4-F 4-Cl H CO 2 CH 3 H CH 3 S 3-F 4-Cl 4-CF 3 H CO 2 CH 3 H CH 3 O 3-F 4-Br 4-OCF 3 H CO 2 CH 3 H CH 3 O 3-F 4-CF 3 4-Cl H CO 2 CH 3 H CH 3 O 3-F 4 -OSO 2 CF 3 4-CF 3 H CO 2 CH 3 H CH 3 O 3-F 4-CN 4-OCF 3 H CO 2 CH 3 H CH 3 O 3-F 3,4-F 2 4-Cl H CO 2 CH 3 H CH 3 O 3-CF 3 4-CN 4-CF 3 ──────────────────────────────── ────
【０１０９】[0109]
【表７５】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H CO2CH3 H H O 3-F 4-F 4-Cl H CO2CH3 H H O 3-F 4-F 4-Br H CO2CH3 H H O 3-F 4-F 4-CF3 H CO2CH3 H H O 3-F 4-F 4-OCF3 H CO2CH3 H H O 3-F 4-F 4-OCHF2 H CO2CH3 H H O 3-F 4-F 4-OCF2Br H CO2CH3 H H O 3-F 4-F 4-OCF2CHF2 H CO2CH3 H H O 3-F 4-F 4-OSO2CF3 H CO2CH3 H H O H 4-F 4-OCF3 H CO2CH3 H H S 4-F 4-F 4-Cl H CO2CH3 H H O 3-Cl 4-F 4-CF3 H CO2CH3 H H O 3-Br 4-F 4-OCF3 H CO2CH3 H H O 3-CF3 4-F 4-Cl H CO2CH3 H H O 3-OCF3 4-F 4-CF3 H CO2CH3 H H O 3-OCHF2 4-F 4-OCF3 H CO2CH3 H H O 4-OCHF2 4-F 4-Cl H CO2CH3 H H S 3-F 4-Cl 4-CF3 H CO2CH3 H H O 3-F 4-Br 4-OCF3 H CO2CH3 H H O 3-F 4-CF3 4-Cl H CO2CH3 H H O 3-F 4-OSO2CF3 4-CF3 H CO2CH3 H H O 3-F 4-CN 4-OCF3 H CO2CH3 H H O 3-F 3,4-F2 4-Cl H CO2CH3 H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 75] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── H CO 2 CH 3 HHO 3-F 4-F 4-Cl H CO 2 CH 3 HHO 3-F 4-F 4-Br H CO 2 CH 3 HHO 3-F 4-F 4-CF 3 H CO 2 CH 3 HHO 3-F 4-F 4-OCF 3 H CO 2 CH 3 HHO 3-F 4-F 4-OCHF 2 H CO 2 CH 3 HHO 3-F 4-F 4-OCF 2 Br H CO 2 CH 3 HHO 3-F 4-F 4-OCF 2 CHF 2 H CO 2 CH 3 HHO 3-F 4-F 4-OSO 2 CF 3 H CO 2 CH 3 HHOH 4-F 4-OCF 3 H CO 2 CH 3 HHS 4-F 4-F 4-Cl H CO 2 CH 3 HHO 3-Cl 4-F 4-CF 3 H CO 2 CH 3 HHO 3-Br 4-F 4-OCF 3 H CO 2 CH 3 HHO 3-CF 3 4-F 4-Cl H CO 2 CH 3 HHO 3-OCF 3 4-F 4-CF 3 H CO 2 CH 3 HHO 3-OCHF 2 4-F 4-OCF 3 H CO 2 CH 3 HHO 4-OCHF 2 4-F 4-Cl H CO 2 CH 3 HHS 3-F 4-Cl 4-CF 3 H CO 2 CH 3 HHO 3-F 4-Br 4-OCF 3 H CO 2 CH 3 HHO 3-F 4-CF 3 4-Cl H CO 2 CH 3 HHO 3 -F 4-OSO 2 CF 3 4-CF 3 H CO 2 CH 3 HHO 3-F 4-CN 4-OCF 3 H CO 2 CH 3 HHO 3-F 3,4-F 2 4-Cl H CO 2 CH 3 HHO 3-CF 3 4-CN 4-CF 3 ───────────────────────────────────
【０１１０】[0110]
【表７６】 ─────────────────────────────────── R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── H CH3 H CH3 O 3-F 4-F 4-Cl H CH3 H CH3 O 3-F 4-F 4-Br H CH3 H CH3 O 3-F 4-F 4-CF3 H CH3 H CH3 O 3-F 4-F 4-OCF3 H CH3 H CH3 O 3-F 4-F 4-OCHF2 H CH3 H CH3 O 3-F 4-F 4-OCF2Br H CH3 H CH3 O 3-F 4-F 4-OCF2CHF2 H CH3 H CH3 O 3-F 4-F 4-OSO2CF3 H CH3 H CH3 O H 4-F 4-OCF3 H CH3 H CH3 S 4-F 4-F 4-Cl H CH3 H CH3 O 3-Cl 4-F 4-CF3 H CH3 H CH3 O 3-Br 4-F 4-OCF3 H CH3 H CH3 O 3-CF3 4-F 4-Cl H CH3 H CH3 O 3-OCF3 4-F 4-CF3 H CH3 H CH3 O 3-OCHF2 4-F 4-OCF3 H CH3 H CH3 O 4-OCHF2 4-F 4-Cl H CH3 H CH3 S 3-F 4-Cl 4-CF3 H CH3 H CH3 O 3-F 4-Br 4-OCF3 H CH3 H CH3 O 3-F 4-CF3 4-Cl H CH3 H CH3 O 3-F 4-OSO2CF3 4-CF3 H CH3 H CH3 O 3-F 4-CN 4-OCF3 H CH3 H CH3 O 3-F 3,4-F2 4-Cl H CH3 H CH3 O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 76] ─────────────────────────────────── R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── H CH 3 H CH 3 O 3-F 4- F 4-Cl H CH 3 H CH 3 O 3-F 4-F 4-Br H CH 3 H CH 3 O 3-F 4-F 4-CF 3 H CH 3 H CH 3 O 3-F 4-F 4-OCF 3 H CH 3 H CH 3 O 3-F 4-F 4-OCHF 2 H CH 3 H CH 3 O 3-F 4-F 4-OCF 2 Br H CH 3 H CH 3 O 3-F 4 -F 4-OCF 2 CHF 2 H CH 3 H CH 3 O 3-F 4-F 4-OSO 2 CF 3 H CH 3 H CH 3 OH 4-F 4-OCF 3 H CH 3 H CH 3 S 4- F 4-F 4-Cl H CH 3 H CH 3 O 3-Cl 4-F 4-CF 3 H CH 3 H CH 3 O 3-Br 4-F 4-OCF 3 H CH 3 H CH 3 O 3- CF 3 4-F 4-Cl H CH 3 H CH 3 O 3-OCF 3 4-F 4-CF 3 H CH 3 H CH 3 O 3-OCHF 2 4-F 4-OCF 3 H CH 3 H CH 3 O 4-OCHF 2 4-F 4-Cl H CH 3 H CH 3 S 3-F 4-Cl 4-CF 3 H CH 3 H CH 3 O 3-F 4-Br 4-OCF 3 H CH 3 H CH 3 O 3-F 4-CF 3 4-Cl H CH 3 H CH 3 O 3-F 4-OSO 2 CF 3 4-CF 3 H CH 3 H CH 3 O 3-F 4-CN 4-OCF 3 H CH 3 H CH 3 O 3-F 3,4-F 2 4-Cl H CH 3 H CH 3 O 3-CF 3 4-CN 4-CF 3 ───────────────────────────────────
【０１１１】本発明において有害生物防除剤とは、特に
害虫防除剤及び植物病害防除剤を意味する。本発明化合
物は極めて低い薬剤濃度で各種の有害な害虫に対して効
力を示す。その害虫としては、例えば、ツマグロヨコバ
イ、トビイロウンカ、モモアカアブラムシ、ニジュウヤ
ホシテントウ、ハスモンヨトウ、コブノメイガ、コナガ
等の農業害虫、ナミハダニ、ミカンハダニ、カンザワハ
ダニ等のハダニ類、アカイエカ、イエバエ、チャバネゴ
キブリ、アリ、ノミ、シラミ等の衛生害虫、コクゾウム
シ、コクヌストモドキ、スジマダラメイガ等の貯穀害
虫、シロアリのような家屋害虫、ダニ、ノミ、シラミ等
の家畜害虫、コナダニ、ヒョウヒダニ、ツメダニ等の屋
内塵性ダニ、ナメクジ、カタツムリ等の軟体動物等が挙
げられる。すなわち、本発明化合物は直翅目、半翅目、
鱗翅目、鞘翅目、膜翅目、双翅目、シロアリ目およびダ
ニ・シラミ類の害虫を低濃度で有効に防除できる。In the present invention, the pest controlling agent means especially a pest controlling agent and a plant disease controlling agent. The compounds of the present invention are effective against various harmful pests at extremely low drug concentrations. Examples of the pests include agricultural pests such as leafhoppers, brown planthoppers, green peach aphids, pearl moss aphids, scutellaria japonicus, sphagnum moss, spider mites, citrus spider mites, kanzawa mites, mosquitoes, house flies, mosquitoes, and cockroaches. Hygiene pests such as lice, weevil, stag beetle, stored grain pests such as striped moth, house pests such as termites, livestock pests such as mites, fleas, lice, indoor dust mites such as mites, leopard mites, tick mites, slugs, Examples include molluscs such as snails. That is, the compound of the present invention is an orthoptera, a hemiptera,
It can effectively control pests of Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites and mites and lice at low concentrations.
【０１１２】次に、本発明化合物の対象となる植物病害
としては、イネのいもち病(Pyricularia oryzae)、ごま
葉枯病(Cochliobolus miyabeanus)、紋枯病(Rhizoctoni
a solani)、ムギ類のうどんこ病(Erysiphe graminis f.
sp.hordei,f. sp.tritici)、斑葉病(Pyrenophora grami
nea)、網斑病(Pyrenophora teres)、赤かび病(Gibberel
la zeae)、さび病(Puccinia striiformis, P.graminis,
P.recondita, P.hordei)、雪腐病(Typhula sp.,Micron
ectriella nivais)、裸黒穂病(Ustilago tritici,U.nud
a)、アイスポット(Pseudocercosporella herpotrichoid
es)、雲形病(Rhynchosporium secalis)、葉枯病(Septor
ia tritici)、ふ枯病(Leptosphaeria nodorum)、カンキ
ツの黒点病(Diaporthe citri)、そうか病(Elsinoe fawc
etti)、果実腐敗病(Penicillium digitatum,P.italicu
m)、リンゴのモニリア病(Sclerotinia mali)、腐らん病
(Valsa mali) 、うどんこ病(Podosphaera leucotrich
a)、斑点落葉病(Alternaria mali)、黒星病(Venturia i
naequalis)、ナシの黒星病(Venturia nashicola)、黒斑
病(Alternaria Kikuchiana)、赤星病(Gymnosporangium
haraeanum)、モモの灰星病(Sclerotinia cinerea)、黒
星病(Cladosporium carpophilum)、フォモプシス腐敗病
(Phomopsis sp.)、ブドウのべと病(Plasmoparaviticol
a)、黒とう病(Elsinoe ampelina) 、晩腐病(Glomerella
cingulata)、うどんこ病(Uncinula necator)、さび病
(Phakopsora ampelopsidis)、カキの炭そ病(Gloeospori
um kaki) 、落葉病(Cercospora kaki, Mycosphaerella
nawae)、ウリ類のべと病(Pseudoperenospora cubensi
s)、炭そ病(Colletotrichum lagenarium)、うどんこ病
(Sphaerotheca fuliginea)、つる枯病(Mycosphaerella
melonis) 、トマトの疫病(Phytophthora infestans) 、
輪紋病(Alternaria solani)、葉かび病(Cladosporium f
ulvam)、ナスの褐紋病(Phomopsis vexans)、うどんこ病
(Erysiphe cichoracoarum)、アブラナ科野菜の黒斑病(A
lternaria japonica)、白斑病(Cerocosporella brassic
ae)、ネギのさび病(Puccinia allii)、ダイズの紫斑病
(Cercospora kikuchii)、黒とう病(Elsinoe glycine
s)、黒点病(Diaporthe phaseololum)、インゲンの炭そ
病(Colletotrichum lindemuthianum)、ラッカセイの黒
渋病(Mycosphaerella personatum)、褐斑病(Cercospora
arachidicola)、エンドウのうどんこ病(Erysiphe pis
i)、ジャガイモの夏疫病(Alternaria solani)、イチゴ
のうどんこ病(Sphaerotheca humuli)、チャの網もち病
(Exobasidium reticulatum)、白星病(Elsinoe leucospi
la)、タバコの赤星病(Alternarialongipes)、うどんこ
病(Erysiphe cichoracearum) 、炭そ病(Colletotrichum
tabacum)、テンサイの褐斑病(Cercospora beticola)、
バラの黒星病(Diplocarponrosae) 、うどんこ病(Sphaer
otheca pannosa)、キクの褐斑病(Septoria chrysanthem
iindici)、白さび病(Puccinia horiana) 、種々の作物
の灰色かび病(Botrytis cinerea) 、菌核病(Sclerotini
a sclerotiorum) 等が挙げられる。Next, the plant diseases targeted by the compound of the present invention include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and blight (Rhizoctoni).
a solani), powdery mildew of wheat (Erysiphe graminis f.
sp.hordei, f.sp.tritici), leaf spot (Pyrenophora grami)
nea), net blotch (Pyrenophora teres), and Fusarium head blight (Gibberel)
la zeae), rust (Puccinia striiformis, P. graminis,
P. recondita, P. hordei), Snow rot (Typhula sp., Micron
ectriella nivais), naked smut (Ustilago tritici, U.nud
a), eye spot (Pseudocercosporella herpotrichoid
es), cloud disease (Rhynchosporium secalis), leaf blight (Septor
ia tritici), bacterial wilt (Leptosphaeria nodorum), citrus black spot (Diaporthe citri), scab (Elsinoe fawc)
etti), fruit rot (Penicillium digitatum, P.italicu
m), monili disease of apple (Sclerotinia mali), rot
(Valsa mali), powdery mildew (Podosphaera leucotrich
a), leaf spot disease (Alternaria mali), scab (Venturia i)
naequalis), pear scab (Venturia nashicola), black spot (Alternaria Kikuchiana), scab (Gymnosporangium)
haraeanum), Peach scab (Sclerotinia cinerea), scab (Cladosporium carpophilum), Phomopsis rot
(Phomopsis sp.), Downy mildew of grape (Plasmoparaviticol
a), black rot (Elsinoe ampelina), late rot (Glomerella)
cingulata), powdery mildew (Uncinula necator), rust
(Phakopsora ampelopsidis), oyster anthracnose (Gloeospori
um kaki), leaf blight (Cercospora kaki, Mycosphaerella
nawae), downy mildew of smelt (Pseudoperenospora cubensi)
s), anthracnose (Colletotrichum lagenarium), powdery mildew
(Sphaerotheca fuliginea), vine blight (Mycosphaerella)
melonis), tomato plague (Phytophthora infestans),
Leaf spot (Alternaria solani), leaf mold (Cladosporium f)
ulvam), eggplant brown leaf spot (Phomopsis vexans), powdery mildew
(Erysiphe cichoracoarum), black spot of cruciferous vegetables (A
lternaria japonica), vitiligo (Cerocosporella brassic)
ae), green onion rust (Puccinia allii), soybean purpura
(Cercospora kikuchii), black spot (Elsinoe glycine
s), black spot (Diapor the phaseololum), anthracnose of kidney bean (Colletotrichum lindemuthianum), black spot of peanut (Mycosphaerella personatum), brown spot (Cercospora)
arachidicola), powdery mildew of pea (Erysiphe pis
i), Potato summer blight (Alternaria solani), Strawberry powdery mildew (Sphaerotheca humuli), Tea net blast
(Exobasidium reticulatum), white scab (Elsinoe leucospi
la), tobacco scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum)
tabacum), brown leaf spot of sugar beet (Cercospora beticola),
Rose scab (Diplocarpon rosae), powdery mildew (Sphaer)
otheca pannosa), brown spot of chrysanthemum (Septoria chrysanthem)
iindici), white rust (Puccinia horiana), gray mold of various crops (Botrytis cinerea), sclerotini (Sclerotini)
a sclerotiorum) and the like.
【０１１３】一方、本発明化合物はホ乳類、魚類、甲殻
類および益虫に対してはほとんど悪影響がない極めて有
用な化合物であることを見出し、本発明を完成した。On the other hand, the compound of the present invention was found to be an extremely useful compound having almost no adverse effect on mammals, fish, crustaceans and beneficial insects, and completed the present invention.
【０１１４】次に、本発明化合物の製造法について説明
する。本発明化合物は新規なセミカルバゾン化合物であ
り、代表的な製造法を以下に具体的に説明する。Next, a method for producing the compound of the present invention will be described. The compound of the present invention is a novel semicarbazone compound, and a typical production method will be specifically described below.
【０１１５】各方法（Ａ法〜Ｆ法）において、Ｗ、Ｘ、
Ｙ、Ｚ、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 、ｌ、ｍ及びｎは前記
と同じ意味を示し、Ｌ1 及びＬ2 は、塩素原子、臭素原
子、ヨウ素原子、アルキルスルホネート基又はアリール
スルホネート基のような良好な脱離基を示す。In each method (method A to method F), W, X,
Y, Z, R 1 , R 2 , R 3 , R 4 , 1, m and n have the same meanings as described above, and L 1 and L 2 are chlorine atom, bromine atom, iodine atom, alkyl sulfonate group or aryl. It shows a good leaving group such as a sulfonate group.
【０１１６】Ａ法Method A
【０１１７】[0117]
【化５】 [Chemical 5]
【０１１８】化合物［II］と化合物［III］とを触媒の
存在下又は不存在下、不活性な溶媒中で反応させること
により本発明化合物［Ｉ］が得られる。本反応において
用いられる触媒としては塩酸、硫酸等の無機酸又はパラ
トルエンスルホン酸等の有機酸等が挙げられる。触媒の
使用量は化合物［II］に対して０．００１重量％から１
０重量％までの任意の量を設定できるが、０．１重量％
から１重量％が好ましい。溶媒としては反応の進行を阻
害しないものであれば良く、例えばメタノール、エタノ
ール、プロパノール、ブタノール等の低級アルコール
類、ベンゼン、トルエン等の芳香族炭化水素類、ジエチ
ルエーテル、１，２−ジメトキシエタン、テトラヒドロ
フラン、１，４−ジオキサン等のエーテル類、ジクロロ
メタン、クロロホルム、四塩化炭素等のハロゲン化炭化
水素類、ジメチルホルムアミド、ジメチルアセトアミド
等のアミド類、アセトニトリル、ジメチルスルホキシ
ド、酢酸、水等が挙げられる。これらの不活性溶媒は単
独で使用してもよく、また、混合して使用することもで
きる。一般的にはメタノール、エタノール等の低級アル
コール中で触媒として塩酸を用いるのが好ましい。反応
温度は−６０℃から反応混合物の還流温度までの任意の
温度を設定することができるが、室温から反応混合物の
還流温度で行なうのが好ましい。The compound [I] of the present invention is obtained by reacting the compound [II] with the compound [III] in the presence or absence of a catalyst in an inert solvent. Examples of the catalyst used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as paratoluenesulfonic acid. The amount of the catalyst used is 0.001% by weight to 1 based on the compound [II].
Any amount up to 0% by weight can be set, but 0.1% by weight
To 1% by weight is preferred. Any solvent may be used as long as it does not hinder the progress of the reaction, for example, lower alcohols such as methanol, ethanol, propanol and butanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, 1,2-dimethoxyethane, Examples thereof include ethers such as tetrahydrofuran and 1,4-dioxane, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide, acetic acid, water and the like. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use hydrochloric acid as a catalyst in a lower alcohol such as methanol or ethanol. The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, but it is preferably carried out at room temperature to the reflux temperature of the reaction mixture.
【０１１９】Ｂ法Method B
【０１２０】[0120]
【化６】 [Chemical 6]
【０１２１】本法は本発明化合物［Ｉ］のＲ4 が水素原
子である化合物［VII］の製造法である。化合物［II］
と化合物［IV］とを触媒の存在下又は不存在下、不活性
な溶媒中で反応させることにより化合物［Ｖ］とし、該
化合物［Ｖ］を単離し、もしくは単離せずして、化合物
［VI］と触媒の存在下又は不存在下、不活性な溶媒中で
反応させることにより本発明化合物［VII］を得ること
ができる。Ｂ１工程において用いられる触媒及び溶媒と
してはＡ法と同様である。化合物［IV］で表されるヒド
ラジン類の使用量は化合物［II］に対して等モルないし
過剰に使用することができるが、２〜５倍モル用いるの
が好ましい。反応温度は室温から反応混合物の還流温度
までの任意の温度を設定することができる。一般的には
メタノール、エタノール等の低級アルコール中で還流温
度で反応するのが好ましい。This method is a method for producing a compound [VII] in which R 4 of the compound [I] of the present invention is a hydrogen atom. Compound [II]
To react with compound [IV] in the presence or absence of a catalyst in an inert solvent to give compound [V], which may or may not be isolated. The compound [VII] of the present invention can be obtained by reacting VI] with an inert solvent in the presence or absence of a catalyst. The catalyst and solvent used in Step B1 are the same as those in Method A. The hydrazines represented by the compound [IV] can be used in an equimolar or excess amount with respect to the compound [II], but it is preferably used in an amount of 2 to 5 times. The reaction temperature can be set to any temperature from room temperature to the reflux temperature of the reaction mixture. Generally, it is preferable to react at a reflux temperature in a lower alcohol such as methanol or ethanol.
【０１２２】Ｂ２工程において用いられる触媒としては
トリエチレンジアミン、ジアザビシクロウンデセン等の
有機塩基等が挙げられる。触媒の使用量は化合物［Ｖ］
に対して０．００１重量％から１０重量％までの任意の
量を設定できるが、０．１重量％から１重量％が好まし
い。溶媒としては反応の進行を阻害しないものであれば
良く、例えば、ベンゼン、トルエン等の芳香族炭化水素
類、ジエチルエーテル、テトラヒドロフラン等のエーテ
ル類、ジクロロメタン、クロロホルム等のハロゲン化炭
化水素類、ジメチルホルムアミド、ジメチルアセトアミ
ド等のアミド類、アセトニトリル、ジメチルスルホキシ
ドおよび水等が挙げられる。これらの不活性溶媒は単独
で使用してもよく、また、混合して使用することもでき
る。反応温度は−６０℃から反応混合物の還流温度まで
の任意の温度を設定することができるが、０℃から５０
℃で行うのが好ましい。Examples of the catalyst used in the step B2 include organic bases such as triethylenediamine and diazabicycloundecene. The amount of catalyst used is compound [V]
Can be set to any amount from 0.001% by weight to 10% by weight, but 0.1% by weight to 1% by weight is preferable. Any solvent may be used as long as it does not inhibit the progress of the reaction, and examples thereof include aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and chloroform, and dimethylformamide. , Amides such as dimethylacetamide, acetonitrile, dimethylsulfoxide, water and the like. These inert solvents may be used alone or in a mixture. The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, but 0 ° C. to 50 ° C.
It is preferable to carry out at ° C.
【０１２３】Ｃ法Method C
【０１２４】[0124]
【化７】 [Chemical 7]
【０１２５】本法は、Ｒ3＝Ｒ4＝水素原子である場合
に、Ｒ3、Ｒ4を導入する方法である。本発明化合物［VI
II］と化合物［IX］を塩基の存在下、不活性な溶媒中で
反応させることにより本発明化合物［VII］を得ること
ができる。つづいて、本発明化合物［VII］と化合物
［Ｘ］を塩基の存在下、不活性な溶媒中で反応させるこ
とにより本発明化合物［Ｉ］が得られる。本反応におい
て、用いられる塩基としてはナトリウムエトキシド、カ
リウムターシャリーブトキシドのようなアルカリ金属ア
ルコキシド類、水酸化ナトリウム、水酸化カリウム等の
アルカリ金属水酸化物、炭酸ナトリウム、炭酸カリウ
ム、炭酸水素ナトリウム等のアルカリ金属炭酸塩、水素
化ナトリウム、水素化カリウム等のアルカリ金属水素化
物、トリエチルアミン、ピリジン等の有機塩基等が挙げ
られる。用いられる溶媒としては、反応の進行を阻害し
ないものであれば良く、例えばメタノール、エタノール
等の低級アルコール類、ベンゼン、トルエン等の芳香族
炭化水素類、ジエチルエーテル、１，２−ジメトキシエ
タン、テトラヒドロフラン、１，４−ジオキサン等のエ
ーテル類、ジクロロメタン、１，２−ジクロロエタン等
のハロゲン化炭化水素類、ジメチルホルムアミド、ジメ
チルアセトアミド等のアミド類、アセトニトリル、ジメ
チルスルホキシドおよび水等が挙げられる。これらの不
活性溶媒は単独で使用してもよく、また、混合して使用
することもできる。一般的にはテトラヒドロフランやジ
メチルホルムアミド等の極性溶媒中で、塩基として水素
化ナトリウム、水素化カリウム、カリウムターシャリー
ブトキシド又は水酸化カリウムを用いるのが好ましい。
反応温度は−６０℃から反応混合物の還流温度までの任
意の温度を設定することができるが、０℃から９０℃ま
でで行なうのが好ましい。本反応においてＲ3＝Ｒ4の場
合は２当量の化合物［IX］と２当量の塩基を用いること
により、化合物［VII］を単離することなく、本発明化
合物［Ｉ］を得ることができる。This method is a method of introducing R 3 and R 4 when R 3 = R 4 = hydrogen atom. The compound of the present invention [VI
The compound [VII] of the present invention can be obtained by reacting II] with the compound [IX] in the presence of a base in an inert solvent. Then, the compound [VII] of the present invention is reacted with the compound [X] in the presence of a base in an inert solvent to obtain the compound [I] of the present invention. In this reaction, as the base to be used, alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, etc. Alkali metal carbonates, alkali metal hydrides such as sodium hydride and potassium hydride, and organic bases such as triethylamine and pyridine. Any solvent may be used as long as it does not inhibit the progress of the reaction, and examples thereof include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, 1,2-dimethoxyethane, and tetrahydrofuran. , Ethers such as 1,4-dioxane, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use sodium hydride, potassium hydride, potassium tert-butoxide or potassium hydroxide as a base in a polar solvent such as tetrahydrofuran or dimethylformamide.
The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 90 ° C. In the present reaction, when R 3 = R 4 , the compound [IX] of the present invention can be obtained by isolating the compound [VII] by using 2 equivalents of the compound [IX] and 2 equivalents of the base. .
【０１２６】Ｄ法Method D
【０１２７】[0127]
【化８】 [Chemical 8]
【０１２８】出発原料の化合物［II］は化合物［XI］と
化合物［XII］を塩基の存在下又は不存在下、不活性な
溶媒中で反応させることにより得られる。本反応におい
て用いられる塩基としては、ナトリウムエトキシド、カ
リウムターシャリーブトキシドのようなアルカリ金属ア
ルコキシド類、水酸化ナトリウム、水酸化カリウム等の
アルカリ金属水酸化物、炭酸ナトリウム、炭酸カリウ
ム、炭酸水素ナトリウム等のアルカリ金属炭酸塩、水素
化ナトリウム、水素化カリウム等のアルカリ金属水素化
物、トリエチルアミン、ピリジン等の有機塩基等が挙げ
られる。用いられる溶媒としては、反応の進行を阻害し
ないものであれば良く、例えばメタノール、エタノール
等の低級アルコール類、ベンゼン、トルエン等の芳香族
炭化水素類、ジエチルエーテル、テトラヒドロフラン等
のエーテル類、アセトン、メチルエチルケトン等のケト
ン類、ジメチルホルムアミド、ジメチルアセトアミド等
のアミド類、アセトニトリル、ジメチルスルホキシドお
よび水等が挙げられる。これらの不活性溶媒は単独で使
用してもよく、また、混合して使用することもできる。
一般的にはメタノール、エタノールやアセトン等の極性
溶媒中で、塩基として炭酸カリウム、炭酸水素ナトリウ
ム等のアルカリ金属炭酸塩を用いるのが好ましい。反応
温度は−７０℃から反応混合物の還流温度までの任意の
温度を設定することができるが、室温から還流温度で行
うのが好ましい。The compound [II] as a starting material can be obtained by reacting the compound [XI] with the compound [XII] in the presence or absence of a base in an inert solvent. Examples of the base used in this reaction include alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydrogen carbonate. Alkali metal carbonates, alkali metal hydrides such as sodium hydride and potassium hydride, and organic bases such as triethylamine and pyridine. The solvent used may be one that does not inhibit the progress of the reaction, for example, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, acetone, Examples thereof include ketones such as methyl ethyl ketone, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide and water. These inert solvents may be used alone or in a mixture.
Generally, it is preferable to use an alkali metal carbonate such as potassium carbonate or sodium hydrogen carbonate as a base in a polar solvent such as methanol, ethanol or acetone. The reaction temperature can be set at any temperature from -70 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out at room temperature to the reflux temperature.
【０１２９】Ｅ法Method E
【０１３０】[0130]
【化９】 [Chemical 9]
【０１３１】本法は、Ｒ3＝Ｒ4＝水素原子である場合の
出発原料（化合物［III］のＲ3＝Ｒ 4＝水素原子）の合
成法である。化合物［XIII］と化合物［VI］を触媒の存
在下又は不存在下、不活性な溶媒中で反応させることに
より化合物［XIV］が得られる。本反応において用いら
れる触媒としては、トリエチレンジアミン、ジアザビシ
クロウンデセン等の有機塩基等が挙げられる。触媒の使
用量は化合物［VI］に対して０．００１重量％から１０
重量％までの任意の量を設定できるが、０．１重量％か
ら１重量％が好ましい。溶媒としては反応の進行を阻害
しないものであれば良く、例えば、ベンゼン、トルエン
等の芳香族炭化水素類、ジエチルエーテル、テトラヒド
ロフラン等のエーテル類、ジクロロメタン、クロロホル
ム等のハロゲン化炭化水素類、ジメチルホルムアミド、
ジメチルアセトアミド等のアミド類、アセトニトリル、
ジメチルスルホキシドおよび水等が挙げられる。これら
の不活性溶媒は単独で使用してもよく、また、混合して
使用することもできる。反応温度は−６０℃から反応混
合物の還流温度までの任意の温度を設定することができ
るが、０℃から５０℃で行うのが好ましい。この反応に
おいて反応物質のモル比には特に制限はないが化合物
［XIV］を収率よく得るためには、化合物［VI］に対し
て化合物［XIII］を少し過剰に用いるのが好ましい。This method uses R3= RFour= When hydrogen atom
Starting material (R of compound [III]3= R Four= Hydrogen atom)
It is a law. Compound [XIII] and compound [VI] are used as catalysts.
To react in an inert solvent in the presence or absence of
The compound [XIV] is obtained. Used in this reaction
The catalysts used are triethylenediamine and diazabis
Examples thereof include organic bases such as cloundecene. Use of catalyst
The dose is 0.001% by weight to 10% based on the compound [VI].
Any amount up to wt% can be set, but 0.1 wt%
1% by weight is preferable. Inhibits the progress of the reaction as a solvent
If it does not, for example, benzene, toluene
Aromatic hydrocarbons such as, diethyl ether, tetrahydr
Ethers such as lofuran, dichloromethane, chloroform
Halogenated hydrocarbons such as dimethylformamide, dimethylformamide,
Amides such as dimethylacetamide, acetonitrile,
Examples include dimethyl sulfoxide and water. these
The inert solvent of may be used alone or in a mixture.
It can also be used. The reaction temperature is from -60 ℃
You can set any temperature up to the reflux temperature of the compound
However, it is preferably carried out at 0 ° C to 50 ° C. To this reaction
The molar ratio of the reactants is not particularly limited, but the compound
In order to obtain [XIV] in good yield,
It is preferable to use the compound [XIII] in a slight excess.
【０１３２】Ｆ法Method F
【０１３３】[0133]
【化１０】 [Chemical 10]
【０１３４】本法は、Ｅ法の別法で、Ｒ3＝Ｒ4＝水素原
子である場合の出発原料（化合物［III］のＲ3＝Ｒ4＝
水素原子）の合成法である。化合物［XV］と化合物［V
I］を触媒の存在下又は不存在下、不活性な溶媒中で反
応させることにより化合物［XVI］が得られる。本反応
において用いられる触媒、溶媒及び温度等の反応条件は
Ｅ法と同じである。本法においては、当モルの化合物
［XV］と化合物［VI］を用いて収率よく化合物［XVI］
を得ることができるのが特徴である。工程２において、
化合物［XVI］を酸の存在下、不活性な溶媒中で反応さ
せることにより、化合物［XIV］を得ることができる。
用いられる酸としては、塩酸、硫酸等の無機酸、パラト
ルエンスルホン酸、トリフルオロ酢酸等の有機酸等が挙
げられる。溶媒としては、反応の進行を阻害しないもの
であれば良く、例えば、メタノール、エタノール等の低
級アルコール類、ベンゼン、トルエン等の芳香族炭化水
素類、ジエチルエーテル、テトラヒドロフラン等のエー
テル類、ジクロロメタン、四塩化炭素等のハロゲン化炭
化水素類、ジメチルホルムアミド、ジメチルアセトアミ
ド等のアミド類、アセトニトリル、ジメチルスルホキシ
ド、酢酸および水等が挙げられる。これらの不活性溶媒
は単独で使用してもよく、また、混合して使用すること
もできる。一般的には、メタノール、エタノール等の低
級アルコール中で過剰量の塩酸を用いるのが好ましい。
反応温度は−６０℃から反応混合物の還流温度までの任
意の温度を設定することができるが、０℃から反応混合
物の還流温度で行うのが好ましい。This method is an alternative to the method E, in which R 3 = R 4 = hydrogen atom, the starting material (R 3 = R 4 = of the compound [III])
Hydrogen atom) is a synthetic method. Compound [XV] and Compound [V
Compound [XVI] is obtained by reacting [I] in the presence or absence of a catalyst in an inert solvent. The reaction conditions such as catalyst, solvent and temperature used in this reaction are the same as those in Method E. In this method, equimolar amounts of compound [XV] and compound [VI] are used to yield compound [XVI] in good yield.
The feature is that In step 2,
Compound [XVI] can be obtained by reacting compound [XVI] in the presence of an acid in an inert solvent.
Examples of the acid used include inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as paratoluenesulfonic acid and trifluoroacetic acid, and the like. Any solvent may be used as long as it does not hinder the progress of the reaction, and examples thereof include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, dichloromethane, and four. Examples thereof include halogenated hydrocarbons such as carbon chloride, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide, acetic acid and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use an excess amount of hydrochloric acid in a lower alcohol such as methanol or ethanol.
The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to the reflux temperature of the reaction mixture.
【０１３５】各方法において、各反応物質のモル比には
特に制限はないが、等モル又はそれに近い比率で反応を
行なうのが有利である。In each method, the molar ratio of the reactants is not particularly limited, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close thereto.
【０１３６】本発明化合物を精製する必要が生じた場合
は、再結晶、カラムクロマトグラフィー、薄層クロマト
グラフィー等の任意の精製方法によって分離、精製する
ことができる。When the compound of the present invention needs to be purified, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography and the like.
【０１３７】本発明化合物を有害生物防除剤として施用
するにあたっては、一般には適当な担体、例えばクレ
ー、タルク、ベントナイト、珪藻土、ホワイトカーボン
等の固体担体あるいは水、アルコール類（イソプロパノ
ール、ブタノール、ベンジルアルコール、フルフリルア
ルコール等）、芳香族炭化水素類（トルエン、キシレン
等）、エーテル類（アニソール等）、ケトン類（シクロ
ヘキサノン、イソホロン等）、エステル類（酢酸ブチル
等）、酸アミド類（Ｎ−メチルピロリドン等）又はハロ
ゲン化炭化水素類（クロルベンゼン等）などの液体担体
と混用して適用することができ、所望により界面活性
剤、乳化剤、分散剤、浸透剤、展着剤、増粘剤、凍結防
止剤、固結防止剤、安定剤などを添加し、液剤、乳剤、
水和剤、ドライフロアブル剤、フロアブル剤、粉剤、粒
剤等任意の剤型にて実用に供することができる。In applying the compound of the present invention as a pest controlling agent, generally, a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth and white carbon, or water, alcohols (isopropanol, butanol, benzyl alcohol) is used. , Furfuryl alcohol etc.), aromatic hydrocarbons (toluene, xylene etc.), ethers (anisole etc.), ketones (cyclohexanone, isophorone etc.), esters (butyl acetate etc.), acid amides (N-methyl) (Pyrrolidone etc.) or halogenated hydrocarbons (chlorobenzene etc.) and the like can be mixed and applied, and if desired, surfactants, emulsifiers, dispersants, penetrants, spreading agents, thickeners, Antifreeze agents, anti-caking agents, stabilizers, etc. are added, and liquid agents, emulsions,
It can be put into practical use in any dosage form such as a wettable powder, a dry flowable agent, a flowable agent, a powder agent, and a granule.
【０１３８】また、本発明化合物は必要に応じて製剤時
又は散布時に他種の除草剤、各種殺虫剤、殺ダニ剤、殺
線虫剤、殺菌剤、植物生長調節剤、共力剤、肥料、土壌
改良剤などと混合施用しても良い。Further, the compound of the present invention may be used as a herbicide of other species, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers during formulation or spraying, if necessary. Alternatively, it may be mixed with a soil conditioner and applied.
【０１３９】特に他の農薬あるいは植物ホルモンと混合
施用することにより、施用薬量の減少による低コスト
化、混合薬剤の相乗作用による殺虫スペクトラムの拡大
や、より高い有害生物防除効果が期待できる。この際、
同時に複数の公知農薬との組み合わせも可能である。本
発明化合物と混合使用する農薬の種類としては、例え
ば、ファーム・ケミカルズ・ハンドブック（ Farm Chem
icals Handbook) １９９４年版に記載されている化合物
などがある。[0139] In particular, when mixed with other pesticides or plant hormones, it can be expected to reduce the cost due to the reduction of the applied dose, to expand the insecticidal spectrum due to the synergistic action of the mixed drugs, and to have a higher pest control effect. On this occasion,
It is also possible to combine a plurality of known pesticides at the same time. Examples of types of pesticides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm Chem
icals Handbook) Compounds described in the 1994 edition.
【０１４０】本発明化合物の施用薬量は適用場面、施用
時期、施用方法、栽培作物等により差異はあるが一般に
は有効成分量としてヘクタール（ha) 当たり０．００５
〜５０ｋｇ程度が適当である。The application amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but generally it is 0.005 per hectare (ha) as an active ingredient amount.
Approximately 50 kg is suitable.
【０１４１】次に具体的に本発明化合物を用いる場合の
製剤の配合例を示す。但し本発明の配合例は、これらの
みに限定されるものではない。なお、以下の配合例にお
いて「部」は重量部を意味する。Next, formulation examples of preparations using the compound of the present invention will be specifically shown. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight.
【０１４２】〔水和剤〕 本発明化合物・・・・・・・ ５〜８０部 固体担体 ・・・・・・・１０〜８５部 界面活性剤 ・・・・・・・ １〜１０部 その他 ・・・・・・・ １〜５ 部 その他として、例えば固結防止剤などがあげられる。[Wettable powder] Compound of the present invention: 5 to 80 parts Solid carrier: 10 to 85 parts Surfactant: 1-10 parts Others ・ ・ ・ ・ ・ ・ ・ ・ 1 to 5 parts Other examples include anti-caking agents.
【０１４３】〔乳 剤〕 本発明化合物・・・・・・・ １〜３０部 液体担体 ・・・・・・・３０〜９５部 界面活性剤 ・・・・・・・ ５〜１５部[Emulsion] Compound of the present invention: 1 to 30 parts Liquid carrier: 30 to 95 parts Surfactant: 5 to 15 parts
【０１４４】〔フロアブル剤〕
本発明化合物・・・・・・・ ５〜７０部
液体担体 ・・・・・・・１５〜６５部
界面活性剤 ・・・・・・・ ５〜１２部
その他 ・・・・・・・ ５〜３０部
その他として、例えば凍結防止剤、増粘剤等があげられ
る。[Flowable Agent] Compound of the present invention: 5 to 70 parts Liquid carrier: 15 to 65 parts Surfactant: 5 to 12 parts Others: ........... Other examples of 5 to 30 parts include antifreezing agents, thickeners and the like.
【０１４５】〔粒状水和剤（ドライフロアブル剤）〕 本発明化合物・・・・・・・２０〜９０部 固体担体 ・・・・・・・１０〜６０部 界面活性剤 ・・・・・・・ １〜２０部[Granular wettable powder (dry flowable agent)] Compound of the present invention: 20 to 90 parts Solid carrier: 10 to 60 parts Surfactant: 1-20 parts
【０１４６】〔粒 剤〕 本発明化合物・・・・・・・0.1 〜１０部 固体担体 ・・・・・・・90〜99.99 部 その他 ・・・・・・・ １〜５ 部[Granule] Compound of the present invention: 0.1 to 10 parts Solid carrier: 90-99.99 parts Others ・ ・ ・ ・ ・ ・ ・ ・ 1 to 5 parts
【０１４７】〔粉 剤〕 本発明化合物・・・・・・・0.01〜３０部 固体担体 ・・・・・・・67〜99.5 部 その他 ・・・・・・・ ０〜３ 部[Powder] The compound of the present invention: 0.01 to 30 parts Solid carrier: 67-99.5 parts Other: 0 to 3 parts
【０１４８】[0148]
実施例（合成例、製剤例、試験例）
以下、本発明について実施例（合成例、製剤例、試験
例）を挙げて具体的に詳述する。Examples (Synthesis Examples, Formulation Examples, Test Examples) The present invention will be specifically described below with reference to Examples (Synthesis Examples, Formulation Examples, Test Examples).
【０１４９】〔合成例〕本発明に包含される化合物は、
以下に示した合成例に基づき製造した又は製造すること
ができるが、本発明はこれらの化合物にのみ限定される
ものではない。[Synthesis Example] The compounds included in the present invention are
Although it can be produced or can be produced based on the synthetic examples shown below, the present invention is not limited to these compounds.
【０１５０】合成例１
２−（１−フェニル−２−フェニルカルボニルアミノエ
タン−１−イリデン）−Ｎ−（４−トリフルオロメトキ
シフェニル）ヒドラジンカルボキサミド
（本発明化合物Ｎｏ．１）１−フェニル−２−フェニル
カルボニルアミノエタン−１−オン２．３０ｇをエタノ
ール２０ｍｌに溶解し、室温で撹拌下、ヒドラジン水和
物５ｍｌを滴下し、さらに還流下で３時間撹拌した。減
圧下で溶媒を留去し、クロロホルム１００ｍｌを加えて
溶解した後、１規定塩酸および飽和食塩水で洗浄し、さ
らに無水硫酸ナトリウムで乾燥後、減圧下で溶媒を留去
して、１−フェニル−２−フェニルカルボアミノエタン
−１−イリデンヒドラジドを２．４０ｇ得た。Synthesis Example 1 2- (1-Phenyl-2-phenylcarbonylaminoethane-1-ylidene) -N- (4-trifluoromethoxyphenyl) hydrazinecarboxamide (Compound No. 1 of the present invention) 1-phenyl-2 2.30 g of -phenylcarbonylaminoethane-1-one was dissolved in 20 ml of ethanol, 5 ml of hydrazine hydrate was added dropwise with stirring at room temperature, and the mixture was further stirred under reflux for 3 hours. The solvent was distilled off under reduced pressure, 100 ml of chloroform was added and dissolved, then washed with 1N hydrochloric acid and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 1-phenyl. 2.40 g of 2-phenylcarboaminoethane-1-ylidene hydrazide was obtained.
【０１５１】１−フェニル−２−フェニルカルボアミノ
エタン−１−イリデンヒドラジド１．００ｇをジクロロ
メタン２０ｍｌに溶解し、室温で撹拌下、４−トリフル
オロメトキシフェニルイソシアネート０．７０ｇを滴下
後、さらに室温で８時間撹拌した。減圧下で溶媒を留去
後、残留物をイソプロピルエーテルとイソプロパノール
の混合溶媒を用いて再結晶化し目的物を０．３７ｇ得
た。1
HNMR(CDCl3+DMSO d-6, TMS, δppm): 4.50(2H, d, J=
6.0Hz), 7.00-8.10(14H,m), 8.87(1H, s), 9.08(1H, b
s), 10.52(1H, s).1-Phenyl-2-phenylcarboaminoethane-1-ylidenehydrazide (1.00 g) was dissolved in dichloromethane (20 ml), and 4-trifluoromethoxyphenylisocyanate (0.70 g) was added dropwise with stirring at room temperature. It was stirred for 8 hours. After evaporating the solvent under reduced pressure, the residue was recrystallized using a mixed solvent of isopropyl ether and isopropanol to obtain 0.37 g of the desired product. 1 HNMR (CDCl 3 + DMSO d-6, TMS, δppm): 4.50 (2H, d, J =
6.0Hz), 7.00-8.10 (14H, m), 8.87 (1H, s), 9.08 (1H, b
s), 10.52 (1H, s).
【０１５２】合成例２
２−［１−（３−クロロフェニル）−２−（３−クロロ
フェニル）カルボニルアミノエタン−１−イリデン）−
Ｎ−（４−トリフルオロメトキシ）ヒドラジンカルボキ
サミド
（本発明化合物Ｎｏ．１８）１−（３−クロロフェニ
ル）−２−（３−クロロフェニル）カルボニルアミノエ
タン−１−オン０．６２ｇ及びＮ−（４−トリフルオロ
メトキシ）ヒドラジンカルボキサミド０．４７ｇをエタ
ノール２０ｍｌに加え、室温で撹拌下、濃塩酸を０．１
ｍｌ滴下した。還流下で３時間撹拌後、冷却し、析出し
た結晶をろ過して集めた。さらに、この結晶を冷やした
エタノールで洗浄後、乾燥して目的化合物を０．５３ｇ
得た。Synthesis Example 2 2- [1- (3-chlorophenyl) -2- (3-chlorophenyl) carbonylaminoethane-1-ylidene)-
N- (4-trifluoromethoxy) hydrazinecarboxamide (inventive compound No. 18) 1- (3-chlorophenyl) -2- (3-chlorophenyl) carbonylaminoethan-1-one 0.62 g and N- (4- (Trifluoromethoxy) hydrazinecarboxamide (0.47 g) was added to ethanol (20 ml), and concentrated hydrochloric acid (0.1 ml) was added under stirring at room temperature.
ml was added dropwise. After stirring under reflux for 3 hours, the mixture was cooled, and the precipitated crystals were collected by filtration. Further, the crystals were washed with cold ethanol and dried to give 0.53 g of the desired compound.
Obtained.
【０１５３】融点：２１３．０−２１４．５℃1
HNMR(CDCl3+DMSO d-6, TMS, δppm): 4.50(2H, d, J=
6.0Hz), 7.00-8.20(12H,m), 8.95(1H, bs), 9.20(1H,
t, J=6.0Hz), 10.50(1H, bs).Melting point: 213.0-214.5 ° C. 1 HNMR (CDCl 3 + DMSO d-6, TMS, δppm): 4.50 (2H, d, J =
6.0Hz), 7.00-8.20 (12H, m), 8.95 (1H, bs), 9.20 (1H,
t, J = 6.0Hz), 10.50 (1H, bs).
【０１５４】参考例１Reference Example 1
【０１５５】１−フェニル−２−フェニルカルボアミノ
エタン−１−オン
ベンゾイルクロライド２．１ｇをピリジン２０ｍｌに溶
かし、室温で撹拌下、１−フェニル−２−アミノエタン
−１−オン（フェナシルアミン）の塩酸塩５．０ｇを添
加した後、還流下で２０分間撹拌した。冷却後、氷水２
００ｍｌに加え、析出した結晶をろ過して集めた。この
結晶を乾燥後、イソプロパノールを用いて再結晶化し、
１−フェニル−２−フェニルカルボニルアミノエタン−
１−オンを２．４５ｇ得た。1
HNMR(CDCl3, TMS, δ ppm): 4.80(2H, d, J=5.0Hz),
7.20-8.15(11H, m).2.1 g of 1-phenyl-2-phenylcarboaminoethane-1-one benzoyl chloride was dissolved in 20 ml of pyridine, and 1-phenyl-2-aminoethan-1-one (phenacylamine) was added to the solution under stirring at room temperature. After adding 5.0 g of hydrochloride, the mixture was stirred under reflux for 20 minutes. After cooling, ice water 2
In addition to 00 ml, the precipitated crystals were collected by filtration. After drying the crystals, it was recrystallized using isopropanol,
1-phenyl-2-phenylcarbonylaminoethane-
2.45 g of 1-one was obtained. 1 HNMR (CDCl 3 , TMS, δ ppm): 4.80 (2H, d, J = 5.0Hz),
7.20-8.15 (11H, m).
【０１５６】上記合成例に従って第２表に示す化合物を
合成した。The compounds shown in Table 2 were synthesized according to the above synthesis examples.
【０１５７】第 ２ 表Table 2
【０１５８】[0158]
【化１１】 [Chemical 11]
【０１５９】[0159]
【表７７】 ─────────────────────────────────── No. R1 R2 R3 R4 W Xl Ym Zn 融点 ─────────────────────────────────── 1 H H H H O H H 4-OCF3 199.0-204.0 2 H H H H O H H 4-CF3 224.0-227.0 3 H H H H O H H 4-OCF2CHF2 214.5-217.0 4 H H H H O H 4-F 4-OCF3 221.0-223.0 5 H H H H O H 4-Cl 4-OCF3 229.0-231.0 6 H H H H O 3-F H 4-OCF3 225.0-227.0 7 H H H H O 3-F 4-F 4-OCF3 227.0-228.5 8 H H H H O 3-F 2-Cl 4-OCF3 215.0-216.5 9 H H H H O 3-F 3-Cl 4-OCF3 217.0-219.0 10 H H H H O 3-F 4-Cl 4-OCF3 232.0-234.0 11 H H H H O 4-F 4-F 4-OCF3 214.0-215.5 12 H H H H O 3-Cl 4-F 4-OCF3 211.5-213.5 13 H H H H O 4-Cl 4-F 4-OCF3 219.5-221.5 14 H H H H O H 3-CF3 4-OCF3 205.0-207.5 15 H H H H O H 3,5-Cl2 4-OCF3 222.0-224.0 16 H H H H O H 3-Cl 4-OCF3 205.0-207.0 17 H H H H O 4-Cl 3-Cl 4-OCF3 202.0-206.0 18 H H H H O 3-Cl 3-Cl 4-OCF3 213.0-214.5 19 H H H H O H 2-F 4-OCF3 192.5-194.5 20 H H H H O H 3-F 4-OCF3 211.0-212.5 21 H H H H O H 3-Br 4-OCF3 212.0-213.5 22 H H H H O H 3-CH3 4-OCF3 217.0-219.0 23 H H H H O 3-F 3-NO2 4-OCF3 214.5-217.0 ───────────────────────────────────[Table 77] ─────────────────────────────────── No. R 1 R 2 R 3 R 4 WX l Y m Z n Melting point ─────────────────────────────────── 1 HHHHOHH 4-OCF 3 199.0-204.0 2 HHHHOHH 4-CF 3 224.0-227.0 3 HHHHOHH 4-OCF 2 CHF 2 214.5-217.0 4 HHHHOH 4-F 4-OCF 3 221.0-223.0 5 HHHHOH 4-Cl 4-OCF 3 229.0-231.0 6 HHHHO 3-FH 4 -OCF 3 225.0-227.0 7 HHHHO 3-F 4-F 4-OCF 3 227.0-228.5 8 HHHHO 3-F 2-Cl 4-OCF 3 215.0-216.5 9 HHHHO 3-F 3-Cl 4-OCF 3 217.0- 219.0 10 HHHHO 3-F 4-Cl 4-OCF 3 232.0-234.0 11 HHHHO 4-F 4-F 4-OCF 3 214.0-215.5 12 HHHHO 3-Cl 4-F 4-OCF 3 211.5-213.5 13 HHHHO 4- Cl 4-F 4-OCF 3 219.5-221.5 14 HHHHOH 3-CF 3 4-OCF 3 205.0-207.5 15 HHHHOH 3,5-Cl 2 4-OCF 3 222.0-224.0 16 HHHHOH 3-Cl 4-OCF 3 205.0- 207.0 17 HHHHO 4-Cl 3-Cl 4-OCF 3 202.0-206.0 18 HHHHO 3-Cl 3-Cl 4-OCF 3 213.0-214.5 19 HHHHOH 2-F 4-OCF 3 192.5-194.5 20 HHHHOH 3-F 4- OCF 3 211.0-212.5 21 HHHHOH 3-Br 4-OCF 3 212.0-213.5 22 HHHHOH 3-CH 3 4-OCF 3 217.0-219.0 23 HHHHO 3-F 3-NO 2 4-OCF 3 214.5-217.0 ───────────────── ──────────────────
【０１６０】[0160]
【表７８】 ─────────────────────────────────── No. R1 R2 R3 R4 W Xl Ym Zn 融点 ─────────────────────────────────── 24 H H H H O 3-F 2,6-F2 4-OCF3 218.5-221.5 25 H H H H O 3-F 3-CN 4-OCF3 219.5-221.5 26 H H H H O 4-NO2 3-Cl 4-OCF3 213.5-215.0 27 H H H H O H 3-CF3 4-CF3 219.0-221.0 28 H H H H O 3-Cl 3-Cl 4-CF3 202.0-203.5 29 H H H H O 4-F 3-Cl 4-OCF3 190.0-196.0 30 H H H H O 3-Cl 3-CF3 4-OCF3 182.0-183.0 31 H H H H O 3-Br 3-Cl 4-OCF3 213.0-215.5 32 H H H H O 3-Br H 4-OCF3 209.0-211.0 33 H H H H O 4-Br H 4-OCF3 227.0-229.0 34 H H H H O 4-OCH3 H 4-OCF3 218.5-220.5 35 H H H H O H 2,3-F2 4-OCF3 189.0-190.5 36 H H H H O H 2,4-F2 4-OCF3 197.5-199.0 37 H H H H O H 2,5-F2 4-OCF3 198.5-200.5 38 H H H H O H 3,4-F2 4-OCF3 213.0-214.0 39 H H H H O H 3,5-F2 4-OCF3 208.0-210.5 40 H H H H O 3-F 3,5-F2 4-OCF3 197.5-200.0 41 H H H H O 3-F 3,5-F2 4-OCF2Br 183.0-185.0 42 H H H H O 3-F 3,5-F2 4-Cl 207.5-209.0 43 H H H H O 3-F 3-CF3 4-OCF3 203.0-204.0 44 H H H H O 3-F 3-CF3 4-OCF2CHF2 208.5-210.0 45 H H H H O 3-F 3-CF3 4-Br 208.0-210.0 46 H H H H O 3-CF3 3-Cl 4-OCF3 198.0-201.0 ───────────────────────────────────[Table 78] ─────────────────────────────────── No. R 1 R 2 R 3 R 4 WX l Y m Z n Melting point ─────────────────────────────────── 24 HHHHO 3-F 2,6- F 2 4-OCF 3 218.5-221.5 25 HHHHO 3-F 3-CN 4-OCF 3 219.5-221.5 26 HHHHO 4-NO 2 3-Cl 4-OCF 3 213.5-215.0 27 HHHHOH 3-CF 3 4-CF 3 219.0-221.0 28 HHHHO 3-Cl 3-Cl 4-CF 3 202.0-203.5 29 HHHHO 4-F 3-Cl 4-OCF 3 190.0-196.0 30 HHHHO 3-Cl 3-CF 3 4-OCF 3 182.0-183.0 31 HHHHO 3-Br 3-Cl 4-OCF 3 213.0-215.5 32 HHHHO 3-Br H 4-OCF 3 209.0-211.0 33 HHHHO 4-Br H 4-OCF 3 227.0-229.0 34 HHHHO 4-OCH 3 H 4-OCF 3 218.5-220.5 35 HHHHOH 2,3-F 2 4-OCF 3 189.0-190.5 36 HHHHOH 2,4-F 2 4-OCF 3 197.5-199.0 37 HHHHOH 2,5-F 2 4-OCF 3 198.5-200.5 38 HHHHOH 3,4-F 2 4-OCF 3 213.0-214.0 39 HHHHOH 3,5-F 2 4-OCF 3 208.0-210.5 40 HHHHO 3-F 3,5-F 2 4-OCF 3 197.5-200.0 41 HHHHO 3 -F 3,5-F 2 4-OCF 2 Br 183.0-185.0 42 HHHHO 3-F 3,5-F 2 4-Cl 207.5-209 .0 43 HHHHO 3-F 3-CF 3 4-OCF 3 203.0-204.0 44 HHHHO 3-F 3-CF 3 4-OCF 2 CHF 2 208.5-210.0 45 HHHHO 3-F 3-CF 3 4-Br 208.0- 210.0 46 HHHHO 3-CF 3 3-Cl 4-OCF 3 198.0-201.0 ────────────────────────────────── ──
【０１６１】[0161]
【表７９】 ─────────────────────────────────── No. R1 R2 R3 R4 W Xl Ym Zn 融点 ─────────────────────────────────── 47 H H H H O H 3,5-F2 2,6-Cl2 226.0-218.5 48 H H H H O 3-Br 3-Cl 4-CF3 203.0-204.5 49 H H H H O 3-Br 3-Cl 4-OCF2Br 195.0-197.0 50 H H H H O 3-CF3 3-Cl 4-CF3 205.0-206.0 51 H H H H O 3-F 3-Cl 4-CF3 213.5-215.5 52 H H H H O 3-F 4-F 4-CF3 222.0-224.5 53 H H H H O 3-F 3,5-F2 4-CF3 211.5-213.0 54 H H H H O 3-F 2,5-F2 4-CF3 213.5-216.0 55 H H H H O 3-CN H 4-OCF3 232.0-234.0 56 H H H H O 3-Cl 3-F 4-OCF3 213.0-214.5 57 H H H H O 3-Cl 3-F 4-CF3 217.0-218.5 58 H H H H O 3-Cl 3-Br 4-CF3 209.0-210.0 59 H H H H O 3-Cl 3-CF3 4-CF3 212.0-213.5 60 H H H H O 3-Cl 3,5-Cl2 4-CF3 218.0-223.0 61 H H H H O 4-Cl 3-Cl 4-CF3 219.5-221.5 62 H H H H O 3-F 3-F 4-OCF3 204.0-206.0 63 H H H H O 3-CF3 3-F 4-OCF3 192.0-193.0 ───────────────────────────────────[Table 79] ─────────────────────────────────── No. R 1 R 2 R 3 R 4 WX l Y m Z n Melting point ─────────────────────────────────── 47 HHHHOH 3,5-F 2 2 , 6-Cl 2 226.0-218.5 48 HHHHO 3-Br 3-Cl 4-CF 3 203.0-204.5 49 HHHHO 3-Br 3-Cl 4-OCF 2 Br 195.0-197.0 50 HHHHO 3-CF 3 3-Cl 4- CF 3 205.0-206.0 51 HHHHO 3-F 3-Cl 4-CF 3 213.5-215.5 52 HHHHO 3-F 4-F 4-CF 3 222.0-224.5 53 HHHHO 3-F 3,5-F 2 4-CF 3 211.5-213.0 54 HHHHO 3-F 2,5-F 2 4-CF 3 213.5-216.0 55 HHHHO 3-CN H 4-OCF 3 232.0-234.0 56 HHHHO 3-Cl 3-F 4-OCF 3 213.0-214.5 57 HHHHO 3-Cl 3-F 4-CF 3 217.0-218.5 58 HHHHO 3-Cl 3-Br 4-CF 3 209.0-210.0 59 HHHHO 3-Cl 3-CF 3 4-CF 3 212.0-213.5 60 HHHHO 3-Cl 3,5-Cl 2 4-CF 3 218.0-223.0 61 HHHHO 4-Cl 3-Cl 4-CF 3 219.5-221.5 62 HHHHO 3-F 3-F 4-OCF 3 204.0-206.0 63 HHHHO 3-CF 3 3 -F 4-OCF 3 192.0-193.0 ────────────────────────── ──────────
【０１６２】〔製剤例〕次に、本発明化合物を有効成分
とする有害生物防除剤の製剤例を示すが、本発明はこれ
らに限定されるものではない。尚、以下の製剤例におい
て、「部」は重量部を意味する。Formulation Examples Next, formulation examples of pest control agents containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited thereto. In the following formulation examples, "part" means part by weight.
【０１６３】〔製剤例１〕水和剤 本発明化合物 ・・・・・・・・・５０部 ジークライトＰＦＰ ・・・・・・・・・４３部 （カオリン系クレー：ジークライト工業（株）商品名） ソルポール 5050 ・・・・・・・・・ ２部 （アニオン性界面活性剤：東邦化学工業（株）商品名） ルノックス 1000 Ｃ ・・・・・・・・・ ３部 （アニオン性界面活性剤：東邦化学工業（株）商品名） カープレックス＃８０（固結防止剤）・・・ ２部 （ホワイトカーボン：塩野義製薬（株）商品名） 以上を均一に混合粉砕して水和剤とする。[Formulation Example 1] Wettable powder Compound of the present invention: 50 parts Sieglite PFP ・ ・ ・ ・ ・ ・ 43 copies (Kaolin clay: product name of Siglite Industrial Co., Ltd.) Solpol 5050 ・ ・ ・ ・ ・ ・ ・ Part 2 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Lunox 1000 C ・ ・ ・ ・ ・ ・ ・ 3 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex # 80 (anti-caking agent) ... 2 parts (White carbon: Shionogi Pharmaceutical Co., Ltd. product name) The above is uniformly mixed and pulverized to obtain a wettable powder.
【０１６４】〔製剤例２〕乳 剤
本発明化合物 ・・・・・・・・・ ３部
キシレン ・・・・・・・・・７６部
イソホロン ・・・・・・・・・１５部
ソルポール3005Ｘ ・・・・・・・・・ ６部
（非イオン性界面活性剤とアニオン性界面活性剤との混
合物：東邦化学工業（株）商品名）
以上を均一に混合して乳剤とする。[Formulation Example 2] Emulsion Compound of the present invention: 3 parts xylene: 76 parts Isophorone: 15 parts Solpol 3005X ..... 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above components are uniformly mixed to form an emulsion.
【０１６５】〔製剤例３〕フロアブル剤 本発明化合物 ・・・・・・・・・３５部 アグリゾールＳ−711 ・・・・・・・・・ ８部 （非イオン性界面活性剤：花王（株）商品名） ルノックス 1000 Ｃ ・・・・・・・・・ 0.5部 （アニオン性界面活性剤：東邦化学工業（株）商品名） １％ロドポール水 ・・・・・・・・・２０部 （増粘剤：ローン・プーラン社商品名） エチレングリコール（凍結防止剤）・・・・ ８部 水 ・・・・・・・・・28.5部 以上を均一に混合して、フロアブル剤とする。[Formulation Example 3] Flowable agent Compound of the present invention: 35 parts Agrisol S-711 ・ ・ ・ ・ ・ ・ ・ 8 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000 C ... 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) 1% Rhodopol water: 20 copies (Thickener: Loan Poulin's trade name) Ethylene glycol (antifreeze) ... 8 parts Water: 28.5 copies The above is uniformly mixed to obtain a flowable agent.
【０１６６】〔製剤例４〕粒状水和剤（ドライフロアブ
ル剤）
本発明化合物 ・・・・・・・・・７５部
イソバンNo.1 ・・・・・・・・・１０部
（アニオン性界面活性剤：クラレイソプレンケミカル
（株）商品名）
バニレックスＮ ・・・・・・・・・ ５部
（アニオン性界面活性剤：山陽国策パルプ（株）商品
名）
カープレックス＃８０ ・・・・・・・・・１０部
（ホワイトカーボン：塩野義製薬（株）商品名）
以上を均一に混合微粉砕してドライフロアブル剤とす
る。[Formulation Example 4] Granular wettable powder (dry flowable agent) Compound of the present invention: 75 parts Isoban No. 1: 10 parts (anionic interface Activator: Trade name of Kuraray Isoprene Chemical Co., Ltd. Vanillex N ..... 5 parts (Anionic surfactant: Trade name of Sanyo Kokusaku Pulp Co., Ltd.) Carplex # 80 .... 10 parts (white carbon: Shionogi Seiyaku Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a dry flowable agent.
【０１６７】〔製剤例５〕粒 剤
本発明化合物 ・・・・・・・・０．１部
ベントナイト ・・・・・・・５５．０部
タルク ・・・・・・・４４．９部
以上を均一に混合粉砕した後、少量の水を加えて攪拌混
合捏和し、押出式造粒機で造粒し、乾燥して粒剤にす
る。[Formulation Example 5] Granules Compound of the present invention: 0.1 part bentonite: 55.0 parts talc: 44.9 parts or more After being uniformly mixed and pulverized, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.
【０１６８】〔製剤例６〕粉 剤 本発明化合物 ・・・・・・・・３．０部 カープレックス＃８０ ・・・・・・・・０．５部 （ホワイトカーボン：塩野義製薬（株）商品名） クレー ・・・・・・・・ ９５部 リン酸ジイソプロピル ・・・・・・・・１．５部 以上を均一に混合粉砕して粉剤とする。[Formulation Example 6] Powder Compound of the present invention: 3.0 parts Carplex # 80: 0.5 copy (White carbon: Shionogi Pharmaceutical Co., Ltd. product name) Clay ・ ・ ・ ・ ・ ・ 95 copies Diisopropyl phosphate: 1.5 parts The above is uniformly mixed and pulverized to obtain a powder.
【０１６９】使用に際しては上記水和剤、乳剤、フロア
ブル剤、粒状水和剤は水で５０〜２００００倍に希釈し
て有効成分が１ヘクタール（ha) 当たり０．００５〜５
０ｋｇになるように散布する。In use, the wettable powders, emulsions, flowables and granular wettable powders are diluted 50 to 20000 times with water to prepare active ingredient in an amount of 0.005 to 5 per hectare (ha).
Sprinkle so that it weighs 0 kg.
【０１７０】〔試験例〕次に、本発明化合物の有害生物
防除剤としての有用性について、以下の試験例において
具体的に説明する。TEST EXAMPLE Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples.
【０１７１】試験例１ ハスモンヨトウに対する殺虫試
験
明細書に記載された本発明化合物の５％乳剤（化合物に
よっては25％水和剤を供試）を展着剤の入った水で希釈
して、1000ppm濃度の薬液に調製し、この薬液中にカン
ランの葉を約10秒間浸漬し、風乾後シャーレに入れ、こ
の中にハスモンヨトウ２令幼虫をシャーレ当たり10頭を
放虫し、孔のあいた蓋をして25℃恒温室に収容し、６日
間経過後の死虫率を下記の計算式から求めた。尚、試験
は２区制で行なった。Test Example 1 Insecticidal test against Spodoptera litura A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent to give 1000 ppm. Prepare a chemical solution of the concentration, immerse kanran leaves in this chemical solution for about 10 seconds, air-dry and put it in a petri dish, in which 10 second-infested larvae of Spodoptera litura are released per petri dish with a perforated lid. And stored in a constant temperature chamber at 25 ° C, and the mortality rate after 6 days was calculated from the following formula. The test was conducted in a two-division system.
【０１７２】 死虫率（％）＝ (死虫数／放虫数）×１００[0172] Mortality rate (%) = (Number of dead insects / Number of released insects) x 100
【０１７３】その結果、以下の化合物が１００％の死虫
率を示した。
本発明化合物：Ｎｏ．１，２，３，４，６，７，８，
９，１１，１２，１３，１４，１５，１６，１７，１
８，１９，２０，２１，２２，２７，２８，２９，３
０，３１，３２，３３，３６，３７，３８，３９，４
０，４１，４３，４６，４８，４９，５０，５１，５
２，５３，５６，５７，５８，６２，６３．As a result, the following compounds showed 100% mortality. Inventive compound: No. 1, 2, 3, 4, 6, 7, 8,
9, 11, 12, 13, 14, 15, 16, 17, 1
8, 19, 20, 21, 22, 27, 28, 29, 3
0, 31, 32, 33, 36, 37, 38, 39, 4
0, 41, 43, 46, 48, 49, 50, 51, 5
2,53,56,57,58,62,63.
【０１７４】試験例２ ニジュウヤホシテントウに対す
る殺虫試験
明細書に記載された本発明化合物の５％乳剤（化合物に
よっては25％水和剤を供試）を展着剤の入った水で希釈
して、1000ppm濃度の薬液に調製し、この薬液中にトマ
トの葉を約10秒間浸漬し、風乾後シャーレに入れ、この
中にニジュウヤホシテントウ２令幼虫をシャーレ当たり
10頭を放虫し、蓋をして25℃恒温室に収容し、６日間経
過後の死虫率を下記の計算式から求めた。尚、試験は２
区制で行なった。Test Example 2 Insecticidal test against pearl oyster lady beetle A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent. Then, prepare a chemical solution with a concentration of 1000 ppm, soak the tomato leaves in this chemical solution for about 10 seconds, air-dry and place in a petri dish.
Ten of the insects were released, covered and placed in a thermostatic chamber at 25 ° C, and the mortality rate after 6 days was calculated from the following formula. The test is 2
It was done in a ward system.
【０１７５】 死虫率（％）＝ (死虫数／放虫数）×１００[0175] Mortality rate (%) = (Number of dead insects / Number of released insects) x 100
【０１７６】その結果、以下の化合物が１００％の死虫
率を示した。
本発明化合物：Ｎｏ．１，２，３，４，６，７，８，
９，１０，１１，１２，１３，１４，１５，１６，１
７，１８，１９，２０，２１，２２，２３，２４，２
５，２７，２８，２９，３０，３１，３２，３３，３
６，３７，３８，３９，４０，４１，４３，４５，４
６，４８，４９，５０，５１，５２，５３，５６，５
７，５８，５９，６２，６３．As a result, the following compounds showed 100% mortality. Inventive compound: No. 1, 2, 3, 4, 6, 7, 8,
9, 10, 11, 12, 13, 14, 15, 16, 1
7, 18, 19, 20, 21, 22, 23, 24, 2
5,27,28,29,30,31,32,33,3
6,37,38,39,40,41,43,45,4
6,48,49,50,51,52,53,56,5
7, 58, 59, 62, 63.
【０１７７】試験例３ キュウリうどんこ病防除効果試
験
直径７ｃｍのポットで育成した１．５葉期のキュウリ
（品種：相模半白）に、本発明化合物乳剤を水で希釈し
て５００ｐｐｍに調製した薬液を、スプレーガンを用い
ポット当たり２０ｍｌ散布した。散布翌日キュウリうど
んこ病菌（Ｓｐｈａｅｒｏｔｈｅｃａ ｆｕｌｉｇｉｎ
ｅａ）の胞子懸濁液（３×１０5個／ｍｌ）を噴霧し、
接種した。その後、温室におき、接種１０日後に形成さ
れた病班面積の接種葉に占める割合を測定し、下記の式
に従い、防除価を算出した。
防除価＝［１−（処理区病班面積率／無処理区病班面積
率）］×１００Test Example 3 Cucumber Powdery Mildew Control Effect Test A 1.5 leaf stage cucumber (cultivar: Sagamihanjiro) grown in a pot with a diameter of 7 cm was diluted with water to prepare a compound of the present invention at 500 ppm. 20 ml of the chemical solution was sprayed per pot using a spray gun. The day after spraying, cucumber powdery mildew (Sphaerotheca fuligin)
spray a spore suspension of ea) (3 × 10 5 cells / ml),
I inoculated. Then, it was placed in a greenhouse and the ratio of the diseased area formed 10 days after inoculation to the inoculated leaves was measured, and the control value was calculated according to the following formula. Control value = [1- (treatment area area ratio / non-treatment area area ratio)] × 100
【０１７８】その結果、以下の化合物が防除価１００を
示した。
本発明化合物：Ｎｏ．９，１８，２８，３１．As a result, the following compounds showed a control value of 100. Inventive compound: No. 9, 18, 28, 31.
【０１７９】[0179]
【発明の効果】本発明化合物は多くの農業害虫、ハダニ
類に対して優れた殺虫・殺ダニ活性を有し、かつ多くの
植物病害に対して優れた殺菌活性を有す。一方、ホ乳
類、魚類及び益虫に対してはほとんど悪影響を及ぼさな
い。従って、本発明化合物は、有用な有害生物防除剤を
提供することができる。INDUSTRIAL APPLICABILITY The compound of the present invention has excellent insecticidal and acaricidal activity against many agricultural pests and mites, and also has excellent bactericidal activity against many plant diseases. On the other hand, it has almost no adverse effect on mammals, fish and beneficial insects. Therefore, the compound of the present invention can provide a useful pest control agent.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ０７Ｃ 311/08 Ｃ０７Ｃ 311/08 311/37 311/37 311/47 311/47 317/42 317/42 317/44 317/44 323/31 323/31 323/44 323/44 323/62 323/62 325/02 325/02 331/12 331/12 335/16 335/16 337/08 337/08 Ｃ０７Ｆ 7/10 Ｃ０７Ｆ 7/10 Ａ (72)発明者 三宅 敏郎 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社 生物科学研究所内 (72)発明者 藤田 明彦 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社 生物科学研究所内 (72)発明者 三森 紀彦 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社 生物科学研究所内 (72)発明者 大宅 博司 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社 生物科学研究所内 (72)発明者 古里 孝 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社 生物科学研究所内 (56)参考文献 特開 平５−17428（ＪＰ，Ａ) 特表 平６−502414（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 281/14 A01N 47/34 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 7 Identification code FI C07C 311/08 C07C 311/08 311/37 311/37 311/47 311/47 317/42 317/42 317/44 317/44 323/31 323/31 323/44 323/44 323/62 323/62 325/02 325/02 331/12 331/12 335/16 335/16 337/08 337/08 C07F 7/10 C07F 7/10 A (72) Inventor Toshiro Miyake 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama NISSAN CHEMICAL INDUSTRIES CO., LTD., Institute of Biological Sciences (72) Inventor Akihiko Fujita 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama NISSAN CHEMICAL INDUSTRIES, INC. Inside the Institute for Science (72) Inventor Norihiko Mimori 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama NISSAN CHEMICAL INDUSTRIAL CO., LTD.Institute for Biological Sciences (72) Hiroshi Oyaku 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama 1470 NISSAN CHEMICAL INDUSTRIES CO., LTD. Company Institute of Biological Sciences (72) Inventor Ko Takashi 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama Prefecture, Institute of Biological Science, Nissan Chemical Industries, Ltd. (56) Reference JP-A-5-17428 (JP, A) JP-A-6-502414 (JP, A) (58) Fields surveyed (Int.Cl. 7 , DB name) C07C 281/14 A01N 47/34 CA (STN) REGISTRY (STN)
Claims (6)
ノ基、ニトロ基、ＳＣＮ基、トリメチルシリル基、
Ｒ9 、ＯＲ9、Ｓ（Ｏ）pＲ9基、ＯＳ（Ｏ）2Ｒ9基、Ｏ
Ｃ（Ｏ）Ｒ9基、Ｃ（Ｏ）Ｒ9基、ＣＯ2Ｒ9基、Ｃ（Ｏ）
Ｎ（Ｒ9）Ｒ10基、ＳＯ2Ｎ（Ｒ9）Ｒ10基、ＮＨＣ
（Ｏ）Ｒ9基、Ｎ（Ｒ9）Ｒ10基、隣あった炭素原子間で
形成する−ＣＨ＝ＣＨ−ＣＨ＝ＣＨ−基、−ＯＣＨ2Ｏ
−基、−ＯＣＨ2ＣＨ2Ｏ−基、−ＯＣＦ2Ｏ−基、−Ｏ
ＣＦ2ＣＦ2Ｏ−基又は−ＯＣＦ2ＣＦ2−基を示し、 Ｒ1は水素原子、Ｒ5、Ｒ5によって置換されていてもよ
いＣ1〜Ｃ6アルキル基又は（Ｒ5）qによって置換されて
いてもよいフェニル基を示し、 Ｒ2、Ｒ3、Ｒ4は各々独立して水素原子、Ｃ1〜Ｃ6アル
キル基、Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ6アルキニル
基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ2〜Ｃ6アルコキシアル
キル基、Ｃ2〜Ｃ6アルキルカルボニル基、Ｃ2〜Ｃ6アル
コキシカルボニル基、Ｃ2〜Ｃ6ハロアルキルカルボニル
基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキルチ
オ基、Ｒ6ＯＣ（Ｏ）Ｎ（Ｒ7）Ｓ−基、Ｒ7（Ｒ8）ＮＳ
−基又は（Ｒ5）qによって置換されていてもよいベンジ
ル基を示し、 Ｒ5はハロゲン原子、水酸基、シアノ基、ニトロ基、Ｃ1
〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6
アルコキシ基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6ア
ルキルチオ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1〜Ｃ6
アルキルスルホニル基、Ｃ1〜Ｃ6ハロアルキルスルホニ
ル基、Ｃ2〜Ｃ6アルコキシカルボニル基、アミノ基又は
ジＣ1〜Ｃ6アルキルアミノ基を示し、 Ｒ6、Ｒ7、Ｒ8は各々独立してＣ1〜Ｃ6アルキル基、
（Ｒ5）qによって置換されていてもよいフェニル基又は
（Ｒ5）qによって置換されていてもよいベンジル基を示
し、 Ｒ9はＣ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアルキル基、
Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ6ハロアルケニル基、Ｃ
2〜Ｃ6アルキニル基、Ｃ2〜Ｃ6ハロアルキニル基、Ｃ3
〜Ｃ6シクロアルキル基、Ｃ3〜Ｃ6ハロシクロアルキル
基、Ｃ4〜Ｃ7シクロアルキルアルキル基、Ｃ2〜Ｃ6アル
コキシアルキル基、Ｃ2〜Ｃ6アルキルチオアルキル基、
Ｃ2〜Ｃ6アルコキシカルボニルアルキル基、Ｃ2〜Ｃ6シ
アノアルキル基、（Ｒ5）qによって置換されていてもよ
いフェニル基、（Ｒ5）qによって置換されていてもよい
ベンジル基又は（Ｒ5）rによって置換されていてもよい
ピリジル基を示し、 Ｒ10は水素原子又はＣ1〜Ｃ6アルキル基を示し、 ｌは０〜５の整数（ただし、ｌが２〜５の場合Ｘは同一
であっても異なっていてもよい）を示し、 ｍは０〜５の整数（ただし、ｍが２〜５の場合Ｙは同一
であっても異なっていてもよい）を示し、 ｎは１〜５の整数（ただし、ｎが２〜５の場合Ｚは同一
であっても異なっていてもよい）を示し、 ｐは０〜２の整数を示し、 ｑは０〜５の整数（ただし、ｑが２〜５の場合Ｒ5は同
一であっても異なっていてもよい）を示し、 ｒは０〜４の整数（ただし、ｒが２〜４の場合Ｒ5は同
一であっても異なっていてもよい）を示す。〕で表わさ
れるセミカルバゾン化合物。1. A compound represented by the general formula [I]: [In the formula, W represents an oxygen atom or a sulfur atom, and X, Y, and Z are each independently a halogen atom, a hydroxyl group, a cyano group, a nitro group, an SCN group, a trimethylsilyl group,
R 9 , OR 9 , S (O) p R 9 group, OS (O) 2 R 9 group, O
C (O) R 9 group, C (O) R 9 group, CO 2 R 9 group, C (O)
N (R 9 ) R 10 group, SO 2 N (R 9 ) R 10 group, NHC
(O) R 9 group, N (R 9 ) R 10 group, —CH═CH—CH═CH— group formed between adjacent carbon atoms, —OCH 2 O
- group, -OCH 2 CH 2 O- group, -OCF 2 O-groups, -O
CF 2 CF 2 O- group or -OCF 2 CF 2 - represents a group, R 1 represents a hydrogen atom, the R 5, which may be substituted by R 5 C 1 ~C 6 alkyl group or a (R 5) q Represents a phenyl group which may be substituted, and R 2 , R 3 and R 4 are each independently a hydrogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group. , A C 1 -C 6 haloalkyl group, a C 2 -C 6 alkoxyalkyl group, a C 2 -C 6 alkylcarbonyl group, a C 2 -C 6 alkoxycarbonyl group, a C 2 -C 6 haloalkylcarbonyl group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, R 6 OC (O) N (R 7) S- group, R 7 (R 8) NS
A group or a benzyl group which may be substituted by (R 5 ) q , wherein R 5 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, C 1
To C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6
Alkoxy groups, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6
An alkylsulfonyl group, a C 1 to C 6 haloalkylsulfonyl group, a C 2 to C 6 alkoxycarbonyl group, an amino group or a di C 1 to C 6 alkylamino group, wherein R 6 , R 7 and R 8 are each independently A C 1 -C 6 alkyl group,
(R 5) a phenyl group or optionally substituted by q (R 5) shows a benzyl group which may be substituted by q, R 9 is C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group ,
C 2 -C 6 alkenyl groups, C 2 -C 6 haloalkenyl groups, C
2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group, C 3
To C 6 cycloalkyl group, C 3 to C 6 halocycloalkyl group, C 4 to C 7 cycloalkylalkyl group, C 2 to C 6 alkoxyalkyl group, C 2 to C 6 alkylthioalkyl group,
C 2 -C 6 alkoxycarbonyl group, C 2 -C 6 cyanoalkyl radical, (R 5) a phenyl group optionally substituted by q, (R 5) Good benzyl group or optionally substituted by q ( R 5 ) represents a pyridyl group optionally substituted by r , R 10 represents a hydrogen atom or a C 1 -C 6 alkyl group, and l represents an integer of 0 to 5 (provided that 1 is 2 to 5 represents X. Are the same or different), m is an integer of 0 to 5 (provided that when m is 2 to 5, Y may be the same or different), and n is It shows the integer of 1-5 (however, when n is 2-5, Z may be the same or different), p shows the integer of 0-2, q shows the integer of 0-5 (however. , q is the case of 2 to 5 R 5 represents a good) be different even in the same, r is an integer of 0-4 (However, when r is 2 to 4 R 5 may be different even in the same) showing a. ] The semicarbazone compound represented by these.
ルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6ハロアル
コキシ基、Ｃ1〜Ｃ6ハロアルキルチオ基又はＣ 1〜Ｃ6ハ
ロアルキルスルホニルオキシ基を示し、 Ｙが、ハロゲン原子、シアノ基、ニトロ基、Ｃ1〜Ｃ6ア
ルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6アルコキ
シ基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6アルキルチ
オ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1〜Ｃ6アルキル
スルホニル基、Ｃ1〜Ｃ6ハロアルキルスルホニル基、Ｃ
1〜Ｃ6ハロアルキルスルホニルオキシ基、隣あった炭素
原子間で形成する−ＯＣＦ2Ｏ−基又は−ＯＣＦ2ＣＦ2
Ｏ−基を示し、 Ｚが、ハロゲン原子、シアノ基、ニトロ基、Ｃ1〜Ｃ6ハ
ロアルキル基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6ア
ルキルチオ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1〜Ｃ6
アルキルスルフィニル基、Ｃ1〜Ｃ6ハロアルキルスルフ
ィニル基、Ｃ 1〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6ハ
ロアルキルスルホニル基、Ｃ1〜Ｃ6アルキルスルホニル
オキシ基、Ｃ1〜Ｃ6ハロアルキルスルホニルオキシ基、
隣あった炭素原子間で形成する−ＯＣＦ2Ｏ−基、−Ｏ
ＣＦ2ＣＦ2Ｏ−基又は−ＯＣＦ2ＣＦ2−基を示し、 Ｒ1、Ｒ2、Ｒ3、Ｒ4が各々独立して水素原子又はＣ1〜
Ｃ6アルキル基を示し、 ｌおよびｍが各々独立して０〜２の整数を示し、ｎが１
〜３の整数を示す請求項１記載のセミカルバゾン化合
物。2. W represents an oxygen atom, X is a halogen atom, a cyano group, a nitro group, C1~ C6A
Rukiru group, C1~ C6Haloalkyl group, C1~ C6Halo al
Coxy group, C1~ C6Haloalkylthio group or C 1~ C6Ha
A lower alkylsulfonyloxy group, Y is a halogen atom, cyano group, nitro group, C1~ C6A
Rukiru group, C1~ C6Haloalkyl group, C1~ C6Arcoki
Shi group, C1~ C6Haloalkoxy group, C1~ C6Alkylchi
O group, C1~ C6Haloalkylthio group, C1~ C6Alkyl
Sulfonyl group, C1~ C6Haloalkylsulfonyl group, C
1~ C6Haloalkylsulfonyloxy group, adjacent carbon
-OCF formed between atoms2O-group or -OCF2CF2
Represents an O-group, Z is a halogen atom, cyano group, nitro group, C1~ C6Ha
Lower alkyl group, C1~ C6Haloalkoxy group, C1~ C6A
Rukiruthio group, C1~ C6Haloalkylthio group, C1~ C6
Alkylsulfinyl group, C1~ C6Haloalkyl sulf
Inyl group, C 1~ C6Alkylsulfonyl group, C1~ C6Ha
Roalkylsulfonyl group, C1~ C6Alkylsulfonyl
Oxy group, C1~ C6A haloalkylsulfonyloxy group,
-OCF formed between adjacent carbon atoms2O-group, -O
CF2CF2O-group or -OCF2CF2Represents a group, R1, R2, R3, RFourAre each independently a hydrogen atom or C1~
C6Represents an alkyl group, l and m each independently represent an integer of 0 to 2, and n is 1
The semicarbazone compound according to claim 1, which represents an integer of 3 to 3.
object.
１種又は２種以上を有効成分として含有する殺虫・殺ダ
ニ剤。3. An insecticidal and acaricidal agent containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 1.
１種又は２種以上を有効成分として含有する殺虫・殺ダ
ニ剤。4. An insecticidal and acaricidal agent containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 2.
１種又は２種以上を有効成分として含有する殺菌剤。5. A fungicide containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 1.
１種又は２種以上を有効成分として含有する殺菌剤。6. A fungicide containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15499194A JP3498372B2 (en) | 1993-10-05 | 1994-07-06 | Semicarbazone compound |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5-249596 | 1993-10-05 | ||
| JP24959693 | 1993-10-05 | ||
| JP15499194A JP3498372B2 (en) | 1993-10-05 | 1994-07-06 | Semicarbazone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07149706A JPH07149706A (en) | 1995-06-13 |
| JP3498372B2 true JP3498372B2 (en) | 2004-02-16 |
Family
ID=26483107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15499194A Expired - Fee Related JP3498372B2 (en) | 1993-10-05 | 1994-07-06 | Semicarbazone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3498372B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6049006A (en) * | 1997-06-16 | 2000-04-11 | American Home Products Corp. | Elevation of HDL cholesterol by N-[2-[(aminothioxomethyl) hydrazono]-2-arylethyl]amides |
| US6034272A (en) * | 1997-06-16 | 2000-03-07 | American Home Products Corporation | Elevation of HDL cholesterol by N-[4-[(aminothioxomethyl) hydrazono]-4-arylbutyl]amides |
-
1994
- 1994-07-06 JP JP15499194A patent/JP3498372B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07149706A (en) | 1995-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |