WO2022196695A1 - Thienouracil compound and harmful organism control agent - Google Patents
Thienouracil compound and harmful organism control agent Download PDFInfo
- Publication number
- WO2022196695A1 WO2022196695A1 PCT/JP2022/011678 JP2022011678W WO2022196695A1 WO 2022196695 A1 WO2022196695 A1 WO 2022196695A1 JP 2022011678 W JP2022011678 W JP 2022011678W WO 2022196695 A1 WO2022196695 A1 WO 2022196695A1
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- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- compound
- integer
- ome
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 391
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 103
- 150000003839 salts Chemical class 0.000 claims abstract description 99
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 57
- -1 —C(O)R 9 Chemical group 0.000 claims description 160
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 43
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical group [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 28
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 20
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 17
- 239000000417 fungicide Substances 0.000 claims description 17
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 229940121375 antifungal agent Drugs 0.000 claims description 7
- 239000003429 antifungal agent Substances 0.000 claims description 7
- 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 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
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- 235000002639 sodium chloride Nutrition 0.000 description 91
- 239000002585 base Substances 0.000 description 71
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- 238000012360 testing method Methods 0.000 description 49
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 28
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
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- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- IHMQNZFRFVYNDS-UHFFFAOYSA-N tert-butyl n-amino-n-methylcarbamate Chemical compound CN(N)C(=O)OC(C)(C)C IHMQNZFRFVYNDS-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- UQCWXKSHRQJGPH-UHFFFAOYSA-M tetrabutylazanium;fluoride;hydrate Chemical compound O.[F-].CCCC[N+](CCCC)(CCCC)CCCC UQCWXKSHRQJGPH-UHFFFAOYSA-M 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- AUZONCFQVSMFAP-UHFFFAOYSA-N tetraethylthiuram disulfide Natural products CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 description 1
- 229960003053 thiamphenicol Drugs 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229940092292 tiamulin fumarate Drugs 0.000 description 1
- 229950007146 tigolaner Drugs 0.000 description 1
- 229960000757 tilmicosin phosphate Drugs 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 229960000323 triclabendazole Drugs 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- IGOWHGRNPLFNDJ-UHFFFAOYSA-N tricos-9t-ene Natural products CCCCCCCCCCCCCC=CCCCCCCCC IGOWHGRNPLFNDJ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 description 1
- 229960002859 tulathromycin Drugs 0.000 description 1
- DBHVHTPMRCXCIY-UHFFFAOYSA-N tyclopyrazoflor Chemical compound N1=C(Cl)C(N(C(=O)CCSCCC(F)(F)F)CC)=CN1C1=CC=CN=C1 DBHVHTPMRCXCIY-UHFFFAOYSA-N 0.000 description 1
- 229940031989 tylosin phosphate Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LLYYNOVSVPBRGV-MVNKZKPCSA-N valnemulin Chemical compound CC(C)[C@@H](N)C(=O)NCC(C)(C)SCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 LLYYNOVSVPBRGV-MVNKZKPCSA-N 0.000 description 1
- 229950008166 valnemulin Drugs 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004549 water soluble granule Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/695—Silicon compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
Definitions
- the present invention relates to novel thienouracil compounds and salts thereof, and pest control agents containing the compounds and salts thereof as active ingredients.
- Certain thienouracil compounds are known to have bactericidal activity (see, for example, Patent Documents 1 to 11).
- the present inventors have made intensive studies with the goal of solving the above problems, and as a result, the novel thienouracil compound represented by the following formula (1) according to the present invention is excellent as a fungicide, especially as an agricultural and horticultural fungicide.
- the present invention was completed based on the discovery that the pest control activity was
- the thienouracil compounds according to the present invention are not disclosed in any literature, and their usefulness as pest control agents is unknown.
- the present invention relates to the following [1].
- R 1 represents a hydrogen atom or C 1 to C 6 alkyl
- R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 cycloalkoxycarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65; represent, G-1 to G-65 each represent a structure represented by the following structural formula,
- R 3 represents phenyl, phenyl substituted by (Z) m1 , F-31 or F-34;
- F-31 and F-34 represent structures represented by the following structural formulas,
- R 4 is —C ⁇ C—R 7 , C 1 -C 6 alkyl substituted by R 15 , C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, L- 1 to L-3 or L-4, L-1 to L-6, L-8 and L-9 represent structures represented by the following structural formulas,
- R 5 represents C 1 -C 6 alkyl
- R b represents a hydrogen atom
- R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to representing E-90, L-5, L-6, L-8 or L-9
- R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10
- E-1 to E-90 each represent a structure represented by the following structural formula,
- each Z 9 may be the same as or different from each other
- p3 represents an integer of 2 or 3
- p5 represents an integer of 2, 3, 4 or 5
- p6 represents an integer of 2
- 4 or 6 p7
- p8 represents an integer of 2
- 4, 5, 6 or 7, p8 represents an integer of 2
- 4, 5, 6, 7 or 8 p9 represents an integer of 2, 3, 4, 5, 6, 7,
- each Z 10 may be identical to each other or relative to each other.
- the compound of the present invention exhibits excellent control activity against many pathogenic bacteria.
- the present invention can provide useful fungicides, especially agricultural and horticultural fungicides.
- the thienouracil compound which is the compound of the present invention, has two types of geometric isomers based on the presence of alkenyl groups substituted on the uracil ring, that is, the compound represented by formula (1a) and the compound represented by formula (1b).
- the represented compound exists.
- the present invention includes the compound represented by the formula (1a), the compound represented by the formula (1b), or the compound represented by the formula (1a) and the compound represented by the formula (1b) in an arbitrary ratio. It includes mixtures.
- the compounds of the present invention may have E- and Z-form geometric isomers depending on the type of substituents. in any proportion.
- the compounds of the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, but the present invention includes all optically active forms and racemic forms. It includes.
- the compound of the present invention may have tautomers depending on the type of substituent, but the present invention includes all tautomers or mixtures of tautomers in any ratio. is.
- the compounds of the present invention may exist as one or more rotamers due to restricted bond rotation caused by steric hindrance between substituents. or mixtures of diastereomers in any proportion.
- some compounds of the present invention have a heterocyclic ring in which the nitrogen atom constituting the ring on the heterocyclic group can be oxidized by an oxygen atom (e.g., pyridine ring, etc.). It includes
- those that can be converted into salts by conventional methods include, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, nitric acid, sulfuric acid, Salts of inorganic acids such as phosphoric acid, chloric acid and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid; formic acid, acetic acid, propionic acid , trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, salts of carboxylic acids such as citric acid, glutamic acid, aspart
- Amino acid salts alkali metal salts such as lithium, sodium and potassium, alkaline earth metal salts such as calcium, barium and magnesium, aluminum salts, tetramethylammonium salts, tetrabutylammonium salts, benzyltrimethylammonium salts, etc. Ammonium salts can be used.
- n- means normal
- i- means iso
- s- means secondary
- tert- means tertiary
- Ph means phenyl
- Halogen atoms in the present specification include fluorine atoms, chlorine atoms, bromine atoms and iodine atoms. In addition, the notation of "halo” also represents these halogen atoms in this specification.
- C a -C b alkyl represents a linear or branched saturated hydrocarbon group having a to b carbon atoms, such as methyl, ethyl, n-propyl, Specific examples include i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, n-hexyl and the like. Selected by range.
- C a -C b alkenyl as used herein means a linear or branched chain consisting of a to b carbon atoms and having one or more double bonds in the molecule. represents an unsaturated hydrocarbon group having a Specific examples include 2-propenyl and the like, and are selected within the specified range of the number of carbon atoms.
- C a -C b haloalkenyl used herein means a linear or branched chain having a to b carbon atoms in which hydrogen atoms bonded to carbon atoms are optionally substituted with halogen atoms. and represents an unsaturated hydrocarbon group having one or more double bonds in the molecule, and specific examples thereof include 1-chloro-1-propenyl, etc., and is selected in the range of
- C a -C b alkoxy represents an alkyl-O- group having a to b carbon atoms as defined above, such as methoxy, ethoxy, n-propyloxy, i Specific examples include -propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, etc., and are selected within the designated number of carbon atoms.
- C a -C b cycloalkyl in this specification represents a cyclic hydrocarbon group having a to b carbon atoms, and has a 3- to 10-membered monocyclic or composite ring structure. can be formed. Each ring may also be optionally substituted with alkyl within the specified number of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., and each is selected within the designated number of carbon atoms. .
- C a -C b alkylcarbonyl as used herein means an alkyl-C(O)- group having a to b carbon atoms as defined above, such as acetyl, propionyl, butyryl, Specific examples include isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, heptanoyl and the like, and each is selected within the specified number of carbon atoms.
- C a -C b alkoxycarbonyl in this specification represents an alkyl-O-C(O)- group having a to b carbon atoms as defined above, such as methoxycarbonyl, ethoxy Specific examples include carbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl and the like. is selected within the specified number of carbon atoms.
- C a -C b cycloalkoxycarbonyl represents a cycloalkyl-O-C(O)- group having a to b carbon atoms as defined above, such as cyclopropyl Specific examples include oxycarbonyl, cyclohexyloxycarbonyl, and the like, and are selected within the specified range of the number of carbon atoms.
- C a -C b alkylthio in the present specification represents an alkyl-S-group having a to b carbon atoms as defined above, such as methylthio, ethylthio, n-propylthio, i- Specific examples include propylthio, n-butylthio, i-butylthio, s-butylthio, tert-butylthio and the like, each selected within the specified number of carbon atoms.
- C a -C b alkylsulfinyl represents the above-described alkyl-S(O)-group having a to b carbon atoms, such as methylsulfinyl, ethylsulfinyl, Specific examples include n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, tert-butylsulfinyl and the like, and each is selected within the designated number of carbon atoms. .
- C a -C b alkylsulfonyl as used herein means an alkyl-SO 2 - group having a to b carbon atoms as defined above, such as methylsulfonyl, ethylsulfonyl, n- Specific examples include propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl and the like, and each is selected within the specified number of carbon atoms.
- C a -C b alkylamino refers to an amino group in which one of the hydrogen atoms is substituted by the aforementioned alkyl having a to b carbon atoms, for example, methyl Specific examples include amino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, tert-butylamino and the like, each selected within the specified number of carbon atoms. .
- di(C a -C b alkyl)amino has the above-described meaning in which both hydrogen atoms have a to b carbon atoms which may be the same or different from each other.
- alkyl is, for example, dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di
- Specific examples include (n-butyl)amino and the like, which are selected within the specified range of the number of carbon atoms.
- C a -C b alkylaminocarbonyl as used herein means amino-C(O)- in which one of the hydrogen atoms is substituted by alkyl having a to b carbon atoms as defined above. specific examples include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, i-propylaminocarbonyl, n-butylaminocarbonyl, i-butylaminocarbonyl, tert-butylaminocarbonyl and the like. , are selected in each specified range of carbon atoms.
- di(C a -C b alkyl)aminocarbonyl in this specification means that both hydrogen atoms have a to b number of carbon atoms which may be the same or different from each other.
- Specific examples include aminocarbonyl, di(n-propyl)aminocarbonyl, di(n-butyl)aminocarbonyl and the like, and each is selected within the designated number of carbon atoms.
- di(C a -C b alkyl)aminosulfonyl in this specification means that both hydrogen atoms have a to b number of carbon atoms which may be the same or different from each other.
- tri(C a -C b alkyl)silyl in this specification is substituted by an alkyl group having the above-mentioned meaning and having a to b carbon atoms which may be the same or different from each other. represents a silyl group.
- Specific examples include trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, tert-butyldimethylsilyl and the like. is selected within the specified number of carbon atoms.
- C a -C b alkyl substituted by R 8 represents an alkyl group having a to b carbon atoms and having the above-mentioned meaning, in which a hydrogen atom bonded to a carbon atom is optionally substituted with any R 8 , R 11 or R 15 ; Selected within a specified range of carbon atoms.
- R 8 , R 11 or R 15 may be the same or different. good too.
- C a -C b cycloalkyl substituted with R 16 refers to the number of carbon atoms from a to b in which a hydrogen atom attached to a carbon atom is optionally replaced with any R 16 .
- each R 16 may be the same or different.
- phenyl substituted by (Z) m1 or "phenyl substituted by (Z1) m " as used herein means that the hydrogen atom attached to the carbon atom by any Z or Z1 is optionally represents a substituted phenyl group.
- m can take any value according to (Z 1 ) m
- m1 can take any value according to (Z) m1 .
- each Z or Z 1 may be the same or different.
- the compound of the present invention represented by formula (1) can be produced, for example, by the following method.
- the following explanation is merely an example, and the compound of the present invention represented by formula (1) may be produced by other methods.
- the compound of the present invention represented by formula (1) is also referred to as “the compound of the present invention (1)”
- the compound represented by formula (2) is referred to as “compound (2)”. Also described.
- Other compounds are similarly described accordingly.
- Compound (1) of the present invention can be produced, for example, by reacting compound (2) with compound (3).
- L is a chlorine atom, a bromine atom, an iodine atom, C 1 -C 4 alkylsulfonyloxy (e.g., methanesulfonyloxy, etc.), halosulfonyloxy (e.g., fluorosulfonyloxy, etc.), C 1 -C 4 haloalkyl represents a leaving group such as sulfonyloxy (e.g., trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (e.g., paratoluenesulfonyloxy, etc.), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Rb has the same meaning as above.
- Compound (1) can be produced by reacting compound (2) and compound (3) in a solvent or in the absence of a solvent, optionally in the presence of a base.
- the equivalent of compound (3) used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (2).
- Some compounds (3) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
- the solvent to be used may be inert to the reaction.
- examples include water, alcohol solvents such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like.
- Ether solvents aromatic hydrocarbon solvents such as benzene, xylene and toluene; aliphatic hydrocarbon solvents such as pentane, hexane and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform and 1,2-dichloroethane; Nitrile solvents such as nitrile, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, dimethylsulfoxide, and mixed solvents thereof. .
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo [2.2.2 ] octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), organic bases such as 1,5-diazabicyclo[4.3.0]-5-nonene (DBN), Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate and potassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents per equivalent
- the reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture.
- the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can be set arbitrarily within the range of usually 5 minutes to 100 hours.
- Compound (1-4) is obtained by reacting compound (1-3) and compound (4) in a solvent or in the absence of a solvent, optionally in the presence of one or both of a base and an additive. It can be manufactured by
- the equivalent of compound (4) used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (1-3).
- Some compounds (4) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
- the solvent to be used may be inert to the reaction, and examples thereof include the solvents exemplified in Production Method 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-3).
- the reaction can be carried out in the presence of additives.
- Additives that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, and the like. mentioned.
- the amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (1-3).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- compound (1-5) in which R 2 is A 1 can be produced, for example, by reacting compound (1-3) with compound (5).
- Compound (1-5) can be produced by reacting compound (1-3) and compound (5) in a solvent or in the absence of a solvent, optionally in the presence of a base.
- the equivalent of compound (5) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (1-3).
- Some compounds (5) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-3).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (1-7) is prepared by reacting compound (1-6) and compound (6) in a solvent or in the absence of a solvent, optionally in the presence of a palladium catalyst, optionally with a copper catalyst, an additive, a fluoride and a base in the presence of any one or more, it can be produced by reacting.
- the equivalent of compound (6) to be used can be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (1-6).
- Some compounds (6) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be carried out in the presence of a palladium catalyst.
- Palladium catalysts that can be used include, for example, palladium acetate, tetrakis(triphenylphosphine)palladium (zero valence), tris(dibenzylideneacetone) dipalladium (0 valence), bis(triphenylphosphine) palladium (bivalence) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloro pyridyl)palladium (divalent) dichloride and the like.
- the amount (equivalent) of the palladium catalyst used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
- the reaction can be carried out in the presence of a copper catalyst.
- Copper catalysts that can be used include, for example, copper iodide and copper chloride (monovalent).
- the amount (equivalent) of the copper catalyst used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
- Additives that can be used include, for example, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene.
- the amount (equivalent) of the additive used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
- the reaction can be performed in the presence of fluoride.
- Fluorides that can be used include, for example, tetra-n-butylammonium fluoride and the like.
- the amount (equivalent) of fluoride to be used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-6).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- the compound (1-8) in which R 4 is —C ⁇ CH can be produced, for example, by reacting the compound (1-9) with a base.
- Compound (1-8) can be produced by reacting compound (1-9) in the presence of a base in a solvent or without solvent.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents per equivalent of compound (1-9).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- the compound (2) used in Production Example 1 can be produced, for example, according to the production route (reaction route) shown by the following reaction formula.
- Compound (2) can be obtained by reacting compound (3-a) and compound (A) in a solvent or in the absence of a solvent, optionally in the presence of a base.
- the equivalent amount of compound (A) used can be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (3-a).
- Some of the compounds (A) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-a).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (3-a) can be obtained by reacting compound (3-b) with a base in a solvent or without solvent.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-b).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (3-b) is obtained by reacting compound (3-c) with carbonyldiimidazole or triphosgene in a solvent or in the absence of a solvent, optionally in the presence of a base, and then reacting with compound (B). be able to.
- the equivalent of carbonyldiimidazole or triphosgene used can be in the range of 0.5 to 50 equivalents per equivalent of compound (3-c).
- the equivalent of compound (B) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-c).
- Some of the compounds (B) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-c).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Some compounds (3-c) are known compounds described in WO 2013/071169, and others can be synthesized in the same manner as known compounds according to the method described in the document. .
- compound (2-a) in which R 2 is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
- reaction Formula 2 (In the formula, R 2a represents C 1 to C 6 alkoxycarbonyl, and R 1 , R 3 , R 4 , R 5 and R b have the same meanings as above.)
- Compound (2-a) can be obtained by reacting compound (2-b) in the presence of an acid in a solvent or without solvent.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be carried out in the presence of an acid.
- Acids that can be used include, for example, hydrochloric acid, sulfuric acid, nitric acid, acetic acid, trifluoroacetic acid, p-toluenesulfonic acid monohydrate, and the like.
- the amount (equivalent) of the acid used can be 0.1 to 100 equivalents per equivalent of compound (2-b).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- the compound (1-6) used in Production Example 4 can be produced, for example, according to the production route (reaction pathway) shown in the reaction scheme below.
- Compound (1-6) can be synthesized according to the method described in Production Example 1 by reacting compound (2-c) with compound (3).
- Compound (2-c) can be obtained by reacting compound (3-d) with compound (A) above in a solvent or in the absence of a solvent, optionally in the presence of a base.
- the equivalent of compound (A) used can be in the range of 0.5 to 50 equivalents per equivalent of compound (3-d).
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-d).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (3-d) can be obtained by reacting compound (3-e) with a halogenating agent in a solvent or in the absence of a solvent, optionally in the presence of additives.
- halogenating agents examples include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like.
- the amount (equivalent) of the halogenating agent to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-e).
- the solvent to be used may be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1, acetic acid, and the like.
- the reaction can be carried out in the presence of additives.
- Additives that can be used include, for example, sodium acetate.
- the amount (equivalent) of the additive used can be 0.1 to 100 equivalents per equivalent of compound (3-e).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- compound (3-f) in which R4 is L-1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
- Compound (3-f) is obtained by reacting compound (3-g) and compound (C) in a solvent or in the absence of a solvent, optionally in the presence of one or more of a condensing agent, an additive and a base.
- a condensing agent an additive and a base.
- the equivalent of compound (C) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-g).
- Some of the compounds (C) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be carried out in the presence of a condensing agent.
- Condensing agents that can be used include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride, 2-chloro-1-methylpyridinium iodide, propylphosphonic anhydride and the like.
- the amount (equivalent) of the condensing agent to be used can be 0.1 to 100 equivalents per equivalent of compound (3-g).
- Additives that can be used include, for example, 4-dimethylaminopyridine, 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole and the like.
- the amount (equivalent) of the additive used can be 0.005 to 20 equivalents per equivalent of compound (3-g).
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents per equivalent of compound (3-g).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (3-g) can be obtained by reacting compound (3-h) in a solvent or without a solvent in the presence of a base.
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-h).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- compound (2-d) can be produced, for example, according to the production route (reaction route) shown in the following reaction scheme.
- Compound (3-k) can be obtained by reacting compound (3-g) with a reducing agent in a solvent or in the absence of a solvent, optionally in the presence of an additive.
- the reaction can be carried out in the presence of a reducing agent.
- reducing agents include, for example, sodium borohydride, lithium borohydride, lithium aluminum hydride and the like.
- the equivalent of the reducing agent can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-g).
- the reaction can be carried out in the presence of additives.
- Additives that can be used include, for example, 1,1'-carbonyldiimidazole and the like.
- the equivalent of the additive can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-g).
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (2-e) can be obtained by reacting compound (3-k) with compound (A) in a solvent or in the absence of a solvent, optionally in the presence of a base.
- the equivalent of compound (A) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-k).
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-k).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (2-d) is prepared by combining compound (2-e) and an alcohol represented by R a OH (wherein R a has the same meaning as defined above) in a solvent or in the absence of a solvent, optionally in the presence of an acid. It can be obtained by a lower reaction.
- the reaction can be carried out in the presence of an alcohol represented by R a OH.
- Alcohols that can be used are those included in R a OH, and examples thereof include methanol, ethanol, isopropanol, and the like.
- the equivalent of the alcohol used can be in the range of 1 to 1000 equivalents with respect to 1 equivalent of compound (2-e).
- the reaction can be carried out in the presence of an acid.
- Acids that can be used include, for example, the acids exemplified in Reaction Scheme 1.
- the amount (equivalent) of the acid used can be 0.01 to 100 equivalents per equivalent of compound (2-e).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- compound (2-g) in which R 4 is L-2 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
- Compound (2-f) can be obtained by reacting compound (2-g) in a solvent or in the absence of a solvent, optionally in the presence of an acid.
- the reaction can be carried out in the presence of an acid.
- Acids that can be used include, for example, the acids exemplified in Reaction Formula 2.
- the amount (equivalent) of the acid used can be 0.01 to 100 equivalents per equivalent of compound (2-g).
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (2-g) can be obtained by reacting compound (2-h) with thiourea in a solvent or without solvent, and then reacting with a base.
- the equivalent of thiourea to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (2-h).
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-h).
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Compound (2-h) can be obtained by reacting compound (3-i) with compound (A) in a solvent or in the absence of a solvent, optionally in the presence of a base.
- the equivalent of compound (A) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-i).
- the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
- the reaction can be performed in the presence of a base.
- Bases that can be used include, for example, the bases exemplified in Production Example 1.
- the amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-i).
- reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
- Reaction Formula 7 (Wherein, R 4′ represents a hydrogen atom, a halogen atom, —C(O)OR a or —C(O)NHCH 2 CH 2 X, and X, R 1 , R 2 , R 3 , R 5 , R a and Rb have the same meanings as above.)
- Compound (3′-a) can be synthesized according to the method described in Reaction Scheme 1.
- compound (2') including compound (2-c) and compound (2-h) can be prepared by combining compound (3'-a) and compound (A) in a solvent or without a solvent, optionally in the presence of a base. It can be obtained by a lower reaction.
- the compound (2'-a) in which R 2 is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
- reaction Formula 8 (In the formula, R 1 , R 2a , R 3 , R 4′ , R 5 and R b have the same meanings as above.)
- Compound (2'-a) can be obtained by reacting compound (2'-b) in the presence of an acid in a solvent or without solvent.
- reaction conditions are the same as those described in Reaction Formula 2.
- reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water and then concentrated or put into ice water, extracted with an organic solvent and then concentrated. Workup can be carried out to obtain the desired compound.
- purification it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography, liquid chromatography, and the like.
- the compounds of the present invention that can be produced using these methods include, for example, the compounds shown in Table 1.
- Table 1 is for illustration only, and the compounds of the present invention are not limited to these.
- Me represents methyl
- Et represents ethyl
- ⁇ represents a triple bond
- T-01 to T-26 represent the following structures.
- notations U-01 to U-09 represent the following structures.
- the asterisks "*" in the structural formulas of T-01 to T-26 and U-01 to U-09 represent the binding sites.
- R 2 is T-01
- R 6 is U-01
- R 4 is 4,5-dihydrooxazol-2-yl
- (Z) m1 is 2-OMe-
- 5-F it represents the following compounds.
- R 4 is 4,5-dihydrooxazol-2-yl
- (Z) m1 is 2-OMe-5-F.
- Table 2 contains Tables 1-02 through Tables 1-02, each constructed similarly to Table 1, except that the conditions for R 4 and (Z) m1 in Table 1 have been replaced with different conditions. 1-21 table.
- Table 1-02 applies the conditions of Table 1 (ie, "R 4 is 4,5-dihydrooxazol-2-yl and (Z) m1 is 2-OMe-5-F.”). ) is replaced by the condition of row Table 1-02 in Table 2 (i.e., "R 4 is methoxymethyl and (Z) m1 is 2-OMe-5-F.") It is structured the same as Table 1, except that
- Table 2 Table Conditions ⁇ Table 1-02 R 4 is methoxymethyl, (Z) m1 is 2-OMe-5-F. Table 1-03 R 4 is -C ⁇ CMe, (Z) m1 is 2-OMe-5-F. Table 1-04 R 4 is 4,5-dihydrooxazol-2-yl, (Z) m1 is unsubstituted. Table 1-05 R 4 is methoxymethyl, (Z) m1 is unsubstituted. Table 1-06 R 4 is -C ⁇ CMe, (Z) m1 is unsubstituted. Table 1-07 R 4 is 4,5-dihydrooxazol-2-yl, (Z) m1 is 2-OMe.
- R 4 is methoxymethyl, (Z) m1 is 2-OMe.
- Table 1-09 R 4 is -C ⁇ CMe, (Z) m1 is 2-OMe.
- Table 1-10 R 4 is 4,5-dihydrooxazol-2-yl, (Z) m1 is 2-OEt.
- Table 1-11 R 4 is methoxymethyl, (Z) m1 is 2-OEt.
- Table 1-12 R 4 is -C ⁇ CMe, (Z) m1 is 2-OEt.
- Table 1-13 is 4,5-dihydrooxazol-2-yl, (Z) m1 is 3-F.
- Table 1-14 R 4 is methoxymethyl, (Z) m1 is 3-F.
- R 4 is -C ⁇ CMe, (Z) m1 is 3-F.
- Table 1-16 R 4 is 4,5-dihydrooxazol-2-yl, (Z) m1 is 3-Me.
- Table 1-17 R 4 is methoxymethyl, (Z) m1 is 3-Me.
- Table 1-18 R 4 is -C ⁇ CMe, (Z) m1 is 3-Me.
- Table 1-19 R 4 is 4,5-dihydrooxazol-2-yl, (Z) m1 is 3-Cl.
- Table 1-20 is methoxymethyl, (Z) m1 is 3-Cl.
- Table 1-21 R 4 is -C ⁇ CMe, (Z) m1 is 3-Cl. ⁇
- Examples of agriculturally acceptable salts of the compound of the present invention include hydrochloride, hydrobromide, hydroiodide, formate, acetate or oxalate.
- the compound of the present invention is generally used as an agricultural and horticultural bactericidal and fungicidal agent against various diseases caused by Necrophytes, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, Bacteria or viruses. can be used.
- pathogen means microorganisms that cause plant diseases, and specifically includes, but is not limited to, the following microorganisms. (eg, Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (eg, Candida albicans, C. sorbosa, etc.), Pichia spp. (eg, Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. Cercosporidium spp., Cladosporium spp. (e.g.
- Paracercospora spp. e.g. Paracercospora egenula etc.
- Phaeoisariopsis spp. Phaeoramularia spp.
- Ramichloridium spp. Ramularia spp., Septogloeum spp. , Septoria spp. (e.g. Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g. Elsinoe ampelina, E. araliae, E. fawcettii etc.), Sphaceloma spp.
- Ramichloridium spp. Ramularia spp.
- Septogloeum spp. Septoria spp.
- Septoria spp. e.g. Septoria albopunctata, S. apiicola, S.
- Leptosphaeria spp. e.g., Leptosphaeria coniothyrium, L. maculans, etc.
- Saccharicola spp. Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.)
- Ophiosphaerella spp. Setophoma spp. alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A.
- Bipolaris spp. e.g. Bipolaris sorghicola etc.
- Cochliobolus spp. e.g. Cochliobolus heterostrophus, C. lunatus, C. miyabeanus etc.
- Curvularia spp. Pleospora spp. (e.g. Pleospora herbarum etc.), Pyrenophora spp. nea, P. teres etc.), Setosphaeria spp. (e.g. Setosphaeria turcica etc.), Stemphylium spp.
- Venturia carpophila V.
- spp. eg, Schizothyrium pomi, etc.
- Acrospermum spp. Leptosphaerulina spp., Aspergillus spp.
- Penicillium spp. eg, Penicillium digitatum, P. italicum, P. sclerotigenum, etc.
- Microsporum spp. Trichophyton spp. (e.g., Trichophyton mentagrophytes, T rubrum etc.), Histoplasma spp., Blumeria spp. cichoracearum, E. heraclei, E. pisi, etc.), Golovinomyces spp.
- Phyllactinia spp. e.g. Phyllactinia kakicola, P. mali, P. moricola etc.
- Podosphaera spp. e.g. Sphaerotheca spp.
- Sphaerotheca spp. e.g. Sphaerotheca aphanis var. aphanis, S. fuliginea etc.
- Uncinula spp. U. s. var. tandae etc.
- Blumeriella spp. e.g.
- Valdensia heterodoxa etc. Claviceps spp. , Hypomyces solani f. sp. mori, H. s. f. sp. pisi, etc.), Trichoderma spp. (e.g., Trichoderma viride, etc.), Calonectria spp. , Fusarium spp. (e.g., Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. o. f. sp. adzukicola, F. o. f. sp. allii, F. o. f. sp.
- Fusarium spp. e.g., Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. o.
- Haematonectria spp. Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. albo-atrum, V. dahliae, V. longisporum etc.), Ceratocystis spp. (e.g. Ceratocystis ficicola, C. fimbriata etc.), Thielaviopsis spp. (e.g., Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp.
- Pestalotiopsis funerea e.g., Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.
- Physalospora spp. Nemania spp., Nodulisporium spp., Roselinia spp. (e.g., Roselinia necatrix etc.), Monographella spp. spp. (e.g. Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae etc.), Diaporthopsis spp., Phomopsis spp. spp., Discula spp.
- Phyllachora pomigena etc. Ellisembia spp., Briosia spp., Cephalosporium spp. fructicola etc.), Phaeocytostroma spp., Phialophora spp. Fungi of the phylum Ascomycota.
- Septobasidium spp. e.g. Septobasidium bogoriense, S. tanakae etc.
- Helicobasidium spp. e.g. Helicobasidium longisporum etc.
- Physopella spp. e.g.
- Physopella ampelopsidis etc. Kuehneola spp. (e.g. Kuehneola japonica etc.), Phragmidium spp. etc.), Gymnosporangium spp. (e.g. Gymnosporangium asiaticum, G. yamadae etc.), Puccinia spp. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P.
- Uromyces spp. e.g., Uromyces phaseoli var. azukicola, U.p. var. phaseoli, Uromyces viciae-fabae var. , Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp.
- Uromyces spp. e.g., Uromyces phaseoli var. azukicola, U.p. var. phaseoli, Uromyces viciae-fabae var.
- Tranzschelia spp. e.g., Tranzschelia discolor, etc.
- Aecidium spp. Blastospora spp.
- Exobasidium spp. e.g. Exobasidium reticulatum, E. vexans, etc.
- Microstroma spp. Tilletia spp. etc.
- Cryptococcus spp. Bovista spp. (e.g., Bovista dermoxantha etc.), Lycoperdon spp. Marasmius oreades etc.), Armillaria spp., Helotium spp., Lepista spp. (e.g.
- Athelia spp. e.g. Athelia rolfsii etc.
- Ceratobasidium spp. Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaete spp.
- Fungi of the phylum Chitridiomycota such as Olpidium spp.
- Fungi of the phylum Blastocladiomycota such as Physoderma spp.
- Mucoromycotina such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis), Rhizopus spp. ) fungi.
- Protists of the phylum Cercozoa such as Plasmodiophora spp. (eg Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea.
- Aphanomyces spp. e.g. Aphanomyces cochlioides, A. raphani etc.
- Albugo spp. e.g. Albugo macrospora, A.
- Actinobacteria such as Clavibacter spp. (e.g. Clavibacter michiganensis subsp. michiganensis), Curtobacterium spp., Leifsonia spp. of Gram-positive bacteria.
- Gram-positive fungi of the phylum Firmicutes such as Clostridium sp.
- Gram-positive fungi of the phylum Tenericutes, such as Phytoplasma.
- Rhizobium spp. e.g. Rhizobium radiobacter etc.
- Acetobacter spp. Burkholderia spp. avenae, A. a. subsp. citrulli, A.
- plant diseases caused by infection/proliferation of these pathogenic fungi include, but are not limited to, the following plant diseases.
- cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (Oidium sp.), oyster powdery mildew (Phyllactinia kakicola), burdock powdery mildew (Podospha), eggplant powder
- simulans U. s. var. tandae
- zucchini milk melon powdery mildew
- Podosphaera xanthii strawberry powdery mildew
- Sphaerotheca aphanis var. aphanis watermelon
- Melon powdery mildew Sphaerotheca fuliginea
- Grape powdery mildew Uncinula necator, U. n. var.
- Botrytis blight Botrytis cinerea
- Chinese chive leaf blight Leaf blight Botrytis cinerea, B. byssoidea, B. squamosa
- Faba bean red spot Chocolate spot Botrytis cinerea, B. elliptica, B. fabae
- Brown rot Monilinia fructicola, M. fructigena, M.
- Glycines Fusarium virguliforme
- Bakanae disease in rice Gibberella fujikuroi
- Verticillium black spot Verticillium albo-atrum, V. dahliae
- tomato Verticillium wilt
- Verticillium dahliae of eggplant and butterbur
- Ceratocystis canker Ceratocystis ficicola
- Black rot Ceratocystis fimbriata
- Gray blight Pestalotiopsis longiseta
- Endothia canker (Cryphonectria parasitica), Citrus black spot (Diaporthe citri), Stem blight (Phomopsis asparagi), Phomopsis canker (Phomopsis fukushii), Eggplant brown spot (Phomopsis vexans), Tea Anthracnose (Discula theae-sinensis), Apple rot Valsa canker (Valsa ceratosperma), Rice blast Blast (Magnaporthe grisea), Strawberry anthracnose Crown rot (Colletotrichum acutatum, C.
- Net blister blight (Exobasidium reticulatum), Tea blister Bl ister blight (Exobasidium vexans), white silk disease Stem rot, Southern blight (Athelia rolfsii), chrysanthemum wilt Root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger sheath blight (Rhizoctonia solani), cabbage seedling blight Damping-off (Rhizoctonia solani), Damping-off (Rhizoctonia solani), Bottom rot (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Sheath blight (Thanatephorus cucumeris), beet root rot (Thanatephorus cucumeris), beet leaf rot Leaf blight (Thanatephorus cucumeris), fig black mold Rhizopus rot (Rhizopus s
- Bacterial Frui t blotch (Acidovorax avenae subsp. citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens), Plum black spot Bacterial leaf spot (Xanthomonas arboricola pv.
- Bacterial spot (Pseudomonas syringae pv. lachrymans), Bacterial black spot (Pseudomonas syringae pv) maculicola), Bacterial canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), Bacterial shoot blight (Pseudomonas syringae pv.
- Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum) , Fire blight (Erwinia amylovora) of the family Pear family, konnyaku rot Soft rot (Pectobacterium carotovorum), soft rot Bacterial soft rot (Pectobacterium carotovorum).
- control agents against diseases of agricultural and horticultural crops has progressed, and a wide variety of agents have been put into practical use to date.
- pathogenic bacteria have acquired drug resistance, and there are increasing cases where it is difficult to control them with the existing fungicides that have been conventionally used.
- some of the existing drugs are highly toxic, and some of them remain in the environment for a long period of time, thereby disturbing the ecosystem.
- the compounds of the present invention have excellent control activity against many pathogens and have high safety against target crops.
- the compound of the present invention can exert a sufficient control effect against pathogenic bacteria that have acquired resistance to existing fungicides.
- the compounds of the present invention do not cause phytotoxicity to target crops, have almost no adverse effects on mammals, fish and beneficial insects, are low in residue, and have a low environmental impact.
- the compound of the present invention can be It can also be used as an antibacterial and antifungal agent for textiles and leather, and as an industrial disinfectant for cooling water channels in manufacturing plants.
- pathogenic bacteria examples include trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, candida fungi such as Candida albicans, aspergillus fungi such as Aspergillus fumigatus, and cryptococcus fungi such as Cryptococcus neoformas.
- Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa and Haemophilus influenzae
- Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes, etc. include, but are not limited to, these.
- Strains targeted as antibacterial and antifungal agents include, for example, wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor, Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans , Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria.
- wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor
- Aspergillus niger Aspergillus terreus
- Eurotium tonophilum Eurotium tonophilum
- Penicillium citrinum Penicillium funiculosum
- Rhizopus oryzae Cladosporium clado
- Strains targeted as industrial fungicides include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera.
- the compound of the present invention can also be used as an internal parasite control agent for livestock, poultry, pets, and the like.
- target endoparasites include, but are not limited to, the following. Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Esphagostomum Genus Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis ), Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris and other nematodes ; Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa; Dracunculidae nematodes such as Dracunculus; Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminu
- the compound of the present invention can be used as an antifungal agent in addition to being used as an agricultural and horticultural fungicide.
- pathogenic bacteria that can be used as antifungal agents include, but are not limited to, the following specific examples.
- Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes
- Candida fungi such as Candida albicans
- Aspergillus fungi such as Aspergillus fumigatus
- Cryptococcus fungi such as Cryptococcus neoformas, and the like.
- the compound of the present invention When applying the compound of the present invention as a plant disease and plant pest control agent, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, Antifreezing agents, binders, anti-caking agents, disintegrants, anti-degradants, etc. are added to prepare soluble concentrates, emulsifiable concentrates, wettable powders, water soluble powders, etc. ), water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, It can be put to practical use in any dosage form such as dustable powder, granule, gel and the like. In addition, from the viewpoint of saving labor and improving safety, the formulation of any dosage form described above can be enclosed in a water-soluble package and provided.
- solid carriers examples include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride and the like.
- natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride and the like.
- Inorganic salts, synthetic silicic acid, synthetic silicates and the like can be mentioned.
- liquid carriers examples include alcohols such as ethylene glycol, propylene glycol and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil; water; These solid and liquid carriers may be used alone or in combination of two or more.
- surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxyethylene Nonionic surfactants such as sorbitan fatty acid esters; alkyl sulfates, alkylbenzenesulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensate of naphthalenesulfonic acid , salts of formalin condensates of alkylnaphthalene sulfonic acids, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates,
- these surfactants are not particularly limited, it is usually desirable to be in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention. Moreover, these surfactants may be used alone or in combination of two or more.
- the compound of the present invention When the compound of the present invention is used as an agricultural chemical, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, It may be applied in combination with synergists, fertilizers, soil conditioners and the like.
- the types of pesticides used in combination with the compound of the present invention include, for example, the compounds described in The Pesticide Manual, 18th Edition, 2018. Specific examples of common names are as follows. However, pesticides used in combination are not necessarily limited to these. Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (benalaxyl-M), benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, benzovindiflupyr, binapacryl, biphenyl,
- Insecticides abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb ( aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethifos, azinphos-ethyl ), azinphos-methyl, azocyclotin, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate ( benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin , bistri
- Parasiticides esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox ( etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid ), nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvin
- Antifungal agents such as ketoconazole and miconazole nitrate.
- Antibiotics amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline chlortetracycline, clavulanic acid, danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin ( lomefloxacin, marbofloxacin, miloxacin, horramycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinics oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmico
- the amount of the compound of the present invention to be applied varies depending on the application scene, application time, application method, cultivated crops, etc., but in general, the appropriate amount of active ingredient is about 0.005 to 50 kg per hectare (ha). Yes, preferably 0.01 to 1 kg.
- [Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, an anti-caking agent and an anti-degradation agent.
- [Suspension agent] Compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts Others include, for example, antifreeze agents, thickeners and the like.
- Liquid carrier 20-99.99 parts Others 0-10 parts Others include, for example, antifreeze agents, spreading agents and the like.
- Compound of the present invention 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts Others include, for example, binders and antidegradants.
- the above formulation is diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, or sprayed without dilution.
- Emulsion Compound No. of the present invention Emulsion Compound No. of the present invention. 1-001 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) The above ingredients are uniformly mixed to form an emulsion. In use, the emulsion is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.
- Wettable Powder Compound No. of the present invention 1-001 25 parts Pyrophyllite 66 parts Solpol 5039 4 parts (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) Carplex #80D 3 copies (white carbon: manufactured by Shionogi & Co., Ltd., trade name) Calcium lignosulfonate 2 parts
- the above ingredients are uniformly mixed and pulverized to prepare a wettable powder.
- the wettable powder is diluted 50 to 20,000 times with water and sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
- Powder Compound No. of the present invention 1-001 3 parts Carplex #80D 0.5 parts (white carbon: manufactured by Shionogi & Co., Ltd., trade name) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to form powders. In use, the powder is sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
- Granules Compound No. of the present invention. 1-001 5 parts Bentonite 30 parts Talc 64 parts Calcium lignosulfonate 1 part Uniformly mix and pulverize the above ingredients, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry. Make granules. In use, the granules are sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
- the application method of the compound of the present invention includes foliage spraying, soil treatment, seed disinfection, etc., but general methods usually used by those skilled in the art are also effective.
- the present invention relates to the following [1] to [7].
- R 1 represents a hydrogen atom or 1 to C 6 alkyl
- R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 cycloalkoxycarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65; represent, G-1 to G-65 each represent a structure represented by the following structural formula,
- R 3 represents phenyl, phenyl substituted by (Z) m1 , F-31 or F-34;
- F-31 and F-34 represent structures represented by the following structural formulas,
- R 4 is —C ⁇ C—R 7 , C 1 -C 6 alkyl substituted by R 15 , C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, L- 1 to L-4, L-1 to L-6, L-8 and L-9 represent structures represented by the following structural formulas,
- R 5 represents C 1 -C 6 alkyl
- R b represents a hydrogen atom
- R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to representing E-90, L-5, L-6, L-8 or L-9
- R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10
- E-1 to E-90 each represent a structure represented by the following structural formula,
- R 10
- each Z 9 may be the same as or different from each other
- p3 represents an integer of 2 or 3
- p5 represents an integer of 2, 3, 4 or 5
- p6 represents an integer of 2
- 4 or 6 p7
- p8 represents an integer of 2
- 4, 5, 6 or 7, p8 represents an integer of 2
- 4, 5, 6, 7 or 8 p9 represents an integer of 2, 3, 4, 5, 6, 7,
- each Z 10 may be identical to each other or relative to each other.
- R 1 represents C 1 -C 6 alkyl
- R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, represents C 3 -C 6 cycloalkoxycarbonyl, —C(O)R 9 or phenyl
- R 3 represents phenyl or phenyl substituted by (Z) m1
- R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 , E-38, representing E-41, E-44, L-5 or L-6
- R 8 is C 3 -C 6 cycloalkyl, —C( ⁇ NOR 17 )R 18 , phen
- R 2 represents C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 ;
- R 4 represents C 1 -C 6 alkyl substituted by R 15 or L-1;
- R 6 represents E-38, E-44 or L-5;
- R 9 represents G-3, G-4, G-21 or G-22;
- R 18 represents C 1 -C 6 alkyl,
- R 2 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or phenyl;
- the thienouracil compound or a salt thereof according to [1] to [2] and [7] to [8] above.
- R 2 represents C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 , the above [1] to [3 ], the thienouracil compound or a salt thereof according to [7] to [8].
- R 2 represents C 1 -C 6 alkyl substituted by R 8
- R 8 is C 3 -C 6 cycloalkyl, —C( ⁇ NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-22, G-23 or G-53
- Z 1 represents a halogen atom
- m represents 1 or 2, the thienouracil compound or a salt thereof according to [10] above.
- R 2 represents —C(O)R 9 ;
- R 3 represents phenyl or phenyl substituted by (Z) m1 , Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
- R 4 is —C ⁇ C—R 7 , C 1 -C 6 alkyl substituted by R 15 , C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, L- 1 to L-3 or L-4, and R 15 represents C 1 to C 6 alkoxy, the thienouracil compound or a salt thereof according to the above [1], [7] to [35].
- R 4 represents —C ⁇ C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1, and R 15 represents C 1 -C 6 alkoxy, the above [1] to [ 2], the thienouracil compound or a salt thereof according to [7] to [35].
- R 4 represents C 1 -C 6 alkyl substituted by R 15 or L-1, and R 15 represents C 1 -C 6 alkoxy, the above [1] to [3], [7] to [ 35], the thienouracil compound or a salt thereof.
- R 4 represents C 1 -C 6 alkyl substituted by R 15 and R 15 represents C 1 -C 6 alkoxy A thienouracil compound or a salt thereof.
- R 4 represents C 1 alkyl substituted by R 15 , The thienouracil compound or salt thereof according to [40] above, wherein R 15 represents methoxy or ethoxy.
- R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5, above [1] to [2], [7] ⁇ Thienouracil compound or a salt thereof according to [45]
- R 6 represents C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5, above [1] to [3], [7] to [45] A thienouracil compound or a salt thereof as described.
- R 6 represents C 1 -C 6 alkyl substituted by R 11
- R 11 represents C 1 -C 6 alkylaminocarbonyl
- R 6 represents E-44
- Z a is C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl
- p9 represents 0.
- m and m1 represent an integer of 1 or 2
- p2 represents an integer of 0 or 1
- p3 represents an integer of 0 or 1
- p4 represents an integer of 0 or 1
- p8 represents 0,
- p9 represents 0,
- R 1 represents a hydrogen atom or 1 - C6 alkyl
- R 2 is a hydrogen atom, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or represents G-1 to G-65
- R 3 represents phenyl or phenyl substituted by (Z) m1
- R 4 represents -C ⁇ C-R 7 or L-1
- R 5 represents C 1 -C 6 alkyl
- R b represents a hydrogen atom
- R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 or E-1 to E-90
- R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)
- each Z 10 may be different from each other,
- p3 represents an integer of 2 or 3
- p5 represents an integer of 2, 3, 4 or 5
- p6 represents an integer of 2
- p7 is p8 represents an integer of 2, 3
- 4, 5, 6 or 7, p8 represents an integer of 2, 3
- p9 represents an integer of 2, 3, 4, 5, 6, 7,
- each Z 10 may be identical to each other or relative to each other.
- r represents an integer of 0, 1 or 2
- p1 represents an integer of 0 or 1
- p2 represents an integer of 0, 1 or 2
- p3 represents an integer of 0, 1, 2 or 3
- p4 represents an integer of 0, 1, 2, 3 or 4
- p5
- R 1 represents C 1 -C 6 alkyl
- R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 represents R 3 represents phenyl substituted by (Z) m1 , R 6 represents C 1 -C 6 alkyl or E-38; R 9 represents C 1 -C 6 alkylcarbonyl, phenyl, G-3, G-21 or G-22; Z represents a halogen atom or C 1 -C 6 alkoxy; The thienouracil compound or salt thereof according to [63] above, wherein Z 1 represents a halogen atom.
- m represents an integer of 1
- m1 represents an integer of 1 or 2
- R 1 represents a hydrogen atom or C 1 -C 6 alkyl
- R 2 is a hydrogen atom, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65
- R 3 represents phenyl, phenyl substituted by (Z) m1 , F-31 or F-34
- R 4 represents —C ⁇ C—R 7 , C 1 to C 6 alkyl substituted by R 15 or L-1 to L-4
- R 5 represents C 1 -C 6 alkyl
- R b represents a hydrogen atom
- R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl substitute
- each Z 9 may be the same as or different from each other
- p3 represents an integer of 2 or 3
- p5 represents an integer of 2, 3, 4 or 5
- p6 represents an integer of 2
- 4 or 6 p7
- p8 represents an integer of 2
- 4, 5, 6 or 7, p8 represents an integer of 2
- 4, 5, 6, 7 or 8 p9 represents an integer of 2, 3, 4, 5, 6, 7,
- each Z 10 may be identical to each other or relative to each other.
- r represents an integer of 0, 1 or 2
- p1 represents an integer of 0 or 1
- p2 represents an integer of 0, 1 or 2
- p3 represents an integer of 0, 1, 2 or 3
- p4 represents an integer of 0, 1, 2, 3 or 4
- p5
- R 1 represents C 1 -C 6 alkyl
- R 4 represents —C ⁇ C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1
- R 6 represents C 1 -C 6 alkyl or E-38
- R 9 represents C 1 -C 6 alkylcarbonyl, phenyl, G-3, G-21 or G-22
- R 15 represents C 1 -C 6 alkoxy
- R a1 represents C 1
- m represents an integer of 1
- m1 represents an integer of 1 or 2
- An antifungal agent containing, as an active ingredient, one or more selected from the thienouracil compounds and salts thereof according to any one of [1] to [70] above.
- An internal parasite control agent containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of [1] to [70] above.
- reaction solution was heated to 70° C., and a solution of 190 mg of tetrahydro-2H-pyran-4-yl-4-methylbenzenesulfonate in 1 ml of 1,3-dimethyl-2-imidazolidinone was added dropwise. Stirred for an hour. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dissolved in 5 ml of chloroform, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
- the resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as an eluent (numbers are volume ratios, the same applies hereinafter), 85 mg of the desired product was obtained as an oily substance.
- Reference example 7 1-(2-(3-chlorophenyl)-2-oxoethyl)-N-(2-mercaptoethyl)-5-methyl-3-(methylamino)-2,4-dioxo-1,2,3,4- Synthesis of Tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide N-(2-chloroethyl)-1-(2-(3-chlorophenyl)-2-oxoethyl)-5-methyl-3-(methylamino) 117 mg of thiourea was added to a solution of 360 mg of -2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide in 5 ml of ethanol at room temperature.
- Reference example 8 1-(2-(3-chlorophenyl)-2-oxoethyl)-6-(4,5-dihydrothiazole-2yl)-5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2 ,4-(1H,3H)-dione synthesis 1-(2-(3-chlorophenyl)-2-oxoethyl)-N-(2-mercaptoethyl)-5-methyl-3-(methylamino)-2, To a solution of 260 mg of 4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide in 50 ml of toluene, 215 mg of p-toluenesulfonic acid monohydrate was added at room temperature.
- the compound of the present invention can be synthesized according to the above Production Examples and Synthesis Examples. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 5 are shown in Tables 3 to 6, but the compounds of the present invention are not limited to these. In addition, for all synthetic compounds described in Tables 3 to 6, based on the results of structural analysis of Synthesis Example 1 of International Publication No. 2021/149771, the stereoscopic compounds described in Tables 3 to 6 A single geometric isomer with configuration was assumed to be obtained.
- Me is methyl
- Et is ethyl
- nPr is normal propyl
- iPr isopropyl
- cPr is cyclopropyl
- iBu is isobutyl
- sBu is secondary butyl
- tBu is tertiary butyl
- nPen is n-pentyl
- cPen for cyclopentyl cHex for cyclohexyl
- Ph for phenyl, for a double bond
- ⁇ a triple bond.
- the notation "*" indicates that the compound is an oily or resinous compound with no melting point
- mp indicates the melting point (unit: °C).
- the substituents represented by E-41a, E-44a, E-45a and E-76a each represent the following structures.
- substituents represented by L-2, L-3, L-4, L-5a, L-5b, L-5c, L-6a and L-7a each represent the following structures.
- 3-027 ⁇ 7.73-7.64 (m, 1H), 7.52-6.81 (m, 5H), 5.76-5.25 (m, 1H), 4.63-4.47 (m, 2H), 4.34-4.07 (m, 1H) , 3.90-3.79 (m, 4H), 3.54-3.32 (m, 6H), 2.87-2.45 (m, 6H), 1.33-1.10 (m, 3H).
- 3-028 ⁇ 7.40-6.74 (m, 5H), 6.14-5.78 (m, 1H), 4.63-4.43 (m, 2H), 4.03-2.89 (m, 17H), 2.57-2.39 (m, 6H) , 1.72-1.21 (m, 4H).
- 3-062 ⁇ 7.64-6.75 (m, 7H), 6.18-5.92 (m, 1H), 4.60-4.42 (m, 2H), 4.18-3.88 (m, 1H), 3.76-2.79 (m, 13H) , 2.57-2.40 (m, 6H), 1.81-1.20 (m, 4H).
- 3-064 ⁇ 7.64-6.75 (m, 7H), 6.19-5.95 (m, 1H), 4.60-4.42 (m, 2H), 4.17-3.91 (m, 1H), 3.78-3.58 (m, 2H) , 3.46-3.10 (m, 8H), 2.57-2.39 (m, 6H), 1.89-1.33 (m, 4H).
- 3-070 ⁇ 7.62-7.39 (m, 5H), 6.13-5.96 (m, 1H), 4.59-4.45 (m, 2H), 4.10-2.93 (m, 17H), 2.54-2.40 (m, 3H) , 2.13-1.97 (m, 3H), 1.82-1.40 (m, 4H).
- 3-072 ⁇ 7.62-7.52 (m, 2H), 7.51-7.40 (m, 3H), 6.15-5.97 (m, 1H), 4.61-4.45 (m, 2H), 4.10-3.21 (m, 14H) , 2.54-2.40 (m, 3H), 2.13-1.97 (m, 3H), 1.86-1.47 (m, 4H).
- 3-091 ⁇ 7.54-6.79 (m, 6H), 6.04-5.71 (m, 1H), 4.60-4.44 (m, 2H), 4.03-3.81 (m, 4H), 3.75-3.57 (m, 2H) , 3.45-3.15 (m, 8H), 2.59-2.39 (m, 6H), 1.79-1.16 (m, 4H).
- 3-092 ⁇ 7.55-6.76 (m, 6H), 6.02-5.68 (m, 1H), 4.63-4.45 (m, 2H), 4.04-2.91 (m, 17H), 2.61-2.39 (m, 6H) , 1.69-1.13 (m, 4H).
- 3-093 ⁇ 7.62-7.06 (m, 6H), 6.59-6.40 (m, 1H), 6.23-6.00 (m, 1H), 4.60-4.46 (m, 2H), 4.04-3.91 (m, 1H) , 3.81-3.14 (m, 10H), 2.53-2.41 (m, 3H), 1.87-1.47 (m, 4H).
- 3-094 ⁇ 8.73-7.20 (m, 8H), 6.26-6.03 (m, 1H), 4.61-4.43 (m, 2H), 4.11-3.91 (m, 1H), 3.79-3.17 (m, 10H) , 2.53-2.37 (m, 3H), 1.88-1.20 (m, 4H).
- 3-135 ⁇ 7.25-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.85 (m, 1H), 4.60-4.44 (m, 2H), 4.05-2.97 (m, 16H) , 2.53-1.92 (m, 10H), 1.81-1.55 (m, 4H).
- 3-136 ⁇ 8.15-6.90 (m, 9H), 6.00-5.65 (m, 1H), 4.57-4.38 (m, 2H), 4.05-3.13 (m, 14H), 2.55-2.35 (m, 3H) , 1.82-1.30 (m, 4H).
- 4-006 ⁇ 7.80-6.80 (m, 6H), 6.00-5.20 (m, 2H), 3.90-3.20 (m, 15H), 2.50-2.40 (m, 3H), 1.80-1.50 (m, 4H) .
- Test Drug Solution A compound of the present invention according to one embodiment was added to an emulsified white sample (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry Co., Ltd.), N-methylpyrrolidone, and Solvesso (registered trademark) 200 (manufactured by ExxonMobil) [ 1:5:28 (weight ratio)] to prepare emulsions with a concentration of 1% by mass, 5% by mass or 20% by mass.This emulsion is used as a test drug solution in Test Examples 1 to 9 below. tried.
- Solpol registered trademark
- 3005XL manufactured by Toho Chemical Industry Co., Ltd.
- N-methylpyrrolidone N-methylpyrrolidone
- Solvesso (registered trademark) 200 manufactured by ExxonMobil
- Test Example 1 Wheat wilt disease control effect test Plant wheat (cultivar: Haruyutaka) in a 90 cm 3 plastic pot, and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water at the 1.3 leaf stage. processed.
- the wheat was spray-inoculated with a conidial spore suspension of Septoria nodorum and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature 20° C., humidity 80% RH) and held for 8 days.
- the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated according to the following formula.
- Control value [1-(lesion area rate in treated area/lesion area rate in untreated area)] x 100
- the following compounds showed a control value of 70% or more.
- Test Example 2 Wheat leaf rust prevention effect test Wheat (variety: Norin No. 61) was planted in a 90 cm 3 plastic pot, and at the 1.3 leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was added. Treated by spraying. One day after spraying, wheat was spray-inoculated with a spore suspension of Puccinia recondita and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 1 day. After that, it was placed in an air-conditioned greenhouse (temperature 20° C., humidity 60% RH) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
- Test Example 3 Wheat Powdery Mildew Control Effect Test Wheat (variety: Norin No. 61) was planted in a 90 cm 3 plastic pot, and at the 1.3 leaf stage, the test chemical was diluted with water to 500 ppm. 5 ml was sprayed. One day after spraying, the wheat was placed in an air-conditioned greenhouse (temperature 20° C., humidity 70% RH) and inoculated with conidia of wheat powdery mildew (Blumeria graminis). Thereafter, the leaves were maintained for 7 days, and the ratio of the formed lesions to the inoculated leaves was measured.
- Test Example 4 Tomato Powdery Mildew Control Effect Test Tomatoes (variety: Momotaro) were planted in a 90 cm 3 plastic pot, and at the two-leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was sprayed. . After air-drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying a conidia suspension of tomato powdery mildew (Leveillula taurica). After leaving for 14 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
- Test Example 5 Cucumber gray mold control effect test A cucumber (cultivar: Frost-free ground) is planted in a 90 cm 3 plastic pot, and 5 ml of a chemical solution prepared by diluting the test chemical solution with water to 500 ppm is sprayed during the cotyledon stage. Treated and air dried. The treated leaves were then cut and placed in a plastic container. A conidia suspension of Botrytis cinerea and dissolved PDA medium were mixed at a ratio of 1:1 (volume ratio), and 30 ⁇ l of the mixture was inoculated dropwise onto the treated leaves. After inoculation, the plants were placed at 20° C. and high humidity (100% RH) for 3 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
- Test Example 6 Cucumber Sclerotinia Prevention Effect Test Plant cucumbers (variety: frost-free ground) in a 90 cm 3 plastic pot, and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water during the cotyledon stage. and air dried. The treated leaves were then placed in a plastic container. Sclerotinia sclerotiorum-containing agar pieces (5 mm in diameter) previously cultured in PDA medium were inoculated onto the drug-treated cucumber cotyledons. After inoculation, the plastic container was covered with vinyl, humidified (humidity 100% RH), and placed at 20° C. for 2 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
- Test Example 7 Cucumber Powdery Mildew Control Effect Test Plant cucumbers (cultivar: Frost-free ground) in a plastic pot of 90 cm 3 , and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water during the cotyledon stage. processed. After air-drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying with a conidia suspension of cucumber powdery mildew (Erysiphe polygoni). After leaving for 9 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
- Test Example 8 Cucumber anthracnose control effect test A cucumber (cultivar: Frost-free ground) is planted in a 90 cm 3 plastic pot, and at the cotyledon stage, 5 ml of a chemical solution prepared by diluting the test chemical solution with water to 500 ppm is sprayed. did.
- cucumbers were spray-inoculated with a conidial spore suspension of Colletotrichum lagenarium and placed in an inoculation box at a temperature of 25° C. and a humidity of 100% RH for 2 days. Then, it was placed in an air-conditioned greenhouse (temperature 23° C., humidity 60% RH) and held for 7 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
- Test Example 9 Soybean Rust Prevention Effect Test Soybeans (variety: Enrei) were planted in a 90 cm 3 plastic pot, and at the single leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was sprayed. One day after spraying, the soybeans were spray-inoculated with a conidia suspension of Phakopsora pachyrhizi and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature: 20°C, humidity: 60% RH) and held for 10 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
- test drug solutions were prepared by the following method. First, a compound of the present invention according to one aspect was dissolved in dimethylsulfoxide to prepare a 1% concentration solution. Distilled water was then added to dilute to a given concentration (10 ppm).
- Test Example 11 Antibacterial activity test against Candida albicans
- 10 ⁇ l of the test drug solution of the compound of the present invention according to one aspect was added to each well, and Candida albicans culture supernatant (5 ⁇ 10 3 cells/ml) was added thereon.
- Potato dextrose was added in 90 ⁇ l portions. Plates were left at 25° C. in the dark. Two days after addition of the drug, the bacterial flora area ratio (%) was determined, and the efficiency (%) relative to the untreated plot was calculated by the following formula.
- Efficacy (%) [1-(treated area bacterial flora area / untreated area bacterial flora area ratio)] ⁇ 100 As a result, among the tested compounds, the following compounds showed an efficiency (%) of 70% or more.
- the thienouracil compound according to the present invention is an extremely useful compound that exhibits excellent pesticidal activity, particularly fungicidal activity, and has almost no adverse effects on non-target organisms such as mammals, fish, and useful insects. be.
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Abstract
The purpose of the present invention is to provide a novel bactericidal agent, particularly a bactericidal agent for agricultural or horticultural use. Provided is a thienouracil compound represented by formula (1): [wherein R1 represents a C1-C6 alkyl group or the like; R2 represents -C(O)R9 or the like; R3 represents a phenyl group substituted by (Z)m1, or the like; R4 represents -C≡C-R7 or the like; R5 represents a C1-C6 alkyl group; R9 represents a phenyl group or the like; R6 represents a C1-C6 alkyl group or the like; Rb represents a hydrogen atom; Z represents a C1-C6 alkoxy group or the like; and m1 represents an integer of 1 to 5] or a salt thereof.
Description
本発明は新規なチエノウラシル化合物及びそれらの塩、並びに該化合物及びその塩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。
The present invention relates to novel thienouracil compounds and salts thereof, and pest control agents containing the compounds and salts thereof as active ingredients.
ある種のチエノウラシル化合物は殺菌活性を有することが知られている(例えば、特許文献1~特許文献11参照)。
Certain thienouracil compounds are known to have bactericidal activity (see, for example, Patent Documents 1 to 11).
しかしながら、薬剤の長年にわたる使用は、病原菌における薬剤抵抗性獲得を引き起こし得る。そのため、優れた防除効果を有する新規な薬剤の開発が常に期待されている。
However, long-term use of drugs can cause the acquisition of drug resistance in pathogenic bacteria. Therefore, the development of novel agents with excellent control effects is always expected.
本発明者らは、上記の課題解決を目標に鋭意研究を重ねた結果、本発明に係る下記式(1)で表される新規なチエノウラシル化合物が、殺菌剤、特に農園芸用殺菌剤として優れた防除活性を示すことを見い出し、本発明を完成した。
The present inventors have made intensive studies with the goal of solving the above problems, and as a result, the novel thienouracil compound represented by the following formula (1) according to the present invention is excellent as a fungicide, especially as an agricultural and horticultural fungicide. The present invention was completed based on the discovery that the pest control activity was
本発明に係るチエノウラシル化合物に関しては何れの文献にも開示されておらず、また、それらの有害生物防除剤としての有用性は知られていない。
The thienouracil compounds according to the present invention are not disclosed in any literature, and their usefulness as pest control agents is unknown.
すなわち、本発明は下記〔1〕に関するものである。
That is, the present invention relates to the following [1].
[式中、R1は、水素原子又はC1~C6アルキルを表し、
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-C(O)R9、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
G-1~G-65は、それぞれ下記の構造式で表される構造を表し、
[In the formula, R 1 represents a hydrogen atom or C 1 to C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 cycloalkoxycarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65; represent,
G-1 to G-65 each represent a structure represented by the following structural formula,
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-C(O)R9、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
G-1~G-65は、それぞれ下記の構造式で表される構造を表し、
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 cycloalkoxycarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65; represent,
G-1 to G-65 each represent a structure represented by the following structural formula,
F-31及びF-34は、下記の構造式で表される構造を表し、
F-31 and F-34 represent structures represented by the following structural formulas,
L-1~L-6、L-8及びL-9は、下記の構造式で表される構造を表し、
L-1 to L-6, L-8 and L-9 represent structures represented by the following structural formulas,
R5は、C1~C6アルキルを表し、
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル又はE-1~E-90、L-5、L-6、L-8又はL-9を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
E-1~E-90は、それぞれ下記の構造式で表される構造を表し、
R 5 represents C 1 -C 6 alkyl,
R b represents a hydrogen atom,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to representing E-90, L-5, L-6, L-8 or L-9,
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
E-1 to E-90 each represent a structure represented by the following structural formula,
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル又はE-1~E-90、L-5、L-6、L-8又はL-9を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
E-1~E-90は、それぞれ下記の構造式で表される構造を表し、
R b represents a hydrogen atom,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to representing E-90, L-5, L-6, L-8 or L-9,
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
E-1 to E-90 each represent a structure represented by the following structural formula,
R8は、C1~C6アルコキシ、C3~C6シクロアルキル、-C(=NOR17)R18、-C(=NNR13R14)Ra1、-C(=NCN)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、C1~C6アルキルアミノ、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル、G-1~G-65、E-1~E-89又はE-90を表し、
R10は、フェニルを表し、
R11は、-OH、C1~C6アルコキシ、C1~C6アルキルアミノカルボニル、-C(O)N(ORa)Ra2、E-3、E-6、E-7又はE-38を表し、
R12は、水素原子又はC1~C6アルキルを表し、
R13は、水素原子又はC1~C6アルキルを表し、
R14は、C1~C6アルキル又はC1~C6アルキルカルボニルを表し、
R15は、シアノ、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルキル、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R17は、水素原子、C1~C6アルキル又は-CH2C(O)Raを表し、
R18は、水素原子、C1~C6アルキル又はフェニルを表し、
Raは、C1~C6アルキルを表し、
Ra1は、水素原子、C1~C6アルキル、フェニル又は(Z1)mによって置換されたフェニルを表し、
Ra2は、C1~C6アルキルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、又は互いに相異なっても良く、
Z1は、シアノ、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、又は互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、シアノ、C1~C6アルキル、C1~C6アルコキシ、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-CH2CN又は-C(O)C(O)ORaを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を表し、p5が2、3、4又は5の整数を表し、p7が2、3、4、5、6又は7の整数を表す場合には、各々のZ9は互いに同一であっても、又は互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、又は互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表されるチエノウラシル化合物又はその塩。 R 8 is C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, —C(=NOR 17 )R 18 , —C(=NNR 13 R 14 )R a1 , —C(=NCN)R a1 , represents phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkyl amino, di(C 1 -C 6 alkyl)amino, —C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m , G-1 to G-65, E-1 to E- 89 or E-90,
R 10 represents phenyl,
R 11 is —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylaminocarbonyl, —C(O)N(OR a )R a2 , E-3, E-6, E-7 or E- represents 38,
R 12 represents a hydrogen atom or C 1 -C 6 alkyl,
R 13 represents a hydrogen atom or C 1 -C 6 alkyl,
R 14 represents C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl,
R 15 represents cyano, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 17 represents a hydrogen atom, C 1 -C 6 alkyl or —CH 2 C(O)R a ,
R 18 represents a hydrogen atom, C 1 -C 6 alkyl or phenyl;
R a represents C 1 -C 6 alkyl,
R a1 represents a hydrogen atom, C 1 -C 6 alkyl, phenyl or phenyl substituted by (Z 1 ) m ;
R a2 represents C 1 -C 6 alkyl,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents cyano, a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a is cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 6 alkyl)aminocarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —CH CN or —C ( O)C(O)OR a ,
In relation to Z9, p2 represents an integer of 2, p3 represents an integer of 2 or 3, p4 represents an integer of 2, 3 or 4, and p5 represents an integer of 2, 3, 4 or 5. and when p represents an integer of 2, 3, 4, 5, 6 or 7, each Z 9 may be the same as or different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
A thienouracil compound represented by or a salt thereof.
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、C1~C6アルキルアミノ、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル、G-1~G-65、E-1~E-89又はE-90を表し、
R10は、フェニルを表し、
R11は、-OH、C1~C6アルコキシ、C1~C6アルキルアミノカルボニル、-C(O)N(ORa)Ra2、E-3、E-6、E-7又はE-38を表し、
R12は、水素原子又はC1~C6アルキルを表し、
R13は、水素原子又はC1~C6アルキルを表し、
R14は、C1~C6アルキル又はC1~C6アルキルカルボニルを表し、
R15は、シアノ、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルキル、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R17は、水素原子、C1~C6アルキル又は-CH2C(O)Raを表し、
R18は、水素原子、C1~C6アルキル又はフェニルを表し、
Raは、C1~C6アルキルを表し、
Ra1は、水素原子、C1~C6アルキル、フェニル又は(Z1)mによって置換されたフェニルを表し、
Ra2は、C1~C6アルキルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、又は互いに相異なっても良く、
Z1は、シアノ、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、又は互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、シアノ、C1~C6アルキル、C1~C6アルコキシ、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-CH2CN又は-C(O)C(O)ORaを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を表し、p5が2、3、4又は5の整数を表し、p7が2、3、4、5、6又は7の整数を表す場合には、各々のZ9は互いに同一であっても、又は互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、又は互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表されるチエノウラシル化合物又はその塩。 R 8 is C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, —C(=NOR 17 )R 18 , —C(=NNR 13 R 14 )R a1 , —C(=NCN)R a1 , represents phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkyl amino, di(C 1 -C 6 alkyl)amino, —C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m , G-1 to G-65, E-1 to E- 89 or E-90,
R 10 represents phenyl,
R 11 is —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylaminocarbonyl, —C(O)N(OR a )R a2 , E-3, E-6, E-7 or E- represents 38,
R 12 represents a hydrogen atom or C 1 -C 6 alkyl,
R 13 represents a hydrogen atom or C 1 -C 6 alkyl,
R 14 represents C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl,
R 15 represents cyano, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 17 represents a hydrogen atom, C 1 -C 6 alkyl or —CH 2 C(O)R a ,
R 18 represents a hydrogen atom, C 1 -C 6 alkyl or phenyl;
R a represents C 1 -C 6 alkyl,
R a1 represents a hydrogen atom, C 1 -C 6 alkyl, phenyl or phenyl substituted by (Z 1 ) m ;
R a2 represents C 1 -C 6 alkyl,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents cyano, a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a is cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 6 alkyl)aminocarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —CH CN or —C ( O)C(O)OR a ,
In relation to Z9, p2 represents an integer of 2, p3 represents an integer of 2 or 3, p4 represents an integer of 2, 3 or 4, and p5 represents an integer of 2, 3, 4 or 5. and when p represents an integer of 2, 3, 4, 5, 6 or 7, each Z 9 may be the same as or different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
A thienouracil compound represented by or a salt thereof.
本発明化合物は多くの病原菌に対して優れた防除活性を発揮する。
The compound of the present invention exhibits excellent control activity against many pathogenic bacteria.
従って、本発明は有用な殺菌剤、特に農園芸用殺菌剤を提供することができる。
Therefore, the present invention can provide useful fungicides, especially agricultural and horticultural fungicides.
以下、本発明について詳細に説明する。
The present invention will be described in detail below.
本発明化合物であるチエノウラシル化合物には、ウラシル環上に置換されたアルケニル基の存在に基づく2種類の立体配置を有する幾何異性体、つまり式(1a)で表される化合物及び式(1b)で表される化合物が存在する。本発明はこれら式(1a)で表される化合物、式(1b)で表される化合物、又は式(1a)で表される化合物及び式(1b)で表される化合物を任意の割合で含む混合物を包含するものである。
The thienouracil compound, which is the compound of the present invention, has two types of geometric isomers based on the presence of alkenyl groups substituted on the uracil ring, that is, the compound represented by formula (1a) and the compound represented by formula (1b). The represented compound exists. The present invention includes the compound represented by the formula (1a), the compound represented by the formula (1b), or the compound represented by the formula (1a) and the compound represented by the formula (1b) in an arbitrary ratio. It includes mixtures.
本発明化合物には、置換基の種類によってはE-体及びZ-体の幾何異性体が存在する場合があるが、本発明はこれらE-体、Z-体又はE-体及びZ-体を任意の割合で含む混合物を包含するものである。
The compounds of the present invention may have E- and Z-form geometric isomers depending on the type of substituents. in any proportion.
また、本発明化合物は、1個又は2個以上の不斉炭素原子又は不斉硫黄原子の存在に起因する光学活性体が存在場合があるが、本発明は全ての光学活性体又はラセミ体を包含するものである。
In addition, the compounds of the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, but the present invention includes all optically active forms and racemic forms. It includes.
また、本発明化合物には、置換基の種類によって互変異性体が存在する場合があるが、本発明は全ての互変異性体又は任意の割合で含む互変異性体の混合物を包含するものである。
In addition, the compound of the present invention may have tautomers depending on the type of substituent, but the present invention includes all tautomers or mixtures of tautomers in any ratio. is.
また、本発明化合物は、置換基同士の立体障害を原因とする制限された結合回転により、1種又は2種以上の回転異性体として存在する場合があるが、本発明は全ての回転異性体又は任意の割合で含むジアステレオマーの混合物を包含するものである。
In addition, the compounds of the present invention may exist as one or more rotamers due to restricted bond rotation caused by steric hindrance between substituents. or mixtures of diastereomers in any proportion.
また、本発明化合物には、複素環基上の環を構成する窒素原子が酸素原子により酸化され得る複素環を持つものが存在する(例えば、ピリジン環等)が、本発明はそれらの酸化体を包含するものである。
In addition, some compounds of the present invention have a heterocyclic ring in which the nitrogen atom constituting the ring on the heterocyclic group can be oxidized by an oxygen atom (e.g., pyridine ring, etc.). It includes
本発明化合物のうちで、常法に従って塩にすることができるものは、例えば、フッ化水素酸、塩酸、臭化水素酸、ヨウ化水素酸等のハロゲン化水素酸の塩、硝酸、硫酸、燐酸、塩素酸、過塩素酸等の無機酸の塩、メタンスルホン酸、エタンスルホン酸、トリフルオロメタンスルホン酸、ベンゼンスルホン酸、p-トルエンスルホン酸等のスルホン酸の塩、ギ酸、酢酸、プロピオン酸、トリフルオロ酢酸、フマール酸、酒石酸、蓚酸、マレイン酸、リンゴ酸、コハク酸、安息香酸、マンデル酸、アスコルビン酸、乳酸、グルコン酸、クエン酸等のカルボン酸の塩、グルタミン酸、アスパラギン酸等のアミノ酸の塩、リチウム、ナトリウム、カリウムといったアルカリ金属の塩、カルシウム、バリウム、マグネシウム等のアルカリ土類金属の塩、アルミニウムの塩、テトラメチルアンモニウム塩、テトラブチルアンモニウム塩、ベンジルトリメチルアンモニウム塩等の四級アンモニウム塩とすることができる。
Among the compounds of the present invention, those that can be converted into salts by conventional methods include, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, nitric acid, sulfuric acid, Salts of inorganic acids such as phosphoric acid, chloric acid and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid; formic acid, acetic acid, propionic acid , trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, salts of carboxylic acids such as citric acid, glutamic acid, aspartic acid, etc. Amino acid salts, alkali metal salts such as lithium, sodium and potassium, alkaline earth metal salts such as calcium, barium and magnesium, aluminum salts, tetramethylammonium salts, tetrabutylammonium salts, benzyltrimethylammonium salts, etc. Ammonium salts can be used.
次に、本明細書において示した各置換基の具体例を以下に示す。ここで、n-はノルマル、i-はイソ、s-はセカンダリー、tert-はターシャリーを各々意味し、Phはフェニルを意味する。
Next, specific examples of each substituent shown in this specification are shown below. Here, n- means normal, i- means iso, s- means secondary, tert- means tertiary, and Ph means phenyl.
本明細書における「ハロゲン原子」としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。なお、本明細書中「ハロ」の表記もこれらのハロゲン原子を表す。
"Halogen atoms" in the present specification include fluorine atoms, chlorine atoms, bromine atoms and iodine atoms. In addition, the notation of "halo" also represents these halogen atoms in this specification.
本明細書における「Ca~Cbアルキル」の表記は、炭素原子数がa~b個よりなる直鎖状又は分岐鎖状の飽和炭化水素基を表し、例えばメチル、エチル、n-プロピル、i-プロピル、n-ブチル、i-ブチル、s-ブチル、tert-ブチル、n-ペンチル、1,1-ジメチルプロピル、n-ヘキシル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation "C a -C b alkyl" as used herein represents a linear or branched saturated hydrocarbon group having a to b carbon atoms, such as methyl, ethyl, n-propyl, Specific examples include i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, n-hexyl and the like. Selected by range.
本明細書における「Ca~Cbアルケニル」の表記は、炭素原子数がa~b個よりなる直鎖状又は分岐鎖状で、且つ分子内に1個又は2個以上の二重結合を有する不飽和炭化水素基を表し、例えばビニル、1-プロペニル、2-プロペニル、1-メチルエテニル、2-ブテニル、2-メチル-2-プロペニル、3-メチル-2-ブテニル、1,1-ジメチル-2-プロペニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b alkenyl" as used herein means a linear or branched chain consisting of a to b carbon atoms and having one or more double bonds in the molecule. represents an unsaturated hydrocarbon group having a Specific examples include 2-propenyl and the like, and are selected within the specified range of the number of carbon atoms.
本明細書における「Ca~Cbハロアルケニル」の表記は、炭素原子に結合した水素原子がハロゲン原子によって任意に置換された、炭素原子数がa~b個よりなる直鎖状又は分岐鎖状で、且つ分子内に1個又は2個以上の二重結合を有する不飽和炭化水素基を表し、例えば1-クロロ-1-プロペニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation "C a -C b haloalkenyl" used herein means a linear or branched chain having a to b carbon atoms in which hydrogen atoms bonded to carbon atoms are optionally substituted with halogen atoms. and represents an unsaturated hydrocarbon group having one or more double bonds in the molecule, and specific examples thereof include 1-chloro-1-propenyl, etc., and is selected in the range of
本明細書における「Ca~Cbアルコキシ」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-O-基を表し、例えばメトキシ、エトキシ、n-プロピルオキシ、i-プロピルオキシ、n-ブチルオキシ、i-ブチルオキシ、s-ブチルオキシ、tert-ブチルオキシ、2-エチルへキシルオキシ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation "C a -C b alkoxy" as used herein represents an alkyl-O- group having a to b carbon atoms as defined above, such as methoxy, ethoxy, n-propyloxy, i Specific examples include -propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, etc., and are selected within the designated number of carbon atoms.
本明細書における「Ca~Cbシクロアルキル」の表記は、炭素原子数がa~b個よりなる環状の炭化水素基を表し、3員環から10員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキルによって任意に置換されていてもよい。例えばシクロプロピル、1-メチルシクロプロピル、2-メチルシクロプロピル、2,2-ジメチルシクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b cycloalkyl" in this specification represents a cyclic hydrocarbon group having a to b carbon atoms, and has a 3- to 10-membered monocyclic or composite ring structure. can be formed. Each ring may also be optionally substituted with alkyl within the specified number of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., and each is selected within the designated number of carbon atoms. .
本明細書における「Ca~Cbアルキルカルボニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-C(O)-基を表し、例えばアセチル、プロピオニル、ブチリル、イソブチリル、バレリル、イソバレリル、2-メチルブタノイル、ピバロイル、ヘキサノイル、ヘプタノイル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b alkylcarbonyl" as used herein means an alkyl-C(O)- group having a to b carbon atoms as defined above, such as acetyl, propionyl, butyryl, Specific examples include isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, heptanoyl and the like, and each is selected within the specified number of carbon atoms.
本明細書における「Ca~Cbアルコキシカルボニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-O-C(O)-基を表し、例えばメトキシカルボニル、エトキシカルボニル、n-プロピルオキシカルボニル、i-プロピルオキシカルボニル、n-ブトキシカルボニル、i-ブトキシカルボニル、s-ブトキシカルボニル、tert-ブトキシカルボニル、2-エチルへキシルオキシカルボニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b alkoxycarbonyl" in this specification represents an alkyl-O-C(O)- group having a to b carbon atoms as defined above, such as methoxycarbonyl, ethoxy Specific examples include carbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl and the like. is selected within the specified number of carbon atoms.
本明細書における「Ca~Cbシクロアルコキシカルボニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるシクロアルキル-O-C(O)-基を表し、例えばシクロプロピルオキシカルボニル、シクロへキシルオキシカルボニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b cycloalkoxycarbonyl" as used herein represents a cycloalkyl-O-C(O)- group having a to b carbon atoms as defined above, such as cyclopropyl Specific examples include oxycarbonyl, cyclohexyloxycarbonyl, and the like, and are selected within the specified range of the number of carbon atoms.
本明細書における「Ca~Cbアルキルチオ」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-S-基を表し、例えばメチルチオ、エチルチオ、n-プロピルチオ、i-プロピルチオ、n-ブチルチオ、i-ブチルチオ、s-ブチルチオ、tert-ブチルチオ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b alkylthio" in the present specification represents an alkyl-S-group having a to b carbon atoms as defined above, such as methylthio, ethylthio, n-propylthio, i- Specific examples include propylthio, n-butylthio, i-butylthio, s-butylthio, tert-butylthio and the like, each selected within the specified number of carbon atoms.
本明細書における「Ca~Cbアルキルスルフィニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-S(O)-基を表し、例えばメチルスルフィニル、エチルスルフィニル、n-プロピルスルフィニル、i-プロピルスルフィニル、n-ブチルスルフィニル、i-ブチルスルフィニル、S-ブチルスルフィニル、tert-ブチルスルフィニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b alkylsulfinyl" in this specification represents the above-described alkyl-S(O)-group having a to b carbon atoms, such as methylsulfinyl, ethylsulfinyl, Specific examples include n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, tert-butylsulfinyl and the like, and each is selected within the designated number of carbon atoms. .
本明細書における「Ca~Cbアルキルスルホニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-SO2-基を表し、例えばメチルスルホニル、エチルスルホニル、n-プロピルスルホニル、i-プロピルスルホニル、n-ブチルスルホニル、i-ブチルスルホニル、s-ブチルスルホニル、tert-ブチルスルホニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b alkylsulfonyl" as used herein means an alkyl-SO 2 - group having a to b carbon atoms as defined above, such as methylsulfonyl, ethylsulfonyl, n- Specific examples include propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl and the like, and each is selected within the specified number of carbon atoms.
本明細書における「Ca~Cbアルキルアミノ」の表記は、水素原子の一方が炭素原子数がa~b個よりなる前記の意味であるアルキルによって置換されたアミノ基を表し、例えば、メチルアミノ、エチルアミノ、n-プロピルアミノ、i-プロピルアミノ、n-ブチルアミノ、i-ブチルアミノ、tert-ブチルアミノ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation "C a -C b alkylamino" as used herein refers to an amino group in which one of the hydrogen atoms is substituted by the aforementioned alkyl having a to b carbon atoms, for example, methyl Specific examples include amino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, tert-butylamino and the like, each selected within the specified number of carbon atoms. .
本明細書における「ジ(Ca~Cbアルキル)アミノ」の表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がa~b個よりなる前記の意味であるアルキルによって置換されたアミノ基を表し、例えば、ジメチルアミノ、エチル(メチル)アミノ、ジエチルアミノ、n-プロピル(メチル)アミノ、i-プロピル(メチル)アミノ、ジ(n-プロピル)アミノ、ジ(n-ブチル)アミノ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "di(C a -C b alkyl)amino" as used herein has the above-described meaning in which both hydrogen atoms have a to b carbon atoms which may be the same or different from each other. represents an amino group substituted by an alkyl which is, for example, dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di Specific examples include (n-butyl)amino and the like, which are selected within the specified range of the number of carbon atoms.
本明細書における「Ca~Cbアルキルアミノカルボニル」の表記は、水素原子の一方が炭素原子数がa~b個よりなる前記の意味であるアルキルによって置換されたアミノ-C(O)-基を表し、例えば、メチルアミノカルボニル、エチルアミノカルボニル、n-プロピルアミノカルボニル、i-プロピルアミノカルボニル、n-ブチルアミノカルボニル、i-ブチルアミノカルボニル、tert-ブチルアミノカルボニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "C a -C b alkylaminocarbonyl" as used herein means amino-C(O)- in which one of the hydrogen atoms is substituted by alkyl having a to b carbon atoms as defined above. specific examples include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, i-propylaminocarbonyl, n-butylaminocarbonyl, i-butylaminocarbonyl, tert-butylaminocarbonyl and the like. , are selected in each specified range of carbon atoms.
本明細書における「ジ(Ca~Cbアルキル)アミノカルボニル」の表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がa~b個よりなる前記の意味であるアルキルによって置換されたアミノ-C(O)-基を表し、例えば、ジメチルアミノカルボニル、エチル(メチル)アミノカルボニル、ジエチルアミノカルボニル、n-プロピル(メチル)アミノカルボニル、i-プロピル(メチル)アミノカルボニル、ジ(n-プロピル)アミノカルボニル、ジ(n-ブチル)アミノカルボニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "di(C a -C b alkyl)aminocarbonyl" in this specification means that both hydrogen atoms have a to b number of carbon atoms which may be the same or different from each other. represents an amino-C(O)- group substituted by the meaning alkyl, for example dimethylaminocarbonyl, ethyl(methyl)aminocarbonyl, diethylaminocarbonyl, n-propyl(methyl)aminocarbonyl, i-propyl(methyl) Specific examples include aminocarbonyl, di(n-propyl)aminocarbonyl, di(n-butyl)aminocarbonyl and the like, and each is selected within the designated number of carbon atoms.
本明細書における「ジ(Ca~Cbアルキル)アミノスルホニル」の表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がa~b個よりなる前記の意味であるアルキルによって置換されたアミノ-S(O)2-基を表し、例えば、ジメチルアミノスルホニル、エチル(メチル)アミノスルホニル、ジエチルアミノスルホニル、n-プロピル(メチル)アミノスルホニル、i-プロピル(メチル)アミノスルホニル、ジ(n-プロピル)アミノスルホニル、ジ(n-ブチル)アミノスルホニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "di(C a -C b alkyl)aminosulfonyl" in this specification means that both hydrogen atoms have a to b number of carbon atoms which may be the same or different from each other. represents an amino-S(O) 2 - group substituted by the meaning alkyl, for example dimethylaminosulfonyl, ethyl(methyl)aminosulfonyl, diethylaminosulfonyl, n-propyl(methyl)aminosulfonyl, i-propyl(methyl ) aminosulfonyl, di(n-propyl)aminosulfonyl, di(n-butyl)aminosulfonyl and the like are mentioned as specific examples, and each is selected within the designated number of carbon atoms.
本明細書における「トリ(Ca~Cbアルキル)シリル」の表記は、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がa~b個よりなる前記の意味であるアルキル基によって置換されたシリル基を表す。具体例として、トリメチルシリル、トリエチルシリル、トリ(n-プロピル)シリル、エチルジメチルシリル、n-プロピルジメチルシリル、n-ブチルジメチルシリル、i-ブチルジメチルシリル、tert-ブチルジメチルシリル等が挙げられ、各々の指定の炭素原子数の範囲で選択される。
The notation of "tri(C a -C b alkyl)silyl" in this specification is substituted by an alkyl group having the above-mentioned meaning and having a to b carbon atoms which may be the same or different from each other. represents a silyl group. Specific examples include trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, tert-butyldimethylsilyl and the like. is selected within the specified number of carbon atoms.
本明細書における「R8によって置換されたCa~Cbアルキル」、「R11によって置換されたCa~Cbアルキル」又は「R15によって置換されたCa~Cbアルキル」の表記は、任意のR8、R11又はR15によって、炭素原子に結合した水素原子が任意に置換された、炭素原子数がa~b個よりなる前記の意味であるアルキル基を表し、各々の指定の炭素原子数の範囲で選択される。それぞれのCa~Cbアルキル基上の置換基R8、R11又はR15が2個以上存在するとき、それぞれのR8、R11又はR15は互いに同一でも、又は互いに相異なっていてもよい。
Notation herein for “C a -C b alkyl substituted by R 8 ”, “C a -C b alkyl substituted by R 11 ” or “C a -C b alkyl substituted by R 15 ” represents an alkyl group having a to b carbon atoms and having the above-mentioned meaning, in which a hydrogen atom bonded to a carbon atom is optionally substituted with any R 8 , R 11 or R 15 ; Selected within a specified range of carbon atoms. When there are two or more substituents R 8 , R 11 or R 15 on each C a -C b alkyl group, each R 8 , R 11 or R 15 may be the same or different. good too.
本明細書における「R16によって置換されたCa~Cbシクロアルキル」の表記は、任意のR16によって、炭素原子に結合した水素原子が任意に置換された、炭素原子数がa~b個よりなる前記の意味であるシクロアルキル基を表し、各々の指定の炭素原子数の範囲で選択される。それぞれのCa~Cbシクロアルキル基上の置換基R16が2個以上存在するとき、それぞれのR16は互いに同一でも、又は互いに相異なっていてもよい。
The notation “C a -C b cycloalkyl substituted with R 16 ” as used herein refers to the number of carbon atoms from a to b in which a hydrogen atom attached to a carbon atom is optionally replaced with any R 16 . Represents a cycloalkyl group as defined above consisting of, each selected within the specified number of carbon atoms. When there are two or more substituents R 16 on each C a -C b cycloalkyl group, each R 16 may be the same or different.
本明細書における「(Z)m1によって置換されたフェニル」又は「(Z1)mによって置換されたフェニル」の表記は、任意のZ又はZ1によって、炭素原子に結合した水素原子が任意に置換されたフェニル基を表す。また、mは(Z1)mに応じて任意の値をとることが出来、m1は(Z)m1に応じて任意の値をとることが出来る。それぞれのフェニル基上の置換基Z又はZ1が2個以上存在するとき、それぞれのZ又はZ1は互いに同一でも、又は互いに相異なっていてもよい。
The notation "phenyl substituted by (Z) m1 " or "phenyl substituted by (Z1) m " as used herein means that the hydrogen atom attached to the carbon atom by any Z or Z1 is optionally represents a substituted phenyl group. Further, m can take any value according to (Z 1 ) m , and m1 can take any value according to (Z) m1 . When there are two or more substituents Z or Z 1 on each phenyl group, each Z or Z 1 may be the same or different.
本明細書におけるG-1~G-65の一部の構造に記載されている「(Z9)p1」においてp1が0の場合は、Z9に置換されていない、すなわち無置換であることを表す。
When p1 is 0 in “(Z 9 ) p1 ” described in some structures of G-1 to G-65 in this specification, it is not substituted with Z 9 , that is, unsubstituted represents
次に、式(1)で表される本発明化合物の製造方法について説明する。式(1)で表される本発明化合物は、例えば、以下の方法により製造することができる。なお、以下の説明はあくまで例示に過ぎず、式(1)で表される本発明化合物は、他の方法により製造されるものであってもよい。以下、「式(1)で表される本発明化合物」は、「本発明化合物(1)」とも記載され、また、「式(2)で表される化合物」は、「化合物(2)」とも記載される。他の化合物についてもこれに準じて同様に記載される。
Next, a method for producing the compound of the present invention represented by formula (1) will be described. The compound of the present invention represented by formula (1) can be produced, for example, by the following method. The following explanation is merely an example, and the compound of the present invention represented by formula (1) may be produced by other methods. Hereinafter, "the compound of the present invention represented by formula (1)" is also referred to as "the compound of the present invention (1)", and "the compound represented by formula (2)" is referred to as "compound (2)". Also described. Other compounds are similarly described accordingly.
(製造例1)
本発明化合物(1)は、例えば、化合物(2)と、化合物(3)とを反応させることにより製造することができる。
(Production example 1)
Compound (1) of the present invention can be produced, for example, by reacting compound (2) with compound (3).
本発明化合物(1)は、例えば、化合物(2)と、化合物(3)とを反応させることにより製造することができる。
Compound (1) of the present invention can be produced, for example, by reacting compound (2) with compound (3).
[式中、Lは塩素原子、臭素原子、ヨウ素原子、C1~C4アルキルスルホニルオキシ(例えば、メタンスルホニルオキシなど)、ハロスルホニルオキシ(例えば、フルオロスルホニルオキシなど)、C1~C4ハロアルキルスルホニルオキシ(例えば、トリフルオロメタンスルホニルオキシなど)又はアリールスルホニルオキシ(例えば、パラトルエンスルホニルオキシなど)等の脱離基を表し、R1、R2、R3、R4、R5、R6及びRbは前記と同じ意味を表す。]
化合物(1)は、化合物(2)と化合物(3)とを、溶媒中又は無溶媒で、場合によっては塩基存在下にて反応させることで製造することができる。 [In the formula, L is a chlorine atom, a bromine atom, an iodine atom, C 1 -C 4 alkylsulfonyloxy (e.g., methanesulfonyloxy, etc.), halosulfonyloxy (e.g., fluorosulfonyloxy, etc.), C 1 -C 4 haloalkyl represents a leaving group such as sulfonyloxy (e.g., trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (e.g., paratoluenesulfonyloxy, etc.), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Rb has the same meaning as above. ]
Compound (1) can be produced by reacting compound (2) and compound (3) in a solvent or in the absence of a solvent, optionally in the presence of a base.
化合物(1)は、化合物(2)と化合物(3)とを、溶媒中又は無溶媒で、場合によっては塩基存在下にて反応させることで製造することができる。 [In the formula, L is a chlorine atom, a bromine atom, an iodine atom, C 1 -C 4 alkylsulfonyloxy (e.g., methanesulfonyloxy, etc.), halosulfonyloxy (e.g., fluorosulfonyloxy, etc.), C 1 -C 4 haloalkyl represents a leaving group such as sulfonyloxy (e.g., trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (e.g., paratoluenesulfonyloxy, etc.), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Rb has the same meaning as above. ]
Compound (1) can be produced by reacting compound (2) and compound (3) in a solvent or in the absence of a solvent, optionally in the presence of a base.
用いる化合物(3)の当量としては、化合物(2)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (3) used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (2).
化合物(3)の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の一般的な公知化合物の合成方法に準じて製造することができる。
Some compounds (3) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
溶媒を用いる場合、用いられる溶媒としては反応に不活性であればよく、例えば、水、メタノール、エタノール等のアルコール溶媒、ジエチルエーテル、テトラヒドロフラン、1,4-ジオキサン、1,2-ジメトキシエタン等のエーテル溶媒、ベンゼン、キシレン、トルエン等の芳香族炭化水素溶媒、ペンタン、ヘキサン、シクロヘキサン等の脂肪族炭化水素溶媒、ジクロロメタン、クロロホルム、1,2-ジクロロエタン等のハロゲン化炭化水素溶媒、アセトニトリル、プロピオニトリル等のニトリル溶媒、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン、N,N’-ジメチルイミダゾリジノン等のアミド溶媒、ジメチルスルホキシド或いはこれらの混合溶媒等が挙げられる。
When a solvent is used, the solvent to be used may be inert to the reaction. Examples include water, alcohol solvents such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Ether solvents, aromatic hydrocarbon solvents such as benzene, xylene and toluene; aliphatic hydrocarbon solvents such as pentane, hexane and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform and 1,2-dichloroethane; Nitrile solvents such as nitrile, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, dimethylsulfoxide, and mixed solvents thereof. .
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、ピリジン、2,6-ルチジン、4-ジメチルアミノピリジン、トリエチルアミン、ジイソプロピルエチルアミン、トリブチルアミン、N,N-ジメチルアニリン、1,4-ジアザビシクロ[2.2.2]オクタン(DABCO)、1,8-ジアザビシクロ[5.4.0]-7-ウンデセン(DBU)、1,5-ジアザビシクロ[4.3.0]-5-ノネン(DBN)等の有機塩基、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸セシウム、リン酸カリウム等の無機塩基、ナトリウムメトキシド、ナトリウムエトキシド、カリウムtert-ブトキシド等の金属アルコキシドが挙げられる。塩基の使用量(当量)は、化合物(2)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo [2.2.2 ] octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), organic bases such as 1,5-diazabicyclo[4.3.0]-5-nonene (DBN), Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate and potassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents per equivalent of compound (2).
反応温度は-78℃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。また、反応時間は、反応基質の濃度、反応温度によって変化するが、通常5分から100時間の範囲で任意に設定できる。
The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can be set arbitrarily within the range of usually 5 minutes to 100 hours.
(製造例2)
本発明化合物(1)のうち、R2が-C(O)R9である化合物(1-4)は、例えば、化合物(1-3)と化合物(4)とを反応させることにより製造することができる。
(Production example 2)
Among the compounds (1) of the present invention, the compound (1-4) in which R 2 is —C(O)R 9 is produced, for example, by reacting the compound (1-3) with the compound (4). be able to.
本発明化合物(1)のうち、R2が-C(O)R9である化合物(1-4)は、例えば、化合物(1-3)と化合物(4)とを反応させることにより製造することができる。
Among the compounds (1) of the present invention, the compound (1-4) in which R 2 is —C(O)R 9 is produced, for example, by reacting the compound (1-3) with the compound (4). be able to.
(式中、Xはハロゲン原子を表し、R1、R3、R4、R5、R6、R9及びRbは前記と同じ意味を表す。)
化合物(1-4)は、化合物(1-3)と化合物(4)とを、溶媒中又は無溶媒で、場合によっては塩基及び添加物のうち何れか一方、或いは両方の存在下で、反応させることで製造することができる。 (In the formula, X represents a halogen atom, and R 1 , R 3 , R 4 , R 5 , R 6 , R 9 and R b have the same meanings as above.)
Compound (1-4) is obtained by reacting compound (1-3) and compound (4) in a solvent or in the absence of a solvent, optionally in the presence of one or both of a base and an additive. It can be manufactured by
化合物(1-4)は、化合物(1-3)と化合物(4)とを、溶媒中又は無溶媒で、場合によっては塩基及び添加物のうち何れか一方、或いは両方の存在下で、反応させることで製造することができる。 (In the formula, X represents a halogen atom, and R 1 , R 3 , R 4 , R 5 , R 6 , R 9 and R b have the same meanings as above.)
Compound (1-4) is obtained by reacting compound (1-3) and compound (4) in a solvent or in the absence of a solvent, optionally in the presence of one or both of a base and an additive. It can be manufactured by
用いる化合物(4)の当量としては、化合物(1-3)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (4) used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (1-3).
化合物(4)の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の一般的な公知化合物の合成方法に準じて製造することができる。
Some compounds (4) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造法1で例示の溶媒が挙げられる。
When a solvent is used, the solvent to be used may be inert to the reaction, and examples thereof include the solvents exemplified in Production Method 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(1-3)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-3).
該反応は添加物の存在下に行うことができる。用いることのできる添加物としては、3H-[1,2,3]トリアゾロ[4,5-b]ピリジン-3-オール、1-ヒドロキシベンゾトリアゾール、N、N-ジメチル-4-アミノピリジン等が挙げられる。添加剤の使用量(当量)は化合物(1-3)に対して、0.1~100当量で用いることができる。
The reaction can be carried out in the presence of additives. Additives that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, and the like. mentioned. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (1-3).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
(製造例3)
本発明化合物(1)のうち、R2がA1である化合物(1-5)は、例えば、化合物(1-3)と化合物(5)とを反応させることにより製造することができる。
(Production example 3)
Of the compounds (1) of the present invention, compound (1-5) in which R 2 is A 1 can be produced, for example, by reacting compound (1-3) with compound (5).
本発明化合物(1)のうち、R2がA1である化合物(1-5)は、例えば、化合物(1-3)と化合物(5)とを反応させることにより製造することができる。
Of the compounds (1) of the present invention, compound (1-5) in which R 2 is A 1 can be produced, for example, by reacting compound (1-3) with compound (5).
(式中、A1はR8によって置換されたC1~C6アルキル、C2~C6アルケニル又はC2~C6ハロアルケニルを表し、R1、R3、R4、R5、R6、R8、Rb及びLは前記と同じ意味を表す。)
化合物(1-5)は、化合物(1-3)と化合物(5)とを、溶媒中又は無溶媒で、場合によっては塩基存在下で、反応させることで製造することができる。 (wherein A 1 represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 haloalkenyl substituted by R 8 and R 1 , R 3 , R 4 , R 5 , R 6 , R 8 , R b and L have the same meanings as above.)
Compound (1-5) can be produced by reacting compound (1-3) and compound (5) in a solvent or in the absence of a solvent, optionally in the presence of a base.
化合物(1-5)は、化合物(1-3)と化合物(5)とを、溶媒中又は無溶媒で、場合によっては塩基存在下で、反応させることで製造することができる。 (wherein A 1 represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 haloalkenyl substituted by R 8 and R 1 , R 3 , R 4 , R 5 , R 6 , R 8 , R b and L have the same meanings as above.)
Compound (1-5) can be produced by reacting compound (1-3) and compound (5) in a solvent or in the absence of a solvent, optionally in the presence of a base.
用いる化合物(5)の当量としては、化合物(1-3)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (5) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (1-3).
化合物(5)の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の一般的な公知化合物の合成方法に準じて製造することができる。
Some compounds (5) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(1-3)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-3).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
(製造例4)
本発明化合物(1)のうち、R4が-C≡C-R7である化合物(1-7)は、例えば、化合物(1-6)と化合物(6)とを反応させることにより製造することができる。
(Production example 4)
Among the compounds (1) of the present invention, compounds (1-7) in which R 4 is —C≡C—R 7 are produced, for example, by reacting compounds (1-6) with compounds (6). be able to.
本発明化合物(1)のうち、R4が-C≡C-R7である化合物(1-7)は、例えば、化合物(1-6)と化合物(6)とを反応させることにより製造することができる。
Among the compounds (1) of the present invention, compounds (1-7) in which R 4 is —C≡C—R 7 are produced, for example, by reacting compounds (1-6) with compounds (6). be able to.
(式中、A2は水素原子又はトリ(C1~C6アルキル)シリルを表し、X、R1、R2、R3、R5、R6、R7及びRbは前記と同じ意味を表す。)
化合物(1-7)は、化合物(1-6)と化合物(6)とを、溶媒中又は無溶媒で、場合によってはパラジウム触媒存在下で、必要に応じて銅触媒、添加物、フッ化物及び塩基のうち何れか一つ以上の存在下で、反応させることで製造することができる。 (wherein A 2 represents a hydrogen atom or tri(C 1 -C 6 alkyl)silyl, X, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and R b have the same meanings as above) represents.)
Compound (1-7) is prepared by reacting compound (1-6) and compound (6) in a solvent or in the absence of a solvent, optionally in the presence of a palladium catalyst, optionally with a copper catalyst, an additive, a fluoride and a base in the presence of any one or more, it can be produced by reacting.
化合物(1-7)は、化合物(1-6)と化合物(6)とを、溶媒中又は無溶媒で、場合によってはパラジウム触媒存在下で、必要に応じて銅触媒、添加物、フッ化物及び塩基のうち何れか一つ以上の存在下で、反応させることで製造することができる。 (wherein A 2 represents a hydrogen atom or tri(C 1 -C 6 alkyl)silyl, X, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and R b have the same meanings as above) represents.)
Compound (1-7) is prepared by reacting compound (1-6) and compound (6) in a solvent or in the absence of a solvent, optionally in the presence of a palladium catalyst, optionally with a copper catalyst, an additive, a fluoride and a base in the presence of any one or more, it can be produced by reacting.
用いる化合物(6)の当量としては、化合物(1-6)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (6) to be used can be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (1-6).
化合物(6)の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の一般的な公知化合物の合成方法に準じて製造することができる。
Some compounds (6) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応はパラジウム触媒の存在下に行うことができる。用いることのできるパラジウム触媒としては、例えば、酢酸パラジウム、テトラキス(トリフェニルホスフィン)パラジウム(0価)、トリス(ジベンジリデンアセトン)ジパラジウム(0価)、ビス(トリフェニルホスフィン)パラジウム(2価)ジクロリド、[1、1’-ビス(ジフェニルホスフィノ)フェロセン]パラジウム(2価)ジクロリド ジクロロメタン付加物、[1,3-ビス(2,6-ジイソプロピルフェニル)イミダゾール-2-イリデン](3-クロロピリジル)パラジウム(2価)ジクロリド等が挙げられる。パラジウム触媒の使用量(当量)は、化合物(1-6)1当量に対して、0.005~20当量で用いることができる。
The reaction can be carried out in the presence of a palladium catalyst. Palladium catalysts that can be used include, for example, palladium acetate, tetrakis(triphenylphosphine)palladium (zero valence), tris(dibenzylideneacetone) dipalladium (0 valence), bis(triphenylphosphine) palladium (bivalence) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloro pyridyl)palladium (divalent) dichloride and the like. The amount (equivalent) of the palladium catalyst used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
該反応は銅触媒の存在下に行うことができる。用いることのできる銅触媒としては、例えば、ヨウ化銅、塩化銅(1価)等が挙げられる。銅触媒の使用量(当量)は、化合物(1-6)1当量に対して、0.005~20当量で用いることができる。
The reaction can be carried out in the presence of a copper catalyst. Copper catalysts that can be used include, for example, copper iodide and copper chloride (monovalent). The amount (equivalent) of the copper catalyst used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
該反応は添加物の存在下に行うことができる。用いることのできる添加物としては、例えば4,5-ビス(ジフェニルホスフィノ)-9,9-ジメチルキサンテン等が挙げられる。添加物の使用量(当量)は、化合物(1-6)1当量に対して、0.005~20当量で用いることができる。
The reaction can be carried out in the presence of additives. Additives that can be used include, for example, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene. The amount (equivalent) of the additive used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
該反応はフッ化物の存在下に行うことができる。用いることのできるフッ化物としては、例えば、テトラ-n-ブチルアンモニウムフルオリド等が挙げられる。フッ化物の使用量(当量)は、化合物(1-6)1当量に対して、0.005~20当量で用いることができる。
The reaction can be performed in the presence of fluoride. Fluorides that can be used include, for example, tetra-n-butylammonium fluoride and the like. The amount (equivalent) of fluoride to be used can be 0.005 to 20 equivalents per equivalent of compound (1-6).
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(1-6)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-6).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
(製造例5)
本発明化合物(1)のうち、R4が-C≡CHである化合物(1-8)は、例えば、化合物(1-9)と塩基とを反応させることにより製造することができる。
(Production example 5)
Of the compounds (1) of the present invention, the compound (1-8) in which R 4 is —C≡CH can be produced, for example, by reacting the compound (1-9) with a base.
本発明化合物(1)のうち、R4が-C≡CHである化合物(1-8)は、例えば、化合物(1-9)と塩基とを反応させることにより製造することができる。
Of the compounds (1) of the present invention, the compound (1-8) in which R 4 is —C≡CH can be produced, for example, by reacting the compound (1-9) with a base.
(式中、R1、R2、R3、R5、R6、Ra、Ra1及びRbは前記と同じ意味を表す。)
化合物(1-8)は、化合物(1-9)を、溶媒中又は無溶媒で、塩基存在下で、反応させることで製造することができる。 (In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , R a , R a1 and R b have the same meanings as above.)
Compound (1-8) can be produced by reacting compound (1-9) in the presence of a base in a solvent or without solvent.
化合物(1-8)は、化合物(1-9)を、溶媒中又は無溶媒で、塩基存在下で、反応させることで製造することができる。 (In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , R a , R a1 and R b have the same meanings as above.)
Compound (1-8) can be produced by reacting compound (1-9) in the presence of a base in a solvent or without solvent.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(1-9)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents per equivalent of compound (1-9).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
製造例1に用いられる化合物(2)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。
The compound (2) used in Production Example 1 can be produced, for example, according to the production route (reaction route) shown by the following reaction formula.
(式中、X、R1、R2、R3、R4、R5、Ra及びRbは前記と同じ意味を表す。)
(Wherein, X, R 1 , R 2 , R 3 , R 4 , R 5 , Ra and Rb have the same meanings as above.)
化合物(2)は化合物(3-a)と化合物(A)とを溶媒中又は無溶媒で場合によっては塩基存在下反応させることにより得ることができる。
Compound (2) can be obtained by reacting compound (3-a) and compound (A) in a solvent or in the absence of a solvent, optionally in the presence of a base.
用いる化合物(A)の当量としては、化合物(3-a)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent amount of compound (A) used can be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (3-a).
化合物(A)の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の一般的な公知化合物の合成方法に準じて製造することができる。
Some of the compounds (A) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-a)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-a).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(3-a)は化合物(3-b)と塩基とを溶媒中又は無溶媒で反応させることにより得ることができる。
Compound (3-a) can be obtained by reacting compound (3-b) with a base in a solvent or without solvent.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-b)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-b).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(3-b)は化合物(3-c)とカルボニルジイミダゾール又はトリホスゲンとを、溶媒中又は無溶媒で、場合によっては塩基存在下で反応させ、次いで化合物(B)と反応させることにより得ることができる。
Compound (3-b) is obtained by reacting compound (3-c) with carbonyldiimidazole or triphosgene in a solvent or in the absence of a solvent, optionally in the presence of a base, and then reacting with compound (B). be able to.
用いるカルボニルジイミダゾール又はトリホスゲンの当量としては、化合物(3-c)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of carbonyldiimidazole or triphosgene used can be in the range of 0.5 to 50 equivalents per equivalent of compound (3-c).
用いる化合物(B)の当量としては、化合物(3-c)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (B) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-c).
化合物(B)の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の一般的な公知化合物の合成方法に準じて製造することができる。
Some of the compounds (B) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-c)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-c).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(3-c)のあるものは国際公開2013/071169号に記載の公知化合物であり、また、それ以外のものも当該文献記載の方法に準じて公知の化合物と同様に合成することができる。
Some compounds (3-c) are known compounds described in WO 2013/071169, and others can be synthesized in the same manner as known compounds according to the method described in the document. .
化合物(2)のうち、R2が水素原子である化合物(2-a)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。
Among compounds (2), compound (2-a) in which R 2 is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
[反応式2]
(式中、R2aはC1~C6アルコキシカルボニルを表し、R1、R3、R4、R5及びRbは前記と同じ意味を表す。)
化合物(2-a)は化合物(2-b)を溶媒中又は無溶媒で酸存在下反応させることにより得ることができる。 [Reaction Formula 2]
(In the formula, R 2a represents C 1 to C 6 alkoxycarbonyl, and R 1 , R 3 , R 4 , R 5 and R b have the same meanings as above.)
Compound (2-a) can be obtained by reacting compound (2-b) in the presence of an acid in a solvent or without solvent.
化合物(2-a)は化合物(2-b)を溶媒中又は無溶媒で酸存在下反応させることにより得ることができる。 [Reaction Formula 2]
Compound (2-a) can be obtained by reacting compound (2-b) in the presence of an acid in a solvent or without solvent.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は酸の存在下に行うことができる。用いることのできる酸としては、例えば、塩酸、硫酸、硝酸、酢酸、トリフルオロ酢酸、パラトルエンスルホン酸1水和物等が挙げられる。酸の使用量(当量)は、化合物(2-b)1当量に対して、0.1~100当量で用いることができる。
The reaction can be carried out in the presence of an acid. Acids that can be used include, for example, hydrochloric acid, sulfuric acid, nitric acid, acetic acid, trifluoroacetic acid, p-toluenesulfonic acid monohydrate, and the like. The amount (equivalent) of the acid used can be 0.1 to 100 equivalents per equivalent of compound (2-b).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
製造例4に用いられる化合物(1-6)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。
The compound (1-6) used in Production Example 4 can be produced, for example, according to the production route (reaction pathway) shown in the reaction scheme below.
(式中、X、L、R1、R2、R3、R5、R6及びRbは前記と同じ意味を表す。)
(Wherein, X, L, R 1 , R 2 , R 3 , R 5 , R 6 and R b have the same meanings as above.)
化合物(1-6)は、化合物(2-c)と化合物(3)とを反応させて、製造例1に記載の方法に準じて合成することができる。
化合物(2-c)は、化合物(3-d)と上述の化合物(A)とを溶媒中又は無溶媒で場合によっては塩基存在下反応させることにより得ることができる。 Compound (1-6) can be synthesized according to the method described in Production Example 1 by reacting compound (2-c) with compound (3).
Compound (2-c) can be obtained by reacting compound (3-d) with compound (A) above in a solvent or in the absence of a solvent, optionally in the presence of a base.
化合物(2-c)は、化合物(3-d)と上述の化合物(A)とを溶媒中又は無溶媒で場合によっては塩基存在下反応させることにより得ることができる。 Compound (1-6) can be synthesized according to the method described in Production Example 1 by reacting compound (2-c) with compound (3).
Compound (2-c) can be obtained by reacting compound (3-d) with compound (A) above in a solvent or in the absence of a solvent, optionally in the presence of a base.
用いる化合物(A)の当量としては、化合物(3-d)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (A) used can be in the range of 0.5 to 50 equivalents per equivalent of compound (3-d).
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-d)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-d).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(3-d)は化合物(3-e)とハロゲン化剤とを溶媒中又は無溶媒で、場合によっては添加物存在下で、反応させることにより得ることができる。
Compound (3-d) can be obtained by reacting compound (3-e) with a halogenating agent in a solvent or in the absence of a solvent, optionally in the presence of additives.
用いることのできるハロゲン化剤としては、例えば、塩素、臭素、ヨウ素、N-クロロスクシンイミド、N-ブロモスクシンイミド、N-ヨードスクシンイミド等が挙げられる。ハロゲン化剤の使用量(当量)は、化合物(3-e)1当量に対して、0.1~100当量で用いることができる。
Examples of usable halogenating agents include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like. The amount (equivalent) of the halogenating agent to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-e).
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒又は酢酸等が挙げられる。
When a solvent is used, the solvent to be used may be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1, acetic acid, and the like.
該反応は添加物の存在下に行うことができる。用いることのできる添加物としては、例えば、酢酸ナトリウム等が挙げられる。添加物の使用量(当量)は、化合物(3-e)1当量に対して、0.1~100当量で用いることができる。
The reaction can be carried out in the presence of additives. Additives that can be used include, for example, sodium acetate. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents per equivalent of compound (3-e).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(3-a)のうち、R4がL-1である化合物(3-f)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。
Of compounds (3-a), compound (3-f) in which R4 is L-1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
(式中、X、R1、R2、R5及びRaは前記と同じ意味を表す。)
化合物(3-f)は化合物(3-g)と化合物(C)とを溶媒中又は無溶媒で、場合によっては縮合剤、添加物及び塩基のうち何れか一つ以上の存在下反応させることにより得ることができる。 (Wherein, X, R 1 , R 2 , R 5 and R a have the same meanings as above.)
Compound (3-f) is obtained by reacting compound (3-g) and compound (C) in a solvent or in the absence of a solvent, optionally in the presence of one or more of a condensing agent, an additive and a base. can be obtained by
化合物(3-f)は化合物(3-g)と化合物(C)とを溶媒中又は無溶媒で、場合によっては縮合剤、添加物及び塩基のうち何れか一つ以上の存在下反応させることにより得ることができる。 (Wherein, X, R 1 , R 2 , R 5 and R a have the same meanings as above.)
Compound (3-f) is obtained by reacting compound (3-g) and compound (C) in a solvent or in the absence of a solvent, optionally in the presence of one or more of a condensing agent, an additive and a base. can be obtained by
用いる化合物(C)の当量としては、化合物(3-g)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (C) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-g).
化合物(C)の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の一般的な公知化合物の合成方法に準じて製造することができる。
Some of the compounds (C) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in literatures.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は縮合剤の存在下に行うことができる。用いることのできる縮合剤としては、1H-ベンゾトリアゾール-1-イルオキシトリス(ジメチルアミノ)ホスホニウムヘキサフルオロホスファート、N,N’-ジシクロヘキシルカルボジイミド、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミド塩酸塩、2-クロロ-1-メチルピリジニウムヨージド、プロピルホスホン酸無水物等が挙げられる。縮合剤の使用量(当量)は、化合物(3-g)1当量に対して、0.1~100当量で用いることができる。
The reaction can be carried out in the presence of a condensing agent. Condensing agents that can be used include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride, 2-chloro-1-methylpyridinium iodide, propylphosphonic anhydride and the like. The amount (equivalent) of the condensing agent to be used can be 0.1 to 100 equivalents per equivalent of compound (3-g).
該反応は添加物の存在下に行うことができる。用いることのできる添加物としては、例えば、4-ジメチルアミノピリジン、3H-[1,2,3]トリアゾロ[4,5-b]ピリジン-3-オール、1-ヒドロキシベンゾトリアゾール等が挙げられる。添加物の使用量(当量)は、化合物(3-g)1当量に対して、0.005~20当量で用いることができる。
The reaction can be carried out in the presence of additives. Additives that can be used include, for example, 4-dimethylaminopyridine, 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole and the like. The amount (equivalent) of the additive used can be 0.005 to 20 equivalents per equivalent of compound (3-g).
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-g)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents per equivalent of compound (3-g).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(3-g)は化合物(3-h)を溶媒中又は無溶媒で、塩基存在下反応させることにより得ることができる。
Compound (3-g) can be obtained by reacting compound (3-h) in a solvent or without a solvent in the presence of a base.
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-h)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-h).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
化合物(2)のうち、化合物(2-d)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。 The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
Among compounds (2), compound (2-d) can be produced, for example, according to the production route (reaction route) shown in the following reaction scheme.
化合物(2)のうち、化合物(2-d)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。 The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
Among compounds (2), compound (2-d) can be produced, for example, according to the production route (reaction route) shown in the following reaction scheme.
[反応式5]
(式中、X、R1、R2、R3、R5、Ra及びRbは前記と同じ意味を表す。)
化合物(3-k)は化合物(3-g)と還元剤とを溶媒中又は無溶媒で場合によっては添加剤存在下反応させることにより得ることができる。 [Reaction formula 5]
(Wherein, X, R 1 , R 2 , R 3 , R 5 , Ra and Rb have the same meanings as above.)
Compound (3-k) can be obtained by reacting compound (3-g) with a reducing agent in a solvent or in the absence of a solvent, optionally in the presence of an additive.
化合物(3-k)は化合物(3-g)と還元剤とを溶媒中又は無溶媒で場合によっては添加剤存在下反応させることにより得ることができる。 [Reaction formula 5]
Compound (3-k) can be obtained by reacting compound (3-g) with a reducing agent in a solvent or in the absence of a solvent, optionally in the presence of an additive.
該反応は還元剤の存在下に行うことができる。用いることのできる還元剤としては、例えば、水素化ホウ素ナトリウム、水素化ホウ素リチウム、水素化リチウムアルミニウム等が挙げられる。還元剤の当量としては、化合物(3-g)1当量に対して、0.5から50当量の範囲で用いることができる。
The reaction can be carried out in the presence of a reducing agent. Usable reducing agents include, for example, sodium borohydride, lithium borohydride, lithium aluminum hydride and the like. The equivalent of the reducing agent can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-g).
該反応は添加剤の存在下に行うことができる。用いることのできる添加剤としては、例えば、1、1’-カルボニルジイミダゾール等が挙げられる。添加剤の当量としては、化合物(3-g)1当量に対して、0.5から50当量の範囲で用いることができる。
The reaction can be carried out in the presence of additives. Additives that can be used include, for example, 1,1'-carbonyldiimidazole and the like. The equivalent of the additive can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-g).
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(2-e)は化合物(3-k)と化合物(A)とを溶媒中又は無溶媒で場合によっては塩基存在下反応させることにより得ることができる。
Compound (2-e) can be obtained by reacting compound (3-k) with compound (A) in a solvent or in the absence of a solvent, optionally in the presence of a base.
用いる化合物(A)の当量としては、化合物(3-k)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (A) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-k).
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-k)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-k).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(2-d)は化合物(2-e)とRaOH(式中、Raは前記と同じ意味を表す。)で表されるアルコールとを溶媒中又は無溶媒で場合によっては酸存在下反応させることにより得ることができる。
Compound (2-d) is prepared by combining compound (2-e) and an alcohol represented by R a OH (wherein R a has the same meaning as defined above) in a solvent or in the absence of a solvent, optionally in the presence of an acid. It can be obtained by a lower reaction.
該反応はRaOHで表されるアルコールの存在下に行うことができる。用いることのできるアルコールとしては、RaOHに包含されるものであればよく、例えば、メタノール、エタノール、イソプロパノール等が挙げられる。
The reaction can be carried out in the presence of an alcohol represented by R a OH. Alcohols that can be used are those included in R a OH, and examples thereof include methanol, ethanol, isopropanol, and the like.
用いるアルコールの当量としては、化合物(2-e)1当量に対して、1から1000当量の範囲で用いることができる。
The equivalent of the alcohol used can be in the range of 1 to 1000 equivalents with respect to 1 equivalent of compound (2-e).
該反応は酸の存在下に行うことができる。用いることのできる酸としては、例えば、反応式1で例示の酸が挙げられる。酸の使用量(当量)は、化合物(2-e)1当量に対して、0.01~100当量で用いることができる。
The reaction can be carried out in the presence of an acid. Acids that can be used include, for example, the acids exemplified in Reaction Scheme 1. The amount (equivalent) of the acid used can be 0.01 to 100 equivalents per equivalent of compound (2-e).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(2)のうち、R4がL-2である化合物(2-g)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。
Among compounds (2), compound (2-g) in which R 4 is L-2 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
[反応式6]
(式中、X、R1、R2、R3、R5及びRbは前記と同じ意味を表す。)
化合物(2-f)は化合物(2-g)を溶媒中又は無溶媒で場合によっては酸存在下反応させることにより得ることができる。 [Reaction Formula 6]
(Wherein, X, R 1 , R 2 , R 3 , R 5 and R b have the same meanings as above.)
Compound (2-f) can be obtained by reacting compound (2-g) in a solvent or in the absence of a solvent, optionally in the presence of an acid.
化合物(2-f)は化合物(2-g)を溶媒中又は無溶媒で場合によっては酸存在下反応させることにより得ることができる。 [Reaction Formula 6]
Compound (2-f) can be obtained by reacting compound (2-g) in a solvent or in the absence of a solvent, optionally in the presence of an acid.
該反応は酸の存在下に行うことができる。用いることのできる酸としては、例えば、反応式2で例示の酸が挙げられる。酸の使用量(当量)は、化合物(2-g)1当量に対して、0.01~100当量で用いることができる。
The reaction can be carried out in the presence of an acid. Acids that can be used include, for example, the acids exemplified in Reaction Formula 2. The amount (equivalent) of the acid used can be 0.01 to 100 equivalents per equivalent of compound (2-g).
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(2-g)は化合物(2-h)とチオ尿素とを溶媒中又は無溶媒で反応させ、次いで塩基を反応させることにより得ることができる。
Compound (2-g) can be obtained by reacting compound (2-h) with thiourea in a solvent or without solvent, and then reacting with a base.
用いるチオ尿素の当量としては、化合物(2-h)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of thiourea to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (2-h).
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(2-h)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-h).
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
化合物(2-h)は化合物(3-i)と化合物(A)とを、溶媒中又は無溶媒で場合によっては塩基存在下反応させることにより得ることができる。
Compound (2-h) can be obtained by reacting compound (3-i) with compound (A) in a solvent or in the absence of a solvent, optionally in the presence of a base.
用いる化合物(A)の当量としては、化合物(3-i)1当量に対して、0.5から50当量の範囲で用いることができる。
The equivalent of compound (A) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (3-i).
溶媒を用いる場合、用いられる溶媒は反応に不活性であればよく、例えば製造例1で例示の溶媒が挙げられる。
When using a solvent, the solvent used should be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.
該反応は塩基の存在下に行うことができる。用いることのできる塩基としては、例えば、製造例1で例示の塩基が挙げられる。塩基の使用量(当量)は、化合物(3-i)1当量に対して、0.1~100当量で用いることができる。
The reaction can be performed in the presence of a base. Bases that can be used include, for example, the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (3-i).
反応温度及び反応時間は、製造例1に記載の温度範囲、時間範囲である。
The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.
反応式3~6で用いられる化合物(3-d)、化合物(3-e)、化合物(3-h)及び化合物(3-i)に該当する化合物(3’-a)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。
Compound (3'-a) corresponding to compound (3-d), compound (3-e), compound (3-h) and compound (3-i) used in Reaction Schemes 3 to 6 is, for example, the following It can be produced according to the production route (reaction route) shown by the reaction formula.
[反応式7]
(式中、R4’は水素原子、ハロゲン原子、-C(O)ORa又は-C(O)NHCH2CH2Xを表し、X、R1、R2、R3、R5、Ra及びRbは前記と同じ意味を表す。)
化合物(3’-a)は、反応式1に記載の方法に準じて合成することができる。 [Reaction Formula 7]
(Wherein, R 4′ represents a hydrogen atom, a halogen atom, —C(O)OR a or —C(O)NHCH 2 CH 2 X, and X, R 1 , R 2 , R 3 , R 5 , R a and Rb have the same meanings as above.)
Compound (3′-a) can be synthesized according to the method described in Reaction Scheme 1.
化合物(3’-a)は、反応式1に記載の方法に準じて合成することができる。 [Reaction Formula 7]
Compound (3′-a) can be synthesized according to the method described in Reaction Scheme 1.
化合物(3’-c)のあるものは国際公開2013/071169号に記載の公知化合物であり、また、それ以外のものも当該文献記載の方法に準じて公知の化合物と同様に合成することができる。
Some of the compounds (3'-c) are known compounds described in WO 2013/071169, and others can be synthesized in the same manner as known compounds according to the method described in the document. can.
また、化合物(2-c)及び化合物(2-h)を包含する化合物(2’)は、化合物(3’-a)と化合物(A)とを溶媒中又は無溶媒で場合によっては塩基存在下反応させることにより得ることができる。
Further, compound (2') including compound (2-c) and compound (2-h) can be prepared by combining compound (3'-a) and compound (A) in a solvent or without a solvent, optionally in the presence of a base. It can be obtained by a lower reaction.
化合物(2’)は、反応式1に記載の方法に準じて合成することができる。
Compound (2') can be synthesized according to the method described in Reaction Scheme 1.
化合物(2’)のうち、R2が水素原子である化合物(2’-a)は、例えば下記の反応式で示される製造ルート(反応経路)にしたがって製造することができる。
Among the compounds (2'), the compound (2'-a) in which R 2 is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.
[反応式8]
(式中、R1、R2a、R3、R4’、R5及びRbは前記と同じ意味を表す。)
化合物(2’-a)は化合物(2’-b)を溶媒中又は無溶媒で酸存在下反応させることにより得ることができる。 [Reaction Formula 8]
(In the formula, R 1 , R 2a , R 3 , R 4′ , R 5 and R b have the same meanings as above.)
Compound (2'-a) can be obtained by reacting compound (2'-b) in the presence of an acid in a solvent or without solvent.
化合物(2’-a)は化合物(2’-b)を溶媒中又は無溶媒で酸存在下反応させることにより得ることができる。 [Reaction Formula 8]
Compound (2'-a) can be obtained by reacting compound (2'-b) in the presence of an acid in a solvent or without solvent.
反応条件は、反応式2に記載している内容と同じである。
The reaction conditions are the same as those described in Reaction Formula 2.
製造例1~5、反応式1~8の反応において、反応終了後の反応混合物は、直接濃縮又は有機溶媒に溶解し、水洗後濃縮又は氷水に投入、有機溶媒抽出後濃縮等の通常の後処理を行ない、目的の化合物を得ることができる。また、精製の必要が生じたときには、再結晶、カラムクロマトグラフ、薄層クロマトグラフ、液体クロマトグラフ分取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。
In the reactions of Production Examples 1 to 5 and Reaction Schemes 1 to 8, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water and then concentrated or put into ice water, extracted with an organic solvent and then concentrated. Workup can be carried out to obtain the desired compound. In addition, when purification is required, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography, liquid chromatography, and the like.
これらの方法を用いて製造できる本発明化合物としては、例えば第1表に示す化合物が挙げられる。但し、第1表は例示のためのものであって、本発明化合物はこれらのみに限定されるものではない。
The compounds of the present invention that can be produced using these methods include, for example, the compounds shown in Table 1. However, Table 1 is for illustration only, and the compounds of the present invention are not limited to these.
なお、表中、Meとの記載はメチルを表し、Etとの記載はエチルを表し、≡との記載は3重結合を表す。
In the table, Me represents methyl, Et represents ethyl, and ≡ represents a triple bond.
また、表中、T-01からT-26の表記は下記の構造を表す。
また、表中、U-01からU-09の表記は下記の構造を表す。
なお、上記のT-01からT-26及びU-01からU-09の構造式に記載の「*」は結合箇所を表す。
In the table, T-01 to T-26 represent the following structures.
In the table, notations U-01 to U-09 represent the following structures.
The asterisks "*" in the structural formulas of T-01 to T-26 and U-01 to U-09 represent the binding sites.
表中のR2及びR6欄は、上記T-01からT-26及びU-01からU-09が、式(X)で表される化合物のR2及びR6にそれぞれ結合していることを表し、表中、(Z)m1の置換位置を表す番号は、式(X)に記された番号に対応するものである。
Columns R 2 and R 6 in the table indicate that the above T-01 to T-26 and U-01 to U-09 are respectively bound to R 2 and R 6 of the compound represented by formula (X). In the table, the number representing the substitution position of (Z) m1 corresponds to the number described in formula (X).
例えば、第1表において、R2がT-01であり、R6がU-01であり、R4が4,5-ジヒドロオキサゾール-2-イルであり、(Z)m1が2-OMe-5-Fである場合は、以下の化合物を表す。
[第1表]
条件:R4は4,5-ジヒドロオキサゾール-2-イルであり、(Z)m1は2-OMe-5-Fである。
――――――― ――――――― ―――――――
R2 R6 R2 R6 R2 R6
――――――― ――――――― ―――――――
T-01 U-01 T-01 U-02 T-01 U-03
T-02 U-01 T-02 U-02 T-02 U-03
T-03 U-01 T-03 U-02 T-03 U-03
T-04 U-01 T-04 U-02 T-04 U-03
T-05 U-01 T-05 U-02 T-05 U-03
T-06 U-01 T-06 U-02 T-06 U-03
T-07 U-01 T-07 U-02 T-07 U-03
T-08 U-01 T-08 U-02 T-08 U-03
T-09 U-01 T-09 U-02 T-09 U-03
T-10 U-01 T-10 U-02 T-10 U-03
T-11 U-01 T-11 U-02 T-11 U-03
T-12 U-01 T-12 U-02 T-12 U-03
T-13 U-01 T-13 U-02 T-13 U-03
T-14 U-01 T-14 U-02 T-14 U-03
T-15 U-01 T-15 U-02 T-15 U-03
T-16 U-01 T-16 U-02 T-16 U-03
T-17 U-01 T-17 U-02 T-17 U-03
T-18 U-01 T-18 U-02 T-18 U-03
T-19 U-01 T-19 U-02 T-19 U-03
T-20 U-01 T-20 U-02 T-20 U-03
T-21 U-01 T-21 U-02 T-21 U-03
T-22 U-01 T-22 U-02 T-22 U-03
T-23 U-01 T-23 U-02 T-23 U-03
T-24 U-01 T-24 U-02 T-24 U-03
T-25 U-01 T-25 U-02 T-25 U-03
T-26 U-01 T-26 U-02 T-26 U-03
T-01 U-04 T-01 U-05 T-01 U-06
T-02 U-04 T-02 U-05 T-02 U-06
T-03 U-04 T-03 U-05 T-03 U-06
T-04 U-04 T-04 U-05 T-04 U-06
T-05 U-04 T-05 U-05 T-05 U-06
T-06 U-04 T-06 U-05 T-06 U-06
T-07 U-04 T-07 U-05 T-07 U-06
T-08 U-04 T-08 U-05 T-08 U-06
T-09 U-04 T-09 U-05 T-09 U-06
T-10 U-04 T-10 U-05 T-10 U-06
T-11 U-04 T-11 U-05 T-11 U-06
T-12 U-04 T-12 U-05 T-12 U-06
T-13 U-04 T-13 U-05 T-13 U-06
T-14 U-04 T-14 U-05 T-14 U-06
T-15 U-04 T-15 U-05 T-15 U-06
T-16 U-04 T-16 U-05 T-16 U-06
T-17 U-04 T-17 U-05 T-17 U-06
T-18 U-04 T-18 U-05 T-18 U-06
T-19 U-04 T-19 U-05 T-19 U-06
T-20 U-04 T-20 U-05 T-20 U-06
T-21 U-04 T-21 U-05 T-21 U-06
T-22 U-04 T-22 U-05 T-22 U-06
T-23 U-04 T-23 U-05 T-23 U-06
T-24 U-04 T-24 U-05 T-24 U-06
T-25 U-04 T-25 U-05 T-25 U-06
T-26 U-04 T-26 U-05 T-26 U-06
T-01 U-07 T-01 U-08 T-01 U-09
T-02 U-07 T-02 U-08 T-02 U-09
T-03 U-07 T-03 U-08 T-03 U-09
T-04 U-07 T-04 U-08 T-04 U-09
T-05 U-07 T-05 U-08 T-05 U-09
T-06 U-07 T-06 U-08 T-06 U-09
T-07 U-07 T-07 U-08 T-07 U-09
T-08 U-07 T-08 U-08 T-08 U-09
T-09 U-07 T-09 U-08 T-09 U-09
T-10 U-07 T-10 U-08 T-10 U-09
T-11 U-07 T-11 U-08 T-11 U-09
T-12 U-07 T-12 U-08 T-12 U-09
T-13 U-07 T-13 U-08 T-13 U-09
T-14 U-07 T-14 U-08 T-14 U-09
T-15 U-07 T-15 U-08 T-15 U-09
T-16 U-07 T-16 U-08 T-16 U-09
T-17 U-07 T-17 U-08 T-17 U-09
T-18 U-07 T-18 U-08 T-18 U-09
T-19 U-07 T-19 U-08 T-19 U-09
T-20 U-07 T-20 U-08 T-20 U-09
T-21 U-07 T-21 U-08 T-21 U-09
T-22 U-07 T-22 U-08 T-22 U-09
T-23 U-07 T-23 U-08 T-23 U-09
T-24 U-07 T-24 U-08 T-24 U-09
T-25 U-07 T-25 U-08 T-25 U-09
T-26 U-07 T-26 U-08 T-26 U-09
――――――― ――――――― ――――――― For example, in Table 1, R 2 is T-01, R 6 is U-01, R 4 is 4,5-dihydrooxazol-2-yl, (Z) m1 is 2-OMe- When it is 5-F, it represents the following compounds.
[Table 1]
Conditions: R 4 is 4,5-dihydrooxazol-2-yl and (Z) m1 is 2-OMe-5-F.
――――――― ――――――― ―――――――
R2R6 R2R6 R2R6 _ _ _
――――――― ――――――― ―――――――
T-01 U-01 T-01 U-02 T-01 U-03
T-02 U-01 T-02 U-02 T-02 U-03
T-03 U-01 T-03 U-02 T-03 U-03
T-04 U-01 T-04 U-02 T-04 U-03
T-05 U-01 T-05 U-02 T-05 U-03
T-06 U-01 T-06 U-02 T-06 U-03
T-07 U-01 T-07 U-02 T-07 U-03
T-08 U-01 T-08 U-02 T-08 U-03
T-09 U-01 T-09 U-02 T-09 U-03
T-10 U-01 T-10 U-02 T-10 U-03
T-11 U-01 T-11 U-02 T-11 U-03
T-12 U-01 T-12 U-02 T-12 U-03
T-13 U-01 T-13 U-02 T-13 U-03
T-14 U-01 T-14 U-02 T-14 U-03
T-15 U-01 T-15 U-02 T-15 U-03
T-16 U-01 T-16 U-02 T-16 U-03
T-17 U-01 T-17 U-02 T-17 U-03
T-18 U-01 T-18 U-02 T-18 U-03
T-19 U-01 T-19 U-02 T-19 U-03
T-20 U-01 T-20 U-02 T-20 U-03
T-21 U-01 T-21 U-02 T-21 U-03
T-22 U-01 T-22 U-02 T-22 U-03
T-23 U-01 T-23 U-02 T-23 U-03
T-24 U-01 T-24 U-02 T-24 U-03
T-25 U-01 T-25 U-02 T-25 U-03
T-26 U-01 T-26 U-02 T-26 U-03
T-01 U-04 T-01 U-05 T-01 U-06
T-02 U-04 T-02 U-05 T-02 U-06
T-03 U-04 T-03 U-05 T-03 U-06
T-04 U-04 T-04 U-05 T-04 U-06
T-05 U-04 T-05 U-05 T-05 U-06
T-06 U-04 T-06 U-05 T-06 U-06
T-07 U-04 T-07 U-05 T-07 U-06
T-08 U-04 T-08 U-05 T-08 U-06
T-09 U-04 T-09 U-05 T-09 U-06
T-10 U-04 T-10 U-05 T-10 U-06
T-11 U-04 T-11 U-05 T-11 U-06
T-12 U-04 T-12 U-05 T-12 U-06
T-13 U-04 T-13 U-05 T-13 U-06
T-14 U-04 T-14 U-05 T-14 U-06
T-15 U-04 T-15 U-05 T-15 U-06
T-16 U-04 T-16 U-05 T-16 U-06
T-17 U-04 T-17 U-05 T-17 U-06
T-18 U-04 T-18 U-05 T-18 U-06
T-19 U-04 T-19 U-05 T-19 U-06
T-20 U-04 T-20 U-05 T-20 U-06
T-21 U-04 T-21 U-05 T-21 U-06
T-22 U-04 T-22 U-05 T-22 U-06
T-23 U-04 T-23 U-05 T-23 U-06
T-24 U-04 T-24 U-05 T-24 U-06
T-25 U-04 T-25 U-05 T-25 U-06
T-26 U-04 T-26 U-05 T-26 U-06
T-01 U-07 T-01 U-08 T-01 U-09
T-02 U-07 T-02 U-08 T-02 U-09
T-03 U-07 T-03 U-08 T-03 U-09
T-04 U-07 T-04 U-08 T-04 U-09
T-05 U-07 T-05 U-08 T-05 U-09
T-06 U-07 T-06 U-08 T-06 U-09
T-07 U-07 T-07 U-08 T-07 U-09
T-08 U-07 T-08 U-08 T-08 U-09
T-09 U-07 T-09 U-08 T-09 U-09
T-10 U-07 T-10 U-08 T-10 U-09
T-11 U-07 T-11 U-08 T-11 U-09
T-12 U-07 T-12 U-08 T-12 U-09
T-13 U-07 T-13 U-08 T-13 U-09
T-14 U-07 T-14 U-08 T-14 U-09
T-15 U-07 T-15 U-08 T-15 U-09
T-16 U-07 T-16 U-08 T-16 U-09
T-17 U-07 T-17 U-08 T-17 U-09
T-18 U-07 T-18 U-08 T-18 U-09
T-19 U-07 T-19 U-08 T-19 U-09
T-20 U-07 T-20 U-08 T-20 U-09
T-21 U-07 T-21 U-08 T-21 U-09
T-22 U-07 T-22 U-08 T-22 U-09
T-23 U-07 T-23 U-08 T-23 U-09
T-24 U-07 T-24 U-08 T-24 U-09
T-25 U-07 T-25 U-08 T-25 U-09
T-26 U-07 T-26 U-08 T-26 U-09
――――――― ――――――― ―――――――
――――――― ――――――― ―――――――
R2 R6 R2 R6 R2 R6
――――――― ――――――― ―――――――
T-01 U-01 T-01 U-02 T-01 U-03
T-02 U-01 T-02 U-02 T-02 U-03
T-03 U-01 T-03 U-02 T-03 U-03
T-04 U-01 T-04 U-02 T-04 U-03
T-05 U-01 T-05 U-02 T-05 U-03
T-06 U-01 T-06 U-02 T-06 U-03
T-07 U-01 T-07 U-02 T-07 U-03
T-08 U-01 T-08 U-02 T-08 U-03
T-09 U-01 T-09 U-02 T-09 U-03
T-10 U-01 T-10 U-02 T-10 U-03
T-11 U-01 T-11 U-02 T-11 U-03
T-12 U-01 T-12 U-02 T-12 U-03
T-13 U-01 T-13 U-02 T-13 U-03
T-14 U-01 T-14 U-02 T-14 U-03
T-15 U-01 T-15 U-02 T-15 U-03
T-16 U-01 T-16 U-02 T-16 U-03
T-17 U-01 T-17 U-02 T-17 U-03
T-18 U-01 T-18 U-02 T-18 U-03
T-19 U-01 T-19 U-02 T-19 U-03
T-20 U-01 T-20 U-02 T-20 U-03
T-21 U-01 T-21 U-02 T-21 U-03
T-22 U-01 T-22 U-02 T-22 U-03
T-23 U-01 T-23 U-02 T-23 U-03
T-24 U-01 T-24 U-02 T-24 U-03
T-25 U-01 T-25 U-02 T-25 U-03
T-26 U-01 T-26 U-02 T-26 U-03
T-01 U-04 T-01 U-05 T-01 U-06
T-02 U-04 T-02 U-05 T-02 U-06
T-03 U-04 T-03 U-05 T-03 U-06
T-04 U-04 T-04 U-05 T-04 U-06
T-05 U-04 T-05 U-05 T-05 U-06
T-06 U-04 T-06 U-05 T-06 U-06
T-07 U-04 T-07 U-05 T-07 U-06
T-08 U-04 T-08 U-05 T-08 U-06
T-09 U-04 T-09 U-05 T-09 U-06
T-10 U-04 T-10 U-05 T-10 U-06
T-11 U-04 T-11 U-05 T-11 U-06
T-12 U-04 T-12 U-05 T-12 U-06
T-13 U-04 T-13 U-05 T-13 U-06
T-14 U-04 T-14 U-05 T-14 U-06
T-15 U-04 T-15 U-05 T-15 U-06
T-16 U-04 T-16 U-05 T-16 U-06
T-17 U-04 T-17 U-05 T-17 U-06
T-18 U-04 T-18 U-05 T-18 U-06
T-19 U-04 T-19 U-05 T-19 U-06
T-20 U-04 T-20 U-05 T-20 U-06
T-21 U-04 T-21 U-05 T-21 U-06
T-22 U-04 T-22 U-05 T-22 U-06
T-23 U-04 T-23 U-05 T-23 U-06
T-24 U-04 T-24 U-05 T-24 U-06
T-25 U-04 T-25 U-05 T-25 U-06
T-26 U-04 T-26 U-05 T-26 U-06
T-01 U-07 T-01 U-08 T-01 U-09
T-02 U-07 T-02 U-08 T-02 U-09
T-03 U-07 T-03 U-08 T-03 U-09
T-04 U-07 T-04 U-08 T-04 U-09
T-05 U-07 T-05 U-08 T-05 U-09
T-06 U-07 T-06 U-08 T-06 U-09
T-07 U-07 T-07 U-08 T-07 U-09
T-08 U-07 T-08 U-08 T-08 U-09
T-09 U-07 T-09 U-08 T-09 U-09
T-10 U-07 T-10 U-08 T-10 U-09
T-11 U-07 T-11 U-08 T-11 U-09
T-12 U-07 T-12 U-08 T-12 U-09
T-13 U-07 T-13 U-08 T-13 U-09
T-14 U-07 T-14 U-08 T-14 U-09
T-15 U-07 T-15 U-08 T-15 U-09
T-16 U-07 T-16 U-08 T-16 U-09
T-17 U-07 T-17 U-08 T-17 U-09
T-18 U-07 T-18 U-08 T-18 U-09
T-19 U-07 T-19 U-08 T-19 U-09
T-20 U-07 T-20 U-08 T-20 U-09
T-21 U-07 T-21 U-08 T-21 U-09
T-22 U-07 T-22 U-08 T-22 U-09
T-23 U-07 T-23 U-08 T-23 U-09
T-24 U-07 T-24 U-08 T-24 U-09
T-25 U-07 T-25 U-08 T-25 U-09
T-26 U-07 T-26 U-08 T-26 U-09
――――――― ――――――― ――――――― For example, in Table 1, R 2 is T-01, R 6 is U-01, R 4 is 4,5-dihydrooxazol-2-yl, (Z) m1 is 2-OMe- When it is 5-F, it represents the following compounds.
――――――― ――――――― ―――――――
R2R6 R2R6 R2R6 _ _ _
――――――― ――――――― ―――――――
T-01 U-01 T-01 U-02 T-01 U-03
T-02 U-01 T-02 U-02 T-02 U-03
T-03 U-01 T-03 U-02 T-03 U-03
T-04 U-01 T-04 U-02 T-04 U-03
T-05 U-01 T-05 U-02 T-05 U-03
T-06 U-01 T-06 U-02 T-06 U-03
T-07 U-01 T-07 U-02 T-07 U-03
T-08 U-01 T-08 U-02 T-08 U-03
T-09 U-01 T-09 U-02 T-09 U-03
T-10 U-01 T-10 U-02 T-10 U-03
T-11 U-01 T-11 U-02 T-11 U-03
T-12 U-01 T-12 U-02 T-12 U-03
T-13 U-01 T-13 U-02 T-13 U-03
T-14 U-01 T-14 U-02 T-14 U-03
T-15 U-01 T-15 U-02 T-15 U-03
T-16 U-01 T-16 U-02 T-16 U-03
T-17 U-01 T-17 U-02 T-17 U-03
T-18 U-01 T-18 U-02 T-18 U-03
T-19 U-01 T-19 U-02 T-19 U-03
T-20 U-01 T-20 U-02 T-20 U-03
T-21 U-01 T-21 U-02 T-21 U-03
T-22 U-01 T-22 U-02 T-22 U-03
T-23 U-01 T-23 U-02 T-23 U-03
T-24 U-01 T-24 U-02 T-24 U-03
T-25 U-01 T-25 U-02 T-25 U-03
T-26 U-01 T-26 U-02 T-26 U-03
T-01 U-04 T-01 U-05 T-01 U-06
T-02 U-04 T-02 U-05 T-02 U-06
T-03 U-04 T-03 U-05 T-03 U-06
T-04 U-04 T-04 U-05 T-04 U-06
T-05 U-04 T-05 U-05 T-05 U-06
T-06 U-04 T-06 U-05 T-06 U-06
T-07 U-04 T-07 U-05 T-07 U-06
T-08 U-04 T-08 U-05 T-08 U-06
T-09 U-04 T-09 U-05 T-09 U-06
T-10 U-04 T-10 U-05 T-10 U-06
T-11 U-04 T-11 U-05 T-11 U-06
T-12 U-04 T-12 U-05 T-12 U-06
T-13 U-04 T-13 U-05 T-13 U-06
T-14 U-04 T-14 U-05 T-14 U-06
T-15 U-04 T-15 U-05 T-15 U-06
T-16 U-04 T-16 U-05 T-16 U-06
T-17 U-04 T-17 U-05 T-17 U-06
T-18 U-04 T-18 U-05 T-18 U-06
T-19 U-04 T-19 U-05 T-19 U-06
T-20 U-04 T-20 U-05 T-20 U-06
T-21 U-04 T-21 U-05 T-21 U-06
T-22 U-04 T-22 U-05 T-22 U-06
T-23 U-04 T-23 U-05 T-23 U-06
T-24 U-04 T-24 U-05 T-24 U-06
T-25 U-04 T-25 U-05 T-25 U-06
T-26 U-04 T-26 U-05 T-26 U-06
T-01 U-07 T-01 U-08 T-01 U-09
T-02 U-07 T-02 U-08 T-02 U-09
T-03 U-07 T-03 U-08 T-03 U-09
T-04 U-07 T-04 U-08 T-04 U-09
T-05 U-07 T-05 U-08 T-05 U-09
T-06 U-07 T-06 U-08 T-06 U-09
T-07 U-07 T-07 U-08 T-07 U-09
T-08 U-07 T-08 U-08 T-08 U-09
T-09 U-07 T-09 U-08 T-09 U-09
T-10 U-07 T-10 U-08 T-10 U-09
T-11 U-07 T-11 U-08 T-11 U-09
T-12 U-07 T-12 U-08 T-12 U-09
T-13 U-07 T-13 U-08 T-13 U-09
T-14 U-07 T-14 U-08 T-14 U-09
T-15 U-07 T-15 U-08 T-15 U-09
T-16 U-07 T-16 U-08 T-16 U-09
T-17 U-07 T-17 U-08 T-17 U-09
T-18 U-07 T-18 U-08 T-18 U-09
T-19 U-07 T-19 U-08 T-19 U-09
T-20 U-07 T-20 U-08 T-20 U-09
T-21 U-07 T-21 U-08 T-21 U-09
T-22 U-07 T-22 U-08 T-22 U-09
T-23 U-07 T-23 U-08 T-23 U-09
T-24 U-07 T-24 U-08 T-24 U-09
T-25 U-07 T-25 U-08 T-25 U-09
T-26 U-07 T-26 U-08 T-26 U-09
――――――― ――――――― ―――――――
第2表は、第1表におけるR4および(Z)m1に関する条件が別の条件に置き換えられていることを除き、それぞれが第1表と同様に構成されている第1-02表から第1-21表のリストである。
Table 2 contains Tables 1-02 through Tables 1-02, each constructed similarly to Table 1, except that the conditions for R 4 and (Z) m1 in Table 1 have been replaced with different conditions. 1-21 table.
例えば、第1-02表は、第1表の条件(すなわち、「R4は4,5-ジヒドロオキサゾール-2-イルであり、(Z)m1は2-OMe-5-Fである。」)が、第2表中の第1-02表の行の条件(すなわち、「R4はメトキシメチルであり、(Z)m1は2-OMe-5-Fである。」)に置き換えられていることを除き、第1表と同様に構成されている。
For example, Table 1-02 applies the conditions of Table 1 (ie, "R 4 is 4,5-dihydrooxazol-2-yl and (Z) m1 is 2-OMe-5-F."). ) is replaced by the condition of row Table 1-02 in Table 2 (i.e., "R 4 is methoxymethyl and (Z) m1 is 2-OMe-5-F.") It is structured the same as Table 1, except that
すなわち、第2表中の第1-02表に記載の「条件」は、R4はメトキシメチルであり、(Z)m1は2-OMe-5-Fである式(X)で表される化合物を表す。第1-03表~第1-21表も同様に構成されている。
That is, the “conditions” described in Table 1-02 in Table 2 are represented by the formula (X) in which R 4 is methoxymethyl and (Z) m1 is 2-OMe-5-F represents a compound. Tables 1-03 to 1-21 are structured similarly.
なお、第2表中「(Z)m1は無置換である」の表記は、式(X)で表される化合物において、(Z)m1を有し得るフェニル基が無置換であることを表す。
The notation "(Z) m1 is unsubstituted" in Table 2 indicates that the phenyl group that may have (Z) m1 in the compound represented by formula (X) is unsubstituted. .
[第2表]
表 条件
―――――――――――――――――――――――――――――――
第1-02表 R4はメトキシメチルであり、
(Z)m1は2-OMe-5-Fである。
第1-03表 R4は-C≡CMeであり、
(Z)m1は2-OMe-5-Fである。
第1-04表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は無置換である。
第1-05表 R4はメトキシメチルであり、
(Z)m1は無置換である。
第1-06表 R4は-C≡CMeであり、
(Z)m1は無置換である。
第1-07表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は2-OMeである。
第1-08表 R4はメトキシメチルであり、
(Z)m1は2-OMeである。
第1-09表 R4は-C≡CMeであり、
(Z)m1は2-OMeである。
第1-10表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は2-OEtである。
第1-11表 R4はメトキシメチルであり、
(Z)m1は2-OEtである。
第1-12表 R4は-C≡CMeであり、
(Z)m1は2-OEtである。
第1-13表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は3-Fである。
第1-14表 R4はメトキシメチルであり、
(Z)m1は3-Fである。
第1-15表 R4は-C≡CMeであり、
(Z)m1は3-Fである。
第1-16表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は3-Meである。
第1-17表 R4はメトキシメチルであり、
(Z)m1は3-Meである。
第1-18表 R4は-C≡CMeであり、
(Z)m1は3-Meである。
第1-19表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は3-Clである。
第1-20表 R4はメトキシメチルであり、
(Z)m1は3-Clである。
第1-21表 R4は-C≡CMeであり、
(Z)m1は3-Clである。
――――――――――――――――――――――――――――――― [Table 2]
Table Conditions ――――――――――――――――――――――――――――――
Table 1-02 R 4 is methoxymethyl,
(Z) m1 is 2-OMe-5-F.
Table 1-03 R 4 is -C≡CMe,
(Z) m1 is 2-OMe-5-F.
Table 1-04 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is unsubstituted.
Table 1-05 R 4 is methoxymethyl,
(Z) m1 is unsubstituted.
Table 1-06 R 4 is -C≡CMe,
(Z) m1 is unsubstituted.
Table 1-07 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 2-OMe.
Table 1-08 R 4 is methoxymethyl,
(Z) m1 is 2-OMe.
Table 1-09 R 4 is -C≡CMe,
(Z) m1 is 2-OMe.
Table 1-10 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 2-OEt.
Table 1-11 R 4 is methoxymethyl,
(Z) m1 is 2-OEt.
Table 1-12 R 4 is -C≡CMe,
(Z) m1 is 2-OEt.
Table 1-13 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 3-F.
Table 1-14 R 4 is methoxymethyl,
(Z) m1 is 3-F.
Table 1-15 R 4 is -C≡CMe,
(Z) m1 is 3-F.
Table 1-16 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 3-Me.
Table 1-17 R 4 is methoxymethyl,
(Z) m1 is 3-Me.
Table 1-18 R 4 is -C≡CMe,
(Z) m1 is 3-Me.
Table 1-19 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 3-Cl.
Table 1-20 R 4 is methoxymethyl,
(Z) m1 is 3-Cl.
Table 1-21 R 4 is -C≡CMe,
(Z) m1 is 3-Cl.
―――――――――――――――――――――――――――――――
表 条件
―――――――――――――――――――――――――――――――
第1-02表 R4はメトキシメチルであり、
(Z)m1は2-OMe-5-Fである。
第1-03表 R4は-C≡CMeであり、
(Z)m1は2-OMe-5-Fである。
第1-04表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は無置換である。
第1-05表 R4はメトキシメチルであり、
(Z)m1は無置換である。
第1-06表 R4は-C≡CMeであり、
(Z)m1は無置換である。
第1-07表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は2-OMeである。
第1-08表 R4はメトキシメチルであり、
(Z)m1は2-OMeである。
第1-09表 R4は-C≡CMeであり、
(Z)m1は2-OMeである。
第1-10表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は2-OEtである。
第1-11表 R4はメトキシメチルであり、
(Z)m1は2-OEtである。
第1-12表 R4は-C≡CMeであり、
(Z)m1は2-OEtである。
第1-13表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は3-Fである。
第1-14表 R4はメトキシメチルであり、
(Z)m1は3-Fである。
第1-15表 R4は-C≡CMeであり、
(Z)m1は3-Fである。
第1-16表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は3-Meである。
第1-17表 R4はメトキシメチルであり、
(Z)m1は3-Meである。
第1-18表 R4は-C≡CMeであり、
(Z)m1は3-Meである。
第1-19表 R4は4,5-ジヒドロオキサゾール-2-イルであり、
(Z)m1は3-Clである。
第1-20表 R4はメトキシメチルであり、
(Z)m1は3-Clである。
第1-21表 R4は-C≡CMeであり、
(Z)m1は3-Clである。
――――――――――――――――――――――――――――――― [Table 2]
Table Conditions ――――――――――――――――――――――――――――――
Table 1-02 R 4 is methoxymethyl,
(Z) m1 is 2-OMe-5-F.
Table 1-03 R 4 is -C≡CMe,
(Z) m1 is 2-OMe-5-F.
Table 1-04 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is unsubstituted.
Table 1-05 R 4 is methoxymethyl,
(Z) m1 is unsubstituted.
Table 1-06 R 4 is -C≡CMe,
(Z) m1 is unsubstituted.
Table 1-07 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 2-OMe.
Table 1-08 R 4 is methoxymethyl,
(Z) m1 is 2-OMe.
Table 1-09 R 4 is -C≡CMe,
(Z) m1 is 2-OMe.
Table 1-10 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 2-OEt.
Table 1-11 R 4 is methoxymethyl,
(Z) m1 is 2-OEt.
Table 1-12 R 4 is -C≡CMe,
(Z) m1 is 2-OEt.
Table 1-13 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 3-F.
Table 1-14 R 4 is methoxymethyl,
(Z) m1 is 3-F.
Table 1-15 R 4 is -C≡CMe,
(Z) m1 is 3-F.
Table 1-16 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 3-Me.
Table 1-17 R 4 is methoxymethyl,
(Z) m1 is 3-Me.
Table 1-18 R 4 is -C≡CMe,
(Z) m1 is 3-Me.
Table 1-19 R 4 is 4,5-dihydrooxazol-2-yl,
(Z) m1 is 3-Cl.
Table 1-20 R 4 is methoxymethyl,
(Z) m1 is 3-Cl.
Table 1-21 R 4 is -C≡CMe,
(Z) m1 is 3-Cl.
―――――――――――――――――――――――――――――――
本発明化合物の農薬として許容される塩としては、例えば、塩酸塩、臭化水素酸塩、ヨウ化水素酸塩、ギ酸塩、酢酸塩又はシュウ酸塩が挙げられる。
Examples of agriculturally acceptable salts of the compound of the present invention include hydrochloride, hydrobromide, hydroiodide, formate, acetate or oxalate.
本発明化合物は、一般的には農園芸用の殺菌・殺かび剤として、ネコブカビ類、卵菌類、接合菌類、子嚢菌類、担子菌類、不完全菌類、細菌類又はウイルスによる種々の病害に対し使用することができる。
The compound of the present invention is generally used as an agricultural and horticultural bactericidal and fungicidal agent against various diseases caused by Necrophytes, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, Bacteria or viruses. can be used.
「病原菌」とは、植物の病害の病原となる微生物を意味し、具体的には、以下の微生物が挙げられるが、これらに限定されるものではない。
Taphrina spp.(例えば、Taphrina deformans、T. pruni等)、Pneumocystis spp.、Geotrichum spp.、Candida spp.(例えば、Candida albicans、C. sorbosa等)、Pichia spp.(例えば、Pichia kluyveri等)、Capnodium spp.、Fumago spp.、Hypocapnodium spp.、Cercospora spp.(例えば、Cercospora apii、C. asparagi、C. beticola、C. capsici、C. carotae、C. kaki、C. kikuchii、C. zonata等)、Cercosporidium spp.、Cladosporium spp.(例えば、Cladosporium colocasiae、C. cucumerinum、C. variabile等)、Davidiella spp.、Didymosporium spp.、Heterosporium spp.(例えば、Heterosporium allii等)、Mycosphaerella spp.(例えば、Mycosphaerella arachidis、M. berkeleyi、M. cerasella、M. fijiensis、M. fragariae、M. graminicola、M. nawae、M. pinodes、M. pomi、M. zingiberis等)、Mycovellosiella spp.(例えば、Mycovellosiella fulva、M. nattrassii等)、Paracercospora spp.(例えば、Paracercospora egenula等)、Phaeoisariopsis spp.、Phaeoramularia spp.、Pseudocercospora spp.(例えば、Pseudocercospora abelmoschi、P. fuligena、P. vitis等)、Pseudocercosporella spp.(例えば、Pseudocercosporella capsellae等)、Ramichloridium spp.、Ramularia spp.、Septogloeum spp.、Septoria spp.(例えば、Septoria albopunctata、S. apiicola、S. chrysanthemella、S. helianthi、S. obesa等)、Sphaerulina spp.、Aureobasidium spp.、Kabatiella spp.、Plowrightia spp.、Stigmina spp.、Elsinoe spp.(例えば、Elsinoe ampelina、E. araliae、E. fawcettii等)、Sphaceloma spp.(例えば、Sphaceloma caricae等)、Ascochyta spp.(例えば、Ascochyta pisi等)、Corynespora spp.(例えば、Corynespora cassiicola等)、Leptosphaeria spp.(例えば、Leptosphaeria coniothyrium、L. maculans等)、Saccharicola spp.、Phaeosphaeria spp. (例えば、Phaeosphaeria nodorum等)、Ophiosphaerella spp.、Setophoma spp.、Helminthosporium spp.、Alternaria spp.(例えば、Alternaria alternata、A. brassicae、A. brassicicola、A. citri、A. dauci、A. helianthi、A. japonica、A. kikuchiana、A. mali、A. panax、A. porri、A. radicina、A. solani等)、Bipolaris spp.(例えば、Bipolaris sorghicola等)、Cochliobolus spp.(例えば、Cochliobolus heterostrophus、C. lunatus、C. miyabeanus等)、Curvularia spp.(例えば、Curvularia geniculata、C. verruculosa等)、Drechslera spp.、Pleospora spp.(例えば、Pleospora herbarum等)、Pyrenophora spp.(例えば、Pyrenophora graminea、P. teres等)、Setosphaeria spp.(例えば、Setosphaeria turcica等)、Stemphylium spp.(例えば、Stemphylium botryosum、S. lycopersici、S. solani、S. vesicarium等)、Fusicladium spp.、Venturia spp.(例えば、Venturia carpophila、V. Inaequalis、V. nashicola、V. pirina等)、Didymella spp.(例えば、Didymella bryoniae、D. fabae等)、Hendersonia spp.、Phoma spp.(例えば、Phoma erratica var. mikan、P. exigua var. exigua、P. wasabiae等)、Pyrenochaeta spp.(例えば、Pyrenochaeta lycopersici等)、Stagonospora spp.(例えば、Stagonospora sacchari等)、Botryosphaeria spp.(例えば、Botryosphaeria berengeriana f. sp. piricola、B. dothidea等)、Dothiorella spp.、Fusicoccum spp.、Guignardia spp.、Lasiodiplodia spp.(例えば、Lasiodiplodia theobromae等)、Macrophoma spp.、Macrophomina spp.、Neofusicoccum spp.、Phyllosticta spp.(例えば、Phyllosticta zingiberis等)、Schizothyrium spp.(例えば、Schizothyrium pomi等)、Acrospermum spp.、Leptosphaerulina spp.、Aspergillus spp.、Penicillium spp.(例えば、Penicillium digitatum、P. italicum、P. sclerotigenum等)、Microsporum spp.、Trichophyton spp.(例えば、Trichophyton mentagrophytes、T. rubrum等)、Histoplasma spp.、Blumeria spp.(例えば、Blumeria graminis f. sp. hordei、B. g. f. sp. tritici等)、Erysiphe spp.(例えば、Erysiphe betae、E. cichoracearum、E. c. var. cichoracearum、E. heraclei、E. pisi等)、Golovinomyces spp.(例えば、Golovinomyces cichoracearum var. latisporus等)、Leveillula spp.(例えば、Leveillula taurica等)、Microsphaera spp.、Oidium spp.(例えば、Oidium neolycopersici等)、Phyllactinia spp.(例えば、Phyllactinia kakicola、P. mali、P. moricola等)、Podosphaera spp.(例えば、Podosphaera fusca、P. leucotricha、P. pannosa、P. tridactyla var. tridactyla、P. xanthii等)、Sphaerotheca spp.(例えば、Sphaerotheca aphanis var. aphanis、S. fuliginea等)、Uncinula spp.(例えば、Uncinula necator、U. n. var. necator等)、Uncinuliella spp.(例えば、Uncinuliella simulans var. simulans、U. s. var. tandae等)、Blumeriella spp.(例えば、Blumeriella jaapii等)、Cylindrosporium spp.、Diplocarpon spp.(例えば、Diplocarpon mali、D. mespili、D. rosae等)、Gloeosporium spp.(例えば、Gloeosporium minus等)、Marssonina spp.、Tapesia spp.(例えば、Tapesia acuformis、T. yallundae等)、Lachnum spp.、Scleromitrula spp.、Botryotinia spp.(例えば、Botryotinia fuckeliana等)、Botrytis spp.(例えば、Botrytis allii、B. byssoidea、B. cinerea、B. elliptica、B. fabae、B. squamosa等)、Ciborinia spp.、Grovesinia spp.、Monilia mumecola、Monilinia spp.(例えば、Monilinia fructicola、M. fructigena、M. laxa、M. mali、M. vaccinii-corymbosi等)、Sclerotinia spp.(例えば、Sclerotinia borealis、S. homoeocarpa、S. minor、S. sclerotiorum等)、Valdensia spp.(例えば、Valdensia heterodoxa等)、Claviceps spp.(例えば、Claviceps sorghi、C. sorghicola等)、Epichloe spp.、Ephelis japonica、Villosiclava virens、Hypomyces spp.(例えば、Hypomyces solani f. sp. mori、H. s. f. sp. pisi等)、Trichoderma spp.(例えば、Trichoderma viride等)、Calonectria spp.(例えば、Calonectria ilicicola等)、Candelospora spp.、Cylindrocarpon spp.、Cylindrocladium spp.、Fusarium spp.(例えば、Fusarium arthrosporioides、F. crookwellense、F. culmorum、F. cuneirostrum、F. oxysporum、F. o. f. sp. adzukicola、F. o. f. sp. allii、F. o. f. sp. asparagi、F. o. f. sp. batatas、F. o. f. sp. cepae、F. o. f. sp. colocasiae、F. o. f. sp. conglutinans、F. o. f. sp. cubense、F. o. f. sp. cucumerinum、F. o. f. sp. fabae、F. o. f. sp. fragariae、F. o. f. sp. lactucae、F. o. f. sp. lagenariae、F. o. f. sp. lycopersici、F. o. f. sp. melongenae、F. o. f. sp. melonis、F. o. f. sp. nelumbinicola、F. o. f. sp. niveum、F. o. f. sp. radicis-lycopersici、F. o. f. sp. raphani、F. o. f. sp. spinaciae、F. sporotrichioides、F. solani、F. s. f. sp. cucurbitae、F. s. f. sp. eumartii、F. s. f. sp. glycines、F. s. f. sp. pisi、F. s. f. sp. Radicicola、F. virguliforme等)、Gibberella spp.(例えば、Gibberella avenacea、G. baccata、G. fujikuroi、G. zeae等)、Haematonectria spp.、Nectria spp.、Ophionectria spp.、Caldariomyces spp.、Myrothecium spp.、Trichothecium spp.、Verticillium spp.(例えば、Verticillium albo-atrum、V. dahliae、V. longisporum等)、Ceratocystis spp.(例えば、Ceratocystis ficicola, C. fimbriata等)、Thielaviopsis spp.(例えば、Thielaviopsis basicola等)、Adisciso spp.、Monochaetia spp.、Pestalotia spp.(例えば、Pestalotia eriobotrifolia等)、Pestalotiopsis spp.(例えば、Pestalotiopsis funerea、P. longiseta、P. neglecta、P. theae等)、Physalospora spp.、Nemania spp.、Nodulisporium spp.、Rosellinia spp.(例えば、Rosellinia necatrix等)、Monographella spp.(例えば、Monographella nivalis等)、Ophiostoma spp.、Cryphonectria spp.(例えば、Cryphonectria parasitica等)、Diaporthe spp.(例えば、Diaporthe citri、D. kyushuensis、D. nomurai、D. tanakae等)、Diaporthopsis spp.、Phomopsis spp.(例えば、Phomopsis asparagi、P. fukushii、P. obscurans、P. vexans等)、Cryptosporella spp.、Discula spp.(例えば、Discula theae-sinensis等)、Gnomonia spp.、Coniella spp.、Coryneum spp.、Greeneria spp.、Melanconis spp.、Cytospora spp.、Leucostoma spp.、Valsa spp.(例えば、Valsa ceratosperma等)、Tubakia spp.、Monosporascus spp.、Clasterosporium spp.、Gaeumannomyces spp.(例えば、Gaeumannomyces graminis等)、Magnaporthe spp.(例えば、Magnaporthe grisea等)、Pyricularia spp.(例えば、Pyricularia zingiberis等)、Monilochaetes infuscans、Colletotrichum spp.(例えば、Colletotrichum acutatum、C. capsici、C. cereale、C. destructivum、C. fragariae、C. lindemuthianum、C. nigrum、C. orbiculare、C. spinaciae等)、Glomerella spp.(例えば、Glomerella cingulata等)、Khuskia oryzae、Phyllachora spp.(例えば、Phyllachora pomigena等)、Ellisembia spp.、Briosia spp.、Cephalosporium spp.(例えば、Cephalosporium gramineum等)、Epicoccum spp.、Gloeocercospora sorghi、Mycocentrospora spp.、Peltaster spp.(例えば、Peltaster fructicola等)、Phaeocytostroma spp.、Phialophora spp.(例えば、Phialophora gregata等)、Pseudophloeosporella dioscoreae、Pseudoseptoria spp.、Rhynchosporium spp.(例えば、Rhynchosporium secalis等)、Sarocladium spp.、Coleophoma spp.、Helicoceras oryzae等の子嚢菌門(Ascomycota)の菌類。Septobasidium spp.(例えば、Septobasidium bogoriense、S. tanakae等)、Helicobasidium spp.(例えば、Helicobasidium longisporum等)、Coleosporium spp.(例えば、Coleosporium plectranthi等)、Cronartium spp.、Phakopsora spp.(例えば、Phakopsora artemisiae、P. nishidana、P. pachyrhizi等)、Physopella spp.(例えば、Physopella ampelopsidis等)、Kuehneola spp.(例えば、Kuehneola japonica等)、Phragmidium spp.(例えば、Phragmidium fusiforme、P. mucronatum、P. rosae-multiflorae等)、Gymnosporangium spp.(例えば、Gymnosporangium asiaticum、G. yamadae等)、Puccinia spp.(例えば、Puccinia allii、P. brachypodii var. poae-nemoralis、P. coronata、P. c. var. coronata、P. cynodontis、P. graminis、P. g. subsp. graminicola、P. hordei、P. horiana、P. kuehnii、P. melanocephala、P. recondita、P. striiformis var. striiformis、P. tanaceti var. tanaceti、P. tokyensis、P. zoysiae等)、Uromyces spp.(例えば、Uromyces phaseoli var. azukicola、U. p. var. phaseoli、Uromyces viciae-fabae var. viciae-fabae等)、Naohidemyces vaccinii、Nyssopsora spp.、Leucotelium spp.、Tranzschelia spp.(例えば、Tranzschelia discolor等)、Aecidium spp.、Blastospora spp.(例えば、Blastospora smilacis等)、Uredo spp.、Sphacelotheca spp.、Urocystis spp.、Sporisorium spp.(例えば、Sporisorium scitamineum等)、Ustilago spp.(例えば、Ustilago maydis、U. nuda等)、
Entyloma spp.、Exobasidium spp.(例えば、Exobasidium reticulatum、E. vexans等)、Microstroma spp.、Tilletia spp.(例えば、Tilletia caries、T. controversa、T. laevis等)、Itersonilia spp.(例えば、Itersonilia perplexans等)、Cryptococcus spp.、Bovista spp.(例えば、Bovista dermoxantha等)、Lycoperdon spp.(例えば、Lycoperdon curtisii、L. perlatum等)、Conocybe spp.(例えば、Conocybe apala等)、Marasmius spp.(例えば、Marasmius oreades 等)、Armillaria spp.、Helotium spp.、Lepista spp.(例えば、Lepista subnuda等)、Sclerotium spp.(例えば、Sclerotium cepivorum等)、Typhula spp.(例えば、Typhula incarnata、T. ishikariensis var. ishikariensis等)、Athelia spp.(例えば、Athelia rolfsii等)、Ceratobasidium spp.(例えば、Ceratobasidium cornigerum等)、Ceratorhiza spp.、Rhizoctonia spp.(例えば、Rhizoctonia solani等)、Thanatephorus spp.(例えば、Thanatephorus cucumeris等)、Laetisaria spp.、Waitea spp.、Fomitiporia spp.、Ganoderma spp.、Chondrostereum purpureum、Phanerochaete spp.等の担子菌門(Basidiomycota)の菌類。Olpidium spp.等のツボカビ門(Chitridiomycota)の菌類。Physoderma spp.等のコウマクノウキン門(Blastocladiomycota)の菌類。Choanephora spp.、Choanephoroidea cucurbitae、Mucor spp.(例えば、Mucor fragilis等)、Rhizopus spp.(例えば、Rhizopus arrhizus、R. chinensis、R. oryzae、R. stolonifer var. stolonifer等)等のケカビ亜門(Mucoromycotina)の菌類。Plasmodiophora spp.(例えば、Plasmodiophora brassicae等)、Spongospora subterranea f. sp. Subterranea等のケルコゾア門(Cercozoa)の原生生物。Aphanomyces spp.(例えば、Aphanomyces cochlioides、A. raphani等)、Albugo spp.(例えば、Albugo macrospora、A. wasabiae等)、Bremia spp.(例えば、Bremia lactucae等)、Hyaloperonospora spp.、Peronosclerospora spp.、Peronospora spp.(例えば、Peronospora alliariae-wasabi、P. chrysanthemi-coronarii、P. destructor、P. farinosa f. sp. spinaciae、P. manshurica、P. parasitica、P. sparsa等)、Plasmopara spp.(例えば、Plasmopara halstedii、P. nivea、P. viticola等)、Pseudoperonospora spp.(例えば、Pseudoperonospora cubensis等)、Sclerophthora spp.、Phytophthora spp.(例えば、Phytophthora cactorum、P. capsici、P. citricola、P. citrophthora、P. cryptogea、P. fragariae、P. infestans、P. melonis、P. nicotianae、P. palmivora、P. porri、P. sojae、P. syringae、P. vignae f. sp. adzukicola等)、Pythium spp.(例えば、Pythium afertile、P. aphanidermatum、P. apleroticum、P. aristosporum、P. arrhenomanes、P. buismaniae、P. debaryanum、P. graminicola、P. horinouchiense、P. irregulare、P. iwayamai、P. myriotylum、P. okanoganense、P. paddicum、P. paroecandrum、P. periplocum、P. spinosum、P. sulcatum、P. sylvaticum、P. ultimum var. ultimum、P. vanterpoolii、P. vexans、P. volutum等)等の不等毛植物門(Heterokontophyta)の卵菌類(Oomycetes)。Clavibacter spp.(例えば、Clavibacter michiganensis subsp. michiganensis等)、Curtobacterium spp.、Leifsonia spp.(例えば、Leifsonia xyli subsp. xyli等)、Streptomyces spp.(例えば、Streptomyces ipomoeae等)等の放線菌門(Actinobacteria)のグラム陽性菌類。Clostridium sp.等のフィルミクテス門(Firmicutes)のグラム陽性菌類。Phytoplasma等のテネリクテス門(Tenericutes)のグラム陽性菌類。Rhizobium spp.(例えば、Rhizobium radiobacter等)、Acetobacter spp.、Burkholderia spp.(例えば、Burkholderia andropogonis、B. cepacia、B. gladioli、B. glumae、B. plantarii等)、Acidovorax spp.(例えば、Acidovorax avenae subsp. avenae、A. a. subsp. citrulli、A. konjaci等)、Herbaspirillum spp.、Ralstonia spp.(例えば、Ralstonia solanacearum等)、Xanthomonas spp.(例えば、Xanthomonas albilineans、X. arboricola pv. pruni、X. axonopodis pv. vitians、X. campestris pv. campestris、X. c. pv. cucurbitae、X. c. pv. glycines、X. c. pv. mangiferaeindicae、X. c. pv. nigromaculans、X. c. pv. vesicatoria、X. citri subsp. citri、X. oryzae pv. oryzae等)、Pseudomonas spp.(例えば、Pseudomonas cichorii、P. fluorescens、P. marginalis、P. m. pv. marginalis、P. savastanoi pv. glycinea、P. syringae、P. s. pv. actinidiae、P. s. pv. eriobotryae、P. s. pv. helianthi、P. s. pv. lachrymans、P. s. pv. maculicola、P. s. pv. mori、P. s. pv. morsprunorum、P. s. pv. spinaciae、P. s. pv. syringae、P. s. pv. theae、P. viridiflava等)、Rhizobacter spp.、Brenneria spp.(例えば、Brenneria nigrifluens等)、Dickeya spp.(例えば、Dickeya dianthicola、D. zeae等)、Erwinia spp.(例えば、Erwinia amylovora、E. rhapontici等)、Pantoea spp.、Pectobacterium spp.(例えば、Pectobacterium atrosepticum、P. carotovorum、P. wasabiae等)等のプロテオバクテリア門(Proteobacteria)のグラム陰性菌類。 The term "pathogen" means microorganisms that cause plant diseases, and specifically includes, but is not limited to, the following microorganisms.
(eg, Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (eg, Candida albicans, C. sorbosa, etc.), Pichia spp. (eg, Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. Cercosporidium spp., Cladosporium spp. (e.g. Cladosporium colocasiae, C. cucumerinum, C. variabile etc.), Davidiella spp. , M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis, etc.), Mycovellosiella spp. nattrassii etc.), Paracercospora spp. (e.g. Paracercospora egenula etc.), Phaeoisariopsis spp., Phaeoramularia spp. etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp. , Septoria spp. (e.g. Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g. Elsinoe ampelina, E. araliae, E. fawcettii etc.), Sphaceloma spp. (e.g. Sphaceloma caricae etc.), Ascochyta spp. , Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp. alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc. ), Bipolaris spp. (e.g. Bipolaris sorghicola etc.), Cochliobolus spp. (e.g. Cochliobolus heterostrophus, C. lunatus, C. miyabeanus etc.), Curvularia spp. , Pleospora spp. (e.g. Pleospora herbarum etc.), Pyrenophora spp. nea, P. teres etc.), Setosphaeria spp. (e.g. Setosphaeria turcica etc.), Stemphylium spp. For example, Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina, etc.), Didymella spp. P. exigua var. exigua, P. wasabiae, etc.), Pyrenochaeta spp. (e.g., Pyrenochaeta lycopersici, etc.), Stagonospora spp. dothidea etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. , Schizothyrium spp. (eg, Schizothyrium pomi, etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. (eg, Penicillium digitatum, P. italicum, P. sclerotigenum, etc.), Microsporum spp., Trichophyton spp. (e.g., Trichophyton mentagrophytes, T rubrum etc.), Histoplasma spp., Blumeria spp. cichoracearum, E. heraclei, E. pisi, etc.), Golovinomyces spp. (e.g., Golovinomyces cichoracearum var. latisporus, etc.), Leveillula spp. etc.), Phyllactinia spp. (e.g. Phyllactinia kakicola, P. mali, P. moricola etc.), Podosphaera spp. ), Sphaerotheca spp. (e.g. Sphaerotheca aphanis var. aphanis, S. fuliginea etc.), Uncinula spp. , U. s. var. tandae etc.), Blumeriella spp. (e.g. Blumeriella jaapii etc.), Cylindrosporium spp. , Gloeosporium minus etc.), Marssonina spp., Tapesia spp. (e.g. Tapesia acuformis, T. yallundae etc.), Lachnum spp. ula spp., Botryotinia spp. (e.g. Botryotinia fuckeliana etc.), Botrytis spp. Grovesinia spp., Monilia mumecola, Monilinia spp. minor, S. sclerotiorum etc.), Valdensia spp. (e.g. Valdensia heterodoxa etc.), Claviceps spp. , Hypomyces solani f. sp. mori, H. s. f. sp. pisi, etc.), Trichoderma spp. (e.g., Trichoderma viride, etc.), Calonectria spp. , Fusarium spp. (e.g., Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. o. f. sp. adzukicola, F. o. f. sp. allii, F. o. f. sp. asparagi, F. sp. batatas, F.o.f.sp.cepae, F.o.f.sp.colocasiae, F.o.f.sp.conglutinans, F.o.f.s p. cubense, F. o. f. sp. cucumerinum, F. o. f. sp. fabae, F. o. f. sp. fragariae, F. o. f. sp. lactucae, F. o. f. sp. melonis, F. o. f. sp. nelumbinicola, F. o. f. sp. niveum, F. o. f. sp. radicis-lycopersici, F. o. f. sp. sp. cucurbitae, F. s. f. sp. eumartii, F. s. f. sp. glycines, F. s. f. sp. pisi, F. s. f. sp. Radicicola, F. virguliforme, etc.), Gibberella spp. For example, Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. albo-atrum, V. dahliae, V. longisporum etc.), Ceratocystis spp. (e.g. Ceratocystis ficicola, C. fimbriata etc.), Thielaviopsis spp. (e.g., Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp. (e.g., Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.), Physalospora spp., Nemania spp., Nodulisporium spp., Roselinia spp. (e.g., Roselinia necatrix etc.), Monographella spp. spp. (e.g. Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae etc.), Diaporthopsis spp., Phomopsis spp. spp., Discula spp. (e.g., Discula theae-sinensis etc.), Gnomonia spp., Coniella spp., Coryneum spp., Greeneria spp. Valsa ceratosperma etc.), Tubakia spp., Monosporascus spp., Clusterosporium spp., Gaeumannomyces spp. (e.g. Gaeumannomyces graminis etc.), Magnaporthe spp. Monilochaetes infuscans, Colletotrichum spp. Glomerella cingulata, etc.), Khuskia ory zae, Phyllachora spp. (e.g. Phyllachora pomigena etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. fructicola etc.), Phaeocytostroma spp., Phialophora spp. Fungi of the phylum Ascomycota. Septobasidium spp. (e.g. Septobasidium bogoriense, S. tanakae etc.), Helicobasidium spp. (e.g. Helicobasidium longisporum etc.), Coleosporium spp. P. nishidana, P. pachyrhizi etc.), Physopella spp. (e.g. Physopella ampelopsidis etc.), Kuehneola spp. (e.g. Kuehneola japonica etc.), Phragmidium spp. etc.), Gymnosporangium spp. (e.g. Gymnosporangium asiaticum, G. yamadae etc.), Puccinia spp. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P. tanaceti var. tokyensis, P.zoysiae, etc.), Uromyces spp. (e.g., Uromyces phaseoli var. azukicola, U.p. var. phaseoli, Uromyces viciae-fabae var. , Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (e.g., Sporisorium scitamineum, etc.), Ustilago spp. ),
Entyloma spp., Exobasidium spp. (e.g. Exobasidium reticulatum, E. vexans, etc.), Microstroma spp., Tilletia spp. etc.), Cryptococcus spp., Bovista spp. (e.g., Bovista dermoxantha etc.), Lycoperdon spp. Marasmius oreades etc.), Armillaria spp., Helotium spp., Lepista spp. (e.g. Lepista subnuda etc.), Sclerotium spp. etc.), Athelia spp. (e.g. Athelia rolfsii etc.), Ceratobasidium spp. , Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaete spp. Fungi of the phylum Chitridiomycota, such as Olpidium spp. Fungi of the phylum Blastocladiomycota, such as Physoderma spp. Mucoromycotina such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis), Rhizopus spp. ) fungi. Protists of the phylum Cercozoa, such as Plasmodiophora spp. (eg Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea. Aphanomyces spp. (e.g. Aphanomyces cochlioides, A. raphani etc.), Albugo spp. (e.g. Albugo macrospora, A. wasabiae etc.), Bremia spp. spp. halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (e.g., Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. , Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P. debaryanum, P. graminicola, P. horinouchiense, P. irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, Oomycetes of Heterokontophyta, such as P. ultimum var. ultimum, P. vanterpoolii, P. vexans, P. volutum, etc.). Actinobacteria such as Clavibacter spp. (e.g. Clavibacter michiganensis subsp. michiganensis), Curtobacterium spp., Leifsonia spp. of Gram-positive bacteria. Gram-positive fungi of the phylum Firmicutes, such as Clostridium sp. Gram-positive fungi of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp. (e.g. Rhizobium radiobacter etc.), Acetobacter spp., Burkholderia spp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (e.g., Ralstonia solanacearum, etc.), Xanthomonas spp. vitians, X. campestris pv. campestris, X. c. pv. cucurbitae, X. c. pv. glycines, X. c. pv. vesicatoria, X. citri subsp. citri, X. oryzae pv. oryzae, etc.), Pseudomonas spp. , P. syringae, P. s. pv. actinidiae, P. s. pv. eriobotryae, P. s. pv. helianthi, P. s. pv. mori, P. s. pv. morsprunorum, P. s. pv. spinaciae, P. s. pv. syringae, P. s. pv. theae, P. viridiflava, etc.), Rhizobacter spp., Brenneria spp. , Brenneria nigrifluens, etc.), Dick eya spp. (e.g. Dickeya dianthicola, D. zeae etc.), Erwinia spp. (e.g. Erwinia amylovora, E. rhapontici etc.), Pantoea spp., Pectobacterium spp. etc.) Gram-negative bacteria of the phylum Proteobacteria.
Taphrina spp.(例えば、Taphrina deformans、T. pruni等)、Pneumocystis spp.、Geotrichum spp.、Candida spp.(例えば、Candida albicans、C. sorbosa等)、Pichia spp.(例えば、Pichia kluyveri等)、Capnodium spp.、Fumago spp.、Hypocapnodium spp.、Cercospora spp.(例えば、Cercospora apii、C. asparagi、C. beticola、C. capsici、C. carotae、C. kaki、C. kikuchii、C. zonata等)、Cercosporidium spp.、Cladosporium spp.(例えば、Cladosporium colocasiae、C. cucumerinum、C. variabile等)、Davidiella spp.、Didymosporium spp.、Heterosporium spp.(例えば、Heterosporium allii等)、Mycosphaerella spp.(例えば、Mycosphaerella arachidis、M. berkeleyi、M. cerasella、M. fijiensis、M. fragariae、M. graminicola、M. nawae、M. pinodes、M. pomi、M. zingiberis等)、Mycovellosiella spp.(例えば、Mycovellosiella fulva、M. nattrassii等)、Paracercospora spp.(例えば、Paracercospora egenula等)、Phaeoisariopsis spp.、Phaeoramularia spp.、Pseudocercospora spp.(例えば、Pseudocercospora abelmoschi、P. fuligena、P. vitis等)、Pseudocercosporella spp.(例えば、Pseudocercosporella capsellae等)、Ramichloridium spp.、Ramularia spp.、Septogloeum spp.、Septoria spp.(例えば、Septoria albopunctata、S. apiicola、S. chrysanthemella、S. helianthi、S. obesa等)、Sphaerulina spp.、Aureobasidium spp.、Kabatiella spp.、Plowrightia spp.、Stigmina spp.、Elsinoe spp.(例えば、Elsinoe ampelina、E. araliae、E. fawcettii等)、Sphaceloma spp.(例えば、Sphaceloma caricae等)、Ascochyta spp.(例えば、Ascochyta pisi等)、Corynespora spp.(例えば、Corynespora cassiicola等)、Leptosphaeria spp.(例えば、Leptosphaeria coniothyrium、L. maculans等)、Saccharicola spp.、Phaeosphaeria spp. (例えば、Phaeosphaeria nodorum等)、Ophiosphaerella spp.、Setophoma spp.、Helminthosporium spp.、Alternaria spp.(例えば、Alternaria alternata、A. brassicae、A. brassicicola、A. citri、A. dauci、A. helianthi、A. japonica、A. kikuchiana、A. mali、A. panax、A. porri、A. radicina、A. solani等)、Bipolaris spp.(例えば、Bipolaris sorghicola等)、Cochliobolus spp.(例えば、Cochliobolus heterostrophus、C. lunatus、C. miyabeanus等)、Curvularia spp.(例えば、Curvularia geniculata、C. verruculosa等)、Drechslera spp.、Pleospora spp.(例えば、Pleospora herbarum等)、Pyrenophora spp.(例えば、Pyrenophora graminea、P. teres等)、Setosphaeria spp.(例えば、Setosphaeria turcica等)、Stemphylium spp.(例えば、Stemphylium botryosum、S. lycopersici、S. solani、S. vesicarium等)、Fusicladium spp.、Venturia spp.(例えば、Venturia carpophila、V. Inaequalis、V. nashicola、V. pirina等)、Didymella spp.(例えば、Didymella bryoniae、D. fabae等)、Hendersonia spp.、Phoma spp.(例えば、Phoma erratica var. mikan、P. exigua var. exigua、P. wasabiae等)、Pyrenochaeta spp.(例えば、Pyrenochaeta lycopersici等)、Stagonospora spp.(例えば、Stagonospora sacchari等)、Botryosphaeria spp.(例えば、Botryosphaeria berengeriana f. sp. piricola、B. dothidea等)、Dothiorella spp.、Fusicoccum spp.、Guignardia spp.、Lasiodiplodia spp.(例えば、Lasiodiplodia theobromae等)、Macrophoma spp.、Macrophomina spp.、Neofusicoccum spp.、Phyllosticta spp.(例えば、Phyllosticta zingiberis等)、Schizothyrium spp.(例えば、Schizothyrium pomi等)、Acrospermum spp.、Leptosphaerulina spp.、Aspergillus spp.、Penicillium spp.(例えば、Penicillium digitatum、P. italicum、P. sclerotigenum等)、Microsporum spp.、Trichophyton spp.(例えば、Trichophyton mentagrophytes、T. rubrum等)、Histoplasma spp.、Blumeria spp.(例えば、Blumeria graminis f. sp. hordei、B. g. f. sp. tritici等)、Erysiphe spp.(例えば、Erysiphe betae、E. cichoracearum、E. c. var. cichoracearum、E. heraclei、E. pisi等)、Golovinomyces spp.(例えば、Golovinomyces cichoracearum var. latisporus等)、Leveillula spp.(例えば、Leveillula taurica等)、Microsphaera spp.、Oidium spp.(例えば、Oidium neolycopersici等)、Phyllactinia spp.(例えば、Phyllactinia kakicola、P. mali、P. moricola等)、Podosphaera spp.(例えば、Podosphaera fusca、P. leucotricha、P. pannosa、P. tridactyla var. tridactyla、P. xanthii等)、Sphaerotheca spp.(例えば、Sphaerotheca aphanis var. aphanis、S. fuliginea等)、Uncinula spp.(例えば、Uncinula necator、U. n. var. necator等)、Uncinuliella spp.(例えば、Uncinuliella simulans var. simulans、U. s. var. tandae等)、Blumeriella spp.(例えば、Blumeriella jaapii等)、Cylindrosporium spp.、Diplocarpon spp.(例えば、Diplocarpon mali、D. mespili、D. rosae等)、Gloeosporium spp.(例えば、Gloeosporium minus等)、Marssonina spp.、Tapesia spp.(例えば、Tapesia acuformis、T. yallundae等)、Lachnum spp.、Scleromitrula spp.、Botryotinia spp.(例えば、Botryotinia fuckeliana等)、Botrytis spp.(例えば、Botrytis allii、B. byssoidea、B. cinerea、B. elliptica、B. fabae、B. squamosa等)、Ciborinia spp.、Grovesinia spp.、Monilia mumecola、Monilinia spp.(例えば、Monilinia fructicola、M. fructigena、M. laxa、M. mali、M. vaccinii-corymbosi等)、Sclerotinia spp.(例えば、Sclerotinia borealis、S. homoeocarpa、S. minor、S. sclerotiorum等)、Valdensia spp.(例えば、Valdensia heterodoxa等)、Claviceps spp.(例えば、Claviceps sorghi、C. sorghicola等)、Epichloe spp.、Ephelis japonica、Villosiclava virens、Hypomyces spp.(例えば、Hypomyces solani f. sp. mori、H. s. f. sp. pisi等)、Trichoderma spp.(例えば、Trichoderma viride等)、Calonectria spp.(例えば、Calonectria ilicicola等)、Candelospora spp.、Cylindrocarpon spp.、Cylindrocladium spp.、Fusarium spp.(例えば、Fusarium arthrosporioides、F. crookwellense、F. culmorum、F. cuneirostrum、F. oxysporum、F. o. f. sp. adzukicola、F. o. f. sp. allii、F. o. f. sp. asparagi、F. o. f. sp. batatas、F. o. f. sp. cepae、F. o. f. sp. colocasiae、F. o. f. sp. conglutinans、F. o. f. sp. cubense、F. o. f. sp. cucumerinum、F. o. f. sp. fabae、F. o. f. sp. fragariae、F. o. f. sp. lactucae、F. o. f. sp. lagenariae、F. o. f. sp. lycopersici、F. o. f. sp. melongenae、F. o. f. sp. melonis、F. o. f. sp. nelumbinicola、F. o. f. sp. niveum、F. o. f. sp. radicis-lycopersici、F. o. f. sp. raphani、F. o. f. sp. spinaciae、F. sporotrichioides、F. solani、F. s. f. sp. cucurbitae、F. s. f. sp. eumartii、F. s. f. sp. glycines、F. s. f. sp. pisi、F. s. f. sp. Radicicola、F. virguliforme等)、Gibberella spp.(例えば、Gibberella avenacea、G. baccata、G. fujikuroi、G. zeae等)、Haematonectria spp.、Nectria spp.、Ophionectria spp.、Caldariomyces spp.、Myrothecium spp.、Trichothecium spp.、Verticillium spp.(例えば、Verticillium albo-atrum、V. dahliae、V. longisporum等)、Ceratocystis spp.(例えば、Ceratocystis ficicola, C. fimbriata等)、Thielaviopsis spp.(例えば、Thielaviopsis basicola等)、Adisciso spp.、Monochaetia spp.、Pestalotia spp.(例えば、Pestalotia eriobotrifolia等)、Pestalotiopsis spp.(例えば、Pestalotiopsis funerea、P. longiseta、P. neglecta、P. theae等)、Physalospora spp.、Nemania spp.、Nodulisporium spp.、Rosellinia spp.(例えば、Rosellinia necatrix等)、Monographella spp.(例えば、Monographella nivalis等)、Ophiostoma spp.、Cryphonectria spp.(例えば、Cryphonectria parasitica等)、Diaporthe spp.(例えば、Diaporthe citri、D. kyushuensis、D. nomurai、D. tanakae等)、Diaporthopsis spp.、Phomopsis spp.(例えば、Phomopsis asparagi、P. fukushii、P. obscurans、P. vexans等)、Cryptosporella spp.、Discula spp.(例えば、Discula theae-sinensis等)、Gnomonia spp.、Coniella spp.、Coryneum spp.、Greeneria spp.、Melanconis spp.、Cytospora spp.、Leucostoma spp.、Valsa spp.(例えば、Valsa ceratosperma等)、Tubakia spp.、Monosporascus spp.、Clasterosporium spp.、Gaeumannomyces spp.(例えば、Gaeumannomyces graminis等)、Magnaporthe spp.(例えば、Magnaporthe grisea等)、Pyricularia spp.(例えば、Pyricularia zingiberis等)、Monilochaetes infuscans、Colletotrichum spp.(例えば、Colletotrichum acutatum、C. capsici、C. cereale、C. destructivum、C. fragariae、C. lindemuthianum、C. nigrum、C. orbiculare、C. spinaciae等)、Glomerella spp.(例えば、Glomerella cingulata等)、Khuskia oryzae、Phyllachora spp.(例えば、Phyllachora pomigena等)、Ellisembia spp.、Briosia spp.、Cephalosporium spp.(例えば、Cephalosporium gramineum等)、Epicoccum spp.、Gloeocercospora sorghi、Mycocentrospora spp.、Peltaster spp.(例えば、Peltaster fructicola等)、Phaeocytostroma spp.、Phialophora spp.(例えば、Phialophora gregata等)、Pseudophloeosporella dioscoreae、Pseudoseptoria spp.、Rhynchosporium spp.(例えば、Rhynchosporium secalis等)、Sarocladium spp.、Coleophoma spp.、Helicoceras oryzae等の子嚢菌門(Ascomycota)の菌類。Septobasidium spp.(例えば、Septobasidium bogoriense、S. tanakae等)、Helicobasidium spp.(例えば、Helicobasidium longisporum等)、Coleosporium spp.(例えば、Coleosporium plectranthi等)、Cronartium spp.、Phakopsora spp.(例えば、Phakopsora artemisiae、P. nishidana、P. pachyrhizi等)、Physopella spp.(例えば、Physopella ampelopsidis等)、Kuehneola spp.(例えば、Kuehneola japonica等)、Phragmidium spp.(例えば、Phragmidium fusiforme、P. mucronatum、P. rosae-multiflorae等)、Gymnosporangium spp.(例えば、Gymnosporangium asiaticum、G. yamadae等)、Puccinia spp.(例えば、Puccinia allii、P. brachypodii var. poae-nemoralis、P. coronata、P. c. var. coronata、P. cynodontis、P. graminis、P. g. subsp. graminicola、P. hordei、P. horiana、P. kuehnii、P. melanocephala、P. recondita、P. striiformis var. striiformis、P. tanaceti var. tanaceti、P. tokyensis、P. zoysiae等)、Uromyces spp.(例えば、Uromyces phaseoli var. azukicola、U. p. var. phaseoli、Uromyces viciae-fabae var. viciae-fabae等)、Naohidemyces vaccinii、Nyssopsora spp.、Leucotelium spp.、Tranzschelia spp.(例えば、Tranzschelia discolor等)、Aecidium spp.、Blastospora spp.(例えば、Blastospora smilacis等)、Uredo spp.、Sphacelotheca spp.、Urocystis spp.、Sporisorium spp.(例えば、Sporisorium scitamineum等)、Ustilago spp.(例えば、Ustilago maydis、U. nuda等)、
Entyloma spp.、Exobasidium spp.(例えば、Exobasidium reticulatum、E. vexans等)、Microstroma spp.、Tilletia spp.(例えば、Tilletia caries、T. controversa、T. laevis等)、Itersonilia spp.(例えば、Itersonilia perplexans等)、Cryptococcus spp.、Bovista spp.(例えば、Bovista dermoxantha等)、Lycoperdon spp.(例えば、Lycoperdon curtisii、L. perlatum等)、Conocybe spp.(例えば、Conocybe apala等)、Marasmius spp.(例えば、Marasmius oreades 等)、Armillaria spp.、Helotium spp.、Lepista spp.(例えば、Lepista subnuda等)、Sclerotium spp.(例えば、Sclerotium cepivorum等)、Typhula spp.(例えば、Typhula incarnata、T. ishikariensis var. ishikariensis等)、Athelia spp.(例えば、Athelia rolfsii等)、Ceratobasidium spp.(例えば、Ceratobasidium cornigerum等)、Ceratorhiza spp.、Rhizoctonia spp.(例えば、Rhizoctonia solani等)、Thanatephorus spp.(例えば、Thanatephorus cucumeris等)、Laetisaria spp.、Waitea spp.、Fomitiporia spp.、Ganoderma spp.、Chondrostereum purpureum、Phanerochaete spp.等の担子菌門(Basidiomycota)の菌類。Olpidium spp.等のツボカビ門(Chitridiomycota)の菌類。Physoderma spp.等のコウマクノウキン門(Blastocladiomycota)の菌類。Choanephora spp.、Choanephoroidea cucurbitae、Mucor spp.(例えば、Mucor fragilis等)、Rhizopus spp.(例えば、Rhizopus arrhizus、R. chinensis、R. oryzae、R. stolonifer var. stolonifer等)等のケカビ亜門(Mucoromycotina)の菌類。Plasmodiophora spp.(例えば、Plasmodiophora brassicae等)、Spongospora subterranea f. sp. Subterranea等のケルコゾア門(Cercozoa)の原生生物。Aphanomyces spp.(例えば、Aphanomyces cochlioides、A. raphani等)、Albugo spp.(例えば、Albugo macrospora、A. wasabiae等)、Bremia spp.(例えば、Bremia lactucae等)、Hyaloperonospora spp.、Peronosclerospora spp.、Peronospora spp.(例えば、Peronospora alliariae-wasabi、P. chrysanthemi-coronarii、P. destructor、P. farinosa f. sp. spinaciae、P. manshurica、P. parasitica、P. sparsa等)、Plasmopara spp.(例えば、Plasmopara halstedii、P. nivea、P. viticola等)、Pseudoperonospora spp.(例えば、Pseudoperonospora cubensis等)、Sclerophthora spp.、Phytophthora spp.(例えば、Phytophthora cactorum、P. capsici、P. citricola、P. citrophthora、P. cryptogea、P. fragariae、P. infestans、P. melonis、P. nicotianae、P. palmivora、P. porri、P. sojae、P. syringae、P. vignae f. sp. adzukicola等)、Pythium spp.(例えば、Pythium afertile、P. aphanidermatum、P. apleroticum、P. aristosporum、P. arrhenomanes、P. buismaniae、P. debaryanum、P. graminicola、P. horinouchiense、P. irregulare、P. iwayamai、P. myriotylum、P. okanoganense、P. paddicum、P. paroecandrum、P. periplocum、P. spinosum、P. sulcatum、P. sylvaticum、P. ultimum var. ultimum、P. vanterpoolii、P. vexans、P. volutum等)等の不等毛植物門(Heterokontophyta)の卵菌類(Oomycetes)。Clavibacter spp.(例えば、Clavibacter michiganensis subsp. michiganensis等)、Curtobacterium spp.、Leifsonia spp.(例えば、Leifsonia xyli subsp. xyli等)、Streptomyces spp.(例えば、Streptomyces ipomoeae等)等の放線菌門(Actinobacteria)のグラム陽性菌類。Clostridium sp.等のフィルミクテス門(Firmicutes)のグラム陽性菌類。Phytoplasma等のテネリクテス門(Tenericutes)のグラム陽性菌類。Rhizobium spp.(例えば、Rhizobium radiobacter等)、Acetobacter spp.、Burkholderia spp.(例えば、Burkholderia andropogonis、B. cepacia、B. gladioli、B. glumae、B. plantarii等)、Acidovorax spp.(例えば、Acidovorax avenae subsp. avenae、A. a. subsp. citrulli、A. konjaci等)、Herbaspirillum spp.、Ralstonia spp.(例えば、Ralstonia solanacearum等)、Xanthomonas spp.(例えば、Xanthomonas albilineans、X. arboricola pv. pruni、X. axonopodis pv. vitians、X. campestris pv. campestris、X. c. pv. cucurbitae、X. c. pv. glycines、X. c. pv. mangiferaeindicae、X. c. pv. nigromaculans、X. c. pv. vesicatoria、X. citri subsp. citri、X. oryzae pv. oryzae等)、Pseudomonas spp.(例えば、Pseudomonas cichorii、P. fluorescens、P. marginalis、P. m. pv. marginalis、P. savastanoi pv. glycinea、P. syringae、P. s. pv. actinidiae、P. s. pv. eriobotryae、P. s. pv. helianthi、P. s. pv. lachrymans、P. s. pv. maculicola、P. s. pv. mori、P. s. pv. morsprunorum、P. s. pv. spinaciae、P. s. pv. syringae、P. s. pv. theae、P. viridiflava等)、Rhizobacter spp.、Brenneria spp.(例えば、Brenneria nigrifluens等)、Dickeya spp.(例えば、Dickeya dianthicola、D. zeae等)、Erwinia spp.(例えば、Erwinia amylovora、E. rhapontici等)、Pantoea spp.、Pectobacterium spp.(例えば、Pectobacterium atrosepticum、P. carotovorum、P. wasabiae等)等のプロテオバクテリア門(Proteobacteria)のグラム陰性菌類。 The term "pathogen" means microorganisms that cause plant diseases, and specifically includes, but is not limited to, the following microorganisms.
(eg, Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (eg, Candida albicans, C. sorbosa, etc.), Pichia spp. (eg, Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. Cercosporidium spp., Cladosporium spp. (e.g. Cladosporium colocasiae, C. cucumerinum, C. variabile etc.), Davidiella spp. , M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis, etc.), Mycovellosiella spp. nattrassii etc.), Paracercospora spp. (e.g. Paracercospora egenula etc.), Phaeoisariopsis spp., Phaeoramularia spp. etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp. , Septoria spp. (e.g. Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g. Elsinoe ampelina, E. araliae, E. fawcettii etc.), Sphaceloma spp. (e.g. Sphaceloma caricae etc.), Ascochyta spp. , Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp. alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc. ), Bipolaris spp. (e.g. Bipolaris sorghicola etc.), Cochliobolus spp. (e.g. Cochliobolus heterostrophus, C. lunatus, C. miyabeanus etc.), Curvularia spp. , Pleospora spp. (e.g. Pleospora herbarum etc.), Pyrenophora spp. nea, P. teres etc.), Setosphaeria spp. (e.g. Setosphaeria turcica etc.), Stemphylium spp. For example, Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina, etc.), Didymella spp. P. exigua var. exigua, P. wasabiae, etc.), Pyrenochaeta spp. (e.g., Pyrenochaeta lycopersici, etc.), Stagonospora spp. dothidea etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. , Schizothyrium spp. (eg, Schizothyrium pomi, etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. (eg, Penicillium digitatum, P. italicum, P. sclerotigenum, etc.), Microsporum spp., Trichophyton spp. (e.g., Trichophyton mentagrophytes, T rubrum etc.), Histoplasma spp., Blumeria spp. cichoracearum, E. heraclei, E. pisi, etc.), Golovinomyces spp. (e.g., Golovinomyces cichoracearum var. latisporus, etc.), Leveillula spp. etc.), Phyllactinia spp. (e.g. Phyllactinia kakicola, P. mali, P. moricola etc.), Podosphaera spp. ), Sphaerotheca spp. (e.g. Sphaerotheca aphanis var. aphanis, S. fuliginea etc.), Uncinula spp. , U. s. var. tandae etc.), Blumeriella spp. (e.g. Blumeriella jaapii etc.), Cylindrosporium spp. , Gloeosporium minus etc.), Marssonina spp., Tapesia spp. (e.g. Tapesia acuformis, T. yallundae etc.), Lachnum spp. ula spp., Botryotinia spp. (e.g. Botryotinia fuckeliana etc.), Botrytis spp. Grovesinia spp., Monilia mumecola, Monilinia spp. minor, S. sclerotiorum etc.), Valdensia spp. (e.g. Valdensia heterodoxa etc.), Claviceps spp. , Hypomyces solani f. sp. mori, H. s. f. sp. pisi, etc.), Trichoderma spp. (e.g., Trichoderma viride, etc.), Calonectria spp. , Fusarium spp. (e.g., Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. o. f. sp. adzukicola, F. o. f. sp. allii, F. o. f. sp. asparagi, F. sp. batatas, F.o.f.sp.cepae, F.o.f.sp.colocasiae, F.o.f.sp.conglutinans, F.o.f.s p. cubense, F. o. f. sp. cucumerinum, F. o. f. sp. fabae, F. o. f. sp. fragariae, F. o. f. sp. lactucae, F. o. f. sp. melonis, F. o. f. sp. nelumbinicola, F. o. f. sp. niveum, F. o. f. sp. radicis-lycopersici, F. o. f. sp. sp. cucurbitae, F. s. f. sp. eumartii, F. s. f. sp. glycines, F. s. f. sp. pisi, F. s. f. sp. Radicicola, F. virguliforme, etc.), Gibberella spp. For example, Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. albo-atrum, V. dahliae, V. longisporum etc.), Ceratocystis spp. (e.g. Ceratocystis ficicola, C. fimbriata etc.), Thielaviopsis spp. (e.g., Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp. (e.g., Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.), Physalospora spp., Nemania spp., Nodulisporium spp., Roselinia spp. (e.g., Roselinia necatrix etc.), Monographella spp. spp. (e.g. Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae etc.), Diaporthopsis spp., Phomopsis spp. spp., Discula spp. (e.g., Discula theae-sinensis etc.), Gnomonia spp., Coniella spp., Coryneum spp., Greeneria spp. Valsa ceratosperma etc.), Tubakia spp., Monosporascus spp., Clusterosporium spp., Gaeumannomyces spp. (e.g. Gaeumannomyces graminis etc.), Magnaporthe spp. Monilochaetes infuscans, Colletotrichum spp. Glomerella cingulata, etc.), Khuskia ory zae, Phyllachora spp. (e.g. Phyllachora pomigena etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. fructicola etc.), Phaeocytostroma spp., Phialophora spp. Fungi of the phylum Ascomycota. Septobasidium spp. (e.g. Septobasidium bogoriense, S. tanakae etc.), Helicobasidium spp. (e.g. Helicobasidium longisporum etc.), Coleosporium spp. P. nishidana, P. pachyrhizi etc.), Physopella spp. (e.g. Physopella ampelopsidis etc.), Kuehneola spp. (e.g. Kuehneola japonica etc.), Phragmidium spp. etc.), Gymnosporangium spp. (e.g. Gymnosporangium asiaticum, G. yamadae etc.), Puccinia spp. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P. tanaceti var. tokyensis, P.zoysiae, etc.), Uromyces spp. (e.g., Uromyces phaseoli var. azukicola, U.p. var. phaseoli, Uromyces viciae-fabae var. , Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (e.g., Sporisorium scitamineum, etc.), Ustilago spp. ),
Entyloma spp., Exobasidium spp. (e.g. Exobasidium reticulatum, E. vexans, etc.), Microstroma spp., Tilletia spp. etc.), Cryptococcus spp., Bovista spp. (e.g., Bovista dermoxantha etc.), Lycoperdon spp. Marasmius oreades etc.), Armillaria spp., Helotium spp., Lepista spp. (e.g. Lepista subnuda etc.), Sclerotium spp. etc.), Athelia spp. (e.g. Athelia rolfsii etc.), Ceratobasidium spp. , Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaete spp. Fungi of the phylum Chitridiomycota, such as Olpidium spp. Fungi of the phylum Blastocladiomycota, such as Physoderma spp. Mucoromycotina such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis), Rhizopus spp. ) fungi. Protists of the phylum Cercozoa, such as Plasmodiophora spp. (eg Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea. Aphanomyces spp. (e.g. Aphanomyces cochlioides, A. raphani etc.), Albugo spp. (e.g. Albugo macrospora, A. wasabiae etc.), Bremia spp. spp. halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (e.g., Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. , Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P. debaryanum, P. graminicola, P. horinouchiense, P. irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, Oomycetes of Heterokontophyta, such as P. ultimum var. ultimum, P. vanterpoolii, P. vexans, P. volutum, etc.). Actinobacteria such as Clavibacter spp. (e.g. Clavibacter michiganensis subsp. michiganensis), Curtobacterium spp., Leifsonia spp. of Gram-positive bacteria. Gram-positive fungi of the phylum Firmicutes, such as Clostridium sp. Gram-positive fungi of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp. (e.g. Rhizobium radiobacter etc.), Acetobacter spp., Burkholderia spp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (e.g., Ralstonia solanacearum, etc.), Xanthomonas spp. vitians, X. campestris pv. campestris, X. c. pv. cucurbitae, X. c. pv. glycines, X. c. pv. vesicatoria, X. citri subsp. citri, X. oryzae pv. oryzae, etc.), Pseudomonas spp. , P. syringae, P. s. pv. actinidiae, P. s. pv. eriobotryae, P. s. pv. helianthi, P. s. pv. mori, P. s. pv. morsprunorum, P. s. pv. spinaciae, P. s. pv. syringae, P. s. pv. theae, P. viridiflava, etc.), Rhizobacter spp., Brenneria spp. , Brenneria nigrifluens, etc.), Dick eya spp. (e.g. Dickeya dianthicola, D. zeae etc.), Erwinia spp. (e.g. Erwinia amylovora, E. rhapontici etc.), Pantoea spp., Pectobacterium spp. etc.) Gram-negative bacteria of the phylum Proteobacteria.
これら病原菌の感染・増殖によって引き起こされる植物病害の具体例としては、以下の植物病害が挙げられるが、これらに限定されるものではない。
モモ縮葉病Leaf curl(Taphrina deformans)、スモモふくろ実病Plum pockets(Taphrina pruni)、アスパラガス褐斑病Leaf spot(Cercospora asparagi)、テンサイ褐斑病Cercospora leaf spot(Cercospora beticola)、ピーマン斑点病Frogeye leaf spot(Cercospora capsici)、カキ角斑落葉病Angular leaf spot(Cercospora kaki)、ダイズ紫斑病Purple stain(Cercospora kikuchii)、ラッカセイ褐斑病Brown Leaf spot(Mycosphaerella arachidis)、オウトウ褐色せん孔病Cylindrosporium leaf spot(Mycosphaerella cerasella, Blumeriella jaapii)、ブラックシガトカ病Black sigatoka(Mycosphaerella fijiensis)、イエローシガトカ病Yellow sigatoka(Mycosphaerell musicola)、コムギ葉枯病Speckled leaf blotch(Mycosphaerella graminicola)、カキ円星落葉病Circular leaf spot(Mycosphaerella nawae)、エンドウ褐紋病Mycosphaerella blight(Mycosphaerella pinodes)、ミョウガ葉枯病Leaf spot(Mycosphaerella zingiberis)、トマト葉かび病Leaf mold(Mycovellosiella fulva)、ナスすすかび病Leaf mold(Mycovellosiella nattrassii)、トマトすすかび病Cercospora leaf mold(Pseudocercospora fuligena)、ブドウ褐斑病Isariopsis leaf spot(Pseudocercospora vitis)、ハクサイ白斑病Leaf spot(Pseudocercosporella capsellae)、キク黒斑病Leaf spot(Septoria chrysanthemella)、キク褐斑病Leaf blight(Septoria obesa)、ブドウ黒とう病Anthracnose(Elsinoe ampelina)、タラノキそうか病Spot anthracnose(Elsinoe araliae)、カンキツそうか病Scab(Elsinoe fawcettii)、エンドウ褐斑病Leaf spot(Ascochyta pisi)、キュウリ褐斑病Corynespora leaf spot(Corynespora cassiicola)、バラ枝枯病Stem canker(Leptosphaeria coniothyrium)、コムギふ枯病Glume blotch(Leptosphaeria nodorum)、バラ黒斑病Leaf spot(Alternaria alternata)、キャベツ黒斑病Alternaria leaf spot(Alternaria brassicae)、ニンジン黒葉枯病Leaf blight(Alternaria dauci)、ナシ黒斑病Black spot(Alternaria kikuchiana)、リンゴ斑点落葉病Alternaria blotch(Alternaria mali)、ネギ黒斑病Alternaria leaf spot(Alternaria porri)、ソルガム紫斑点病Target spot(Bipolaris sorghicola)、トウモロコシごま葉枯病Southern leaf blight(Cochliobolus heterostrophus)、イネごま葉枯病Brown spot(Cochliobolus miyabeanus)、ニンニク葉枯病Tip blight(Pleospora herbarum)、オオムギ斑葉病Stripe(Pyrenophora graminea)、オオムギ網斑病Net blotch(Pyrenophora teres)、ソルガムすす紋病Leaf blight(Setosphaeria turcica)、トウモロコシすす紋病Northern leaf blight(Setosphaeria turcica)、アスパラガス斑点病Leaf spot(Stemphylium botryosum)、バラ科サクラ亜科の黒星病Scab(Venturia carpophila)、リンゴ黒星病Scab(Venturia Inaequalis)、ナシ黒星病Scab(Venturia nashicola)、ウリ科のつる枯病Gummy stem blight(Didymella bryoniae)、ゴボウ黒斑病Leaf spot(Phoma exigua var. exigua)、ワサビ墨入病Streak(Phoma wasabiae)、バラ科ナシ亜科の輪紋病Ring rot(Botryosphaeria berengeriana f. sp. piricola)、キウイフルーツ果実軟腐病Soft rot(Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.)、カンキツ緑かび病Common green mold(Penicillium digitatum)、カンキツ青かび病Blue mold(Penicillium italicum)、各種作物に発生するうどんこ病Powdery mildew、オオムギうどんこ病(Blumeria graminis f. sp. hordei)、コムギうどんこ病(Blumeria graminis f. sp. tritici)、キュウリうどんこ病(Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii)、ナスうどんこ病(Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea)、ニンジン、パセリのうどんこ病(Erysiphe heraclei)、エンドウうどんこ病(Erysiphe pisi)、トマトうどんこ病(Leveillula taurica, Oidium neolycopersici, Oidium sp.)、ピーマンうどんこ病(Leveillula taurica)、カボチャうどんこ病(Oidium sp., Podosphaera xanthii)、ニガウリうどんこ病(Oidium sp.)、カキうどんこ病(Phyllactinia kakicola)、ゴボウうどんこ病(Podosphaera fusca)、リンゴうどんこ病(Podosphaera leucotricha)、バラうどんこ病(Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae)、ズッキーニ、マクワウリのうどんこ病(Podosphaera xanthii)、イチゴうどんこ病(Sphaerotheca aphanis var. aphanis)、スイカ、メロンのうどんこ病(Sphaerotheca fuliginea)、ブドウうどんこ病(Uncinula necator, U. n. var. necator)、リンゴ褐斑病Blotch(Diplocarpon mali)、バラ黒星病Black spot(Diplocarpon rosae)、タマネギ灰色腐敗病Gray mold neck rot(Botrytis allii)、灰色かび病Gray mold、Botrytis blight(Botrytis cinerea)、ニラ白斑葉枯病Leaf blight(Botrytis cinerea, B. byssoidea, B. squamosa)、ソラマメ赤色斑点病Chocolate spot(Botrytis cinerea, B. elliptica, B. fabae)、バラ科の灰星病Brown rot(Monilinia fructicola, M. fructigena, M. laxa)、リンゴモニリア病Blossom blight(Monilinia mali)、シバダラースポット病Dollar spot(Sclerotinia homoeocarpa)、菌核病Cottony rot、Sclerotinia rot、Stem rot(Sclerotinia sclerotiorum)、稲こうじ病False smut(Villosiclava virens)、ダイズ黒根腐病Root necrosis(Calonectria ilicicola)、コムギ赤かび病Fusarium blight(Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae, Monographella nivalis)、オオムギ赤かび病Fusarium blight(Fusarium culmorum, Gibberella avenacea, G. zeae)、コンニャク乾腐病Dry rot(Fusarium oxysporum, F. solani f. sp. radicicola)、ヤマノイモ褐色腐敗病Brown rot(Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola)、アズキ萎凋病Fusarium wilt(Fusarium oxysporum f. sp. adzukicola)、ラッキョウ乾腐病Fusarium basal rot(Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola)、サツマイモつる割病Stem rot(Fusarium oxysporum f. sp. batatas, F. solani)、サトイモ乾腐病Dry rot(Fusarium oxysporum f. sp. colocasiae)、キャベツ、コマツナの萎黄病Yellows(Fusarium oxysporum f. sp. conglutinans)、バナナパナマ病Panama disease(Fusarium oxysporum f. sp. cubense)、イチゴ萎黄病Fusarium wilt(Fusarium oxysporum f. sp. fragariae)、レタス根腐病Root rot(Fusarium oxysporum f. sp. lactucae)、スイカつる割病Fusarium wilt(Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum)、トマト萎凋病Fusarium wilt(Fusarium oxysporum f. sp. lycopersici)、メロンつる割病Fusarium wilt(Fusarium oxysporum f. sp. melonis)、ダイコン萎黄病Yellows(Fusarium oxysporum f. sp. raphani)、ホウレンソウ萎凋病Fusarium wilt(Fusarium oxysporum f. sp. spinaciae)、ダイズ急性枯死症Soybean Sudden Death Syndrome(Fusarium solani f. sp. Glycines, Fusarium virguliforme)、イネばか苗病“Bakanae”disease(Gibberella fujikuroi)、ダイコンバーティシリウム黒点病Verticillium black spot(Verticillium albo-atrum, V. dahliae)、トマト、ナス、フキの半身萎凋病Verticillium wilt(Verticillium dahliae)、イチジク株枯病Ceratocystis canker(Ceratocystis ficicola)、サツマイモ黒斑病Black rot(Ceratocystis fimbriata)、チャ輪斑病Gray blight(Pestalotiopsis longiseta, P. theae)、クリ胴枯病Endothia canker(Cryphonectria parasitica)、カンキツ黒点病Melanose(Diaporthe citri)、アスパラガス茎枯病Stem blight(Phomopsis asparagi)、ナシ胴枯病Phomopsis canker(Phomopsis fukushii)、ナス褐紋病Brown spot(Phomopsis vexans)、チャ炭疽病Anthracnose(Discula theae-sinensis)、リンゴ腐らん病Valsa canker(Valsa ceratosperma)、イネいもち病Blast(Magnaporthe grisea)、イチゴ炭疽病Crown rot(Colletotrichum acutatum, C. fragariae, Glomerella cingulata)、リンゴ炭疽病Bitter rot(Colletotrichum acutatum, Glomerella cingulata)、オウトウ炭疽病Anthracnose(Colletotrichum acutatum, Glomerella cingulata)、スモモ炭疽病Anthracnose(Colletotrichum acutatum)、ブドウ晩腐病Ripe rot(Colletotrichum acutatum, Glomerella cingulata)、シュンギク炭疽病Anthracnose(Colletotrichum acutatum)、インゲンマメ炭疽病Anthracnose(Colletotrichum lindemuthianum)、ウリ科の炭疽病Anthracnose(Colletotrichum orbiculare)、ヤマノイモ炭疽病Anthracnose(Glomerella cingulata)、クリ炭疽病Anthracnose(Glomerella cingulata)、カキ炭疽病Anthracnose(Glomerella cingulata)、アズキ落葉病Brown stem rot(Phialophora gregata)、ナガイモ葉渋病Leaf spot(Pseudophloeosporella dioscoreae)、オオムギ雲形病Scald(Rhynchosporium secalis)、コムギ赤さび病Brown rust(Puccinia recondita)、コムギ黄さび病Stripe rust(Puccinia striiformis )、各種作物に発生するさび病Rust、イチジクさび病(Phakopsora nishidana)、ダイズさび病(Phakopsora pachyrhizi)、バラさび病(Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae)、ナシ赤星病(Gymnosporangium asiaticum)、リンゴ赤星病(Gymnosporangium yamadae)、ネギ科のさび病(Puccinia allii)、キク白さび病(Puccinia horiana)、キク黒さび病(Puccinia tanaceti var. tanaceti)、ソラマメさび病(Uromyces viciae-fabae var. viciae-fabae)、サトウキビ黒穂病(Sporisorium scitamineum)、トウモロコシ黒穂病(Ustilago maydis)、オオムギ裸黒穂病Loose smut(Ustilago nuda)、チャ網もち病Net blister blight(Exobasidium reticulatum)、チャもち病Blister blight(Exobasidium vexans)、白絹病Stem rot、Southern blight(Athelia rolfsii)、キク立枯病Root and stem rot(Ceratobasidium cornigerum, Rhizoctonia solani)、ショウガ紋枯病(Rhizoctonia solani)、キャベツ苗立枯病Damping-off(Rhizoctonia solani)、ミツバ立枯病Damping-off(Rhizoctonia solani)、レタスすそ枯病Bottom rot(Rhizoctonia solani)、シバ葉腐病Brown patch、Large patch(Rhizoctonia solani)、イネ紋枯病Sheath blight(Thanatephorus cucumeris)、テンサイ根腐病Root rot(Thanatephorus cucumeris)、テンサイ葉腐病Leaf blight(Thanatephorus cucumeris)、イチジク黒かび病Rhizopus rot(Rhizopus stolonifer var. stolonifer)、アブラナ科野菜根こぶ病Clubroot(Plasmodiophora brassicae)、テンサイ黒根病Aphanomyces root rot(Aphanomyces cochlioides)、アブラナ科の白さび病White rust(Albugo macrospora)、各種の作物に発生するべと病Downy mildew、レタスべと病(Bremia lactucae)、シュンギクべと病(Peronospora chrysanthemi-coronarii)、タマネギ、ネギのべと病(Peronospora destructor)、ホウレンソウべと病(Peronospora farinosa f. sp. spinaciae)、ダイズべと病(Peronospora manshurica)、アブラナ科のべと病(Peronospora parasitica)、バラべと病(Peronospora sparsa)、ヒマワリべと病(Plasmopara halstedii)、ミツバべと病(Plasmopara nivea)、ブドウべと病(Plasmopara viticola)、ウリ科のべと病(Pseudoperonospora cubensis)、タラノキ立枯疫病Phytophthora root rot(Phytophthora cactorum)、スイカ褐色腐敗病Brown rot(Phytophthora capsici)、カボチャ疫病Phytophthora rot(Phytophthora capsici)、ピーマン疫病Phytophthora blight(Phytophthora capsici)、スイカ疫病Phytophthora rot(Phytophthora cryptogea)、トマト、ジャガイモの疫病Late blight(Phytophthora infestans)、イチジク疫病Wh
ite powdery rot(Phytophthora palmivora)、ネギ科の白色疫病Leaf blight(Phytophthora porri)、ダイズ茎疫病Phytophthora root and stem rot(Phytophthora sojae)、アズキ茎疫病Phytophthora stem rot(Phytophthora vignae f. sp. adzukicola)、ホウレンソウ立枯病Damping-off(Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum)、コンニャク根腐病Root rot(Pythium aristosporum)、トウモロコシ根腐病Browning root rot(Pythium arrhenomanes, P. graminicola)、キャベツ苗立枯病Damping-off(Pythium buismaniae, P. myriotylum)、ミョウガ根茎腐敗病Root rot(Pythium myriotylum)、ショウガ根茎腐敗病Root rot(Pythium myriotylum, P. ultimum var. ultimum)、ニンジンしみ腐病Brown blotted root rot(Pythium sulcatum)、トマトかいよう病Bacterial canker(Clavibacter michiganensis subsp. michiganensis)、ジャガイモそうか病Scab(Streptomyces spp.)、バラ根頭がんしゅ病Crown gall(Rhizobium radiobacter)、ソルガム条斑細菌病Bacterial stripe(Burkholderia andropogonis)、タマネギ腐敗病Soft rot(Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici)、イネもみ枯細菌病Bacterial grain rot(Burkholderia gladioli, B. glumae)、スイカ果実汚斑細菌病Bacterial fruit blotch(Acidovorax avenae subsp. citrulli)、コンニャク葉枯病Bacterial leaf blight(Acidovorax konjaci)、青枯病Bacterial wilt(Ralstonia solanacearum)、モモせん孔細菌病Bacterial shot hole(Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens)、スモモ黒斑病Bacterial leaf spot(Xanthomonas arboricola pv. pruni)、レタス斑点細菌病Bacterial spot(Xanthomonas axonopodis pv. vitians)、アブラナ科の黒腐病Black rot(Xanthomonas campestris pv. campestris)、ダイズ葉焼病Bacterial pustule(Xanthomonas campestris pv. glycines)、ゴボウ黒斑細菌病Bacterial spot(Xanthomonas campestris pv. nigromaculans)、ピーマン斑点細菌病Bacterial spot(Xanthomonas campestris pv. vesicatoria)、カンキツかいよう病Citrus canker(Xanthomonas citri subsp. citri)、ニンニク春腐病(Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.)、レタス腐敗病Bacterial rot(Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava)、キウイフルーツ花腐細菌病Bacterial blossom blight(Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava)、キウイフルーツかいよう病Bacterial canker(Pseudomonas syringae pv. actinidiae)、ビワがんしゅ病Canker(Pseudomonas syringae pv. eriobotryae)、ウリ科の斑点細菌病Bacterial spot(Pseudomonas syringae pv. lachrymans)、アブラナ科の黒斑細菌病Bacterial black spot(Pseudomonas syringae pv. maculicola)、ウメかいよう病Bacterial canker(Pseudomonas syringae pv. morsprunorum, Erwinia sp.)、チャ赤焼病Bacterial shoot blight(Pseudomonas syringae pv. theae)、ネギ軟腐病Bacterial soft rot(Dickeya sp., Pectobacterium carotovorum)、バラ科ナシ亜科の火傷病Fire blight(Erwinia amylovora)、コンニャク腐敗病Soft rot(Pectobacterium carotovorum)、軟腐病Bacterial soft rot(Pectobacterium carotovorum)が挙げられる。 Specific examples of plant diseases caused by infection/proliferation of these pathogenic fungi include, but are not limited to, the following plant diseases.
Peach leaf curl (Taphrina deformans), Plum pockets (Taphrina pruni), Asparagus leaf spot (Cercospora asparagi), Sugar beet Cercospora leaf spot (Cercospora beticola), Green pepper spot Frogeye leaf spot (Cercospora capsici), Angular leaf spot (Cercospora kaki), Soybean purple stain (Cercospora kikuchii), Brown Leaf spot (Mycosphaerella arachidis), Cherry Cylindrosporium leaf spot ( Mycosphaerella cerasella, Blumeriella jaapii), Black sigatoka (Mycosphaerella fijiensis), Yellow sigatoka (Mycosphaerell musicola), Speckled leaf blotch (Mycosphaerella graminicola), Circular leaf spot Mycosphaerella nawae), pea brown spot Mycosphaerella blight (Mycosphaerella pinodes), myoga Leaf spot (Mycosphaerella zingiberis), tomato leaf mold Leaf mold (Mycovellosiella fulva), eggplant soot Leaf mold (Mycovellosiella nattrassii), tomato soot Cercospora leaf mold (Pseudocercospora fuligena), Isariopsis leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spot (Pseudocercosporella capsellae), Chrysanthemum leaf spot (Septoria chrysanthemella), Chrysanthemum leaf blight (Septoria obesa), Grape black spot Anthracnose (Elsinoe ampelina), Aralia spot anthracnose (Elsinoe araliae), Citrus scab (Elsinoe fawcettii), Pea leaf spot (Ascochyta) pisi), Corynespora leaf spot (Corynespora cassiicola), Stem canker (Leptosphaeria coniothyrium), Glume blotch (Leptosphaeria nodorum), Leaf spot (Alternaria alternata), Cabbage black Alternaria leaf spot (Alternaria brassicae), Leaf blight (Alternaria dauci), Black spot (Alternaria kikuchiana), Alternaria blotch (Alternaria mali), Alternaria leaf spot (Alternaria mali) spot (Alternaria porri), Sorghum purple spot (Bipolaris sorghicola), Maize leaf blight Southern leaf blight (Cochliobolus heterostrophus), Rice leaf blight Brown spot (Cochliobolus miyabeanus), Garlic leaf blight Tip blight (Pleospora) herbarum), Stripe (Pyrenophora graminea), Net blotch (Pyrenophora teres), Sorghum Leaf blight (Setosphaeria turcica), Corn Northern leaf blight (Setosphaeria turcica), Asparagus spot Disease Leaf spot (Stemphylium botryosum), scab Scab (Venturia carpophila) of the Rosaceae Prunus subfamily, Apple scab Scab (Venturia Inaequalis), Pear scab Scab (Venturia nashicola), Cucurbitaceae Gummy stem blight (Didymella bryoniae), Burdock black spot (Phoma exigua var. exigua), Wasabi ink stain Streak (Phoma wasabiae), Ring rot (Botryosphaeria berengeriana f. sp. piricola), Kiwi fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Citrus green mold Common green mold (Penicillium digitatum), Citrus blue mold (Penicillium italicum), Powdery mildew on various crops, Barley powdery mildew (Blumeria graminis f. sp. hordei), Wheat powdery mildew (Blumeria graminis) f. sp. tritici), cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (Oidium sp.), oyster powdery mildew (Phyllactinia kakicola), burdock powdery mildew (Podosphaera fusca), apple powdery mildew (Podosphaera leucotricha) , rose powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), zucchini, milk melon powdery mildew (Podosphaera xanthii), strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), watermelon, Melon powdery mildew (Sphaerotheca fuliginea), Grape powdery mildew (Uncinula necator, U. n. var. necator), Apple Blotch (Diplocarpon mali), Rose spot Black spot (Diplocarpon rosae), Onion gray rot Gray mold neck rot (Botrytis allii), gray mold Gray mold, Botrytis blight (Botrytis cinerea), Chinese chive leaf blight Leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), Faba bean red spot Chocolate spot ( Botrytis cinerea, B. elliptica, B. fabae), Brown rot (Monilinia fructicola, M. fructigena, M. laxa), Blossom blight (Monilinia mali), Dollar spot ( Sclerotinia homoeocarpa), Sclerotinia Cottony rot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), False smut (Villosiclava virens), Soybean black root rot Root necrosis (Calonectria ilicicola), Wheat Fusarium blight (Fusarium crookwellense Fusarium blight (Fusarium culmorum, Gibbe rella avenacea, G. zeae), Dry rot of konjac (Fusarium oxysporum, F. solani f. sp. radicicola), Brown rot of yam (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola), adzuki bean wilt Fusarium wilt (Fusarium oxysporum f. sp. adzukicola), shallot dry rot Fusarium basal rot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), sweet potato wilt Stem rot (Fusarium oxysporum f. sp. batatas, F. solani), Taro dry rot (Fusarium oxysporum f. sp. colocasiae), Cabbage, Komatsuna Yellows (Fusarium oxysporum f. sp. conglutinans), Banana Panama disease (Fusarium oxysporum f. sp. cubense), Strawberry wilt Fusarium wilt (Fusarium oxysporum f. sp. fragariae), Lettuce root rot (Fusarium oxysporum f. sp. lactucae), Watermelon wilt Fusarium wilt (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), tomato wilt Fusarium wilt (Fusarium oxysporum f. sp. lycopersici), melon wilt Fusarium wilt (Fusarium oxysporum f. sp. melonis), Japanese radish Yellows (Fusarium oxysporum f. sp. raphani), Fusarium wilt (Fusarium oxysporum f. sp. spinaciae), Soybean Sudden Deat h Syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), Bakanae disease in rice (Gibberella fujikuroi), Verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, Verticillium wilt (Verticillium dahliae) of eggplant and butterbur, Ceratocystis canker (Ceratocystis ficicola), Black rot (Ceratocystis fimbriata), Gray blight (Pestalotiopsis longiseta, P. theae) , Endothia canker (Cryphonectria parasitica), Citrus black spot (Diaporthe citri), Stem blight (Phomopsis asparagi), Phomopsis canker (Phomopsis fukushii), Eggplant brown spot (Phomopsis vexans), Tea Anthracnose (Discula theae-sinensis), Apple rot Valsa canker (Valsa ceratosperma), Rice blast Blast (Magnaporthe grisea), Strawberry anthracnose Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata) ), Apple Bitter rot (Colletotrichum acutatum, Glomerella cingulata), Cherry Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Plum Anthracnose (Colletotrichum acutatum), Grape late rot Ripe rot (Colletotrichum acutatum, Glomerella cingulata) ingulata), Chrysanthemum Anthracnose (Colletotrichum acutatum), Kidney Anthracnose Anthracnose (Colletotrichum lindemuthianum), Cucurbitaceae Anthracnose (Colletotrichum orbiculare), Dioscorea Anthracnose (Glomerella cingulata), Chestnut Anthracnose Anthracnose (Glomerella cing), Oyster anthracnose Anthracnose (Glomerella cingulata), adzuki bean defoliation Brown stem rot (Phialophora gregata), Chinese yam Leaf spot (Pseudophloeosporella dioscoreae), Barley cloud disease Scald (Rhynchosporium secalis), Wheat leaf rust Brown rust (Puccinia recondita), Wheat yellow rust (Puccinia striiformis), rust on various crops, fig rust (Phakopsora nishidana), soybean rust (Phakopsora pachyrhizi), rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), Gymnosporangium asiaticum, Gymnosporangium yamadae, Puccinia allii, Puccinia horiana, Puccinia tanaceti var tanaceti), broad bean rust (Uromyces viciae-fabae var. Net blister blight (Exobasidium reticulatum), Tea blister Bl ister blight (Exobasidium vexans), white silk disease Stem rot, Southern blight (Athelia rolfsii), chrysanthemum wilt Root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger sheath blight (Rhizoctonia solani), cabbage seedling blight Damping-off (Rhizoctonia solani), Damping-off (Rhizoctonia solani), Bottom rot (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Sheath blight (Thanatephorus cucumeris), beet root rot (Thanatephorus cucumeris), beet leaf rot Leaf blight (Thanatephorus cucumeris), fig black mold Rhizopus rot (Rhizopus stolonifer var. stolonifer), cruciferous vegetable clubroot Clubroot ( Plasmodiophora brassicae), Aphanomyces root rot (Aphanomyces cochlioides), White rust (Albugo macrospora), Downy mildew, Bremia lactucae, Chrysanthemum spp. Downy mildew (Peronospora chrysanthemi-coronarii), onion downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. sp. spinaciae), soybean downy mildew (Peronospora manshurica), cruciferous downy mildew Peronospora parasitica, Peronospora sparsa, Plasmopara halstedii, Plasmopara nivea, grape downy mildew ( Plasmopara viticola), Pseudoperonospora cubensis, Pseudoperonospora cubensis, Phytophthora root rot (Phytophthora cactorum), Brown rot of watermelon (Phytophthora capsici), Phytophthora rot (Phytophthora capsici), Pepper Phytophthora blight (Phytophthora capsici), watermelon late blight Phytophthora rot (Phytophthora cryptogea), tomato, potato late blight (Phytophthora infestans), fig late blight Wh
ite powdery rot (Phytophthora palmivora), allium leaf blight (Phytophthora porri), Phytophthora root and stem rot (Phytophthora sojae), Phytophthora stem rot (Phytophthora vignae f. sp. adzukicola), spinach Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), Konjac root rot (Pythium aristosporum), Corn root rot Browning root rot (Pythium arrhenomanes, P. graminicola), damping-off of cabbage (Pythium buismaniae, P. myriotylum), Root rot of Japanese ginger (Pythium myriotylum), Root rot of ginger (Pythium myriotylum, P. ultimum var. ultimum), carrot Brown blotted root rot (Pythium sulcatum), Bacterial canker (Clavibacter michiganensis subsp. michiganensis), Potato scab (Streptomyces spp.), Crown gall (Rhizobium radiobacter), Bacterial stripe of sorghum (Burkholderia andropogonis), Soft rot of onion (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), Bacterial grain rot of rice (Burkholderia gladioli, B. glumae), Watermelon fruit Bacterial Frui t blotch (Acidovorax avenae subsp. citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens), Plum black spot Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Lettuce black spot Bacterial spot (Xanthomonas axonopodis pv. vitians), Cruciferous black rot (Xanthomonas campestris pv. campestris) , Bacterial pustule (Xanthomonas campestris pv. glycines), Bacterial spot (Xanthomonas campestris pv. nigromaculans), Bacterial spot (Xanthomonas campestris pv. vesicatoria), Bacterial spot (Xanthomonas campestris pv. vesicatoria), Citrus canker ( Xanthomonas citri subsp. citri), garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), lettuce rot Bacterial rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), kiwifruit Bacterial blossom blight (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava), Bacterial canker (Pseudomonas sy actinidiae), Canker (Pseudomonas syringae pv. eriobotryae), Bacterial spot (Pseudomonas syringae pv. lachrymans), Bacterial black spot (Pseudomonas syringae pv) maculicola), Bacterial canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), Bacterial shoot blight (Pseudomonas syringae pv. theae), Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum) , Fire blight (Erwinia amylovora) of the family Pear family, konnyaku rot Soft rot (Pectobacterium carotovorum), soft rot Bacterial soft rot (Pectobacterium carotovorum).
モモ縮葉病Leaf curl(Taphrina deformans)、スモモふくろ実病Plum pockets(Taphrina pruni)、アスパラガス褐斑病Leaf spot(Cercospora asparagi)、テンサイ褐斑病Cercospora leaf spot(Cercospora beticola)、ピーマン斑点病Frogeye leaf spot(Cercospora capsici)、カキ角斑落葉病Angular leaf spot(Cercospora kaki)、ダイズ紫斑病Purple stain(Cercospora kikuchii)、ラッカセイ褐斑病Brown Leaf spot(Mycosphaerella arachidis)、オウトウ褐色せん孔病Cylindrosporium leaf spot(Mycosphaerella cerasella, Blumeriella jaapii)、ブラックシガトカ病Black sigatoka(Mycosphaerella fijiensis)、イエローシガトカ病Yellow sigatoka(Mycosphaerell musicola)、コムギ葉枯病Speckled leaf blotch(Mycosphaerella graminicola)、カキ円星落葉病Circular leaf spot(Mycosphaerella nawae)、エンドウ褐紋病Mycosphaerella blight(Mycosphaerella pinodes)、ミョウガ葉枯病Leaf spot(Mycosphaerella zingiberis)、トマト葉かび病Leaf mold(Mycovellosiella fulva)、ナスすすかび病Leaf mold(Mycovellosiella nattrassii)、トマトすすかび病Cercospora leaf mold(Pseudocercospora fuligena)、ブドウ褐斑病Isariopsis leaf spot(Pseudocercospora vitis)、ハクサイ白斑病Leaf spot(Pseudocercosporella capsellae)、キク黒斑病Leaf spot(Septoria chrysanthemella)、キク褐斑病Leaf blight(Septoria obesa)、ブドウ黒とう病Anthracnose(Elsinoe ampelina)、タラノキそうか病Spot anthracnose(Elsinoe araliae)、カンキツそうか病Scab(Elsinoe fawcettii)、エンドウ褐斑病Leaf spot(Ascochyta pisi)、キュウリ褐斑病Corynespora leaf spot(Corynespora cassiicola)、バラ枝枯病Stem canker(Leptosphaeria coniothyrium)、コムギふ枯病Glume blotch(Leptosphaeria nodorum)、バラ黒斑病Leaf spot(Alternaria alternata)、キャベツ黒斑病Alternaria leaf spot(Alternaria brassicae)、ニンジン黒葉枯病Leaf blight(Alternaria dauci)、ナシ黒斑病Black spot(Alternaria kikuchiana)、リンゴ斑点落葉病Alternaria blotch(Alternaria mali)、ネギ黒斑病Alternaria leaf spot(Alternaria porri)、ソルガム紫斑点病Target spot(Bipolaris sorghicola)、トウモロコシごま葉枯病Southern leaf blight(Cochliobolus heterostrophus)、イネごま葉枯病Brown spot(Cochliobolus miyabeanus)、ニンニク葉枯病Tip blight(Pleospora herbarum)、オオムギ斑葉病Stripe(Pyrenophora graminea)、オオムギ網斑病Net blotch(Pyrenophora teres)、ソルガムすす紋病Leaf blight(Setosphaeria turcica)、トウモロコシすす紋病Northern leaf blight(Setosphaeria turcica)、アスパラガス斑点病Leaf spot(Stemphylium botryosum)、バラ科サクラ亜科の黒星病Scab(Venturia carpophila)、リンゴ黒星病Scab(Venturia Inaequalis)、ナシ黒星病Scab(Venturia nashicola)、ウリ科のつる枯病Gummy stem blight(Didymella bryoniae)、ゴボウ黒斑病Leaf spot(Phoma exigua var. exigua)、ワサビ墨入病Streak(Phoma wasabiae)、バラ科ナシ亜科の輪紋病Ring rot(Botryosphaeria berengeriana f. sp. piricola)、キウイフルーツ果実軟腐病Soft rot(Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.)、カンキツ緑かび病Common green mold(Penicillium digitatum)、カンキツ青かび病Blue mold(Penicillium italicum)、各種作物に発生するうどんこ病Powdery mildew、オオムギうどんこ病(Blumeria graminis f. sp. hordei)、コムギうどんこ病(Blumeria graminis f. sp. tritici)、キュウリうどんこ病(Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii)、ナスうどんこ病(Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea)、ニンジン、パセリのうどんこ病(Erysiphe heraclei)、エンドウうどんこ病(Erysiphe pisi)、トマトうどんこ病(Leveillula taurica, Oidium neolycopersici, Oidium sp.)、ピーマンうどんこ病(Leveillula taurica)、カボチャうどんこ病(Oidium sp., Podosphaera xanthii)、ニガウリうどんこ病(Oidium sp.)、カキうどんこ病(Phyllactinia kakicola)、ゴボウうどんこ病(Podosphaera fusca)、リンゴうどんこ病(Podosphaera leucotricha)、バラうどんこ病(Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae)、ズッキーニ、マクワウリのうどんこ病(Podosphaera xanthii)、イチゴうどんこ病(Sphaerotheca aphanis var. aphanis)、スイカ、メロンのうどんこ病(Sphaerotheca fuliginea)、ブドウうどんこ病(Uncinula necator, U. n. var. necator)、リンゴ褐斑病Blotch(Diplocarpon mali)、バラ黒星病Black spot(Diplocarpon rosae)、タマネギ灰色腐敗病Gray mold neck rot(Botrytis allii)、灰色かび病Gray mold、Botrytis blight(Botrytis cinerea)、ニラ白斑葉枯病Leaf blight(Botrytis cinerea, B. byssoidea, B. squamosa)、ソラマメ赤色斑点病Chocolate spot(Botrytis cinerea, B. elliptica, B. fabae)、バラ科の灰星病Brown rot(Monilinia fructicola, M. fructigena, M. laxa)、リンゴモニリア病Blossom blight(Monilinia mali)、シバダラースポット病Dollar spot(Sclerotinia homoeocarpa)、菌核病Cottony rot、Sclerotinia rot、Stem rot(Sclerotinia sclerotiorum)、稲こうじ病False smut(Villosiclava virens)、ダイズ黒根腐病Root necrosis(Calonectria ilicicola)、コムギ赤かび病Fusarium blight(Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae, Monographella nivalis)、オオムギ赤かび病Fusarium blight(Fusarium culmorum, Gibberella avenacea, G. zeae)、コンニャク乾腐病Dry rot(Fusarium oxysporum, F. solani f. sp. radicicola)、ヤマノイモ褐色腐敗病Brown rot(Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola)、アズキ萎凋病Fusarium wilt(Fusarium oxysporum f. sp. adzukicola)、ラッキョウ乾腐病Fusarium basal rot(Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola)、サツマイモつる割病Stem rot(Fusarium oxysporum f. sp. batatas, F. solani)、サトイモ乾腐病Dry rot(Fusarium oxysporum f. sp. colocasiae)、キャベツ、コマツナの萎黄病Yellows(Fusarium oxysporum f. sp. conglutinans)、バナナパナマ病Panama disease(Fusarium oxysporum f. sp. cubense)、イチゴ萎黄病Fusarium wilt(Fusarium oxysporum f. sp. fragariae)、レタス根腐病Root rot(Fusarium oxysporum f. sp. lactucae)、スイカつる割病Fusarium wilt(Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum)、トマト萎凋病Fusarium wilt(Fusarium oxysporum f. sp. lycopersici)、メロンつる割病Fusarium wilt(Fusarium oxysporum f. sp. melonis)、ダイコン萎黄病Yellows(Fusarium oxysporum f. sp. raphani)、ホウレンソウ萎凋病Fusarium wilt(Fusarium oxysporum f. sp. spinaciae)、ダイズ急性枯死症Soybean Sudden Death Syndrome(Fusarium solani f. sp. Glycines, Fusarium virguliforme)、イネばか苗病“Bakanae”disease(Gibberella fujikuroi)、ダイコンバーティシリウム黒点病Verticillium black spot(Verticillium albo-atrum, V. dahliae)、トマト、ナス、フキの半身萎凋病Verticillium wilt(Verticillium dahliae)、イチジク株枯病Ceratocystis canker(Ceratocystis ficicola)、サツマイモ黒斑病Black rot(Ceratocystis fimbriata)、チャ輪斑病Gray blight(Pestalotiopsis longiseta, P. theae)、クリ胴枯病Endothia canker(Cryphonectria parasitica)、カンキツ黒点病Melanose(Diaporthe citri)、アスパラガス茎枯病Stem blight(Phomopsis asparagi)、ナシ胴枯病Phomopsis canker(Phomopsis fukushii)、ナス褐紋病Brown spot(Phomopsis vexans)、チャ炭疽病Anthracnose(Discula theae-sinensis)、リンゴ腐らん病Valsa canker(Valsa ceratosperma)、イネいもち病Blast(Magnaporthe grisea)、イチゴ炭疽病Crown rot(Colletotrichum acutatum, C. fragariae, Glomerella cingulata)、リンゴ炭疽病Bitter rot(Colletotrichum acutatum, Glomerella cingulata)、オウトウ炭疽病Anthracnose(Colletotrichum acutatum, Glomerella cingulata)、スモモ炭疽病Anthracnose(Colletotrichum acutatum)、ブドウ晩腐病Ripe rot(Colletotrichum acutatum, Glomerella cingulata)、シュンギク炭疽病Anthracnose(Colletotrichum acutatum)、インゲンマメ炭疽病Anthracnose(Colletotrichum lindemuthianum)、ウリ科の炭疽病Anthracnose(Colletotrichum orbiculare)、ヤマノイモ炭疽病Anthracnose(Glomerella cingulata)、クリ炭疽病Anthracnose(Glomerella cingulata)、カキ炭疽病Anthracnose(Glomerella cingulata)、アズキ落葉病Brown stem rot(Phialophora gregata)、ナガイモ葉渋病Leaf spot(Pseudophloeosporella dioscoreae)、オオムギ雲形病Scald(Rhynchosporium secalis)、コムギ赤さび病Brown rust(Puccinia recondita)、コムギ黄さび病Stripe rust(Puccinia striiformis )、各種作物に発生するさび病Rust、イチジクさび病(Phakopsora nishidana)、ダイズさび病(Phakopsora pachyrhizi)、バラさび病(Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae)、ナシ赤星病(Gymnosporangium asiaticum)、リンゴ赤星病(Gymnosporangium yamadae)、ネギ科のさび病(Puccinia allii)、キク白さび病(Puccinia horiana)、キク黒さび病(Puccinia tanaceti var. tanaceti)、ソラマメさび病(Uromyces viciae-fabae var. viciae-fabae)、サトウキビ黒穂病(Sporisorium scitamineum)、トウモロコシ黒穂病(Ustilago maydis)、オオムギ裸黒穂病Loose smut(Ustilago nuda)、チャ網もち病Net blister blight(Exobasidium reticulatum)、チャもち病Blister blight(Exobasidium vexans)、白絹病Stem rot、Southern blight(Athelia rolfsii)、キク立枯病Root and stem rot(Ceratobasidium cornigerum, Rhizoctonia solani)、ショウガ紋枯病(Rhizoctonia solani)、キャベツ苗立枯病Damping-off(Rhizoctonia solani)、ミツバ立枯病Damping-off(Rhizoctonia solani)、レタスすそ枯病Bottom rot(Rhizoctonia solani)、シバ葉腐病Brown patch、Large patch(Rhizoctonia solani)、イネ紋枯病Sheath blight(Thanatephorus cucumeris)、テンサイ根腐病Root rot(Thanatephorus cucumeris)、テンサイ葉腐病Leaf blight(Thanatephorus cucumeris)、イチジク黒かび病Rhizopus rot(Rhizopus stolonifer var. stolonifer)、アブラナ科野菜根こぶ病Clubroot(Plasmodiophora brassicae)、テンサイ黒根病Aphanomyces root rot(Aphanomyces cochlioides)、アブラナ科の白さび病White rust(Albugo macrospora)、各種の作物に発生するべと病Downy mildew、レタスべと病(Bremia lactucae)、シュンギクべと病(Peronospora chrysanthemi-coronarii)、タマネギ、ネギのべと病(Peronospora destructor)、ホウレンソウべと病(Peronospora farinosa f. sp. spinaciae)、ダイズべと病(Peronospora manshurica)、アブラナ科のべと病(Peronospora parasitica)、バラべと病(Peronospora sparsa)、ヒマワリべと病(Plasmopara halstedii)、ミツバべと病(Plasmopara nivea)、ブドウべと病(Plasmopara viticola)、ウリ科のべと病(Pseudoperonospora cubensis)、タラノキ立枯疫病Phytophthora root rot(Phytophthora cactorum)、スイカ褐色腐敗病Brown rot(Phytophthora capsici)、カボチャ疫病Phytophthora rot(Phytophthora capsici)、ピーマン疫病Phytophthora blight(Phytophthora capsici)、スイカ疫病Phytophthora rot(Phytophthora cryptogea)、トマト、ジャガイモの疫病Late blight(Phytophthora infestans)、イチジク疫病Wh
ite powdery rot(Phytophthora palmivora)、ネギ科の白色疫病Leaf blight(Phytophthora porri)、ダイズ茎疫病Phytophthora root and stem rot(Phytophthora sojae)、アズキ茎疫病Phytophthora stem rot(Phytophthora vignae f. sp. adzukicola)、ホウレンソウ立枯病Damping-off(Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum)、コンニャク根腐病Root rot(Pythium aristosporum)、トウモロコシ根腐病Browning root rot(Pythium arrhenomanes, P. graminicola)、キャベツ苗立枯病Damping-off(Pythium buismaniae, P. myriotylum)、ミョウガ根茎腐敗病Root rot(Pythium myriotylum)、ショウガ根茎腐敗病Root rot(Pythium myriotylum, P. ultimum var. ultimum)、ニンジンしみ腐病Brown blotted root rot(Pythium sulcatum)、トマトかいよう病Bacterial canker(Clavibacter michiganensis subsp. michiganensis)、ジャガイモそうか病Scab(Streptomyces spp.)、バラ根頭がんしゅ病Crown gall(Rhizobium radiobacter)、ソルガム条斑細菌病Bacterial stripe(Burkholderia andropogonis)、タマネギ腐敗病Soft rot(Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici)、イネもみ枯細菌病Bacterial grain rot(Burkholderia gladioli, B. glumae)、スイカ果実汚斑細菌病Bacterial fruit blotch(Acidovorax avenae subsp. citrulli)、コンニャク葉枯病Bacterial leaf blight(Acidovorax konjaci)、青枯病Bacterial wilt(Ralstonia solanacearum)、モモせん孔細菌病Bacterial shot hole(Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens)、スモモ黒斑病Bacterial leaf spot(Xanthomonas arboricola pv. pruni)、レタス斑点細菌病Bacterial spot(Xanthomonas axonopodis pv. vitians)、アブラナ科の黒腐病Black rot(Xanthomonas campestris pv. campestris)、ダイズ葉焼病Bacterial pustule(Xanthomonas campestris pv. glycines)、ゴボウ黒斑細菌病Bacterial spot(Xanthomonas campestris pv. nigromaculans)、ピーマン斑点細菌病Bacterial spot(Xanthomonas campestris pv. vesicatoria)、カンキツかいよう病Citrus canker(Xanthomonas citri subsp. citri)、ニンニク春腐病(Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.)、レタス腐敗病Bacterial rot(Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava)、キウイフルーツ花腐細菌病Bacterial blossom blight(Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava)、キウイフルーツかいよう病Bacterial canker(Pseudomonas syringae pv. actinidiae)、ビワがんしゅ病Canker(Pseudomonas syringae pv. eriobotryae)、ウリ科の斑点細菌病Bacterial spot(Pseudomonas syringae pv. lachrymans)、アブラナ科の黒斑細菌病Bacterial black spot(Pseudomonas syringae pv. maculicola)、ウメかいよう病Bacterial canker(Pseudomonas syringae pv. morsprunorum, Erwinia sp.)、チャ赤焼病Bacterial shoot blight(Pseudomonas syringae pv. theae)、ネギ軟腐病Bacterial soft rot(Dickeya sp., Pectobacterium carotovorum)、バラ科ナシ亜科の火傷病Fire blight(Erwinia amylovora)、コンニャク腐敗病Soft rot(Pectobacterium carotovorum)、軟腐病Bacterial soft rot(Pectobacterium carotovorum)が挙げられる。 Specific examples of plant diseases caused by infection/proliferation of these pathogenic fungi include, but are not limited to, the following plant diseases.
Peach leaf curl (Taphrina deformans), Plum pockets (Taphrina pruni), Asparagus leaf spot (Cercospora asparagi), Sugar beet Cercospora leaf spot (Cercospora beticola), Green pepper spot Frogeye leaf spot (Cercospora capsici), Angular leaf spot (Cercospora kaki), Soybean purple stain (Cercospora kikuchii), Brown Leaf spot (Mycosphaerella arachidis), Cherry Cylindrosporium leaf spot ( Mycosphaerella cerasella, Blumeriella jaapii), Black sigatoka (Mycosphaerella fijiensis), Yellow sigatoka (Mycosphaerell musicola), Speckled leaf blotch (Mycosphaerella graminicola), Circular leaf spot Mycosphaerella nawae), pea brown spot Mycosphaerella blight (Mycosphaerella pinodes), myoga Leaf spot (Mycosphaerella zingiberis), tomato leaf mold Leaf mold (Mycovellosiella fulva), eggplant soot Leaf mold (Mycovellosiella nattrassii), tomato soot Cercospora leaf mold (Pseudocercospora fuligena), Isariopsis leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spot (Pseudocercosporella capsellae), Chrysanthemum leaf spot (Septoria chrysanthemella), Chrysanthemum leaf blight (Septoria obesa), Grape black spot Anthracnose (Elsinoe ampelina), Aralia spot anthracnose (Elsinoe araliae), Citrus scab (Elsinoe fawcettii), Pea leaf spot (Ascochyta) pisi), Corynespora leaf spot (Corynespora cassiicola), Stem canker (Leptosphaeria coniothyrium), Glume blotch (Leptosphaeria nodorum), Leaf spot (Alternaria alternata), Cabbage black Alternaria leaf spot (Alternaria brassicae), Leaf blight (Alternaria dauci), Black spot (Alternaria kikuchiana), Alternaria blotch (Alternaria mali), Alternaria leaf spot (Alternaria mali) spot (Alternaria porri), Sorghum purple spot (Bipolaris sorghicola), Maize leaf blight Southern leaf blight (Cochliobolus heterostrophus), Rice leaf blight Brown spot (Cochliobolus miyabeanus), Garlic leaf blight Tip blight (Pleospora) herbarum), Stripe (Pyrenophora graminea), Net blotch (Pyrenophora teres), Sorghum Leaf blight (Setosphaeria turcica), Corn Northern leaf blight (Setosphaeria turcica), Asparagus spot Disease Leaf spot (Stemphylium botryosum), scab Scab (Venturia carpophila) of the Rosaceae Prunus subfamily, Apple scab Scab (Venturia Inaequalis), Pear scab Scab (Venturia nashicola), Cucurbitaceae Gummy stem blight (Didymella bryoniae), Burdock black spot (Phoma exigua var. exigua), Wasabi ink stain Streak (Phoma wasabiae), Ring rot (Botryosphaeria berengeriana f. sp. piricola), Kiwi fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Citrus green mold Common green mold (Penicillium digitatum), Citrus blue mold (Penicillium italicum), Powdery mildew on various crops, Barley powdery mildew (Blumeria graminis f. sp. hordei), Wheat powdery mildew (Blumeria graminis) f. sp. tritici), cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (Oidium sp.), oyster powdery mildew (Phyllactinia kakicola), burdock powdery mildew (Podosphaera fusca), apple powdery mildew (Podosphaera leucotricha) , rose powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), zucchini, milk melon powdery mildew (Podosphaera xanthii), strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), watermelon, Melon powdery mildew (Sphaerotheca fuliginea), Grape powdery mildew (Uncinula necator, U. n. var. necator), Apple Blotch (Diplocarpon mali), Rose spot Black spot (Diplocarpon rosae), Onion gray rot Gray mold neck rot (Botrytis allii), gray mold Gray mold, Botrytis blight (Botrytis cinerea), Chinese chive leaf blight Leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), Faba bean red spot Chocolate spot ( Botrytis cinerea, B. elliptica, B. fabae), Brown rot (Monilinia fructicola, M. fructigena, M. laxa), Blossom blight (Monilinia mali), Dollar spot ( Sclerotinia homoeocarpa), Sclerotinia Cottony rot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), False smut (Villosiclava virens), Soybean black root rot Root necrosis (Calonectria ilicicola), Wheat Fusarium blight (Fusarium crookwellense Fusarium blight (Fusarium culmorum, Gibbe rella avenacea, G. zeae), Dry rot of konjac (Fusarium oxysporum, F. solani f. sp. radicicola), Brown rot of yam (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola), adzuki bean wilt Fusarium wilt (Fusarium oxysporum f. sp. adzukicola), shallot dry rot Fusarium basal rot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), sweet potato wilt Stem rot (Fusarium oxysporum f. sp. batatas, F. solani), Taro dry rot (Fusarium oxysporum f. sp. colocasiae), Cabbage, Komatsuna Yellows (Fusarium oxysporum f. sp. conglutinans), Banana Panama disease (Fusarium oxysporum f. sp. cubense), Strawberry wilt Fusarium wilt (Fusarium oxysporum f. sp. fragariae), Lettuce root rot (Fusarium oxysporum f. sp. lactucae), Watermelon wilt Fusarium wilt (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), tomato wilt Fusarium wilt (Fusarium oxysporum f. sp. lycopersici), melon wilt Fusarium wilt (Fusarium oxysporum f. sp. melonis), Japanese radish Yellows (Fusarium oxysporum f. sp. raphani), Fusarium wilt (Fusarium oxysporum f. sp. spinaciae), Soybean Sudden Deat h Syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), Bakanae disease in rice (Gibberella fujikuroi), Verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, Verticillium wilt (Verticillium dahliae) of eggplant and butterbur, Ceratocystis canker (Ceratocystis ficicola), Black rot (Ceratocystis fimbriata), Gray blight (Pestalotiopsis longiseta, P. theae) , Endothia canker (Cryphonectria parasitica), Citrus black spot (Diaporthe citri), Stem blight (Phomopsis asparagi), Phomopsis canker (Phomopsis fukushii), Eggplant brown spot (Phomopsis vexans), Tea Anthracnose (Discula theae-sinensis), Apple rot Valsa canker (Valsa ceratosperma), Rice blast Blast (Magnaporthe grisea), Strawberry anthracnose Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata) ), Apple Bitter rot (Colletotrichum acutatum, Glomerella cingulata), Cherry Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Plum Anthracnose (Colletotrichum acutatum), Grape late rot Ripe rot (Colletotrichum acutatum, Glomerella cingulata) ingulata), Chrysanthemum Anthracnose (Colletotrichum acutatum), Kidney Anthracnose Anthracnose (Colletotrichum lindemuthianum), Cucurbitaceae Anthracnose (Colletotrichum orbiculare), Dioscorea Anthracnose (Glomerella cingulata), Chestnut Anthracnose Anthracnose (Glomerella cing), Oyster anthracnose Anthracnose (Glomerella cingulata), adzuki bean defoliation Brown stem rot (Phialophora gregata), Chinese yam Leaf spot (Pseudophloeosporella dioscoreae), Barley cloud disease Scald (Rhynchosporium secalis), Wheat leaf rust Brown rust (Puccinia recondita), Wheat yellow rust (Puccinia striiformis), rust on various crops, fig rust (Phakopsora nishidana), soybean rust (Phakopsora pachyrhizi), rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), Gymnosporangium asiaticum, Gymnosporangium yamadae, Puccinia allii, Puccinia horiana, Puccinia tanaceti var tanaceti), broad bean rust (Uromyces viciae-fabae var. Net blister blight (Exobasidium reticulatum), Tea blister Bl ister blight (Exobasidium vexans), white silk disease Stem rot, Southern blight (Athelia rolfsii), chrysanthemum wilt Root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger sheath blight (Rhizoctonia solani), cabbage seedling blight Damping-off (Rhizoctonia solani), Damping-off (Rhizoctonia solani), Bottom rot (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Sheath blight (Thanatephorus cucumeris), beet root rot (Thanatephorus cucumeris), beet leaf rot Leaf blight (Thanatephorus cucumeris), fig black mold Rhizopus rot (Rhizopus stolonifer var. stolonifer), cruciferous vegetable clubroot Clubroot ( Plasmodiophora brassicae), Aphanomyces root rot (Aphanomyces cochlioides), White rust (Albugo macrospora), Downy mildew, Bremia lactucae, Chrysanthemum spp. Downy mildew (Peronospora chrysanthemi-coronarii), onion downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. sp. spinaciae), soybean downy mildew (Peronospora manshurica), cruciferous downy mildew Peronospora parasitica, Peronospora sparsa, Plasmopara halstedii, Plasmopara nivea, grape downy mildew ( Plasmopara viticola), Pseudoperonospora cubensis, Pseudoperonospora cubensis, Phytophthora root rot (Phytophthora cactorum), Brown rot of watermelon (Phytophthora capsici), Phytophthora rot (Phytophthora capsici), Pepper Phytophthora blight (Phytophthora capsici), watermelon late blight Phytophthora rot (Phytophthora cryptogea), tomato, potato late blight (Phytophthora infestans), fig late blight Wh
ite powdery rot (Phytophthora palmivora), allium leaf blight (Phytophthora porri), Phytophthora root and stem rot (Phytophthora sojae), Phytophthora stem rot (Phytophthora vignae f. sp. adzukicola), spinach Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), Konjac root rot (Pythium aristosporum), Corn root rot Browning root rot (Pythium arrhenomanes, P. graminicola), damping-off of cabbage (Pythium buismaniae, P. myriotylum), Root rot of Japanese ginger (Pythium myriotylum), Root rot of ginger (Pythium myriotylum, P. ultimum var. ultimum), carrot Brown blotted root rot (Pythium sulcatum), Bacterial canker (Clavibacter michiganensis subsp. michiganensis), Potato scab (Streptomyces spp.), Crown gall (Rhizobium radiobacter), Bacterial stripe of sorghum (Burkholderia andropogonis), Soft rot of onion (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), Bacterial grain rot of rice (Burkholderia gladioli, B. glumae), Watermelon fruit Bacterial Frui t blotch (Acidovorax avenae subsp. citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens), Plum black spot Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Lettuce black spot Bacterial spot (Xanthomonas axonopodis pv. vitians), Cruciferous black rot (Xanthomonas campestris pv. campestris) , Bacterial pustule (Xanthomonas campestris pv. glycines), Bacterial spot (Xanthomonas campestris pv. nigromaculans), Bacterial spot (Xanthomonas campestris pv. vesicatoria), Bacterial spot (Xanthomonas campestris pv. vesicatoria), Citrus canker ( Xanthomonas citri subsp. citri), garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), lettuce rot Bacterial rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), kiwifruit Bacterial blossom blight (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava), Bacterial canker (Pseudomonas sy actinidiae), Canker (Pseudomonas syringae pv. eriobotryae), Bacterial spot (Pseudomonas syringae pv. lachrymans), Bacterial black spot (Pseudomonas syringae pv) maculicola), Bacterial canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), Bacterial shoot blight (Pseudomonas syringae pv. theae), Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum) , Fire blight (Erwinia amylovora) of the family Pear family, konnyaku rot Soft rot (Pectobacterium carotovorum), soft rot Bacterial soft rot (Pectobacterium carotovorum).
農園芸作物の病害に対する防除剤の開発が進み、多種多様な薬剤が今日まで実用に供されてきた。しかしながら、こうした薬剤の長年にわたる使用により、近年、病原菌が薬剤抵抗性を獲得し、従来用いられてきた既存の殺菌剤による防除が困難となる場面が増えてきている。また、既存の薬剤の一部のものは毒性が高く、あるものは環境中に長期間残留することにより、生態系を攪乱するという問題も顕在化しつつある。このような状況下、本発明化合物は、多くの病原菌に対して優れた防除活性を有し、かつ、対象となる作物に対する高い安全性を有する。また、本発明化合物は、既存の殺菌剤に対して抵抗性を獲得した病原菌に対しても、十分な防除効果を発揮し得る。さらに、本発明化合物は、対象となる作物に薬害を生じることがなく、ホ乳類、魚類及び益虫に対してほとんど悪影響を及ぼさず、低残留性で環境に対する負荷も軽い。
Development of control agents against diseases of agricultural and horticultural crops has progressed, and a wide variety of agents have been put into practical use to date. However, in recent years, due to the long-term use of such agents, pathogenic bacteria have acquired drug resistance, and there are increasing cases where it is difficult to control them with the existing fungicides that have been conventionally used. In addition, some of the existing drugs are highly toxic, and some of them remain in the environment for a long period of time, thereby disturbing the ecosystem. Under such circumstances, the compounds of the present invention have excellent control activity against many pathogens and have high safety against target crops. In addition, the compound of the present invention can exert a sufficient control effect against pathogenic bacteria that have acquired resistance to existing fungicides. Furthermore, the compounds of the present invention do not cause phytotoxicity to target crops, have almost no adverse effects on mammals, fish and beneficial insects, are low in residue, and have a low environmental impact.
本発明化合物は、農園芸用殺菌剤としての使用以外に、抗真菌剤又は内部寄生虫防除剤として利用される医療用抗菌剤及び動物用抗菌剤、木材、紙・パルプ、接着剤・塗料、繊維及び皮革などの防菌・防かび剤、並びに製造工場の冷却水路などの工業用殺菌剤としても使用できる。
In addition to being used as an agricultural and horticultural fungicide, the compound of the present invention can be It can also be used as an antibacterial and antifungal agent for textiles and leather, and as an industrial disinfectant for cooling water channels in manufacturing plants.
医療用抗菌剤又は動物用抗菌剤として対象となる病原菌としては、例えば、Trichophyton rubrum及びTrichophyton mentagrophytesなどの白癬菌類、Candida albicansなどのカンジダ菌類、Aspergillus fumigatusなどのアスペルギルス菌類、Cryptococcus neoformasなどのクリプトコックス菌類、大腸菌(Escherichia coli)、緑膿菌(Pseudomonas aeruginosa)及びインフルエンザ菌(Haemophilus influenzae)などのグラム陰性細菌類、黄色ブドウ球菌(Staphylococcus aureus)及び化膿レンサ球菌(Streptococcus pyogenes)などのグラム陽性細菌類等が挙げられるが、これらのみに限定されるものではない。
Examples of pathogenic bacteria that are targeted as antibacterial agents for medical use or antibacterial agents for animals include trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, candida fungi such as Candida albicans, aspergillus fungi such as Aspergillus fumigatus, and cryptococcus fungi such as Cryptococcus neoformas. , Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa and Haemophilus influenzae, Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes, etc. include, but are not limited to, these.
防菌・防かび剤として対象となる菌株としては、例えば、Tyromyces palustris及びCoriolus versicolorなどの木材腐朽菌類、Aspergillus niger、Aspergillus terreus、Eurotium tonophilum、Penicillium citrinum、Penicillium funiculosum、Rhizopus oryzae、Cladosporium cladosporioides、Aureobasidium pullulans、Gliocladium virens、Chaetomium globosum、Fusarium moniliforme及びMyrothecium verrucariaなどの資材の劣化微生物類等が挙げられるが、これらのみに限定されるものではない。
Strains targeted as antibacterial and antifungal agents include, for example, wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor, Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans , Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria.
工業用殺菌剤として対象となる菌株としては、例えば、Sphaerotilis natans及びZoogloea ramigeraなどのスライム菌類等が挙げられるが、これらのみに限定されるものではない。
Strains targeted as industrial fungicides include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera.
本発明化合物は、農園芸用殺菌剤としての使用以外に、家畜、家禽又は愛玩動物等の内部寄生虫防除剤としても使用できる。
In addition to being used as an agricultural and horticultural fungicide, the compound of the present invention can also be used as an internal parasite control agent for livestock, poultry, pets, and the like.
対象となる内部寄生虫としては、以下の具体例が挙げられるが、これらのみに限定されるものではない。
ヘモンクス属(Haemonchus)、トリコストロンギルス属(Trichostrongylus)、オステルターギヤ属(Ostertagia)、ネマトディルス属(Nematodirus)、クーペリア属(Cooperia)、アスカリス属(Ascaris)、ブノストムーム属(Bunostomum)、エスファゴストムーム属(Oesophagostomum)、チャベルチア属(Chabertia)、トリキュリス属(Trichuris)、ストロンギルス属(Storongylus)、トリコネマ属(Trichonema)、ディクチオカウルス属(Dictyocaulus)、キャピラリア属(Capillaria)、ヘテラキス属(Heterakis)、トキソカラ属(Toxocara)、アスカリディア属(Ascaridia)、オキシウリス属(Oxyuris)、アンキロストーマ属(Ancylostoma)、ウンシナリア属(Uncinaria)、トキサスカリス属(Toxascaris)、パラスカリス属(Parascaris)などの線虫類;
ブツヘレリア属(Wuchereria)、ブルージア属(Brugia)、オンコセルカ属(Onchoceca)、ディロフィラリア属(Dirofilaria)、ロア糸状虫属(Loa)などのフィラリア科(Filariidae)線虫類;
ドラクンクルス属(Deacunculus)などの蛇状線虫科(Dracunculidae)線虫類;
犬条虫(Dipylidium caninum)、猫条虫(Taenia taeniaeformis)、有鉤条虫(Taenia solium)、無鉤条虫(Taenia saginata)、縮小条虫(Hymenolepis diminuta)、ベネデン条虫(Moniezia benedeni)、広節裂頭条虫(Diphyllobothrium latum)、マンソン裂頭条虫(Diphyllobothrium erinacei)、単包条虫(Echinococcus granulosus)、多包条虫(Echinococcus multilocularis)などの条虫類;
肝蛭(Fasciola hepatica,F.gigantica)、ウエステルマン肺吸虫(Paragonimus westermanii)、肥大吸虫(Fasciolopsic bruski)、膵吸虫(Eurytrema pancreaticum,E.coelomaticum)、肝吸虫(Clonorchis sinensis)、日本住血吸虫(Schistosoma japonicum)、ビルハルツ住血吸虫(Schistosoma haematobium)、マンソン住血吸虫(Schistosoma mansoni)などの吸虫類;
エイメリア・テネラ(Eimeria tenella)、エイメリア・アセルブリナ(Eimeria acervulina)、エイメリア・ブルネッチ(Eimeria brunetti)、エイメリア・マクシマ(Eimeria maxima)、エイメリア・ネカトリクス(Eimeria necatrix)、エイメリア・ボビス(Eimeria bovis)、エイメリア・オビノイダリス(Eimeria ovinoidalis)のようなエイメリア類(Eimeria spp.);
クルーズトリパノソーマ(Trypanosomsa cruzi)、リーシュマニア類(Leishmania spp.)、マラリア原虫(Plasmodium spp.)、バベシア類(Babesis spp.)、トリコモナス類(Trichomonadidae spp.)、ヒストモナス類(Histomanas spp.)、ジアルディア類(Giardia spp.)、トキソプラズマ類(Toxoplasma spp.)、赤痢アメーバ(Entamoeba histolytica)、タイレリア類(Theileria spp.)等。 Specific examples of target endoparasites include, but are not limited to, the following.
Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Esphagostomum Genus Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis ), Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris and other nematodes ;
Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa;
Dracunculidae nematodes such as Dracunculus;
Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, tapeworms such as Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus, Echinococcus multilocularis;
Fasciola hepatica, F.gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E.coelomaticum, Clonorchis sinensis, Schistosoma japonicum), Schistosoma haematobium, Schistosoma mansoni, and other flukes;
Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria bovis Eimeria spp., such as Eimeria ovinoidalis;
Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomonas spp., Giardia (Giardia spp.), Toxoplasma spp., Entamoeba histolytica, Theileria spp. and the like.
ヘモンクス属(Haemonchus)、トリコストロンギルス属(Trichostrongylus)、オステルターギヤ属(Ostertagia)、ネマトディルス属(Nematodirus)、クーペリア属(Cooperia)、アスカリス属(Ascaris)、ブノストムーム属(Bunostomum)、エスファゴストムーム属(Oesophagostomum)、チャベルチア属(Chabertia)、トリキュリス属(Trichuris)、ストロンギルス属(Storongylus)、トリコネマ属(Trichonema)、ディクチオカウルス属(Dictyocaulus)、キャピラリア属(Capillaria)、ヘテラキス属(Heterakis)、トキソカラ属(Toxocara)、アスカリディア属(Ascaridia)、オキシウリス属(Oxyuris)、アンキロストーマ属(Ancylostoma)、ウンシナリア属(Uncinaria)、トキサスカリス属(Toxascaris)、パラスカリス属(Parascaris)などの線虫類;
ブツヘレリア属(Wuchereria)、ブルージア属(Brugia)、オンコセルカ属(Onchoceca)、ディロフィラリア属(Dirofilaria)、ロア糸状虫属(Loa)などのフィラリア科(Filariidae)線虫類;
ドラクンクルス属(Deacunculus)などの蛇状線虫科(Dracunculidae)線虫類;
犬条虫(Dipylidium caninum)、猫条虫(Taenia taeniaeformis)、有鉤条虫(Taenia solium)、無鉤条虫(Taenia saginata)、縮小条虫(Hymenolepis diminuta)、ベネデン条虫(Moniezia benedeni)、広節裂頭条虫(Diphyllobothrium latum)、マンソン裂頭条虫(Diphyllobothrium erinacei)、単包条虫(Echinococcus granulosus)、多包条虫(Echinococcus multilocularis)などの条虫類;
肝蛭(Fasciola hepatica,F.gigantica)、ウエステルマン肺吸虫(Paragonimus westermanii)、肥大吸虫(Fasciolopsic bruski)、膵吸虫(Eurytrema pancreaticum,E.coelomaticum)、肝吸虫(Clonorchis sinensis)、日本住血吸虫(Schistosoma japonicum)、ビルハルツ住血吸虫(Schistosoma haematobium)、マンソン住血吸虫(Schistosoma mansoni)などの吸虫類;
エイメリア・テネラ(Eimeria tenella)、エイメリア・アセルブリナ(Eimeria acervulina)、エイメリア・ブルネッチ(Eimeria brunetti)、エイメリア・マクシマ(Eimeria maxima)、エイメリア・ネカトリクス(Eimeria necatrix)、エイメリア・ボビス(Eimeria bovis)、エイメリア・オビノイダリス(Eimeria ovinoidalis)のようなエイメリア類(Eimeria spp.);
クルーズトリパノソーマ(Trypanosomsa cruzi)、リーシュマニア類(Leishmania spp.)、マラリア原虫(Plasmodium spp.)、バベシア類(Babesis spp.)、トリコモナス類(Trichomonadidae spp.)、ヒストモナス類(Histomanas spp.)、ジアルディア類(Giardia spp.)、トキソプラズマ類(Toxoplasma spp.)、赤痢アメーバ(Entamoeba histolytica)、タイレリア類(Theileria spp.)等。 Specific examples of target endoparasites include, but are not limited to, the following.
Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Esphagostomum Genus Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis ), Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris and other nematodes ;
Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa;
Dracunculidae nematodes such as Dracunculus;
Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, tapeworms such as Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus, Echinococcus multilocularis;
Fasciola hepatica, F.gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E.coelomaticum, Clonorchis sinensis, Schistosoma japonicum), Schistosoma haematobium, Schistosoma mansoni, and other flukes;
Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria bovis Eimeria spp., such as Eimeria ovinoidalis;
Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomonas spp., Giardia (Giardia spp.), Toxoplasma spp., Entamoeba histolytica, Theileria spp. and the like.
本発明化合物は、農園芸用殺菌剤としての使用以外に、抗真菌剤としても使用できる。
The compound of the present invention can be used as an antifungal agent in addition to being used as an agricultural and horticultural fungicide.
抗真菌剤として対象となる病原菌としては、以下の具体例が挙げられるが、これらのみに限定されるものではない。
Trichophyton rubrum及びTrichophyton mentagrophytesなどの白癬菌類、Candida albicansなどのカンジダ菌類、Aspergillus fumigatusなどのアスペルギルス菌類、Cryptococcus neoformasなどのクリプトコックス菌類等。 Specific examples of pathogenic bacteria that can be used as antifungal agents include, but are not limited to, the following specific examples.
Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, and the like.
Trichophyton rubrum及びTrichophyton mentagrophytesなどの白癬菌類、Candida albicansなどのカンジダ菌類、Aspergillus fumigatusなどのアスペルギルス菌類、Cryptococcus neoformasなどのクリプトコックス菌類等。 Specific examples of pathogenic bacteria that can be used as antifungal agents include, but are not limited to, the following specific examples.
Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, and the like.
本発明化合物を植物病害及び植物害虫防除剤として施用するにあたっては、通常は、適当な固体担体又は液体担体と混合し、さらに所望により、界面活性剤、浸透剤、展着剤、増粘剤、凍結防止剤、結合剤、固結防止剤、崩壊剤、分解防止剤等を添加して、液剤(Soluble concentrate)、乳剤(emulsifiable concentrate)、水和剤(wettable powder)、水溶剤(water soluble powder)、顆粒水和剤(water dispersible granule)、顆粒水溶剤(water soluble granule)、懸濁剤(suspension concentrate)、乳濁剤(concentrated emulsion)、サスポエマルジョン(suspoemulsion)、マイクロエマルジョン(microemulsion)、粉剤(dustable powder)、粒剤(granule)、ゲル剤(gel)等の任意の剤型の製剤にて実用に供することができる。また、省力化及び安全性向上の観点から、上記任意の剤型の製剤を水溶性包装体に封入して供することもできる。
When applying the compound of the present invention as a plant disease and plant pest control agent, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, Antifreezing agents, binders, anti-caking agents, disintegrants, anti-degradants, etc. are added to prepare soluble concentrates, emulsifiable concentrates, wettable powders, water soluble powders, etc. ), water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, It can be put to practical use in any dosage form such as dustable powder, granule, gel and the like. In addition, from the viewpoint of saving labor and improving safety, the formulation of any dosage form described above can be enclosed in a water-soluble package and provided.
固体担体としては、例えば、石英、カオリナイト、パイロフィライト、セリサイト、タルク、ベントナイト、酸性白土、アタパルジャイト、ゼオライト、珪藻土等の天然鉱物質類、炭酸カルシウム、硫酸アンモニウム、硫酸ナトリウム、塩化カリウム等の無機塩類、合成珪酸、合成珪酸塩等が挙げられる。
Examples of solid carriers include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride and the like. Inorganic salts, synthetic silicic acid, synthetic silicates and the like can be mentioned.
液体担体としては、例えば、エチレングリコール、プロピレングリコール、イソプロパノール等のアルコール類;キシレン、アルキルベンゼン、アルキルナフタレン等の芳香族炭化水素類;ブチルセロソルブ等のエーテル類;シクロヘキサノン等のケトン類;γ-ブチロラクトン等のエステル類;N-メチルピロリドン、N-オクチルピロリドン等の酸アミド類;大豆油、ナタネ油、綿実油、ヒマシ油等の植物油;水;等が挙げられる。これら固体及び液体担体は単独でも2種以上を併用してもよい。
Examples of liquid carriers include alcohols such as ethylene glycol, propylene glycol and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil; water; These solid and liquid carriers may be used alone or in combination of two or more.
界面活性剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンスチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリオキシエチレン脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル等のノニオン性界面活性剤;アルキル硫酸塩、アルキルベンゼンスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、ポリオキシエチレンアルキルアリールエーテル硫酸塩又は燐酸塩、ポリオキシエチレンスチリルフェニルエーテル硫酸塩又は燐酸塩、ポリカルボン酸塩、ポリスチレンスルホン酸塩等のアニオン性界面活性剤;アルキルアミン塩、アルキル4級アンモニウム塩等のカチオン性界面活性剤;アミノ酸型、ベタイン型等の両性界面活性剤;等が挙げられる。
Examples of surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxyethylene Nonionic surfactants such as sorbitan fatty acid esters; alkyl sulfates, alkylbenzenesulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensate of naphthalenesulfonic acid , salts of formalin condensates of alkylnaphthalene sulfonic acids, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates, polycarboxylates, polystyrene sulfonates, etc. active agents; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid type and betaine type;
これら界面活性剤の含有量は、特に限定されるものではないが、本発明の製剤100重量部に対し、通常、0.05~20重量部の範囲が望ましい。また、これら界面活性剤は、単独で用いても2種以上を併用してもよい。
Although the content of these surfactants is not particularly limited, it is usually desirable to be in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention. Moreover, these surfactants may be used alone or in combination of two or more.
本発明化合物を農薬として使用する場合には、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、土壌改良剤等と混合施用してもよい。
When the compound of the present invention is used as an agricultural chemical, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, It may be applied in combination with synergists, fertilizers, soil conditioners and the like.
特に他の農薬或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菌殺虫スペクトラムの拡大、及び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。
In particular, by mixing with other pesticides or plant hormones, it can be expected to reduce costs by reducing the amount of applied chemicals, expand the bactericidal and insecticidal spectrum due to the synergistic action of the mixed chemicals, and have a higher pest control effect. At this time, it is also possible to combine with a plurality of known pesticides at the same time.
一態様において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、ザ・ペスティサイド・マニュアル(The Pesticide Manual)18版、2018年に記載されている化合物等がある。具体的にその一般名を例示すれば、次の通りである。但し、混合使用する農薬は、必ずしもこれらのみに限定されるものではない。
殺菌剤:アシベンゾラル-S-メチル(acibenzolar-S-methyl)、アシペタックス(acypetacs)、アルジモルフ(aldimorph)、アリルアルコール(allyl alcohol)、アメトクトラジン(ametoctradin)、アミノピリフェン(aminopyrifen)、アミスルブロム(amisulbrom)、アンバム(amobam)、アムプロピルホス(ampropylfos)、アニラジン(anilazine)、アザコナゾール(azaconazole)、アジチラム(azithiram)、アゾキシストロビン(azoxystrobin)、バリウムポリサルファイド(barium polysulfide)、ベナラキシル(benalaxyl)、ベナラキシル-M(benalaxyl-M)、ベノダニル(benodanil)、ベノミル(benomyl)、ベンキノックス(benquinox)、ベンタルロン(bentaluron)、ベンチアバリカルブ-イソプロピル(benthiavalicarb-isopropyl)、ベンチアゾール(benthiazole)、ベンザマクリル(benzamacril)、ベンザモルフ(benzamorf)、ベンゾビンディフルピル(benzovindiflupyr)、ビナパクリル(binapacryl)、ビフェニル(biphenyl)、ビテルタノール(bitertanol)、ビキサフェン(bixafen)、ブラストサイジン-S(blasticidin-S)、ボルドー液(bordeaux mixture)、ボスカリド(boscalid)、ブロムコナゾール(bromoconazole)、ブピリメート(bupirimate)、ブチオベート(buthiobate)、ブチルアミン(butylamine)、石灰硫黄合剤(calcium polysulfide)、キャプタフォール(captafol)、キャプタン(captan)、カルバモルフ(carbamorph)、カルベンダジム(carbendazim)、カルボキシン(carboxin)、カルプロパミド(carpropamid)、カルボン(carvone)、チェシュントミクスチャ(cheshunt mixture)、キノメチオネート(chinomethionat)、クロベンチアゾン(chlobenthiazone)、クロラニフォルメタン(chloraniformethane)、クロラニル(chloranil)、クロルフェナゾール(chlorfenazole)、クロロネブ(chloroneb)、クロルピクリン(chloropicrin)、クロロタロニル(chlorothalonil)、クロルキノックス(chlorquinox)、クロゾリネート(chlozolinate)、クリムバゾール(climbazole)、カッパーアセテイト(copper acetate)、塩基性炭酸銅(copper carbonate, basic)、水酸化第二銅(copper hydroxide)、カッパーナフテネート(copper naphthenate)、カッパーオレエート(copper oleate)、塩基性塩化銅(copper oxychloride)、硫酸銅(copper sulfate)、塩基性硫酸銅(copper sulfate, basic)、カッパージンククロメイト(copper zinc chromate)、クモキシストロビン(coumoxystrobin)、クレゾール(cresol)、クフラネブ(cufraneb)、クプロバム(cuprobam)、シアゾファミド(cyazofamid)、シクラフラミド(cyclafuramid)、シクロヘキシミド(cycloheximide)、シフルフェナミド(cyflufenamid)、シモキサニル(cymoxanil)、シペンダゾール(cypendazole)、シプロコナゾール(cyproconazole)、シプロジニル(cyprodinil)、シプロフラム(cyprofuram)、ダゾメット(dazomet)、デバカルブ(debacarb)、デカフェンチン(decafentin)、デハイドロアセテイト(dehydroacetic acid)、ジクロベンチアゾクス(dichlobentiazox)、ジクロフルアニド(dichlofluanid)、ジクロン(dichlone)、ジクロロフェン(dichlorophen)、ジクロゾリン(dichlozoline)、ジクロブトラゾール(diclobutrazol)、ジクロシメット(diclocymet)、ジクロメジン(diclomezine)、ジクロラン(dicloran)、ジエトフェンカルブ(diethofencarb)、ジフェノコナゾール(difenoconazole)、ジフルメトリム(diflumetorim)、ジメチリモール(dimethirimol)、ジメトモルフ(dimethomorph)、ジモキシストロビン(dimoxystrobin)、ジニコナゾール(diniconazole)、ジニコナゾール-M(diniconazole-M)、ジノブトン(dinobuton)、ジノカップ(dinocap)、ジノカップ-4(dinocap-4)、ジノカップ-6(dinocap-6)、ジノクトン(dinocton)、ジノスルフォン(dinosulfon)、ジノテルボン(dinoterbon)、ジフェニルアミン(diphenylamine)、ジピメチトロン(dipymetitrone)、ジピリチオン(dipyrithione)、ジスルフィラム(disulfiram)、ジタリムホス(ditalimfos)、ジチアノン(dithianon)、デーエヌオーシー(DNOC)、ドデモルフ(dodemorph)、ドジン(dodine)、ドラゾキソロン(drazoxolon)、エディフェンホス(edifenphos)、エネストロビン(enestrobin)、エノキサストロビン(enoxastrobin)、エポキシコナゾール(epoxiconazole)、エタボキサム(ethaboxam)、エタコナゾール(etaconazole)、エテム(etem)、エチリモール(ethirimol)、エトキシキン(ethoxyquin)、エトリジアゾール(etridiazole)、ファモキサドン(famoxadone)、フェナミドン(fenamidone)、フェナミノスルフ(fenaminosulf)、フェナミンストロビン(fenaminstrobin)、フェナパニル(fenapanil)、フェナリモル(fenarimol)、フェンブコナゾール(fenbuconazole)、フェンフラム(fenfuram)、フェンヘキサミド(fenhexamid)、フェニトロパン(fenitropan)、フェノキサニル(fenoxanil)、フェンピクロニル(fenpiclonil)、フェンピコキサミド(fenpicoxamid)、フェンプロピジン(fenpropidin)、フェンプロピモルフ(fenpropimorph)、フェンピラザミン(fenpyrazamine)、フェンチン(fentin)、ファーバム(ferbam)、フェリムゾン(ferimzone)、フロリルピコキサミド(florylpicoxamid)、フルアジナム(fluazinam)、フルジオキソニル(fludioxonil)、フルフェノキシストロビン(flufenoxystrobin)、フルインダピル(fluindapyr)、フルメトベル(flumetover)、フルモルフ(flumorph)、フルオピコリド(fluopicolide)、フルオピモミド(fluopimomide)、フルオピラム(fluopyram)、フルオルイミド(fluoroimide)、フルオトリマゾール(fluotrimazole)、フルオキサピプロリン(fluoxapiprolin)、フルオキサストロビン(fluoxastrobin)、フルキンコナゾール(fluquinconazole)、フルシラゾール(flusilazole)、フルスルファミド(flusulfamide)、フルトラニル(flutolanil)、フルチアニル(flutianil)、フルトリアホール(flutriafol)、フルキサピロキサド(fluxapyroxad)、フォルペット(folpet)、ホセチル-アルミニウム(fosetyl-aluminium)、フサライド(fthalide)、フベリダゾール(fuberidazole)、フララキシル(furalaxyl)、フラメトピル(furametpyr)、フルカルバニル(furcarbanil)、フルコナゾール(furconazole)、フルコナゾール-シス(furconazole-cis)、フルメシクロックス(furmecyclox)、フロファネート(furophanate)、グリジン(glyodin)、グリセオフルビン(griseofulvin)、グアザチン(guazatine)、ハラクリネート(halacrinate)、ヘキサクロロベンゼン(hexachlorobenzene)、ヘキサコナゾール(hexaconazole)、ヘキシルチオフォス(hexylthiofos)、硫酸オキシキノリン(8-hydroxyquinoline sulfate)、ヒメキサゾール(hymexazol)、イマザリル(imazalil)、イミベンコナゾール(imibenconazole)、イミノクタジン-アルベシル酸塩(iminoctadine-albesilate)、イミノクタジン酢酸塩(iminoctadine-triacetate)、インピルフルキサム(inpyrfluxam)、イオドカルブ(iodocarb)、イプコナゾール(ipconazole)、イプフェントリフルコナゾール(ipfentrifluconazole)、イプフルフェノキン(ipflufenoquin)、イプロベンホス(iprobenfos)、イプロジオン(iprodione)、イプロバリカルブ(iprovalicarb)、イソフェタミド(isofetamid)、イソフルシプラム(isoflucypram)、イソチアニル(isotianil)、イソプロチオラン(isoprothiolane)、イソピラザム(isopyrazam)、イソバレジオン(isovaledione)、カスガマイシン(kasugamycin)、クレソキシム-メチル(kresoxim-methyl)、ラミナリン(laminarin)、マンカッパー(mancopper)、マンコゼブ(mancozeb)、マンデストロビン(mandestrobin)、マンジプロパミド(mandipropamid)、マンネブ(maneb)、メベニル(mebenil)、メカルビンジッド(mecarbinzid)、メフェントリフルコナゾール(mefentrifluconazole)、メパニピリム(mepanipyrim)、メプロニル(mepronil)、メプチルジノカップ(meptyldinocap)、メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M)、メタム(metam)、メタゾキソロン(metazoxolon)、メトコナゾール(metconazole)、メタスルホカルブ(methasulfocarb)、メトフロキサム(methfuroxam)、メチルテトラプロール(metyltetraprole)、メチラム(metiram)、メトミノストロビン(metominostrobin)、メトラフェノン(metrafenone)、メトスルフォバックス(metsulfovax)、ミルネブ(milneb)、ミクロブタニル(myclobutanil)、ミクロゾリン(myclozolin)、ナーバム(nabam)、ナフティフィン(naftifine)、ナタマイシン(natamycin)、有機ニッケル(nickel bis (dimethyldithiocarbamate))、ニトロスチレン(nitrostyrene)、ニトロタル-イソプロピル(nitrothal-isopropyl)、ヌアリモール(nuarimol)、オクチノリン(octhilinone)、オフレース(ofurace)、オリサストロビン(orysastrobin)、オキサジキシル(oxadixyl)、オキサチアピプロリン(oxathiapiprolin)、オキシキノリン銅(oxine copper)、オキスポコナゾールフマル酸塩(oxpoconazole fumarate)、オキシカルボキシン(oxycarboxin)、ペフラゾエート(pefurazoate)、ペンコナゾール(penconazole)、ペンシクロン(pencycuron)、ペンフルフェン(penflufen)、ペンタクロロフェノール(pentachlorophenol)、ペンチオピラド(penthiopyrad)、オルソフェニルフェノール(2-phenylphenol)、ホスダイフェン(phosdiphen)、フサライド(phthalide)、ピカルブトラゾクス(picarbutrazox)、ピコキシストロビン(picoxystrobin)、ピペラリン(piperalin)、ポリカーバメート(polycarbamate)、ポリオキシン(polyoxins)、ポリオキシン-D(polyoxorim)、ポタシウムアジド(potassium azide)、炭酸水素カリウム(potassium hydrogen carbonate)、プロベナゾール(probenazole)、プロクロラズ(prochloraz)、プロシミドン(procymidone)、プロパモカルブ塩酸塩(propamocarb hydrochloride)、プロピコナゾール(propiconazole)、プロピネブ(propineb)、プロキナジド(proquinazid)、プロチオカルブ(prothiocarb)、ピラゾホス(pyrazophos)、ピリベンカルブ(pyribencarb)、ピリフェノックス(pyrifenox)、ピリメタニル(pyrimethanil)、ピリミノストロビン(pyriminostrobin)、ピロキロン(pyroquilon)、
プロチオカルブ(prothiocarb)、プロチオコナゾール(prothioconazole)、ピジフルメトフェン(pydiflumetofen)、ピラカルボリド(pyracarbolid)、ピラクロストロビン(pyraclostrobin)、ピラメトストロビン(pyrametostrobin)、ピラオキシストロビン(pyraoxystrobin)、ピラプロポイン(pyrapropoyne)、ピラジフルミド(pyraziflumid)、ピリダクロメチル(pyridachlometyl)、ピリジニトリル(pyridinitril)、ピリオフェノン(pyriofenone)、ピリソキサゾール(pyrisoxazole)、ピロキシクロル(pyroxychlor)、ピロキシフル(pyroxyfur)、キナセトール-スルフェート(quinacetol-sulfate)、キナザミド(quinazamid)、キンコナゾール(quinconazole)、キノキシフェン(quinoxyfen)、キノフメリン(quinofumelin)、キントゼン(quintozene)、ラベンザゾール(rabenzazole)、サリチルアニリド(salicylanilide)、セダキサン(sedaxane)、シルチオファム(silthiofam)、シメコナゾール(simeconazole)、炭酸水素ナトリウム(sodium hydrogen carbonate)、次亜塩素酸ナトリウム(sodium hypochlorite)、スピロキサミン(spiroxamine)、硫黄(sulfur)、テブコナゾール(tebuconazole)、テブフロキン(tebufloquin)、テフロクタラム(tecloftalam)、テクナゼン(tecnazene)、テコラム(tecoram)、テトラコナゾール(tetraconazole)、チアベンダゾール(thiabendazole)、チアジフルオール(thiadifluor)、チシオフェン(thicyofen)、チフルザミド(thifluzamide)、チオクロルフェンヒム(thiochlorfenphim)、チオファネート(thiophanate)、チオファネート-メチル(thiophanate-methyl)、チウラム(thiram)、チアジニル(tiadinil)、チオキシミド(tioxymid)、トルクロホス-メチル(tolclofos-methyl)、トルプロカルブ(tolprocarb)、トリルフルアニド(tolylfluanid)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリアミホス(triamiphos)、トリアリモール(triarimol)、トリアズブチル(triazbutil)、トリアゾキシド(triazoxide)、トリブチル錫オキシド(tributyltin oxide)、トリクラミド(trichlamide)、トリクロピリカルブ(triclopyricarb)、トリシクラゾール(tricyclazole)、トリデモルフ(tridemorph)、トリフロキシストロビン(trifloxystrobin)、トリフルミゾール(triflumizole)、トリホリン(triforine)、トリチコナゾール(triticonazole)、バリダマイシン(validamycin)、バリフェナレート(valifenalate)、ビンクロゾリン(vinclozolin)、ザリラミド(zarilamid)、ジンクナフテネート(zinc naphthenate)、硫酸亜鉛(zinc sulfate)、ジネブ(zineb)、ジラム(ziram)、ゾキサミド(zoxamide)、シイタケ菌糸体抽出物(shiitake mycelium extract)及びシイタケ子実体抽出物(shiitake fruiting body extract)等。
殺虫剤:アバメクチン(abamectin)、アセフェート(acephate)、アセキノシル(acequinocyl)、アセタミプリド(acetamiprid)、アクリナトリン(acrinathrin)、アシノナピル(acynonapyr)、アフィドピロペン(afidopyropen)、アフォクソラネル(afoxolaner)、アラニカルブ(alanycarb)、アルジカルブ(aldicarb)、アレスリン(allethrin)、アルファ-シペルメトリン(alpha-cypermethrin)、アルファ-エンドスルファン(alpha-endosulfan)、アミドフルメット(amidoflumet)、アミトラズ(amitraz)、アザメチホス(azamethiphos)、アジンホス-エチル(azinphos-ethyl)、アジンホス-メチル(azinphos-methyl)、アゾシクロチン(azocyclotin)、バチルスチューリンゲンシス(bacillus thuringiensis)、ベンダイオカルブ(bendiocarb)、ベンフルトリン(benfluthrin)、ベンフラカルブ(benfuracarb)、ベンスルタップ(bensultap)、ベンゾキシメート(benzoximate)、ベンズピリモキサン(benzpyrimoxan)、ベータ-シフルトリン(beta-cyfluthrin)、ベータ-シペルメトリン(beta-cypermethrin)、ビフェナゼート(bifenazate)、ビフェントリン(bifenthrin)、ビオアレスリン(bioallethrin)、ビオレスメトリン(bioresmethrin)、ビストリフルロン(bistrifluron)、ブロフラニリド(broflanilide)、ブロモプロピレート(bromopropylate)、ブプロフェジン(buprofezin)、ブトカルボキシム(butocarboxim)、カルバリル(carbaryl)、カルボフラン(carbofuran)、カルボスルファン(carbosulfan)、カルタップ(cartap)、チノメチオネート(chinomethionat)、クロルアントラニリプロール(chlorantraniliprole)、クロルエトキシホス(chlorethxyfos)、クロルフェナピル(chlorfenapyr)、クロルフェンビンホス(chlorfenvinphos)、クロルフルアズロン(chlorfluazuron)、クロルメホス(chlormephos)、クロロベンジラート(chlorobezilate)、クロロプラレスリン(chloroprallethrin)、クロルピリホス(chlorpyrifos)、クロピリホス-メチル(chlorpyrifos-methyl)、クロマフェノジド(chromafenozide)、クロフェンテジン(clofentezine)、クロチアニジン(clothianidin)、シアノホス(cyanophos)、シアントラニリプロール(cyantraniliprole)、シクラニリプロール(cyclaniliprole)、シクロプロトリン(cycloprothrin)、シエノピラフェン(cyenopyrafen)、cyetpyrafen(cyetpyrafen)、シフルメトフェン(cyflumetofen)、シフルトリン(cyfluthrin)、シハロジアミド(cyhalodiamide)、シハロトリン(cyhalothrin)、サイヘキサチン(cyhexatine)、シペルメトリン(cypermethrin)、シフェノトリン(cyphenothrin)、cyproflanilide(cyproflanilide)、シロマジン(cyromazine)、デルタメトリン(deltamethrin)、ジアクロデン(diacloden)、ジアフェンチウロン(diafenthiuron)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos)、ジクロロメゾチアズ(dicloromezotiaz)、ジコホール(dicofol)、ジエノクロル(dienochlor)、ジフロビダジン(diflovidazin)、ジフルベンズロン(diflubenzuron)、ジメフルトリン(dimefluthrin)、ジメトエート(dimethoate)、ジメチルビンホス(dimethylvinphos)、ジンプロピリダズ(dimpropyridaz)、ジノテフラン(dinotefuran)、ジオフェノラン(diofenolan)、ジスルフォトン(disulfoton)、デーエヌオーシー(DNOC)、d-T-80-フタルスリン(d-tetramethrin)、エマメクチンベンゾエート(emamectin-benzoate)、エンペントリン(empenthrin)、エンドスルファン(endosulfan)、イーピーエヌ(EPN)、イプシロン-メトフルトリン(epsilon-metofluthrin)、イプシロン-モムフルオロトリン(epsilon-momfluorothrin)、エスフェンバレレート(esfenvalerate)、エチオフェンカルブ(ethiofencarb)、エチプロール(ethiprole)、エトフェンプロックス(etofenprox)、エトキサゾール(etoxazole)、エトリムホス(etrimfos)、フェバンテル(Febantel)、フェナザキン(fenazaquin)、フェンブタチンオキシド(fenbutatin oxide)、フェニトロチオン(fenitrothion)、フェンメゾジチアズ(fenmezoditiaz)、フェノブカルブ(fenobucarb)、フェノチオカルブ(fenothiocarb)、フェノキシカルブ(fenoxycarb)、フェンプロパトリン(fenpropathrin)、フェンピロキシメート(fenpyroximate)、フェンチオン(fenthion)、フェンバレレート(fenvalerate)、フィプロニル(fipronil)、フロメトキン(flometoquin)、フロニカミド(flonicamid)、フルアクリピリム(fluacrypyrim)、フルアズロン(fluazuron)、フルベンジアミド(flubendiamide)、fluchlordiniliprole(fluchlorodiniliprole)、フルシクロクスロン(flucycloxuron)、フルシトリネート(flucythrinate)、フルフェネリム(flufenerim)、フルフェノクスロン(flufenoxuron)、フルフェンプロックス(flufenprox)、フルフィプロール(flufiprole)、フルヘキサホン(fluhexafon)、フルメトリン(flumethrin)、フルペンチオフェノックス(flupentiofenox)、フルピラジフロン(flupyradifurone)、フルピリミン(flupyrimin)、フルララネル(fluralaner)、フルバリネート(fluvalinate)、フルキサメタミド(fluxametamide)、ホノホス(fonophos)、ホルメタネート(formetanate)、フォルモチオン(formothion)、フラチオカルブ(furathiocarb)、ガンマ-シハロトリン(gamma-cyhalothrin)、ハルフェンプロックス(halfenprox)、ハロフェノジド(halofenozide)、ヘプタフルトリン(heptafluthrin)、ヘキサフルムロン(hexaflumuron)、ヘキシチアゾクス(hexythiazox)、ヒドラメチルノン(hydramethylnon)、イミダクロプリド(imidacloprid)、イミプロトリン(imiprothrin)、indazapyroxamet(indazapyroxamet)、インドキサカルブ(indoxacarb)、インドキサカルブ-MP(indoxacarb-MP)、イソシクロセラム(isocycloseram)、イソフェンホス(isofenphos)、イソプロカルブ(isoprocarb)、イソキサチオン(isoxathion)、カッパ-ビフェントリン(kappa-bifenthrin)、カッパ-テフルトリン(kappa-tefluthrin)、ラムダ-シハロトリン(lambda-cyhalothrin)、レピメクチン(lepimectin)、ルフェヌロン(lufenuron)、マラチオン(malathion)、メペルフルスリン(meperfluthrin)、メタフルミゾン(metaflumizone)、メタルカルブ(metalcarb)、メタルデヒド(metaldehyde)、メタクリホス(methacrifos)、メタミドホス(methamidophos)、メチダチオン(methidathion)、メソミル(methomyl)、メソプレン(methoprene)、メトキシクロル(methoxychlor)、メトキシフェノジド(methoxyfenozide)、臭化メチル(methyl bromide)、メトフルトリン(metofluthrin)、ミルベメクチン(milbemectin)、モムフルオロトリン(momfluorothrin)、モノクロトホス(monocrotophos)、ムスカルア(muscalure)、nicofluprole(nicofluprole)、ニテンピラム(nitenpyram)、ノバルロン(novaluron)、ノビフルムロン(noviflumuron)、オメトエート(omethoate)、オキサゾスルフィル(oxazosulfyl)、オキシデメトン-メチル(oxydemeton-methyl)、オキシデプロホス(oxydeprofos)、パラチオン(parathion)、パラチオン-メチル(parathion-methyl)、ペンタクロロフェノール(pentachlorophenol)、ペルメトリン(permethrin)、フェノトリン(phenothrin)、フェントエート(phenthoate)、ホレート(phorate)、ホサロン(phosalone)、ホスメット(phosmet)、ホスファミドン(phosphamidon)、ホキシム(phoxim)、ピリミカーブ(pirimicarb)、ピリミホス-メチル(pirimiphos-methyl)、プラジクアンテル(Praziquantel)、プロフェノホス(profenofos)、プロフルトリン(profluthrin)、プロパホス(propaphos)、プロパルギット(propargite)、プロチオホス(prothiofos)、プロトリフェンブト(protrifenbute)、ピフルブミド(pyflubumide)、ピメトロジン(pymetrozine)、ピラクロホス(pyraclofos)、ピラフルプロール(pyrafluprole)、ピレトリン(pyrethrins)、ピリダベン(pyridaben)、ピリダリル(pyridalyl)、ピリフルキナゾン(pyrifluquinazon)、ピリミジフェン(pyrimidifen)、ピリプロール(pyriprole)、ピリプロキシフェン(pyriproxyfen)、レスメトリン(resmethrin)、ロテノン(rotenone)、シラフルオフェン(silafluofen)、spidoxamat(spidoxamat)、スピネトラム(spinetoram)、スピノサド(spinosad)、スピロジクロフェン(spirodiclofen)、スピロメシフェン(spiromesifen)、スピロピジオン(spiropidion)、スピロテトラマート(spirotetramat)、スピロメシフェン(spyromesifen)、スルホテップ(sulfotep)、スルホキサフロル(sulfoxaflor)、スルプロホス(sulprofos)、タウ-フルバリネート(tau-fluvalinate)、テブフェノジド(tebfenozide)、テブフェンピラド(tebufenpyrad)、テフルベンズロン(teflubenzuron)、テフルトリン(tefluthorin)、テルブホス(terbufos)、テトラクロラントラニリプロール(tetrachlorantraniliprole)、テトラクロロビンホス(tetrachlorvinphos)、テトラメトリン(tetramethrin)、テトラメチルフルスリン(tetramethylfluthrin)、テトラニリプロール(tetraniliprole)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、チオシクラム(thiocyclam)、チオジカルブ(thiodicarb)、チオファノックス(thiofanox)、チオメトン(thiometon)、トルフェンピラド(tolfenpyrad)、トラロメトリン(tralomethrin)、トランスフルトリン(transfluthrin)、トリアザメート(triazamate)、トリアズロン(triazuron)、トリクロルホン(trichlorfon)、トリフルメゾピリム(triflumezopyrim)、トリフルムロン(triflumuron)、チクロピラゾフロル(tyclopyrazoflor)、バミドチオン(vamidothion)及びゼタ-シペルメトリン(zeta-cypermethrin)等。
寄生虫薬:エスフェンバレレート(esfenvalerate)、フェンプロパトリン(fenpropathrin)、フェンバレレート(fenvalerate)、アルファシペルメトリン(cypermethrin)、ビフェントリン(bifenthrin)、シペルメトリン(cypermethrin)、デルタメトリン(deltamethrin)、エトフェンプロックス(etofenprox)、ラムダシハロトリン(lambda-cyhalothrin)、ペルメトリン(permethrin)、テフルトリン(tefluthrin)、ゼータシペルメトリン(zeta-cypermethrin)、アセタミプリド(acetamiprid)、クロチアニジン(clothianidin)、ジノテフラン(dinotefuran)、イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、チアメトキサム(thiamethoxam)、クロマフェノジド(chromafenozide)、フェノキシカルブ(fenoxycarb)、ルフェヌロン(lufenuron)、メトプレン(methoprene)、ピリプロキシフェン(pyriproxyfen)、トリフルムロン(triflumuron)、クロルピリホス(chlorpyrifos)、クロルピリホスメチル(chlorpyrifos-methyl)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos)、フェニトロチオン(fenitrothion)、フェンチオン(fenthion)、マラチオン(malathion)、ピリミホスメチル(pirimiphos-methyl)、テトラクロロビンホス(tetrachlorvinphos)、エチプロール(ethiprole)、フィプロニル(fipronil)、プロポキスル(propoxur)、カルバリル(carbaryl)、ベンジオカルブ(bendiocarb)、メトキサジアゾン(metoxadiazone)、フェノカルブ(fenobucarb)、カルボフラン(carbofuran)、アフォキソラネル(afoxolaner)、フルララネル(fluralaner)、フルキサメタミド(fluxametamide)、サロラネル(sarolaner)、ロティラネル(lotilaner)、チゴラネル(tigolaner)、esafoxolaner(esafoxolaner)、modoflaner(modoflaner)、umifoxolaner(umifoxolaner)、mivorilaner(mivorilaner)、アベルメクチン(avermectin)、イベルメクチン(ivermectin)、ドラメクチン(doramectin)、エプリノメクチン(eprinomectin)、マデユラマイシン(maduramycin)、ミルベマイシン(milbemycin)、ミルベマイシンオキシム(milbemycin oxime)、モキシデクチン(moxidectin)、セラメクチン(selamectin)、インドキサカルブ(indoxacarb)、アミトラズ(amitraz)、ビストリフルロン(bistrifluron)、スピノサド(spinosad)、アルベンダゾール(albendazole)、アトバコン(atovaquone)、ビチオノール(bithionol)、カンベンダゾール(cambendazole)、カルニダゾール(carnidazole)、クロロキン(chloroquine)、クラズリル(clazuril)、クロルスロン(clorsulon)、クロサンテル(closantel)、クマホス(coumaphos)、ジクロロフェン(dichlorophen)、ジエチルカルバマジン(diethylcarbamazine)、ジミナゼン(diminazene)、ジニトルミド(dinitolmide)、ヨウ化ジチアザニン(dithiazanine iodide)、エモデプシド(emodepside)、エプシプランテル(epsiprantel)、フェバンテル(febantel)、フェンベンダゾール(fenbendazole)、フルベンダゾール(flubendazole)、グリカルピラミド(glycalpyramide)、イミドカルブ(imidocarb)、レバミゾール(levamisole)、メベンダゾール(mebendazole)、メベンダゾール(mebendazole)、メフロキン塩酸塩(mefloquine hydrochloride)、メラルソミン二塩酸塩(melarsamine hydrochloride)、メトロニダゾール(metronidazole)、メチリジン(metyridine)、モネパンテル(monepantel)、酒石酸モランテル(morantel tartrate)、ニクロサミド(niclosamide)、パモ酸オキサンテル(oxantel pamoate)、酒石酸オキサンテル(oxantel tartrate)、オキシベンダゾール(oxibendazole)、オキシクロザニド(oxyclozanide)、アジピン酸ピペラジン(piperazine adipate)、クエン酸ピペラジン(piperazine citrate)、リン酸ピペラジン(piperazine phosphate)、プラジカンテル(praziquantel)、パモ酸ピランテル(pyrantel pamoate)、ラフォキサニド(rafoxanide)、テトラミソール塩酸塩(tetramisole hydrochloride)、チアベンダゾール(thiabendazole)及びトリクラベンダゾール(triclabendazole)等。
抗真菌剤:ケトコナゾール(ketoconazole)及びミコナゾール硝酸塩(miconazole nitrate)など。
抗菌剤:アモキシシリン(amoxicillin)、アンピシリン(ampicillin)、ベトキサジン(bethoxazin)、ビチオノール(bithionol)、ブロノポール(bronopol)、セファピリン(cefapirin)、セファゾリン(cefazolin)、セフキノム(cefquinome)、セフチオフル(ceftiofur)、クロルテトラサイクリン(chlortetracycline)、クラブラン酸(clavulanic acid)、ダノフロキサシン(danofloxacin)、ジフロキサシン(difloxacin)、ジニトルミド(dinitolmide)、エンロフロキサシン(enrofloxacin)、フロルフェニコール(florfenicol)、リンコマイシン(lincomycin)、ロメフロキサシン(lomefloxacin)、マルボフロキサシン(marbofloxacin)、ミロキサシン(miloxacin)、ミロサマイシン(mirosamycin)、ニトラピリン(nitrapyrin)、ノルフロキサシン(norfloxacin)、オクチリノン(octhilinone)、オフロキサシン(ofloxacin)、オルビフロキサシン(orbifloxacin)、オキソリニック酸(oxolinic acid)、オキシテトラサイクリン(oxytetracycline)、ペニシリン(penicillin)、ストレプトマイシン(streptomycin)、チアンフェニコール(thiamphenicol)、フマル酸チアムリン(tiamulin fumarate)、リン酸チルミコシン(tilmicosin phosphate)、酢酸イソ吉草酸タイロシン(acetylisovaleryltylosin)、リン酸タイロシン(tylosin phosphate)、ツラスロマイシン(tulathromycin)、バルネムリン(valnemulin)、貝殻焼成カルシウム(酸化カルシウム)、タラロマイセス属菌、トリコデルマ属菌及びユニオチリウム属菌など。 In one aspect, the types of pesticides used in combination with the compound of the present invention include, for example, the compounds described in The Pesticide Manual, 18th Edition, 2018. Specific examples of common names are as follows. However, pesticides used in combination are not necessarily limited to these.
Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (benalaxyl-M), benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, bordeaux mixture, boscalid, bromconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph ( carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture, chinomethionat, clobenzazone hiazone), chloraniformmethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, clozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate, coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil ), cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid, dichlobentiazox, dichlofluanid, dichlone ), dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine, dicloran, diethofe diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton ), dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbone, diphenylamine, dipymetitrone , dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone (famoxadone), fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph ( fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, fluconazole, fluconazole-furconazole -cis), furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexyl Thiophos (hexylthiofos), 8-hydroxyquinoline sulfate, hymexazol, imaza imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isofrucypram, isotianil, isoprothiolane ( isoprothiolane, isopyrazam, isovaledione, kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl ( metalaxyl), metalaxyl-M, metam, metazoxolon, metconazole, metasulfocarb, methfuroxam, methyltetraprole, metiram , metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil il), myclozolin, nabam, naftifine, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol (nuarimol), octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxine copper, oxpoconazole fumarate fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol , phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, Potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb , proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox (p yrifenox), pyrimethanil, pyriminostrobin, pyroquilon,
prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne ), pyraziflumid, pyridaclomethyl, pyridinitril, pyriofenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamide ( quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, sedaxane, silthiofam, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecorum (tecoram), tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl ( thiophanate-methyl), thiram, tiadini l), tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol ( triarimol, triazbutil, triazoxide, tributyltin oxide, trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin , triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract and shiitake fruiting body extract and the like.
Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb ( aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethifos, azinphos-ethyl ), azinphos-methyl, azocyclotin, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate ( benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin , bistrifluron, broflanilide, bromopropylate, buprofezin, butocarbboxim, carbaryl, carbofuran, carbosulfan, cartap (cartap), chinomethionat, chlorantraniliprole, chlorethoxyfos, chlorfe napyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos -methyl), chromafenozide, clofentezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide , cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dichloromezotiaz, dicofol, dienochlor ), diflovidazin, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, day DNOC, dT-80-phthalthuri d-tetramethrin, emamectin-benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, febantel, fenazaquin, fenbutatin oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvale fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubendiamide, fluchlordiniliprole (fluchlorodiniliprole), flucycloxuron, flu citrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyrimin, fluralaner laner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb ( indoxacarb, indoxacarb-MP, isocycloseram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin -tefluthrin), lambda-cyhalothrin, lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalcarb, metaldehyde, methacrifos ( methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, metofluthrin, milbemectin , momfluorothrin, monocrotophos, muscar muscalure, nicofluprole, nitenpyram, novaluron, noviflumuron, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos (oxydeprofos), parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, forate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-methyl, praziquantel, profenofos, profluthrin, propaphos, propargite (propargite), prothiofos, protrifenbute, pyflubumide, pymetrozine, pyraclofos, pyrafluprole, pyrethrins, pyridaben, pyridalyl pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfen, resmethrin, rotenone, silafluofen, spidoxamat, spinetoram , spinosad, spirodiclofen, spiromesifen, spiropidion ion), spirotetramat, spyromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebfenozide, tebufenpyrad ), teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion and zeta-cypermethrin -cypermethrin), etc.
Parasiticides: esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox ( etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid ), nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos, ethiprole ( ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenobucarb, carbofuran, afoxolaner, fluralaner, fluxametamide ( fluxametamide), sarolaner, lotilaner, tigora tigolaner, esafoxolaner, modoflaner (modoflaner), umifoxolaner (umifoxolaner), mivorilaner (mivorilaner), avermectin, ivermectin, doramectin, eprinomectin, maduramycin, milbemycin, milbemycin oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole ), atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide, emodepside, epsiprantel, febantel, fenbendazole , flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride , metronidazole , methyridine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, Thiabendazole and triclabendazole and the like.
Antifungal agents: such as ketoconazole and miconazole nitrate.
Antibiotics: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline chlortetracycline, clavulanic acid, danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin ( lomefloxacin, marbofloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinics oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, tylosin acetate isovalerate (acetylisovaleryltylosin), tylosin phosphate, tulathromycin, valnemulin, calcined shell calcium (calcium oxide), Talaromyces spp., Trichoderma spp. and Uniothylium spp.
殺菌剤:アシベンゾラル-S-メチル(acibenzolar-S-methyl)、アシペタックス(acypetacs)、アルジモルフ(aldimorph)、アリルアルコール(allyl alcohol)、アメトクトラジン(ametoctradin)、アミノピリフェン(aminopyrifen)、アミスルブロム(amisulbrom)、アンバム(amobam)、アムプロピルホス(ampropylfos)、アニラジン(anilazine)、アザコナゾール(azaconazole)、アジチラム(azithiram)、アゾキシストロビン(azoxystrobin)、バリウムポリサルファイド(barium polysulfide)、ベナラキシル(benalaxyl)、ベナラキシル-M(benalaxyl-M)、ベノダニル(benodanil)、ベノミル(benomyl)、ベンキノックス(benquinox)、ベンタルロン(bentaluron)、ベンチアバリカルブ-イソプロピル(benthiavalicarb-isopropyl)、ベンチアゾール(benthiazole)、ベンザマクリル(benzamacril)、ベンザモルフ(benzamorf)、ベンゾビンディフルピル(benzovindiflupyr)、ビナパクリル(binapacryl)、ビフェニル(biphenyl)、ビテルタノール(bitertanol)、ビキサフェン(bixafen)、ブラストサイジン-S(blasticidin-S)、ボルドー液(bordeaux mixture)、ボスカリド(boscalid)、ブロムコナゾール(bromoconazole)、ブピリメート(bupirimate)、ブチオベート(buthiobate)、ブチルアミン(butylamine)、石灰硫黄合剤(calcium polysulfide)、キャプタフォール(captafol)、キャプタン(captan)、カルバモルフ(carbamorph)、カルベンダジム(carbendazim)、カルボキシン(carboxin)、カルプロパミド(carpropamid)、カルボン(carvone)、チェシュントミクスチャ(cheshunt mixture)、キノメチオネート(chinomethionat)、クロベンチアゾン(chlobenthiazone)、クロラニフォルメタン(chloraniformethane)、クロラニル(chloranil)、クロルフェナゾール(chlorfenazole)、クロロネブ(chloroneb)、クロルピクリン(chloropicrin)、クロロタロニル(chlorothalonil)、クロルキノックス(chlorquinox)、クロゾリネート(chlozolinate)、クリムバゾール(climbazole)、カッパーアセテイト(copper acetate)、塩基性炭酸銅(copper carbonate, basic)、水酸化第二銅(copper hydroxide)、カッパーナフテネート(copper naphthenate)、カッパーオレエート(copper oleate)、塩基性塩化銅(copper oxychloride)、硫酸銅(copper sulfate)、塩基性硫酸銅(copper sulfate, basic)、カッパージンククロメイト(copper zinc chromate)、クモキシストロビン(coumoxystrobin)、クレゾール(cresol)、クフラネブ(cufraneb)、クプロバム(cuprobam)、シアゾファミド(cyazofamid)、シクラフラミド(cyclafuramid)、シクロヘキシミド(cycloheximide)、シフルフェナミド(cyflufenamid)、シモキサニル(cymoxanil)、シペンダゾール(cypendazole)、シプロコナゾール(cyproconazole)、シプロジニル(cyprodinil)、シプロフラム(cyprofuram)、ダゾメット(dazomet)、デバカルブ(debacarb)、デカフェンチン(decafentin)、デハイドロアセテイト(dehydroacetic acid)、ジクロベンチアゾクス(dichlobentiazox)、ジクロフルアニド(dichlofluanid)、ジクロン(dichlone)、ジクロロフェン(dichlorophen)、ジクロゾリン(dichlozoline)、ジクロブトラゾール(diclobutrazol)、ジクロシメット(diclocymet)、ジクロメジン(diclomezine)、ジクロラン(dicloran)、ジエトフェンカルブ(diethofencarb)、ジフェノコナゾール(difenoconazole)、ジフルメトリム(diflumetorim)、ジメチリモール(dimethirimol)、ジメトモルフ(dimethomorph)、ジモキシストロビン(dimoxystrobin)、ジニコナゾール(diniconazole)、ジニコナゾール-M(diniconazole-M)、ジノブトン(dinobuton)、ジノカップ(dinocap)、ジノカップ-4(dinocap-4)、ジノカップ-6(dinocap-6)、ジノクトン(dinocton)、ジノスルフォン(dinosulfon)、ジノテルボン(dinoterbon)、ジフェニルアミン(diphenylamine)、ジピメチトロン(dipymetitrone)、ジピリチオン(dipyrithione)、ジスルフィラム(disulfiram)、ジタリムホス(ditalimfos)、ジチアノン(dithianon)、デーエヌオーシー(DNOC)、ドデモルフ(dodemorph)、ドジン(dodine)、ドラゾキソロン(drazoxolon)、エディフェンホス(edifenphos)、エネストロビン(enestrobin)、エノキサストロビン(enoxastrobin)、エポキシコナゾール(epoxiconazole)、エタボキサム(ethaboxam)、エタコナゾール(etaconazole)、エテム(etem)、エチリモール(ethirimol)、エトキシキン(ethoxyquin)、エトリジアゾール(etridiazole)、ファモキサドン(famoxadone)、フェナミドン(fenamidone)、フェナミノスルフ(fenaminosulf)、フェナミンストロビン(fenaminstrobin)、フェナパニル(fenapanil)、フェナリモル(fenarimol)、フェンブコナゾール(fenbuconazole)、フェンフラム(fenfuram)、フェンヘキサミド(fenhexamid)、フェニトロパン(fenitropan)、フェノキサニル(fenoxanil)、フェンピクロニル(fenpiclonil)、フェンピコキサミド(fenpicoxamid)、フェンプロピジン(fenpropidin)、フェンプロピモルフ(fenpropimorph)、フェンピラザミン(fenpyrazamine)、フェンチン(fentin)、ファーバム(ferbam)、フェリムゾン(ferimzone)、フロリルピコキサミド(florylpicoxamid)、フルアジナム(fluazinam)、フルジオキソニル(fludioxonil)、フルフェノキシストロビン(flufenoxystrobin)、フルインダピル(fluindapyr)、フルメトベル(flumetover)、フルモルフ(flumorph)、フルオピコリド(fluopicolide)、フルオピモミド(fluopimomide)、フルオピラム(fluopyram)、フルオルイミド(fluoroimide)、フルオトリマゾール(fluotrimazole)、フルオキサピプロリン(fluoxapiprolin)、フルオキサストロビン(fluoxastrobin)、フルキンコナゾール(fluquinconazole)、フルシラゾール(flusilazole)、フルスルファミド(flusulfamide)、フルトラニル(flutolanil)、フルチアニル(flutianil)、フルトリアホール(flutriafol)、フルキサピロキサド(fluxapyroxad)、フォルペット(folpet)、ホセチル-アルミニウム(fosetyl-aluminium)、フサライド(fthalide)、フベリダゾール(fuberidazole)、フララキシル(furalaxyl)、フラメトピル(furametpyr)、フルカルバニル(furcarbanil)、フルコナゾール(furconazole)、フルコナゾール-シス(furconazole-cis)、フルメシクロックス(furmecyclox)、フロファネート(furophanate)、グリジン(glyodin)、グリセオフルビン(griseofulvin)、グアザチン(guazatine)、ハラクリネート(halacrinate)、ヘキサクロロベンゼン(hexachlorobenzene)、ヘキサコナゾール(hexaconazole)、ヘキシルチオフォス(hexylthiofos)、硫酸オキシキノリン(8-hydroxyquinoline sulfate)、ヒメキサゾール(hymexazol)、イマザリル(imazalil)、イミベンコナゾール(imibenconazole)、イミノクタジン-アルベシル酸塩(iminoctadine-albesilate)、イミノクタジン酢酸塩(iminoctadine-triacetate)、インピルフルキサム(inpyrfluxam)、イオドカルブ(iodocarb)、イプコナゾール(ipconazole)、イプフェントリフルコナゾール(ipfentrifluconazole)、イプフルフェノキン(ipflufenoquin)、イプロベンホス(iprobenfos)、イプロジオン(iprodione)、イプロバリカルブ(iprovalicarb)、イソフェタミド(isofetamid)、イソフルシプラム(isoflucypram)、イソチアニル(isotianil)、イソプロチオラン(isoprothiolane)、イソピラザム(isopyrazam)、イソバレジオン(isovaledione)、カスガマイシン(kasugamycin)、クレソキシム-メチル(kresoxim-methyl)、ラミナリン(laminarin)、マンカッパー(mancopper)、マンコゼブ(mancozeb)、マンデストロビン(mandestrobin)、マンジプロパミド(mandipropamid)、マンネブ(maneb)、メベニル(mebenil)、メカルビンジッド(mecarbinzid)、メフェントリフルコナゾール(mefentrifluconazole)、メパニピリム(mepanipyrim)、メプロニル(mepronil)、メプチルジノカップ(meptyldinocap)、メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M)、メタム(metam)、メタゾキソロン(metazoxolon)、メトコナゾール(metconazole)、メタスルホカルブ(methasulfocarb)、メトフロキサム(methfuroxam)、メチルテトラプロール(metyltetraprole)、メチラム(metiram)、メトミノストロビン(metominostrobin)、メトラフェノン(metrafenone)、メトスルフォバックス(metsulfovax)、ミルネブ(milneb)、ミクロブタニル(myclobutanil)、ミクロゾリン(myclozolin)、ナーバム(nabam)、ナフティフィン(naftifine)、ナタマイシン(natamycin)、有機ニッケル(nickel bis (dimethyldithiocarbamate))、ニトロスチレン(nitrostyrene)、ニトロタル-イソプロピル(nitrothal-isopropyl)、ヌアリモール(nuarimol)、オクチノリン(octhilinone)、オフレース(ofurace)、オリサストロビン(orysastrobin)、オキサジキシル(oxadixyl)、オキサチアピプロリン(oxathiapiprolin)、オキシキノリン銅(oxine copper)、オキスポコナゾールフマル酸塩(oxpoconazole fumarate)、オキシカルボキシン(oxycarboxin)、ペフラゾエート(pefurazoate)、ペンコナゾール(penconazole)、ペンシクロン(pencycuron)、ペンフルフェン(penflufen)、ペンタクロロフェノール(pentachlorophenol)、ペンチオピラド(penthiopyrad)、オルソフェニルフェノール(2-phenylphenol)、ホスダイフェン(phosdiphen)、フサライド(phthalide)、ピカルブトラゾクス(picarbutrazox)、ピコキシストロビン(picoxystrobin)、ピペラリン(piperalin)、ポリカーバメート(polycarbamate)、ポリオキシン(polyoxins)、ポリオキシン-D(polyoxorim)、ポタシウムアジド(potassium azide)、炭酸水素カリウム(potassium hydrogen carbonate)、プロベナゾール(probenazole)、プロクロラズ(prochloraz)、プロシミドン(procymidone)、プロパモカルブ塩酸塩(propamocarb hydrochloride)、プロピコナゾール(propiconazole)、プロピネブ(propineb)、プロキナジド(proquinazid)、プロチオカルブ(prothiocarb)、ピラゾホス(pyrazophos)、ピリベンカルブ(pyribencarb)、ピリフェノックス(pyrifenox)、ピリメタニル(pyrimethanil)、ピリミノストロビン(pyriminostrobin)、ピロキロン(pyroquilon)、
プロチオカルブ(prothiocarb)、プロチオコナゾール(prothioconazole)、ピジフルメトフェン(pydiflumetofen)、ピラカルボリド(pyracarbolid)、ピラクロストロビン(pyraclostrobin)、ピラメトストロビン(pyrametostrobin)、ピラオキシストロビン(pyraoxystrobin)、ピラプロポイン(pyrapropoyne)、ピラジフルミド(pyraziflumid)、ピリダクロメチル(pyridachlometyl)、ピリジニトリル(pyridinitril)、ピリオフェノン(pyriofenone)、ピリソキサゾール(pyrisoxazole)、ピロキシクロル(pyroxychlor)、ピロキシフル(pyroxyfur)、キナセトール-スルフェート(quinacetol-sulfate)、キナザミド(quinazamid)、キンコナゾール(quinconazole)、キノキシフェン(quinoxyfen)、キノフメリン(quinofumelin)、キントゼン(quintozene)、ラベンザゾール(rabenzazole)、サリチルアニリド(salicylanilide)、セダキサン(sedaxane)、シルチオファム(silthiofam)、シメコナゾール(simeconazole)、炭酸水素ナトリウム(sodium hydrogen carbonate)、次亜塩素酸ナトリウム(sodium hypochlorite)、スピロキサミン(spiroxamine)、硫黄(sulfur)、テブコナゾール(tebuconazole)、テブフロキン(tebufloquin)、テフロクタラム(tecloftalam)、テクナゼン(tecnazene)、テコラム(tecoram)、テトラコナゾール(tetraconazole)、チアベンダゾール(thiabendazole)、チアジフルオール(thiadifluor)、チシオフェン(thicyofen)、チフルザミド(thifluzamide)、チオクロルフェンヒム(thiochlorfenphim)、チオファネート(thiophanate)、チオファネート-メチル(thiophanate-methyl)、チウラム(thiram)、チアジニル(tiadinil)、チオキシミド(tioxymid)、トルクロホス-メチル(tolclofos-methyl)、トルプロカルブ(tolprocarb)、トリルフルアニド(tolylfluanid)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリアミホス(triamiphos)、トリアリモール(triarimol)、トリアズブチル(triazbutil)、トリアゾキシド(triazoxide)、トリブチル錫オキシド(tributyltin oxide)、トリクラミド(trichlamide)、トリクロピリカルブ(triclopyricarb)、トリシクラゾール(tricyclazole)、トリデモルフ(tridemorph)、トリフロキシストロビン(trifloxystrobin)、トリフルミゾール(triflumizole)、トリホリン(triforine)、トリチコナゾール(triticonazole)、バリダマイシン(validamycin)、バリフェナレート(valifenalate)、ビンクロゾリン(vinclozolin)、ザリラミド(zarilamid)、ジンクナフテネート(zinc naphthenate)、硫酸亜鉛(zinc sulfate)、ジネブ(zineb)、ジラム(ziram)、ゾキサミド(zoxamide)、シイタケ菌糸体抽出物(shiitake mycelium extract)及びシイタケ子実体抽出物(shiitake fruiting body extract)等。
殺虫剤:アバメクチン(abamectin)、アセフェート(acephate)、アセキノシル(acequinocyl)、アセタミプリド(acetamiprid)、アクリナトリン(acrinathrin)、アシノナピル(acynonapyr)、アフィドピロペン(afidopyropen)、アフォクソラネル(afoxolaner)、アラニカルブ(alanycarb)、アルジカルブ(aldicarb)、アレスリン(allethrin)、アルファ-シペルメトリン(alpha-cypermethrin)、アルファ-エンドスルファン(alpha-endosulfan)、アミドフルメット(amidoflumet)、アミトラズ(amitraz)、アザメチホス(azamethiphos)、アジンホス-エチル(azinphos-ethyl)、アジンホス-メチル(azinphos-methyl)、アゾシクロチン(azocyclotin)、バチルスチューリンゲンシス(bacillus thuringiensis)、ベンダイオカルブ(bendiocarb)、ベンフルトリン(benfluthrin)、ベンフラカルブ(benfuracarb)、ベンスルタップ(bensultap)、ベンゾキシメート(benzoximate)、ベンズピリモキサン(benzpyrimoxan)、ベータ-シフルトリン(beta-cyfluthrin)、ベータ-シペルメトリン(beta-cypermethrin)、ビフェナゼート(bifenazate)、ビフェントリン(bifenthrin)、ビオアレスリン(bioallethrin)、ビオレスメトリン(bioresmethrin)、ビストリフルロン(bistrifluron)、ブロフラニリド(broflanilide)、ブロモプロピレート(bromopropylate)、ブプロフェジン(buprofezin)、ブトカルボキシム(butocarboxim)、カルバリル(carbaryl)、カルボフラン(carbofuran)、カルボスルファン(carbosulfan)、カルタップ(cartap)、チノメチオネート(chinomethionat)、クロルアントラニリプロール(chlorantraniliprole)、クロルエトキシホス(chlorethxyfos)、クロルフェナピル(chlorfenapyr)、クロルフェンビンホス(chlorfenvinphos)、クロルフルアズロン(chlorfluazuron)、クロルメホス(chlormephos)、クロロベンジラート(chlorobezilate)、クロロプラレスリン(chloroprallethrin)、クロルピリホス(chlorpyrifos)、クロピリホス-メチル(chlorpyrifos-methyl)、クロマフェノジド(chromafenozide)、クロフェンテジン(clofentezine)、クロチアニジン(clothianidin)、シアノホス(cyanophos)、シアントラニリプロール(cyantraniliprole)、シクラニリプロール(cyclaniliprole)、シクロプロトリン(cycloprothrin)、シエノピラフェン(cyenopyrafen)、cyetpyrafen(cyetpyrafen)、シフルメトフェン(cyflumetofen)、シフルトリン(cyfluthrin)、シハロジアミド(cyhalodiamide)、シハロトリン(cyhalothrin)、サイヘキサチン(cyhexatine)、シペルメトリン(cypermethrin)、シフェノトリン(cyphenothrin)、cyproflanilide(cyproflanilide)、シロマジン(cyromazine)、デルタメトリン(deltamethrin)、ジアクロデン(diacloden)、ジアフェンチウロン(diafenthiuron)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos)、ジクロロメゾチアズ(dicloromezotiaz)、ジコホール(dicofol)、ジエノクロル(dienochlor)、ジフロビダジン(diflovidazin)、ジフルベンズロン(diflubenzuron)、ジメフルトリン(dimefluthrin)、ジメトエート(dimethoate)、ジメチルビンホス(dimethylvinphos)、ジンプロピリダズ(dimpropyridaz)、ジノテフラン(dinotefuran)、ジオフェノラン(diofenolan)、ジスルフォトン(disulfoton)、デーエヌオーシー(DNOC)、d-T-80-フタルスリン(d-tetramethrin)、エマメクチンベンゾエート(emamectin-benzoate)、エンペントリン(empenthrin)、エンドスルファン(endosulfan)、イーピーエヌ(EPN)、イプシロン-メトフルトリン(epsilon-metofluthrin)、イプシロン-モムフルオロトリン(epsilon-momfluorothrin)、エスフェンバレレート(esfenvalerate)、エチオフェンカルブ(ethiofencarb)、エチプロール(ethiprole)、エトフェンプロックス(etofenprox)、エトキサゾール(etoxazole)、エトリムホス(etrimfos)、フェバンテル(Febantel)、フェナザキン(fenazaquin)、フェンブタチンオキシド(fenbutatin oxide)、フェニトロチオン(fenitrothion)、フェンメゾジチアズ(fenmezoditiaz)、フェノブカルブ(fenobucarb)、フェノチオカルブ(fenothiocarb)、フェノキシカルブ(fenoxycarb)、フェンプロパトリン(fenpropathrin)、フェンピロキシメート(fenpyroximate)、フェンチオン(fenthion)、フェンバレレート(fenvalerate)、フィプロニル(fipronil)、フロメトキン(flometoquin)、フロニカミド(flonicamid)、フルアクリピリム(fluacrypyrim)、フルアズロン(fluazuron)、フルベンジアミド(flubendiamide)、fluchlordiniliprole(fluchlorodiniliprole)、フルシクロクスロン(flucycloxuron)、フルシトリネート(flucythrinate)、フルフェネリム(flufenerim)、フルフェノクスロン(flufenoxuron)、フルフェンプロックス(flufenprox)、フルフィプロール(flufiprole)、フルヘキサホン(fluhexafon)、フルメトリン(flumethrin)、フルペンチオフェノックス(flupentiofenox)、フルピラジフロン(flupyradifurone)、フルピリミン(flupyrimin)、フルララネル(fluralaner)、フルバリネート(fluvalinate)、フルキサメタミド(fluxametamide)、ホノホス(fonophos)、ホルメタネート(formetanate)、フォルモチオン(formothion)、フラチオカルブ(furathiocarb)、ガンマ-シハロトリン(gamma-cyhalothrin)、ハルフェンプロックス(halfenprox)、ハロフェノジド(halofenozide)、ヘプタフルトリン(heptafluthrin)、ヘキサフルムロン(hexaflumuron)、ヘキシチアゾクス(hexythiazox)、ヒドラメチルノン(hydramethylnon)、イミダクロプリド(imidacloprid)、イミプロトリン(imiprothrin)、indazapyroxamet(indazapyroxamet)、インドキサカルブ(indoxacarb)、インドキサカルブ-MP(indoxacarb-MP)、イソシクロセラム(isocycloseram)、イソフェンホス(isofenphos)、イソプロカルブ(isoprocarb)、イソキサチオン(isoxathion)、カッパ-ビフェントリン(kappa-bifenthrin)、カッパ-テフルトリン(kappa-tefluthrin)、ラムダ-シハロトリン(lambda-cyhalothrin)、レピメクチン(lepimectin)、ルフェヌロン(lufenuron)、マラチオン(malathion)、メペルフルスリン(meperfluthrin)、メタフルミゾン(metaflumizone)、メタルカルブ(metalcarb)、メタルデヒド(metaldehyde)、メタクリホス(methacrifos)、メタミドホス(methamidophos)、メチダチオン(methidathion)、メソミル(methomyl)、メソプレン(methoprene)、メトキシクロル(methoxychlor)、メトキシフェノジド(methoxyfenozide)、臭化メチル(methyl bromide)、メトフルトリン(metofluthrin)、ミルベメクチン(milbemectin)、モムフルオロトリン(momfluorothrin)、モノクロトホス(monocrotophos)、ムスカルア(muscalure)、nicofluprole(nicofluprole)、ニテンピラム(nitenpyram)、ノバルロン(novaluron)、ノビフルムロン(noviflumuron)、オメトエート(omethoate)、オキサゾスルフィル(oxazosulfyl)、オキシデメトン-メチル(oxydemeton-methyl)、オキシデプロホス(oxydeprofos)、パラチオン(parathion)、パラチオン-メチル(parathion-methyl)、ペンタクロロフェノール(pentachlorophenol)、ペルメトリン(permethrin)、フェノトリン(phenothrin)、フェントエート(phenthoate)、ホレート(phorate)、ホサロン(phosalone)、ホスメット(phosmet)、ホスファミドン(phosphamidon)、ホキシム(phoxim)、ピリミカーブ(pirimicarb)、ピリミホス-メチル(pirimiphos-methyl)、プラジクアンテル(Praziquantel)、プロフェノホス(profenofos)、プロフルトリン(profluthrin)、プロパホス(propaphos)、プロパルギット(propargite)、プロチオホス(prothiofos)、プロトリフェンブト(protrifenbute)、ピフルブミド(pyflubumide)、ピメトロジン(pymetrozine)、ピラクロホス(pyraclofos)、ピラフルプロール(pyrafluprole)、ピレトリン(pyrethrins)、ピリダベン(pyridaben)、ピリダリル(pyridalyl)、ピリフルキナゾン(pyrifluquinazon)、ピリミジフェン(pyrimidifen)、ピリプロール(pyriprole)、ピリプロキシフェン(pyriproxyfen)、レスメトリン(resmethrin)、ロテノン(rotenone)、シラフルオフェン(silafluofen)、spidoxamat(spidoxamat)、スピネトラム(spinetoram)、スピノサド(spinosad)、スピロジクロフェン(spirodiclofen)、スピロメシフェン(spiromesifen)、スピロピジオン(spiropidion)、スピロテトラマート(spirotetramat)、スピロメシフェン(spyromesifen)、スルホテップ(sulfotep)、スルホキサフロル(sulfoxaflor)、スルプロホス(sulprofos)、タウ-フルバリネート(tau-fluvalinate)、テブフェノジド(tebfenozide)、テブフェンピラド(tebufenpyrad)、テフルベンズロン(teflubenzuron)、テフルトリン(tefluthorin)、テルブホス(terbufos)、テトラクロラントラニリプロール(tetrachlorantraniliprole)、テトラクロロビンホス(tetrachlorvinphos)、テトラメトリン(tetramethrin)、テトラメチルフルスリン(tetramethylfluthrin)、テトラニリプロール(tetraniliprole)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、チオシクラム(thiocyclam)、チオジカルブ(thiodicarb)、チオファノックス(thiofanox)、チオメトン(thiometon)、トルフェンピラド(tolfenpyrad)、トラロメトリン(tralomethrin)、トランスフルトリン(transfluthrin)、トリアザメート(triazamate)、トリアズロン(triazuron)、トリクロルホン(trichlorfon)、トリフルメゾピリム(triflumezopyrim)、トリフルムロン(triflumuron)、チクロピラゾフロル(tyclopyrazoflor)、バミドチオン(vamidothion)及びゼタ-シペルメトリン(zeta-cypermethrin)等。
寄生虫薬:エスフェンバレレート(esfenvalerate)、フェンプロパトリン(fenpropathrin)、フェンバレレート(fenvalerate)、アルファシペルメトリン(cypermethrin)、ビフェントリン(bifenthrin)、シペルメトリン(cypermethrin)、デルタメトリン(deltamethrin)、エトフェンプロックス(etofenprox)、ラムダシハロトリン(lambda-cyhalothrin)、ペルメトリン(permethrin)、テフルトリン(tefluthrin)、ゼータシペルメトリン(zeta-cypermethrin)、アセタミプリド(acetamiprid)、クロチアニジン(clothianidin)、ジノテフラン(dinotefuran)、イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、チアメトキサム(thiamethoxam)、クロマフェノジド(chromafenozide)、フェノキシカルブ(fenoxycarb)、ルフェヌロン(lufenuron)、メトプレン(methoprene)、ピリプロキシフェン(pyriproxyfen)、トリフルムロン(triflumuron)、クロルピリホス(chlorpyrifos)、クロルピリホスメチル(chlorpyrifos-methyl)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos)、フェニトロチオン(fenitrothion)、フェンチオン(fenthion)、マラチオン(malathion)、ピリミホスメチル(pirimiphos-methyl)、テトラクロロビンホス(tetrachlorvinphos)、エチプロール(ethiprole)、フィプロニル(fipronil)、プロポキスル(propoxur)、カルバリル(carbaryl)、ベンジオカルブ(bendiocarb)、メトキサジアゾン(metoxadiazone)、フェノカルブ(fenobucarb)、カルボフラン(carbofuran)、アフォキソラネル(afoxolaner)、フルララネル(fluralaner)、フルキサメタミド(fluxametamide)、サロラネル(sarolaner)、ロティラネル(lotilaner)、チゴラネル(tigolaner)、esafoxolaner(esafoxolaner)、modoflaner(modoflaner)、umifoxolaner(umifoxolaner)、mivorilaner(mivorilaner)、アベルメクチン(avermectin)、イベルメクチン(ivermectin)、ドラメクチン(doramectin)、エプリノメクチン(eprinomectin)、マデユラマイシン(maduramycin)、ミルベマイシン(milbemycin)、ミルベマイシンオキシム(milbemycin oxime)、モキシデクチン(moxidectin)、セラメクチン(selamectin)、インドキサカルブ(indoxacarb)、アミトラズ(amitraz)、ビストリフルロン(bistrifluron)、スピノサド(spinosad)、アルベンダゾール(albendazole)、アトバコン(atovaquone)、ビチオノール(bithionol)、カンベンダゾール(cambendazole)、カルニダゾール(carnidazole)、クロロキン(chloroquine)、クラズリル(clazuril)、クロルスロン(clorsulon)、クロサンテル(closantel)、クマホス(coumaphos)、ジクロロフェン(dichlorophen)、ジエチルカルバマジン(diethylcarbamazine)、ジミナゼン(diminazene)、ジニトルミド(dinitolmide)、ヨウ化ジチアザニン(dithiazanine iodide)、エモデプシド(emodepside)、エプシプランテル(epsiprantel)、フェバンテル(febantel)、フェンベンダゾール(fenbendazole)、フルベンダゾール(flubendazole)、グリカルピラミド(glycalpyramide)、イミドカルブ(imidocarb)、レバミゾール(levamisole)、メベンダゾール(mebendazole)、メベンダゾール(mebendazole)、メフロキン塩酸塩(mefloquine hydrochloride)、メラルソミン二塩酸塩(melarsamine hydrochloride)、メトロニダゾール(metronidazole)、メチリジン(metyridine)、モネパンテル(monepantel)、酒石酸モランテル(morantel tartrate)、ニクロサミド(niclosamide)、パモ酸オキサンテル(oxantel pamoate)、酒石酸オキサンテル(oxantel tartrate)、オキシベンダゾール(oxibendazole)、オキシクロザニド(oxyclozanide)、アジピン酸ピペラジン(piperazine adipate)、クエン酸ピペラジン(piperazine citrate)、リン酸ピペラジン(piperazine phosphate)、プラジカンテル(praziquantel)、パモ酸ピランテル(pyrantel pamoate)、ラフォキサニド(rafoxanide)、テトラミソール塩酸塩(tetramisole hydrochloride)、チアベンダゾール(thiabendazole)及びトリクラベンダゾール(triclabendazole)等。
抗真菌剤:ケトコナゾール(ketoconazole)及びミコナゾール硝酸塩(miconazole nitrate)など。
抗菌剤:アモキシシリン(amoxicillin)、アンピシリン(ampicillin)、ベトキサジン(bethoxazin)、ビチオノール(bithionol)、ブロノポール(bronopol)、セファピリン(cefapirin)、セファゾリン(cefazolin)、セフキノム(cefquinome)、セフチオフル(ceftiofur)、クロルテトラサイクリン(chlortetracycline)、クラブラン酸(clavulanic acid)、ダノフロキサシン(danofloxacin)、ジフロキサシン(difloxacin)、ジニトルミド(dinitolmide)、エンロフロキサシン(enrofloxacin)、フロルフェニコール(florfenicol)、リンコマイシン(lincomycin)、ロメフロキサシン(lomefloxacin)、マルボフロキサシン(marbofloxacin)、ミロキサシン(miloxacin)、ミロサマイシン(mirosamycin)、ニトラピリン(nitrapyrin)、ノルフロキサシン(norfloxacin)、オクチリノン(octhilinone)、オフロキサシン(ofloxacin)、オルビフロキサシン(orbifloxacin)、オキソリニック酸(oxolinic acid)、オキシテトラサイクリン(oxytetracycline)、ペニシリン(penicillin)、ストレプトマイシン(streptomycin)、チアンフェニコール(thiamphenicol)、フマル酸チアムリン(tiamulin fumarate)、リン酸チルミコシン(tilmicosin phosphate)、酢酸イソ吉草酸タイロシン(acetylisovaleryltylosin)、リン酸タイロシン(tylosin phosphate)、ツラスロマイシン(tulathromycin)、バルネムリン(valnemulin)、貝殻焼成カルシウム(酸化カルシウム)、タラロマイセス属菌、トリコデルマ属菌及びユニオチリウム属菌など。 In one aspect, the types of pesticides used in combination with the compound of the present invention include, for example, the compounds described in The Pesticide Manual, 18th Edition, 2018. Specific examples of common names are as follows. However, pesticides used in combination are not necessarily limited to these.
Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (benalaxyl-M), benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, bordeaux mixture, boscalid, bromconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph ( carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture, chinomethionat, clobenzazone hiazone), chloraniformmethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, clozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate, coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil ), cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid, dichlobentiazox, dichlofluanid, dichlone ), dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine, dicloran, diethofe diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton ), dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbone, diphenylamine, dipymetitrone , dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone (famoxadone), fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph ( fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, fluconazole, fluconazole-furconazole -cis), furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexyl Thiophos (hexylthiofos), 8-hydroxyquinoline sulfate, hymexazol, imaza imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isofrucypram, isotianil, isoprothiolane ( isoprothiolane, isopyrazam, isovaledione, kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl ( metalaxyl), metalaxyl-M, metam, metazoxolon, metconazole, metasulfocarb, methfuroxam, methyltetraprole, metiram , metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil il), myclozolin, nabam, naftifine, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol (nuarimol), octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxine copper, oxpoconazole fumarate fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol , phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, Potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb , proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox (p yrifenox), pyrimethanil, pyriminostrobin, pyroquilon,
prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne ), pyraziflumid, pyridaclomethyl, pyridinitril, pyriofenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamide ( quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, sedaxane, silthiofam, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecorum (tecoram), tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl ( thiophanate-methyl), thiram, tiadini l), tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol ( triarimol, triazbutil, triazoxide, tributyltin oxide, trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin , triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract and shiitake fruiting body extract and the like.
Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb ( aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethifos, azinphos-ethyl ), azinphos-methyl, azocyclotin, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate ( benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin , bistrifluron, broflanilide, bromopropylate, buprofezin, butocarbboxim, carbaryl, carbofuran, carbosulfan, cartap (cartap), chinomethionat, chlorantraniliprole, chlorethoxyfos, chlorfe napyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos -methyl), chromafenozide, clofentezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide , cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dichloromezotiaz, dicofol, dienochlor ), diflovidazin, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, day DNOC, dT-80-phthalthuri d-tetramethrin, emamectin-benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, febantel, fenazaquin, fenbutatin oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvale fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubendiamide, fluchlordiniliprole (fluchlorodiniliprole), flucycloxuron, flu citrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyrimin, fluralaner laner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb ( indoxacarb, indoxacarb-MP, isocycloseram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin -tefluthrin), lambda-cyhalothrin, lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalcarb, metaldehyde, methacrifos ( methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, metofluthrin, milbemectin , momfluorothrin, monocrotophos, muscar muscalure, nicofluprole, nitenpyram, novaluron, noviflumuron, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos (oxydeprofos), parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, forate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-methyl, praziquantel, profenofos, profluthrin, propaphos, propargite (propargite), prothiofos, protrifenbute, pyflubumide, pymetrozine, pyraclofos, pyrafluprole, pyrethrins, pyridaben, pyridalyl pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfen, resmethrin, rotenone, silafluofen, spidoxamat, spinetoram , spinosad, spirodiclofen, spiromesifen, spiropidion ion), spirotetramat, spyromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebfenozide, tebufenpyrad ), teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion and zeta-cypermethrin -cypermethrin), etc.
Parasiticides: esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox ( etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid ), nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos, ethiprole ( ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenobucarb, carbofuran, afoxolaner, fluralaner, fluxametamide ( fluxametamide), sarolaner, lotilaner, tigora tigolaner, esafoxolaner, modoflaner (modoflaner), umifoxolaner (umifoxolaner), mivorilaner (mivorilaner), avermectin, ivermectin, doramectin, eprinomectin, maduramycin, milbemycin, milbemycin oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole ), atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide, emodepside, epsiprantel, febantel, fenbendazole , flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride , metronidazole , methyridine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, Thiabendazole and triclabendazole and the like.
Antifungal agents: such as ketoconazole and miconazole nitrate.
Antibiotics: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline chlortetracycline, clavulanic acid, danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin ( lomefloxacin, marbofloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinics oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, tylosin acetate isovalerate (acetylisovaleryltylosin), tylosin phosphate, tulathromycin, valnemulin, calcined shell calcium (calcium oxide), Talaromyces spp., Trichoderma spp. and Uniothylium spp.
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、一般的には、有効成分量としてヘクタール(ha)当たり0.005~50kg程度が適当であり、0.01~1kgが好ましい。
The amount of the compound of the present invention to be applied varies depending on the application scene, application time, application method, cultivated crops, etc., but in general, the appropriate amount of active ingredient is about 0.005 to 50 kg per hectare (ha). Yes, preferably 0.01 to 1 kg.
次に、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, examples of formulations when using the compound of the present invention are shown. However, the compounding examples of the present invention are not limited to these. In addition, "parts" in the following formulation examples means parts by weight.
〔水和剤〕
本発明化合物 0.1~80部
固体担体 5~98.9部
界面活性剤 1~10部
その他 0~ 5部
その他として、例えば、固結防止剤、分解防止剤等が挙げられる。 [Wettable powder]
Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, an anti-caking agent and an anti-degradation agent.
本発明化合物 0.1~80部
固体担体 5~98.9部
界面活性剤 1~10部
その他 0~ 5部
その他として、例えば、固結防止剤、分解防止剤等が挙げられる。 [Wettable powder]
Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, an anti-caking agent and an anti-degradation agent.
〔乳剤〕
本発明化合物 0.1~30部
液体担体 45~95部
界面活性剤 4.9~15部
その他 0~10部
その他として、例えば、展着剤、分解防止剤等が挙げられる。 〔emulsion〕
Compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts Others include, for example, spreading agents and antidegradants.
本発明化合物 0.1~30部
液体担体 45~95部
界面活性剤 4.9~15部
その他 0~10部
その他として、例えば、展着剤、分解防止剤等が挙げられる。 〔emulsion〕
Compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts Others include, for example, spreading agents and antidegradants.
〔懸濁剤〕
本発明化合物 0.1~70部
液体担体 15~98.89部
界面活性剤 1~12部
その他 0.01~30部
その他として、例えば、凍結防止剤、増粘剤等が挙げられる。 [Suspension agent]
Compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts Others include, for example, antifreeze agents, thickeners and the like.
本発明化合物 0.1~70部
液体担体 15~98.89部
界面活性剤 1~12部
その他 0.01~30部
その他として、例えば、凍結防止剤、増粘剤等が挙げられる。 [Suspension agent]
Compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts Others include, for example, antifreeze agents, thickeners and the like.
〔顆粒水和剤〕
本発明化合物 0.1~90部
固体担体 0~98.9部
界面活性剤 1~20部
その他 0~10部
その他として、例えば、結合剤、分解防止剤等が挙げられる。 [Granular wettable powder]
Compound of the present invention 0.1-90 parts Solid carrier 0-98.9 parts Surfactant 1-20 parts Others 0-10 parts Others include, for example, binders and antidegradants.
本発明化合物 0.1~90部
固体担体 0~98.9部
界面活性剤 1~20部
その他 0~10部
その他として、例えば、結合剤、分解防止剤等が挙げられる。 [Granular wettable powder]
Compound of the present invention 0.1-90 parts Solid carrier 0-98.9 parts Surfactant 1-20 parts Others 0-10 parts Others include, for example, binders and antidegradants.
〔液剤〕
本発明化合物 0.01~70部
液体担体 20~99.99部
その他 0~ 10部
その他として、例えば、凍結防止剤、展着剤等が挙げられる。 [Liquid]
Compound of the present invention 0.01-70 parts Liquid carrier 20-99.99 parts Others 0-10 parts Others include, for example, antifreeze agents, spreading agents and the like.
本発明化合物 0.01~70部
液体担体 20~99.99部
その他 0~ 10部
その他として、例えば、凍結防止剤、展着剤等が挙げられる。 [Liquid]
Compound of the present invention 0.01-70 parts Liquid carrier 20-99.99 parts Others 0-10 parts Others include, for example, antifreeze agents, spreading agents and the like.
〔粒剤〕
本発明化合物 0.01~80部
固体担体 10~99.99部
その他 0~10部
その他として、例えば、結合剤、分解防止剤等が挙げられる。 [granules]
Compound of the present invention 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts Others include, for example, binders and antidegradants.
本発明化合物 0.01~80部
固体担体 10~99.99部
その他 0~10部
その他として、例えば、結合剤、分解防止剤等が挙げられる。 [granules]
Compound of the present invention 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts Others include, for example, binders and antidegradants.
〔粉剤〕
本発明化合物 0.01~30部
固体担体 65~99.99部
その他 0~5部
その他として、例えばドリフト防止剤、分解防止剤等が挙げられる。 [Powder]
Compound of the present invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-5 parts Others include, for example, anti-drift agents and anti-decomposition agents.
本発明化合物 0.01~30部
固体担体 65~99.99部
その他 0~5部
その他として、例えばドリフト防止剤、分解防止剤等が挙げられる。 [Powder]
Compound of the present invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-5 parts Others include, for example, anti-drift agents and anti-decomposition agents.
使用に際しては、上記製剤を水で1~10000倍、好ましくは100~10000倍に希釈して、又は希釈せずに散布する。
In use, the above formulation is diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, or sprayed without dilution.
次に、本発明化合物を有効成分とする農園芸用殺菌剤の製剤例を具体的に示すが、本発明化合物も含めて、これらのみに限定されるものではない。なお、以下の製剤例において「部」は重量部を意味する。
Next, specific formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient will be shown, but the compound of the present invention is not limited to these examples. In addition, "part" means a weight part in the following formulation examples.
〔製剤例1〕乳剤
本発明化合物No.1-001 20部
メチルナフタレン 55部
シクロヘキサノン 20部
ソルポール2680 5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:東邦化学工業社製、商品名)
上記成分を均一に混合して乳剤とする。使用に際しては、上記乳剤を水により50~20000倍に希釈して、有効成分量がヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 1] Emulsion Compound No. of the present invention. 1-001 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
The above ingredients are uniformly mixed to form an emulsion. In use, the emulsion is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.
本発明化合物No.1-001 20部
メチルナフタレン 55部
シクロヘキサノン 20部
ソルポール2680 5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:東邦化学工業社製、商品名)
上記成分を均一に混合して乳剤とする。使用に際しては、上記乳剤を水により50~20000倍に希釈して、有効成分量がヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 1] Emulsion Compound No. of the present invention. 1-001 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
The above ingredients are uniformly mixed to form an emulsion. In use, the emulsion is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.
〔製剤例2〕水和剤
本発明化合物No.1-001 25部
パイロフィライト 66部
ソルポール5039 4部
(アニオン性界面活性剤:東邦化学工業社製、商品名)
カープレックス#80D 3部
(ホワイトカーボン:塩野義製薬社製、商品名)
リグニンスルホン酸カルシウム 2部
上記成分を均一に混合粉砕して水和剤とする。使用に際しては、上記水和剤を水により50~20000倍に希釈して、有効成分量がヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 2] Wettable Powder Compound No. of the present invention. 1-001 25 parts Pyrophyllite 66 parts Solpol 5039 4 parts (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
Carplex #80D 3 copies (white carbon: manufactured by Shionogi & Co., Ltd., trade name)
Calcium lignosulfonate 2 parts The above ingredients are uniformly mixed and pulverized to prepare a wettable powder. In use, the wettable powder is diluted 50 to 20,000 times with water and sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
本発明化合物No.1-001 25部
パイロフィライト 66部
ソルポール5039 4部
(アニオン性界面活性剤:東邦化学工業社製、商品名)
カープレックス#80D 3部
(ホワイトカーボン:塩野義製薬社製、商品名)
リグニンスルホン酸カルシウム 2部
上記成分を均一に混合粉砕して水和剤とする。使用に際しては、上記水和剤を水により50~20000倍に希釈して、有効成分量がヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 2] Wettable Powder Compound No. of the present invention. 1-001 25 parts Pyrophyllite 66 parts Solpol 5039 4 parts (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
Carplex #80D 3 copies (white carbon: manufactured by Shionogi & Co., Ltd., trade name)
Calcium lignosulfonate 2 parts The above ingredients are uniformly mixed and pulverized to prepare a wettable powder. In use, the wettable powder is diluted 50 to 20,000 times with water and sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
〔製剤例3〕粉剤
本発明化合物No.1-001 3部
カープレックス#80D 0.5部
(ホワイトカーボン:塩野義製薬社製、商品名)
カオリナイト 95部
リン酸ジイソプロピル 1.5部
上記成分を均一に混合粉砕して粉剤とする。使用に際しては、上記粉剤の有効成分量が、ヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 3] Powder Compound No. of the present invention. 1-001 3 parts Carplex #80D 0.5 parts (white carbon: manufactured by Shionogi & Co., Ltd., trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to form powders. In use, the powder is sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
本発明化合物No.1-001 3部
カープレックス#80D 0.5部
(ホワイトカーボン:塩野義製薬社製、商品名)
カオリナイト 95部
リン酸ジイソプロピル 1.5部
上記成分を均一に混合粉砕して粉剤とする。使用に際しては、上記粉剤の有効成分量が、ヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 3] Powder Compound No. of the present invention. 1-001 3 parts Carplex #80D 0.5 parts (white carbon: manufactured by Shionogi & Co., Ltd., trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to form powders. In use, the powder is sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
〔製剤例4〕粒剤
本発明化合物No.1-001 5部
ベントナイト 30部
タルク 64部
リグニンスルホン酸カルシウム 1部
上記成分を均一に混合粉砕して、少量の水を加えて撹拌混合し、押出式造粒機で造粒し、乾燥して粒剤とする。使用に際しては、上記粒剤の有効成分量が、ヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 4] Granules Compound No. of the present invention. 1-001 5 parts Bentonite 30 parts Talc 64 parts Calcium lignosulfonate 1 part Uniformly mix and pulverize the above ingredients, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry. Make granules. In use, the granules are sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
本発明化合物No.1-001 5部
ベントナイト 30部
タルク 64部
リグニンスルホン酸カルシウム 1部
上記成分を均一に混合粉砕して、少量の水を加えて撹拌混合し、押出式造粒機で造粒し、乾燥して粒剤とする。使用に際しては、上記粒剤の有効成分量が、ヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 4] Granules Compound No. of the present invention. 1-001 5 parts Bentonite 30 parts Talc 64 parts Calcium lignosulfonate 1 part Uniformly mix and pulverize the above ingredients, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry. Make granules. In use, the granules are sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
〔製剤例5〕懸濁剤
本発明化合物No.1-001 25部
ソルポール3353 5部
(非イオン性界面活性剤:東邦化学工業社製、商品名)
ルノックス1000C 0.5部
(陰イオン界面活性剤:東邦化学工業社製、商品名)
ザンサンガム(天然高分子) 0.2部
安息香酸ソーダ 0.4部
プロピレングリコール 10部
水 58.9部
有効成分(本発明化合物)を除く上記の成分を均一に溶解し、次いで、本発明化合物を加えてよく撹拌した後、サンドミルにて湿式粉砕してフロアブル剤を得る。使用に際しては、前記フロアブル剤を水により50~20000倍に希釈して、有効成分量がヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 5] Suspending agent Compound No. of the present invention. 1-001 25 parts Solpol 3353 5 parts (Nonionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
Lunox 1000C 0.5 parts (anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts Dissolve the above components excluding the active ingredient (the compound of the present invention) uniformly, then add the compound of the present invention. After adding and stirring well, the mixture is wet pulverized with a sand mill to obtain a flowable agent. In use, the above flowable agent is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.
本発明化合物No.1-001 25部
ソルポール3353 5部
(非イオン性界面活性剤:東邦化学工業社製、商品名)
ルノックス1000C 0.5部
(陰イオン界面活性剤:東邦化学工業社製、商品名)
ザンサンガム(天然高分子) 0.2部
安息香酸ソーダ 0.4部
プロピレングリコール 10部
水 58.9部
有効成分(本発明化合物)を除く上記の成分を均一に溶解し、次いで、本発明化合物を加えてよく撹拌した後、サンドミルにて湿式粉砕してフロアブル剤を得る。使用に際しては、前記フロアブル剤を水により50~20000倍に希釈して、有効成分量がヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 5] Suspending agent Compound No. of the present invention. 1-001 25 parts Solpol 3353 5 parts (Nonionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
Lunox 1000C 0.5 parts (anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name)
Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts Dissolve the above components excluding the active ingredient (the compound of the present invention) uniformly, then add the compound of the present invention. After adding and stirring well, the mixture is wet pulverized with a sand mill to obtain a flowable agent. In use, the above flowable agent is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.
〔製剤例6〕粒状水和剤
本発明化合物No.1-001 75部
ハイテノールNE-15 5部
(アニオン性界面活性剤:第一工業製薬社製、商品名)
バニレックスN 10部
(アニオン性界面活性剤:日本製紙社製、商品名)
カープレックス#80D 10部
(ホワイトカーボン:塩野義製薬社製、商品名)
上記成分を均一に混合微粉砕して、少量の水を加えて撹拌混合し、押出式造粒機で造粒し、乾燥してドライフロアブル剤とする。使用に際しては、水で50~20000倍に希釈して、有効成分が1ヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 6] Granular Wettable Powder Compound No. of the present invention. 1-001 75 parts Hytenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd., trade name)
Vanilex N 10 parts (anionic surfactant: manufactured by Nippon Paper Industries, trade name)
Carplex #80D 10 parts (white carbon: manufactured by Shionogi & Co., Ltd., trade name)
The above ingredients are uniformly mixed and pulverized, a small amount of water is added, the mixture is stirred and mixed, granulated with an extrusion granulator, and dried to obtain a dry flowable agent. When used, it is diluted 50 to 20,000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare.
本発明化合物No.1-001 75部
ハイテノールNE-15 5部
(アニオン性界面活性剤:第一工業製薬社製、商品名)
バニレックスN 10部
(アニオン性界面活性剤:日本製紙社製、商品名)
カープレックス#80D 10部
(ホワイトカーボン:塩野義製薬社製、商品名)
上記成分を均一に混合微粉砕して、少量の水を加えて撹拌混合し、押出式造粒機で造粒し、乾燥してドライフロアブル剤とする。使用に際しては、水で50~20000倍に希釈して、有効成分が1ヘクタール当たり0.005~50kgになるように散布する。 [Formulation Example 6] Granular Wettable Powder Compound No. of the present invention. 1-001 75 parts Hytenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd., trade name)
Vanilex N 10 parts (anionic surfactant: manufactured by Nippon Paper Industries, trade name)
Carplex #80D 10 parts (white carbon: manufactured by Shionogi & Co., Ltd., trade name)
The above ingredients are uniformly mixed and pulverized, a small amount of water is added, the mixture is stirred and mixed, granulated with an extrusion granulator, and dried to obtain a dry flowable agent. When used, it is diluted 50 to 20,000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare.
本発明化合物の施用方法としては、茎葉散布、土壌処理、種子消毒等が挙げられるが、通常当業者が利用する一般的な方法においても有効である。
The application method of the compound of the present invention includes foliage spraying, soil treatment, seed disinfection, etc., but general methods usually used by those skilled in the art are also effective.
〔まとめ〕
以上の通り、本発明は下記〔1〕~〔7〕に関するものである。 〔summary〕
As described above, the present invention relates to the following [1] to [7].
以上の通り、本発明は下記〔1〕~〔7〕に関するものである。 〔summary〕
As described above, the present invention relates to the following [1] to [7].
[式中、R1は、水素原子又は1~C6アルキルを表し、
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-C(O)R9、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
G-1~G-65は、それぞれ下記の構造式で表される構造を表し、
[In the formula, R 1 represents a hydrogen atom or 1 to C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 cycloalkoxycarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65; represent,
G-1 to G-65 each represent a structure represented by the following structural formula,
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-C(O)R9、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
G-1~G-65は、それぞれ下記の構造式で表される構造を表し、
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 cycloalkoxycarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65; represent,
G-1 to G-65 each represent a structure represented by the following structural formula,
R3は、フェニル、(Z)m1によって置換されたフェニル、F-31又はF-34を表し、
F-31及びF-34は、下記の構造式で表される構造を表し、 R 3 represents phenyl, phenyl substituted by (Z) m1 , F-31 or F-34;
F-31 and F-34 represent structures represented by the following structural formulas,
F-31及びF-34は、下記の構造式で表される構造を表し、 R 3 represents phenyl, phenyl substituted by (Z) m1 , F-31 or F-34;
F-31 and F-34 represent structures represented by the following structural formulas,
L-1~L-6、L-8及びL-9は、下記の構造式で表される構造を表し、
L-1 to L-6, L-8 and L-9 represent structures represented by the following structural formulas,
R5は、C1~C6アルキルを表し、
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル又はE-1~E-90、L-5、L-6、L-8又はL-9を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
E-1~E-90は、それぞれ下記の構造式で表される構造を表し、
R 5 represents C 1 -C 6 alkyl,
R b represents a hydrogen atom,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to representing E-90, L-5, L-6, L-8 or L-9,
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
E-1 to E-90 each represent a structure represented by the following structural formula,
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル又はE-1~E-90、L-5、L-6、L-8又はL-9を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
E-1~E-90は、それぞれ下記の構造式で表される構造を表し、
R b represents a hydrogen atom,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to representing E-90, L-5, L-6, L-8 or L-9,
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
E-1 to E-90 each represent a structure represented by the following structural formula,
R8は、C1~C6アルコキシ、C3~C6シクロアルキル、-C(=NOR17)R18、-C(=NNR13R14)Ra1、-C(=NCN)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、C1~C6アルキルアミノ、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65、E-1~E-89又はE-90を表し、
R10は、フェニルを表し、
R11は、-OH、C1~C6アルコキシ、C1~C6アルキルアミノカルボニル、-C(O)N(ORa)Ra2、E-3、E-6、E-7又はE-38を表し、
R12は、水素原子又はC1~C6アルキルを表し、
R13は、水素原子又はC1~C6アルキルを表し、
R14は、C1~C6アルキル又はC1~C6アルキルカルボニルを表し、
R15は、シアノ、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルキル、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R17は、水素原子、C1~C6アルキル又は-CH2C(O)Raを表し、
R18は、水素原子、C1~C6アルキル又はフェニルを表し、
Raは、C1~C6アルキルを表し、
Ra1は、水素原子、C1~C6アルキル、フェニル又は(Z1)mによって置換されたフェニルを表し、
Ra2は、C1~C6アルキルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、又は互いに相異なっても良く、
Z1は、シアノ、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、又は互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、シアノ、C1~C6アルキル、C1~C6アルコキシ、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-CH2CN又は-C(O)C(O)ORaを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を表し、p5が2、3、4又は5の整数を表し、p7が2、3、4、5、6又は7の整数を表す場合には、各々のZ9は互いに同一であっても、又は互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、又は互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表されるチエノウラシル化合物又はその塩。 R 8 is C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, —C(=NOR 17 )R 18 , —C(=NNR 13 R 14 )R a1 , —C(=NCN)R a1 , represents phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkyl amino, di(C 1 -C 6 alkyl)amino, —C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65, E-1 to E- 89 or E-90,
R 10 represents phenyl,
R 11 is —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylaminocarbonyl, —C(O)N(OR a )R a2 , E-3, E-6, E-7 or E- represents 38,
R 12 represents a hydrogen atom or C 1 -C 6 alkyl,
R 13 represents a hydrogen atom or C 1 -C 6 alkyl,
R 14 represents C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl,
R 15 represents cyano, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 17 represents a hydrogen atom, C 1 -C 6 alkyl or —CH 2 C(O)R a ,
R 18 represents a hydrogen atom, C 1 -C 6 alkyl or phenyl;
R a represents C 1 -C 6 alkyl,
R a1 represents a hydrogen atom, C 1 -C 6 alkyl, phenyl or phenyl substituted by (Z 1 ) m ;
R a2 represents C 1 -C 6 alkyl,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents cyano, a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a is cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 6 alkyl)aminocarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —CH CN or —C ( O)C(O)OR a ,
In relation to Z9, p2 represents an integer of 2, p3 represents an integer of 2 or 3, p4 represents an integer of 2, 3 or 4, and p5 represents an integer of 2, 3, 4 or 5. and when p represents an integer of 2, 3, 4, 5, 6 or 7, each Z 9 may be the same as or different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
A thienouracil compound represented by or a salt thereof.
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、C1~C6アルキルアミノ、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65、E-1~E-89又はE-90を表し、
R10は、フェニルを表し、
R11は、-OH、C1~C6アルコキシ、C1~C6アルキルアミノカルボニル、-C(O)N(ORa)Ra2、E-3、E-6、E-7又はE-38を表し、
R12は、水素原子又はC1~C6アルキルを表し、
R13は、水素原子又はC1~C6アルキルを表し、
R14は、C1~C6アルキル又はC1~C6アルキルカルボニルを表し、
R15は、シアノ、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルキル、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R17は、水素原子、C1~C6アルキル又は-CH2C(O)Raを表し、
R18は、水素原子、C1~C6アルキル又はフェニルを表し、
Raは、C1~C6アルキルを表し、
Ra1は、水素原子、C1~C6アルキル、フェニル又は(Z1)mによって置換されたフェニルを表し、
Ra2は、C1~C6アルキルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、又は互いに相異なっても良く、
Z1は、シアノ、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、又は互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、シアノ、C1~C6アルキル、C1~C6アルコキシ、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-CH2CN又は-C(O)C(O)ORaを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を表し、p5が2、3、4又は5の整数を表し、p7が2、3、4、5、6又は7の整数を表す場合には、各々のZ9は互いに同一であっても、又は互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、又は互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表されるチエノウラシル化合物又はその塩。 R 8 is C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, —C(=NOR 17 )R 18 , —C(=NNR 13 R 14 )R a1 , —C(=NCN)R a1 , represents phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkyl amino, di(C 1 -C 6 alkyl)amino, —C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65, E-1 to E- 89 or E-90,
R 10 represents phenyl,
R 11 is —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylaminocarbonyl, —C(O)N(OR a )R a2 , E-3, E-6, E-7 or E- represents 38,
R 12 represents a hydrogen atom or C 1 -C 6 alkyl,
R 13 represents a hydrogen atom or C 1 -C 6 alkyl,
R 14 represents C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl,
R 15 represents cyano, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 17 represents a hydrogen atom, C 1 -C 6 alkyl or —CH 2 C(O)R a ,
R 18 represents a hydrogen atom, C 1 -C 6 alkyl or phenyl;
R a represents C 1 -C 6 alkyl,
R a1 represents a hydrogen atom, C 1 -C 6 alkyl, phenyl or phenyl substituted by (Z 1 ) m ;
R a2 represents C 1 -C 6 alkyl,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents cyano, a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a is cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 6 alkyl)aminocarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —CH CN or —C ( O)C(O)OR a ,
In relation to Z9, p2 represents an integer of 2, p3 represents an integer of 2 or 3, p4 represents an integer of 2, 3 or 4, and p5 represents an integer of 2, 3, 4 or 5. and when p represents an integer of 2, 3, 4, 5, 6 or 7, each Z 9 may be the same as or different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
A thienouracil compound represented by or a salt thereof.
〔2〕
R1は、C1~C6アルキルを表し、
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、-C(O)R9又はフェニルを表し、
R3は、フェニル又は(Z)m1によって置換されたフェニルを表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル、E-38、E-41、E-44、L-5又はL-6を表し、
R8は、C3~C6シクロアルキル、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-22、G-23又はG-53を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、G-1、G-3、G-4、G-15~G-17、G-21、G-22、G-52、G-53、E-45又はE-76を表し、
R11は、C1~C6アルキルアミノカルボニル又は-C(O)N(ORa)Ra2を表し、
R15は、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R18は、C1~C6アルキル又はフェニルを表し、
Ra1は、C1~C6アルキルを表し、
Z1は、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
Zaは、C1~C6アルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル又は-C(O)C(O)ORaを表し、
m及びm1は、1又は2の整数を表す、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [2]
R 1 represents C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, represents C 3 -C 6 cycloalkoxycarbonyl, —C(O)R 9 or phenyl,
R 3 represents phenyl or phenyl substituted by (Z) m1 ,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 , E-38, representing E-41, E-44, L-5 or L-6,
R 8 is C 3 -C 6 cycloalkyl, —C(═NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-22, G-23 or represents G-53,
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 6alkyl )amino, —C(=NOR a )R a1 , phenyl, G-1, G-3, G-4, G-15 to G-17, G-21, G-22, G-52, G -53, E-45 or E-76,
R 11 represents C 1 -C 6 alkylaminocarbonyl or —C(O)N(OR a )R a2 ,
R 15 represents C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 18 represents C 1 -C 6 alkyl or phenyl,
R a1 represents C 1 -C 6 alkyl,
Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
Z a is C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl, di(C 1 - C6 alkyl)aminosulfonyl or —C(O)C(O)OR a ,
The thienouracil compound or salt thereof according to [1] above, wherein m and m1 represent an integer of 1 or 2.
R1は、C1~C6アルキルを表し、
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、-C(O)R9又はフェニルを表し、
R3は、フェニル又は(Z)m1によって置換されたフェニルを表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル、E-38、E-41、E-44、L-5又はL-6を表し、
R8は、C3~C6シクロアルキル、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-22、G-23又はG-53を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、G-1、G-3、G-4、G-15~G-17、G-21、G-22、G-52、G-53、E-45又はE-76を表し、
R11は、C1~C6アルキルアミノカルボニル又は-C(O)N(ORa)Ra2を表し、
R15は、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R18は、C1~C6アルキル又はフェニルを表し、
Ra1は、C1~C6アルキルを表し、
Z1は、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
Zaは、C1~C6アルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル又は-C(O)C(O)ORaを表し、
m及びm1は、1又は2の整数を表す、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [2]
R 1 represents C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, represents C 3 -C 6 cycloalkoxycarbonyl, —C(O)R 9 or phenyl,
R 3 represents phenyl or phenyl substituted by (Z) m1 ,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 , E-38, representing E-41, E-44, L-5 or L-6,
R 8 is C 3 -C 6 cycloalkyl, —C(═NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-22, G-23 or represents G-53,
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 6alkyl )amino, —C(=NOR a )R a1 , phenyl, G-1, G-3, G-4, G-15 to G-17, G-21, G-22, G-52, G -53, E-45 or E-76,
R 11 represents C 1 -C 6 alkylaminocarbonyl or —C(O)N(OR a )R a2 ,
R 15 represents C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 18 represents C 1 -C 6 alkyl or phenyl,
R a1 represents C 1 -C 6 alkyl,
Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
Z a is C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl, di(C 1 - C6 alkyl)aminosulfonyl or —C(O)C(O)OR a ,
The thienouracil compound or salt thereof according to [1] above, wherein m and m1 represent an integer of 1 or 2.
〔3〕
R2は、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9又はフェニルを表し、
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、E-38、E-44又はL-5を表し、
R7は、C1~C6アルキルを表し、
R8は、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-23又はG-53を表し、
R9は、C1~C6アルキル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、-C(=NORa)Ra1、フェニル、G-3、G-4、G-15~G-17、G-21、G-22、G-52又はG-53を表し、
R11は、C1~C6アルキルアミノカルボニルを表し、
R12は、C1~C6アルキルを表し、
R15は、C1~C6アルコキシを表し、
R17は、C1~C6アルキルを表し、
Zaは、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル又はジ(C1~C6アルキル)アミノカルボニルを表す、上記〔2〕に記載のチエノウラシル化合物又はその塩。 [3]
R 2 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or phenyl; represent,
R 4 represents —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5;
R 7 represents C 1 -C 6 alkyl,
R 8 represents -C(=NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-23 or G-53;
R 9 is C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, —C(=NOR a )R a1 , phenyl, G-3, G-4, G- 15 to G-17, G-21, G-22, G-52 or G-53;
R 11 represents C 1 -C 6 alkylaminocarbonyl,
R 12 represents C 1 -C 6 alkyl,
R 15 represents C 1 -C 6 alkoxy,
R 17 represents C 1 -C 6 alkyl,
The thienouracil according to [2] above, wherein Z a represents C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)aminocarbonyl. compound or its salt.
R2は、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9又はフェニルを表し、
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、E-38、E-44又はL-5を表し、
R7は、C1~C6アルキルを表し、
R8は、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-23又はG-53を表し、
R9は、C1~C6アルキル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、-C(=NORa)Ra1、フェニル、G-3、G-4、G-15~G-17、G-21、G-22、G-52又はG-53を表し、
R11は、C1~C6アルキルアミノカルボニルを表し、
R12は、C1~C6アルキルを表し、
R15は、C1~C6アルコキシを表し、
R17は、C1~C6アルキルを表し、
Zaは、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル又はジ(C1~C6アルキル)アミノカルボニルを表す、上記〔2〕に記載のチエノウラシル化合物又はその塩。 [3]
R 2 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or phenyl; represent,
R 4 represents —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5;
R 7 represents C 1 -C 6 alkyl,
R 8 represents -C(=NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-23 or G-53;
R 9 is C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, —C(=NOR a )R a1 , phenyl, G-3, G-4, G- 15 to G-17, G-21, G-22, G-52 or G-53;
R 11 represents C 1 -C 6 alkylaminocarbonyl,
R 12 represents C 1 -C 6 alkyl,
R 15 represents C 1 -C 6 alkoxy,
R 17 represents C 1 -C 6 alkyl,
The thienouracil according to [2] above, wherein Z a represents C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)aminocarbonyl. compound or its salt.
〔4〕
R2は、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表し、
R4は、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、E-38、E-44又はL-5を表し、
R8は、-C(=NOR17)R18、G-3又はG-4を表し、
R9は、G-3、G-4、G-21又はG-22を表し、
R18は、C1~C6アルキルを表し、
Zaは、C1~C6アルコキシカルボニルを表す、上記〔3〕に記載のチエノウラシル化合物又はその塩。 [4]
R 2 represents C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 ;
R 4 represents C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents E-38, E-44 or L-5;
R 8 represents -C(=NOR 17 )R 18 , G-3 or G-4;
R 9 represents G-3, G-4, G-21 or G-22;
R 18 represents C 1 -C 6 alkyl,
The thienouracil compound or a salt thereof according to [3] above, wherein Z a represents C 1 -C 6 alkoxycarbonyl.
R2は、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表し、
R4は、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、E-38、E-44又はL-5を表し、
R8は、-C(=NOR17)R18、G-3又はG-4を表し、
R9は、G-3、G-4、G-21又はG-22を表し、
R18は、C1~C6アルキルを表し、
Zaは、C1~C6アルコキシカルボニルを表す、上記〔3〕に記載のチエノウラシル化合物又はその塩。 [4]
R 2 represents C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 ;
R 4 represents C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents E-38, E-44 or L-5;
R 8 represents -C(=NOR 17 )R 18 , G-3 or G-4;
R 9 represents G-3, G-4, G-21 or G-22;
R 18 represents C 1 -C 6 alkyl,
The thienouracil compound or a salt thereof according to [3] above, wherein Z a represents C 1 -C 6 alkoxycarbonyl.
〔5〕
R4は、L-1を表す、上記〔4〕に記載のチエノウラシル化合物又はその塩。 [5]
The thienouracil compound or a salt thereof according to [4] above, wherein R 4 represents L-1.
R4は、L-1を表す、上記〔4〕に記載のチエノウラシル化合物又はその塩。 [5]
The thienouracil compound or a salt thereof according to [4] above, wherein R 4 represents L-1.
〔6〕
R4は、R15によって置換されたC1~C6アルキルを表す、上記〔4〕に記載のチエノウラシル化合物又はその塩。 [6]
The thienouracil compound or a salt thereof according to [4] above, wherein R 4 represents C 1 -C 6 alkyl substituted by R 15 .
R4は、R15によって置換されたC1~C6アルキルを表す、上記〔4〕に記載のチエノウラシル化合物又はその塩。 [6]
The thienouracil compound or a salt thereof according to [4] above, wherein R 4 represents C 1 -C 6 alkyl substituted by R 15 .
〔7〕
R1は、水素原子を表す、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [7]
The thienouracil compound or salt thereof according to [1] above, wherein R 1 represents a hydrogen atom.
R1は、水素原子を表す、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [7]
The thienouracil compound or salt thereof according to [1] above, wherein R 1 represents a hydrogen atom.
〔8〕
R1は、メチルを表す、上記〔1〕~〔6〕に記載のチエノウラシル化合物又はその塩。 [8]
The thienouracil compound or a salt thereof according to [1] to [6] above, wherein R 1 represents methyl.
R1は、メチルを表す、上記〔1〕~〔6〕に記載のチエノウラシル化合物又はその塩。 [8]
The thienouracil compound or a salt thereof according to [1] to [6] above, wherein R 1 represents methyl.
〔9〕
R2は、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9又はフェニルを表す、上記〔1〕~〔2〕、〔7〕~〔8〕に記載のチエノウラシル化合物又はその塩。 [9]
R 2 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or phenyl; The thienouracil compound or a salt thereof according to [1] to [2] and [7] to [8] above.
R2は、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9又はフェニルを表す、上記〔1〕~〔2〕、〔7〕~〔8〕に記載のチエノウラシル化合物又はその塩。 [9]
R 2 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or phenyl; The thienouracil compound or a salt thereof according to [1] to [2] and [7] to [8] above.
〔10〕
R2は、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表す、上記〔1〕~〔3〕、〔7〕~〔8〕に記載のチエノウラシル化合物又はその塩。 [10]
R 2 represents C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 , the above [1] to [3 ], the thienouracil compound or a salt thereof according to [7] to [8].
R2は、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表す、上記〔1〕~〔3〕、〔7〕~〔8〕に記載のチエノウラシル化合物又はその塩。 [10]
R 2 represents C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 , the above [1] to [3 ], the thienouracil compound or a salt thereof according to [7] to [8].
〔11〕
R2は、R8によって置換されたC1~C6アルキルを表し、
R8は、C3~C6シクロアルキル、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-22、G-23又はG-53を表し、Z1はハロゲン原子を表し、mは1又は2を表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [11]
R 2 represents C 1 -C 6 alkyl substituted by R 8 ,
R 8 is C 3 -C 6 cycloalkyl, —C(═NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-22, G-23 or G-53, Z 1 represents a halogen atom, and m represents 1 or 2, the thienouracil compound or a salt thereof according to [10] above.
R2は、R8によって置換されたC1~C6アルキルを表し、
R8は、C3~C6シクロアルキル、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-22、G-23又はG-53を表し、Z1はハロゲン原子を表し、mは1又は2を表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [11]
R 2 represents C 1 -C 6 alkyl substituted by R 8 ,
R 8 is C 3 -C 6 cycloalkyl, —C(═NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-22, G-23 or G-53, Z 1 represents a halogen atom, and m represents 1 or 2, the thienouracil compound or a salt thereof according to [10] above.
〔12〕
R8は、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-23又はG-53を表す、上記〔11〕に記載のチエノウラシル化合物又はその塩。 [12]
R 8 represents -C(=NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-23 or G-53, the above [11] A thienouracil compound or a salt thereof as described.
R8は、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-23又はG-53を表す、上記〔11〕に記載のチエノウラシル化合物又はその塩。 [12]
R 8 represents -C(=NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-23 or G-53, the above [11] A thienouracil compound or a salt thereof as described.
〔13〕
R8は、-C(=NOR17)R18、G-3又はG-4を表す、上記〔12〕に記載のチエノウラシル化合物又はその塩。 [13]
The thienouracil compound or a salt thereof according to [12] above, wherein R 8 represents -C(=NOR 17 )R 18 , G-3 or G-4.
R8は、-C(=NOR17)R18、G-3又はG-4を表す、上記〔12〕に記載のチエノウラシル化合物又はその塩。 [13]
The thienouracil compound or a salt thereof according to [12] above, wherein R 8 represents -C(=NOR 17 )R 18 , G-3 or G-4.
〔14〕
R8は、-C(=NOR17)R18を表す、上記〔13〕に記載のチエノウラシル化合物又はその塩。 [14]
The thienouracil compound or a salt thereof according to [13] above, wherein R 8 represents -C(=NOR 17 )R 18 .
R8は、-C(=NOR17)R18を表す、上記〔13〕に記載のチエノウラシル化合物又はその塩。 [14]
The thienouracil compound or a salt thereof according to [13] above, wherein R 8 represents -C(=NOR 17 )R 18 .
〔15〕
R8は、G-3を表し、Z9はメチルを表し、p3は0又は1の整数を表す、上記〔13〕に記載のチエノウラシル化合物又はその塩。 [15]
The thienouracil compound or a salt thereof according to [13] above, wherein R 8 represents G-3, Z 9 represents methyl, and p3 represents an integer of 0 or 1.
R8は、G-3を表し、Z9はメチルを表し、p3は0又は1の整数を表す、上記〔13〕に記載のチエノウラシル化合物又はその塩。 [15]
The thienouracil compound or a salt thereof according to [13] above, wherein R 8 represents G-3, Z 9 represents methyl, and p3 represents an integer of 0 or 1.
〔16〕
R8は、G-4を表し、p3は0を表す、上記〔13〕に記載のチエノウラシル化合物又はその塩。 [16]
The thienouracil compound or a salt thereof according to [13] above, wherein R 8 represents G-4 and p3 represents 0.
R8は、G-4を表し、p3は0を表す、上記〔13〕に記載のチエノウラシル化合物又はその塩。 [16]
The thienouracil compound or a salt thereof according to [13] above, wherein R 8 represents G-4 and p3 represents 0.
〔17〕
R2は、C2~C6ハロアルケニルを表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [17]
The thienouracil compound or a salt thereof according to [10] above, wherein R 2 represents a C 2 -C 6 haloalkenyl.
R2は、C2~C6ハロアルケニルを表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [17]
The thienouracil compound or a salt thereof according to [10] above, wherein R 2 represents a C 2 -C 6 haloalkenyl.
〔18〕
R2は、C1~C6アルコキシカルボニルを表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [18]
The thienouracil compound or a salt thereof according to [10] above, wherein R 2 represents C 1 -C 6 alkoxycarbonyl.
R2は、C1~C6アルコキシカルボニルを表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [18]
The thienouracil compound or a salt thereof according to [10] above, wherein R 2 represents C 1 -C 6 alkoxycarbonyl.
〔19〕
R2は、-C(O)R9を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、G-1、G-3、G-4、G-15~G-17、G-21、G-22、G-52、G-53、E-45又はE-76を表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [19]
R 2 represents —C(O)R 9 ;
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 6alkyl )amino, —C(=NOR a )R a1 , phenyl, G-1, G-3, G-4, G-15 to G-17, G-21, G-22, G-52, G -53, E-45 or E-76, the thienouracil compound or its salt according to the above [10].
R2は、-C(O)R9を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、G-1、G-3、G-4、G-15~G-17、G-21、G-22、G-52、G-53、E-45又はE-76を表す、上記〔10〕に記載のチエノウラシル化合物又はその塩。 [19]
R 2 represents —C(O)R 9 ;
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 6alkyl )amino, —C(=NOR a )R a1 , phenyl, G-1, G-3, G-4, G-15 to G-17, G-21, G-22, G-52, G -53, E-45 or E-76, the thienouracil compound or its salt according to the above [10].
〔20〕
R9は、C1~C6アルキル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、-C(=NORa)Ra1、フェニル、G-3、G-4、G-15~G-17、G-21、G-22、G-52又はG-53を表す、上記〔19〕に記載のチエノウラシル化合物又はその塩。 [20]
R 9 is C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, —C(=NOR a )R a1 , phenyl, G-3, G-4, G- 15 to G-17, G-21, G-22, G-52 or G-53, the thienouracil compound or a salt thereof according to [19] above.
R9は、C1~C6アルキル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、-C(=NORa)Ra1、フェニル、G-3、G-4、G-15~G-17、G-21、G-22、G-52又はG-53を表す、上記〔19〕に記載のチエノウラシル化合物又はその塩。 [20]
R 9 is C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, —C(=NOR a )R a1 , phenyl, G-3, G-4, G- 15 to G-17, G-21, G-22, G-52 or G-53, the thienouracil compound or a salt thereof according to [19] above.
〔21〕
R9は、G-3、G-4、G-21又はG-22を表す、上記〔20〕に記載のチエノウラシル化合物又はその塩。 [21]
The thienouracil compound or a salt thereof according to [20] above, wherein R 9 represents G-3, G-4, G-21 or G-22.
R9は、G-3、G-4、G-21又はG-22を表す、上記〔20〕に記載のチエノウラシル化合物又はその塩。 [21]
The thienouracil compound or a salt thereof according to [20] above, wherein R 9 represents G-3, G-4, G-21 or G-22.
〔22〕
R9は、-C(=NORa)Ra1、フェニル、G-3又はG-4を表し、上記〔20〕に記載のチエノウラシル化合物又はその塩。 [22]
R 9 represents -C(=NOR a )R a1 , phenyl, G-3 or G-4, and the thienouracil compound or a salt thereof according to [20] above.
R9は、-C(=NORa)Ra1、フェニル、G-3又はG-4を表し、上記〔20〕に記載のチエノウラシル化合物又はその塩。 [22]
R 9 represents -C(=NOR a )R a1 , phenyl, G-3 or G-4, and the thienouracil compound or a salt thereof according to [20] above.
〔23〕
R9は、G-3を表し、Z9はメチル又は塩素原子を表し、p3は0又は1の整数を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [23]
The thienouracil compound or salt thereof according to [21] above, wherein R 9 represents G-3, Z 9 represents a methyl or chlorine atom, and p3 represents an integer of 0 or 1.
R9は、G-3を表し、Z9はメチル又は塩素原子を表し、p3は0又は1の整数を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [23]
The thienouracil compound or salt thereof according to [21] above, wherein R 9 represents G-3, Z 9 represents a methyl or chlorine atom, and p3 represents an integer of 0 or 1.
〔24〕
R9は、G-4を表し、p3は0を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [24]
The thienouracil compound or a salt thereof according to [21] above, wherein R 9 represents G-4 and p3 represents 0.
R9は、G-4を表し、p3は0を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [24]
The thienouracil compound or a salt thereof according to [21] above, wherein R 9 represents G-4 and p3 represents 0.
〔25〕
R9は、G-21を表し、Z9はメチルを表し、p2は0又は1の整数を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [25]
The thienouracil compound or its salt according to [21] above, wherein R 9 represents G-21, Z 9 represents methyl, and p2 represents an integer of 0 or 1.
R9は、G-21を表し、Z9はメチルを表し、p2は0又は1の整数を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [25]
The thienouracil compound or its salt according to [21] above, wherein R 9 represents G-21, Z 9 represents methyl, and p2 represents an integer of 0 or 1.
〔26〕
R9は、G-22を表し、Z9はハロゲン原子又はC1~C6アルキルを表し、p2は0又は1の整数を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [26]
The thienouracil compound or its salt according to [21] above, wherein R 9 represents G-22, Z 9 represents a halogen atom or C 1 -C 6 alkyl, and p2 represents an integer of 0 or 1.
R9は、G-22を表し、Z9はハロゲン原子又はC1~C6アルキルを表し、p2は0又は1の整数を表す、上記〔21〕に記載のチエノウラシル化合物又はその塩。 [26]
The thienouracil compound or its salt according to [21] above, wherein R 9 represents G-22, Z 9 represents a halogen atom or C 1 -C 6 alkyl, and p2 represents an integer of 0 or 1.
〔27〕
R3は、フェニル又は(Z)m1によって置換されたフェニルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1は、1又は2の整数を表す、上記〔1〕、〔5〕~〔26〕に記載のチエノウラシル化合物又はその塩。 [27]
R 3 represents phenyl or phenyl substituted by (Z) m1 ,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
The thienouracil compound or salt thereof according to the above [1], [5] to [26], wherein m1 represents an integer of 1 or 2.
R3は、フェニル又は(Z)m1によって置換されたフェニルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1は、1又は2の整数を表す、上記〔1〕、〔5〕~〔26〕に記載のチエノウラシル化合物又はその塩。 [27]
R 3 represents phenyl or phenyl substituted by (Z) m1 ,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
The thienouracil compound or salt thereof according to the above [1], [5] to [26], wherein m1 represents an integer of 1 or 2.
〔28〕
R3は、フェニルを表す、上記〔27〕に記載のチエノウラシル化合物又はその塩。 [28]
The thienouracil compound or a salt thereof according to [27] above, wherein R 3 represents phenyl.
R3は、フェニルを表す、上記〔27〕に記載のチエノウラシル化合物又はその塩。 [28]
The thienouracil compound or a salt thereof according to [27] above, wherein R 3 represents phenyl.
〔29〕
R3は、(Z)m1によって置換されたフェニルを表す、上記〔27〕に記載のチエノウラシル化合物又はその塩。 [29]
The thienouracil compound or a salt thereof according to [27] above, wherein R 3 represents phenyl substituted with (Z) m1 .
R3は、(Z)m1によって置換されたフェニルを表す、上記〔27〕に記載のチエノウラシル化合物又はその塩。 [29]
The thienouracil compound or a salt thereof according to [27] above, wherein R 3 represents phenyl substituted with (Z) m1 .
〔30〕
Zは、ハロゲン原子又はC1~C6アルコキシを表し、m1は2の整数を表す、上記〔29〕に記載のチエノウラシル化合物又はその塩。 [30]
The thienouracil compound or salt thereof according to [29] above, wherein Z represents a halogen atom or C 1 to C 6 alkoxy, and m1 represents an integer of 2.
Zは、ハロゲン原子又はC1~C6アルコキシを表し、m1は2の整数を表す、上記〔29〕に記載のチエノウラシル化合物又はその塩。 [30]
The thienouracil compound or salt thereof according to [29] above, wherein Z represents a halogen atom or C 1 to C 6 alkoxy, and m1 represents an integer of 2.
〔31〕
Zは、フッ素原子又はメトキシを表す、上記〔30〕に記載のチエノウラシル化合物又はその塩。 [31]
The thienouracil compound or salt thereof according to [30] above, wherein Z represents a fluorine atom or methoxy.
Zは、フッ素原子又はメトキシを表す、上記〔30〕に記載のチエノウラシル化合物又はその塩。 [31]
The thienouracil compound or salt thereof according to [30] above, wherein Z represents a fluorine atom or methoxy.
〔32〕
Zは、ハロゲン原子を表し、m1は、1の整数を表す、上記〔29〕に記載のチエノウラシル化合物又はその塩。 [32]
The thienouracil compound or salt thereof according to [29] above, wherein Z represents a halogen atom and m1 represents an integer of 1.
Zは、ハロゲン原子を表し、m1は、1の整数を表す、上記〔29〕に記載のチエノウラシル化合物又はその塩。 [32]
The thienouracil compound or salt thereof according to [29] above, wherein Z represents a halogen atom and m1 represents an integer of 1.
〔33〕
Zは、フッ素原子又は塩素原子を表す、上記〔32〕に記載のチエノウラシル化合物又はその塩。 [33]
The thienouracil compound or salt thereof according to [32] above, wherein Z represents a fluorine atom or a chlorine atom.
Zは、フッ素原子又は塩素原子を表す、上記〔32〕に記載のチエノウラシル化合物又はその塩。 [33]
The thienouracil compound or salt thereof according to [32] above, wherein Z represents a fluorine atom or a chlorine atom.
〔34〕
Zは、C1~C6アルコキシを表し、m1は1の整数を表す、上記〔29〕に記載のチエノウラシル化合物又はその塩。 [34]
The thienouracil compound or a salt thereof according to [29] above, wherein Z represents C 1 to C 6 alkoxy and m1 represents an integer of 1.
Zは、C1~C6アルコキシを表し、m1は1の整数を表す、上記〔29〕に記載のチエノウラシル化合物又はその塩。 [34]
The thienouracil compound or a salt thereof according to [29] above, wherein Z represents C 1 to C 6 alkoxy and m1 represents an integer of 1.
〔35〕
Zは、メトキシ又はエトキシを表す、上記〔34〕に記載のチエノウラシル化合物又はその塩。 [35]
The thienouracil compound or salt thereof according to [34] above, wherein Z represents methoxy or ethoxy.
Zは、メトキシ又はエトキシを表す、上記〔34〕に記載のチエノウラシル化合物又はその塩。 [35]
The thienouracil compound or salt thereof according to [34] above, wherein Z represents methoxy or ethoxy.
〔36〕
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル、C1~C6アルキルチオ、C1~C6アルキルスルフィニル、C1~C6アルキルスルホニル、L-1~L-3又はL-4を表し、R15は、C1~C6アルコキシを表す、上記〔1〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [36]
R 4 is —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 , C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, L- 1 to L-3 or L-4, and R 15 represents C 1 to C 6 alkoxy, the thienouracil compound or a salt thereof according to the above [1], [7] to [35].
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル、C1~C6アルキルチオ、C1~C6アルキルスルフィニル、C1~C6アルキルスルホニル、L-1~L-3又はL-4を表し、R15は、C1~C6アルコキシを表す、上記〔1〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [36]
R 4 is —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 , C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, L- 1 to L-3 or L-4, and R 15 represents C 1 to C 6 alkoxy, the thienouracil compound or a salt thereof according to the above [1], [7] to [35].
〔37〕
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又はL-1を表し、R15は、C1~C6アルコキシを表す、上記〔1〕~〔2〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [37]
R 4 represents —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1, and R 15 represents C 1 -C 6 alkoxy, the above [1] to [ 2], the thienouracil compound or a salt thereof according to [7] to [35].
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又はL-1を表し、R15は、C1~C6アルコキシを表す、上記〔1〕~〔2〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [37]
R 4 represents —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1, and R 15 represents C 1 -C 6 alkoxy, the above [1] to [ 2], the thienouracil compound or a salt thereof according to [7] to [35].
〔38〕
R4は、R15によって置換されたC1~C6アルキル又はL-1を表し、R15は、C1~C6アルコキシを表す、上記〔1〕~〔3〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [38]
R 4 represents C 1 -C 6 alkyl substituted by R 15 or L-1, and R 15 represents C 1 -C 6 alkoxy, the above [1] to [3], [7] to [ 35], the thienouracil compound or a salt thereof.
R4は、R15によって置換されたC1~C6アルキル又はL-1を表し、R15は、C1~C6アルコキシを表す、上記〔1〕~〔3〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [38]
R 4 represents C 1 -C 6 alkyl substituted by R 15 or L-1, and R 15 represents C 1 -C 6 alkoxy, the above [1] to [3], [7] to [ 35], the thienouracil compound or a salt thereof.
〔39〕
R4は、L-1を表す、上記〔1〕~〔4〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [39]
The thienouracil compound or a salt thereof according to the above [1] to [4] and [7] to [35], wherein R 4 represents L-1.
R4は、L-1を表す、上記〔1〕~〔4〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [39]
The thienouracil compound or a salt thereof according to the above [1] to [4] and [7] to [35], wherein R 4 represents L-1.
〔40〕
R4は、R15によって置換されたC1~C6アルキルを表し、R15は、C1~C6アルコキシを表す、上記〔1〕~〔4〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [40]
[1] to [4] and [7] to [35] above, wherein R 4 represents C 1 -C 6 alkyl substituted by R 15 and R 15 represents C 1 -C 6 alkoxy A thienouracil compound or a salt thereof.
R4は、R15によって置換されたC1~C6アルキルを表し、R15は、C1~C6アルコキシを表す、上記〔1〕~〔4〕、〔7〕~〔35〕に記載のチエノウラシル化合物又はその塩。 [40]
[1] to [4] and [7] to [35] above, wherein R 4 represents C 1 -C 6 alkyl substituted by R 15 and R 15 represents C 1 -C 6 alkoxy A thienouracil compound or a salt thereof.
〔41〕
R4は、R15によって置換されたC1アルキルを表し、
R15は、メトキシ又はエトキシを表す、上記〔40〕に記載のチエノウラシル化合物又はその塩。 [41]
R 4 represents C 1 alkyl substituted by R 15 ,
The thienouracil compound or salt thereof according to [40] above, wherein R 15 represents methoxy or ethoxy.
R4は、R15によって置換されたC1アルキルを表し、
R15は、メトキシ又はエトキシを表す、上記〔40〕に記載のチエノウラシル化合物又はその塩。 [41]
R 4 represents C 1 alkyl substituted by R 15 ,
The thienouracil compound or salt thereof according to [40] above, wherein R 15 represents methoxy or ethoxy.
〔42〕
R4は、-C≡C-R7を表し、R7は、水素原子、C1~C6アルキル又はトリ(C1~C6アルキル)シリルを表す、上記〔37〕に記載のチエノウラシル化合物又はその塩。 [42]
The thienouracil compound according to [37] above, wherein R 4 represents —C≡C—R 7 and R 7 represents a hydrogen atom, C 1 -C 6 alkyl or tri(C 1 -C 6 alkyl)silyl Or its salt.
R4は、-C≡C-R7を表し、R7は、水素原子、C1~C6アルキル又はトリ(C1~C6アルキル)シリルを表す、上記〔37〕に記載のチエノウラシル化合物又はその塩。 [42]
The thienouracil compound according to [37] above, wherein R 4 represents —C≡C—R 7 and R 7 represents a hydrogen atom, C 1 -C 6 alkyl or tri(C 1 -C 6 alkyl)silyl Or its salt.
〔43〕
R7は、C1~C6アルキルを表す、上記〔42〕に記載のチエノウラシル化合物又はその塩。 [43]
The thienouracil compound or a salt thereof according to [42] above, wherein R 7 represents C 1 -C 6 alkyl.
R7は、C1~C6アルキルを表す、上記〔42〕に記載のチエノウラシル化合物又はその塩。 [43]
The thienouracil compound or a salt thereof according to [42] above, wherein R 7 represents C 1 -C 6 alkyl.
〔44〕
R7は、メチルを表す、上記〔43〕に記載のチエノウラシル化合物又はその塩。 [44]
The thienouracil compound or a salt thereof according to [43] above, wherein R 7 represents methyl.
R7は、メチルを表す、上記〔43〕に記載のチエノウラシル化合物又はその塩。 [44]
The thienouracil compound or a salt thereof according to [43] above, wherein R 7 represents methyl.
〔45〕
R7は、トリメチルシリルを表す、上記〔42〕に記載のチエノウラシル化合物又はその塩。 [45]
The thienouracil compound or a salt thereof according to [42] above, wherein R 7 represents trimethylsilyl.
R7は、トリメチルシリルを表す、上記〔42〕に記載のチエノウラシル化合物又はその塩。 [45]
The thienouracil compound or a salt thereof according to [42] above, wherein R 7 represents trimethylsilyl.
〔46〕
R7は、水素原子を表す、上記〔42〕に記載のチエノウラシル化合物又はその塩 [46]
The thienouracil compound or salt thereof according to [42] above, wherein R 7 represents a hydrogen atom
R7は、水素原子を表す、上記〔42〕に記載のチエノウラシル化合物又はその塩 [46]
The thienouracil compound or salt thereof according to [42] above, wherein R 7 represents a hydrogen atom
〔47〕
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、E-38、E-44又はL-5を表す、上記〔1〕~〔2〕、〔7〕~〔45〕に記載のチエノウラシル化合物又はその塩 [47]
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5, above [1] to [2], [7] ~ Thienouracil compound or a salt thereof according to [45]
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、E-38、E-44又はL-5を表す、上記〔1〕~〔2〕、〔7〕~〔45〕に記載のチエノウラシル化合物又はその塩 [47]
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5, above [1] to [2], [7] ~ Thienouracil compound or a salt thereof according to [45]
〔48〕
R6は、R11によって置換されたC1~C6アルキル、E-38、E-44又はL-5を表す、上記、上記〔1〕~〔3〕、〔7〕~〔45〕に記載のチエノウラシル化合物又はその塩。 [48]
R 6 represents C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5, above [1] to [3], [7] to [45] A thienouracil compound or a salt thereof as described.
R6は、R11によって置換されたC1~C6アルキル、E-38、E-44又はL-5を表す、上記、上記〔1〕~〔3〕、〔7〕~〔45〕に記載のチエノウラシル化合物又はその塩。 [48]
R 6 represents C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5, above [1] to [3], [7] to [45] A thienouracil compound or a salt thereof as described.
〔49〕
R6は、E-38、E-44又はL-5を表す、上記〔1〕~〔48〕に記載のチエノウラシル化合物又はその塩。 [49]
The thienouracil compound or a salt thereof according to [1] to [48] above, wherein R 6 represents E-38, E-44 or L-5.
R6は、E-38、E-44又はL-5を表す、上記〔1〕~〔48〕に記載のチエノウラシル化合物又はその塩。 [49]
The thienouracil compound or a salt thereof according to [1] to [48] above, wherein R 6 represents E-38, E-44 or L-5.
〔50〕
R6は、R11によって置換されたC1~C6アルキルを表し、R11はC1~C6アルキルアミノカルボニルを表す、上記〔1〕~〔3〕、〔7〕~〔48〕に記載のチエノウラシル化合物又はその塩。 [50]
R 6 represents C 1 -C 6 alkyl substituted by R 11 , and R 11 represents C 1 -C 6 alkylaminocarbonyl; A thienouracil compound or a salt thereof as described.
R6は、R11によって置換されたC1~C6アルキルを表し、R11はC1~C6アルキルアミノカルボニルを表す、上記〔1〕~〔3〕、〔7〕~〔48〕に記載のチエノウラシル化合物又はその塩。 [50]
R 6 represents C 1 -C 6 alkyl substituted by R 11 , and R 11 represents C 1 -C 6 alkylaminocarbonyl; A thienouracil compound or a salt thereof as described.
〔51〕
R6は、R11によって置換されたC2アルキルを表し、R11はC1アルキルアミノカルボニルを表す、上記〔50〕に記載のチエノウラシル化合物又はその塩。 [51]
The thienouracil compound or a salt thereof according to [50] above, wherein R 6 represents C 2 alkyl substituted by R 11 , and R 11 represents C 1 alkylaminocarbonyl.
R6は、R11によって置換されたC2アルキルを表し、R11はC1アルキルアミノカルボニルを表す、上記〔50〕に記載のチエノウラシル化合物又はその塩。 [51]
The thienouracil compound or a salt thereof according to [50] above, wherein R 6 represents C 2 alkyl substituted by R 11 , and R 11 represents C 1 alkylaminocarbonyl.
〔52〕
R6は、E-38を表し、p9は0を表す、上記〔49〕に記載のチエノウラシル化合物又はその塩。 [52]
The thienouracil compound or a salt thereof according to [49] above, wherein R 6 represents E-38 and p9 represents 0.
R6は、E-38を表し、p9は0を表す、上記〔49〕に記載のチエノウラシル化合物又はその塩。 [52]
The thienouracil compound or a salt thereof according to [49] above, wherein R 6 represents E-38 and p9 represents 0.
〔53〕
R6は、E-44を表し、Zaは、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル又は-C(O)C(O)ORaを表し、p9は0を表す、上記〔49〕に記載のチエノウラシル化合物又はその塩。 [53]
R 6 represents E-44, Z a is C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl, The thienouracil compound or a salt thereof according to [49] above, which represents di(C 1 -C 6 alkyl)aminosulfonyl or —C(O)C(O)OR a , and p9 represents 0.
R6は、E-44を表し、Zaは、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル又は-C(O)C(O)ORaを表し、p9は0を表す、上記〔49〕に記載のチエノウラシル化合物又はその塩。 [53]
R 6 represents E-44, Z a is C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl, The thienouracil compound or a salt thereof according to [49] above, which represents di(C 1 -C 6 alkyl)aminosulfonyl or —C(O)C(O)OR a , and p9 represents 0.
〔54〕
Zaは、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル又はジ(C1~C6アルキル)アミノカルボニルを表す、上記〔53〕に記載のチエノウラシル化合物又はその塩。 [54]
The thienouracil according to [53] above, wherein Z a represents C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)aminocarbonyl compound or its salt.
Zaは、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル又はジ(C1~C6アルキル)アミノカルボニルを表す、上記〔53〕に記載のチエノウラシル化合物又はその塩。 [54]
The thienouracil according to [53] above, wherein Z a represents C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)aminocarbonyl compound or its salt.
〔55〕
Zaは、C1~C6アルキルカルボニルを表す、上記〔54〕に記載のチエノウラシル化合物又はその塩。 [55]
The thienouracil compound or a salt thereof according to [54] above, wherein Z a represents C 1 -C 6 alkylcarbonyl.
Zaは、C1~C6アルキルカルボニルを表す、上記〔54〕に記載のチエノウラシル化合物又はその塩。 [55]
The thienouracil compound or a salt thereof according to [54] above, wherein Z a represents C 1 -C 6 alkylcarbonyl.
〔56〕
Zaは、C1アルキルカルボニルを表す、上記〔55〕に記載のチエノウラシル化合物又はその塩。 [56]
The thienouracil compound or a salt thereof according to [55] above, wherein Za represents C1 alkylcarbonyl.
Zaは、C1アルキルカルボニルを表す、上記〔55〕に記載のチエノウラシル化合物又はその塩。 [56]
The thienouracil compound or a salt thereof according to [55] above, wherein Za represents C1 alkylcarbonyl.
〔57〕
R6は、L-5を表し、R12はメチルを表す、上記〔47〕~〔49〕に記載のチエノウラシル化合物又はその塩。 [57]
The thienouracil compound or a salt thereof according to [47] to [49] above, wherein R 6 represents L-5 and R 12 represents methyl.
R6は、L-5を表し、R12はメチルを表す、上記〔47〕~〔49〕に記載のチエノウラシル化合物又はその塩。 [57]
The thienouracil compound or a salt thereof according to [47] to [49] above, wherein R 6 represents L-5 and R 12 represents methyl.
〔58〕
R17及びR18は、メチルを表す、上記〔1〕~〔57〕に記載のチエノウラシル化合物又はその塩。 [58]
The thienouracil compound or a salt thereof according to [1] to [57] above, wherein R 17 and R 18 represent methyl.
R17及びR18は、メチルを表す、上記〔1〕~〔57〕に記載のチエノウラシル化合物又はその塩。 [58]
The thienouracil compound or a salt thereof according to [1] to [57] above, wherein R 17 and R 18 represent methyl.
〔59〕
Ra、R1a及びR2aは、メチルを表す、上記〔1〕~〔58〕に記載のチエノウラシル化合物又はその塩。 [59]
The thienouracil compound or a salt thereof according to [1] to [58] above, wherein R a , R 1a and R 2a represent methyl.
Ra、R1a及びR2aは、メチルを表す、上記〔1〕~〔58〕に記載のチエノウラシル化合物又はその塩。 [59]
The thienouracil compound or a salt thereof according to [1] to [58] above, wherein R a , R 1a and R 2a represent methyl.
〔60〕
R5は、メチルを表す、上記〔1〕~〔59〕に記載のチエノウラシル化合物又はその塩。 [60]
The thienouracil compound or a salt thereof according to [1] to [59] above, wherein R 5 represents methyl.
R5は、メチルを表す、上記〔1〕~〔59〕に記載のチエノウラシル化合物又はその塩。 [60]
The thienouracil compound or a salt thereof according to [1] to [59] above, wherein R 5 represents methyl.
〔61〕
m及びm1は、1又は2の整数を表し、
p2は、0又は1の整数を表し、
p3は、0又は1の整数を表し、
p4は、0又は1の整数を表し、
p8は、0を表し、
p9は、0を表し、
p10は、0を表す、上記〔1〕~〔60〕に記載のチエノウラシル化合物又はその塩。 [61]
m and m1 represent an integer of 1 or 2,
p2 represents an integer of 0 or 1,
p3 represents an integer of 0 or 1,
p4 represents an integer of 0 or 1,
p8 represents 0,
p9 represents 0,
The thienouracil compound or a salt thereof according to [1] to [60] above, wherein p10 represents 0.
m及びm1は、1又は2の整数を表し、
p2は、0又は1の整数を表し、
p3は、0又は1の整数を表し、
p4は、0又は1の整数を表し、
p8は、0を表し、
p9は、0を表し、
p10は、0を表す、上記〔1〕~〔60〕に記載のチエノウラシル化合物又はその塩。 [61]
m and m1 represent an integer of 1 or 2,
p2 represents an integer of 0 or 1,
p3 represents an integer of 0 or 1,
p4 represents an integer of 0 or 1,
p8 represents 0,
p9 represents 0,
The thienouracil compound or a salt thereof according to [1] to [60] above, wherein p10 represents 0.
〔62〕
mは1の整数を表し、m1は2の整数を表す、上記〔61〕に記載のチエノウラシル化合物又はその塩。 [62]
The thienouracil compound or its salt according to [61] above, wherein m represents an integer of 1 and m1 represents an integer of 2.
mは1の整数を表し、m1は2の整数を表す、上記〔61〕に記載のチエノウラシル化合物又はその塩。 [62]
The thienouracil compound or its salt according to [61] above, wherein m represents an integer of 1 and m1 represents an integer of 2.
〔63〕
R1は、水素原子又は1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9又はG-1~G-65を表し、
R3は、フェニル又は(Z)m1によって置換されたフェニルを表し、
R4は、-C≡C-R7又はL-1を表し、
R5は、C1~C6アルキルを表し、
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル又はE-1~E-90を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
R8は、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-3を表し、
R9は、C1~C6アルキルカルボニル、-C(=NORa)Ra1、フェニル又はG-1~G-65を表し、
R10は、フェニルを表し、
R11は、-OH又はC1~C6アルコキシを表し、
Raは、C1~C6アルキルを表し、
Ra1は、C1~C6アルキルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、または互いに相異なっても良く、
Z1は、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、または互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、C1~C6アルキルを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を示す場合には、各々のZ9は互いに同一であっても、または互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、または互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表される、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [63]
R 1 represents a hydrogen atom or 1 - C6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or represents G-1 to G-65,
R 3 represents phenyl or phenyl substituted by (Z) m1 ,
R 4 represents -C≡C-R 7 or L-1,
R 5 represents C 1 -C 6 alkyl,
R b represents a hydrogen atom,
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 or E-1 to E-90;
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
R 8 represents -C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m or G-3;
R 9 represents C 1 -C 6 alkylcarbonyl, —C(═NOR a )R a1 , phenyl or G-1 to G-65;
R 10 represents phenyl,
R 11 represents —OH or C 1 -C 6 alkoxy,
R a represents C 1 -C 6 alkyl,
R a1 represents C 1 -C 6 alkyl,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a represents C 1 -C 6 alkyl,
In relation to Z 9 , when p2 represents an integer of 2, p3 represents an integer of 2 or 3, and p4 represents an integer of 2, 3 or 4, each Z 9 is the same as each other. may be different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
The thienouracil compound or a salt thereof according to [1] above.
R1は、水素原子又は1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9又はG-1~G-65を表し、
R3は、フェニル又は(Z)m1によって置換されたフェニルを表し、
R4は、-C≡C-R7又はL-1を表し、
R5は、C1~C6アルキルを表し、
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル又はE-1~E-90を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
R8は、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-3を表し、
R9は、C1~C6アルキルカルボニル、-C(=NORa)Ra1、フェニル又はG-1~G-65を表し、
R10は、フェニルを表し、
R11は、-OH又はC1~C6アルコキシを表し、
Raは、C1~C6アルキルを表し、
Ra1は、C1~C6アルキルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、または互いに相異なっても良く、
Z1は、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、または互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、C1~C6アルキルを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を示す場合には、各々のZ9は互いに同一であっても、または互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、または互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表される、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [63]
R 1 represents a hydrogen atom or 1 - C6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or represents G-1 to G-65,
R 3 represents phenyl or phenyl substituted by (Z) m1 ,
R 4 represents -C≡C-R 7 or L-1,
R 5 represents C 1 -C 6 alkyl,
R b represents a hydrogen atom,
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 or E-1 to E-90;
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
R 8 represents -C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m or G-3;
R 9 represents C 1 -C 6 alkylcarbonyl, —C(═NOR a )R a1 , phenyl or G-1 to G-65;
R 10 represents phenyl,
R 11 represents —OH or C 1 -C 6 alkoxy,
R a represents C 1 -C 6 alkyl,
R a1 represents C 1 -C 6 alkyl,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a represents C 1 -C 6 alkyl,
In relation to Z 9 , when p2 represents an integer of 2, p3 represents an integer of 2 or 3, and p4 represents an integer of 2, 3 or 4, each Z 9 is the same as each other. may be different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
The thienouracil compound or a salt thereof according to [1] above.
〔64〕
R1は、C1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表し、
R3は、(Z)m1によって置換されたフェニルを表し、
R6は、C1~C6アルキル又はE-38を表し、
R9は、C1~C6アルキルカルボニル、フェニル、G-3、G-21又はG-22を表し、
Zは、ハロゲン原子又はC1~C6アルコキシを表し、
Z1は、ハロゲン原子を表す、上記〔63〕に記載のチエノウラシル化合物又はその塩。 [64]
R 1 represents C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 represents
R 3 represents phenyl substituted by (Z) m1 ,
R 6 represents C 1 -C 6 alkyl or E-38;
R 9 represents C 1 -C 6 alkylcarbonyl, phenyl, G-3, G-21 or G-22;
Z represents a halogen atom or C 1 -C 6 alkoxy;
The thienouracil compound or salt thereof according to [63] above, wherein Z 1 represents a halogen atom.
R1は、C1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表し、
R3は、(Z)m1によって置換されたフェニルを表し、
R6は、C1~C6アルキル又はE-38を表し、
R9は、C1~C6アルキルカルボニル、フェニル、G-3、G-21又はG-22を表し、
Zは、ハロゲン原子又はC1~C6アルコキシを表し、
Z1は、ハロゲン原子を表す、上記〔63〕に記載のチエノウラシル化合物又はその塩。 [64]
R 1 represents C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 represents
R 3 represents phenyl substituted by (Z) m1 ,
R 6 represents C 1 -C 6 alkyl or E-38;
R 9 represents C 1 -C 6 alkylcarbonyl, phenyl, G-3, G-21 or G-22;
Z represents a halogen atom or C 1 -C 6 alkoxy;
The thienouracil compound or salt thereof according to [63] above, wherein Z 1 represents a halogen atom.
〔65〕
mは、1の整数を表し、
m1は、1又は2の整数を表し、
p2、p3及びp9は、0を表す、上記〔64〕に記載のチエノウラシル化合物又はその塩。 [65]
m represents an integer of 1,
m1 represents an integer of 1 or 2,
The thienouracil compound or salt thereof according to [64] above, wherein p2, p3 and p9 represent 0;
mは、1の整数を表し、
m1は、1又は2の整数を表し、
p2、p3及びp9は、0を表す、上記〔64〕に記載のチエノウラシル化合物又はその塩。 [65]
m represents an integer of 1,
m1 represents an integer of 1 or 2,
The thienouracil compound or salt thereof according to [64] above, wherein p2, p3 and p9 represent 0;
〔66〕
Zはフッ素原子又はメトキシを表す、上記〔64〕又は〔65〕に記載のチエノウラシル化合物又はその塩。 [66]
The thienouracil compound or salt thereof according to [64] or [65] above, wherein Z represents a fluorine atom or methoxy.
Zはフッ素原子又はメトキシを表す、上記〔64〕又は〔65〕に記載のチエノウラシル化合物又はその塩。 [66]
The thienouracil compound or salt thereof according to [64] or [65] above, wherein Z represents a fluorine atom or methoxy.
〔67〕
R1は、水素原子又はC1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R3は、フェニル、(Z)m1によって置換されたフェニル、F-31又はF-34を表し、
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又は、L-1~L-4を表し、
R5は、C1~C6アルキルを表し、
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、R16によって置換されたC3~C6シクロアルキル又はE-1~E-90を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
R8は、-C(=NORa)Ra1、-C(=NNR13R14)Ra1、-C(=NCN)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、C1~C6アルキルアミノ、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R10は、フェニルを表し、
R11は、-OH、C1~C6アルコキシ、E-3、E-6、E-7又はE-38を表し、
R13は、水素原子又はC1~C6アルキルを表し、
R14は、C1~C6アルキル又はC1~C6アルキルカルボニルを表し、
R15は、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルキル又はC1~C6アルコキシを表し、
Raは、C1~C6アルキルを表し、
Ra1は、C1~C6アルキル、フェニル又は(Z1)mによって置換されたフェニルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、または互いに相異なっても良く、
Z1は、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、または互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、シアノ、C1~C6アルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル又は-CH2CNを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を表し、p5が2、3、4又は5の整数を表し、p7が2、3、4、5、6又は7の整数を表す場合には、各々のZ9は互いに同一であっても、または互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、または互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表される、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [67]
R 1 represents a hydrogen atom or C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 3 represents phenyl, phenyl substituted by (Z) m1 , F-31 or F-34;
R 4 represents —C≡C—R 7 , C 1 to C 6 alkyl substituted by R 15 or L-1 to L-4,
R 5 represents C 1 -C 6 alkyl,
R b represents a hydrogen atom,
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to E-90;
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
R 8 is -C(=NOR a )R a1 , -C(=NNR 13 R 14 )R a1 , -C(=NCN)R a1 , phenyl, phenyl substituted by (Z 1 ) m or G- 1 to G-65,
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkyl represents amino, di(C 1 -C 6 alkyl)amino, —C(═NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 10 represents phenyl,
R 11 represents —OH, C 1 -C 6 alkoxy, E-3, E-6, E-7 or E-38;
R 13 represents a hydrogen atom or C 1 -C 6 alkyl,
R 14 represents C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl,
R 15 represents C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkyl or C 1 -C 6 alkoxy,
R a represents C 1 -C 6 alkyl,
R a1 represents C 1 -C 6 alkyl, phenyl or phenyl substituted by (Z 1 ) m ;
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a is cyano, C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl or - represents CH 2 CN,
In relation to Z9, p2 represents an integer of 2, p3 represents an integer of 2 or 3, p4 represents an integer of 2, 3 or 4, and p5 represents an integer of 2, 3, 4 or 5. and when p represents an integer of 2, 3, 4, 5, 6 or 7, each Z 9 may be the same as or different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
The thienouracil compound or a salt thereof according to [1] above.
R1は、水素原子又はC1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R3は、フェニル、(Z)m1によって置換されたフェニル、F-31又はF-34を表し、
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又は、L-1~L-4を表し、
R5は、C1~C6アルキルを表し、
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、R16によって置換されたC3~C6シクロアルキル又はE-1~E-90を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
R8は、-C(=NORa)Ra1、-C(=NNR13R14)Ra1、-C(=NCN)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、C1~C6アルキルアミノ、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル又はG-1~G-65を表し、
R10は、フェニルを表し、
R11は、-OH、C1~C6アルコキシ、E-3、E-6、E-7又はE-38を表し、
R13は、水素原子又はC1~C6アルキルを表し、
R14は、C1~C6アルキル又はC1~C6アルキルカルボニルを表し、
R15は、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルキル又はC1~C6アルコキシを表し、
Raは、C1~C6アルキルを表し、
Ra1は、C1~C6アルキル、フェニル又は(Z1)mによって置換されたフェニルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、または互いに相異なっても良く、
Z1は、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、または互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、シアノ、C1~C6アルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル又は-CH2CNを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を表し、p5が2、3、4又は5の整数を表し、p7が2、3、4、5、6又は7の整数を表す場合には、各々のZ9は互いに同一であっても、または互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、または互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表される、上記〔1〕に記載のチエノウラシル化合物又はその塩。 [67]
R 1 represents a hydrogen atom or C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 3 represents phenyl, phenyl substituted by (Z) m1 , F-31 or F-34;
R 4 represents —C≡C—R 7 , C 1 to C 6 alkyl substituted by R 15 or L-1 to L-4,
R 5 represents C 1 -C 6 alkyl,
R b represents a hydrogen atom,
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl substituted by R 16 or E-1 to E-90;
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
R 8 is -C(=NOR a )R a1 , -C(=NNR 13 R 14 )R a1 , -C(=NCN)R a1 , phenyl, phenyl substituted by (Z 1 ) m or G- 1 to G-65,
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkyl represents amino, di(C 1 -C 6 alkyl)amino, —C(═NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m or G-1 to G-65;
R 10 represents phenyl,
R 11 represents —OH, C 1 -C 6 alkoxy, E-3, E-6, E-7 or E-38;
R 13 represents a hydrogen atom or C 1 -C 6 alkyl,
R 14 represents C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl,
R 15 represents C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkyl or C 1 -C 6 alkoxy,
R a represents C 1 -C 6 alkyl,
R a1 represents C 1 -C 6 alkyl, phenyl or phenyl substituted by (Z 1 ) m ;
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a is cyano, C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl or - represents CH 2 CN,
In relation to Z9, p2 represents an integer of 2, p3 represents an integer of 2 or 3, p4 represents an integer of 2, 3 or 4, and p5 represents an integer of 2, 3, 4 or 5. and when p represents an integer of 2, 3, 4, 5, 6 or 7, each Z 9 may be the same as or different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
The thienouracil compound or a salt thereof according to [1] above.
〔68〕
R1は、C1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表し、
R3は、(Z)m1によって置換されたフェニルを表し、
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、C1~C6アルキル又はE-38を表し、
R8は、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル、G-3又はG-22を表し、
R9は、C1~C6アルキルカルボニル、フェニル、G-3、G-21又はG-22を表し、
R15は、C1~C6アルコキシを表し、
Ra1は、C1~C6アルキルを表し、
Zは、ハロゲン原子又はC1~C6アルコキシを表し、
Z1は、ハロゲン原子を表す、上記〔67〕に記載のチエノウラシル化合物又はその塩。 [68]
R 1 represents C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 represents
R 3 represents phenyl substituted by (Z) m1 ,
R 4 represents —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents C 1 -C 6 alkyl or E-38;
R 8 represents -C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m , G-3 or G-22;
R 9 represents C 1 -C 6 alkylcarbonyl, phenyl, G-3, G-21 or G-22;
R 15 represents C 1 -C 6 alkoxy,
R a1 represents C 1 -C 6 alkyl,
Z represents a halogen atom or C 1 -C 6 alkoxy;
The thienouracil compound or salt thereof according to [67] above, wherein Z 1 represents a halogen atom.
R1は、C1~C6アルキルを表し、
R2は、水素原子、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表し、
R3は、(Z)m1によって置換されたフェニルを表し、
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、C1~C6アルキル又はE-38を表し、
R8は、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル、G-3又はG-22を表し、
R9は、C1~C6アルキルカルボニル、フェニル、G-3、G-21又はG-22を表し、
R15は、C1~C6アルコキシを表し、
Ra1は、C1~C6アルキルを表し、
Zは、ハロゲン原子又はC1~C6アルコキシを表し、
Z1は、ハロゲン原子を表す、上記〔67〕に記載のチエノウラシル化合物又はその塩。 [68]
R 1 represents C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 represents
R 3 represents phenyl substituted by (Z) m1 ,
R 4 represents —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents C 1 -C 6 alkyl or E-38;
R 8 represents -C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m , G-3 or G-22;
R 9 represents C 1 -C 6 alkylcarbonyl, phenyl, G-3, G-21 or G-22;
R 15 represents C 1 -C 6 alkoxy,
R a1 represents C 1 -C 6 alkyl,
Z represents a halogen atom or C 1 -C 6 alkoxy;
The thienouracil compound or salt thereof according to [67] above, wherein Z 1 represents a halogen atom.
〔69〕
mは、1の整数を表し、
m1は、1又は2の整数を表し、
p2、p3及びp9は、0を表す、上記〔68〕に記載のチエノウラシル化合物又はその塩。 [69]
m represents an integer of 1,
m1 represents an integer of 1 or 2,
The thienouracil compound or salt thereof according to [68] above, wherein p2, p3 and p9 represent 0;
mは、1の整数を表し、
m1は、1又は2の整数を表し、
p2、p3及びp9は、0を表す、上記〔68〕に記載のチエノウラシル化合物又はその塩。 [69]
m represents an integer of 1,
m1 represents an integer of 1 or 2,
The thienouracil compound or salt thereof according to [68] above, wherein p2, p3 and p9 represent 0;
〔70〕
Zはフッ素原子又はメトキシを表す、上記〔68〕又は〔69〕に記載のチエノウラシル化合物又はその塩。 [70]
The thienouracil compound or salt thereof according to [68] or [69] above, wherein Z represents a fluorine atom or methoxy.
Zはフッ素原子又はメトキシを表す、上記〔68〕又は〔69〕に記載のチエノウラシル化合物又はその塩。 [70]
The thienouracil compound or salt thereof according to [68] or [69] above, wherein Z represents a fluorine atom or methoxy.
〔71〕
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、農薬。 [71]
An agricultural chemical containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of [1] to [70] above.
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、農薬。 [71]
An agricultural chemical containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of [1] to [70] above.
〔72〕
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、殺菌剤。 [72]
A fungicide containing, as an active ingredient, one or more selected from the thienouracil compounds and salts thereof according to any one of [1] to [70] above.
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、殺菌剤。 [72]
A fungicide containing, as an active ingredient, one or more selected from the thienouracil compounds and salts thereof according to any one of [1] to [70] above.
〔73〕
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、農園芸用殺菌剤。 [73]
An agricultural and horticultural fungicide containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of [1] to [70] above.
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、農園芸用殺菌剤。 [73]
An agricultural and horticultural fungicide containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of [1] to [70] above.
〔74〕
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、抗真菌剤。 [74]
An antifungal agent containing, as an active ingredient, one or more selected from the thienouracil compounds and salts thereof according to any one of [1] to [70] above.
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、抗真菌剤。 [74]
An antifungal agent containing, as an active ingredient, one or more selected from the thienouracil compounds and salts thereof according to any one of [1] to [70] above.
〔75〕
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、内部寄生虫防除剤。 [75]
An internal parasite control agent containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of [1] to [70] above.
上記〔1〕乃至〔70〕の何れか1つに記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、内部寄生虫防除剤。 [75]
An internal parasite control agent containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of [1] to [70] above.
以下に、本発明化合物の合成例、試験例を実施例として述べることにより、本発明をさらに詳しく説明するが、本発明はこれらによって限定されるものではない。
The present invention will be described in more detail below by describing synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited by these.
合成例に記載した中圧分取液体クロマトグラフィーは、山善株式会社中圧分取装置;YFLC-Wprep(流速18ml/min、シリカゲル40μmのカラム)を使用した。
For medium-pressure preparative liquid chromatography described in the synthesis examples, Yamazen Co., Ltd. medium-pressure preparative apparatus; YFLC-Wprep (flow rate 18 ml/min, silica gel 40 μm column) was used.
また、以下に記載のプロトン核磁気共鳴スペクトル(以下、1H-NMRと記載する。)のケミカルシフト値は、基準物質としてMe4Si(テトラメチルシラン)を用い、重クロロホルム溶媒中で、300MHz(機種;JNM-ECX300又はJNM-ECP300、JEOL社製)にて測定した。なお、1H-NMRのケミカルシフト値における記号は、下記の意味を表す。
s:シングレット、d:ダブレット、dd:ダブルダブレット、t:トリプレット、q:カルテット、m:マルチプレット、br:ブロードシングレット。 In addition, the chemical shift value of the proton nuclear magnetic resonance spectrum (hereinafter referred to as 1 H-NMR) described below was measured at 300 MHz using Me 4 Si (tetramethylsilane) as a reference substance in a deuterated chloroform solvent. (Model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL). The symbols in the 1 H-NMR chemical shift values have the following meanings.
s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, br: broad singlet.
s:シングレット、d:ダブレット、dd:ダブルダブレット、t:トリプレット、q:カルテット、m:マルチプレット、br:ブロードシングレット。 In addition, the chemical shift value of the proton nuclear magnetic resonance spectrum (hereinafter referred to as 1 H-NMR) described below was measured at 300 MHz using Me 4 Si (tetramethylsilane) as a reference substance in a deuterated chloroform solvent. (Model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL). The symbols in the 1 H-NMR chemical shift values have the following meanings.
s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, br: broad singlet.
[合成例]
合成例1
ターシャリーブチル-(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの製造(化合物No.1-001)
ターシャリーブチル(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメート200mgの1,3-ジメチル-2-イミダゾリジノン3ml溶液に、室温にて炭酸セシウム360mgを添加した。該反応溶液を70℃に昇温し、テトラヒドロ-2H-ピラン-4-イル-4-メチルベンゼンスルホネート190mgの1,3-ジメチル-2-イミダゾリジノン1ml溶液を滴下し、同温度にて5時間撹拌した。反応終了後、該反応混合物に水20mlを添加し、析出した固体をろ取した。得られた固体をクロロホルム5mlに溶解させ、無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(1:1から1:9へのグラジエント)(数値は体積比、以下同じである。)を使用するシリカゲルカラムクロマトグラフィーで精製し、目的物85mgをオイル状物として得た。 [Synthesis example]
Synthesis example 1
tert-butyl-(6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl) Preparation of oxy)vinyl)-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate (Compound No. 1-001)
Tertiary butyl (6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-methyl-2,4-dioxo- To a solution of 200 mg of 1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate in 3 ml of 1,3-dimethyl-2-imidazolidinone, 360 mg of cesium carbonate was added at room temperature. did. The reaction solution was heated to 70° C., and a solution of 190 mg of tetrahydro-2H-pyran-4-yl-4-methylbenzenesulfonate in 1 ml of 1,3-dimethyl-2-imidazolidinone was added dropwise. Stirred for an hour. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dissolved in 5 ml of chloroform, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as an eluent (numbers are volume ratios, the same applies hereinafter), 85 mg of the desired product was obtained as an oily substance.
合成例1
ターシャリーブチル-(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの製造(化合物No.1-001)
ターシャリーブチル(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメート200mgの1,3-ジメチル-2-イミダゾリジノン3ml溶液に、室温にて炭酸セシウム360mgを添加した。該反応溶液を70℃に昇温し、テトラヒドロ-2H-ピラン-4-イル-4-メチルベンゼンスルホネート190mgの1,3-ジメチル-2-イミダゾリジノン1ml溶液を滴下し、同温度にて5時間撹拌した。反応終了後、該反応混合物に水20mlを添加し、析出した固体をろ取した。得られた固体をクロロホルム5mlに溶解させ、無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(1:1から1:9へのグラジエント)(数値は体積比、以下同じである。)を使用するシリカゲルカラムクロマトグラフィーで精製し、目的物85mgをオイル状物として得た。 [Synthesis example]
Synthesis example 1
tert-butyl-(6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl) Preparation of oxy)vinyl)-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate (Compound No. 1-001)
Tertiary butyl (6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-methyl-2,4-dioxo- To a solution of 200 mg of 1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate in 3 ml of 1,3-dimethyl-2-imidazolidinone, 360 mg of cesium carbonate was added at room temperature. did. The reaction solution was heated to 70° C., and a solution of 190 mg of tetrahydro-2H-pyran-4-yl-4-methylbenzenesulfonate in 1 ml of 1,3-dimethyl-2-imidazolidinone was added dropwise. Stirred for an hour. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dissolved in 5 ml of chloroform, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as an eluent (numbers are volume ratios, the same applies hereinafter), 85 mg of the desired product was obtained as an oily substance.
合成例2
N-(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)-N-メチルチオフェン-2-カルボキサミドの製造(化合物No.1-005)
6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン140mgのジクロロメタン2ml溶液にトリエチルアミン105mg、チオフェン-2-カルボニルクロリド76mgを順次添加し、室温にて20時間撹拌した。反応終了後、該反応混合物に水5mlを添加し、クロロホルム(5ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(1:1から1:9へのグラジエント)を使用するシリカゲルカラムクロマトグラフィーで精製し、目的物80mgを淡黄色固体として得た。
融点:206~209℃。 Synthesis example 2
N-(6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy) Preparation of vinyl)-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)-N-methylthiophene-2-carboxamide (Compound No. 1 -005)
6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)- 105 mg of triethylamine and 76 mg of thiophene-2-carbonyl chloride were sequentially added to a solution of 140 mg of 5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione in 2 ml of dichloromethane. at room temperature for 20 hours. After completion of the reaction, 5 ml of water was added to the reaction mixture and extracted with chloroform (5 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as an eluent to obtain 80 mg of the desired product as a pale yellow solid.
Melting point: 206-209°C.
N-(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)-N-メチルチオフェン-2-カルボキサミドの製造(化合物No.1-005)
6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン140mgのジクロロメタン2ml溶液にトリエチルアミン105mg、チオフェン-2-カルボニルクロリド76mgを順次添加し、室温にて20時間撹拌した。反応終了後、該反応混合物に水5mlを添加し、クロロホルム(5ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(1:1から1:9へのグラジエント)を使用するシリカゲルカラムクロマトグラフィーで精製し、目的物80mgを淡黄色固体として得た。
融点:206~209℃。 Synthesis example 2
N-(6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy) Preparation of vinyl)-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)-N-methylthiophene-2-carboxamide (Compound No. 1 -005)
6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)- 105 mg of triethylamine and 76 mg of thiophene-2-carbonyl chloride were sequentially added to a solution of 140 mg of 5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione in 2 ml of dichloromethane. at room temperature for 20 hours. After completion of the reaction, 5 ml of water was added to the reaction mixture and extracted with chloroform (5 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as an eluent to obtain 80 mg of the desired product as a pale yellow solid.
Melting point: 206-209°C.
合成例3
6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチル(3-メチル-2-ブテン-1-イル)アミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの製造(化合物No.1-007)
6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン120mgのプロピオニトリル3ml溶液に炭酸カリウム127mg及び1-ブロモ-3-メチル-2-ブテン102mgを順次添加し、溶媒が還流する温度にて15時間撹拌した。反応終了後、該反応混合物の溶媒を減圧下留去し、水5mlを添加し、クロロホルム(5ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(1:1から1:9へのグラジエント)を使用するシリカゲルカラムクロマトグラフィーで精製した。得られた粗物をジイソプロピルエーテル1mlで洗浄し、目的物50mgを白色固体として得た。
融点:173~175℃。 Synthesis example 3
6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)- Preparation of 5-methyl-3-(methyl(3-methyl-2-buten-1-yl)amino)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (Compound No. 1 -007)
6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)- A solution of 120 mg of 5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione in 3 ml of propionitrile was added with 127 mg of potassium carbonate and 1-bromo-3-methyl- 102 mg of 2-butene was sequentially added and stirred for 15 hours at a temperature at which the solvent was refluxed. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure, 5 ml of water was added, and the mixture was extracted with chloroform (5 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as eluent. The resulting crude product was washed with 1 ml of diisopropyl ether to obtain 50 mg of the desired product as a white solid.
Melting point: 173-175°C.
6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチル(3-メチル-2-ブテン-1-イル)アミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの製造(化合物No.1-007)
6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン120mgのプロピオニトリル3ml溶液に炭酸カリウム127mg及び1-ブロモ-3-メチル-2-ブテン102mgを順次添加し、溶媒が還流する温度にて15時間撹拌した。反応終了後、該反応混合物の溶媒を減圧下留去し、水5mlを添加し、クロロホルム(5ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(1:1から1:9へのグラジエント)を使用するシリカゲルカラムクロマトグラフィーで精製した。得られた粗物をジイソプロピルエーテル1mlで洗浄し、目的物50mgを白色固体として得た。
融点:173~175℃。 Synthesis example 3
6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)- Preparation of 5-methyl-3-(methyl(3-methyl-2-buten-1-yl)amino)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (Compound No. 1 -007)
6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)- A solution of 120 mg of 5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione in 3 ml of propionitrile was added with 127 mg of potassium carbonate and 1-bromo-3-methyl- 102 mg of 2-butene was sequentially added and stirred for 15 hours at a temperature at which the solvent was refluxed. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure, 5 ml of water was added, and the mixture was extracted with chloroform (5 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as eluent. The resulting crude product was washed with 1 ml of diisopropyl ether to obtain 50 mg of the desired product as a white solid.
Melting point: 173-175°C.
合成例4
1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)-6-(1-プロピン-1-イル)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの製造(化合物No.2-017)
6-ブロモ-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン4.1gのN,N-ジメチルホルムアミド25ml溶液に、4,5’-ビス(ジフェニルホスフィノ)-9,9’-ジメチルキサンテン426mg、1-(トリメチルシリル)-1-プロピン1.0g、ヨウ化銅(1価)93mg、酢酸パラジウム(2価)115mg及びテトラブチルアンモニウムフルオリド1水和物5.94gを順次添加し、窒素雰囲気下70℃にて5時間撹拌した。反応終了後、該反応混合物に水250mlを添加し、酢酸エチル(250ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液として酢酸エチルを使用するシリカゲルカラムクロマトグラフィーで精製した。得られた粗物をメタノール20mlで洗浄し、目的物2.06gを褐色固体として得た。
融点:54~56℃。 Synthesis example 4
1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)-6-(1 -propyn-1-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione preparation (Compound No. 2-017)
6-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)thieno 4,5′-Bis(diphenylphosphino)-9,9′- 426 mg of dimethylxanthene, 1.0 g of 1-(trimethylsilyl)-1-propyne, 93 mg of copper iodide (monovalent), 115 mg of palladium acetate (divalent) and 5.94 g of tetrabutylammonium fluoride monohydrate were sequentially added. , under a nitrogen atmosphere at 70° C. for 5 hours. After completion of the reaction, 250 ml of water was added to the reaction mixture and extracted with ethyl acetate (250 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as eluent. The resulting crude product was washed with 20 ml of methanol to obtain 2.06 g of the desired product as a brown solid.
Melting point: 54-56°C.
1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)-6-(1-プロピン-1-イル)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの製造(化合物No.2-017)
6-ブロモ-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン4.1gのN,N-ジメチルホルムアミド25ml溶液に、4,5’-ビス(ジフェニルホスフィノ)-9,9’-ジメチルキサンテン426mg、1-(トリメチルシリル)-1-プロピン1.0g、ヨウ化銅(1価)93mg、酢酸パラジウム(2価)115mg及びテトラブチルアンモニウムフルオリド1水和物5.94gを順次添加し、窒素雰囲気下70℃にて5時間撹拌した。反応終了後、該反応混合物に水250mlを添加し、酢酸エチル(250ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、溶離液として酢酸エチルを使用するシリカゲルカラムクロマトグラフィーで精製した。得られた粗物をメタノール20mlで洗浄し、目的物2.06gを褐色固体として得た。
融点:54~56℃。 Synthesis example 4
1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)-6-(1 -propyn-1-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione preparation (Compound No. 2-017)
6-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)thieno 4,5′-Bis(diphenylphosphino)-9,9′- 426 mg of dimethylxanthene, 1.0 g of 1-(trimethylsilyl)-1-propyne, 93 mg of copper iodide (monovalent), 115 mg of palladium acetate (divalent) and 5.94 g of tetrabutylammonium fluoride monohydrate were sequentially added. , under a nitrogen atmosphere at 70° C. for 5 hours. After completion of the reaction, 250 ml of water was added to the reaction mixture and extracted with ethyl acetate (250 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as eluent. The resulting crude product was washed with 20 ml of methanol to obtain 2.06 g of the desired product as a brown solid.
Melting point: 54-56°C.
合成例5
6-エチニル-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの製造(化合物No.2-016)
1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)-6-((トリメチルシリル)エチニル)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン67mgのテトラヒドロフラン1ml及びメタノール1ml溶液に、炭酸カリウム18mgを添加し、室温にて1時間撹拌した。反応終了後、該反応混合物に水10mlを添加し、ジクロロメタン(20ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物55mgを褐色オイル状物として得た。 Synthesis example 5
6-ethynyl-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)thieno Preparation of [2,3-d]pyrimidine-2,4(1H,3H)-dione (Compound No. 2-016)
1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)-6-(( To a solution of 67 mg of trimethylsilyl)ethynyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione in 1 ml of tetrahydrofuran and 1 ml of methanol, 18 mg of potassium carbonate was added and stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with dichloromethane (20 ml×1 time). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 55 mg of the desired product as a brown oil.
6-エチニル-1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの製造(化合物No.2-016)
1-(2-(5-フルオロ-2-メトキシフェニル)-2-((テトラヒドロ-2H-ピラン-4-イル)オキシ)ビニル)-5-メチル-3-(メチルアミノ)-6-((トリメチルシリル)エチニル)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン67mgのテトラヒドロフラン1ml及びメタノール1ml溶液に、炭酸カリウム18mgを添加し、室温にて1時間撹拌した。反応終了後、該反応混合物に水10mlを添加し、ジクロロメタン(20ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物55mgを褐色オイル状物として得た。 Synthesis example 5
6-ethynyl-1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)thieno Preparation of [2,3-d]pyrimidine-2,4(1H,3H)-dione (Compound No. 2-016)
1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)vinyl)-5-methyl-3-(methylamino)-6-(( To a solution of 67 mg of trimethylsilyl)ethynyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione in 1 ml of tetrahydrofuran and 1 ml of methanol, 18 mg of potassium carbonate was added and stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with dichloromethane (20 ml×1 time). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 55 mg of the desired product as a brown oil.
[参考例]
以下に、本発明化合物の製造中間体の製造方法を、参考例として示す。 [Reference example]
A method for producing an intermediate for producing the compound of the present invention is shown below as a reference example.
以下に、本発明化合物の製造中間体の製造方法を、参考例として示す。 [Reference example]
A method for producing an intermediate for producing the compound of the present invention is shown below as a reference example.
参考例1
ターシャリーブチル-メチル(5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)カーバメートの合成
エチル-2-アミノ-4-メチルチオフェン-3-カルボキシレート10.0gのジクロロメタン50ml溶液に、室温にて1,1’-カルボニルジイミダゾール9.6g及びトリエチルアミン7.1gを順次添加した。添加終了後、同温度で15時間攪拌した。反応終了後、該反応溶液に、室温にて2-メチルカルバジン酸ターシャリーブチル8.7gを添加した。添加終了後、同温度で1時間攪拌した。反応終了後、該反応混合物に水100mlを添加し、ジクロロメタン(100ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣にエタノール50mlを添加し、0℃にて20質量%ナトリウムエトキシド(エタノール溶液)27.0gを添加した。添加終了後、室温にて1時間攪拌した。反応終了後、該反応混合物の溶媒を減圧下留去し、得られた残渣に水100mlを添加し、水層をクロロホルム(100ml×1回)で洗浄した。得られた水層に、氷冷下にて35質量%塩酸水溶液をpHが3になるまで添加し、酢酸エチル(200ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、ジイソプロピルエーテル50mlにて洗浄し、目的物15gを白色固体として得た。
融点:177~179℃。 Reference example 1
Synthesis of tertiary-butyl-methyl (5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)carbamate Ethyl-2-amino-4-methylthiophene 9.6 g of 1,1'-carbonyldiimidazole and 7.1 g of triethylamine were sequentially added at room temperature to a solution of 10.0 g of -3-carboxylate in 50 ml of dichloromethane. After the addition was completed, the mixture was stirred at the same temperature for 15 hours. After completion of the reaction, 8.7 g of tert-butyl 2-methylcarbazate was added to the reaction solution at room temperature. After the addition was completed, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, 100 ml of water was added to the reaction mixture and extracted with dichloromethane (100 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 50 ml of ethanol was added to the resulting residue, and 27.0 g of 20% by mass sodium ethoxide (ethanol solution) was added at 0°C. After the addition was completed, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure, 100 ml of water was added to the resulting residue, and the aqueous layer was washed with chloroform (100 ml×1 time). A 35% by mass hydrochloric acid aqueous solution was added to the resulting aqueous layer under ice-cooling until the pH reached 3, and the mixture was extracted with ethyl acetate (200 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was washed with 50 ml of diisopropyl ether to obtain 15 g of the desired product as a white solid.
Melting point: 177-179°C.
ターシャリーブチル-メチル(5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)カーバメートの合成
エチル-2-アミノ-4-メチルチオフェン-3-カルボキシレート10.0gのジクロロメタン50ml溶液に、室温にて1,1’-カルボニルジイミダゾール9.6g及びトリエチルアミン7.1gを順次添加した。添加終了後、同温度で15時間攪拌した。反応終了後、該反応溶液に、室温にて2-メチルカルバジン酸ターシャリーブチル8.7gを添加した。添加終了後、同温度で1時間攪拌した。反応終了後、該反応混合物に水100mlを添加し、ジクロロメタン(100ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣にエタノール50mlを添加し、0℃にて20質量%ナトリウムエトキシド(エタノール溶液)27.0gを添加した。添加終了後、室温にて1時間攪拌した。反応終了後、該反応混合物の溶媒を減圧下留去し、得られた残渣に水100mlを添加し、水層をクロロホルム(100ml×1回)で洗浄した。得られた水層に、氷冷下にて35質量%塩酸水溶液をpHが3になるまで添加し、酢酸エチル(200ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、ジイソプロピルエーテル50mlにて洗浄し、目的物15gを白色固体として得た。
融点:177~179℃。 Reference example 1
Synthesis of tertiary-butyl-methyl (5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)carbamate Ethyl-2-amino-4-methylthiophene 9.6 g of 1,1'-carbonyldiimidazole and 7.1 g of triethylamine were sequentially added at room temperature to a solution of 10.0 g of -3-carboxylate in 50 ml of dichloromethane. After the addition was completed, the mixture was stirred at the same temperature for 15 hours. After completion of the reaction, 8.7 g of tert-butyl 2-methylcarbazate was added to the reaction solution at room temperature. After the addition was completed, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, 100 ml of water was added to the reaction mixture and extracted with dichloromethane (100 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 50 ml of ethanol was added to the resulting residue, and 27.0 g of 20% by mass sodium ethoxide (ethanol solution) was added at 0°C. After the addition was completed, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure, 100 ml of water was added to the resulting residue, and the aqueous layer was washed with chloroform (100 ml×1 time). A 35% by mass hydrochloric acid aqueous solution was added to the resulting aqueous layer under ice-cooling until the pH reached 3, and the mixture was extracted with ethyl acetate (200 ml×1 time). The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was washed with 50 ml of diisopropyl ether to obtain 15 g of the desired product as a white solid.
Melting point: 177-179°C.
参考例2
ターシャリーブチル-(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの合成
ターシャリーブチル(6-(4,5-ジヒドロオキサゾール-2-イル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメート2.7gのアセトニトリル15ml溶液に、2-ブロモ-1-(5-フルオロ-2-メトキシフェニル)エタン-1-オン2.1g及び炭酸カリウム1.1gを順次添加し、溶媒が還流する温度で6時間撹拌した。反応終了後、該反応混合物の溶媒を減圧下留去し、得られた残渣に水10mlを添加し、クロロホルム(20ml×1回)にて抽出した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(8:2から1:9へのグラジエント)を使用するシリカゲルカラムクロマトグラフィーで精製し、目的物2.5gを白色固体として得た。
融点:171~173℃。 Reference example 2
tert-butyl-(6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-methyl-2,4-dioxo Synthesis of 1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate Tert-butyl (6-(4,5-dihydrooxazol-2-yl)-5-methyl -2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate 2.7 g of 2-bromo-1-(5- 2.1 g of fluoro-2-methoxyphenyl)ethan-1-one and 1.1 g of potassium carbonate were sequentially added and stirred for 6 hours at the temperature at which the solvent was refluxed. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure, 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (20 ml×1 time). The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 8:2 to 1:9) as an eluent to give 2.5 g of the desired product as a white solid.
Melting point: 171-173°C.
ターシャリーブチル-(6-(4,5-ジヒドロオキサゾール-2-イル)-1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの合成
ターシャリーブチル(6-(4,5-ジヒドロオキサゾール-2-イル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメート2.7gのアセトニトリル15ml溶液に、2-ブロモ-1-(5-フルオロ-2-メトキシフェニル)エタン-1-オン2.1g及び炭酸カリウム1.1gを順次添加し、溶媒が還流する温度で6時間撹拌した。反応終了後、該反応混合物の溶媒を減圧下留去し、得られた残渣に水10mlを添加し、クロロホルム(20ml×1回)にて抽出した。得られた残渣を、溶離液としてn-ヘキサン:酢酸エチル(8:2から1:9へのグラジエント)を使用するシリカゲルカラムクロマトグラフィーで精製し、目的物2.5gを白色固体として得た。
融点:171~173℃。 Reference example 2
tert-butyl-(6-(4,5-dihydrooxazol-2-yl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-methyl-2,4-dioxo Synthesis of 1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate Tert-butyl (6-(4,5-dihydrooxazol-2-yl)-5-methyl -2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate 2.7 g of 2-bromo-1-(5- 2.1 g of fluoro-2-methoxyphenyl)ethan-1-one and 1.1 g of potassium carbonate were sequentially added and stirred for 6 hours at the temperature at which the solvent was refluxed. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure, 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (20 ml×1 time). The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 8:2 to 1:9) as an eluent to give 2.5 g of the desired product as a white solid.
Melting point: 171-173°C.
参考例3
ターシャリーブチル-(6-ブロモ-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの合成
ターシャリーブチル-メチル(5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)カーバメート3gの酢酸20ml溶液に酢酸ナトリウム3水和物2.9g及び臭素1.7gを順次添加し、室温にて1時間反応させた。反応終了後、該反応混合物に水100mlを添加し、析出した固体をろ取した。得られた固体を酢酸エチル30mlに溶解させ、飽和食塩水30mlで洗浄した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、ノルマルヘキサン10ml及びジイソプロピルエーテル10mlにて洗浄し、目的物3.2gを白色固体として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) δ10.60(br, 1H), 3.35-3.15(m, 3H), 3.29&2.34(s, 3H), 1.57(s, 9H)。 Reference example 3
Synthesis of tert-butyl-(6-bromo-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate 2.9 g of sodium acetate trihydrate and 2.9 g of sodium acetate trihydrate in 20 ml of acetic acid 1.7 g of bromine was sequentially added and reacted at room temperature for 1 hour. After completion of the reaction, 100 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dissolved in 30 ml of ethyl acetate and washed with 30 ml of saturated brine. The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was washed with 10 ml of normal hexane and 10 ml of diisopropyl ether to obtain 3.2 g of the desired product as a white solid.
< 1 >H-NMR ( CDCl3 , Me4Si , 300MHz) [delta] 10.60 (br, 1H), 3.35-3.15 (m, 3H), 3.29&2.34 (s, 3H), 1.57 (s, 9H).
ターシャリーブチル-(6-ブロモ-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの合成
ターシャリーブチル-メチル(5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)カーバメート3gの酢酸20ml溶液に酢酸ナトリウム3水和物2.9g及び臭素1.7gを順次添加し、室温にて1時間反応させた。反応終了後、該反応混合物に水100mlを添加し、析出した固体をろ取した。得られた固体を酢酸エチル30mlに溶解させ、飽和食塩水30mlで洗浄した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、ノルマルヘキサン10ml及びジイソプロピルエーテル10mlにて洗浄し、目的物3.2gを白色固体として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) δ10.60(br, 1H), 3.35-3.15(m, 3H), 3.29&2.34(s, 3H), 1.57(s, 9H)。 Reference example 3
Synthesis of tert-butyl-(6-bromo-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)(methyl)carbamate 2.9 g of sodium acetate trihydrate and 2.9 g of sodium acetate trihydrate in 20 ml of acetic acid 1.7 g of bromine was sequentially added and reacted at room temperature for 1 hour. After completion of the reaction, 100 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dissolved in 30 ml of ethyl acetate and washed with 30 ml of saturated brine. The obtained organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was washed with 10 ml of normal hexane and 10 ml of diisopropyl ether to obtain 3.2 g of the desired product as a white solid.
< 1 >H-NMR ( CDCl3 , Me4Si , 300MHz) [delta] 10.60 (br, 1H), 3.35-3.15 (m, 3H), 3.29&2.34 (s, 3H), 1.57 (s, 9H).
参考例4
3-((ターシャリーブトキシカルボニル)(メチル)アミノ)-5-メチル-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボン酸の合成
エチル-3-((ターシャリーブトキシカルボニル)(メチル)アミノ)-5-メチル-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキシレート630mgのエタノール15ml溶液に、室温にて1mol/l水酸化ナトリウム水溶液4.9mlを添加し、75℃にて3時間攪拌した。反応終了後、該反応混合物の溶媒を減圧下にて留去した。得られた残渣に氷冷下にて1mol/l塩酸水溶液10mlを添加し、析出した固体をろ取した。得られた固体を減圧下にて乾燥し、目的物560mgを紫色固体として得た。
融点:230℃~232℃。 Reference example 4
Synthesis of 3-((tert-butoxycarbonyl)(methyl)amino)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylic acid Ethyl-3-((tertiary-butoxycarbonyl)(methyl)amino)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate To a solution of 630 mg in 15 ml of ethanol, 4.9 ml of 1 mol/l sodium hydroxide aqueous solution was added at room temperature, and the mixture was stirred at 75° C. for 3 hours. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure. 10 ml of a 1 mol/l hydrochloric acid aqueous solution was added to the resulting residue under ice-cooling, and the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure to obtain 560 mg of the desired product as a purple solid.
Melting point: 230°C-232°C.
3-((ターシャリーブトキシカルボニル)(メチル)アミノ)-5-メチル-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボン酸の合成
エチル-3-((ターシャリーブトキシカルボニル)(メチル)アミノ)-5-メチル-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキシレート630mgのエタノール15ml溶液に、室温にて1mol/l水酸化ナトリウム水溶液4.9mlを添加し、75℃にて3時間攪拌した。反応終了後、該反応混合物の溶媒を減圧下にて留去した。得られた残渣に氷冷下にて1mol/l塩酸水溶液10mlを添加し、析出した固体をろ取した。得られた固体を減圧下にて乾燥し、目的物560mgを紫色固体として得た。
融点:230℃~232℃。 Reference example 4
Synthesis of 3-((tert-butoxycarbonyl)(methyl)amino)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylic acid Ethyl-3-((tertiary-butoxycarbonyl)(methyl)amino)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate To a solution of 630 mg in 15 ml of ethanol, 4.9 ml of 1 mol/l sodium hydroxide aqueous solution was added at room temperature, and the mixture was stirred at 75° C. for 3 hours. After completion of the reaction, the solvent of the reaction mixture was distilled off under reduced pressure. 10 ml of a 1 mol/l hydrochloric acid aqueous solution was added to the resulting residue under ice-cooling, and the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure to obtain 560 mg of the desired product as a purple solid.
Melting point: 230°C-232°C.
参考例5
ターシャリーブチル(6-(4,5-ジヒドロオキサゾール-2-イル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの合成
3-((ターシャリーブトキシカルボニル)(メチル)アミノ)-5-メチル-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボン酸5gのジクロロメタン50ml溶液に、2-ブロモエチルアミン臭素酸塩3.2g、トリエチルアミン4.3g、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミド塩酸塩3.7g及び4-ジメチルアミノピリジン50mgを順次添加し、室温にて15時間撹拌した。反応終了後、該反応混合物に0℃にて3mol/l塩酸水溶液50mlを添加し、得られた溶液を酢酸エチル(100ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物2.6gを褐色樹脂状物として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) δ4.50-4.25(m, 2H), 4.00-3.85(m, 2H), 3.25-3.10(m, 3H), 2.75-2.60(m, 3H), 1.55-1.15(m, 9H)。なお、NHのプロトンは観測されなかった。 Reference example 5
Tertiary butyl (6-(4,5-dihydrooxazol-2-yl)-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl) Synthesis of (methyl) carbamate 3-((tert-butoxycarbonyl)(methyl)amino)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine- In a solution of 5 g of 6-carboxylic acid in 50 ml of dichloromethane, 3.2 g of 2-bromoethylamine bromate, 4.3 g of triethylamine, 3.7 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-dimethyl 50 mg of aminopyridine was sequentially added and stirred at room temperature for 15 hours. After completion of the reaction, 50 ml of 3 mol/l hydrochloric acid aqueous solution was added to the reaction mixture at 0° C., and the obtained solution was extracted with ethyl acetate (100 ml×1 time). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.6 g of the desired product as a brown resinous substance.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) δ4.50-4.25(m, 2H), 4.00-3.85(m, 2H), 3.25-3.10(m, 3H), 2.75-2.60(m, 3H ), 1.55-1.15(m, 9H). NH protons were not observed.
ターシャリーブチル(6-(4,5-ジヒドロオキサゾール-2-イル)-5-メチル-2,4-ジオキソ-1,4-ジヒドロチエノ[2,3-d]ピリミジン-3(2H)-イル)(メチル)カーバメートの合成
3-((ターシャリーブトキシカルボニル)(メチル)アミノ)-5-メチル-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボン酸5gのジクロロメタン50ml溶液に、2-ブロモエチルアミン臭素酸塩3.2g、トリエチルアミン4.3g、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミド塩酸塩3.7g及び4-ジメチルアミノピリジン50mgを順次添加し、室温にて15時間撹拌した。反応終了後、該反応混合物に0℃にて3mol/l塩酸水溶液50mlを添加し、得られた溶液を酢酸エチル(100ml×1回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物2.6gを褐色樹脂状物として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) δ4.50-4.25(m, 2H), 4.00-3.85(m, 2H), 3.25-3.10(m, 3H), 2.75-2.60(m, 3H), 1.55-1.15(m, 9H)。なお、NHのプロトンは観測されなかった。 Reference example 5
Tertiary butyl (6-(4,5-dihydrooxazol-2-yl)-5-methyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl) Synthesis of (methyl) carbamate 3-((tert-butoxycarbonyl)(methyl)amino)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine- In a solution of 5 g of 6-carboxylic acid in 50 ml of dichloromethane, 3.2 g of 2-bromoethylamine bromate, 4.3 g of triethylamine, 3.7 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-dimethyl 50 mg of aminopyridine was sequentially added and stirred at room temperature for 15 hours. After completion of the reaction, 50 ml of 3 mol/l hydrochloric acid aqueous solution was added to the reaction mixture at 0° C., and the obtained solution was extracted with ethyl acetate (100 ml×1 time). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.6 g of the desired product as a brown resinous substance.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) δ4.50-4.25(m, 2H), 4.00-3.85(m, 2H), 3.25-3.10(m, 3H), 2.75-2.60(m, 3H ), 1.55-1.15(m, 9H). NH protons were not observed.
参考例6
1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-6-(メトキシメチル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの合成
1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-6-(ヒドロキシメチル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン800mgのメタノール10ml溶液に、室温にて濃硫酸30mgを添加した。添加終了後、溶媒が還流する温度で1時間攪拌した。反応終了後、減圧下にて溶媒を留去した。得られた残渣に酢酸エチル10mlを加えてろ過した。ろ液に飽和重曹水30mlを加えて、酢酸エチル(10mL×3回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物700mgを樹脂状物として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) δ7.68-7.56 (m, 1H), 7.35-7.22 (m, 1H), 7.05-6.97 (m, 1H), 5.62-5.48 (m, 1H), 5.38-5.19 (m, 2H), 4.56-4.41 (m, 2H), 4.08-3.93 (m, 3H), 3.45-3.30 (m, 3H), 2.86-2.71 (m, 3H), 2.56-2.40 (m, 3H)。 Reference example 6
1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-6-(methoxymethyl)-5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2, Synthesis of 4(1H,3H)-diones 1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-6-(hydroxymethyl)-5-methyl-3-(methylamino)thieno[ To a solution of 800 mg of 2,3-d]pyrimidine-2,4(1H,3H)-dione in 10 ml of methanol was added 30 mg of concentrated sulfuric acid at room temperature. After the addition was completed, the mixture was stirred for 1 hour at a temperature at which the solvent was refluxed. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of ethyl acetate was added to the resulting residue and filtered. 30 ml of saturated sodium bicarbonate water was added to the filtrate, and the mixture was extracted with ethyl acetate (10 mL×3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 700 mg of the desired product as a resinous substance.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) δ7.68-7.56 (m, 1H), 7.35-7.22 (m, 1H), 7.05-6.97 (m, 1H), 5.62-5.48 (m, 1H ), 5.38-5.19 (m, 2H), 4.56-4.41 (m, 2H), 4.08-3.93 (m, 3H), 3.45-3.30 (m, 3H), 2.86-2.71 (m, 3H), 2.56-2.40 (m, 3H).
1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-6-(メトキシメチル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオンの合成
1-(2-(5-フルオロ-2-メトキシフェニル)-2-オキソエチル)-6-(ヒドロキシメチル)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4(1H,3H)-ジオン800mgのメタノール10ml溶液に、室温にて濃硫酸30mgを添加した。添加終了後、溶媒が還流する温度で1時間攪拌した。反応終了後、減圧下にて溶媒を留去した。得られた残渣に酢酸エチル10mlを加えてろ過した。ろ液に飽和重曹水30mlを加えて、酢酸エチル(10mL×3回)にて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物700mgを樹脂状物として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) δ7.68-7.56 (m, 1H), 7.35-7.22 (m, 1H), 7.05-6.97 (m, 1H), 5.62-5.48 (m, 1H), 5.38-5.19 (m, 2H), 4.56-4.41 (m, 2H), 4.08-3.93 (m, 3H), 3.45-3.30 (m, 3H), 2.86-2.71 (m, 3H), 2.56-2.40 (m, 3H)。 Reference example 6
1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-6-(methoxymethyl)-5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2, Synthesis of 4(1H,3H)-diones 1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-6-(hydroxymethyl)-5-methyl-3-(methylamino)thieno[ To a solution of 800 mg of 2,3-d]pyrimidine-2,4(1H,3H)-dione in 10 ml of methanol was added 30 mg of concentrated sulfuric acid at room temperature. After the addition was completed, the mixture was stirred for 1 hour at a temperature at which the solvent was refluxed. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of ethyl acetate was added to the resulting residue and filtered. 30 ml of saturated sodium bicarbonate water was added to the filtrate, and the mixture was extracted with ethyl acetate (10 mL×3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 700 mg of the desired product as a resinous substance.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) δ7.68-7.56 (m, 1H), 7.35-7.22 (m, 1H), 7.05-6.97 (m, 1H), 5.62-5.48 (m, 1H ), 5.38-5.19 (m, 2H), 4.56-4.41 (m, 2H), 4.08-3.93 (m, 3H), 3.45-3.30 (m, 3H), 2.86-2.71 (m, 3H), 2.56-2.40 (m, 3H).
参考例7
1-(2-(3-クロロフェニル)-2-オキソエチル)-N-(2-メルカプトエチル)-5-メチル-3-(メチルアミノ)-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキサミドの合成
N-(2-クロロエチル)-1-(2-(3-クロロフェニル)-2-オキソエチル)-5-メチル-3-(メチルアミノ)-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキサミド360mgのエタノール5ml溶液に、室温にてチオ尿素117mgを添加し、80℃にて8時間撹拌した。反応終了後、0℃にて50質量%水酸化カリウム水溶液345mgを該反応混合物に添加し、同温度にて1時間撹拌した。反応終了後、同温度にて0.5mol/L塩酸水溶液を添加し、析出した固体をろ取し、目的物310mgを白色固体として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) 7.98-7.94 (m, 1H), 7.90-7.85 (m, 1H), 7.69-7.64 (m, 1H), 7.55-7.47 (m, 1H), 6.37-6.28 (m, 1H), 5.47-5.40 (m, 1H), 5.38 (s, 2H), 3.66-3.57 (m, 2H), 2.89-2.72 (m, 3H), 2.88 (s, 3H), 2.80 (s, 3H)。 Reference example 7
1-(2-(3-chlorophenyl)-2-oxoethyl)-N-(2-mercaptoethyl)-5-methyl-3-(methylamino)-2,4-dioxo-1,2,3,4- Synthesis of Tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide N-(2-chloroethyl)-1-(2-(3-chlorophenyl)-2-oxoethyl)-5-methyl-3-(methylamino) 117 mg of thiourea was added to a solution of 360 mg of -2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide in 5 ml of ethanol at room temperature. Stirred for 8 hours. After completion of the reaction, 345 mg of 50% by mass potassium hydroxide aqueous solution was added to the reaction mixture at 0° C., and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, a 0.5 mol/L hydrochloric acid aqueous solution was added at the same temperature, and the precipitated solid was collected by filtration to obtain 310 mg of the desired product as a white solid.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) 7.98-7.94 (m, 1H), 7.90-7.85 (m, 1H), 7.69-7.64 (m, 1H), 7.55-7.47 (m, 1H), 6.37-6.28 (m, 1H), 5.47-5.40 (m, 1H), 5.38 (s, 2H), 3.66-3.57 (m, 2H), 2.89-2.72 (m, 3H), 2.88 (s, 3H), 2.80 (s, 3H).
1-(2-(3-クロロフェニル)-2-オキソエチル)-N-(2-メルカプトエチル)-5-メチル-3-(メチルアミノ)-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキサミドの合成
N-(2-クロロエチル)-1-(2-(3-クロロフェニル)-2-オキソエチル)-5-メチル-3-(メチルアミノ)-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキサミド360mgのエタノール5ml溶液に、室温にてチオ尿素117mgを添加し、80℃にて8時間撹拌した。反応終了後、0℃にて50質量%水酸化カリウム水溶液345mgを該反応混合物に添加し、同温度にて1時間撹拌した。反応終了後、同温度にて0.5mol/L塩酸水溶液を添加し、析出した固体をろ取し、目的物310mgを白色固体として得た。
1H-NMR (CDCl3, Me4Si, 300MHz) 7.98-7.94 (m, 1H), 7.90-7.85 (m, 1H), 7.69-7.64 (m, 1H), 7.55-7.47 (m, 1H), 6.37-6.28 (m, 1H), 5.47-5.40 (m, 1H), 5.38 (s, 2H), 3.66-3.57 (m, 2H), 2.89-2.72 (m, 3H), 2.88 (s, 3H), 2.80 (s, 3H)。 Reference example 7
1-(2-(3-chlorophenyl)-2-oxoethyl)-N-(2-mercaptoethyl)-5-methyl-3-(methylamino)-2,4-dioxo-1,2,3,4- Synthesis of Tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide N-(2-chloroethyl)-1-(2-(3-chlorophenyl)-2-oxoethyl)-5-methyl-3-(methylamino) 117 mg of thiourea was added to a solution of 360 mg of -2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide in 5 ml of ethanol at room temperature. Stirred for 8 hours. After completion of the reaction, 345 mg of 50% by mass potassium hydroxide aqueous solution was added to the reaction mixture at 0° C., and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, a 0.5 mol/L hydrochloric acid aqueous solution was added at the same temperature, and the precipitated solid was collected by filtration to obtain 310 mg of the desired product as a white solid.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) 7.98-7.94 (m, 1H), 7.90-7.85 (m, 1H), 7.69-7.64 (m, 1H), 7.55-7.47 (m, 1H), 6.37-6.28 (m, 1H), 5.47-5.40 (m, 1H), 5.38 (s, 2H), 3.66-3.57 (m, 2H), 2.89-2.72 (m, 3H), 2.88 (s, 3H), 2.80 (s, 3H).
参考例8
1-(2-(3-クロロフェニル)-2-オキソエチル)-6-(4,5-ジヒドロチアゾール-2yl)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4-(1H,3H)-ジオンの合成
1-(2-(3-クロロフェニル)-2-オキソエチル)-N-(2-メルカプトエチル)-5-メチル-3-(メチルアミノ)-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキサミド260mgのトルエン50ml溶液に、室温にてパラトルエンスルホン酸1水和物215mgを添加し、ディーンスターク還流管を用い、溶媒が還流する温度にて17時間撹拌した。反応終了後、該反応混合物に水50mlを添加し、酢酸エチルにて抽出(20ml×3回)した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物160mgを褐色オイル状物として得た。
1H-NMR (CDCl3, Me4Si, 300MHz)δ7.98-7.84 (m, 2H), 7.67-7.45 (m, 2H), 6.57-6.35 (m, 1H), 5.38 (s, 2H), 4.28-4.20 (m, 2H), 3.47-3.40 (m, 2H), 2.86 (s, 3H), 2.79 (s, 3H)。 Reference example 8
1-(2-(3-chlorophenyl)-2-oxoethyl)-6-(4,5-dihydrothiazole-2yl)-5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2 ,4-(1H,3H)-dione synthesis 1-(2-(3-chlorophenyl)-2-oxoethyl)-N-(2-mercaptoethyl)-5-methyl-3-(methylamino)-2, To a solution of 260 mg of 4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide in 50 ml of toluene, 215 mg of p-toluenesulfonic acid monohydrate was added at room temperature. Using a Stark reflux tube, the mixture was stirred for 17 hours at a temperature at which the solvent was refluxed. After completion of the reaction, 50 ml of water was added to the reaction mixture and extracted with ethyl acetate (20 ml×3 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 160 mg of the desired product as a brown oil.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) δ7.98-7.84 (m, 2H), 7.67-7.45 (m, 2H), 6.57-6.35 (m, 1H), 5.38 (s, 2H), 4.28-4.20 (m, 2H), 3.47-3.40 (m, 2H), 2.86 (s, 3H), 2.79 (s, 3H).
1-(2-(3-クロロフェニル)-2-オキソエチル)-6-(4,5-ジヒドロチアゾール-2yl)-5-メチル-3-(メチルアミノ)チエノ[2,3-d]ピリミジン-2,4-(1H,3H)-ジオンの合成
1-(2-(3-クロロフェニル)-2-オキソエチル)-N-(2-メルカプトエチル)-5-メチル-3-(メチルアミノ)-2,4-ジオキソ-1,2,3,4-テトラヒドロチエノ[2,3-d]ピリミジン-6-カルボキサミド260mgのトルエン50ml溶液に、室温にてパラトルエンスルホン酸1水和物215mgを添加し、ディーンスターク還流管を用い、溶媒が還流する温度にて17時間撹拌した。反応終了後、該反応混合物に水50mlを添加し、酢酸エチルにて抽出(20ml×3回)した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去し、目的物160mgを褐色オイル状物として得た。
1H-NMR (CDCl3, Me4Si, 300MHz)δ7.98-7.84 (m, 2H), 7.67-7.45 (m, 2H), 6.57-6.35 (m, 1H), 5.38 (s, 2H), 4.28-4.20 (m, 2H), 3.47-3.40 (m, 2H), 2.86 (s, 3H), 2.79 (s, 3H)。 Reference example 8
1-(2-(3-chlorophenyl)-2-oxoethyl)-6-(4,5-dihydrothiazole-2yl)-5-methyl-3-(methylamino)thieno[2,3-d]pyrimidine-2 ,4-(1H,3H)-dione synthesis 1-(2-(3-chlorophenyl)-2-oxoethyl)-N-(2-mercaptoethyl)-5-methyl-3-(methylamino)-2, To a solution of 260 mg of 4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxamide in 50 ml of toluene, 215 mg of p-toluenesulfonic acid monohydrate was added at room temperature. Using a Stark reflux tube, the mixture was stirred for 17 hours at a temperature at which the solvent was refluxed. After completion of the reaction, 50 ml of water was added to the reaction mixture and extracted with ethyl acetate (20 ml×3 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 160 mg of the desired product as a brown oil.
1 H-NMR (CDCl 3 , Me 4 Si, 300MHz) δ7.98-7.84 (m, 2H), 7.67-7.45 (m, 2H), 6.57-6.35 (m, 1H), 5.38 (s, 2H), 4.28-4.20 (m, 2H), 3.47-3.40 (m, 2H), 2.86 (s, 3H), 2.79 (s, 3H).
本発明化合物は、前記製造例及び合成例に準じて合成することができる。合成例1~合成例5と同様に製造した、本発明化合物の例を、第3表~第6表に示すが、本発明化合物はこれらのみに限定されるものではない。また、第3表~第6表に記載の全ての合成化合物については、国際公開第2021/149771号の合成例1の構造解析の結果を元に、第3表~第6表に記載の立体配置を有する単一の幾何異性体が得られたと推定した。
The compound of the present invention can be synthesized according to the above Production Examples and Synthesis Examples. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 5 are shown in Tables 3 to 6, but the compounds of the present invention are not limited to these. In addition, for all synthetic compounds described in Tables 3 to 6, based on the results of structural analysis of Synthesis Example 1 of International Publication No. 2021/149771, the stereoscopic compounds described in Tables 3 to 6 A single geometric isomer with configuration was assumed to be obtained.
表中、Meはメチルを、Etはエチルを、nPrはノルマルプロピルを、iPrはイソプロピルを、cPrはシクロプロピルを、iBuはイソブチルを、sBuはセカンダリーブチルを、tBuはターシャリーブチルを、nPenはノルマルペンチルを、cPenはシクロペンチルを、cHexはシクロヘキシルを、Phはフェニルを、=は2重結合を、≡は3重結合をそれぞれ表す。また、「*」の表記は、化合物が融点のない油状物又は樹脂状の化合物であることを表し、「m.p.」は融点(単位は℃)を表す。
In the table, Me is methyl, Et is ethyl, nPr is normal propyl, iPr is isopropyl, cPr is cyclopropyl, iBu is isobutyl, sBu is secondary butyl, tBu is tertiary butyl, and nPen is n-pentyl, cPen for cyclopentyl, cHex for cyclohexyl, Ph for phenyl, = for a double bond, and ≡ for a triple bond. The notation "*" indicates that the compound is an oily or resinous compound with no melting point, and "mp" indicates the melting point (unit: °C).
また表中、(E)及び(Z)の記載は、幾何異性体の混合比において、それぞれ(E)-体及び(Z)-体が90%以上であることを表す。
In the table, the descriptions of (E) and (Z) represent that the (E)-isomer and (Z)-isomer are 90% or more, respectively, in the mixing ratio of the geometric isomers.
また表中、(Z)m1の置換位置を表す番号は、それぞれ下記の構造式において記された番号に対応するものである。
In the table, the numbers representing the substitution positions of (Z) m1 correspond to the numbers described in the following structural formulas.
また表中、例えば「Ph-4-Me」中の「4-」の記載は、下記に記載の通りフェニル基上の置換位置を表す。例えば「Ph-4-Me」は4-メチルフェニルを表し、「Ph-2,6-F2」は2、6-ジフルオロフェニルを表す。
In the table, the description of "4-" in "Ph-4-Me", for example, represents the substitution position on the phenyl group as described below. For example, "Ph-4-Me" represents 4-methylphenyl and "Ph-2,6-F 2 " represents 2,6-difluorophenyl.
また、G-1a、G-3a、G-4a、G-15a、G-16a、G-17a、G-21a、G-22a、G-23a、G-52a、G-53a、E-38a、E-41a、E-44a、E-45a及びE-76aで表される置換基は、それぞれ下記の構造を表す。
In addition, G-1a, G-3a, G-4a, G-15a, G-16a, G-17a, G-21a, G-22a, G-23a, G-52a, G-53a, E-38a, The substituents represented by E-41a, E-44a, E-45a and E-76a each represent the following structures.
また、L-2、L-3、L-4、L-5a、L-5b、L-5c、L-6a及びL-7aで表される置換基は、それぞれ下記の構造を表す。
Further, the substituents represented by L-2, L-3, L-4, L-5a, L-5b, L-5c, L-6a and L-7a each represent the following structures.
なお、上記のG-1a、G-3a、G-4a、G-15a、G-16a、G-17a、G-21a、G-22a、G-23a、G-52a、G-53a、E-44a及びL-7aの構造式において記された番号は置換基を有する場合の置換位置を表す番号であり、例えば、表中「(G-3a)-3-Me」の記載は、以下の構造を表す。置換基の記載がないものは無置換であることを表す。
In addition, the above G-1a, G-3a, G-4a, G-15a, G-16a, G-17a, G-21a, G-22a, G-23a, G-52a, G-53a, E- The numbers written in the structural formulas of 44a and L-7a are numbers representing the substitution positions when they have substituents. represents Those with no description of substituents represent unsubstituted.
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No. R2 R6 (Z)m1 m.p.(℃)
――――――――――――――――――――――――――――――――――
1-001 C(O)OtBu E-38a 2-OMe-5-F *
1-002 C(O)OtBu iPr 2-OMe-5-F 219-221
1-003 CH2(Ph-2-F) E-38a 2-OMe-5-F 169-171
1-004 H E-38a 2-OMe-5-F 186-188
1-005 C(O)(G-3a) E-38a 2-OMe-5-F 206-209
1-006 C(O)OiBu E-38a 2-OMe-5-F 153-156
1-007 CH2CH=C(Me)2 E-38a 2-OMe-5-F 173-175
1-008 C(O)(G-22a) E-38a 2-OMe-5-F 156-163
1-009 C(O)Ph E-38a 2-OMe-5-F 179-182
1-010 CH2(Ph-2-F) E-38a 3-F 169-171
1-011 CH2(Ph-2-F) E-38a 2-OMe 173-175
1-012 CH2(G-3a) E-38a 2-OMe-5-F 184-186
1-013 CH2(G-3a) E-38a 3-F *
1-014 CH2(G-3a) E-38a 2-OMe *
1-015 CH2C(=NOMe)Me E-38a 2-OMe 187-189
1-016 CH2C(=NOMe)Me E-38a 3-F *
1-017 CH2(Ph-2-F-6-Cl) E-38a 2-OMe *
1-018 CH2(Ph-2-F-6-Cl) E-38a 3-F *
1-019 C(O)Ph E-38a 2-OMe 215-217
1-020 C(O)(G-3a) E-38a 2-OMe 210-212
1-021 C(O)(G-4a) E-38a 2-OMe 204-205
1-022 C(O)Ph E-38a 3-F 112-114
1-023 C(O)(G-3a) E-38a 3-F 197-199
1-024 C(O)(G-4a) E-38a 3-F 211-213
1-025 C(O)(G-22a) E-38a 2-OMe *
1-026 C(O)(G-22a) E-38a 3-F *
1-027 C(O)OiBu E-38a 2-OMe *
1-028 C(O)OiBu E-38a 3-F *
1-029 CH2C(=NOMe)Me CH(Me)C(O)N(H)Me 2-OMe-5-F 203-205
1-030 C(O)OiBu CH(Me)C(O)N(H)Me 2-OMe-5-F 154-156
1-031 CH2C(=NOMe)Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
1-032 CH2(G-3a) CH(Me)C(O)N(H)Me 2-OMe-5-F 153-155
1-033 CH2CH=CHCl CH(Me)C(O)N(H)Me 2-OMe-5-F 117-119
1-034 C(O)(G-3a) CH(Me)C(O)N(H)Me 2-OMe-5-F 194-196
1-035 CH2C(=NOMe)Me E-38a 2-OMe-5-F 71-73
1-036 CH2(G-3a) (E-44a)-1-C(O)OMe 2-OMe-5-F 100-102
1-037 CH2CH=CHCl (E-44a)-1-C(O)OMe 2-OMe-5-F 94-96
1-038 C(O)OiBu (E-44a)-1-C(O)OMe 2-OMe-5-F *
1-039 C(O)(G-22a) (E-44a)-1-C(O)OMe 2-OMe-5-F 140-142
1-040 CH2Ph E-38a H 168-170
1-041 CH2(G-3a) E-38a H 86-88
1-042 CH2C(=NOMe)Me E-38a H *
1-043 CH2CH=CHCl E-38a H 114-116
1-044 CH2Ph (E-44a)-1-C(O)OMe H 177-179
1-045 CH2(G-3a) (E-44a)-1-C(O)OMe H 156-158
1-046 CH2C(=NOMe)Me (E-44a)-1-C(O)OMe H *
1-047 CH2CH=CHCl (E-44a)-1-C(O)OMe H *
1-048 C(O)Ph E-38a H 198-200
1-049 C(O)(G-3a) E-38a H 210-213
1-050 C(O)(G-22a) E-38a H 189-192
1-051 C(O)Ph (E-44a)-1-C(O)OMe H 206-208
1-052 C(O)(G-3a) (E-44a)-1-C(O)OMe H 203-206
1-053 C(O)(G-22a) (E-44a)-1-C(O)OMe H 217-220
1-054 C(O)(G-3a) (E-44a)-1-C(O)OMe 2-OMe-5-F 168-170
1-055 CH2CH=CHCl E-38a 2-OMe-5-F 93-95
1-056 CH2C(=NOMe)Me E-38a 3-Cl 75-77
1-057 CH2C(=NOMe)Me (E-44a)-1-C(O)OMe 3-Cl 86-88
1-058 C(O)(G-3a) E-38a 3-Cl 219-220
1-059 C(O)(G-22a) E-38a 3-Cl *
1-060 H E-38a 3-Cl 254-256
1-061 H (E-44a)-1-C(O)OMe 3-Cl 178-180
1-062 CH2(Ph-2-F) (E-44a)-1-C(O)OMe 2-OMe-5-F 110-112
1-063 C(O)OnPr E-38a 2-OMe-5-F *
1-064 CH2(G-3a) E-38a 3-Cl *
1-065 CH2CH=CHCl E-38a 3-Cl *
1-066 CH2(Ph-2-F) E-38a 3-Cl *
1-067 C(O)OtBu E-41a 2-OMe-5-F *
1-068 C(O)OtBu CH(Me)C(O)N(OMe)Me 2-OMe-5-F *
1-069 C(O)OtBu L-6a 2-OMe-5-F *
1-070 C(O)OtBu cHex 2-OMe-5-F *
1-071 C(O)OtBu (L-7a)-4-OMe 2-OMe-5-F *
1-072 C(O)OtBu (E-44a)-1-C(O)Me 2-OMe-5-F *
1-073 C(O)OtBu (E-44a)-1-C(O)Et 2-OMe-5-F *
1-074 C(O)OtBu E-38a 3-Me 207-209
1-075 C(O)OtBu L-5a 3-Me 187-189
1-076 C(O)OtBu (E-44a)-1-C(O)OMe 3-Me 182-184
1-077 C(O)OtBu E-38a 2-OMe-5-Cl 116-119
1-078 C(O)OtBu L-5a 2-OMe-5-Cl *
1-079 C(O)OtBu (E-44a)-1-C(O)OMe 2-OMe-5-Cl *
1-080 C(O)OtBu E-38a 2-OEt 182-184
1-081 C(O)OtBu L-5a 2-OEt 187-189
1-082 C(O)OtBu (E-44a)-1-C(O)OMe 2-OEt 169-171
1-083 Ph E-38a 2-OMe-5-F 114-116
1-084 Ph L-5a 2-OMe-5-F 159-161
1-085 Ph (E-44a)-1-C(O)OMe 2-OMe-5-F 156-158
1-086 C(O)CH(Et)2 L-5a 2-OMe-5-F *
1-087 C(O)(G-4a) L-5a 2-OMe-5-F 209-211
1-088 C(O)(G-3a) L-5a 2-OMe-5-F 212-214
1-089 C(O)OtBu L-5b 2-OMe-5-F *
1-090 C(O)OtBu L-5c 2-OMe-5-F *
1-091 C(O)OtBu (L-7a)-4-C(O)OMe 2-OMe-5-F *
1-092 CH2C(=NOCH2C(O)Me)Me L-5a 2-OMe-5-F *
1-093 CH2C(=NOH)Me L-5a 2-OMe-5-F *
1-094 C(O)OtBu (E-44a)-1-C(O)OEt 2-OMe-5-F *
1-095 C(O)OtBu (E-44a)-1-C(O)C(O)OMe 2-OMe-5-F 132-133
1-096 C(O)OtBu (E-44a)-1-S(O)2Me 2-OMe-5-F *
1-097 C(O)OtBu (E-44a)-1-C(O)N(Me)2 2-OMe-5-F 81-83
1-098 C(O)Ph L-5a 2-OMe-5-F 219-221
1-099 C(O)(G-22a) L-5a 2-OMe-5-F 122-124
1-100 C(O)OiBu L-5a 2-OMe-5-F *
1-101 CH2(Ph-3-F) L-5a 2-OMe-5-F 182-184
1-102 CH2Ph L-5a 2-OMe-5-F *
1-103 CH2(G-3a) L-5a 2-OMe-5-F 127-129
1-104 CH2(G-4a) L-5a 2-OMe-5-F 132-134
1-105 CH2C(=NOMe)Me L-5a 2-OMe-5-F *
1-106 CH2CH=CHCl L-5a 2-OMe-5-F *
1-107 CH2(Ph-2-F) L-5a 2-OMe-5-F *
1-108 C(O)C(=NOMe)Me L-5a 2-OMe-5-F *
1-109 C(O)OtBu (E-44a)-1-S(O)2N(Me)2 2-OMe-5-F *
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[第4表]
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No. R 2 R 6 (Z) m1 mp (°C)
――――――――――――――――――――――――――――――――――
1-001 C(O)OtBu E-38a 2-OMe-5-F *
1-002 C(O)OtBu iPr 2-OMe-5-F 219-221
1-003 CH2 (Ph-2-F) E-38a 2-OMe-5-F 169-171
1-004H E-38a 2-OMe-5-F 186-188
1-005 C(O)(G-3a) E-38a 2-OMe-5-F 206-209
1-006 C(O)OiBu E-38a 2-OMe-5-F 153-156
1-007 CH2CH=C(Me)2E-38a 2 -OMe-5-F 173-175
1-008 C(O)(G-22a) E-38a 2-OMe-5-F 156-163
1-009 C(O)Ph E-38a 2-OMe-5-F 179-182
1-010 CH2 (Ph-2-F) E-38a 3-F 169-171
1-011 CH2 (Ph-2-F) E-38a 2-OMe 173-175
1-012 CH2 (G-3a) E-38a 2-OMe-5-F 184-186
1-013 CH2 (G-3a) E-38a 3-F*
1-014 CH2 (G-3a) E-38a 2-OMe*
1-015 CH2C(=NOMe)Me E-38a 2-OMe 187-189
1-016 CH2C(=NOMe)Me E-38a 3-F*
1-017 CH2 (Ph-2-F-6-Cl) E-38a 2-OMe*
1-018 CH2 (Ph-2-F-6-Cl) E-38a 3-F*
1-019 C(O)Ph E-38a 2-OMe 215-217
1-020 C(O)(G-3a) E-38a 2-OMe 210-212
1-021 C(O)(G-4a) E-38a 2-OMe 204-205
1-022 C(O)Ph E-38a 3-F 112-114
1-023 C(O)(G-3a) E-38a 3-F 197-199
1-024 C(O)(G-4a) E-38a 3-F 211-213
1-025 C(O)(G-22a) E-38a 2-OMe *
1-026 C(O)(G-22a) E-38a 3-F *
1-027 C(O)OiBu E-38a 2-OMe*
1-028 C(O)OiBu E-38a 3-F*
1-029 CH2C(=NOMe)MeCH(Me)C(O)N(H)Me2-OMe-5-F 203-205
1-030 C(O)OiBu CH(Me)C(O)N(H)Me 2-OMe-5-F 154-156
1-031 CH2C(=NOMe)Me(E-44a)-1-C(O)OMe2-OMe-5-F*
1-032 CH2 (G-3a)CH(Me)C(O)N(H)Me2-OMe-5-F 153-155
1-033 CH2CH=CHClCH(Me)C(O)N(H)Me2-OMe-5-F 117-119
1-034 C(O)(G-3a)CH(Me)C(O)N(H)Me 2-OMe-5-F 194-196
1-035 CH2C(=NOMe)Me E-38a 2-OMe-5-F 71-73
1-036 CH2 (G-3a)(E-44a)-1-C(O)OMe2-OMe-5-F 100-102
1-037 CH2CH=CHCl (E-44a)-1-C(O)OMe 2-OMe-5-F 94-96
1-038 C(O)OiBu (E-44a)-1-C(O)OMe 2-OMe-5-F *
1-039 C(O)(G-22a) (E-44a)-1-C(O)OMe 2-OMe-5-F 140-142
1-040 CH2PhE - 38aH168-170
1-041 CH2 (G-3a) E-38a H86-88
1-042 CH2C(=NOMe)Me E-38aH*
1-043 CH2CH=CHCl E-38a H114-116
1-044 CH2Ph(E-44a)-1-C(O)OMeH 177-179
1-045 CH2 (G-3a)(E-44a)-1-C(O)OMe H 156-158
1-046 CH2C(=NOMe)Me(E-44a)-1-C(O)OMeH*
1-047 CH2CH=CHCl(E-44a)-1-C(O)OMeH*
1-048 C(O)Ph E-38a H 198-200
1-049 C(O)(G-3a) E-38a H 210-213
1-050 C(O)(G-22a) E-38a H 189-192
1-051 C(O)Ph (E-44a)-1-C(O)OMe H 206-208
1-052 C(O)(G-3a) (E-44a)-1-C(O)OMe H 203-206
1-053 C(O)(G-22a) (E-44a)-1-C(O)OMe H 217-220
1-054 C(O)(G-3a) (E-44a)-1-C(O)OMe 2-OMe-5-F 168-170
1-055 CH2CH=CHCl E-38a 2 -OMe-5-F 93-95
1-056 CH2C(=NOMe)Me E-38a 3-Cl 75-77
1-057 CH2C(=NOMe)Me(E-44a)-1-C(O)OMe3-Cl 86-88
1-058 C(O)(G-3a) E-38a 3-Cl 219-220
1-059 C(O)(G-22a) E-38a 3-Cl*
1-060 H E-38a 3-Cl 254-256
1-061 H (E-44a)-1-C(O)OMe 3-Cl 178-180
1-062 CH2 (Ph-2-F)(E-44a)-1-C(O)OMe2-OMe-5-F 110-112
1-063 C(O)OnPr E-38a 2-OMe-5-F*
1-064 CH2 (G-3a) E-38a 3-Cl*
1-065 CH2CH=CHCl E-38a 3-Cl*
1-066 CH2 (Ph-2-F) E-38a 3-Cl*
1-067 C(O)OtBu E-41a 2-OMe-5-F*
1-068 C(O)OtBu CH(Me)C(O)N(OMe)Me 2-OMe-5-F *
1-069 C(O)OtBu L-6a 2-OMe-5-F *
1-070 C(O)OtBu cHex 2-OMe-5-F *
1-071 C(O)OtBu(L-7a)-4-OMe 2-OMe-5-F*
1-072 C(O)OtBu(E-44a)-1-C(O)Me2-OMe-5-F*
1-073 C(O)OtBu (E-44a)-1-C(O)Et 2-OMe-5-F *
1-074 C(O)OtBu E-38a 3-Me 207-209
1-075 C(O)OtBu L-5a 3-Me 187-189
1-076 C(O)OtBu(E-44a)-1-C(O)OMe3-Me 182-184
1-077 C(O)OtBu E-38a 2-OMe-5-Cl 116-119
1-078 C(O)OtBu L-5a 2-OMe-5-Cl*
1-079 C(O)OtBu (E-44a)-1-C(O)OMe 2-OMe-5-Cl *
1-080 C(O)OtBu E-38a 2-OEt 182-184
1-081 C(O)OtBu L-5a 2-OEt 187-189
1-082 C(O)OtBu (E-44a)-1-C(O)OMe2-OEt 169-171
1-083 Ph E-38a 2-OMe-5-F 114-116
1-084 Ph L-5a 2-OMe-5-F 159-161
1-085 Ph(E-44a)-1-C(O)OMe 2-OMe-5-F 156-158
1-086 C(O)CH(Et)2L-5a2-OMe-5-F*
1-087 C(O)(G-4a) L-5a 2-OMe-5-F 209-211
1-088 C(O)(G-3a) L-5a 2-OMe-5-F 212-214
1-089 C(O)OtBu L-5b 2-OMe-5-F *
1-090 C(O)OtBu L-5c 2-OMe-5-F *
1-091 C(O)OtBu(L-7a)-4-C(O)OMe 2-OMe-5-F*
1-092 CH2C(= NOCH2C (O)Me)MeL-5a2-OMe-5-F*
1-093 CH2C(=NOH)MeL-5a2-OMe-5-F*
1-094 C(O)OtBu (E-44a)-1-C(O)OEt 2-OMe-5-F *
1-095 C(O)OtBu (E-44a)-1-C(O)C(O)OMe 2-OMe-5-F 132-133
1-096 C(O)OtBu(E-44a)-1-S(O) 2Me2 -OMe-5-F*
1-097 C(O)OtBu(E-44a)-1-C(O)N(Me)22 - OMe-5-F 81-83
1-098 C(O)Ph L-5a 2-OMe-5-F 219-221
1-099 C(O)(G-22a) L-5a 2-OMe-5-F 122-124
1-100 C(O)OiBu L-5a 2-OMe-5-F *
1-101 CH2 (Ph-3-F) L-5a 2-OMe-5-F 182-184
1-102CH2PhL - 5a2-OMe-5-F*
1-103 CH2 (G-3a) L-5a 2-OMe-5-F 127-129
1-104 CH2 (G-4a) L-5a 2-OMe-5-F 132-134
1-105 CH2C ( =NOMe)MeL-5a2-OMe-5-F*
1-106 CH2CH=CHClL-5a2-OMe-5-F*
1-107CH2(Ph- 2 -F)L-5a2-OMe-5-F*
1-108 C(O)C(=NOMe)MeL-5a 2-OMe-5-F *
1-109 C(O) OtBu (E-44a)-1-S(O)2N(Me)22 - OMe-5-F*
――――――――――――――――――――――――――――――――――
[Table 4]
No. R2 R6 (Z)m1 m.p.(℃)
――――――――――――――――――――――――――――――――――
1-001 C(O)OtBu E-38a 2-OMe-5-F *
1-002 C(O)OtBu iPr 2-OMe-5-F 219-221
1-003 CH2(Ph-2-F) E-38a 2-OMe-5-F 169-171
1-004 H E-38a 2-OMe-5-F 186-188
1-005 C(O)(G-3a) E-38a 2-OMe-5-F 206-209
1-006 C(O)OiBu E-38a 2-OMe-5-F 153-156
1-007 CH2CH=C(Me)2 E-38a 2-OMe-5-F 173-175
1-008 C(O)(G-22a) E-38a 2-OMe-5-F 156-163
1-009 C(O)Ph E-38a 2-OMe-5-F 179-182
1-010 CH2(Ph-2-F) E-38a 3-F 169-171
1-011 CH2(Ph-2-F) E-38a 2-OMe 173-175
1-012 CH2(G-3a) E-38a 2-OMe-5-F 184-186
1-013 CH2(G-3a) E-38a 3-F *
1-014 CH2(G-3a) E-38a 2-OMe *
1-015 CH2C(=NOMe)Me E-38a 2-OMe 187-189
1-016 CH2C(=NOMe)Me E-38a 3-F *
1-017 CH2(Ph-2-F-6-Cl) E-38a 2-OMe *
1-018 CH2(Ph-2-F-6-Cl) E-38a 3-F *
1-019 C(O)Ph E-38a 2-OMe 215-217
1-020 C(O)(G-3a) E-38a 2-OMe 210-212
1-021 C(O)(G-4a) E-38a 2-OMe 204-205
1-022 C(O)Ph E-38a 3-F 112-114
1-023 C(O)(G-3a) E-38a 3-F 197-199
1-024 C(O)(G-4a) E-38a 3-F 211-213
1-025 C(O)(G-22a) E-38a 2-OMe *
1-026 C(O)(G-22a) E-38a 3-F *
1-027 C(O)OiBu E-38a 2-OMe *
1-028 C(O)OiBu E-38a 3-F *
1-029 CH2C(=NOMe)Me CH(Me)C(O)N(H)Me 2-OMe-5-F 203-205
1-030 C(O)OiBu CH(Me)C(O)N(H)Me 2-OMe-5-F 154-156
1-031 CH2C(=NOMe)Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
1-032 CH2(G-3a) CH(Me)C(O)N(H)Me 2-OMe-5-F 153-155
1-033 CH2CH=CHCl CH(Me)C(O)N(H)Me 2-OMe-5-F 117-119
1-034 C(O)(G-3a) CH(Me)C(O)N(H)Me 2-OMe-5-F 194-196
1-035 CH2C(=NOMe)Me E-38a 2-OMe-5-F 71-73
1-036 CH2(G-3a) (E-44a)-1-C(O)OMe 2-OMe-5-F 100-102
1-037 CH2CH=CHCl (E-44a)-1-C(O)OMe 2-OMe-5-F 94-96
1-038 C(O)OiBu (E-44a)-1-C(O)OMe 2-OMe-5-F *
1-039 C(O)(G-22a) (E-44a)-1-C(O)OMe 2-OMe-5-F 140-142
1-040 CH2Ph E-38a H 168-170
1-041 CH2(G-3a) E-38a H 86-88
1-042 CH2C(=NOMe)Me E-38a H *
1-043 CH2CH=CHCl E-38a H 114-116
1-044 CH2Ph (E-44a)-1-C(O)OMe H 177-179
1-045 CH2(G-3a) (E-44a)-1-C(O)OMe H 156-158
1-046 CH2C(=NOMe)Me (E-44a)-1-C(O)OMe H *
1-047 CH2CH=CHCl (E-44a)-1-C(O)OMe H *
1-048 C(O)Ph E-38a H 198-200
1-049 C(O)(G-3a) E-38a H 210-213
1-050 C(O)(G-22a) E-38a H 189-192
1-051 C(O)Ph (E-44a)-1-C(O)OMe H 206-208
1-052 C(O)(G-3a) (E-44a)-1-C(O)OMe H 203-206
1-053 C(O)(G-22a) (E-44a)-1-C(O)OMe H 217-220
1-054 C(O)(G-3a) (E-44a)-1-C(O)OMe 2-OMe-5-F 168-170
1-055 CH2CH=CHCl E-38a 2-OMe-5-F 93-95
1-056 CH2C(=NOMe)Me E-38a 3-Cl 75-77
1-057 CH2C(=NOMe)Me (E-44a)-1-C(O)OMe 3-Cl 86-88
1-058 C(O)(G-3a) E-38a 3-Cl 219-220
1-059 C(O)(G-22a) E-38a 3-Cl *
1-060 H E-38a 3-Cl 254-256
1-061 H (E-44a)-1-C(O)OMe 3-Cl 178-180
1-062 CH2(Ph-2-F) (E-44a)-1-C(O)OMe 2-OMe-5-F 110-112
1-063 C(O)OnPr E-38a 2-OMe-5-F *
1-064 CH2(G-3a) E-38a 3-Cl *
1-065 CH2CH=CHCl E-38a 3-Cl *
1-066 CH2(Ph-2-F) E-38a 3-Cl *
1-067 C(O)OtBu E-41a 2-OMe-5-F *
1-068 C(O)OtBu CH(Me)C(O)N(OMe)Me 2-OMe-5-F *
1-069 C(O)OtBu L-6a 2-OMe-5-F *
1-070 C(O)OtBu cHex 2-OMe-5-F *
1-071 C(O)OtBu (L-7a)-4-OMe 2-OMe-5-F *
1-072 C(O)OtBu (E-44a)-1-C(O)Me 2-OMe-5-F *
1-073 C(O)OtBu (E-44a)-1-C(O)Et 2-OMe-5-F *
1-074 C(O)OtBu E-38a 3-Me 207-209
1-075 C(O)OtBu L-5a 3-Me 187-189
1-076 C(O)OtBu (E-44a)-1-C(O)OMe 3-Me 182-184
1-077 C(O)OtBu E-38a 2-OMe-5-Cl 116-119
1-078 C(O)OtBu L-5a 2-OMe-5-Cl *
1-079 C(O)OtBu (E-44a)-1-C(O)OMe 2-OMe-5-Cl *
1-080 C(O)OtBu E-38a 2-OEt 182-184
1-081 C(O)OtBu L-5a 2-OEt 187-189
1-082 C(O)OtBu (E-44a)-1-C(O)OMe 2-OEt 169-171
1-083 Ph E-38a 2-OMe-5-F 114-116
1-084 Ph L-5a 2-OMe-5-F 159-161
1-085 Ph (E-44a)-1-C(O)OMe 2-OMe-5-F 156-158
1-086 C(O)CH(Et)2 L-5a 2-OMe-5-F *
1-087 C(O)(G-4a) L-5a 2-OMe-5-F 209-211
1-088 C(O)(G-3a) L-5a 2-OMe-5-F 212-214
1-089 C(O)OtBu L-5b 2-OMe-5-F *
1-090 C(O)OtBu L-5c 2-OMe-5-F *
1-091 C(O)OtBu (L-7a)-4-C(O)OMe 2-OMe-5-F *
1-092 CH2C(=NOCH2C(O)Me)Me L-5a 2-OMe-5-F *
1-093 CH2C(=NOH)Me L-5a 2-OMe-5-F *
1-094 C(O)OtBu (E-44a)-1-C(O)OEt 2-OMe-5-F *
1-095 C(O)OtBu (E-44a)-1-C(O)C(O)OMe 2-OMe-5-F 132-133
1-096 C(O)OtBu (E-44a)-1-S(O)2Me 2-OMe-5-F *
1-097 C(O)OtBu (E-44a)-1-C(O)N(Me)2 2-OMe-5-F 81-83
1-098 C(O)Ph L-5a 2-OMe-5-F 219-221
1-099 C(O)(G-22a) L-5a 2-OMe-5-F 122-124
1-100 C(O)OiBu L-5a 2-OMe-5-F *
1-101 CH2(Ph-3-F) L-5a 2-OMe-5-F 182-184
1-102 CH2Ph L-5a 2-OMe-5-F *
1-103 CH2(G-3a) L-5a 2-OMe-5-F 127-129
1-104 CH2(G-4a) L-5a 2-OMe-5-F 132-134
1-105 CH2C(=NOMe)Me L-5a 2-OMe-5-F *
1-106 CH2CH=CHCl L-5a 2-OMe-5-F *
1-107 CH2(Ph-2-F) L-5a 2-OMe-5-F *
1-108 C(O)C(=NOMe)Me L-5a 2-OMe-5-F *
1-109 C(O)OtBu (E-44a)-1-S(O)2N(Me)2 2-OMe-5-F *
――――――――――――――――――――――――――――――――――
[第4表]
No. R 2 R 6 (Z) m1 mp (°C)
――――――――――――――――――――――――――――――――――
1-001 C(O)OtBu E-38a 2-OMe-5-F *
1-002 C(O)OtBu iPr 2-OMe-5-F 219-221
1-003 CH2 (Ph-2-F) E-38a 2-OMe-5-F 169-171
1-004H E-38a 2-OMe-5-F 186-188
1-005 C(O)(G-3a) E-38a 2-OMe-5-F 206-209
1-006 C(O)OiBu E-38a 2-OMe-5-F 153-156
1-007 CH2CH=C(Me)2E-38a 2 -OMe-5-F 173-175
1-008 C(O)(G-22a) E-38a 2-OMe-5-F 156-163
1-009 C(O)Ph E-38a 2-OMe-5-F 179-182
1-010 CH2 (Ph-2-F) E-38a 3-F 169-171
1-011 CH2 (Ph-2-F) E-38a 2-OMe 173-175
1-012 CH2 (G-3a) E-38a 2-OMe-5-F 184-186
1-013 CH2 (G-3a) E-38a 3-F*
1-014 CH2 (G-3a) E-38a 2-OMe*
1-015 CH2C(=NOMe)Me E-38a 2-OMe 187-189
1-016 CH2C(=NOMe)Me E-38a 3-F*
1-017 CH2 (Ph-2-F-6-Cl) E-38a 2-OMe*
1-018 CH2 (Ph-2-F-6-Cl) E-38a 3-F*
1-019 C(O)Ph E-38a 2-OMe 215-217
1-020 C(O)(G-3a) E-38a 2-OMe 210-212
1-021 C(O)(G-4a) E-38a 2-OMe 204-205
1-022 C(O)Ph E-38a 3-F 112-114
1-023 C(O)(G-3a) E-38a 3-F 197-199
1-024 C(O)(G-4a) E-38a 3-F 211-213
1-025 C(O)(G-22a) E-38a 2-OMe *
1-026 C(O)(G-22a) E-38a 3-F *
1-027 C(O)OiBu E-38a 2-OMe*
1-028 C(O)OiBu E-38a 3-F*
1-029 CH2C(=NOMe)MeCH(Me)C(O)N(H)Me2-OMe-5-F 203-205
1-030 C(O)OiBu CH(Me)C(O)N(H)Me 2-OMe-5-F 154-156
1-031 CH2C(=NOMe)Me(E-44a)-1-C(O)OMe2-OMe-5-F*
1-032 CH2 (G-3a)CH(Me)C(O)N(H)Me2-OMe-5-F 153-155
1-033 CH2CH=CHClCH(Me)C(O)N(H)Me2-OMe-5-F 117-119
1-034 C(O)(G-3a)CH(Me)C(O)N(H)Me 2-OMe-5-F 194-196
1-035 CH2C(=NOMe)Me E-38a 2-OMe-5-F 71-73
1-036 CH2 (G-3a)(E-44a)-1-C(O)OMe2-OMe-5-F 100-102
1-037 CH2CH=CHCl (E-44a)-1-C(O)OMe 2-OMe-5-F 94-96
1-038 C(O)OiBu (E-44a)-1-C(O)OMe 2-OMe-5-F *
1-039 C(O)(G-22a) (E-44a)-1-C(O)OMe 2-OMe-5-F 140-142
1-040 CH2PhE - 38aH168-170
1-041 CH2 (G-3a) E-38a H86-88
1-042 CH2C(=NOMe)Me E-38aH*
1-043 CH2CH=CHCl E-38a H114-116
1-044 CH2Ph(E-44a)-1-C(O)OMeH 177-179
1-045 CH2 (G-3a)(E-44a)-1-C(O)OMe H 156-158
1-046 CH2C(=NOMe)Me(E-44a)-1-C(O)OMeH*
1-047 CH2CH=CHCl(E-44a)-1-C(O)OMeH*
1-048 C(O)Ph E-38a H 198-200
1-049 C(O)(G-3a) E-38a H 210-213
1-050 C(O)(G-22a) E-38a H 189-192
1-051 C(O)Ph (E-44a)-1-C(O)OMe H 206-208
1-052 C(O)(G-3a) (E-44a)-1-C(O)OMe H 203-206
1-053 C(O)(G-22a) (E-44a)-1-C(O)OMe H 217-220
1-054 C(O)(G-3a) (E-44a)-1-C(O)OMe 2-OMe-5-F 168-170
1-055 CH2CH=CHCl E-38a 2 -OMe-5-F 93-95
1-056 CH2C(=NOMe)Me E-38a 3-Cl 75-77
1-057 CH2C(=NOMe)Me(E-44a)-1-C(O)OMe3-Cl 86-88
1-058 C(O)(G-3a) E-38a 3-Cl 219-220
1-059 C(O)(G-22a) E-38a 3-Cl*
1-060 H E-38a 3-Cl 254-256
1-061 H (E-44a)-1-C(O)OMe 3-Cl 178-180
1-062 CH2 (Ph-2-F)(E-44a)-1-C(O)OMe2-OMe-5-F 110-112
1-063 C(O)OnPr E-38a 2-OMe-5-F*
1-064 CH2 (G-3a) E-38a 3-Cl*
1-065 CH2CH=CHCl E-38a 3-Cl*
1-066 CH2 (Ph-2-F) E-38a 3-Cl*
1-067 C(O)OtBu E-41a 2-OMe-5-F*
1-068 C(O)OtBu CH(Me)C(O)N(OMe)Me 2-OMe-5-F *
1-069 C(O)OtBu L-6a 2-OMe-5-F *
1-070 C(O)OtBu cHex 2-OMe-5-F *
1-071 C(O)OtBu(L-7a)-4-OMe 2-OMe-5-F*
1-072 C(O)OtBu(E-44a)-1-C(O)Me2-OMe-5-F*
1-073 C(O)OtBu (E-44a)-1-C(O)Et 2-OMe-5-F *
1-074 C(O)OtBu E-38a 3-Me 207-209
1-075 C(O)OtBu L-5a 3-Me 187-189
1-076 C(O)OtBu(E-44a)-1-C(O)OMe3-Me 182-184
1-077 C(O)OtBu E-38a 2-OMe-5-Cl 116-119
1-078 C(O)OtBu L-5a 2-OMe-5-Cl*
1-079 C(O)OtBu (E-44a)-1-C(O)OMe 2-OMe-5-Cl *
1-080 C(O)OtBu E-38a 2-OEt 182-184
1-081 C(O)OtBu L-5a 2-OEt 187-189
1-082 C(O)OtBu (E-44a)-1-C(O)OMe2-OEt 169-171
1-083 Ph E-38a 2-OMe-5-F 114-116
1-084 Ph L-5a 2-OMe-5-F 159-161
1-085 Ph(E-44a)-1-C(O)OMe 2-OMe-5-F 156-158
1-086 C(O)CH(Et)2L-5a2-OMe-5-F*
1-087 C(O)(G-4a) L-5a 2-OMe-5-F 209-211
1-088 C(O)(G-3a) L-5a 2-OMe-5-F 212-214
1-089 C(O)OtBu L-5b 2-OMe-5-F *
1-090 C(O)OtBu L-5c 2-OMe-5-F *
1-091 C(O)OtBu(L-7a)-4-C(O)OMe 2-OMe-5-F*
1-092 CH2C(= NOCH2C (O)Me)MeL-5a2-OMe-5-F*
1-093 CH2C(=NOH)MeL-5a2-OMe-5-F*
1-094 C(O)OtBu (E-44a)-1-C(O)OEt 2-OMe-5-F *
1-095 C(O)OtBu (E-44a)-1-C(O)C(O)OMe 2-OMe-5-F 132-133
1-096 C(O)OtBu(E-44a)-1-S(O) 2Me2 -OMe-5-F*
1-097 C(O)OtBu(E-44a)-1-C(O)N(Me)22 - OMe-5-F 81-83
1-098 C(O)Ph L-5a 2-OMe-5-F 219-221
1-099 C(O)(G-22a) L-5a 2-OMe-5-F 122-124
1-100 C(O)OiBu L-5a 2-OMe-5-F *
1-101 CH2 (Ph-3-F) L-5a 2-OMe-5-F 182-184
1-102CH2PhL - 5a2-OMe-5-F*
1-103 CH2 (G-3a) L-5a 2-OMe-5-F 127-129
1-104 CH2 (G-4a) L-5a 2-OMe-5-F 132-134
1-105 CH2C ( =NOMe)MeL-5a2-OMe-5-F*
1-106 CH2CH=CHClL-5a2-OMe-5-F*
1-107CH2(Ph- 2 -F)L-5a2-OMe-5-F*
1-108 C(O)C(=NOMe)MeL-5a 2-OMe-5-F *
1-109 C(O) OtBu (E-44a)-1-S(O)2N(Me)22 - OMe-5-F*
――――――――――――――――――――――――――――――――――
[Table 4]
―――――――――――――――――――――――――――――――――
No. R2 R7 R6 (Z)m1 m.p.(℃)
―――――――――――――――――――――――――――――――――
2-001 C(O)OtBu SiMe3 E-38a 2-OMe-5-F 108-110
2-002 C(O)OtBu H E-38a 2-OMe-5-F 176-178
2-003 C(O)OtBu Me E-38a 2-OMe-5-F *
2-004 C(O)OtBu cPr E-38a 2-OMe-5-F *
2-005 CH2Ph Me E-38a 2-OMe-5-F *
2-006 CH2(Ph-2-F) Me E-38a 2-OMe-5-F *
2-007 CH2Ph H E-38a 2-OMe-5-F *
2-008 C(O)Ph H E-38a 2-OMe-5-F *
2-009 C(O)Ph C(O)Ph E-38a 2-OMe-5-F 107-109
2-010 C(O)Ph SiMe3 E-38a 2-OMe-5-F 192-196
2-011 C(O)(G-21a) Me E-38a 2-OMe-5-F *
2-012 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F *
2-013 C(O)OiBu Me E-38a 2-OMe-5-F *
2-014 C(O)Ph Me E-38a 2-OMe-5-F *
2-015 C(O)(G-3a) Me E-38a 2-OMe-5-F *
2-016 H H E-38a 2-OMe-5-F *
2-017 H Me E-38a 2-OMe-5-F 54-56
2-018 C(O)C(O)Me Me E-38a 2-OMe-5-F *
2-019 CH2(G-3a) Me E-38a 2-OMe-5-F *
2-020 CH2CH=CHCl (E) Me E-38a 2-OMe-5-F *
2-021 CH2CH=CHCl (Z) Me E-38a 2-OMe-5-F 164-166
2-022 C(O)(G-22a) Me E-38a 2-OMe-5-F *
―――――――――――――――――――――――――――――――――
[第5表]
―――――――――――――――――――――――――――――――――
No. R2 R7 R6 (Z) m1 mp (°C)
―――――――――――――――――――――――――――――――――
2-001 C(O)OtBu SiMe3 E-38a 2-OMe-5-F 108-110
2-002 C(O)OtBuH E-38a 2-OMe-5-F 176-178
2-003 C(O)OtBu Me E-38a 2-OMe-5-F *
2-004 C(O)OtBu cPr E-38a 2-OMe-5-F *
2-005 CH2PhMe E-38a 2 -OMe-5-F*
2-006 CH2 (Ph-2-F)Me E-38a 2-OMe-5-F*
2-007 CH2PhH E-38a 2 -OMe-5-F*
2-008 C(O)Ph H E-38a 2-OMe-5-F *
2-009 C(O)Ph C(O)Ph E-38a 2-OMe-5-F 107-109
2-010 C(O)Ph SiMe3 E-38a 2-OMe-5-F 192-196
2-011 C(O)(G-21a) Me E-38a 2-OMe-5-F *
2-012 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F*
2-013 C(O)OiBu Me E-38a 2-OMe-5-F *
2-014 C(O)Ph Me E-38a 2-OMe-5-F *
2-015 C(O)(G-3a) Me E-38a 2-OMe-5-F *
2-016HH E-38a 2-OMe-5-F*
2-017 H Me E-38a 2-OMe-5-F 54-56
2-018 C(O)C(O)Me Me E-38a 2-OMe-5-F *
2-019 CH2 (G-3a) Me E-38a 2-OMe-5-F*
2-020 CH2CH=CHCl(E)Me E-38a 2-OMe-5-F *
2-021 CH2CH=CHCl(Z)Me E-38a 2-OMe-5-F 164-166
2-022 C(O)(G-22a) Me E-38a 2-OMe-5-F *
―――――――――――――――――――――――――――――――――
[Table 5]
No. R2 R7 R6 (Z)m1 m.p.(℃)
―――――――――――――――――――――――――――――――――
2-001 C(O)OtBu SiMe3 E-38a 2-OMe-5-F 108-110
2-002 C(O)OtBu H E-38a 2-OMe-5-F 176-178
2-003 C(O)OtBu Me E-38a 2-OMe-5-F *
2-004 C(O)OtBu cPr E-38a 2-OMe-5-F *
2-005 CH2Ph Me E-38a 2-OMe-5-F *
2-006 CH2(Ph-2-F) Me E-38a 2-OMe-5-F *
2-007 CH2Ph H E-38a 2-OMe-5-F *
2-008 C(O)Ph H E-38a 2-OMe-5-F *
2-009 C(O)Ph C(O)Ph E-38a 2-OMe-5-F 107-109
2-010 C(O)Ph SiMe3 E-38a 2-OMe-5-F 192-196
2-011 C(O)(G-21a) Me E-38a 2-OMe-5-F *
2-012 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F *
2-013 C(O)OiBu Me E-38a 2-OMe-5-F *
2-014 C(O)Ph Me E-38a 2-OMe-5-F *
2-015 C(O)(G-3a) Me E-38a 2-OMe-5-F *
2-016 H H E-38a 2-OMe-5-F *
2-017 H Me E-38a 2-OMe-5-F 54-56
2-018 C(O)C(O)Me Me E-38a 2-OMe-5-F *
2-019 CH2(G-3a) Me E-38a 2-OMe-5-F *
2-020 CH2CH=CHCl (E) Me E-38a 2-OMe-5-F *
2-021 CH2CH=CHCl (Z) Me E-38a 2-OMe-5-F 164-166
2-022 C(O)(G-22a) Me E-38a 2-OMe-5-F *
―――――――――――――――――――――――――――――――――
[第5表]
No. R2 R7 R6 (Z) m1 mp (°C)
―――――――――――――――――――――――――――――――――
2-001 C(O)OtBu SiMe3 E-38a 2-OMe-5-F 108-110
2-002 C(O)OtBuH E-38a 2-OMe-5-F 176-178
2-003 C(O)OtBu Me E-38a 2-OMe-5-F *
2-004 C(O)OtBu cPr E-38a 2-OMe-5-F *
2-005 CH2PhMe E-38a 2 -OMe-5-F*
2-006 CH2 (Ph-2-F)Me E-38a 2-OMe-5-F*
2-007 CH2PhH E-38a 2 -OMe-5-F*
2-008 C(O)Ph H E-38a 2-OMe-5-F *
2-009 C(O)Ph C(O)Ph E-38a 2-OMe-5-F 107-109
2-010 C(O)Ph SiMe3 E-38a 2-OMe-5-F 192-196
2-011 C(O)(G-21a) Me E-38a 2-OMe-5-F *
2-012 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F*
2-013 C(O)OiBu Me E-38a 2-OMe-5-F *
2-014 C(O)Ph Me E-38a 2-OMe-5-F *
2-015 C(O)(G-3a) Me E-38a 2-OMe-5-F *
2-016HH E-38a 2-OMe-5-F*
2-017 H Me E-38a 2-OMe-5-F 54-56
2-018 C(O)C(O)Me Me E-38a 2-OMe-5-F *
2-019 CH2 (G-3a) Me E-38a 2-OMe-5-F*
2-020 CH2CH=CHCl(E)Me E-38a 2-OMe-5-F *
2-021 CH2CH=CHCl(Z)Me E-38a 2-OMe-5-F 164-166
2-022 C(O)(G-22a) Me E-38a 2-OMe-5-F *
―――――――――――――――――――――――――――――――――
[Table 5]
――――――――――――――――――――――――――――――――――
No. R2 Ra R6 (Z)m1 m.p.(℃)
――――――――――――――――――――――――――――――――――
3-001 CH2(G-3a) Me E-38a 2-OMe-5-F *
3-002 C(O)(G-3a) Me E-38a 2-OMe-5-F *
3-003 C(O)(G-22a) Me E-38a 2-OMe-5-F *
3-004 C(O)C(O)N(H)tBu Me E-38a 2-OMe-5-F *
3-005 C(O)OiBu Me E-38a 2-OMe-5-F *
3-006 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F *
3-007 CH2CH=CHCl Me E-38a 2-OMe-5-F *
3-008 C(O)C(=NOMe)Me Me E-38a 2-OMe-5-F *
3-009 CH2(Ph-2-F) Me E-38a 2-OMe-5-F *
3-010 C(O)OCH2tBu Me E-38a 2-OMe-5-F *
3-011 C(O)((G-22a)-2-Me) Me E-38a 2-OMe-5-F 149-151
3-012 C(O)(G-4a) Me E-38a 2-OMe-5-F 164-166
3-013 C(O)((G-3a)-3-Me) Me E-38a 2-OMe-5-F 141-144
3-014 C(O)Ph Me E-38a 2-OMe-5-F *
3-015 C(O)((G-22a)-2-Cl) Me E-38a 2-OMe-5-F *
3-016 C(O)((G-22a)-2-tBu) Me E-38a 2-OMe-5-F *
3-017 C(O)((G-3a)-5-Me) Me E-38a 2-OMe-5-F *
3-018 C(O)((G-3a)-5-Cl) Me E-38a 2-OMe-5-F *
3-019 C(O)cHex Me E-38a 2-OMe-5-F *
3-020 C(O)cPen Me E-38a 2-OMe-5-F *
3-021 C(O)CH(Et)2 Me E-38a 2-OMe-5-F *
3-022 CH2CH=CCl2 Me E-38a 2-OMe-5-F *
3-023 C(O)OcHex Me E-38a 2-OMe-5-F *
3-024 CH2(G-3a) Et E-38a 2-OMe-5-F *
3-025 C(O)OiBu Et E-38a 2-OMe-5-F *
3-026 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-027 C(O)(G-3a) Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-028 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-029 C(O)(G-22a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-030 C(O)(G-22a) Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-031 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-032 CH2(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-033 CH2(G-3a) Me CH(Me)C(O)N(H)Me 2-OMe-5-F 167-169
3-034 CH2CH=CHCl Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-035 CH2CH=CHCl Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-036 CH2(Ph-2-F) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-037 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-038 C(O)OiBu Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-039 CH2C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-040 CH2C(=NOMe)Me Me CH(Me)C(O)N(H)Me 2-OMe-5-F 121-123
3-041 C(O)C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-042 C(O)C(=NOMe)Me Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-043 C(O)C(O)N(H)tBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-044 C(O)OiBu Me (E-44a)-1-C(O)OMe H *
3-045 C(O)OiBu Me CH(Me)C(O)N(H)Me H *
3-046 C(O)OiBu Me E-38a H *
3-047 CH2C(=NOMe)Me Me (E-44a)-1-C(O)OMe H *
3-048 CH2C(=NOMe)Me Me CH(Me)C(O)N(H)Me H 145-149
3-049 CH2C(=NOMe)Me Me E-38a H *
3-050 CH2(G-3a) Me (E-44a)-1-C(O)OMe H *
3-051 CH2(G-3a) Me CH(Me)C(O)N(H)Me H *
3-052 CH2(G-3a) Me E-38a H *
3-053 CH2CH=CHCl Me (E-44a)-1-C(O)OMe H 127-129
3-054 CH2CH=CHCl Me CH(Me)C(O)N(H)Me H *
3-055 CH2CH=CHCl Me E-38a H *
3-056 CH2(Ph-2-F) Me (E-44a)-1-C(O)OMe H *
3-057 CH2(Ph-2-F) Me CH(Me)C(O)N(H)Me H *
3-058 CH2(Ph-2-F) Me E-38a H *
3-059 C(O)(G-3a) Me (E-44a)-1-C(O)OMe H *
3-060 C(O)(G-3a) Me CH(Me)C(O)N(H)Me H 243-245
3-061 C(O)(G-3a) Me E-38a H *
3-062 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe H *
3-063 C(O)((G-3a)-3-Me) Me CH(Me)C(O)N(H)Me H 219-221
3-064 C(O)((G-3a)-3-Me) Me E-38a H *
3-065 C(O)Ph Me (E-44a)-1-C(O)OMe H *
3-066 C(O)Ph Me CH(Me)C(O)N(H)Me H 227-229
3-067 C(O)Ph Me E-38a H *
3-068 C(O)C(O)N(H)tBu Me (E-44a)-1-C(O)OMe H *
3-069 C(O)C(O)N(H)tBu Me CH(Me)C(O)N(H)Me H *
3-070 C(O)C(=NOMe)Me Me (E-44a)-1-C(O)OMe H *
3-071 C(O)(G-4a) Me CH(Me)C(O)N(H)Me H 207-209
3-072 C(O)C(=NOMe)Me Me E-38a H *
3-073 C(O)(G-22a) Me (E-44a)-1-C(O)OMe H *
3-074 C(O)(G-22a) Me CH(Me)C(O)N(H)Me H 229-231
3-075 C(O)(G-22a) Me E-38a H *
3-076 CH2(G-3a) Me E-38a 2-OMe *
3-077 CH2(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-078 CH2CH=CHCl Me E-38a 2-OMe *
3-079 CH2CH=CHCl Me (E-44a)-1-C(O)OMe 2-OMe *
3-080 CH2(Ph-2-F) Me E-38a 2-OMe *
3-081 CH2(Ph-2-F) Me (E-44a)-1-C(O)OMe 2-OMe *
3-082 CH2(G-4a) Me E-38a 2-OMe *
3-083 CH2(G-4a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-084 C(O)(G-22a) Me E-38a 2-OMe *
3-085 CH2C(=NOMe)Me Me E-38a 2-OMe *
3-086 CH2C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe *
3-087 C(O)OiBu Me E-38a 2-OMe *
3-088 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe *
3-089 C(O)(G-3a) Me E-38a 2-OMe *
3-090 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-091 C(O)((G-3a)-3-Me) Me E-38a 2-OMe *
3-092 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe *
3-093 C(O)(G-1a) Me E-38a 3-Cl *
3-094 C(O)(G-52a) Me E-38a 3-Cl *
3-095 C(O)iBu Me E-38a 3-Cl *
3-096 C(O)((G-53a)-6-Cl) Me E-38a 3-Cl *
3-097 C(O)(G-21a) Me E-38a 3-Cl *
3-098 C(O)((G-21a)-4-Me) Me E-38a 3-Cl 181-182
3-099 C(O)((G-17a)-1-Me) Me E-38a 3-Cl *
3-100 C(O)((G-16a)-1-Me) Me E-38a 3-Cl *
3-101 C(O)((G-15a)-1-Me) Me E-38a 3-Cl 184-186
3-102 C(O)((G-3a)-3-Cl) Me E-38a 3-Cl *
3-103 C(O)((G-52a)-5-Cl) Me E-38a 3-Cl *
3-104 C(O)((G-52a)-6-Cl) Me E-38a 3-Cl *
3-105 CH2(G-3a) Me L-5a 2-OMe-5-F *
3-106 CH2(G-4a) Me L-5a 2-OMe-5-F *
3-107 CH2Ph Me L-5a 2-OMe-5-F *
3-108 CH2(Ph-2-F) Me L-5a 2-OMe-5-F *
3-109 CH2CH=CHCl Me L-5a 2-OMe-5-F *
3-110 C(O)C(O)OtBu Me L-5a 2-OMe-5-F *
3-111 CH2(Ph-3-F) Me (E-44a)-1-C(O)OMe 3-Cl *
3-112 CH2(Ph-4-F) Me (E-44a)-1-C(O)OMe 3-Cl *
3-113 CH2(Ph-2-Me) Me (E-44a)-1-C(O)OMe 3-Cl *
3-114 CH2(Ph-2-OMe) Me (E-44a)-1-C(O)OMe 3-Cl *
3-115 CH2(Ph-2,6-F2) Me (E-44a)-1-C(O)OMe 3-Cl *
3-116 CH2((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 3-Cl *
3-117 CH2(G-22a) Me (E-44a)-1-C(O)OMe 3-Cl *
3-118 CH2((G-23a)-2-Cl) Me (E-44a)-1-C(O)OMe 3-Cl *
3-119 CH2((G-53a)-6-Cl) Me (E-44a)-1-C(O)OMe 3-Cl *
3-120 CH2cPr Me (E-44a)-1-C(O)OMe 3-Cl *
3-121 CH2CH=CHCl Me (E-44a)-1-C(O)OMe 3-Cl *
3-122 C(O)(G-53a) Me E-38a 3-Cl *
3-123 CH2CH=CH2 Me L-5a 2-OMe-5-F 124-126
3-124 CH2(Ph-2,4-F2) Me L-5a 2-OMe-5-F 87-89
3-125 CH2C(=NOMe)Ph Me L-5a 2-OMe-5-F *
3-126 CH2C(=NOMe)Me Me L-5a 2-OMe-5-F *
3-127 C(O)(G-3a) Me L-5a 2-OMe-5-F 176-177
3-128 C(O)(G-4a) Me L-5a 2-OMe-5-F *
3-129 C(O)(G-22a) Me L-5a 2-OMe-5-F *
3-130 C(O)CH(Et)2 Me L-5a 2-OMe-5-F *
3-131 C(O)Ph Me L-5a 2-OMe-5-F *
3-132 C(O)OiBu Me L-5a 2-OMe-5-F *
3-133 nPen Me L-5a 2-OMe-5-F *
3-134 CH2C(=NOMe)tBu Me L-5a 2-OMe-5-F *
3-135 C(O)C(=NOMe)Me Me L-5a 2-OMe-5-F *
3-136 C(O)Ph Me E-38a 2-OMe *
3-137 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe *
3-138 C(O)(E-76a) Me L-5a 2-OMe-5-F *
3-139 C(O)(E-45a) Me L-5a 2-OMe-5-F *
3-140 C(O)N(Me)iPr Me L-5a 2-OMe-5-F *
3-141 C(O)N(Et)2 Me L-5a 2-OMe-5-F 65-67
――――――――――――――――――――――――――――――――――
[第6表]
――――――――――――――――――――――――――――――――――
No. R 2 R a R 6 (Z) m1 mp (°C)
――――――――――――――――――――――――――――――――――
3-001 CH2 (G-3a) Me E-38a 2-OMe-5-F*
3-002 C(O)(G-3a) Me E-38a 2-OMe-5-F *
3-003 C(O)(G-22a) Me E-38a 2-OMe-5-F *
3-004 C(O)C(O)N(H)tBu Me E-38a 2-OMe-5-F *
3-005 C(O)OiBu Me E-38a 2-OMe-5-F*
3-006 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F*
3-007 CH2CH=CHClMe E-38a 2 -OMe-5-F*
3-008 C(O)C(=NOMe)Me Me E-38a 2-OMe-5-F *
3-009 CH2 (Ph-2-F)Me E-38a 2-OMe-5-F*
3-010 C(O)OCH2tBu Me E-38a 2 -OMe-5-F *
3-011 C(O)((G-22a)-2-Me) Me E-38a 2-OMe-5-F 149-151
3-012 C(O)(G-4a) Me E-38a 2-OMe-5-F 164-166
3-013 C(O)((G-3a)-3-Me) Me E-38a 2-OMe-5-F 141-144
3-014 C(O)Ph Me E-38a 2-OMe-5-F *
3-015 C(O)((G-22a)-2-Cl) Me E-38a 2-OMe-5-F *
3-016 C(O)((G-22a)-2-tBu) Me E-38a 2-OMe-5-F *
3-017 C(O)((G-3a)-5-Me) Me E-38a 2-OMe-5-F *
3-018 C(O)((G-3a)-5-Cl) Me E-38a 2-OMe-5-F *
3-019 C(O)cHex Me E-38a 2-OMe-5-F *
3-020 C(O)cPen Me E-38a 2-OMe-5-F *
3-021 C(O)CH(Et)2Me E-38a 2 -OMe-5-F *
3-022 CH2CH = CCl2Me E-38a 2 -OMe-5-F*
3-023 C(O)OcHex Me E-38a 2-OMe-5-F *
3-024 CH2 (G-3a) Et E-38a 2-OMe-5-F *
3-025 C(O)OiBu Et E-38a 2-OMe-5-F*
3-026 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-027 C(O)(G-3a)MeCH(Me)C(O)N(H)Me 2-OMe-5-F *
3-028 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-029 C(O)(G-22a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-030 C(O)(G-22a)MeCH(Me)C(O)N(H)Me 2-OMe-5-F *
3-031 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-032 CH2 (G-3a)Me(E-44a)-1-C(O)OMe2-OMe-5-F*
3-033 CH2 (G-3a)MeCH(Me)C(O)N(H)Me2-OMe-5-F 167-169
3-034 CH2CH=CHClMe(E-44a)-1-C(O)OMe2-OMe-5-F*
3-035 CH2CH=CHClMeCH(Me)C(O)N(H)Me2-OMe-5-F*
3-036 CH2 (Ph-2-F)Me(E-44a)-1-C(O)OMe2-OMe-5-F*
3-037 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-038 C(O)OiBu Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-039 CH2C(=NOMe)MeMe(E-44a)-1-C(O)OMe2-OMe-5-F*
3-040 CH2C(=NOMe)MeMeCH(Me)C(O)N(H)Me2-OMe-5-F 121-123
3-041 C(O)C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-042 C(O)C(=NOMe)MeMeCH(Me)C(O)N(H)Me 2-OMe-5-F *
3-043 C(O)C(O)N(H)tBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-044 C(O)OiBu Me (E-44a)-1-C(O)OMeH*
3-045 C(O)OiBuMeCH(Me)C(O)N(H)MeH*
3-046 C(O)OiBu Me E-38a H*
3-047 CH2C(=NOMe)MeMe(E-44a)-1-C(O)OMeH*
3-048 CH2C(=NOMe)MeMeCH(Me)C(O)N(H)MeH 145-149
3-049 CH2C(=NOMe)Me Me E-38a H*
3-050 CH2 (G-3a)Me(E-44a)-1-C(O)OMeH*
3-051 CH2 (G-3a)MeCH(Me)C(O)N(H)MeH*
3-052 CH2 (G-3a) Me E-38a H*
3-053 CH2CH=CHCl Me (E-44a)-1-C(O)OMe H 127-129
3-054 CH2CH=CHClMeCH(Me)C(O)N(H)MeH*
3-055 CH2CH=CHClMe E-38a H*
3-056 CH2 (Ph-2-F)Me(E-44a)-1-C(O)OMeH*
3-057 CH2 (Ph-2-F)MeCH(Me)C(O)N(H)MeH*
3-058 CH2 (Ph-2-F)MeE-38aH*
3-059 C(O)(G-3a)Me(E-44a)-1-C(O)OMeH*
3-060 C(O)(G-3a)MeCH(Me)C(O)N(H)MeH 243-245
3-061 C(O)(G-3a)MeE-38aH*
3-062 C(O)((G-3a)-3-Me)Me(E-44a)-1-C(O)OMeH*
3-063 C(O)((G-3a)-3-Me) Me CH(Me) C(O) N(H) Me H 219-221
3-064 C(O)((G-3a)-3-Me) Me E-38a H*
3-065 C(O)Ph Me (E-44a)-1-C(O)OMe H *
3-066 C(O)Ph Me CH(Me)C(O)N(H)Me H 227-229
3-067 C(O)Ph Me E-38a H*
3-068 C(O)C(O)N(H)tBuMe(E-44a)-1-C(O)OMeH*
3-069 C(O)C(O)N(H)tBuMeCH(Me)C(O)N(H)MeH*
3-070 C(O)C(=NOMe)Me(E-44a)-1-C(O)OMeH*
3-071 C(O)(G-4a)MeCH(Me)C(O)N(H)MeH 207-209
3-072 C(O)C(=NOMe)Me Me E-38a H*
3-073 C(O)(G-22a)Me(E-44a)-1-C(O)OMeH*
3-074 C(O)(G-22a) Me CH(Me) C(O) N(H) Me H 229-231
3-075 C(O)(G-22a)MeE-38aH*
3-076 CH2 (G-3a)Me E-38a 2-OMe*
3-077 CH2 (G-3a)Me(E-44a)-1-C(O)OMe2-OMe*
3-078 CH2CH=CHClMe E-38a 2 -OMe*
3-079 CH2CH=CHClMe(E-44a)-1-C(O)OMe2-OMe*
3-080 CH2 (Ph-2-F)Me E-38a 2-OMe*
3-081 CH2 (Ph-2-F)Me(E-44a)-1-C(O)OMe2-OMe*
3-082 CH2 (G-4a) Me E-38a 2-OMe*
3-083 CH2 (G-4a)Me(E-44a)-1-C(O)OMe2-OMe*
3-084 C(O)(G-22a) Me E-38a 2-OMe *
3-085 CH2C(=NOMe)Me Me E-38a 2-OMe*
3-086 CH2C(=NOMe)MeMe(E-44a)-1-C(O)OMe2-OMe*
3-087 C(O)OiBu Me E-38a 2-OMe *
3-088 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe *
3-089 C(O)(G-3a) Me E-38a 2-OMe *
3-090 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-091 C(O)((G-3a)-3-Me) Me E-38a 2-OMe *
3-092 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe *
3-093 C(O)(G-1a) Me E-38a 3-Cl *
3-094 C(O)(G-52a) Me E-38a 3-Cl *
3-095 C(O)iBu Me E-38a 3-Cl*
3-096 C(O)((G-53a)-6-Cl) Me E-38a 3-Cl *
3-097 C(O)(G-21a) Me E-38a 3-Cl *
3-098 C(O)((G-21a)-4-Me) Me E-38a 3-Cl 181-182
3-099 C(O)((G-17a)-1-Me) Me E-38a 3-Cl *
3-100 C(O)((G-16a)-1-Me) Me E-38a 3-Cl *
3-101 C(O)((G-15a)-1-Me) Me E-38a 3-Cl 184-186
3-102 C(O)((G-3a)-3-Cl) Me E-38a 3-Cl *
3-103 C(O)((G-52a)-5-Cl) Me E-38a 3-Cl *
3-104 C(O)((G-52a)-6-Cl) Me E-38a 3-Cl *
3-105 CH2 (G-3a)MeL-5a2-OMe-5-F*
3-106 CH2 (G-4a)MeL-5a2-OMe-5-F*
3-107 CH2PhMeL - 5a2-OMe-5-F*
3-108 CH2 (Ph-2-F)MeL-5a2-OMe-5-F*
3-109 CH2CH=CHClMeL-5a2-OMe-5-F*
3-110 C(O)C(O)OtBu Me L-5a 2-OMe-5-F *
3-111 CH2 (Ph-3-F)Me(E-44a)-1-C(O)OMe3-Cl*
3-112 CH2 (Ph-4-F)Me(E-44a)-1-C(O)OMe3-Cl*
3-113 CH2 (Ph-2-Me)Me(E-44a)-1-C(O)OMe3-Cl*
3-114 CH2 (Ph-2-OMe)Me(E-44a)-1-C(O)OMe3-Cl*
3-115CH2 (Ph-2,6 - F2)Me(E-44a)-1-C(O)OMe3-Cl*
3-116 CH2 ((G-3a)-3-Me)Me(E-44a)-1-C(O)OMe3-Cl*
3-117 CH2 (G-22a)Me(E-44a)-1-C(O)OMe3-Cl*
3-118 CH2 ((G-23a)-2-Cl)Me(E-44a)-1-C(O)OMe3-Cl*
3-119 CH2 ((G-53a)-6-Cl)Me(E-44a)-1-C(O)OMe3-Cl*
3-120 CH2cPrMe (E-44a)-1-C(O)OMe3-Cl*
3-121 CH2CH=CHClMe(E-44a)-1-C(O)OMe3-Cl*
3-122 C(O)(G-53a) Me E-38a 3-Cl*
3-123 CH2CH=CH2MeL - 5a2-OMe-5-F 124-126
3-124 CH2 (Ph-2,4-F2)MeL-5a2 - OMe-5-F 87-89
3-125 CH2C ( =NOMe)PhMeL-5a2-OMe-5-F*
3-126 CH2C(=NOMe)MeMeL-5a2-OMe-5-F*
3-127 C(O)(G-3a) Me L-5a 2-OMe-5-F 176-177
3-128C(O)(G-4a)MeL-5a2-OMe-5-F*
3-129 C(O)(G-22a) Me L-5a 2-OMe-5-F *
3-130 C(O)CH(Et) 2MeL -5a2-OMe-5-F*
3-131 C(O)Ph Me L-5a 2-OMe-5-F *
3-132 C(O)OiBu Me L-5a 2-OMe-5-F *
3-133 nPen Me L-5a 2-OMe-5-F*
3-134 CH2C(=NOMe)tBuMeL-5a2-OMe-5-F*
3-135 C(O)C(=NOMe)Me Me L-5a 2-OMe-5-F *
3-136 C(O)Ph Me E-38a 2-OMe *
3-137 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe *
3-138 C(O)(E-76a) Me L-5a 2-OMe-5-F *
3-139 C(O)(E-45a) Me L-5a 2-OMe-5-F *
3-140 C(O)N(Me)iPr Me L-5a 2-OMe-5-F *
3-141 C(O)N(Et) 2MeL -5a2-OMe-5-F 65-67
――――――――――――――――――――――――――――――――――
[Table 6]
No. R2 Ra R6 (Z)m1 m.p.(℃)
――――――――――――――――――――――――――――――――――
3-001 CH2(G-3a) Me E-38a 2-OMe-5-F *
3-002 C(O)(G-3a) Me E-38a 2-OMe-5-F *
3-003 C(O)(G-22a) Me E-38a 2-OMe-5-F *
3-004 C(O)C(O)N(H)tBu Me E-38a 2-OMe-5-F *
3-005 C(O)OiBu Me E-38a 2-OMe-5-F *
3-006 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F *
3-007 CH2CH=CHCl Me E-38a 2-OMe-5-F *
3-008 C(O)C(=NOMe)Me Me E-38a 2-OMe-5-F *
3-009 CH2(Ph-2-F) Me E-38a 2-OMe-5-F *
3-010 C(O)OCH2tBu Me E-38a 2-OMe-5-F *
3-011 C(O)((G-22a)-2-Me) Me E-38a 2-OMe-5-F 149-151
3-012 C(O)(G-4a) Me E-38a 2-OMe-5-F 164-166
3-013 C(O)((G-3a)-3-Me) Me E-38a 2-OMe-5-F 141-144
3-014 C(O)Ph Me E-38a 2-OMe-5-F *
3-015 C(O)((G-22a)-2-Cl) Me E-38a 2-OMe-5-F *
3-016 C(O)((G-22a)-2-tBu) Me E-38a 2-OMe-5-F *
3-017 C(O)((G-3a)-5-Me) Me E-38a 2-OMe-5-F *
3-018 C(O)((G-3a)-5-Cl) Me E-38a 2-OMe-5-F *
3-019 C(O)cHex Me E-38a 2-OMe-5-F *
3-020 C(O)cPen Me E-38a 2-OMe-5-F *
3-021 C(O)CH(Et)2 Me E-38a 2-OMe-5-F *
3-022 CH2CH=CCl2 Me E-38a 2-OMe-5-F *
3-023 C(O)OcHex Me E-38a 2-OMe-5-F *
3-024 CH2(G-3a) Et E-38a 2-OMe-5-F *
3-025 C(O)OiBu Et E-38a 2-OMe-5-F *
3-026 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-027 C(O)(G-3a) Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-028 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-029 C(O)(G-22a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-030 C(O)(G-22a) Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-031 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-032 CH2(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-033 CH2(G-3a) Me CH(Me)C(O)N(H)Me 2-OMe-5-F 167-169
3-034 CH2CH=CHCl Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-035 CH2CH=CHCl Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-036 CH2(Ph-2-F) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-037 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-038 C(O)OiBu Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-039 CH2C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-040 CH2C(=NOMe)Me Me CH(Me)C(O)N(H)Me 2-OMe-5-F 121-123
3-041 C(O)C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-042 C(O)C(=NOMe)Me Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-043 C(O)C(O)N(H)tBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-044 C(O)OiBu Me (E-44a)-1-C(O)OMe H *
3-045 C(O)OiBu Me CH(Me)C(O)N(H)Me H *
3-046 C(O)OiBu Me E-38a H *
3-047 CH2C(=NOMe)Me Me (E-44a)-1-C(O)OMe H *
3-048 CH2C(=NOMe)Me Me CH(Me)C(O)N(H)Me H 145-149
3-049 CH2C(=NOMe)Me Me E-38a H *
3-050 CH2(G-3a) Me (E-44a)-1-C(O)OMe H *
3-051 CH2(G-3a) Me CH(Me)C(O)N(H)Me H *
3-052 CH2(G-3a) Me E-38a H *
3-053 CH2CH=CHCl Me (E-44a)-1-C(O)OMe H 127-129
3-054 CH2CH=CHCl Me CH(Me)C(O)N(H)Me H *
3-055 CH2CH=CHCl Me E-38a H *
3-056 CH2(Ph-2-F) Me (E-44a)-1-C(O)OMe H *
3-057 CH2(Ph-2-F) Me CH(Me)C(O)N(H)Me H *
3-058 CH2(Ph-2-F) Me E-38a H *
3-059 C(O)(G-3a) Me (E-44a)-1-C(O)OMe H *
3-060 C(O)(G-3a) Me CH(Me)C(O)N(H)Me H 243-245
3-061 C(O)(G-3a) Me E-38a H *
3-062 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe H *
3-063 C(O)((G-3a)-3-Me) Me CH(Me)C(O)N(H)Me H 219-221
3-064 C(O)((G-3a)-3-Me) Me E-38a H *
3-065 C(O)Ph Me (E-44a)-1-C(O)OMe H *
3-066 C(O)Ph Me CH(Me)C(O)N(H)Me H 227-229
3-067 C(O)Ph Me E-38a H *
3-068 C(O)C(O)N(H)tBu Me (E-44a)-1-C(O)OMe H *
3-069 C(O)C(O)N(H)tBu Me CH(Me)C(O)N(H)Me H *
3-070 C(O)C(=NOMe)Me Me (E-44a)-1-C(O)OMe H *
3-071 C(O)(G-4a) Me CH(Me)C(O)N(H)Me H 207-209
3-072 C(O)C(=NOMe)Me Me E-38a H *
3-073 C(O)(G-22a) Me (E-44a)-1-C(O)OMe H *
3-074 C(O)(G-22a) Me CH(Me)C(O)N(H)Me H 229-231
3-075 C(O)(G-22a) Me E-38a H *
3-076 CH2(G-3a) Me E-38a 2-OMe *
3-077 CH2(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-078 CH2CH=CHCl Me E-38a 2-OMe *
3-079 CH2CH=CHCl Me (E-44a)-1-C(O)OMe 2-OMe *
3-080 CH2(Ph-2-F) Me E-38a 2-OMe *
3-081 CH2(Ph-2-F) Me (E-44a)-1-C(O)OMe 2-OMe *
3-082 CH2(G-4a) Me E-38a 2-OMe *
3-083 CH2(G-4a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-084 C(O)(G-22a) Me E-38a 2-OMe *
3-085 CH2C(=NOMe)Me Me E-38a 2-OMe *
3-086 CH2C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe *
3-087 C(O)OiBu Me E-38a 2-OMe *
3-088 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe *
3-089 C(O)(G-3a) Me E-38a 2-OMe *
3-090 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-091 C(O)((G-3a)-3-Me) Me E-38a 2-OMe *
3-092 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe *
3-093 C(O)(G-1a) Me E-38a 3-Cl *
3-094 C(O)(G-52a) Me E-38a 3-Cl *
3-095 C(O)iBu Me E-38a 3-Cl *
3-096 C(O)((G-53a)-6-Cl) Me E-38a 3-Cl *
3-097 C(O)(G-21a) Me E-38a 3-Cl *
3-098 C(O)((G-21a)-4-Me) Me E-38a 3-Cl 181-182
3-099 C(O)((G-17a)-1-Me) Me E-38a 3-Cl *
3-100 C(O)((G-16a)-1-Me) Me E-38a 3-Cl *
3-101 C(O)((G-15a)-1-Me) Me E-38a 3-Cl 184-186
3-102 C(O)((G-3a)-3-Cl) Me E-38a 3-Cl *
3-103 C(O)((G-52a)-5-Cl) Me E-38a 3-Cl *
3-104 C(O)((G-52a)-6-Cl) Me E-38a 3-Cl *
3-105 CH2(G-3a) Me L-5a 2-OMe-5-F *
3-106 CH2(G-4a) Me L-5a 2-OMe-5-F *
3-107 CH2Ph Me L-5a 2-OMe-5-F *
3-108 CH2(Ph-2-F) Me L-5a 2-OMe-5-F *
3-109 CH2CH=CHCl Me L-5a 2-OMe-5-F *
3-110 C(O)C(O)OtBu Me L-5a 2-OMe-5-F *
3-111 CH2(Ph-3-F) Me (E-44a)-1-C(O)OMe 3-Cl *
3-112 CH2(Ph-4-F) Me (E-44a)-1-C(O)OMe 3-Cl *
3-113 CH2(Ph-2-Me) Me (E-44a)-1-C(O)OMe 3-Cl *
3-114 CH2(Ph-2-OMe) Me (E-44a)-1-C(O)OMe 3-Cl *
3-115 CH2(Ph-2,6-F2) Me (E-44a)-1-C(O)OMe 3-Cl *
3-116 CH2((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 3-Cl *
3-117 CH2(G-22a) Me (E-44a)-1-C(O)OMe 3-Cl *
3-118 CH2((G-23a)-2-Cl) Me (E-44a)-1-C(O)OMe 3-Cl *
3-119 CH2((G-53a)-6-Cl) Me (E-44a)-1-C(O)OMe 3-Cl *
3-120 CH2cPr Me (E-44a)-1-C(O)OMe 3-Cl *
3-121 CH2CH=CHCl Me (E-44a)-1-C(O)OMe 3-Cl *
3-122 C(O)(G-53a) Me E-38a 3-Cl *
3-123 CH2CH=CH2 Me L-5a 2-OMe-5-F 124-126
3-124 CH2(Ph-2,4-F2) Me L-5a 2-OMe-5-F 87-89
3-125 CH2C(=NOMe)Ph Me L-5a 2-OMe-5-F *
3-126 CH2C(=NOMe)Me Me L-5a 2-OMe-5-F *
3-127 C(O)(G-3a) Me L-5a 2-OMe-5-F 176-177
3-128 C(O)(G-4a) Me L-5a 2-OMe-5-F *
3-129 C(O)(G-22a) Me L-5a 2-OMe-5-F *
3-130 C(O)CH(Et)2 Me L-5a 2-OMe-5-F *
3-131 C(O)Ph Me L-5a 2-OMe-5-F *
3-132 C(O)OiBu Me L-5a 2-OMe-5-F *
3-133 nPen Me L-5a 2-OMe-5-F *
3-134 CH2C(=NOMe)tBu Me L-5a 2-OMe-5-F *
3-135 C(O)C(=NOMe)Me Me L-5a 2-OMe-5-F *
3-136 C(O)Ph Me E-38a 2-OMe *
3-137 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe *
3-138 C(O)(E-76a) Me L-5a 2-OMe-5-F *
3-139 C(O)(E-45a) Me L-5a 2-OMe-5-F *
3-140 C(O)N(Me)iPr Me L-5a 2-OMe-5-F *
3-141 C(O)N(Et)2 Me L-5a 2-OMe-5-F 65-67
――――――――――――――――――――――――――――――――――
[第6表]
No. R 2 R a R 6 (Z) m1 mp (°C)
――――――――――――――――――――――――――――――――――
3-001 CH2 (G-3a) Me E-38a 2-OMe-5-F*
3-002 C(O)(G-3a) Me E-38a 2-OMe-5-F *
3-003 C(O)(G-22a) Me E-38a 2-OMe-5-F *
3-004 C(O)C(O)N(H)tBu Me E-38a 2-OMe-5-F *
3-005 C(O)OiBu Me E-38a 2-OMe-5-F*
3-006 CH2C(=NOMe)Me Me E-38a 2-OMe-5-F*
3-007 CH2CH=CHClMe E-38a 2 -OMe-5-F*
3-008 C(O)C(=NOMe)Me Me E-38a 2-OMe-5-F *
3-009 CH2 (Ph-2-F)Me E-38a 2-OMe-5-F*
3-010 C(O)OCH2tBu Me E-38a 2 -OMe-5-F *
3-011 C(O)((G-22a)-2-Me) Me E-38a 2-OMe-5-F 149-151
3-012 C(O)(G-4a) Me E-38a 2-OMe-5-F 164-166
3-013 C(O)((G-3a)-3-Me) Me E-38a 2-OMe-5-F 141-144
3-014 C(O)Ph Me E-38a 2-OMe-5-F *
3-015 C(O)((G-22a)-2-Cl) Me E-38a 2-OMe-5-F *
3-016 C(O)((G-22a)-2-tBu) Me E-38a 2-OMe-5-F *
3-017 C(O)((G-3a)-5-Me) Me E-38a 2-OMe-5-F *
3-018 C(O)((G-3a)-5-Cl) Me E-38a 2-OMe-5-F *
3-019 C(O)cHex Me E-38a 2-OMe-5-F *
3-020 C(O)cPen Me E-38a 2-OMe-5-F *
3-021 C(O)CH(Et)2Me E-38a 2 -OMe-5-F *
3-022 CH2CH = CCl2Me E-38a 2 -OMe-5-F*
3-023 C(O)OcHex Me E-38a 2-OMe-5-F *
3-024 CH2 (G-3a) Et E-38a 2-OMe-5-F *
3-025 C(O)OiBu Et E-38a 2-OMe-5-F*
3-026 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-027 C(O)(G-3a)MeCH(Me)C(O)N(H)Me 2-OMe-5-F *
3-028 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-029 C(O)(G-22a) Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-030 C(O)(G-22a)MeCH(Me)C(O)N(H)Me 2-OMe-5-F *
3-031 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-032 CH2 (G-3a)Me(E-44a)-1-C(O)OMe2-OMe-5-F*
3-033 CH2 (G-3a)MeCH(Me)C(O)N(H)Me2-OMe-5-F 167-169
3-034 CH2CH=CHClMe(E-44a)-1-C(O)OMe2-OMe-5-F*
3-035 CH2CH=CHClMeCH(Me)C(O)N(H)Me2-OMe-5-F*
3-036 CH2 (Ph-2-F)Me(E-44a)-1-C(O)OMe2-OMe-5-F*
3-037 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-038 C(O)OiBu Me CH(Me)C(O)N(H)Me 2-OMe-5-F *
3-039 CH2C(=NOMe)MeMe(E-44a)-1-C(O)OMe2-OMe-5-F*
3-040 CH2C(=NOMe)MeMeCH(Me)C(O)N(H)Me2-OMe-5-F 121-123
3-041 C(O)C(=NOMe)Me Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-042 C(O)C(=NOMe)MeMeCH(Me)C(O)N(H)Me 2-OMe-5-F *
3-043 C(O)C(O)N(H)tBu Me (E-44a)-1-C(O)OMe 2-OMe-5-F *
3-044 C(O)OiBu Me (E-44a)-1-C(O)OMeH*
3-045 C(O)OiBuMeCH(Me)C(O)N(H)MeH*
3-046 C(O)OiBu Me E-38a H*
3-047 CH2C(=NOMe)MeMe(E-44a)-1-C(O)OMeH*
3-048 CH2C(=NOMe)MeMeCH(Me)C(O)N(H)MeH 145-149
3-049 CH2C(=NOMe)Me Me E-38a H*
3-050 CH2 (G-3a)Me(E-44a)-1-C(O)OMeH*
3-051 CH2 (G-3a)MeCH(Me)C(O)N(H)MeH*
3-052 CH2 (G-3a) Me E-38a H*
3-053 CH2CH=CHCl Me (E-44a)-1-C(O)OMe H 127-129
3-054 CH2CH=CHClMeCH(Me)C(O)N(H)MeH*
3-055 CH2CH=CHClMe E-38a H*
3-056 CH2 (Ph-2-F)Me(E-44a)-1-C(O)OMeH*
3-057 CH2 (Ph-2-F)MeCH(Me)C(O)N(H)MeH*
3-058 CH2 (Ph-2-F)MeE-38aH*
3-059 C(O)(G-3a)Me(E-44a)-1-C(O)OMeH*
3-060 C(O)(G-3a)MeCH(Me)C(O)N(H)MeH 243-245
3-061 C(O)(G-3a)MeE-38aH*
3-062 C(O)((G-3a)-3-Me)Me(E-44a)-1-C(O)OMeH*
3-063 C(O)((G-3a)-3-Me) Me CH(Me) C(O) N(H) Me H 219-221
3-064 C(O)((G-3a)-3-Me) Me E-38a H*
3-065 C(O)Ph Me (E-44a)-1-C(O)OMe H *
3-066 C(O)Ph Me CH(Me)C(O)N(H)Me H 227-229
3-067 C(O)Ph Me E-38a H*
3-068 C(O)C(O)N(H)tBuMe(E-44a)-1-C(O)OMeH*
3-069 C(O)C(O)N(H)tBuMeCH(Me)C(O)N(H)MeH*
3-070 C(O)C(=NOMe)Me(E-44a)-1-C(O)OMeH*
3-071 C(O)(G-4a)MeCH(Me)C(O)N(H)MeH 207-209
3-072 C(O)C(=NOMe)Me Me E-38a H*
3-073 C(O)(G-22a)Me(E-44a)-1-C(O)OMeH*
3-074 C(O)(G-22a) Me CH(Me) C(O) N(H) Me H 229-231
3-075 C(O)(G-22a)MeE-38aH*
3-076 CH2 (G-3a)Me E-38a 2-OMe*
3-077 CH2 (G-3a)Me(E-44a)-1-C(O)OMe2-OMe*
3-078 CH2CH=CHClMe E-38a 2 -OMe*
3-079 CH2CH=CHClMe(E-44a)-1-C(O)OMe2-OMe*
3-080 CH2 (Ph-2-F)Me E-38a 2-OMe*
3-081 CH2 (Ph-2-F)Me(E-44a)-1-C(O)OMe2-OMe*
3-082 CH2 (G-4a) Me E-38a 2-OMe*
3-083 CH2 (G-4a)Me(E-44a)-1-C(O)OMe2-OMe*
3-084 C(O)(G-22a) Me E-38a 2-OMe *
3-085 CH2C(=NOMe)Me Me E-38a 2-OMe*
3-086 CH2C(=NOMe)MeMe(E-44a)-1-C(O)OMe2-OMe*
3-087 C(O)OiBu Me E-38a 2-OMe *
3-088 C(O)OiBu Me (E-44a)-1-C(O)OMe 2-OMe *
3-089 C(O)(G-3a) Me E-38a 2-OMe *
3-090 C(O)(G-3a) Me (E-44a)-1-C(O)OMe 2-OMe *
3-091 C(O)((G-3a)-3-Me) Me E-38a 2-OMe *
3-092 C(O)((G-3a)-3-Me) Me (E-44a)-1-C(O)OMe 2-OMe *
3-093 C(O)(G-1a) Me E-38a 3-Cl *
3-094 C(O)(G-52a) Me E-38a 3-Cl *
3-095 C(O)iBu Me E-38a 3-Cl*
3-096 C(O)((G-53a)-6-Cl) Me E-38a 3-Cl *
3-097 C(O)(G-21a) Me E-38a 3-Cl *
3-098 C(O)((G-21a)-4-Me) Me E-38a 3-Cl 181-182
3-099 C(O)((G-17a)-1-Me) Me E-38a 3-Cl *
3-100 C(O)((G-16a)-1-Me) Me E-38a 3-Cl *
3-101 C(O)((G-15a)-1-Me) Me E-38a 3-Cl 184-186
3-102 C(O)((G-3a)-3-Cl) Me E-38a 3-Cl *
3-103 C(O)((G-52a)-5-Cl) Me E-38a 3-Cl *
3-104 C(O)((G-52a)-6-Cl) Me E-38a 3-Cl *
3-105 CH2 (G-3a)MeL-5a2-OMe-5-F*
3-106 CH2 (G-4a)MeL-5a2-OMe-5-F*
3-107 CH2PhMeL - 5a2-OMe-5-F*
3-108 CH2 (Ph-2-F)MeL-5a2-OMe-5-F*
3-109 CH2CH=CHClMeL-5a2-OMe-5-F*
3-110 C(O)C(O)OtBu Me L-5a 2-OMe-5-F *
3-111 CH2 (Ph-3-F)Me(E-44a)-1-C(O)OMe3-Cl*
3-112 CH2 (Ph-4-F)Me(E-44a)-1-C(O)OMe3-Cl*
3-113 CH2 (Ph-2-Me)Me(E-44a)-1-C(O)OMe3-Cl*
3-114 CH2 (Ph-2-OMe)Me(E-44a)-1-C(O)OMe3-Cl*
3-115CH2 (Ph-2,6 - F2)Me(E-44a)-1-C(O)OMe3-Cl*
3-116 CH2 ((G-3a)-3-Me)Me(E-44a)-1-C(O)OMe3-Cl*
3-117 CH2 (G-22a)Me(E-44a)-1-C(O)OMe3-Cl*
3-118 CH2 ((G-23a)-2-Cl)Me(E-44a)-1-C(O)OMe3-Cl*
3-119 CH2 ((G-53a)-6-Cl)Me(E-44a)-1-C(O)OMe3-Cl*
3-120 CH2cPrMe (E-44a)-1-C(O)OMe3-Cl*
3-121 CH2CH=CHClMe(E-44a)-1-C(O)OMe3-Cl*
3-122 C(O)(G-53a) Me E-38a 3-Cl*
3-123 CH2CH=CH2MeL - 5a2-OMe-5-F 124-126
3-124 CH2 (Ph-2,4-F2)MeL-5a2 - OMe-5-F 87-89
3-125 CH2C ( =NOMe)PhMeL-5a2-OMe-5-F*
3-126 CH2C(=NOMe)MeMeL-5a2-OMe-5-F*
3-127 C(O)(G-3a) Me L-5a 2-OMe-5-F 176-177
3-128C(O)(G-4a)MeL-5a2-OMe-5-F*
3-129 C(O)(G-22a) Me L-5a 2-OMe-5-F *
3-130 C(O)CH(Et) 2MeL -5a2-OMe-5-F*
3-131 C(O)Ph Me L-5a 2-OMe-5-F *
3-132 C(O)OiBu Me L-5a 2-OMe-5-F *
3-133 nPen Me L-5a 2-OMe-5-F*
3-134 CH2C(=NOMe)tBuMeL-5a2-OMe-5-F*
3-135 C(O)C(=NOMe)Me Me L-5a 2-OMe-5-F *
3-136 C(O)Ph Me E-38a 2-OMe *
3-137 C(O)Ph Me (E-44a)-1-C(O)OMe 2-OMe *
3-138 C(O)(E-76a) Me L-5a 2-OMe-5-F *
3-139 C(O)(E-45a) Me L-5a 2-OMe-5-F *
3-140 C(O)N(Me)iPr Me L-5a 2-OMe-5-F *
3-141 C(O)N(Et) 2MeL -5a2-OMe-5-F 65-67
――――――――――――――――――――――――――――――――――
[Table 6]
――――――――――――――――――――――――――――――――
No. R2 R4 R6 (Z)m1 m.p.(℃)
――――――――――――――――――――――――――――――――
4-001 CH2C(=NOMe)Me L-3 E-38a 2-OMe-5-F *
4-002 C(O)(G-3a) L-3 E-38a 2-OMe-5-F *
4-003 CH2(G-3a) SMe E-38a 2-OMe-5-F *
4-004 CH2(G-3a) S(O)Me E-38a 2-OMe-5-F *
4-005 CH2(G-3a) S(O)2Me E-38a 2-OMe-5-F 208-210
4-006 C(O)(G-3a) L-4 E-38a 2-OMe-5-F *
4-007 CH2(G-3a) L-4 E-38a 2-OMe-5-F *
4-008 C(O)OiBu CH2SMe E-38a 2-OMe-5-F 70-72
4-009 C(O)OiBu CH2S(O)Me E-38a 2-OMe-5-F 100-102
4-010 C(O)OiBu CH2S(O)2Me E-38a 2-OMe-5-F 119-121
4-011 CH2(Ph-2-F) L-2 E-38a 3-Cl *
――――――――――――――――――――――――――――――――
第3表から第6表に示す本発明化合物のうち、融点の記載のない化合物の1H-NMRデータを第7表に示す。なお、下記データは、重クロロホルム中で測定したものである。 ――――――――――――――――――――――――――――――――
No. R2 R4 R6 (Z) m1 mp (°C)
――――――――――――――――――――――――――――――――
4-001 CH2C(=NOMe)MeL-3E-38a2-OMe-5-F*
4-002 C(O)(G-3a) L-3 E-38a 2-OMe-5-F *
4-003 CH2 (G-3a) SMe E-38a 2-OMe-5-F*
4-004 CH2 (G-3a)S(O)Me E-38a 2-OMe-5-F*
4-005 CH2 (G-3a)S(O)2Me E-38a 2 -OMe-5-F 208-210
4-006 C(O)(G-3a) L-4 E-38a 2-OMe-5-F *
4-007 CH2 (G-3a) L-4 E-38a 2-OMe-5-F *
4-008 C(O)OiBu CH2SMe E-38a 2 -OMe-5-F 70-72
4-009 C(O)OiBu CH2S(O)Me E-38a 2 -OMe-5-F 100-102
4-010 C(O) OiBu CH2S(O)2Me E-38a 2 -OMe-5-F 119-121
4-011 CH2 (Ph-2-F)L-2 E-38a 3-Cl*
――――――――――――――――――――――――――――――――
Among the compounds of the present invention shown in Tables 3 to 6, Table 7 shows the 1 H-NMR data of compounds with no description of melting point. The data below are those measured in deuterated chloroform.
No. R2 R4 R6 (Z)m1 m.p.(℃)
――――――――――――――――――――――――――――――――
4-001 CH2C(=NOMe)Me L-3 E-38a 2-OMe-5-F *
4-002 C(O)(G-3a) L-3 E-38a 2-OMe-5-F *
4-003 CH2(G-3a) SMe E-38a 2-OMe-5-F *
4-004 CH2(G-3a) S(O)Me E-38a 2-OMe-5-F *
4-005 CH2(G-3a) S(O)2Me E-38a 2-OMe-5-F 208-210
4-006 C(O)(G-3a) L-4 E-38a 2-OMe-5-F *
4-007 CH2(G-3a) L-4 E-38a 2-OMe-5-F *
4-008 C(O)OiBu CH2SMe E-38a 2-OMe-5-F 70-72
4-009 C(O)OiBu CH2S(O)Me E-38a 2-OMe-5-F 100-102
4-010 C(O)OiBu CH2S(O)2Me E-38a 2-OMe-5-F 119-121
4-011 CH2(Ph-2-F) L-2 E-38a 3-Cl *
――――――――――――――――――――――――――――――――
第3表から第6表に示す本発明化合物のうち、融点の記載のない化合物の1H-NMRデータを第7表に示す。なお、下記データは、重クロロホルム中で測定したものである。 ――――――――――――――――――――――――――――――――
No. R2 R4 R6 (Z) m1 mp (°C)
――――――――――――――――――――――――――――――――
4-001 CH2C(=NOMe)MeL-3E-38a2-OMe-5-F*
4-002 C(O)(G-3a) L-3 E-38a 2-OMe-5-F *
4-003 CH2 (G-3a) SMe E-38a 2-OMe-5-F*
4-004 CH2 (G-3a)S(O)Me E-38a 2-OMe-5-F*
4-005 CH2 (G-3a)S(O)2Me E-38a 2 -OMe-5-F 208-210
4-006 C(O)(G-3a) L-4 E-38a 2-OMe-5-F *
4-007 CH2 (G-3a) L-4 E-38a 2-OMe-5-F *
4-008 C(O)OiBu CH2SMe E-38a 2 -OMe-5-F 70-72
4-009 C(O)OiBu CH2S(O)Me E-38a 2 -OMe-5-F 100-102
4-010 C(O) OiBu CH2S(O)2Me E-38a 2 -OMe-5-F 119-121
4-011 CH2 (Ph-2-F)L-2 E-38a 3-Cl*
――――――――――――――――――――――――――――――――
Among the compounds of the present invention shown in Tables 3 to 6, Table 7 shows the 1 H-NMR data of compounds with no description of melting point. The data below are those measured in deuterated chloroform.
[第7表]
――――――――――――――――――――――――――――――――――
No. 1H-NMR
――――――――――――――――――――――――――――――――――
1-001: δ7.26-7.19 (m, 1H), 7.16-7.00 (m, 1H), 6.99-6.85 (m, 1H), 6.10&5.94 (s, 1H), 4.52-4.35 (m, 2H), 4.07-3.86 (m, 6H), 3.76-3.61 (m, 2H), 3.40-3.23 (m, 5H), 2.84&2.82 (s, 3H), 1.81-1.48 (m, 13H)。
1-013: δ7.48-7.35 (m, 2H), 7.35-7.10 (m, 3H), 7.08-6.99 (m, 1H), 6.98-6.85 (m, 1H), 6.12 (s, 1H), 4.74-4.55 (m, 2H), 4.50-4.38 (m, 2H), 4.07-3.93 (m, 3H), 3.73-3.59 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H), 2.83 (s, 3H), 1.81-1.46 (m, 4H)。
1-014: δ7.51-7.39 (m, 2H), 7.25-7.16 (m, 1H), 7.08-6.84 (m, 4H), 5.84 (s, 1H), 4.74-4.57 (m, 2H), 4.49-4.35 (m, 2H), 4.08-3.87 (m, 6H), 3.73-3.56 (m, 2H), 3.39-3.22 (m, 2H), 3.01 (s, 3H), 2.82 (s, 3H), 1.80-1.46 (m, 4H)。
1-016: δ7.47-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.11 (m, 1H), 6.14 (s, 1H), 4.49-4.36 (m, 2H), 4.06-3.96 (m, 3H), 3.90-3.76 (m, 5H), 3.74-3.61 (m, 2H), 3.40-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.85-1.50 (m, 4H)。
1-017: δ7.29-7.37 (m, 2H), 7.19-7.13 (m, 2H), 7.05-6.90 (m, 3H), 5.85 (s, 1H), 4.65-4.49 (m, 2H), 4.45-4.35 (m, 2H), 4.06-3.97 (m, 2H), 3.96-3.86 (m, 4H), 3.75-3.55 (m, 2H), 3.40-3.20 (m, 2H), 3.10 (s, 3H), 2.78 (s, 3H), 1.80-1.45 (m, 4H)。
1-018: δ7.45-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.10 (m, 3H), 7.00-6.92 (m, 1H), 6.13 (s, 1H), 4.64-4.48 (m, 2H), 4.47-4.35 (m, 2H), 4.05-3.95 (m, 3H), 3.76-3.60 (m, 2H), 3.38-3.25 (m, 2H), 3.08 (s, 3H), 2.79 (s, 3H), 1.85-1.50 (m, 4H)。
1-025: δ8.56-8.52 (m, 1H), 8.34-8.29 (m, 1H), 7.50-7.38 (m, 2H), 7.05-6.94 (m, 2H), 5.85 (s, 1H), 4.49-4.35 (m, 2H), 4.08-3.88 (m, 6H), 3.80-3.55 (m, 2H), 3.48 (s, 3H), 3.40-3.20 (m, 2H), 2.77 (s, 3H), 1.80-1.45 (m, 4H)。
1-026: δ8.60-8.55 (m, 1H), 8.35-8.30 (m, 1H), 7.47-7.34 (m, 2H), 7.32-7.24 (m, 1H), 7.21-7.12 (m, 1H), 6.12 (s, 1H), 4.50-4.39 (m, 2H), 4.10-3.95 (m, 3H), 3.82-3.60 (m, 2H), 3.47 (s, 3H), 3.40-3.20 (m, 2H), 2.77 (s, 3H), 1.86-1.43 (m, 4H)。
1-027: δ7.50-7.40 (m, 2H), 7.10-6.95 (m, 2H), 6.91&5.84 (s, 1H), 4.50-4.35 (m, 2H), 4.08-3.75 (m, 8H), 3.73-3.59 (m, 2H), 3.40-3.27 (s, 5H), 2.82 (s, 3H), 2.05-1.45 (m, 5H), 1.02-0.78 (m, 6H)。
1-028: δ7.47-7.35 (m, 2H), 7.32-7.25 (m, 1H), 7.23-7.13 (m, 1H), 6.17&6.11 (s, 1H), 4.50-4.37 (m, 2H), 4.10-3.75 (m, 5H), 3.75-3.61 (m, 2H), 3.40-3.20 (m, 5H), 2.82 (s, 3H), 2.05-1.50 (m, 5H), 1.01-0.78 (m, 6H)。
1-031: δ7.25-7.19 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 5.98 (s, 1H), 4.48-4.35 (m, 2H), 4.06-3.96 (m, 2H), 3.96-3.61 (m, 12H), 3.48-3.30 (m, 2H), 3.28-3.11 (m, 2H), 2.95 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.70-1.48 (m, 4H)。
1-038: δ7.24-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.00&5.92 (s, 1H), 4.50-4.36 (m, 2H), 4.08-3.88 (m, 8H), 3.63 (s, 3H), 3.50-3.12 (m, 7H), 2.81 (s, 3H), 2.05-1.48 (m, 5H), 1.01-0.77 (m, 6H)。
1-042: δ7.61-7.55 (m, 2H), 7.48-7.41 (m, 3H), 6.08 (s, 1H), 4.47-4.38 (m, 2H), 4.10-3.96 (m, 3H), 3.91-3.77 (m, 2H), 3.80 (s, 3H), 3.71-3.60 (m, 2H), 3.39-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.05 (s, 3H), 1.82-1.50 (m, 4H)。
1-046: δ7.62-7.55 (m, 2H), 7.50-7.40 (m, 3H), 6.06 (s, 1H), 4.49-4.34 (m, 2H), 4.08-3.97 (m, 3H), 3.91-3.76 (m, 2H), 3.79 (s, 3H), 3.63 (s, 3H), 3.49-3.33 (m, 2H), 3.25-3.09 (m, 2H), 2.95 (s, 3H), 2.83 (s, 3H), 2.05 (s, 3H), 1.77-1.47 (m, 4H)。
1-047: δ7.60-7.54 (m, 2H), 7.49-7.41 (m, 3H), 6.28-6.21 (m, 1H), 6.10-5.99 (m, 1H), 6.03 (s, 1H), 4.48-4.39 (m, 2H), 4.09-3.82 (m, 4H), 3.73-3.65 (m, 1H), 3.62 (s, 3H), 3.52-3.38 (m, 2H), 3.20-3.05 (m, 2H), 2.97 (s, 3H), 2.82 (s, 3H), 1.77-1.45 (m, 4H)。
1-059: δ8.60-8.50 (m, 1H), 8.35-8.30 (m, 1H), 7.60-7.52 (m, 1H), 7.50-7.34 (m, 3H), 6.11 (s, 1H), 4.50-4.37 (m, 2H), 4.10-3.89 (m, 3H), 3.80-3.60 (m, 2H), 3.46 (s, 3H), 3.40-3.15 (m, 2H), 2.77 (s, 3H), 1.90-1.40 (m, 4H)。
1-063: δ7.25-7.20 (m, 1H), 7.18-7.09 (m, 1H), 6.96-6.89 (m, 1H), 6.08&5.98 (s, 1H), 4.50-4.38 (m, 2H), 4.20-3.88 (m, 8H), 3.73-3.60 (m, 2H), 3.38-3.29 (m, 5H), 2.83&2.82 (s, 3H), 1.80-1.50 (m, 6H), 1.03-0.80 (m, 3H)。
1-064: δ7.60-7.58 (m, 1H), 7.50-7.36 (m, 3H), 7.24-7.20 (m, 1H), 7.06-7.03 (m, 1H), 6.95-6.90 (m, 1H), 6.11 (s, 1H), 4.72-4.57 (m, 2H), 4.47-4.39 (m, 2H), 4.08-3.92 (m, 3H), 3.71-3.59 (m, 2H), 3.38-3.24 (m, 2H), 3.01 (s, 3H), 2.83 (s, 3H), 1.80-1.45 (m, 4H)。
1-065: δ7.62-7.57 (m, 1H), 7.52-7.37 (m, 3H), 6.30-6.24 (m, 1H), 6.15-5.94 (m, 2H), 4.49-4.40 (m, 2H), 4.06-3.84 (m, 5H), 3.72-3.62 (m, 2H), 3.38-3.29 (m, 2H), 2.98 (s, 3H), 2.83 (s, 3H), 1.80-1.50 (m, 4H)。
1-066: δ7.76-7.68 (m, 1H), 7.62-7.58 (m, 1H), 7.52-7.30 (m, 3H), 7.25-7.19 (m, 1H), 7.16-6.95 (m, 2H), 6.13 (s, 1H), 4.54-4.38 (m, 4H), 4.06-3.90 (m, 3H), 3.70-3.60 (m, 2H), 3.39-3.25 (m, 2H), 2.99 (s, 3H), 2.88&2.83 (s, 3H), 1.80-1.50 (m, 4H)。
1-067: δ7.24-7.03 (m, 2H), 6.95-6.70 (m, 1H), 6.05 & 5.90 (s, 1H), 4.49-4.36 (m, 2H), 4.10-3.95 (m, 2H), 3.90 & 3.89 (s, 3H), 3.85-3.72 (m, 1H), 3.30 & 3.25 (s, 3H), 2.84 & 2.82 (s, 3H), 2.75-2.51 (m, 2H), 2.40-2.20 (m, 2H), 2.06-1.66 (m, 4H), 1.53 & 1.41 (s, 9H)。
1-068: δ7.29-7.20 (m, 1H), 7.16-7.06 (m, 1H), 6.94-6.84 (m, 1H), 6.17-5.81 (m, 1H), 4.73-4.61 (m, 1H), 4.47-4.34 (m, 2H), 4.08-3.97 (m, 2H), 3.92-3.84 (m, 3H), 3.38-3.22 (m, 6H), 3.05-2.97 (m, 3H), 2.86-2.77 (m, 3H), 1.56-1.17 (m, 12H)。
1-069: δ7.59-7.38 (m, 1H), 7.17-7.05 (m, 1H), 6.94-6.85 (m, 1H), 6.29-5.88 (m, 1H), 4.47-4.32 (m, 3H), 4.07-3.96 (m, 2H), 3.93-3.87 (m, 3H), 3.40-3.04 (m, 5H), 2.86-2.71 (m, 6H), 2.20-2.00 (m, 2H), 1.57-1.34 (m, 9H)。
1-070: δ7.27-7.20 (m, 1H), 7.16-7.03 (m, 1H), 6.96-6.86 (m, 1H), 6.09 & 5.94 (s, 1H), 4.49-4.36 (m, 2H), 4.10-3.96 (m, 2H), 3.90 & 3.89 (s, 3H), 3.74-3.62 (m, 1H), 3.29 & 3.24 (s, 3H), 2.84 & 2.82 (s, 3H), 1.74-1.01 (m, 19H)。
1-071: δ7.28-7.18 (m, 1H), 7.16-7.04 (m, 1H), 6.94-6.86 (m, 1H), 6.10-5.89 (m, 1H), 4.48-4.37 (m, 2H), 4.08-3.98 (m, 2H), 3.92-3.86 (m, 3H), 3.82-3.68 (m, 1H), 3.30-3.06 (m, 7H), 2.85-2.78 (m, 3H), 1.86-1.13 (m, 17H)。
1-072: δ7.30-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.16-5.87 (m, 1H), 4.50-4.37 (m, 3H), 4.09-3.94 (m, 2H), 3.94-3.86 (m, 3H), 3.73-3.33 (m, 4H), 3.30-3.21 (m, 3H), 2.86-2.79 (m, 3H), 2.14-1.97 (m, 3H), 1.67-1.19 (m, 13H)。
1-073: δ7.27-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.17-5.82 (m, 1H), 4.48-4.37 (m, 2H), 4.09-3.94 (m, 3H), 3.93-3.87 (m, 3H), 3.58-3.08 (m, 7H), 2.85-2.77 (m, 3H), 2.34-2.18 (m, 2H), 1.72-1.34 (m, 13H), 1.13-1.03 (m, 3H)。
1-078: δ7.50-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.95-6.87 (m, 1H), 5.97-5.85 (m, 1H), 4.49-4.36 (m, 2H), 4.09-3.94 (m, 3H), 3.93-3.88 (m, 3H), 3.77-3.73 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.78 (m, 3H), 2.43-2.15 (m, 4H), 1.82-1.34 (m, 13H)。
1-079: δ7.48-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.94-6.88 (m, 1H), 5.97 & 5.86 (s, 1H), 4.50-4.37 (m, 2H), 4.09-3.87 (m, 3H), 3.91 & 3.90 (s, 3H), 3.62 (s, 3H), 3.50-3.11 (m, 4H), 3.28 & 3.23 (s, 3H), 2.85-2.78 (m, 3H), 1.72-1.23 (m, 13H)。
1-086: δ7.28-7.07 (m, 2H), 6.98-6.84 (m, 1H), 6.09-5.88 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.22 (m, 12H), 2.89-2.77 (m, 3H), 2.71-1.95 (m, 5H), 1.91-1.36 (m, 4H), 1.10-0.76 (m, 10H)。
1-089: δ7.28-7.20 (m, 1H), 7.18-7.07 (m, 1H), 6.97-6.87 (m, 1H), 6.05-5.90 (m, 1H), 4.50-4.36 (m, 2H), 4.10-3.94 (m, 5H), 3.93-3.88 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.79 (m, 3H), 2.46-1.93 (m, 4H), 1.79-1.62 (m, 4H), 1.55-1.36 (m, 9H), 1.22-1.14 (m, 3H)。
1-090: δ7.41-7.28 (m, 1H), 7.28-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.04-5.89 (m, 1H), 4.49-4.36 (m, 2H), 4.10-3.96 (m, 3H), 3.93-3.86 (m, 3H), 3.29-3.19 (m, 3H), 2.85-2.78 (m, 3H), 2.48-1.95 (m, 4H), 1.82-1.61 (m, 4H), 1.54-1.35 (m, 9H)。
1-091: δ7.25-7.03 (m, 2H), 6.98-6.81 (m, 1H), 6.10-5.87 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.87 (m, 6H), 3.62-3.56 (m, 3H), 3.32-3.22 (m, 3H), 2.86-2.79 (m, 3H), 2.28-1.17 (m, 18H)。
1-092: δ7.33-7.20 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 5.98 (s, 1H), 4.52-4.37 (m, 4H), 4.07-3.95 (m, 3H), 3.93-3.72 (m, 8H), 2.96-2.90 (m, 3H), 2.83-2.79 (m, 3H), 2.40-1.87 (m, 10H), 1.79-1.59 (m, 4H)。
1-093: δ7.28-7.20 (m, 1H), 7.15-7.03 (m, 1H), 6.95-6.86 (m, 1H), 6.19-5.89 (m, 1H), 4.50-4.35 (m, 3H), 4.09-3.94 (m, 4H), 3.93-3.81 (m, 3H), 3.80-3.71 (m, 3H), 3.70-3.59 (m, 1H), 3.04-2.93 (m, 3H), 2.84-2.69 (m, 3H), 2.47-1.94 (m, 7H), 1.79-1.56 (m, 4H)。
1-094: δ7.29-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.87 (m, 1H), 4.49-4.35 (m, 2H), 4.17-3.84 (m, 8H), 3.56-3.03 (m, 7H), 2.84-2.76 (m, 3H), 1.76-1.14 (m, 16H)。
1-096: δ7.29-7.08 (m, 2H), 6.96-6.86 (m, 1H), 5.96 (s, 1H), 4.49-4.39 (m, 2H), 4.09-3.98 (m, 3H), 3.90 (s, 3H), 3.41-2.73 (m, 10H), 2.68 (s, 3H), 1.88-1.65 (m, 4H), 1.57-1.49 (m, 9H)。
1-100: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.02-5.91 (m, 1H), 4.49-4.38 (m, 2H), 4.17-3.94 (m, 4H), 3.92-3.87 (m, 3H), 3.79-3.69 (m, 4H), 3.35-3.26 (m, 3H), 2.81 (s, 3H), 2.42-1.93 (m, 4H), 1.89-1.53 (m, 4H), 1.01-0.74 (m, 7H)。
1-102: δ7.56-7.49 (m, 2H), 7.36-7.19 (m, 4H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.01-5.96 (m, 1H), 4.49-4.35 (m, 4H), 4.07-3.89 (m, 3H), 3.91 (s, 3H), 3.75-3.71 (m, 3H), 2.92 (s, 3H), 2.83 (s, 3H), 2.40-1.91 (m, 4H), 1.76-1.51 (m, 4H)。
1-105: δ7.28-7.19 (m, 1H), 7.17-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.00-5.96 (m, 1H), 4.47-4.38 (m, 2H), 4.07-3.70 (m, 14H), 2.96-2.91 (m, 3H), 2.84-2.81 (m, 3H), 2.52-1.59 (m, 11H)。
1-106: δ7.28-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.29-6.20 (m, 1H), 6.10-5.93 (m, 2H), 4.48-4.37 (m, 2H), 4.07-3.81 (m, 5H), 3.91 (s, 3H), 3.75 (s, 3H), 2.96 (s, 3H), 2.81 (s, 3H), 2.39-1.94 (m, 4H), 1.78-1.60 (m, 4H)。
1-107: δ7.78-7.68 (m, 1H), 7.28-6.86 (m, 6H), 6.00-5.94 (m, 1H), 4.55-4.36 (m, 4H), 4.08-3.86 (m, 3H), 3.91 (s, 3H), 3.76-3.71 (m, 3H), 2.96 (s, 3H), 2.82 (s, 3H), 2.38-1.92 (m, 4H), 1.76-1.53 (m, 4H)。
1-108: δ7.29-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.04-5.85 (m, 1H), 4.50-4.39 (m, 2H), 4.18-3.94 (m, 3H), 3.94-3.87 (m, 3H), 3.81-3.71 (m, 3H), 3.60-3.47 (m, 3H), 3.38-3.33 (m, 3H), 2.84-2.79 (m, 3H), 2.52-1.91 (m, 7H), 1.84-1.54 (m, 4H)。
1-109: δ7.25-7.08 (m, 2H), 7.04-6.88 (m, 1H), 6.07-5.88 (m, 1H), 4.49-4.39 (m, 2H), 4.08-3.88 (m, 6H), 3.32-2.94 (m, 7H), 2.85-2.80 (m, 3H), 2.71 (s, 6H), 1.81-1.38 (m, 13H)。
2-003: δ7.24-7.15 (m, 1H), 7.15-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.93 (s, 1H), 3.98-3.87 (m, 4H), 3.78-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.54&2.53 (s, 3H), 2.12&2.11 (s, 3H), 1.80-1.35 (m, 13H)。
2-004: δ7.24-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.94 (s, 1H), 3.98-3.87 (m, 4H), 3.75-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.53&2.51 (s, 3H), 1.82-1.35 (m, 14H), 1.00-0.80 (m, 4H)。
2-005: δ7.60-7.49 (m, 2H), 7.40-7.05 (m, 5H), 6.95-6.83 (m, 1H), 6.08-5.98 (m, 1H), 4.50-4.37 (m, 2H), 3.98-3.84 (m, 4H), 3.70-3.51 (m, 2H), 3.39-3.22 (m, 2H), 3.00-2.89 (m, 3H), 2.54 (s, 3H), 2.11 (s, 3H), 1.75-1.42 (m, 4H)。
2-006: δ7.78-7.70 (m, 1H), 7.27-7.05 (m, 4H), 7.03-6.85 (m, 2H), 6.01 (s, 1H), 4.55-4.40 (m, 2H), 4.00-3.85 (m, 4H), 3.69-3.50 (m, 2H), 3.39-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.79-1.45 (m, 4H)。
2-007: δ7.59-7.49 (m, 2H), 7.38-7.09 (m, 5H), 6.95-6.88 (m, 1H), 5.99 (s, 1H), 4.49-4.35 (m, 2H), 3.95-3.83 (m, 4H), 3.70-3.52 (m, 2H), 3.48 (s, 1H), 3.39-3.21 (m, 2H), 2.94 (s, 3H), 2.59 (s, 3H), 1.88-1.42 (m, 4H)。
2-008: δ7.70-7.62 (m, 1H), 7.57-7.10 (m, 6H), 6.98-6.84 (m, 1H), 6.11&5.77 (s, 1H), 4.05-3.78 (m, 4H), 3.75-3.51 (m, 2H), 3.51&3.48 (s, 1H), 3.41-3.12 (m, 5H), 2.61&2.53 (s, 3H), 1.82-1.18 (m, 4H)。
2-011: δ7.70-7.59 (m, 1H), 7.52-7.42 (m, 1H), 7.29-7.07 (m, 2H), 6.95-6.86 (m, 1H), 6.10-5.92 (m, 1H), 4.04-3.83 (m, 4H), 3.80-3.55 (m, 2H), 3.49 (s, 3H), 3.44-3.18 (m, 2H), 2.58-2.45 (m, 3H), 2.13 (s, 3H), 1.82-1.37 (m, 4H)。
2-012: δ7.29-7.05 (m, 2H), 6.95-6.85 (m, 1H), 6.07-5.94 (m, 1H), 3.96-3.75 (m, 9H), 3.72-3.53 (m, 2H), 3.41-3.28 (m, 2H), 3.00-2.89 (m, 3H), 2.64-2.46 (m, 3H), 2.16-2.11 (m, 3H), 2.09-2.00 (m, 3H), 1.78-1.49 (m, 4H)。
2-013: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.91 (m, 1H), 4.06-3.72 (m, 6H), 3.71-3.58 (m, 2H), 3.41-3.26 (m, 5H), 2.55-2.45 (m, 3H), 2.17-2.06 (m, 3H), 2.05-1.80 (m, 1H), 1.76-1.45 (m, 4H), 1.07-0.70 (m, 6H)。
2-014: δ7.71-7.41 (m, 3H), 7.38-7.09 (m, 4H), 6.98-6.85 (m, 1H), 6.12&5.78 (s, 1H), 4.02-3.79 (m, 4H), 3.76-3.53 (m, 2H), 3.43-3.15 (m, 5H), 2.56&2.47 (s, 3H), 2.12&2.10 (s, 3H), 1.82-1.31 (m, 4H)。
2-015: δ7.71-7.54 (m, 1H), 7.41-7.35 (m, 1H), 7.27-7.07 (m, 2H), 7.04-6.97 (m, 1H), 6.95-6.85 (m, 1H), 5.84 (s, 1H), 4.00-3.80 (m, 4H), 3.78-3.59 (m, 2H), 3.41 (s, 3H), 3.32-3.15 (m, 2H), 2.59-2.47 (m, 3H), 2.13 (s, 3H), 1.80-1.30 (m, 4H)。
2-016: δ7.71-6.90 (m, 3H), 6.02 (s, 1H), 5.55 (br, 1H), 4.00-3.80 (m, 4H), 3.69-3.56 (m, 2H), 3.50 (s, 1H), 3.39-3.25 (m, 2H), 2.80 (s, 3H), 2.61 (s, 3H), 1.79-1.45 (m, 4H)。
2-018: δ7.25-7.09 (m, 2H), 6.97-6.89 (m, 1H), 6.06-5.94 (m, 1H), 3.99-3.85 (m, 4H), 3.76-3.60 (m, 2H), 3.41-3.23 (m, 5H), 2.57-2.34 (m, 6H), 2.12 (s, 3H), 1.78-1.50 (m, 4H)。
2-019: δ7.29-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.94-6.87 (m, 2H), 5.99 (s, 1H), 4.70-4.53 (m, 2H), 3.98-3.80 (m, 4H), 3.70-3.50 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.77-1.42 (m, 4H)。
2-020: δ7.25-7.09 (m, 2H), 6.98-6.89 (m, 1H), 6.30-5.94 (m, 3H), 4.01-3.82 (m, 6H), 3.71-3.58 (m, 2H), 3.40-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.12 (s, 3H), 1.78-1.44 (m, 4H)。
2-022: δ8.85-8.54 (m, 1H), 8.32-8.25 (m, 1H), 7.24-7.08 (m, 2H), 6.96-6.89 (m, 1H), 6.12-5.97 (m, 1H), 3.99-3.84 (m, 1H), 3.90 (s, 3H), 3.80-3.58 (m, 2H), 3.47 (s, 3H), 3.43-3.21 (m, 2H), 2.57-2.45 (m, 3H), 2.12 (s, 3H), 1.83-1.42 (m, 4H)。
3-001: δ7.28-7.18 (m, 2H), 7.16-6.99 (m, 2H), 6.96-6.85 (m, 2H), 6.04-5.88 (m, 1H), 4.74-4.55 (m, 2H), 4.50 (s, 2H), 3.98-3.80 (m, 4H), 3.74-3.51 (m, 2H), 3.40-3.18 (m, 5H), 3.00 (s, 3H), 2.48 (s, 3H), 1.80-1.44 (m, 4H)。
3-002: δ7.70-7.62 (m, 1H), 7.41-7.34 (m, 1H), 7.23-7.05 (m, 2H), 7.04-6.86 (m, 2H), 6.15-5.81 (m, 1H), 4.63-4.42 (m, 2H), 4.05-3.80 (m, 4H), 3.79-3.55 (m, 2H), 3.50-3.10 (m, 8H), 2.55-2.37 (m, 3H), 1.82-1.12 (m, 4H)。
3-003:δ8.86-8.51 (m, 1H), 8.33-8.23 (m, 1H), 7.28-7.04 (m, 2H), 6.97-6.85 (m, 1H), 6.16-5.90 (m, 1H), 4.60-4.44 (m, 2H), 4.02-3.80 (m, 4H), 3.80-3.54 (m, 2H), 3.50-3.10 (m, 8H), 2.51-2.37 (m, 3H), 1.85-1.39 (m, 4H)。
3-004: δ7.28-7.18 (m, 2H), 7.17-7.07 (m, 1H), 7.03-6.88 (m, 2H), 6.13-6.06 (m, 1H), 4.58-4.47 (m, 2H), 4.55-3.83 (m, 4H), 3.80-3.62 (m, 2H), 3.45-3.27 (m, 7H), 2.51-2.43 (m, 3H), 1.82-1.21 (m, 13H)。
3-005: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.11-5.95 (m, 1H), 4.60-4.44 (m, 2H), 4.05-3.75 (m, 6H), 3.75-3.57 (m, 2H), 3.43-3.24 (m, 8H), 2.52-2.42 (m, 3H), 2.08-1.80 (m, 1H), 1.80-1.47 (m, 4H), 1.04-0.76 (m, 6H)。
3-006: δ7.28-7.21 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.13-5.88 (m, 1H), 4.59-4.46 (m, 2H), 4.02-3.76 (m, 9H), 3.76-3.57 (m, 2H), 3.42-3.26 (m, 5H), 3.01-2.92 (m, 3H), 2.53-2.45 (m, 3H), 2.10-2.02 (m, 3H), 1.83-1.47 (m, 4H)。
3-007: δ7.28-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.30-6.21 (m, 1H), 6.12-5.99 (m, 2H), 4.54-4.49 (m, 2H), 3.98-3.83 (m, 6H), 3.73-3.57 (m, 2H), 3.40-3.26 (m, 5H), 3.03-2.92 (m, 3H), 2.53-2.43 (m, 3H), 1.83-1.46 (m, 4H)。
3-008: δ7.23-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.87 (m, 1H), 4.63-4.46 (m, 2H), 4.06-3.86 (m, 4H), 3.79-3.51 (m, 5H), 3.42-3.21 (m, 8H), 2.52-2.41 (m, 3H), 2.12-1.96 (m, 3H), 1.82-1.44 (m, 4H)。
3-009: δ7.82-7.72 (m, 1H), 7.29-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.07-5.92 (m, 1H), 4.58-4.40 (m, 4H), 3.97-3.83 (m, 4H), 3.72-3.55 (m, 2H), 3.40-3.23 (m, 5H), 3.03-2.94 (m, 3H), 2.53-2.44 (m, 3H), 1.79-1.44 (m, 4H)。
3-010: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.12-5.93 (m, 1H), 4.59-4.45 (m, 2H), 4.03-3.83 (m, 6H), 3.74-3.60 (m, 2H), 3.44-3.23 (m, 8H), 2.51-2.43 (m, 3H), 1.83-1.44 (m, 4H), 1.04-0.75 (m, 9H)。
3-014: δ8.13-7.23 (m, 5H), 7.23-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.23-5.75 (m, 1H), 4.63-4.39 (m, 2H), 4.04-3.79 (m, 4H), 3.77-3.54 (m, 2H), 3.47-3.15 (m, 8H), 2.55-2.36 (m, 3H), 1.86-1.31 (m, 4H)。
3-015: δ8.15-7.81 (m, 1H), 7.24-7.17 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.86 (m, 1H), 6.12-5.91 (m, 1H), 4.57-4.41 (m, 2H), 3.99-3.81 (m, 4H), 3.79-3.54 (m, 2H), 3.50-3.20 (m, 8H), 2.50-2.40 (m, 3H), 1.83-1.40 (m, 4H)。
3-016: δ8.17-8.07 (m, 1H), 7.23-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.16-5.84 (m, 1H), 4.57-4.43 (m, 2H), 4.00-3.84 (m, 4H), 3.79-3.53 (m, 2H), 3.51-3.21 (m, 8H), 2.53-2.39 (m, 3H), 1.82-0.98 (m, 13H)。
3-017: δ7.51-7.45 (m, 1H), 7.23-7.06 (m, 2H), 6.95-6.86 (m, 1H), 6.69-6.62 (m, 1H), 6.15-5.83 (m, 1H), 4.62-4.43 (m, 2H), 4.04-3.78 (m, 4H), 3.78-3.56 (m, 2H), 3.46-3.11 (m, 8H), 2.56-2.35 (m, 6H), 1.81-1.29 (m, 4H)。
3-018: δ7.50-7.42 (m, 1H), 7.22-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.88-6.81 (m, 1H), 6.13-5.79 (m, 1H), 4.60-4.46 (m, 2H), 4.03-3.82 (m, 4H), 3.80-3.56 (m, 2H), 3.49-3.12 (m, 8H), 2.54-2.42 (m, 3H), 1.83-1.34 (m, 4H)。
3-019: δ7.27-7.05 (m, 2H), 6.96-6.87 (m, 1H), 6.14-5.89 (m, 1H), 4.57-4.46 (m, 2H), 3.98-3.86 (m, 4H), 3.77-3.60 (m, 2H), 3.48-3.17 (m, 8H), 2.72-2.08 (m, 4H), 2.06-1.01 (m, 14H)。
3-020: δ7.27-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.14-5.88 (m, 1H), 4.60-4.45 (m, 2H), 4.00-3.86 (m, 4H), 3.76-3.60 (m, 2H), 3.50-3.21 (m, 8H), 3.14-2.52 (m, 1H), 2.52-2.41 (m, 3H), 2.08-1.36 (m, 12H)。
3-021: δ7.28-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.18-5.92 (m, 1H), 4.59-4.44 (m, 2H), 4.04-3.84 (m, 4H), 3.77-3.60 (m, 2H), 3.52-3.21 (m, 8H), 2.74-2.06 (m, 4H), 1.88-1.36 (m, 8H), 1.10-0.77 (m, 6H)。
3-022: δ7.26-7.18 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 6.15-5.86 (m, 2H), 4.58-4.41 (m, 2H), 4.10-4.01 (m, 1H), 3.99-2.98 (m, 15H), 2.53-2.43 (m, 3H), 1.81-1.41 (m, 4H)。
3-023: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.12-5.95 (m, 1H), 4.86-4.62 (m, 1H), 4.60-4.45 (m, 2H), 4.07-3.22 (m, 14H), 2.54-2.42 (m, 3H), 2.00-1.10 (m, 14H)。
3-024: δ7.27-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.95-6.87 (m, 2H), 6.07-5.89 (m, 1H), 4.73-4.49 (m, 4H), 3.97-3.80 (m, 4H), 3.72-3.45 (m, 4H), 3.39-3.21 (m, 2H), 3.07-2.92 (m, 3H), 2.55-2.39 (m, 3H), 1.78-1.42 (m, 4H), 1.30-1.13 (m, 3H)。
3-025: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.10-5.94 (m, 1H), 4.65-4.49 (m, 2H), 4.05-3.46 (m, 10H), 3.42-3.25 (m, 5H), 2.51-2.42 (m, 3H), 2.07-1.81 (m, 1H), 1.80-1.47 (m, 4H), 1.30-1.17 (m, 3H), 1.02-0.75 (m, 6H)。
3-026: δ7.68-7.61 (m, 1H), 7.36-7.30 (m, 1H), 7.21-7.08 (m, 2H), 6.98-6.87 (m, 2H), 6.11-5.72 (m, 1H), 4.62-4.45 (m, 2H), 3.99-3.76 (m, 4H), 3.76-3.19 (m, 11H), 3.11-2.77 (m, 2H), 2.53-2.42 (m, 3H), 1.73-1.18 (m, 4H)。
3-027: δ7.73-7.64 (m, 1H), 7.52-6.81 (m, 5H), 5.76-5.25 (m, 1H), 4.63-4.47 (m, 2H), 4.34-4.07 (m, 1H), 3.90-3.79 (m, 4H), 3.54-3.32 (m, 6H), 2.87-2.45 (m, 6H), 1.33-1.10 (m, 3H)。
3-028: δ7.40-6.74 (m, 5H), 6.14-5.78 (m, 1H), 4.63-4.43 (m, 2H), 4.03-2.89 (m, 17H), 2.57-2.39 (m, 6H), 1.72-1.21 (m, 4H)。
3-029: δ8.87-7.90 (m, 2H), 7.25-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.11-5.88 (m, 1H), 4.61-4.44 (m, 2H), 4.01-2.98 (m, 17H), 2.55-2.39 (m, 3H), 1.75-1.16 (m, 4H)。
3-030: δ8.90-7.26 (m, 3H), 7.19-7.02 (m, 2H), 6.92-6.82 (m, 1H), 5.69-5.29 (m, 1H), 4.61-4.44 (m, 2H), 4.35-4.16 (m, 1H), 3.93-3.76 (m, 3H), 3.54-3.31 (m, 6H), 2.87-2.30 (m, 6H), 1.39-1.16 (m, 3H)。
3-031: δ8.12-7.07 (m, 7H), 6.96-6.86 (m, 1H), 6.13-5.75 (m, 1H), 4.61-4.38 (m, 2H), 4.04-2.91 (m, 17H), 2.54-2.35 (m, 3H), 1.72-1.21 (m, 4H)。
3-032: δ7.25-7.17 (m, 2H), 7.15-7.06 (m, 1H), 7.05-6.99 (m, 1H), 6.94-6.84 (m, 2H), 6.06-5.87 (m, 1H), 4.74-4.41 (m, 4H), 3.97-3.82 (m, 4H), 3.69-3.55 (m, 3H), 3.45-3.07 (m, 7H), 3.04-2.95 (m, 3H), 2.53-2.41 (m, 3H), 1.72-1.41 (m, 4H)。
3-034: δ7.25-7.17 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.28-6.19 (m, 1H), 6.11-5.95 (m, 2H), 4.65-4.43 (m, 2H), 4.00-3.81 (m, 6H), 3.65-3.55 (m, 3H), 3.50-3.10 (m, 7H), 3.00-2.92 (m, 3H), 2.53-2.43 (m, 3H), 1.73-1.44 (m, 4H)。
3-035: δ7.85-7.47 (m, 1H), 7.22-7.02 (m, 2H), 6.93-6.83 (m, 1H), 6.45-5.94 (m, 2H), 5.59-5.44 (m, 1H), 4.57-4.45 (m, 2H), 4.35-4.22 (m, 1H), 4.06-3.78 (m, 5H), 3.45-3.33 (m, 3H), 3.10-2.95 (m, 3H), 2.95-2.78 (m, 3H), 2.55-2.39 (m, 3H), 1.41-1.30 (m, 3H)。
3-036: δ7.80-7.71 (m, 1H), 7.27-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.09-5.88 (m, 1H), 4.59-4.39 (m, 4H), 3.99-3.82 (m, 4H), 3.66-3.56 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.94 (m, 3H), 2.53-2.43 (m, 3H), 1.71-1.43 (m, 4H)。
3-037: δ7.24-7.06 (m, 2H), 6.95-6.87 (m, 1H), 6.05-5.92 (m, 1H), 4.59-4.43 (m, 2H), 4.06-3.86 (m, 6H), 3.81-3.15 (m, 13H), 2.54-2.41 (m, 3H), 2.12-1.75 (m, 1H), 1.74-1.46 (m, 4H), 1.07-0.73 (m, 6H)。
3-038: δ7.79-7.47 (m, 1H), 7.25-7.01 (m, 2H), 6.92-6.82 (m, 1H), 5.67-5.46 (m, 1H), 4.62-4.45 (m, 2H), 4.35-4.21 (m, 1H), 4.06-3.69 (m, 5H), 3.48-3.25 (m, 6H), 2.90-2.73 (m, 3H), 2.55-2.37 (m, 3H), 2.14-1.74 (m, 1H), 1.40-0.73 (m, 9H)。
3-039: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.07-5.90 (m, 1H), 4.60-4.40 (m, 2H), 4.00-3.76 (m, 9H), 3.66-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.00-2.89 (m, 3H), 2.56-2.44 (m, 3H), 2.09-2.01 (m, 3H), 1.71-1.47 (m, 4H)。
3-041: δ7.25-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.07-5.84 (m, 1H), 4.62-4.40 (m, 2H), 4.04-3.83 (m, 4H), 3.73-2.92 (m, 16H), 2.52-2.43 (m, 3H), 2.12-1.95 (m, 3H), 1.78-1.39 (m, 4H)。
3-042: δ7.76-7.52 (m, 1H), 7.22-7.00 (m, 2H), 6.92-6.83 (m, 1H), 5.72-5.25 (m, 1H), 4.62-4.45 (m, 2H), 4.35-4.21 (m, 1H), 4.07-3.27 (m, 12H), 2.86-2.74 (m, 3H), 2.53-2.39 (m, 3H), 2.14-1.92 (m, 3H), 1.41-1.21 (m, 3H)。
3-043: δ7.25-7.07 (m, 2H), 7.02-6.87 (m, 2H), 6.10-5.93 (m, 1H), 4.58-4.41 (m, 2H), 4.04-3.11 (m, 17H), 2.51-2.39 (m, 3H), 1.72-1.49 (m, 4H), 1.33-1.18 (m, 9H)。
3-044: δ7.61-7.39 (m, 5H), 6.12-6.02 (m, 1H), 4.59-4.44 (m, 2H), 4.10-3.93 (m, 3H), 3.85-3.57 (m, 3H), 3.56-3.07 (m, 10H), 2.55-2.39 (m, 3H), 2.10-1.78 (m, 1H), 1.77-1.46 (m, 4H), 1.06-0.75 (m, 6H)。
3-045: δ7.58-7.35 (m, 5H), 5.49-5.23 (m, 1H), 4.64-4.43 (m, 2H), 4.20-3.65 (m, 3H), 3.45-3.16 (m, 6H), 2.98-2.70 (m, 3H), 2.54-2.37 (m, 3H), 2.11-1.75 (m, 1H), 1.66-1.37 (m, 3H), 1.31-0.71 (m, 6H)。
※NHに由来するプロトンは観測されなかった。
3-046: δ7.62-7.54 (m, 2H), 7.50-7.38 (m, 3H), 6.14-6.04 (m, 1H), 4.60-4.44 (m, 2H), 4.12-3.75 (m, 3H), 3.74-3.59 (m, 2H), 3.44-3.24 (m, 8H), 2.56-2.41 (m, 3H), 2.08-1.48 (m, 5H), 1.06-0.76 (m, 6H)。
3-047: δ7.64-7.54 (m, 2H), 7.49-7.38 (m, 3H), 6.17-6.02 (m, 1H), 4.62-4.41 (m, 2H), 4.08-3.95 (m, 1H), 3.93-3.75 (m, 5H), 3.66-3.58 (m, 3H), 3.50-3.28 (m, 5H), 3.27-3.10 (m, 2H), 3.00-2.87 (m, 3H), 2.55-2.40 (m, 3H), 2.14-1.98 (m, 3H), 1.78-1.49 (m, 4H)。
3-049: δ7.62-7.55 (m, 2H), 7.48-7.38 (m, 3H), 6.17-6.04 (m, 1H), 4.58-4.43 (m, 2H), 4.08-3.95 (m, 1H), 3.92-3.72 (m, 5H), 3.72-3.58 (m, 2H), 3.39-3.26 (m, 5H), 3.02-2.88 (m, 3H), 2.51-2.45 (m, 3H), 2.09-2.01 (m, 3H), 1.85-1.49 (m, 4H)。
3-050: δ7.61-7.54 (m, 2H), 7.49-7.41 (m, 3H), 7.23-7.18 (m, 1H), 7.05-7.01 (m, 1H), 6.92-6.86 (m, 1H), 6.13-6.01 (m, 1H), 4.73-4.55 (m, 2H), 4.55-4.43 (m, 2H), 4.04-3.93 (m, 1H), 3.70-3.56 (m, 3H), 3.51-3.32 (m, 5H), 3.25-3.04 (m, 2H), 3.03-2.96 (m, 3H), 2.54-2.42 (m, 3H), 1.75-1.42 (m, 4H)。
3-051: δ7.56-7.36 (m, 5H), 7.29-7.16 (m, 1H), 7.02-6.79 (m, 2H), 5.47-5.22 (m, 1H), 4.94-4.67 (m, 1H), 4.57-3.71 (m, 4H), 3.44-3.25 (m, 3H), 3.14-2.72 (m, 6H), 2.52-2.35 (m, 3H), 1.48-0.72 (m, 3H)。
※NHに由来するプロトンは観測されなかった。
3-052: δ7.62-7.55 (m, 2H), 7.48-7.41 (m, 3H), 7.24-7.19 (m, 1H), 7.06-7.01 (m, 1H), 6.93-6.87 (m, 1H), 6.10-6.06 (m, 1H), 4.73-4.55 (m, 2H), 4.51-4.46 (m, 2H), 4.07-3.93 (m, 1H), 3.72-3.56 (m, 2H), 3.39-3.20 (m, 5H), 3.04-2.96 (m, 3H), 2.52-2.45 (m, 3H), 1.82-1.45 (m, 4H)。
3-054: δ7.58-7.38 (m, 5H), 6.34-6.13 (m, 1H), 6.08-5.92 (m, 1H), 5.48-5.22 (m, 1H), 4.64-3.70 (m, 6H), 3.43-3.28 (m, 3H), 3.02-2.74 (m, 6H), 2.54-2.39 (m, 3H), 1.48-0.97 (m, 3H)。
3-055: δ7.68-7.38 (m, 5H), 6.33-5.98 (m, 3H), 4.60-4.43 (m, 2H), 4.19-3.83 (m, 3H), 3.76-3.61 (m, 2H), 3.48-3.26 (m, 5H), 3.08-2.92 (m, 3H), 2.58-2.42 (m, 3H), 1.87-1.49 (m, 4H)。
3-056: δ7.83-7.69 (m, 1H), 7.62-7.54 (m, 2H), 7.49-7.40 (m, 3H), 7.24-7.16 (m, 1H), 7.15-7.07 (m, 1H), 7.04-6.94 (m, 1H), 6.15-6.02 (m, 1H), 4.57-4.40 (m, 4H), 4.07-3.94 (m, 1H), 3.65-3.57 (m, 3H), 3.48-3.28 (m, 5H), 3.26-3.06 (m, 2H), 3.04-2.91 (m, 3H), 2.54-2.41 (m, 3H), 1.83-1.43 (m, 4H)。
3-057: δ7.76-7.36 (m, 6H), 7.24-7.15 (m, 1H), 7.15-6.92 (m, 2H), 5.55-5.11 (m, 1H), 4.61-4.27 (m, 4H), 4.07-3.77 (m, 1H), 3.42-3.26 (m, 3H), 3.05-2.79 (m, 6H), 2.52-2.37 (m, 3H), 1.47-0.85 (m, 3H)。
※NHに由来するプロトンは観測されなかった。
3-058: δ7.80-7.71 (m, 1H), 7.62-7.55 (m, 2H), 7.48-7.39 (m, 3H), 7.27-7.16 (m, 1H), 7.16-7.08 (m, 1H), 7.04-6.95 (m, 1H), 6.17-6.04 (m, 1H), 4.58-4.41 (m, 4H), 4.08-3.96 (m, 1H), 3.71-3.56 (m, 2H), 3.43-3.21 (m, 5H), 3.04-2.90 (m, 3H), 2.55-2.42 (m, 3H), 1.83-1.42 (m, 4H)。
3-059: δ7.69-7.31 (m, 7H), 7.00-6.93 (m, 1H), 6.16-5.88 (m, 1H), 4.61-4.45 (m, 2H), 4.03-3.87 (m, 1H), 3.75-2.65 (m, 13H), 2.55-2.40 (m, 3H), 1.82-1.30 (m, 4H)。
3-061: δ7.68-7.36 (m, 7H), 7.03-6.97 (m, 1H), 6.17-5.90 (m, 1H), 4.59-4.45 (m, 2H), 4.06-3.92 (m, 1H), 3.79-3.57 (m, 2H), 3.47-3.33 (m, 6H), 3.31-3.09 (m, 2H), 2.54-2.40 (m, 3H), 1.87-1.29 (m, 4H)。
3-062: δ7.64-6.75 (m, 7H), 6.18-5.92 (m, 1H), 4.60-4.42 (m, 2H), 4.18-3.88 (m, 1H), 3.76-2.79 (m, 13H), 2.57-2.40 (m, 6H), 1.81-1.20 (m, 4H)。
3-064: δ7.64-6.75 (m, 7H), 6.19-5.95 (m, 1H), 4.60-4.42 (m, 2H), 4.17-3.91 (m, 1H), 3.78-3.58 (m, 2H), 3.46-3.10 (m, 8H), 2.57-2.39 (m, 6H), 1.89-1.33 (m, 4H)。
3-065: δ7.73-7.19 (m, 10H), 6.18-5.88 (m, 1H), 4.62-4.39 (m, 2H), 4.18-3.81 (m, 1H), 3.78-2.80 (m, 13H), 2.57-2.41 (m, 3H), 1.81-1.17 (m, 4H)。
3-067: δ7.71-7.22 (m, 10H), 6.19-5.89 (m, 1H), 4.60-4.42 (m, 2H), 4.03-3.82 (m, 1H), 3.76-3.54 (m, 2H), 3.45-3.09 (m, 8H), 2.54-2.40 (m, 3H), 1.88-1.21 (m, 4H)。
3-068: δ7.62-7.38 (m, 5H), 7.05-6.94 (m, 1H), 6.15-6.04 (m, 1H), 4.59-4.45 (m, 2H), 4.18-4.03 (m, 1H), 3.86-3.11 (m, 13H), 2.52-2.41 (m, 3H), 1.81-1.46 (m, 4H), 1.33-1.19 (m, 9H)。
3-069: δ7.57-7.33 (m, 5H), 7.10-6.95 (m, 1H), 5.53-5.12 (m, 1H), 4.66-4.42 (m, 2H), 4.18-3.87 (m, 1H), 3.81-3.22 (m, 6H), 2.99-2.74 (m, 3H), 2.47-2.38 (m, 3H), 1.53-1.37 (m, 3H), 1.36-1.16 (m, 9H)。
※NHに由来するプロトンは観測されなかった。
3-070: δ7.62-7.39 (m, 5H), 6.13-5.96 (m, 1H), 4.59-4.45 (m, 2H), 4.10-2.93 (m, 17H), 2.54-2.40 (m, 3H), 2.13-1.97 (m, 3H), 1.82-1.40 (m, 4H)。
3-072: δ7.62-7.52 (m, 2H), 7.51-7.40 (m, 3H), 6.15-5.97 (m, 1H), 4.61-4.45 (m, 2H), 4.10-3.21 (m, 14H), 2.54-2.40 (m, 3H), 2.13-1.97 (m, 3H), 1.86-1.47 (m, 4H)。
3-073: δ8.95-7.35 (m, 7H), 6.17-6.02 (m, 1H), 4.61-4.44 (m, 2H), 4.16-2.89 (m, 14H), 2.54-2.39 (m, 3H), 1.84-1.17 (m, 4H)。
3-075: δ8.87-7.37 (m, 7H), 6.18-6.06 (m, 1H), 4.59-4.44 (m, 2H), 4.17-3.97 (m, 1H), 3.87-3.15 (m, 10H), 2.52-2.40 (m, 3H), 1.87-1.42 (m, 4H)。
3-076: δ7.51-6.86 (m, 7H), 5.94-5.80 (m, 1H), 4.73-4.57 (m, 2H), 4.54-4.44 (m, 2H), 3.97-3.87 (m, 4H), 3.70-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.05-2.97 (m, 3H), 2.53-2.43 (m, 3H), 1.76-1.44 (m, 4H)。
3-077: δ7.51-7.37 (m, 2H), 7.22-7.16 (m, 1H), 7.06-6.85 (m, 4H), 5.92-5.81 (m, 1H), 4.73-4.45 (m, 4H), 3.95-3.83 (m, 4H), 3.65-3.57 (m, 3H), 3.46-3.07 (m, 7H), 3.05-2.95 (m, 3H), 2.53-2.42 (m, 3H), 1.71-1.18 (m, 4H)。
3-078: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 6.30-6.21 (m, 1H), 6.12-6.00 (m, 1H), 5.94-5.80 (m, 1H), 4.57-4.47 (m, 2H), 4.01-3.25 (m, 13H), 3.03-2.94 (m, 3H), 2.54-2.44 (m, 3H), 1.78-1.47 (m, 4H)。
3-079: δ7.50-7.38 (m, 2H), 7.07-6.93 (m, 2H), 6.28-6.19 (m, 1H), 6.11-5.99 (m, 1H), 5.86-5.78 (m, 1H), 4.56-4.48 (m, 2H), 4.00-3.83 (m, 6H), 3.65-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.01-2.93 (m, 3H), 2.53-2.43 (m, 3H), 1.70-1.18 (m, 4H)。
3-080: δ7.84-6.93 (m, 8H), 5.95-5.86 (m, 1H), 4.59-4.40 (m, 4H), 4.00-3.85 (m, 4H), 3.70-3.53 (m, 2H), 3.41-3.22 (m, 5H), 3.04-2.94 (m, 3H), 2.53-2.45 (m, 3H), 1.78-1.44 (m, 4H)。
3-081: δ7.82-6.92 (m, 8H), 5.95-5.83 (m, 1H), 4.57-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.64-3.56 (m, 2H), 3.45-3.10 (m, 8H), 3.01-2.92 (m, 3H), 2.52-2.44 (m, 3H), 1.70-1.21 (m, 4H)。
3-082: δ7.52-7.39 (m, 2H), 7.33-7.28 (m, 1H), 7.26-7.20 (m, 2H), 7.06-6.94 (m, 2H), 5.95-5.85 (m, 1H), 4.55-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.72-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.04-2.95 (m, 3H), 2.52-2.45 (m, 3H), 1.78-1.47 (m, 4H)。
3-083: δ7.51-7.38 (m, 2H), 7.31-7.26 (m, 1H), 7.25-7.18 (m, 2H), 7.05-6.93 (m, 2H), 5.90-5.81 (m, 1H), 4.54-4.38 (m, 4H), 3.96-3.84 (m, 4H), 3.66-3.57 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.92 (m, 3H), 2.52-2.42 (m, 3H), 1.70-1.17 (m, 4H)。
3-084: δ8.86-7.38 (m, 4H), 7.05-6.92 (m, 2H), 5.99-5.82 (m, 1H), 4.58-4.45 (m, 2H), 4.02-3.18 (m, 17H), 2.51-2.37 (m, 3H), 1.80-1.37 (m, 4H)。
3-085: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.95-5.87 (m, 1H), 4.56-4.48 (m, 2H), 3.98-3.77 (m, 9H), 3.71-3.55 (m, 2H), 3.39-3.24 (m, 5H), 2.99-2.91 (m, 3H), 2.53-2.44 (m, 3H), 2.09-2.02 (m, 3H), 1.78-1.48 (m, 4H)。
3-086: δ7.51-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.87-5.84 (m, 1H), 4.55-4.48 (m, 2H), 3.97-3.75 (m, 9H), 3.74-3.59 (m, 5H), 3.43-3.13 (m, 5H), 2.97-2.91 (m, 3H), 2.51-2.44 (m, 3H), 2.07-2.02 (m, 3H), 1.66-1.50 (m, 4H)。
3-087: δ7.49-7.37 (m, 2H), 7.08-6.93 (m, 2H), 5.95-5.82 (m, 1H), 4.60-4.45 (m, 2H), 4.05-3.22 (m, 16H), 2.53-2.43 (m, 3H), 2.06-1.80 (m, 1H), 1.78-1.47 (m, 4H), 1.03-0.75 (m, 6H)。
3-088: δ7.49-7.37 (m, 2H), 7.06-6.93 (m, 2H), 5.90-5.80 (m, 1H), 4.61-4.46 (m, 2H), 4.06-3.14 (m, 19H), 2.53-2.42 (m, 3H), 2.08-1.73 (m, 1H), 1.68-1.16 (m, 4H), 1.03-0.73 (m, 6H)。
3-089: δ7.71-7.65 (m, 1H), 7.50-7.36 (m, 3H), 7.06-6.93 (m, 3H), 6.02-5.70 (m, 1H), 4.60-4.46 (m, 2H), 4.03-3.13 (m, 14H), 2.53-2.42 (m, 3H), 1.78-1.30 (m, 4H)。
3-090: δ7.93-6.91 (m, 7H), 5.99-5.52 (m, 1H), 4.62-4.47 (m, 2H), 4.01-2.79 (m, 17H), 2.53-2.41 (m, 3H), 1.69-1.14 (m, 4H)。
3-091: δ7.54-6.79 (m, 6H), 6.04-5.71 (m, 1H), 4.60-4.44 (m, 2H), 4.03-3.81 (m, 4H), 3.75-3.57 (m, 2H), 3.45-3.15 (m, 8H), 2.59-2.39 (m, 6H), 1.79-1.16 (m, 4H)。
3-092: δ7.55-6.76 (m, 6H), 6.02-5.68 (m, 1H), 4.63-4.45 (m, 2H), 4.04-2.91 (m, 17H), 2.61-2.39 (m, 6H), 1.69-1.13 (m, 4H)。
3-093: δ7.62-7.06 (m, 6H), 6.59-6.40 (m, 1H), 6.23-6.00 (m, 1H), 4.60-4.46 (m, 2H), 4.04-3.91 (m, 1H), 3.81-3.14 (m, 10H), 2.53-2.41 (m, 3H), 1.87-1.47 (m, 4H)。
3-094: δ8.73-7.20 (m, 8H), 6.26-6.03 (m, 1H), 4.61-4.43 (m, 2H), 4.11-3.91 (m, 1H), 3.79-3.17 (m, 10H), 2.53-2.37 (m, 3H), 1.88-1.20 (m, 4H)。
3-095: δ7.65-7.20 (m, 4H), 6.21-6.06 (m, 1H), 4.63-4.45 (m, 2H), 4.10-3.99 (m, 1H), 3.78-3.65 (m, 2H), 3.48-3.22 (m, 8H), 2.55-2.45 (m, 3H), 2.45-1.95 (m, 2H), 1.88-1.47 (m, 4H), 1.08-0.83 (m, 7H)。
3-096: δ8.77-7.20 (m, 7H), 6.21-5.87 (m, 1H), 4.61-4.43 (m, 2H), 4.04-3.90 (m, 1H), 3.78-3.63 (m, 2H), 3.44-3.15 (m, 8H), 2.52-2.40 (m, 3H), 1.82-1.34 (m, 4H)。
3-097: δ8.00-7.34 (m, 6H), 6.21-6.06 (m, 1H), 4.60-4.46 (m, 2H), 4.09-3.94 (m, 1H), 3.82-3.58 (m, 2H), 3.53-3.16 (m, 8H), 2.51-2.39 (m, 3H), 1.88-1.39 (m, 4H)。
3-099: δ7.61-7.27 (m, 5H), 6.66-6.26 (m, 1H), 6.19-5.95 (m, 1H), 4.56-4.46 (m, 2H), 4.10-3.90 (m, 4H), 3.79-3.65 (m, 2H), 3.51-3.16 (m, 8H), 2.52-2.39 (m, 3H), 1.88-1.13 (m, 4H)。
3-100: δ7.91-7.32 (m, 6H), 6.22-5.95 (m, 1H), 4.57-4.47 (m, 2H), 4.03-3.13 (m, 14H), 2.82-2.42 (m, 3H), 1.87-1.17 (m, 4H)。
3-102: δ7.88-6.88 (m, 6H), 6.25-5.99 (m, 1H), 4.60-4.44 (m, 2H), 4.11-3.89 (m, 1H), 3.79-3.62 (m, 2H), 3.49-3.16 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.31 (m, 4H)。
3-103: δ8.70-7.36 (m, 7H), 6.25-5.99 (m, 1H), 4.60-4.45 (m, 2H), 4.10-3.93 (m, 1H), 3.80-3.18 (m, 10H), 2.52-2.36 (m, 3H), 1.88-1.33 (m, 4H)。
3-104: δ8.08-8.02 (m, 1H), 7.75-7.67 (m, 1H), 7.61-7.23 (m, 5H), 6.23-6.05 (m, 1H), 4.58-4.49 (m, 2H), 4.08-3.92 (m, 1H), 3.78-3.18 (m, 10H), 2.52-2.38 (m, 3H), 1.86-1.33 (m, 4H)。
3-105: δ7.29-6.81 (m, 6H), 6.01-5.89 (m, 1H), 4.73-4.39 (m, 4H), 4.02-3.68 (m, 7H), 3.40-3.29 (m, 3H), 3.05-2.92 (m, 3H), 2.53-2.42 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H)。
3-106: δ7.31-7.05 (m, 5H), 6.97-6.87 (m, 1H), 6.01-5.89 (m, 1H), 4.55-4.37 (m, 4H), 4.02-3.68 (m, 7H), 3.39-3.29 (m, 3H), 3.01-2.89 (m, 3H), 2.52-2.43 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H)。
3-107: δ7.59-7.50 (m, 2H), 7.35-7.17 (m, 4H), 7.17-7.06 (m, 1H), 6.97-6.87 (m, 1H), 6.04-5.91 (m, 1H), 4.55-4.34 (m, 4H), 4.02-3.68 (m, 7H), 3.39-3.29 (m, 3H), 2.96-2.86 (m, 3H), 2.52-2.45 (m, 3H), 2.45-1.88 (m, 4H), 1.83-1.51 (m, 4H)。
3-108: δ7.82-7.72 (m, 1H), 7.30-6.88 (m, 6H), 6.04-5.93 (m, 1H), 4.57-4.39 (m, 4H), 4.02-3.60 (m, 7H), 3.40-3.30 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.89 (m, 4H), 1.84-1.53 (m, 4H)。
3-109: δ7.27-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.89 (m, 1H), 6.29-6.20 (m, 1H), 6.11-5.89 (m, 2H), 4.56-4.43 (m, 2H), 4.04-3.73 (m, 9H), 3.40-3.31 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.43 (m, 3H), 2.43-1.92 (m, 4H), 1.85-1.54 (m, 4H)。
3-110: δ7.28-7.18 (m, 1H), 7.18-7.07 (m, 1H), 6.96-6.86 (m, 1H), 6.05-5.89 (m, 1H), 4.59-4.44 (m, 2H), 4.07-3.95 (m, 1H), 3.94-3.69 (m, 6H), 3.58-3.13 (m, 6H), 2.50-2.40 (m, 3H), 2.41-1.91 (m, 4H), 1.89-1.14 (m, 13H)。
3-111: δ7.62-7.20 (m, 7H), 7.01-6.90 (m, 1H), 6.19-6.08 (m, 1H), 4.63-4.36 (m, 4H), 4.02-3.92 (m, 1H), 3.66-3.56 (m, 3H), 3.47-3.03 (m, 7H), 2.98-2.87 (m, 3H), 2.54-2.43 (m, 3H), 1.74-1.37 (m, 4H)。
3-112: δ7.61-6.95 (m, 8H), 6.17-6.07 (m, 1H), 4.61-4.33 (m, 4H), 4.02-3.91 (m, 1H), 3.67-3.56 (m, 3H), 3.46-3.05 (m, 7H), 2.96-2.87 (m, 3H), 2.53-2.44 (m, 3H), 1.73-1.41 (m, 4H)。
3-113: δ7.61-7.08 (m, 8H), 6.20-6.09 (m, 1H), 4.56-4.34 (m, 4H), 4.01-3.89 (m, 1H), 3.69-3.56 (m, 3H), 3.47-3.30 (m, 5H), 3.25-3.09 (m, 2H), 2.99-2.87 (m, 3H), 2.54-2.42 (m, 6H), 1.75-1.42 (m, 4H)。
3-114: δ7.75-7.35 (m, 5H), 7.25-7.17 (m, 1H), 6.98-6.91 (m, 1H), 6.85-6.80 (m, 1H), 6.21-6.09 (m, 1H), 4.57-4.34 (m, 4H), 4.02-3.92 (m, 1H), 3.85-3.73 (m, 3H), 3.67-3.56 (m, 3H), 3.46-3.29 (m, 5H), 3.26-3.07 (m, 2H), 3.03-2.93 (m, 3H), 2.55-2.43 (m, 3H), 1.73-1.42 (m, 4H)。
3-115: δ7.60-7.17 (m, 5H), 6.89-6.82 (m, 2H), 6.21-6.10 (m, 1H), 4.57-4.39 (m, 4H), 4.03-3.93 (m, 1H), 3.68-3.57 (m, 3H), 3.53-3.31 (m, 5H), 3.26-3.10 (m, 2H), 3.10-3.00 (m, 3H), 2.51-2.36 (m, 3H), 1.77-1.45 (m, 4H)。
3-116: δ7.61-7.35 (m, 4H), 7.13-7.09 (m, 1H), 6.79-6.74 (m, 1H), 6.19-6.10 (m, 1H), 4.68-4.43 (m, 4H), 4.01-3.91 (m, 1H), 3.68-3.58 (m, 3H), 3.48-3.30 (m, 5H), 3.26-3.06 (m, 2H), 3.02-2.93 (m, 3H), 2.52-2.43 (m, 3H), 2.31-2.21 (m, 3H), 1.74-1.42 (m, 4H)。
3-117: δ8.90-7.03 (m, 6H), 6.20-6.10 (m, 1H), 4.89-4.47 (m, 4H), 4.05-3.92 (m, 1H), 3.66-3.58 (m, 3H), 3.47-3.29 (m, 5H), 3.25-3.01 (m, 5H), 2.52-2.45 (m, 3H), 1.76-1.42 (m, 4H)。
3-118: δ7.61-7.35 (m, 5H), 6.13-6.04 (m, 1H), 4.64-4.46 (m, 4H), 4.04-3.93 (m, 1H), 3.68-3.58 (m, 3H), 3.47-3.30 (m, 5H), 3.26-3.07 (m, 2H), 3.03-2.91 (m, 3H), 2.53-2.41 (m, 3H), 1.74-1.44 (m, 4H)。
3-119: δ8.46-7.21 (m, 7H), 6.15-6.03 (m, 1H), 4.77-4.36 (m, 4H), 4.04-3.93 (m, 1H), 3.67-3.56 (m, 3H), 3.45-3.06 (m, 7H), 2.98-2.89 (m, 3H), 2.52-2.41 (m, 3H), 1.74-1.44 (m, 4H)。
3-120: δ7.61-7.36 (m, 4H), 6.20-6.08 (m, 1H), 4.59-4.46 (m, 2H), 4.05-3.93 (m, 1H), 3.69-3.56 (m, 3H), 3.52-3.32 (m, 5H), 3.24-3.08 (m, 4H), 3.07-2.97 (m, 3H), 2.54-2.43 (m, 3H), 1.79-1.48 (m, 4H), 1.04-0.89 (m, 1H), 0.46-0.32 (m, 2H), 0.15-0.06 (m, 2H)。
3-121: δ7.61-7.36 (m, 4H), 6.20-5.94 (m, 3H), 4.57-4.46 (m, 2H), 4.18-4.08 (m, 2H), 4.04-3.94 (m, 1H), 3.67-3.61 (m, 3H), 3.49-3.32 (m, 5H), 3.27-3.10 (m, 2H), 3.07-3.00 (m, 3H), 2.51-2.42 (m, 3H), 1.76-1.45 (m, 4H)。
3-122: δ8.97-7.33 (m, 7H), 7.29-7.20 (m, 1H), 6.22-5.91 (m, 1H), 4.56-4.43 (m, 2H), 4.09-3.86 (m, 1H), 3.78-3.58 (m, 2H), 3.46-3.14 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.29 (m, 4H)。
3-125: δ7.90-7.83 (m, 2H), 7.37-7.20 (m, 4H), 7.15-7.05 (m, 1H), 6.94-6.87 (m, 1H), 5.98-5.85 (m, 1H), 4.64-4.34 (m, 4H), 4.00-3.71 (m, 10H), 3.40-3.28 (m, 3H), 3.08-2.98 (m, 3H), 2.49-2.41 (m, 3H), 2.39-1.86 (m, 4H), 1.82-1.53 (m, 4H)。
3-126: δ7.28-7.21 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.03-5.91 (m, 1H), 4.55-4.42 (m, 2H), 4.02-3.70 (m, 12H), 3.39-3.30 (m, 3H), 2.96-2.89 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.91 (m, 7H), 1.84-1.51 (m, 4H)。
3-128: δ7.86-7.06 (m, 5H), 6.96-6.87 (m, 1H), 6.09-5.78 (m, 1H), 4.57-4.41 (m, 2H), 4.07-3.72 (m, 7H), 3.50-3.32 (m, 6H), 2.57-1.88 (m, 7H), 1.87-1.31 (m, 4H)。
3-129: δ8.86-8.25 (m, 2H), 7.24-7.18 (m, 1H), 7.16-7.08 (m, 1H), 6.96-6.87 (m, 1H), 6.08-5.91 (m, 1H), 4.59-4.43 (m, 2H), 4.06-3.73 (m, 7H), 3.50-3.32 (m, 6H), 2.50-1.88 (m, 7H), 1.78-1.50 (m, 4H)。
3-130: δ7.27-7.05 (m, 2H), 6.97-6.86 (m, 1H), 6.10-5.90 (m, 1H), 4.58-4.43 (m, 2H), 4.06-3.94 (m, 1H), 3.94-3.86 (m, 3H), 3.79-3.72 (m, 3H), 3.50-3.20 (m, 6H), 2.71-2.55 (m, 1H), 2.51-1.91 (m, 7H), 1.86-1.33 (m, 8H), 1.11-0.77 (m, 6H)。
3-131: δ7.72-7.64 (m, 1H), 7.56-7.40 (m, 2H), 7.35-7.07 (m, 4H), 6.96-6.86 (m, 1H), 6.11-5.76 (m, 1H), 4.58-4.38 (m, 2H), 4.18-3.70 (m, 7H), 3.42-3.28 (m, 6H), 2.54-1.39 (m, 11H)。
3-132: δ7.27-7.18 (m, 1H), 7.18-7.04 (m, 1H), 6.97-6.86 (m, 1H), 6.05-5.90 (m, 1H), 4.59-4.41 (m, 2H), 4.06-3.61 (m, 9H), 3.45-3.25 (m, 6H), 2.70-1.52 (m, 12H), 1.06-0.69 (m, 6H)。
3-133: δ7.27-7.19 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.02-5.97 (m, 1H), 4.55-4.47 (m, 2H), 4.03-3.86 (m, 4H), 3.78-3.70 (m, 3H), 3.39-3.31 (m, 3H), 3.28-3.17 (m, 2H), 3.02-2.92 (m, 3H), 2.52-2.45 (m, 3H), 2.45-2.10 (m, 4H), 2.07-0.78 (m, 13H)。
3-134: δ7.29-7.22 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.04-5.98 (m, 1H), 4.55-4.47 (m, 2H), 4.04-3.72 (m, 9H), 3.58-3.52 (m, 3H), 3.39-3.31 (m, 3H), 3.03-2.95 (m, 3H), 2.51-2.44 (m, 3H), 2.42-1.89 (m, 4H), 1.87-1.57 (m, 4H), 1.34-1.07 (m, 9H)。
3-135: δ7.25-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.85 (m, 1H), 4.60-4.44 (m, 2H), 4.05-2.97 (m, 16H), 2.53-1.92 (m, 10H), 1.81-1.55 (m, 4H)。
3-136: δ8.15-6.90 (m, 9H), 6.00-5.65 (m, 1H), 4.57-4.38 (m, 2H), 4.05-3.13 (m, 14H), 2.55-2.35 (m, 3H), 1.82-1.30 (m, 4H)。
3-137: δ8.14-6.90 (m, 9H), 5.97-5.62 (m, 1H), 4.58-4.43 (m, 2H), 4.03-2.87 (m, 17H), 2.54-2.37 (m, 3H), 1.70-1.20 (m, 4H)。
3-138: δ7.26-7.18 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.08-5.90 (m, 1H), 4.59-4.42 (m, 2H), 4.05-3.19 (m, 17H), 2.53-2.42 (m, 3H), 2.41-1.92 (m, 4H), 1.87-1.53 (m, 8H)。
3-139: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 5.99-5.93 (m, 1H), 4.56-4.47 (m, 2H), 4.04-3.94 (m, 1H), 3.93-3.85 (m, 3H), 3.78-3.71 (m, 3H), 3.41-3.33 (m,3H), 3.33-3.21 (m, 4H), 3.21-3.13 (m, 3H), 2.51-1.91 (m, 7H), 1.79-1.41 (m, 10H)。
3-140: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 5.94-5.88 (m, 1H), 4.55-4.47 (m, 2H), 4.28-4.14 (m, 1H), 4.04-3.92 (m, 1H), 3.92-3.85 (m, 3H), 3.78-3.70 (m, 3H), 3.41-3.33 (m,3H), 3.17-3.08 (m, 3H), 2.65-2.56 (m, 3H), 2.51-1.91 (m, 7H), 1.78-1.57 (m, 4H), 1.41-0.99 (m, 6H)。
4-001: δ7.40-6.80 (m, 3H), 6.09 (s, 1H), 6.02 (s, 1H), 4.30-3.20 (m, 17H), 2.95 (s, 3H), 2.55 (s, 3H), 2.10-2.00 (m, 3H), 1.80-1.50 (m, 4H)。
4-002: δ7.70-6.85 (m, 6H), 6.09 (s, 1H), 5.81 (s, 1H), 4.25-3.10 (m, 12H), 2.54 (s, 3H), 2.03 (s, 3H), 1.85-1.15 (m, 4H)。
4-003: δ7.25-7.19 (m, 2H), 7.16-7.07 (m, 1H), 7.07-7.01 (m, 1H), 6.95-6.87 (m, 2H), 6.05-5.87 (m, 1H), 4.73-4.51 (m, 2H), 3.98-3.82 (m, 4H), 3.71-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.06-2.93 (m, 3H), 2.65-2.51 (m, 3H), 2.37-2.23 (m, 3H), 1.79-1.44 (m, 4H)。
4-004: δ7.25-7.18 (m, 2H), 7.18-7.08 (m, 1H), 7.07-7.00 (m, 1H), 6.95-6.87 (m, 2H), 5.95-5.89 (m, 1H), 4.72-4.50 (m, 2H), 3.98-3.82 (m, 4H), 3.74-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.05-2.96 (m, 3H), 2.91-2.83 (m, 3H), 2.66-2.56 (m, 3H), 1.78-1.43 (m, 4H)。
4-006: δ7.80-6.80 (m, 6H), 6.00-5.20 (m, 2H), 3.90-3.20 (m, 15H), 2.50-2.40 (m, 3H), 1.80-1.50 (m, 4H)。
4-007: δ7.35-6.80 (m, 6H), 6.00-5.90 (m, 2H), 4.72-4.50 (m, 2H), 4.00-3.20 (m, 12H), 3.10-2.90 (m, 3H), 2.55-2.40 (m, 3H), 1.85-1.50 (m, 4H)。
4-011: δ7.78-7.68 (m, 1H), 7.64-7.55 (m, 1H), 7.50-6.90 (m, 6H), 6.17-6.09 (m, 1H), 4.54-4.41 (m, 2H), 4.34-4.24 (m, 2H), 4.05-3.93 (m, 1H), 3.75-3.61 (m, 2H), 3.51-3.40 (m, 2H), 3.39-3.25 (m, 2H), 3.03-2.95 (m, 3H), 2.92-2.83 (m, 3H), 1.84-1.70 (m, 2H), 1.63-1.46 (m, 2H)。
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[試験例]
次に、本発明化合物の一態様に係る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が、本発明はこれらのみに限定されるものではない。なお、試験例中「RH」とは相対湿度(relative humidity)を表し、例えば、「湿度100%RH」の記載は、相対湿度が100%であることを表す。 [Table 7]
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No. 1 H-NMR
――――――――――――――――――――――――――――――――――
1-001: δ7.26-7.19 (m, 1H), 7.16-7.00 (m, 1H), 6.99-6.85 (m, 1H), 6.10&5.94 (s, 1H), 4.52-4.35 (m, 2H) ), 4.07-3.86 (m, 6H), 3.76-3.61 (m, 2H), 3.40-3.23 (m, 5H), 2.84&2.82 (s, 3H), 1.81-1.48 (m, 13H).
1-013: δ7.48-7.35 (m, 2H), 7.35-7.10 (m, 3H), 7.08-6.99 (m, 1H), 6.98-6.85 (m, 1H), 6.12 (s, 1H), 4.74 -4.55 (m, 2H), 4.50-4.38 (m, 2H), 4.07-3.93 (m, 3H), 3.73-3.59 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H) , 2.83 (s, 3H), 1.81-1.46 (m, 4H).
1-014: δ7.51-7.39 (m, 2H), 7.25-7.16 (m, 1H), 7.08-6.84 (m, 4H), 5.84 (s, 1H), 4.74-4.57 (m, 2H), 4.49 -4.35 (m, 2H), 4.08-3.87 (m, 6H), 3.73-3.56 (m, 2H), 3.39-3.22 (m, 2H), 3.01 (s, 3H), 2.82 (s, 3H), 1.80 -1.46 (m, 4H).
1-016: δ7.47-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.11 (m, 1H), 6.14 (s, 1H), 4.49-4.36 (m, 2H), 4.06 -3.96 (m, 3H), 3.90-3.76 (m, 5H), 3.74-3.61 (m, 2H), 3.40-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.85-1.50 (m, 4H).
1-017: δ7.29-7.37 (m, 2H), 7.19-7.13 (m, 2H), 7.05-6.90 (m, 3H), 5.85 (s, 1H), 4.65-4.49 (m, 2H), 4.45 -4.35 (m, 2H), 4.06-3.97 (m, 2H), 3.96-3.86 (m, 4H), 3.75-3.55 (m, 2H), 3.40-3.20 (m, 2H), 3.10 (s, 3H) , 2.78 (s, 3H), 1.80-1.45 (m, 4H).
1-018: δ7.45-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.10 (m, 3H), 7.00-6.92 (m, 1H), 6.13 (s, 1H), 4.64 -4.48 (m, 2H), 4.47-4.35 (m, 2H), 4.05-3.95 (m, 3H), 3.76-3.60 (m, 2H), 3.38-3.25 (m, 2H), 3.08 (s, 3H) , 2.79 (s, 3H), 1.85-1.50 (m, 4H).
1-025: δ8.56-8.52 (m, 1H), 8.34-8.29 (m, 1H), 7.50-7.38 (m, 2H), 7.05-6.94 (m, 2H), 5.85 (s, 1H), 4.49 -4.35 (m, 2H), 4.08-3.88 (m, 6H), 3.80-3.55 (m, 2H), 3.48 (s, 3H), 3.40-3.20 (m, 2H), 2.77 (s, 3H), 1.80 -1.45 (m, 4H).
1-026: δ8.60-8.55 (m, 1H), 8.35-8.30 (m, 1H), 7.47-7.34 (m, 2H), 7.32-7.24 (m, 1H), 7.21-7.12 (m, 1H) , 6.12 (s, 1H), 4.50-4.39 (m, 2H), 4.10-3.95 (m, 3H), 3.82-3.60 (m, 2H), 3.47 (s, 3H), 3.40-3.20 (m, 2H) , 2.77 (s, 3H), 1.86-1.43 (m, 4H).
1-027: δ7.50-7.40 (m, 2H), 7.10-6.95 (m, 2H), 6.91&5.84 (s, 1H), 4.50-4.35 (m, 2H), 4.08-3.75 (m, 8H) ), 3.73-3.59 (m, 2H), 3.40-3.27 (s, 5H), 2.82 (s, 3H), 2.05-1.45 (m, 5H), 1.02-0.78 (m, 6H).
1-028: δ7.47-7.35 (m, 2H), 7.32-7.25 (m, 1H), 7.23-7.13 (m, 1H), 6.17&6.11 (s, 1H), 4.50-4.37 (m, 2H) ), 4.10-3.75 (m, 5H), 3.75-3.61 (m, 2H), 3.40-3.20 (m, 5H), 2.82 (s, 3H), 2.05-1.50 (m, 5H), 1.01-0.78 (m , 6H).
1-031: δ7.25-7.19 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 5.98 (s, 1H), 4.48-4.35 (m, 2H), 4.06 -3.96 (m, 2H), 3.96-3.61 (m, 12H), 3.48-3.30 (m, 2H), 3.28-3.11 (m, 2H), 2.95 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.70-1.48 (m, 4H).
1-038: δ7.24-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.00&5.92 (s, 1H), 4.50-4.36 (m, 2H), 4.08-3.88 (m, 8H) ), 3.63 (s, 3H), 3.50-3.12 (m, 7H), 2.81 (s, 3H), 2.05-1.48 (m, 5H), 1.01-0.77 (m, 6H).
1-042: δ7.61-7.55 (m, 2H), 7.48-7.41 (m, 3H), 6.08 (s, 1H), 4.47-4.38 (m, 2H), 4.10-3.96 (m, 3H), 3.91 -3.77 (m, 2H), 3.80 (s, 3H), 3.71-3.60 (m, 2H), 3.39-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.05 (s , 3H), 1.82-1.50 (m, 4H).
1-046: δ7.62-7.55 (m, 2H), 7.50-7.40 (m, 3H), 6.06 (s, 1H), 4.49-4.34 (m, 2H), 4.08-3.97 (m, 3H), 3.91 -3.76 (m, 2H), 3.79 (s, 3H), 3.63 (s, 3H), 3.49-3.33 (m, 2H), 3.25-3.09 (m, 2H), 2.95 (s, 3H), 2.83 (s , 3H), 2.05 (s, 3H), 1.77-1.47 (m, 4H).
1-047: δ7.60-7.54 (m, 2H), 7.49-7.41 (m, 3H), 6.28-6.21 (m, 1H), 6.10-5.99 (m, 1H), 6.03 (s, 1H), 4.48 -4.39 (m, 2H), 4.09-3.82 (m, 4H), 3.73-3.65 (m, 1H), 3.62 (s, 3H), 3.52-3.38 (m, 2H), 3.20-3.05 (m, 2H) , 2.97 (s, 3H), 2.82 (s, 3H), 1.77-1.45 (m, 4H).
1-059: δ8.60-8.50 (m, 1H), 8.35-8.30 (m, 1H), 7.60-7.52 (m, 1H), 7.50-7.34 (m, 3H), 6.11 (s, 1H), 4.50 -4.37 (m, 2H), 4.10-3.89 (m, 3H), 3.80-3.60 (m, 2H), 3.46 (s, 3H), 3.40-3.15 (m, 2H), 2.77 (s, 3H), 1.90 -1.40 (m, 4H).
1-063: δ7.25-7.20 (m, 1H), 7.18-7.09 (m, 1H), 6.96-6.89 (m, 1H), 6.08&5.98 (s, 1H), 4.50-4.38 (m, 2H) ), 4.20-3.88 (m, 8H), 3.73-3.60 (m, 2H), 3.38-3.29 (m, 5H), 2.83&2.82 (s, 3H), 1.80-1.50 (m, 6H), 1.03- 0.80 (m, 3H).
1-064: δ7.60-7.58 (m, 1H), 7.50-7.36 (m, 3H), 7.24-7.20 (m, 1H), 7.06-7.03 (m, 1H), 6.95-6.90 (m, 1H) , 6.11 (s, 1H), 4.72-4.57 (m, 2H), 4.47-4.39 (m, 2H), 4.08-3.92 (m, 3H), 3.71-3.59 (m, 2H), 3.38-3.24 (m, 2H), 3.01 (s, 3H), 2.83 (s, 3H), 1.80-1.45 (m, 4H).
1-065: δ7.62-7.57 (m, 1H), 7.52-7.37 (m, 3H), 6.30-6.24 (m, 1H), 6.15-5.94 (m, 2H), 4.49-4.40 (m, 2H) , 4.06-3.84 (m, 5H), 3.72-3.62 (m, 2H), 3.38-3.29 (m, 2H), 2.98 (s, 3H), 2.83 (s, 3H), 1.80-1.50 (m, 4H) .
1-066: δ7.76-7.68 (m, 1H), 7.62-7.58 (m, 1H), 7.52-7.30 (m, 3H), 7.25-7.19 (m, 1H), 7.16-6.95 (m, 2H) , 6.13 (s, 1H), 4.54-4.38 (m, 4H), 4.06-3.90 (m, 3H), 3.70-3.60 (m, 2H), 3.39-3.25 (m, 2H), 2.99 (s, 3H) , 2.88&2.83 (s, 3H), 1.80-1.50 (m, 4H).
1-067: δ7.24-7.03 (m, 2H), 6.95-6.70 (m, 1H), 6.05 & 5.90 (s, 1H), 4.49-4.36 (m, 2H), 4.10-3.95 (m, 2H) , 3.90 & 3.89 (s, 3H), 3.85-3.72 (m, 1H), 3.30 & 3.25 (s, 3H), 2.84 & 2.82 (s, 3H), 2.75-2.51 (m, 2H), 2.40-2.20 ( m, 2H), 2.06-1.66 (m, 4H), 1.53 & 1.41 (s, 9H).
1-068: δ7.29-7.20 (m, 1H), 7.16-7.06 (m, 1H), 6.94-6.84 (m, 1H), 6.17-5.81 (m, 1H), 4.73-4.61 (m, 1H) , 4.47-4.34 (m, 2H), 4.08-3.97 (m, 2H), 3.92-3.84 (m, 3H), 3.38-3.22 (m, 6H), 3.05-2.97 (m, 3H), 2.86-2.77 ( m, 3H), 1.56-1.17 (m, 12H).
1-069: δ7.59-7.38 (m, 1H), 7.17-7.05 (m, 1H), 6.94-6.85 (m, 1H), 6.29-5.88 (m, 1H), 4.47-4.32 (m, 3H) , 4.07-3.96 (m, 2H), 3.93-3.87 (m, 3H), 3.40-3.04 (m, 5H), 2.86-2.71 (m, 6H), 2.20-2.00 (m, 2H), 1.57-1.34 ( m, 9H).
1-070: δ7.27-7.20 (m, 1H), 7.16-7.03 (m, 1H), 6.96-6.86 (m, 1H), 6.09 & 5.94 (s, 1H), 4.49-4.36 (m, 2H) , 4.10-3.96 (m, 2H), 3.90 & 3.89 (s, 3H), 3.74-3.62 (m, 1H), 3.29 & 3.24 (s, 3H), 2.84 & 2.82 (s, 3H), 1.74-1.01 ( m, 19H).
1-071: δ7.28-7.18 (m, 1H), 7.16-7.04 (m, 1H), 6.94-6.86 (m, 1H), 6.10-5.89 (m, 1H), 4.48-4.37 (m, 2H) , 4.08-3.98 (m, 2H), 3.92-3.86 (m, 3H), 3.82-3.68 (m, 1H), 3.30-3.06 (m, 7H), 2.85-2.78 (m, 3H), 1.86-1.13 ( m, 17H).
1-072: δ7.30-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.16-5.87 (m, 1H), 4.50-4.37 (m, 3H), 4.09-3.94 (m, 2H) , 3.94-3.86 (m, 3H), 3.73-3.33 (m, 4H), 3.30-3.21 (m, 3H), 2.86-2.79 (m, 3H), 2.14-1.97 (m, 3H), 1.67-1.19 ( m, 13H).
1-073: δ7.27-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.17-5.82 (m, 1H), 4.48-4.37 (m, 2H), 4.09-3.94 (m, 3H) , 3.93-3.87 (m, 3H), 3.58-3.08 (m, 7H), 2.85-2.77 (m, 3H), 2.34-2.18 (m, 2H), 1.72-1.34 (m, 13H), 1.13-1.03 ( m, 3H).
1-078: δ7.50-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.95-6.87 (m, 1H), 5.97-5.85 (m, 1H), 4.49-4.36 (m, 2H) , 4.09-3.94 (m, 3H), 3.93-3.88 (m, 3H), 3.77-3.73 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.78 (m, 3H), 2.43-2.15 ( m, 4H), 1.82-1.34 (m, 13H).
1-079: δ7.48-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.94-6.88 (m, 1H), 5.97 & 5.86 (s, 1H), 4.50-4.37 (m, 2H) , 4.09-3.87 (m, 3H), 3.91 & 3.90 (s, 3H), 3.62 (s, 3H), 3.50-3.11 (m, 4H), 3.28 & 3.23 (s, 3H), 2.85-2.78 (m, 3H), 1.72-1.23 (m, 13H).
1-086: δ7.28-7.07 (m, 2H), 6.98-6.84 (m, 1H), 6.09-5.88 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.22 (m, 12H) , 2.89-2.77 (m, 3H), 2.71-1.95 (m, 5H), 1.91-1.36 (m, 4H), 1.10-0.76 (m, 10H).
1-089: δ7.28-7.20 (m, 1H), 7.18-7.07 (m, 1H), 6.97-6.87 (m, 1H), 6.05-5.90 (m, 1H), 4.50-4.36 (m, 2H) , 4.10-3.94 (m, 5H), 3.93-3.88 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.79 (m, 3H), 2.46-1.93 (m, 4H), 1.79-1.62 ( m, 4H), 1.55-1.36 (m, 9H), 1.22-1.14 (m, 3H).
1-090: δ7.41-7.28 (m, 1H), 7.28-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.04-5.89 (m, 1H), 4.49-4.36 (m, 2H) , 4.10-3.96 (m, 3H), 3.93-3.86 (m, 3H), 3.29-3.19 (m, 3H), 2.85-2.78 (m, 3H), 2.48-1.95 (m, 4H), 1.82-1.61 ( m, 4H), 1.54-1.35 (m, 9H).
1-091: δ7.25-7.03 (m, 2H), 6.98-6.81 (m, 1H), 6.10-5.87 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.87 (m, 6H) , 3.62-3.56 (m, 3H), 3.32-3.22 (m, 3H), 2.86-2.79 (m, 3H), 2.28-1.17 (m, 18H).
1-092: δ7.33-7.20 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 5.98 (s, 1H), 4.52-4.37 (m, 4H), 4.07 -3.95 (m, 3H), 3.93-3.72 (m, 8H), 2.96-2.90 (m, 3H), 2.83-2.79 (m, 3H), 2.40-1.87 (m, 10H), 1.79-1.59 (m, 4H).
1-093: δ7.28-7.20 (m, 1H), 7.15-7.03 (m, 1H), 6.95-6.86 (m, 1H), 6.19-5.89 (m, 1H), 4.50-4.35 (m, 3H) , 4.09-3.94 (m, 4H), 3.93-3.81 (m, 3H), 3.80-3.71 (m, 3H), 3.70-3.59 (m, 1H), 3.04-2.93 (m, 3H), 2.84-2.69 ( m, 3H), 2.47-1.94 (m, 7H), 1.79-1.56 (m, 4H).
1-094: δ7.29-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.87 (m, 1H), 4.49-4.35 (m, 2H), 4.17-3.84 (m, 8H) , 3.56-3.03 (m, 7H), 2.84-2.76 (m, 3H), 1.76-1.14 (m, 16H).
1-096: δ7.29-7.08 (m, 2H), 6.96-6.86 (m, 1H), 5.96 (s, 1H), 4.49-4.39 (m, 2H), 4.09-3.98 (m, 3H), 3.90 (s, 3H), 3.41-2.73 (m, 10H), 2.68 (s, 3H), 1.88-1.65 (m, 4H), 1.57-1.49 (m, 9H).
1-100: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.02-5.91 (m, 1H), 4.49-4.38 (m, 2H), 4.17-3.94 (m, 4H) , 3.92-3.87 (m, 3H), 3.79-3.69 (m, 4H), 3.35-3.26 (m, 3H), 2.81 (s, 3H), 2.42-1.93 (m, 4H), 1.89-1.53 (m, 4H), 1.01-0.74 (m, 7H).
1-102: δ7.56-7.49 (m, 2H), 7.36-7.19 (m, 4H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.01-5.96 (m, 1H) , 4.49-4.35 (m, 4H), 4.07-3.89 (m, 3H), 3.91 (s, 3H), 3.75-3.71 (m, 3H), 2.92 (s, 3H), 2.83 (s, 3H), 2.40 -1.91 (m, 4H), 1.76-1.51 (m, 4H).
1-105: δ7.28-7.19 (m, 1H), 7.17-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.00-5.96 (m, 1H), 4.47-4.38 (m, 2H) , 4.07-3.70 (m, 14H), 2.96-2.91 (m, 3H), 2.84-2.81 (m, 3H), 2.52-1.59 (m, 11H).
1-106: δ7.28-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.29-6.20 (m, 1H), 6.10-5.93 (m, 2H) , 4.48-4.37 (m, 2H), 4.07-3.81 (m, 5H), 3.91 (s, 3H), 3.75 (s, 3H), 2.96 (s, 3H), 2.81 (s, 3H), 2.39-1.94 (m, 4H), 1.78-1.60 (m, 4H).
1-107: δ7.78-7.68 (m, 1H), 7.28-6.86 (m, 6H), 6.00-5.94 (m, 1H), 4.55-4.36 (m, 4H), 4.08-3.86 (m, 3H) , 3.91 (s, 3H), 3.76-3.71 (m, 3H), 2.96 (s, 3H), 2.82 (s, 3H), 2.38-1.92 (m, 4H), 1.76-1.53 (m, 4H).
1-108: δ7.29-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.04-5.85 (m, 1H), 4.50-4.39 (m, 2H), 4.18-3.94 (m, 3H) , 3.94-3.87 (m, 3H), 3.81-3.71 (m, 3H), 3.60-3.47 (m, 3H), 3.38-3.33 (m, 3H), 2.84-2.79 (m, 3H), 2.52-1.91 ( m, 7H), 1.84-1.54 (m, 4H).
1-109: δ7.25-7.08 (m, 2H), 7.04-6.88 (m, 1H), 6.07-5.88 (m, 1H), 4.49-4.39 (m, 2H), 4.08-3.88 (m, 6H) , 3.32-2.94 (m, 7H), 2.85-2.80 (m, 3H), 2.71 (s, 6H), 1.81-1.38 (m, 13H).
2-003: δ7.24-7.15 (m, 1H), 7.15-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.93 (s, 1H), 3.98-3.87 (m, 4H) ), 3.78-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.54&2.53 (s, 3H), 2.12&2.11 (s, 3H), 1.80-1.35 (m, 13H).
2-004: δ7.24-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.94 (s, 1H), 3.98-3.87 (m, 4H) ), 3.75-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.53&2.51 (s, 3H), 1.82-1.35 (m, 14H), 1.00-0.80 (m, 4H).
2-005: δ7.60-7.49 (m, 2H), 7.40-7.05 (m, 5H), 6.95-6.83 (m, 1H), 6.08-5.98 (m, 1H), 4.50-4.37 (m, 2H) , 3.98-3.84 (m, 4H), 3.70-3.51 (m, 2H), 3.39-3.22 (m, 2H), 3.00-2.89 (m, 3H), 2.54 (s, 3H), 2.11 (s, 3H) , 1.75-1.42 (m, 4H).
2-006: δ7.78-7.70 (m, 1H), 7.27-7.05 (m, 4H), 7.03-6.85 (m, 2H), 6.01 (s, 1H), 4.55-4.40 (m, 2H), 4.00 -3.85 (m, 4H), 3.69-3.50 (m, 2H), 3.39-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.79-1.45 (m, 4H).
2-007: δ7.59-7.49 (m, 2H), 7.38-7.09 (m, 5H), 6.95-6.88 (m, 1H), 5.99 (s, 1H), 4.49-4.35 (m, 2H), 3.95 -3.83 (m, 4H), 3.70-3.52 (m, 2H), 3.48 (s, 1H), 3.39-3.21 (m, 2H), 2.94 (s, 3H), 2.59 (s, 3H), 1.88-1.42 (m, 4H).
2-008: δ7.70-7.62 (m, 1H), 7.57-7.10 (m, 6H), 6.98-6.84 (m, 1H), 6.11&5.77 (s, 1H), 4.05-3.78 (m, 4H) ), 3.75-3.51 (m, 2H), 3.51&3.48 (s, 1H), 3.41-3.12 (m, 5H), 2.61&2.53 (s, 3H), 1.82-1.18 (m, 4H).
2-011: δ7.70-7.59 (m, 1H), 7.52-7.42 (m, 1H), 7.29-7.07 (m, 2H), 6.95-6.86 (m, 1H), 6.10-5.92 (m, 1H) , 4.04-3.83 (m, 4H), 3.80-3.55 (m, 2H), 3.49 (s, 3H), 3.44-3.18 (m, 2H), 2.58-2.45 (m, 3H), 2.13 (s, 3H) , 1.82-1.37 (m, 4H).
2-012: δ7.29-7.05 (m, 2H), 6.95-6.85 (m, 1H), 6.07-5.94 (m, 1H), 3.96-3.75 (m, 9H), 3.72-3.53 (m, 2H) , 3.41-3.28 (m, 2H), 3.00-2.89 (m, 3H), 2.64-2.46 (m, 3H), 2.16-2.11 (m, 3H), 2.09-2.00 (m, 3H), 1.78-1.49 ( m, 4H).
2-013: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.91 (m, 1H), 4.06-3.72 (m, 6H), 3.71-3.58 (m, 2H) , 3.41-3.26 (m, 5H), 2.55-2.45 (m, 3H), 2.17-2.06 (m, 3H), 2.05-1.80 (m, 1H), 1.76-1.45 (m, 4H), 1.07-0.70 ( m, 6H).
2-014: δ7.71-7.41 (m, 3H), 7.38-7.09 (m, 4H), 6.98-6.85 (m, 1H), 6.12&5.78 (s, 1H), 4.02-3.79 (m, 4H) ), 3.76-3.53 (m, 2H), 3.43-3.15 (m, 5H), 2.56&2.47 (s, 3H), 2.12&2.10 (s, 3H), 1.82-1.31 (m, 4H).
2-015: δ7.71-7.54 (m, 1H), 7.41-7.35 (m, 1H), 7.27-7.07 (m, 2H), 7.04-6.97 (m, 1H), 6.95-6.85 (m, 1H) , 5.84 (s, 1H), 4.00-3.80 (m, 4H), 3.78-3.59 (m, 2H), 3.41 (s, 3H), 3.32-3.15 (m, 2H), 2.59-2.47 (m, 3H) , 2.13 (s, 3H), 1.80-1.30 (m, 4H).
2-016: δ7.71-6.90 (m, 3H), 6.02 (s, 1H), 5.55 (br, 1H), 4.00-3.80 (m, 4H), 3.69-3.56 (m, 2H), 3.50 (s , 1H), 3.39-3.25 (m, 2H), 2.80 (s, 3H), 2.61 (s, 3H), 1.79-1.45 (m, 4H).
2-018: δ7.25-7.09 (m, 2H), 6.97-6.89 (m, 1H), 6.06-5.94 (m, 1H), 3.99-3.85 (m, 4H), 3.76-3.60 (m, 2H) , 3.41-3.23 (m, 5H), 2.57-2.34 (m, 6H), 2.12 (s, 3H), 1.78-1.50 (m, 4H).
2-019: δ7.29-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.94-6.87 (m, 2H), 5.99 (s, 1H), 4.70-4.53 (m, 2H), 3.98 -3.80 (m, 4H), 3.70-3.50 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.77-1.42 (m, 4H).
2-020: δ7.25-7.09 (m, 2H), 6.98-6.89 (m, 1H), 6.30-5.94 (m, 3H), 4.01-3.82 (m, 6H), 3.71-3.58 (m, 2H) , 3.40-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.12 (s, 3H), 1.78-1.44 (m, 4H).
2-022: δ8.85-8.54 (m, 1H), 8.32-8.25 (m, 1H), 7.24-7.08 (m, 2H), 6.96-6.89 (m, 1H), 6.12-5.97 (m, 1H) , 3.99-3.84 (m, 1H), 3.90 (s, 3H), 3.80-3.58 (m, 2H), 3.47 (s, 3H), 3.43-3.21 (m, 2H), 2.57-2.45 (m, 3H) , 2.12 (s, 3H), 1.83-1.42 (m, 4H).
3-001: δ7.28-7.18 (m, 2H), 7.16-6.99 (m, 2H), 6.96-6.85 (m, 2H), 6.04-5.88 (m, 1H), 4.74-4.55 (m, 2H) , 4.50 (s, 2H), 3.98-3.80 (m, 4H), 3.74-3.51 (m, 2H), 3.40-3.18 (m, 5H), 3.00 (s, 3H), 2.48 (s, 3H), 1.80 -1.44 (m, 4H).
3-002: δ7.70-7.62 (m, 1H), 7.41-7.34 (m, 1H), 7.23-7.05 (m, 2H), 7.04-6.86 (m, 2H), 6.15-5.81 (m, 1H) , 4.63-4.42 (m, 2H), 4.05-3.80 (m, 4H), 3.79-3.55 (m, 2H), 3.50-3.10 (m, 8H), 2.55-2.37 (m, 3H), 1.82-1.12 ( m, 4H).
3-003: δ8.86-8.51 (m, 1H), 8.33-8.23 (m, 1H), 7.28-7.04 (m, 2H), 6.97-6.85 (m, 1H), 6.16-5.90 (m, 1H) , 4.60-4.44 (m, 2H), 4.02-3.80 (m, 4H), 3.80-3.54 (m, 2H), 3.50-3.10 (m, 8H), 2.51-2.37 (m, 3H), 1.85-1.39 ( m, 4H).
3-004: δ7.28-7.18 (m, 2H), 7.17-7.07 (m, 1H), 7.03-6.88 (m, 2H), 6.13-6.06 (m, 1H), 4.58-4.47 (m, 2H) , 4.55-3.83 (m, 4H), 3.80-3.62 (m, 2H), 3.45-3.27 (m, 7H), 2.51-2.43 (m, 3H), 1.82-1.21 (m, 13H).
3-005: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.11-5.95 (m, 1H), 4.60-4.44 (m, 2H) , 4.05-3.75 (m, 6H), 3.75-3.57 (m, 2H), 3.43-3.24 (m, 8H), 2.52-2.42 (m, 3H), 2.08-1.80 (m, 1H), 1.80-1.47 ( m, 4H), 1.04-0.76 (m, 6H).
3-006: δ7.28-7.21 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.13-5.88 (m, 1H), 4.59-4.46 (m, 2H) , 4.02-3.76 (m, 9H), 3.76-3.57 (m, 2H), 3.42-3.26 (m, 5H), 3.01-2.92 (m, 3H), 2.53-2.45 (m, 3H), 2.10-2.02 ( m, 3H), 1.83-1.47 (m, 4H).
3-007: δ7.28-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.30-6.21 (m, 1H), 6.12-5.99 (m, 2H) , 4.54-4.49 (m, 2H), 3.98-3.83 (m, 6H), 3.73-3.57 (m, 2H), 3.40-3.26 (m, 5H), 3.03-2.92 (m, 3H), 2.53-2.43 ( m, 3H), 1.83-1.46 (m, 4H).
3-008: δ7.23-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.87 (m, 1H), 4.63-4.46 (m, 2H), 4.06-3.86 (m, 4H) , 3.79-3.51 (m, 5H), 3.42-3.21 (m, 8H), 2.52-2.41 (m, 3H), 2.12-1.96 (m, 3H), 1.82-1.44 (m, 4H).
3-009: δ7.82-7.72 (m, 1H), 7.29-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.07-5.92 (m, 1H), 4.58-4.40 (m, 4H) , 3.97-3.83 (m, 4H), 3.72-3.55 (m, 2H), 3.40-3.23 (m, 5H), 3.03-2.94 (m, 3H), 2.53-2.44 (m, 3H), 1.79-1.44 ( m, 4H).
3-010: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.12-5.93 (m, 1H), 4.59-4.45 (m, 2H) , 4.03-3.83 (m, 6H), 3.74-3.60 (m, 2H), 3.44-3.23 (m, 8H), 2.51-2.43 (m, 3H), 1.83-1.44 (m, 4H), 1.04-0.75 ( m, 9H).
3-014: δ8.13-7.23 (m, 5H), 7.23-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.23-5.75 (m, 1H), 4.63-4.39 (m, 2H) , 4.04-3.79 (m, 4H), 3.77-3.54 (m, 2H), 3.47-3.15 (m, 8H), 2.55-2.36 (m, 3H), 1.86-1.31 (m, 4H).
3-015: δ8.15-7.81 (m, 1H), 7.24-7.17 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.86 (m, 1H), 6.12-5.91 (m, 1H) , 4.57-4.41 (m, 2H), 3.99-3.81 (m, 4H), 3.79-3.54 (m, 2H), 3.50-3.20 (m, 8H), 2.50-2.40 (m, 3H), 1.83-1.40 ( m, 4H).
3-016: δ8.17-8.07 (m, 1H), 7.23-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.16-5.84 (m, 1H), 4.57-4.43 (m, 2H) , 4.00-3.84 (m, 4H), 3.79-3.53 (m, 2H), 3.51-3.21 (m, 8H), 2.53-2.39 (m, 3H), 1.82-0.98 (m, 13H).
3-017: δ7.51-7.45 (m, 1H), 7.23-7.06 (m, 2H), 6.95-6.86 (m, 1H), 6.69-6.62 (m, 1H), 6.15-5.83 (m, 1H) , 4.62-4.43 (m, 2H), 4.04-3.78 (m, 4H), 3.78-3.56 (m, 2H), 3.46-3.11 (m, 8H), 2.56-2.35 (m, 6H), 1.81-1.29 ( m, 4H).
3-018: δ7.50-7.42 (m, 1H), 7.22-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.88-6.81 (m, 1H), 6.13-5.79 (m, 1H) , 4.60-4.46 (m, 2H), 4.03-3.82 (m, 4H), 3.80-3.56 (m, 2H), 3.49-3.12 (m, 8H), 2.54-2.42 (m, 3H), 1.83-1.34 ( m, 4H).
3-019: δ7.27-7.05 (m, 2H), 6.96-6.87 (m, 1H), 6.14-5.89 (m, 1H), 4.57-4.46 (m, 2H), 3.98-3.86 (m, 4H) , 3.77-3.60 (m, 2H), 3.48-3.17 (m, 8H), 2.72-2.08 (m, 4H), 2.06-1.01 (m, 14H).
3-020: δ7.27-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.14-5.88 (m, 1H), 4.60-4.45 (m, 2H), 4.00-3.86 (m, 4H) , 3.76-3.60 (m, 2H), 3.50-3.21 (m, 8H), 3.14-2.52 (m, 1H), 2.52-2.41 (m, 3H), 2.08-1.36 (m, 12H).
3-021: δ7.28-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.18-5.92 (m, 1H), 4.59-4.44 (m, 2H), 4.04-3.84 (m, 4H) , 3.77-3.60 (m, 2H), 3.52-3.21 (m, 8H), 2.74-2.06 (m, 4H), 1.88-1.36 (m, 8H), 1.10-0.77 (m, 6H).
3-022: δ7.26-7.18 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 6.15-5.86 (m, 2H), 4.58-4.41 (m, 2H) , 4.10-4.01 (m, 1H), 3.99-2.98 (m, 15H), 2.53-2.43 (m, 3H), 1.81-1.41 (m, 4H).
3-023: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.12-5.95 (m, 1H), 4.86-4.62 (m, 1H) , 4.60-4.45 (m, 2H), 4.07-3.22 (m, 14H), 2.54-2.42 (m, 3H), 2.00-1.10 (m, 14H).
3-024: δ7.27-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.95-6.87 (m, 2H), 6.07-5.89 (m, 1H), 4.73-4.49 (m, 4H) , 3.97-3.80 (m, 4H), 3.72-3.45 (m, 4H), 3.39-3.21 (m, 2H), 3.07-2.92 (m, 3H), 2.55-2.39 (m, 3H), 1.78-1.42 ( m, 4H), 1.30-1.13 (m, 3H).
3-025: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.10-5.94 (m, 1H), 4.65-4.49 (m, 2H), 4.05-3.46 (m, 10H) , 3.42-3.25 (m, 5H), 2.51-2.42 (m, 3H), 2.07-1.81 (m, 1H), 1.80-1.47 (m, 4H), 1.30-1.17 (m, 3H), 1.02-0.75 ( m, 6H).
3-026: δ7.68-7.61 (m, 1H), 7.36-7.30 (m, 1H), 7.21-7.08 (m, 2H), 6.98-6.87 (m, 2H), 6.11-5.72 (m, 1H) , 4.62-4.45 (m, 2H), 3.99-3.76 (m, 4H), 3.76-3.19 (m, 11H), 3.11-2.77 (m, 2H), 2.53-2.42 (m, 3H), 1.73-1.18 ( m, 4H).
3-027: δ7.73-7.64 (m, 1H), 7.52-6.81 (m, 5H), 5.76-5.25 (m, 1H), 4.63-4.47 (m, 2H), 4.34-4.07 (m, 1H) , 3.90-3.79 (m, 4H), 3.54-3.32 (m, 6H), 2.87-2.45 (m, 6H), 1.33-1.10 (m, 3H).
3-028: δ7.40-6.74 (m, 5H), 6.14-5.78 (m, 1H), 4.63-4.43 (m, 2H), 4.03-2.89 (m, 17H), 2.57-2.39 (m, 6H) , 1.72-1.21 (m, 4H).
3-029: δ8.87-7.90 (m, 2H), 7.25-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.11-5.88 (m, 1H), 4.61-4.44 (m, 2H) , 4.01-2.98 (m, 17H), 2.55-2.39 (m, 3H), 1.75-1.16 (m, 4H).
3-030: δ8.90-7.26 (m, 3H), 7.19-7.02 (m, 2H), 6.92-6.82 (m, 1H), 5.69-5.29 (m, 1H), 4.61-4.44 (m, 2H) , 4.35-4.16 (m, 1H), 3.93-3.76 (m, 3H), 3.54-3.31 (m, 6H), 2.87-2.30 (m, 6H), 1.39-1.16 (m, 3H).
3-031: δ8.12-7.07 (m, 7H), 6.96-6.86 (m, 1H), 6.13-5.75 (m, 1H), 4.61-4.38 (m, 2H), 4.04-2.91 (m, 17H) , 2.54-2.35 (m, 3H), 1.72-1.21 (m, 4H).
3-032: δ7.25-7.17 (m, 2H), 7.15-7.06 (m, 1H), 7.05-6.99 (m, 1H), 6.94-6.84 (m, 2H), 6.06-5.87 (m, 1H) , 4.74-4.41 (m, 4H), 3.97-3.82 (m, 4H), 3.69-3.55 (m, 3H), 3.45-3.07 (m, 7H), 3.04-2.95 (m, 3H), 2.53-2.41 ( m, 3H), 1.72-1.41 (m, 4H).
3-034: δ7.25-7.17 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.28-6.19 (m, 1H), 6.11-5.95 (m, 2H) , 4.65-4.43 (m, 2H), 4.00-3.81 (m, 6H), 3.65-3.55 (m, 3H), 3.50-3.10 (m, 7H), 3.00-2.92 (m, 3H), 2.53-2.43 ( m, 3H), 1.73-1.44 (m, 4H).
3-035: δ7.85-7.47 (m, 1H), 7.22-7.02 (m, 2H), 6.93-6.83 (m, 1H), 6.45-5.94 (m, 2H), 5.59-5.44 (m, 1H) , 4.57-4.45 (m, 2H), 4.35-4.22 (m, 1H), 4.06-3.78 (m, 5H), 3.45-3.33 (m, 3H), 3.10-2.95 (m, 3H), 2.95-2.78 ( m, 3H), 2.55-2.39 (m, 3H), 1.41-1.30 (m, 3H).
3-036: δ7.80-7.71 (m, 1H), 7.27-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.09-5.88 (m, 1H), 4.59-4.39 (m, 4H) , 3.99-3.82 (m, 4H), 3.66-3.56 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.94 (m, 3H), 2.53-2.43 (m, 3H), 1.71-1.43 ( m, 4H).
3-037: δ7.24-7.06 (m, 2H), 6.95-6.87 (m, 1H), 6.05-5.92 (m, 1H), 4.59-4.43 (m, 2H), 4.06-3.86 (m, 6H) , 3.81-3.15 (m, 13H), 2.54-2.41 (m, 3H), 2.12-1.75 (m, 1H), 1.74-1.46 (m, 4H), 1.07-0.73 (m, 6H).
3-038: δ7.79-7.47 (m, 1H), 7.25-7.01 (m, 2H), 6.92-6.82 (m, 1H), 5.67-5.46 (m, 1H), 4.62-4.45 (m, 2H) , 4.35-4.21 (m, 1H), 4.06-3.69 (m, 5H), 3.48-3.25 (m, 6H), 2.90-2.73 (m, 3H), 2.55-2.37 (m, 3H), 2.14-1.74 ( m, 1H), 1.40-0.73 (m, 9H).
3-039: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.07-5.90 (m, 1H), 4.60-4.40 (m, 2H) , 4.00-3.76 (m, 9H), 3.66-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.00-2.89 (m, 3H), 2.56-2.44 (m, 3H), 2.09-2.01 ( m, 3H), 1.71-1.47 (m, 4H).
3-041: δ7.25-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.07-5.84 (m, 1H), 4.62-4.40 (m, 2H), 4.04-3.83 (m, 4H) , 3.73-2.92 (m, 16H), 2.52-2.43 (m, 3H), 2.12-1.95 (m, 3H), 1.78-1.39 (m, 4H).
3-042: δ7.76-7.52 (m, 1H), 7.22-7.00 (m, 2H), 6.92-6.83 (m, 1H), 5.72-5.25 (m, 1H), 4.62-4.45 (m, 2H) , 4.35-4.21 (m, 1H), 4.07-3.27 (m, 12H), 2.86-2.74 (m, 3H), 2.53-2.39 (m, 3H), 2.14-1.92 (m, 3H), 1.41-1.21 ( m, 3H).
3-043: δ7.25-7.07 (m, 2H), 7.02-6.87 (m, 2H), 6.10-5.93 (m, 1H), 4.58-4.41 (m, 2H), 4.04-3.11 (m, 17H) , 2.51-2.39 (m, 3H), 1.72-1.49 (m, 4H), 1.33-1.18 (m, 9H).
3-044: δ7.61-7.39 (m, 5H), 6.12-6.02 (m, 1H), 4.59-4.44 (m, 2H), 4.10-3.93 (m, 3H), 3.85-3.57 (m, 3H) , 3.56-3.07 (m, 10H), 2.55-2.39 (m, 3H), 2.10-1.78 (m, 1H), 1.77-1.46 (m, 4H), 1.06-0.75 (m, 6H).
3-045: δ7.58-7.35 (m, 5H), 5.49-5.23 (m, 1H), 4.64-4.43 (m, 2H), 4.20-3.65 (m, 3H), 3.45-3.16 (m, 6H) , 2.98-2.70 (m, 3H), 2.54-2.37 (m, 3H), 2.11-1.75 (m, 1H), 1.66-1.37 (m, 3H), 1.31-0.71 (m, 6H).
*Protons derived from NH were not observed.
3-046: δ7.62-7.54 (m, 2H), 7.50-7.38 (m, 3H), 6.14-6.04 (m, 1H), 4.60-4.44 (m, 2H), 4.12-3.75 (m, 3H) , 3.74-3.59 (m, 2H), 3.44-3.24 (m, 8H), 2.56-2.41 (m, 3H), 2.08-1.48 (m, 5H), 1.06-0.76 (m, 6H).
3-047: δ7.64-7.54 (m, 2H), 7.49-7.38 (m, 3H), 6.17-6.02 (m, 1H), 4.62-4.41 (m, 2H), 4.08-3.95 (m, 1H) , 3.93-3.75 (m, 5H), 3.66-3.58 (m, 3H), 3.50-3.28 (m, 5H), 3.27-3.10 (m, 2H), 3.00-2.87 (m, 3H), 2.55-2.40 ( m, 3H), 2.14-1.98 (m, 3H), 1.78-1.49 (m, 4H).
3-049: δ7.62-7.55 (m, 2H), 7.48-7.38 (m, 3H), 6.17-6.04 (m, 1H), 4.58-4.43 (m, 2H), 4.08-3.95 (m, 1H) , 3.92-3.72 (m, 5H), 3.72-3.58 (m, 2H), 3.39-3.26 (m, 5H), 3.02-2.88 (m, 3H), 2.51-2.45 (m, 3H), 2.09-2.01 ( m, 3H), 1.85-1.49 (m, 4H).
3-050: δ7.61-7.54 (m, 2H), 7.49-7.41 (m, 3H), 7.23-7.18 (m, 1H), 7.05-7.01 (m, 1H), 6.92-6.86 (m, 1H) , 6.13-6.01 (m, 1H), 4.73-4.55 (m, 2H), 4.55-4.43 (m, 2H), 4.04-3.93 (m, 1H), 3.70-3.56 (m, 3H), 3.51-3.32 ( m, 5H), 3.25-3.04 (m, 2H), 3.03-2.96 (m, 3H), 2.54-2.42 (m, 3H), 1.75-1.42 (m, 4H).
3-051: δ7.56-7.36 (m, 5H), 7.29-7.16 (m, 1H), 7.02-6.79 (m, 2H), 5.47-5.22 (m, 1H), 4.94-4.67 (m, 1H) , 4.57-3.71 (m, 4H), 3.44-3.25 (m, 3H), 3.14-2.72 (m, 6H), 2.52-2.35 (m, 3H), 1.48-0.72 (m, 3H).
*Protons derived from NH were not observed.
3-052: δ7.62-7.55 (m, 2H), 7.48-7.41 (m, 3H), 7.24-7.19 (m, 1H), 7.06-7.01 (m, 1H), 6.93-6.87 (m, 1H) , 6.10-6.06 (m, 1H), 4.73-4.55 (m, 2H), 4.51-4.46 (m, 2H), 4.07-3.93 (m, 1H), 3.72-3.56 (m, 2H), 3.39-3.20 ( m, 5H), 3.04-2.96 (m, 3H), 2.52-2.45 (m, 3H), 1.82-1.45 (m, 4H).
3-054: δ7.58-7.38 (m, 5H), 6.34-6.13 (m, 1H), 6.08-5.92 (m, 1H), 5.48-5.22 (m, 1H), 4.64-3.70 (m, 6H) , 3.43-3.28 (m, 3H), 3.02-2.74 (m, 6H), 2.54-2.39 (m, 3H), 1.48-0.97 (m, 3H).
3-055: δ7.68-7.38 (m, 5H), 6.33-5.98 (m, 3H), 4.60-4.43 (m, 2H), 4.19-3.83 (m, 3H), 3.76-3.61 (m, 2H) , 3.48-3.26 (m, 5H), 3.08-2.92 (m, 3H), 2.58-2.42 (m, 3H), 1.87-1.49 (m, 4H).
3-056: δ7.83-7.69 (m, 1H), 7.62-7.54 (m, 2H), 7.49-7.40 (m, 3H), 7.24-7.16 (m, 1H), 7.15-7.07 (m, 1H) , 7.04-6.94 (m, 1H), 6.15-6.02 (m, 1H), 4.57-4.40 (m, 4H), 4.07-3.94 (m, 1H), 3.65-3.57 (m, 3H), 3.48-3.28 ( m, 5H), 3.26-3.06 (m, 2H), 3.04-2.91 (m, 3H), 2.54-2.41 (m, 3H), 1.83-1.43 (m, 4H).
3-057: δ7.76-7.36 (m, 6H), 7.24-7.15 (m, 1H), 7.15-6.92 (m, 2H), 5.55-5.11 (m, 1H), 4.61-4.27 (m, 4H) , 4.07-3.77 (m, 1H), 3.42-3.26 (m, 3H), 3.05-2.79 (m, 6H), 2.52-2.37 (m, 3H), 1.47-0.85 (m, 3H).
*Protons derived from NH were not observed.
3-058: δ7.80-7.71 (m, 1H), 7.62-7.55 (m, 2H), 7.48-7.39 (m, 3H), 7.27-7.16 (m, 1H), 7.16-7.08 (m, 1H) , 7.04-6.95 (m, 1H), 6.17-6.04 (m, 1H), 4.58-4.41 (m, 4H), 4.08-3.96 (m, 1H), 3.71-3.56 (m, 2H), 3.43-3.21 ( m, 5H), 3.04-2.90 (m, 3H), 2.55-2.42 (m, 3H), 1.83-1.42 (m, 4H).
3-059: δ7.69-7.31 (m, 7H), 7.00-6.93 (m, 1H), 6.16-5.88 (m, 1H), 4.61-4.45 (m, 2H), 4.03-3.87 (m, 1H) , 3.75-2.65 (m, 13H), 2.55-2.40 (m, 3H), 1.82-1.30 (m, 4H).
3-061: δ7.68-7.36 (m, 7H), 7.03-6.97 (m, 1H), 6.17-5.90 (m, 1H), 4.59-4.45 (m, 2H), 4.06-3.92 (m, 1H) , 3.79-3.57 (m, 2H), 3.47-3.33 (m, 6H), 3.31-3.09 (m, 2H), 2.54-2.40 (m, 3H), 1.87-1.29 (m, 4H).
3-062: δ7.64-6.75 (m, 7H), 6.18-5.92 (m, 1H), 4.60-4.42 (m, 2H), 4.18-3.88 (m, 1H), 3.76-2.79 (m, 13H) , 2.57-2.40 (m, 6H), 1.81-1.20 (m, 4H).
3-064: δ7.64-6.75 (m, 7H), 6.19-5.95 (m, 1H), 4.60-4.42 (m, 2H), 4.17-3.91 (m, 1H), 3.78-3.58 (m, 2H) , 3.46-3.10 (m, 8H), 2.57-2.39 (m, 6H), 1.89-1.33 (m, 4H).
3-065: δ7.73-7.19 (m, 10H), 6.18-5.88 (m, 1H), 4.62-4.39 (m, 2H), 4.18-3.81 (m, 1H), 3.78-2.80 (m, 13H) , 2.57-2.41 (m, 3H), 1.81-1.17 (m, 4H).
3-067: δ7.71-7.22 (m, 10H), 6.19-5.89 (m, 1H), 4.60-4.42 (m, 2H), 4.03-3.82 (m, 1H), 3.76-3.54 (m, 2H) , 3.45-3.09 (m, 8H), 2.54-2.40 (m, 3H), 1.88-1.21 (m, 4H).
3-068: δ7.62-7.38 (m, 5H), 7.05-6.94 (m, 1H), 6.15-6.04 (m, 1H), 4.59-4.45 (m, 2H), 4.18-4.03 (m, 1H) , 3.86-3.11 (m, 13H), 2.52-2.41 (m, 3H), 1.81-1.46 (m, 4H), 1.33-1.19 (m, 9H).
3-069: δ7.57-7.33 (m, 5H), 7.10-6.95 (m, 1H), 5.53-5.12 (m, 1H), 4.66-4.42 (m, 2H), 4.18-3.87 (m, 1H) , 3.81-3.22 (m, 6H), 2.99-2.74 (m, 3H), 2.47-2.38 (m, 3H), 1.53-1.37 (m, 3H), 1.36-1.16 (m, 9H).
*Protons derived from NH were not observed.
3-070: δ7.62-7.39 (m, 5H), 6.13-5.96 (m, 1H), 4.59-4.45 (m, 2H), 4.10-2.93 (m, 17H), 2.54-2.40 (m, 3H) , 2.13-1.97 (m, 3H), 1.82-1.40 (m, 4H).
3-072: δ7.62-7.52 (m, 2H), 7.51-7.40 (m, 3H), 6.15-5.97 (m, 1H), 4.61-4.45 (m, 2H), 4.10-3.21 (m, 14H) , 2.54-2.40 (m, 3H), 2.13-1.97 (m, 3H), 1.86-1.47 (m, 4H).
3-073: δ8.95-7.35 (m, 7H), 6.17-6.02 (m, 1H), 4.61-4.44 (m, 2H), 4.16-2.89 (m, 14H), 2.54-2.39 (m, 3H) , 1.84-1.17 (m, 4H).
3-075: δ8.87-7.37 (m, 7H), 6.18-6.06 (m, 1H), 4.59-4.44 (m, 2H), 4.17-3.97 (m, 1H), 3.87-3.15 (m, 10H) , 2.52-2.40 (m, 3H), 1.87-1.42 (m, 4H).
3-076: δ7.51-6.86 (m, 7H), 5.94-5.80 (m, 1H), 4.73-4.57 (m, 2H), 4.54-4.44 (m, 2H), 3.97-3.87 (m, 4H) , 3.70-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.05-2.97 (m, 3H), 2.53-2.43 (m, 3H), 1.76-1.44 (m, 4H).
3-077: δ7.51-7.37 (m, 2H), 7.22-7.16 (m, 1H), 7.06-6.85 (m, 4H), 5.92-5.81 (m, 1H), 4.73-4.45 (m, 4H) , 3.95-3.83 (m, 4H), 3.65-3.57 (m, 3H), 3.46-3.07 (m, 7H), 3.05-2.95 (m, 3H), 2.53-2.42 (m, 3H), 1.71-1.18 ( m, 4H).
3-078: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 6.30-6.21 (m, 1H), 6.12-6.00 (m, 1H), 5.94-5.80 (m, 1H) , 4.57-4.47 (m, 2H), 4.01-3.25 (m, 13H), 3.03-2.94 (m, 3H), 2.54-2.44 (m, 3H), 1.78-1.47 (m, 4H).
3-079: δ7.50-7.38 (m, 2H), 7.07-6.93 (m, 2H), 6.28-6.19 (m, 1H), 6.11-5.99 (m, 1H), 5.86-5.78 (m, 1H) , 4.56-4.48 (m, 2H), 4.00-3.83 (m, 6H), 3.65-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.01-2.93 (m, 3H), 2.53-2.43 ( m, 3H), 1.70-1.18 (m, 4H).
3-080: δ7.84-6.93 (m, 8H), 5.95-5.86 (m, 1H), 4.59-4.40 (m, 4H), 4.00-3.85 (m, 4H), 3.70-3.53 (m, 2H) , 3.41-3.22 (m, 5H), 3.04-2.94 (m, 3H), 2.53-2.45 (m, 3H), 1.78-1.44 (m, 4H).
3-081: δ7.82-6.92 (m, 8H), 5.95-5.83 (m, 1H), 4.57-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.64-3.56 (m, 2H) , 3.45-3.10 (m, 8H), 3.01-2.92 (m, 3H), 2.52-2.44 (m, 3H), 1.70-1.21 (m, 4H).
3-082: δ7.52-7.39 (m, 2H), 7.33-7.28 (m, 1H), 7.26-7.20 (m, 2H), 7.06-6.94 (m, 2H), 5.95-5.85 (m, 1H) , 4.55-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.72-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.04-2.95 (m, 3H), 2.52-2.45 ( m, 3H), 1.78-1.47 (m, 4H).
3-083: δ7.51-7.38 (m, 2H), 7.31-7.26 (m, 1H), 7.25-7.18 (m, 2H), 7.05-6.93 (m, 2H), 5.90-5.81 (m, 1H) , 4.54-4.38 (m, 4H), 3.96-3.84 (m, 4H), 3.66-3.57 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.92 (m, 3H), 2.52-2.42 ( m, 3H), 1.70-1.17 (m, 4H).
3-084: δ8.86-7.38 (m, 4H), 7.05-6.92 (m, 2H), 5.99-5.82 (m, 1H), 4.58-4.45 (m, 2H), 4.02-3.18 (m, 17H) , 2.51-2.37 (m, 3H), 1.80-1.37 (m, 4H).
3-085: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.95-5.87 (m, 1H), 4.56-4.48 (m, 2H), 3.98-3.77 (m, 9H) , 3.71-3.55 (m, 2H), 3.39-3.24 (m, 5H), 2.99-2.91 (m, 3H), 2.53-2.44 (m, 3H), 2.09-2.02 (m, 3H), 1.78-1.48 ( m, 4H).
3-086: δ7.51-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.87-5.84 (m, 1H), 4.55-4.48 (m, 2H), 3.97-3.75 (m, 9H) , 3.74-3.59 (m, 5H), 3.43-3.13 (m, 5H), 2.97-2.91 (m, 3H), 2.51-2.44 (m, 3H), 2.07-2.02 (m, 3H), 1.66-1.50 ( m, 4H).
3-087: δ7.49-7.37 (m, 2H), 7.08-6.93 (m, 2H), 5.95-5.82 (m, 1H), 4.60-4.45 (m, 2H), 4.05-3.22 (m, 16H) , 2.53-2.43 (m, 3H), 2.06-1.80 (m, 1H), 1.78-1.47 (m, 4H), 1.03-0.75 (m, 6H).
3-088: δ7.49-7.37 (m, 2H), 7.06-6.93 (m, 2H), 5.90-5.80 (m, 1H), 4.61-4.46 (m, 2H), 4.06-3.14 (m, 19H) , 2.53-2.42 (m, 3H), 2.08-1.73 (m, 1H), 1.68-1.16 (m, 4H), 1.03-0.73 (m, 6H).
3-089: δ7.71-7.65 (m, 1H), 7.50-7.36 (m, 3H), 7.06-6.93 (m, 3H), 6.02-5.70 (m, 1H), 4.60-4.46 (m, 2H) , 4.03-3.13 (m, 14H), 2.53-2.42 (m, 3H), 1.78-1.30 (m, 4H).
3-090: δ7.93-6.91 (m, 7H), 5.99-5.52 (m, 1H), 4.62-4.47 (m, 2H), 4.01-2.79 (m, 17H), 2.53-2.41 (m, 3H) , 1.69-1.14 (m, 4H).
3-091: δ7.54-6.79 (m, 6H), 6.04-5.71 (m, 1H), 4.60-4.44 (m, 2H), 4.03-3.81 (m, 4H), 3.75-3.57 (m, 2H) , 3.45-3.15 (m, 8H), 2.59-2.39 (m, 6H), 1.79-1.16 (m, 4H).
3-092: δ7.55-6.76 (m, 6H), 6.02-5.68 (m, 1H), 4.63-4.45 (m, 2H), 4.04-2.91 (m, 17H), 2.61-2.39 (m, 6H) , 1.69-1.13 (m, 4H).
3-093: δ7.62-7.06 (m, 6H), 6.59-6.40 (m, 1H), 6.23-6.00 (m, 1H), 4.60-4.46 (m, 2H), 4.04-3.91 (m, 1H) , 3.81-3.14 (m, 10H), 2.53-2.41 (m, 3H), 1.87-1.47 (m, 4H).
3-094: δ8.73-7.20 (m, 8H), 6.26-6.03 (m, 1H), 4.61-4.43 (m, 2H), 4.11-3.91 (m, 1H), 3.79-3.17 (m, 10H) , 2.53-2.37 (m, 3H), 1.88-1.20 (m, 4H).
3-095: δ7.65-7.20 (m, 4H), 6.21-6.06 (m, 1H), 4.63-4.45 (m, 2H), 4.10-3.99 (m, 1H), 3.78-3.65 (m, 2H) , 3.48-3.22 (m, 8H), 2.55-2.45 (m, 3H), 2.45-1.95 (m, 2H), 1.88-1.47 (m, 4H), 1.08-0.83 (m, 7H).
3-096: δ8.77-7.20 (m, 7H), 6.21-5.87 (m, 1H), 4.61-4.43 (m, 2H), 4.04-3.90 (m, 1H), 3.78-3.63 (m, 2H) , 3.44-3.15 (m, 8H), 2.52-2.40 (m, 3H), 1.82-1.34 (m, 4H).
3-097: δ8.00-7.34 (m, 6H), 6.21-6.06 (m, 1H), 4.60-4.46 (m, 2H), 4.09-3.94 (m, 1H), 3.82-3.58 (m, 2H) , 3.53-3.16 (m, 8H), 2.51-2.39 (m, 3H), 1.88-1.39 (m, 4H).
3-099: δ7.61-7.27 (m, 5H), 6.66-6.26 (m, 1H), 6.19-5.95 (m, 1H), 4.56-4.46 (m, 2H), 4.10-3.90 (m, 4H) , 3.79-3.65 (m, 2H), 3.51-3.16 (m, 8H), 2.52-2.39 (m, 3H), 1.88-1.13 (m, 4H).
3-100: δ7.91-7.32 (m, 6H), 6.22-5.95 (m, 1H), 4.57-4.47 (m, 2H), 4.03-3.13 (m, 14H), 2.82-2.42 (m, 3H) , 1.87-1.17 (m, 4H).
3-102: δ7.88-6.88 (m, 6H), 6.25-5.99 (m, 1H), 4.60-4.44 (m, 2H), 4.11-3.89 (m, 1H), 3.79-3.62 (m, 2H) , 3.49-3.16 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.31 (m, 4H).
3-103: δ8.70-7.36 (m, 7H), 6.25-5.99 (m, 1H), 4.60-4.45 (m, 2H), 4.10-3.93 (m, 1H), 3.80-3.18 (m, 10H) , 2.52-2.36 (m, 3H), 1.88-1.33 (m, 4H).
3-104: δ8.08-8.02 (m, 1H), 7.75-7.67 (m, 1H), 7.61-7.23 (m, 5H), 6.23-6.05 (m, 1H), 4.58-4.49 (m, 2H) , 4.08-3.92 (m, 1H), 3.78-3.18 (m, 10H), 2.52-2.38 (m, 3H), 1.86-1.33 (m, 4H).
3-105: δ7.29-6.81 (m, 6H), 6.01-5.89 (m, 1H), 4.73-4.39 (m, 4H), 4.02-3.68 (m, 7H), 3.40-3.29 (m, 3H) , 3.05-2.92 (m, 3H), 2.53-2.42 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H).
3-106: δ7.31-7.05 (m, 5H), 6.97-6.87 (m, 1H), 6.01-5.89 (m, 1H), 4.55-4.37 (m, 4H), 4.02-3.68 (m, 7H) , 3.39-3.29 (m, 3H), 3.01-2.89 (m, 3H), 2.52-2.43 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H).
3-107: δ7.59-7.50 (m, 2H), 7.35-7.17 (m, 4H), 7.17-7.06 (m, 1H), 6.97-6.87 (m, 1H), 6.04-5.91 (m, 1H) , 4.55-4.34 (m, 4H), 4.02-3.68 (m, 7H), 3.39-3.29 (m, 3H), 2.96-2.86 (m, 3H), 2.52-2.45 (m, 3H), 2.45-1.88 ( m, 4H), 1.83-1.51 (m, 4H).
3-108: δ7.82-7.72 (m, 1H), 7.30-6.88 (m, 6H), 6.04-5.93 (m, 1H), 4.57-4.39 (m, 4H), 4.02-3.60 (m, 7H) , 3.40-3.30 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.89 (m, 4H), 1.84-1.53 (m, 4H).
3-109: δ7.27-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.89 (m, 1H), 6.29-6.20 (m, 1H), 6.11-5.89 (m, 2H) , 4.56-4.43 (m, 2H), 4.04-3.73 (m, 9H), 3.40-3.31 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.43 (m, 3H), 2.43-1.92 ( m, 4H), 1.85-1.54 (m, 4H).
3-110: δ7.28-7.18 (m, 1H), 7.18-7.07 (m, 1H), 6.96-6.86 (m, 1H), 6.05-5.89 (m, 1H), 4.59-4.44 (m, 2H) , 4.07-3.95 (m, 1H), 3.94-3.69 (m, 6H), 3.58-3.13 (m, 6H), 2.50-2.40 (m, 3H), 2.41-1.91 (m, 4H), 1.89-1.14 ( m, 13H).
3-111: δ7.62-7.20 (m, 7H), 7.01-6.90 (m, 1H), 6.19-6.08 (m, 1H), 4.63-4.36 (m, 4H), 4.02-3.92 (m, 1H) , 3.66-3.56 (m, 3H), 3.47-3.03 (m, 7H), 2.98-2.87 (m, 3H), 2.54-2.43 (m, 3H), 1.74-1.37 (m, 4H).
3-112: δ7.61-6.95 (m, 8H), 6.17-6.07 (m, 1H), 4.61-4.33 (m, 4H), 4.02-3.91 (m, 1H), 3.67-3.56 (m, 3H) , 3.46-3.05 (m, 7H), 2.96-2.87 (m, 3H), 2.53-2.44 (m, 3H), 1.73-1.41 (m, 4H).
3-113: δ7.61-7.08 (m, 8H), 6.20-6.09 (m, 1H), 4.56-4.34 (m, 4H), 4.01-3.89 (m, 1H), 3.69-3.56 (m, 3H) , 3.47-3.30 (m, 5H), 3.25-3.09 (m, 2H), 2.99-2.87 (m, 3H), 2.54-2.42 (m, 6H), 1.75-1.42 (m, 4H).
3-114: δ7.75-7.35 (m, 5H), 7.25-7.17 (m, 1H), 6.98-6.91 (m, 1H), 6.85-6.80 (m, 1H), 6.21-6.09 (m, 1H) , 4.57-4.34 (m, 4H), 4.02-3.92 (m, 1H), 3.85-3.73 (m, 3H), 3.67-3.56 (m, 3H), 3.46-3.29 (m, 5H), 3.26-3.07 ( m, 2H), 3.03-2.93 (m, 3H), 2.55-2.43 (m, 3H), 1.73-1.42 (m, 4H).
3-115: δ7.60-7.17 (m, 5H), 6.89-6.82 (m, 2H), 6.21-6.10 (m, 1H), 4.57-4.39 (m, 4H), 4.03-3.93 (m, 1H) , 3.68-3.57 (m, 3H), 3.53-3.31 (m, 5H), 3.26-3.10 (m, 2H), 3.10-3.00 (m, 3H), 2.51-2.36 (m, 3H), 1.77-1.45 ( m, 4H).
3-116: δ7.61-7.35 (m, 4H), 7.13-7.09 (m, 1H), 6.79-6.74 (m, 1H), 6.19-6.10 (m, 1H), 4.68-4.43 (m, 4H) , 4.01-3.91 (m, 1H), 3.68-3.58 (m, 3H), 3.48-3.30 (m, 5H), 3.26-3.06 (m, 2H), 3.02-2.93 (m, 3H), 2.52-2.43 ( m, 3H), 2.31-2.21 (m, 3H), 1.74-1.42 (m, 4H).
3-117: δ8.90-7.03 (m, 6H), 6.20-6.10 (m, 1H), 4.89-4.47 (m, 4H), 4.05-3.92 (m, 1H), 3.66-3.58 (m, 3H) , 3.47-3.29 (m, 5H), 3.25-3.01 (m, 5H), 2.52-2.45 (m, 3H), 1.76-1.42 (m, 4H).
3-118: δ7.61-7.35 (m, 5H), 6.13-6.04 (m, 1H), 4.64-4.46 (m, 4H), 4.04-3.93 (m, 1H), 3.68-3.58 (m, 3H) , 3.47-3.30 (m, 5H), 3.26-3.07 (m, 2H), 3.03-2.91 (m, 3H), 2.53-2.41 (m, 3H), 1.74-1.44 (m, 4H).
3-119: δ8.46-7.21 (m, 7H), 6.15-6.03 (m, 1H), 4.77-4.36 (m, 4H), 4.04-3.93 (m, 1H), 3.67-3.56 (m, 3H) , 3.45-3.06 (m, 7H), 2.98-2.89 (m, 3H), 2.52-2.41 (m, 3H), 1.74-1.44 (m, 4H).
3-120: δ7.61-7.36 (m, 4H), 6.20-6.08 (m, 1H), 4.59-4.46 (m, 2H), 4.05-3.93 (m, 1H), 3.69-3.56 (m, 3H) , 3.52-3.32 (m, 5H), 3.24-3.08 (m, 4H), 3.07-2.97 (m, 3H), 2.54-2.43 (m, 3H), 1.79-1.48 (m, 4H), 1.04-0.89 ( m, 1H), 0.46-0.32 (m, 2H), 0.15-0.06 (m, 2H).
3-121: δ7.61-7.36 (m, 4H), 6.20-5.94 (m, 3H), 4.57-4.46 (m, 2H), 4.18-4.08 (m, 2H), 4.04-3.94 (m, 1H) , 3.67-3.61 (m, 3H), 3.49-3.32 (m, 5H), 3.27-3.10 (m, 2H), 3.07-3.00 (m, 3H), 2.51-2.42 (m, 3H), 1.76-1.45 ( m, 4H).
3-122: δ8.97-7.33 (m, 7H), 7.29-7.20 (m, 1H), 6.22-5.91 (m, 1H), 4.56-4.43 (m, 2H), 4.09-3.86 (m, 1H) , 3.78-3.58 (m, 2H), 3.46-3.14 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.29 (m, 4H).
3-125: δ7.90-7.83 (m, 2H), 7.37-7.20 (m, 4H), 7.15-7.05 (m, 1H), 6.94-6.87 (m, 1H), 5.98-5.85 (m, 1H) , 4.64-4.34 (m, 4H), 4.00-3.71 (m, 10H), 3.40-3.28 (m, 3H), 3.08-2.98 (m, 3H), 2.49-2.41 (m, 3H), 2.39-1.86 ( m, 4H), 1.82-1.53 (m, 4H).
3-126: δ7.28-7.21 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.03-5.91 (m, 1H), 4.55-4.42 (m, 2H) , 4.02-3.70 (m, 12H), 3.39-3.30 (m, 3H), 2.96-2.89 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.91 (m, 7H), 1.84-1.51 ( m, 4H).
3-128: δ7.86-7.06 (m, 5H), 6.96-6.87 (m, 1H), 6.09-5.78 (m, 1H), 4.57-4.41 (m, 2H), 4.07-3.72 (m, 7H) , 3.50-3.32 (m, 6H), 2.57-1.88 (m, 7H), 1.87-1.31 (m, 4H).
3-129: δ8.86-8.25 (m, 2H), 7.24-7.18 (m, 1H), 7.16-7.08 (m, 1H), 6.96-6.87 (m, 1H), 6.08-5.91 (m, 1H) , 4.59-4.43 (m, 2H), 4.06-3.73 (m, 7H), 3.50-3.32 (m, 6H), 2.50-1.88 (m, 7H), 1.78-1.50 (m, 4H).
3-130: δ7.27-7.05 (m, 2H), 6.97-6.86 (m, 1H), 6.10-5.90 (m, 1H), 4.58-4.43 (m, 2H), 4.06-3.94 (m, 1H) , 3.94-3.86 (m, 3H), 3.79-3.72 (m, 3H), 3.50-3.20 (m, 6H), 2.71-2.55 (m, 1H), 2.51-1.91 (m, 7H), 1.86-1.33 ( m, 8H), 1.11-0.77 (m, 6H).
3-131: δ7.72-7.64 (m, 1H), 7.56-7.40 (m, 2H), 7.35-7.07 (m, 4H), 6.96-6.86 (m, 1H), 6.11-5.76 (m, 1H) , 4.58-4.38 (m, 2H), 4.18-3.70 (m, 7H), 3.42-3.28 (m, 6H), 2.54-1.39 (m, 11H).
3-132: δ7.27-7.18 (m, 1H), 7.18-7.04 (m, 1H), 6.97-6.86 (m, 1H), 6.05-5.90 (m, 1H), 4.59-4.41 (m, 2H) , 4.06-3.61 (m, 9H), 3.45-3.25 (m, 6H), 2.70-1.52 (m, 12H), 1.06-0.69 (m, 6H).
3-133: δ7.27-7.19 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.02-5.97 (m, 1H), 4.55-4.47 (m, 2H) , 4.03-3.86 (m, 4H), 3.78-3.70 (m, 3H), 3.39-3.31 (m, 3H), 3.28-3.17 (m, 2H), 3.02-2.92 (m, 3H), 2.52-2.45 ( m, 3H), 2.45-2.10 (m, 4H), 2.07-0.78 (m, 13H).
3-134: δ7.29-7.22 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.04-5.98 (m, 1H), 4.55-4.47 (m, 2H) , 4.04-3.72 (m, 9H), 3.58-3.52 (m, 3H), 3.39-3.31 (m, 3H), 3.03-2.95 (m, 3H), 2.51-2.44 (m, 3H), 2.42-1.89 ( m, 4H), 1.87-1.57 (m, 4H), 1.34-1.07 (m, 9H).
3-135: δ7.25-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.85 (m, 1H), 4.60-4.44 (m, 2H), 4.05-2.97 (m, 16H) , 2.53-1.92 (m, 10H), 1.81-1.55 (m, 4H).
3-136: δ8.15-6.90 (m, 9H), 6.00-5.65 (m, 1H), 4.57-4.38 (m, 2H), 4.05-3.13 (m, 14H), 2.55-2.35 (m, 3H) , 1.82-1.30 (m, 4H).
3-137: δ8.14-6.90 (m, 9H), 5.97-5.62 (m, 1H), 4.58-4.43 (m, 2H), 4.03-2.87 (m, 17H), 2.54-2.37 (m, 3H) , 1.70-1.20 (m, 4H).
3-138: δ7.26-7.18 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.08-5.90 (m, 1H), 4.59-4.42 (m, 2H) , 4.05-3.19 (m, 17H), 2.53-2.42 (m, 3H), 2.41-1.92 (m, 4H), 1.87-1.53 (m, 8H).
3-139: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 5.99-5.93 (m, 1H), 4.56-4.47 (m, 2H) , 4.04-3.94 (m, 1H), 3.93-3.85 (m, 3H), 3.78-3.71 (m, 3H), 3.41-3.33 (m,3H), 3.33-3.21 (m, 4H), 3.21-3.13 ( m, 3H), 2.51-1.91 (m, 7H), 1.79-1.41 (m, 10H).
3-140: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 5.94-5.88 (m, 1H), 4.55-4.47 (m, 2H) , 4.28-4.14 (m, 1H), 4.04-3.92 (m, 1H), 3.92-3.85 (m, 3H), 3.78-3.70 (m, 3H), 3.41-3.33 (m,3H), 3.17-3.08 ( m, 3H), 2.65-2.56 (m, 3H), 2.51-1.91 (m, 7H), 1.78-1.57 (m, 4H), 1.41-0.99 (m, 6H).
4-001: δ7.40-6.80 (m, 3H), 6.09 (s, 1H), 6.02 (s, 1H), 4.30-3.20 (m, 17H), 2.95 (s, 3H), 2.55 (s, 3H) ), 2.10-2.00 (m, 3H), 1.80-1.50 (m, 4H).
4-002: δ7.70-6.85 (m, 6H), 6.09 (s, 1H), 5.81 (s, 1H), 4.25-3.10 (m, 12H), 2.54 (s, 3H), 2.03 (s, 3H) ), 1.85-1.15 (m, 4H).
4-003: δ7.25-7.19 (m, 2H), 7.16-7.07 (m, 1H), 7.07-7.01 (m, 1H), 6.95-6.87 (m, 2H), 6.05-5.87 (m, 1H) , 4.73-4.51 (m, 2H), 3.98-3.82 (m, 4H), 3.71-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.06-2.93 (m, 3H), 2.65-2.51 ( m, 3H), 2.37-2.23 (m, 3H), 1.79-1.44 (m, 4H).
4-004: δ7.25-7.18 (m, 2H), 7.18-7.08 (m, 1H), 7.07-7.00 (m, 1H), 6.95-6.87 (m, 2H), 5.95-5.89 (m, 1H) , 4.72-4.50 (m, 2H), 3.98-3.82 (m, 4H), 3.74-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.05-2.96 (m, 3H), 2.91-2.83 ( m, 3H), 2.66-2.56 (m, 3H), 1.78-1.43 (m, 4H).
4-006: δ7.80-6.80 (m, 6H), 6.00-5.20 (m, 2H), 3.90-3.20 (m, 15H), 2.50-2.40 (m, 3H), 1.80-1.50 (m, 4H) .
4-007: δ7.35-6.80 (m, 6H), 6.00-5.90 (m, 2H), 4.72-4.50 (m, 2H), 4.00-3.20 (m, 12H), 3.10-2.90 (m, 3H) , 2.55-2.40 (m, 3H), 1.85-1.50 (m, 4H).
4-011: δ7.78-7.68 (m, 1H), 7.64-7.55 (m, 1H), 7.50-6.90 (m, 6H), 6.17-6.09 (m, 1H), 4.54-4.41 (m, 2H) , 4.34-4.24 (m, 2H), 4.05-3.93 (m, 1H), 3.75-3.61 (m, 2H), 3.51-3.40 (m, 2H), 3.39-3.25 (m, 2H), 3.03-2.95 ( m, 3H), 2.92-2.83 (m, 3H), 1.84-1.70 (m, 2H), 1.63-1.46 (m, 2H).
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[Test example]
Next, the usefulness of the compound of the present invention as a pest control agent according to one embodiment will be specifically described in the following test examples, but the present invention is not limited thereto. In the test examples, "RH" represents relative humidity, and for example, the description "humidity 100% RH" means that the relative humidity is 100%.
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No. 1H-NMR
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1-001: δ7.26-7.19 (m, 1H), 7.16-7.00 (m, 1H), 6.99-6.85 (m, 1H), 6.10&5.94 (s, 1H), 4.52-4.35 (m, 2H), 4.07-3.86 (m, 6H), 3.76-3.61 (m, 2H), 3.40-3.23 (m, 5H), 2.84&2.82 (s, 3H), 1.81-1.48 (m, 13H)。
1-013: δ7.48-7.35 (m, 2H), 7.35-7.10 (m, 3H), 7.08-6.99 (m, 1H), 6.98-6.85 (m, 1H), 6.12 (s, 1H), 4.74-4.55 (m, 2H), 4.50-4.38 (m, 2H), 4.07-3.93 (m, 3H), 3.73-3.59 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H), 2.83 (s, 3H), 1.81-1.46 (m, 4H)。
1-014: δ7.51-7.39 (m, 2H), 7.25-7.16 (m, 1H), 7.08-6.84 (m, 4H), 5.84 (s, 1H), 4.74-4.57 (m, 2H), 4.49-4.35 (m, 2H), 4.08-3.87 (m, 6H), 3.73-3.56 (m, 2H), 3.39-3.22 (m, 2H), 3.01 (s, 3H), 2.82 (s, 3H), 1.80-1.46 (m, 4H)。
1-016: δ7.47-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.11 (m, 1H), 6.14 (s, 1H), 4.49-4.36 (m, 2H), 4.06-3.96 (m, 3H), 3.90-3.76 (m, 5H), 3.74-3.61 (m, 2H), 3.40-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.85-1.50 (m, 4H)。
1-017: δ7.29-7.37 (m, 2H), 7.19-7.13 (m, 2H), 7.05-6.90 (m, 3H), 5.85 (s, 1H), 4.65-4.49 (m, 2H), 4.45-4.35 (m, 2H), 4.06-3.97 (m, 2H), 3.96-3.86 (m, 4H), 3.75-3.55 (m, 2H), 3.40-3.20 (m, 2H), 3.10 (s, 3H), 2.78 (s, 3H), 1.80-1.45 (m, 4H)。
1-018: δ7.45-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.10 (m, 3H), 7.00-6.92 (m, 1H), 6.13 (s, 1H), 4.64-4.48 (m, 2H), 4.47-4.35 (m, 2H), 4.05-3.95 (m, 3H), 3.76-3.60 (m, 2H), 3.38-3.25 (m, 2H), 3.08 (s, 3H), 2.79 (s, 3H), 1.85-1.50 (m, 4H)。
1-025: δ8.56-8.52 (m, 1H), 8.34-8.29 (m, 1H), 7.50-7.38 (m, 2H), 7.05-6.94 (m, 2H), 5.85 (s, 1H), 4.49-4.35 (m, 2H), 4.08-3.88 (m, 6H), 3.80-3.55 (m, 2H), 3.48 (s, 3H), 3.40-3.20 (m, 2H), 2.77 (s, 3H), 1.80-1.45 (m, 4H)。
1-026: δ8.60-8.55 (m, 1H), 8.35-8.30 (m, 1H), 7.47-7.34 (m, 2H), 7.32-7.24 (m, 1H), 7.21-7.12 (m, 1H), 6.12 (s, 1H), 4.50-4.39 (m, 2H), 4.10-3.95 (m, 3H), 3.82-3.60 (m, 2H), 3.47 (s, 3H), 3.40-3.20 (m, 2H), 2.77 (s, 3H), 1.86-1.43 (m, 4H)。
1-027: δ7.50-7.40 (m, 2H), 7.10-6.95 (m, 2H), 6.91&5.84 (s, 1H), 4.50-4.35 (m, 2H), 4.08-3.75 (m, 8H), 3.73-3.59 (m, 2H), 3.40-3.27 (s, 5H), 2.82 (s, 3H), 2.05-1.45 (m, 5H), 1.02-0.78 (m, 6H)。
1-028: δ7.47-7.35 (m, 2H), 7.32-7.25 (m, 1H), 7.23-7.13 (m, 1H), 6.17&6.11 (s, 1H), 4.50-4.37 (m, 2H), 4.10-3.75 (m, 5H), 3.75-3.61 (m, 2H), 3.40-3.20 (m, 5H), 2.82 (s, 3H), 2.05-1.50 (m, 5H), 1.01-0.78 (m, 6H)。
1-031: δ7.25-7.19 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 5.98 (s, 1H), 4.48-4.35 (m, 2H), 4.06-3.96 (m, 2H), 3.96-3.61 (m, 12H), 3.48-3.30 (m, 2H), 3.28-3.11 (m, 2H), 2.95 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.70-1.48 (m, 4H)。
1-038: δ7.24-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.00&5.92 (s, 1H), 4.50-4.36 (m, 2H), 4.08-3.88 (m, 8H), 3.63 (s, 3H), 3.50-3.12 (m, 7H), 2.81 (s, 3H), 2.05-1.48 (m, 5H), 1.01-0.77 (m, 6H)。
1-042: δ7.61-7.55 (m, 2H), 7.48-7.41 (m, 3H), 6.08 (s, 1H), 4.47-4.38 (m, 2H), 4.10-3.96 (m, 3H), 3.91-3.77 (m, 2H), 3.80 (s, 3H), 3.71-3.60 (m, 2H), 3.39-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.05 (s, 3H), 1.82-1.50 (m, 4H)。
1-046: δ7.62-7.55 (m, 2H), 7.50-7.40 (m, 3H), 6.06 (s, 1H), 4.49-4.34 (m, 2H), 4.08-3.97 (m, 3H), 3.91-3.76 (m, 2H), 3.79 (s, 3H), 3.63 (s, 3H), 3.49-3.33 (m, 2H), 3.25-3.09 (m, 2H), 2.95 (s, 3H), 2.83 (s, 3H), 2.05 (s, 3H), 1.77-1.47 (m, 4H)。
1-047: δ7.60-7.54 (m, 2H), 7.49-7.41 (m, 3H), 6.28-6.21 (m, 1H), 6.10-5.99 (m, 1H), 6.03 (s, 1H), 4.48-4.39 (m, 2H), 4.09-3.82 (m, 4H), 3.73-3.65 (m, 1H), 3.62 (s, 3H), 3.52-3.38 (m, 2H), 3.20-3.05 (m, 2H), 2.97 (s, 3H), 2.82 (s, 3H), 1.77-1.45 (m, 4H)。
1-059: δ8.60-8.50 (m, 1H), 8.35-8.30 (m, 1H), 7.60-7.52 (m, 1H), 7.50-7.34 (m, 3H), 6.11 (s, 1H), 4.50-4.37 (m, 2H), 4.10-3.89 (m, 3H), 3.80-3.60 (m, 2H), 3.46 (s, 3H), 3.40-3.15 (m, 2H), 2.77 (s, 3H), 1.90-1.40 (m, 4H)。
1-063: δ7.25-7.20 (m, 1H), 7.18-7.09 (m, 1H), 6.96-6.89 (m, 1H), 6.08&5.98 (s, 1H), 4.50-4.38 (m, 2H), 4.20-3.88 (m, 8H), 3.73-3.60 (m, 2H), 3.38-3.29 (m, 5H), 2.83&2.82 (s, 3H), 1.80-1.50 (m, 6H), 1.03-0.80 (m, 3H)。
1-064: δ7.60-7.58 (m, 1H), 7.50-7.36 (m, 3H), 7.24-7.20 (m, 1H), 7.06-7.03 (m, 1H), 6.95-6.90 (m, 1H), 6.11 (s, 1H), 4.72-4.57 (m, 2H), 4.47-4.39 (m, 2H), 4.08-3.92 (m, 3H), 3.71-3.59 (m, 2H), 3.38-3.24 (m, 2H), 3.01 (s, 3H), 2.83 (s, 3H), 1.80-1.45 (m, 4H)。
1-065: δ7.62-7.57 (m, 1H), 7.52-7.37 (m, 3H), 6.30-6.24 (m, 1H), 6.15-5.94 (m, 2H), 4.49-4.40 (m, 2H), 4.06-3.84 (m, 5H), 3.72-3.62 (m, 2H), 3.38-3.29 (m, 2H), 2.98 (s, 3H), 2.83 (s, 3H), 1.80-1.50 (m, 4H)。
1-066: δ7.76-7.68 (m, 1H), 7.62-7.58 (m, 1H), 7.52-7.30 (m, 3H), 7.25-7.19 (m, 1H), 7.16-6.95 (m, 2H), 6.13 (s, 1H), 4.54-4.38 (m, 4H), 4.06-3.90 (m, 3H), 3.70-3.60 (m, 2H), 3.39-3.25 (m, 2H), 2.99 (s, 3H), 2.88&2.83 (s, 3H), 1.80-1.50 (m, 4H)。
1-067: δ7.24-7.03 (m, 2H), 6.95-6.70 (m, 1H), 6.05 & 5.90 (s, 1H), 4.49-4.36 (m, 2H), 4.10-3.95 (m, 2H), 3.90 & 3.89 (s, 3H), 3.85-3.72 (m, 1H), 3.30 & 3.25 (s, 3H), 2.84 & 2.82 (s, 3H), 2.75-2.51 (m, 2H), 2.40-2.20 (m, 2H), 2.06-1.66 (m, 4H), 1.53 & 1.41 (s, 9H)。
1-068: δ7.29-7.20 (m, 1H), 7.16-7.06 (m, 1H), 6.94-6.84 (m, 1H), 6.17-5.81 (m, 1H), 4.73-4.61 (m, 1H), 4.47-4.34 (m, 2H), 4.08-3.97 (m, 2H), 3.92-3.84 (m, 3H), 3.38-3.22 (m, 6H), 3.05-2.97 (m, 3H), 2.86-2.77 (m, 3H), 1.56-1.17 (m, 12H)。
1-069: δ7.59-7.38 (m, 1H), 7.17-7.05 (m, 1H), 6.94-6.85 (m, 1H), 6.29-5.88 (m, 1H), 4.47-4.32 (m, 3H), 4.07-3.96 (m, 2H), 3.93-3.87 (m, 3H), 3.40-3.04 (m, 5H), 2.86-2.71 (m, 6H), 2.20-2.00 (m, 2H), 1.57-1.34 (m, 9H)。
1-070: δ7.27-7.20 (m, 1H), 7.16-7.03 (m, 1H), 6.96-6.86 (m, 1H), 6.09 & 5.94 (s, 1H), 4.49-4.36 (m, 2H), 4.10-3.96 (m, 2H), 3.90 & 3.89 (s, 3H), 3.74-3.62 (m, 1H), 3.29 & 3.24 (s, 3H), 2.84 & 2.82 (s, 3H), 1.74-1.01 (m, 19H)。
1-071: δ7.28-7.18 (m, 1H), 7.16-7.04 (m, 1H), 6.94-6.86 (m, 1H), 6.10-5.89 (m, 1H), 4.48-4.37 (m, 2H), 4.08-3.98 (m, 2H), 3.92-3.86 (m, 3H), 3.82-3.68 (m, 1H), 3.30-3.06 (m, 7H), 2.85-2.78 (m, 3H), 1.86-1.13 (m, 17H)。
1-072: δ7.30-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.16-5.87 (m, 1H), 4.50-4.37 (m, 3H), 4.09-3.94 (m, 2H), 3.94-3.86 (m, 3H), 3.73-3.33 (m, 4H), 3.30-3.21 (m, 3H), 2.86-2.79 (m, 3H), 2.14-1.97 (m, 3H), 1.67-1.19 (m, 13H)。
1-073: δ7.27-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.17-5.82 (m, 1H), 4.48-4.37 (m, 2H), 4.09-3.94 (m, 3H), 3.93-3.87 (m, 3H), 3.58-3.08 (m, 7H), 2.85-2.77 (m, 3H), 2.34-2.18 (m, 2H), 1.72-1.34 (m, 13H), 1.13-1.03 (m, 3H)。
1-078: δ7.50-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.95-6.87 (m, 1H), 5.97-5.85 (m, 1H), 4.49-4.36 (m, 2H), 4.09-3.94 (m, 3H), 3.93-3.88 (m, 3H), 3.77-3.73 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.78 (m, 3H), 2.43-2.15 (m, 4H), 1.82-1.34 (m, 13H)。
1-079: δ7.48-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.94-6.88 (m, 1H), 5.97 & 5.86 (s, 1H), 4.50-4.37 (m, 2H), 4.09-3.87 (m, 3H), 3.91 & 3.90 (s, 3H), 3.62 (s, 3H), 3.50-3.11 (m, 4H), 3.28 & 3.23 (s, 3H), 2.85-2.78 (m, 3H), 1.72-1.23 (m, 13H)。
1-086: δ7.28-7.07 (m, 2H), 6.98-6.84 (m, 1H), 6.09-5.88 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.22 (m, 12H), 2.89-2.77 (m, 3H), 2.71-1.95 (m, 5H), 1.91-1.36 (m, 4H), 1.10-0.76 (m, 10H)。
1-089: δ7.28-7.20 (m, 1H), 7.18-7.07 (m, 1H), 6.97-6.87 (m, 1H), 6.05-5.90 (m, 1H), 4.50-4.36 (m, 2H), 4.10-3.94 (m, 5H), 3.93-3.88 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.79 (m, 3H), 2.46-1.93 (m, 4H), 1.79-1.62 (m, 4H), 1.55-1.36 (m, 9H), 1.22-1.14 (m, 3H)。
1-090: δ7.41-7.28 (m, 1H), 7.28-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.04-5.89 (m, 1H), 4.49-4.36 (m, 2H), 4.10-3.96 (m, 3H), 3.93-3.86 (m, 3H), 3.29-3.19 (m, 3H), 2.85-2.78 (m, 3H), 2.48-1.95 (m, 4H), 1.82-1.61 (m, 4H), 1.54-1.35 (m, 9H)。
1-091: δ7.25-7.03 (m, 2H), 6.98-6.81 (m, 1H), 6.10-5.87 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.87 (m, 6H), 3.62-3.56 (m, 3H), 3.32-3.22 (m, 3H), 2.86-2.79 (m, 3H), 2.28-1.17 (m, 18H)。
1-092: δ7.33-7.20 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 5.98 (s, 1H), 4.52-4.37 (m, 4H), 4.07-3.95 (m, 3H), 3.93-3.72 (m, 8H), 2.96-2.90 (m, 3H), 2.83-2.79 (m, 3H), 2.40-1.87 (m, 10H), 1.79-1.59 (m, 4H)。
1-093: δ7.28-7.20 (m, 1H), 7.15-7.03 (m, 1H), 6.95-6.86 (m, 1H), 6.19-5.89 (m, 1H), 4.50-4.35 (m, 3H), 4.09-3.94 (m, 4H), 3.93-3.81 (m, 3H), 3.80-3.71 (m, 3H), 3.70-3.59 (m, 1H), 3.04-2.93 (m, 3H), 2.84-2.69 (m, 3H), 2.47-1.94 (m, 7H), 1.79-1.56 (m, 4H)。
1-094: δ7.29-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.87 (m, 1H), 4.49-4.35 (m, 2H), 4.17-3.84 (m, 8H), 3.56-3.03 (m, 7H), 2.84-2.76 (m, 3H), 1.76-1.14 (m, 16H)。
1-096: δ7.29-7.08 (m, 2H), 6.96-6.86 (m, 1H), 5.96 (s, 1H), 4.49-4.39 (m, 2H), 4.09-3.98 (m, 3H), 3.90 (s, 3H), 3.41-2.73 (m, 10H), 2.68 (s, 3H), 1.88-1.65 (m, 4H), 1.57-1.49 (m, 9H)。
1-100: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.02-5.91 (m, 1H), 4.49-4.38 (m, 2H), 4.17-3.94 (m, 4H), 3.92-3.87 (m, 3H), 3.79-3.69 (m, 4H), 3.35-3.26 (m, 3H), 2.81 (s, 3H), 2.42-1.93 (m, 4H), 1.89-1.53 (m, 4H), 1.01-0.74 (m, 7H)。
1-102: δ7.56-7.49 (m, 2H), 7.36-7.19 (m, 4H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.01-5.96 (m, 1H), 4.49-4.35 (m, 4H), 4.07-3.89 (m, 3H), 3.91 (s, 3H), 3.75-3.71 (m, 3H), 2.92 (s, 3H), 2.83 (s, 3H), 2.40-1.91 (m, 4H), 1.76-1.51 (m, 4H)。
1-105: δ7.28-7.19 (m, 1H), 7.17-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.00-5.96 (m, 1H), 4.47-4.38 (m, 2H), 4.07-3.70 (m, 14H), 2.96-2.91 (m, 3H), 2.84-2.81 (m, 3H), 2.52-1.59 (m, 11H)。
1-106: δ7.28-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.29-6.20 (m, 1H), 6.10-5.93 (m, 2H), 4.48-4.37 (m, 2H), 4.07-3.81 (m, 5H), 3.91 (s, 3H), 3.75 (s, 3H), 2.96 (s, 3H), 2.81 (s, 3H), 2.39-1.94 (m, 4H), 1.78-1.60 (m, 4H)。
1-107: δ7.78-7.68 (m, 1H), 7.28-6.86 (m, 6H), 6.00-5.94 (m, 1H), 4.55-4.36 (m, 4H), 4.08-3.86 (m, 3H), 3.91 (s, 3H), 3.76-3.71 (m, 3H), 2.96 (s, 3H), 2.82 (s, 3H), 2.38-1.92 (m, 4H), 1.76-1.53 (m, 4H)。
1-108: δ7.29-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.04-5.85 (m, 1H), 4.50-4.39 (m, 2H), 4.18-3.94 (m, 3H), 3.94-3.87 (m, 3H), 3.81-3.71 (m, 3H), 3.60-3.47 (m, 3H), 3.38-3.33 (m, 3H), 2.84-2.79 (m, 3H), 2.52-1.91 (m, 7H), 1.84-1.54 (m, 4H)。
1-109: δ7.25-7.08 (m, 2H), 7.04-6.88 (m, 1H), 6.07-5.88 (m, 1H), 4.49-4.39 (m, 2H), 4.08-3.88 (m, 6H), 3.32-2.94 (m, 7H), 2.85-2.80 (m, 3H), 2.71 (s, 6H), 1.81-1.38 (m, 13H)。
2-003: δ7.24-7.15 (m, 1H), 7.15-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.93 (s, 1H), 3.98-3.87 (m, 4H), 3.78-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.54&2.53 (s, 3H), 2.12&2.11 (s, 3H), 1.80-1.35 (m, 13H)。
2-004: δ7.24-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.94 (s, 1H), 3.98-3.87 (m, 4H), 3.75-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.53&2.51 (s, 3H), 1.82-1.35 (m, 14H), 1.00-0.80 (m, 4H)。
2-005: δ7.60-7.49 (m, 2H), 7.40-7.05 (m, 5H), 6.95-6.83 (m, 1H), 6.08-5.98 (m, 1H), 4.50-4.37 (m, 2H), 3.98-3.84 (m, 4H), 3.70-3.51 (m, 2H), 3.39-3.22 (m, 2H), 3.00-2.89 (m, 3H), 2.54 (s, 3H), 2.11 (s, 3H), 1.75-1.42 (m, 4H)。
2-006: δ7.78-7.70 (m, 1H), 7.27-7.05 (m, 4H), 7.03-6.85 (m, 2H), 6.01 (s, 1H), 4.55-4.40 (m, 2H), 4.00-3.85 (m, 4H), 3.69-3.50 (m, 2H), 3.39-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.79-1.45 (m, 4H)。
2-007: δ7.59-7.49 (m, 2H), 7.38-7.09 (m, 5H), 6.95-6.88 (m, 1H), 5.99 (s, 1H), 4.49-4.35 (m, 2H), 3.95-3.83 (m, 4H), 3.70-3.52 (m, 2H), 3.48 (s, 1H), 3.39-3.21 (m, 2H), 2.94 (s, 3H), 2.59 (s, 3H), 1.88-1.42 (m, 4H)。
2-008: δ7.70-7.62 (m, 1H), 7.57-7.10 (m, 6H), 6.98-6.84 (m, 1H), 6.11&5.77 (s, 1H), 4.05-3.78 (m, 4H), 3.75-3.51 (m, 2H), 3.51&3.48 (s, 1H), 3.41-3.12 (m, 5H), 2.61&2.53 (s, 3H), 1.82-1.18 (m, 4H)。
2-011: δ7.70-7.59 (m, 1H), 7.52-7.42 (m, 1H), 7.29-7.07 (m, 2H), 6.95-6.86 (m, 1H), 6.10-5.92 (m, 1H), 4.04-3.83 (m, 4H), 3.80-3.55 (m, 2H), 3.49 (s, 3H), 3.44-3.18 (m, 2H), 2.58-2.45 (m, 3H), 2.13 (s, 3H), 1.82-1.37 (m, 4H)。
2-012: δ7.29-7.05 (m, 2H), 6.95-6.85 (m, 1H), 6.07-5.94 (m, 1H), 3.96-3.75 (m, 9H), 3.72-3.53 (m, 2H), 3.41-3.28 (m, 2H), 3.00-2.89 (m, 3H), 2.64-2.46 (m, 3H), 2.16-2.11 (m, 3H), 2.09-2.00 (m, 3H), 1.78-1.49 (m, 4H)。
2-013: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.91 (m, 1H), 4.06-3.72 (m, 6H), 3.71-3.58 (m, 2H), 3.41-3.26 (m, 5H), 2.55-2.45 (m, 3H), 2.17-2.06 (m, 3H), 2.05-1.80 (m, 1H), 1.76-1.45 (m, 4H), 1.07-0.70 (m, 6H)。
2-014: δ7.71-7.41 (m, 3H), 7.38-7.09 (m, 4H), 6.98-6.85 (m, 1H), 6.12&5.78 (s, 1H), 4.02-3.79 (m, 4H), 3.76-3.53 (m, 2H), 3.43-3.15 (m, 5H), 2.56&2.47 (s, 3H), 2.12&2.10 (s, 3H), 1.82-1.31 (m, 4H)。
2-015: δ7.71-7.54 (m, 1H), 7.41-7.35 (m, 1H), 7.27-7.07 (m, 2H), 7.04-6.97 (m, 1H), 6.95-6.85 (m, 1H), 5.84 (s, 1H), 4.00-3.80 (m, 4H), 3.78-3.59 (m, 2H), 3.41 (s, 3H), 3.32-3.15 (m, 2H), 2.59-2.47 (m, 3H), 2.13 (s, 3H), 1.80-1.30 (m, 4H)。
2-016: δ7.71-6.90 (m, 3H), 6.02 (s, 1H), 5.55 (br, 1H), 4.00-3.80 (m, 4H), 3.69-3.56 (m, 2H), 3.50 (s, 1H), 3.39-3.25 (m, 2H), 2.80 (s, 3H), 2.61 (s, 3H), 1.79-1.45 (m, 4H)。
2-018: δ7.25-7.09 (m, 2H), 6.97-6.89 (m, 1H), 6.06-5.94 (m, 1H), 3.99-3.85 (m, 4H), 3.76-3.60 (m, 2H), 3.41-3.23 (m, 5H), 2.57-2.34 (m, 6H), 2.12 (s, 3H), 1.78-1.50 (m, 4H)。
2-019: δ7.29-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.94-6.87 (m, 2H), 5.99 (s, 1H), 4.70-4.53 (m, 2H), 3.98-3.80 (m, 4H), 3.70-3.50 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.77-1.42 (m, 4H)。
2-020: δ7.25-7.09 (m, 2H), 6.98-6.89 (m, 1H), 6.30-5.94 (m, 3H), 4.01-3.82 (m, 6H), 3.71-3.58 (m, 2H), 3.40-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.12 (s, 3H), 1.78-1.44 (m, 4H)。
2-022: δ8.85-8.54 (m, 1H), 8.32-8.25 (m, 1H), 7.24-7.08 (m, 2H), 6.96-6.89 (m, 1H), 6.12-5.97 (m, 1H), 3.99-3.84 (m, 1H), 3.90 (s, 3H), 3.80-3.58 (m, 2H), 3.47 (s, 3H), 3.43-3.21 (m, 2H), 2.57-2.45 (m, 3H), 2.12 (s, 3H), 1.83-1.42 (m, 4H)。
3-001: δ7.28-7.18 (m, 2H), 7.16-6.99 (m, 2H), 6.96-6.85 (m, 2H), 6.04-5.88 (m, 1H), 4.74-4.55 (m, 2H), 4.50 (s, 2H), 3.98-3.80 (m, 4H), 3.74-3.51 (m, 2H), 3.40-3.18 (m, 5H), 3.00 (s, 3H), 2.48 (s, 3H), 1.80-1.44 (m, 4H)。
3-002: δ7.70-7.62 (m, 1H), 7.41-7.34 (m, 1H), 7.23-7.05 (m, 2H), 7.04-6.86 (m, 2H), 6.15-5.81 (m, 1H), 4.63-4.42 (m, 2H), 4.05-3.80 (m, 4H), 3.79-3.55 (m, 2H), 3.50-3.10 (m, 8H), 2.55-2.37 (m, 3H), 1.82-1.12 (m, 4H)。
3-003:δ8.86-8.51 (m, 1H), 8.33-8.23 (m, 1H), 7.28-7.04 (m, 2H), 6.97-6.85 (m, 1H), 6.16-5.90 (m, 1H), 4.60-4.44 (m, 2H), 4.02-3.80 (m, 4H), 3.80-3.54 (m, 2H), 3.50-3.10 (m, 8H), 2.51-2.37 (m, 3H), 1.85-1.39 (m, 4H)。
3-004: δ7.28-7.18 (m, 2H), 7.17-7.07 (m, 1H), 7.03-6.88 (m, 2H), 6.13-6.06 (m, 1H), 4.58-4.47 (m, 2H), 4.55-3.83 (m, 4H), 3.80-3.62 (m, 2H), 3.45-3.27 (m, 7H), 2.51-2.43 (m, 3H), 1.82-1.21 (m, 13H)。
3-005: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.11-5.95 (m, 1H), 4.60-4.44 (m, 2H), 4.05-3.75 (m, 6H), 3.75-3.57 (m, 2H), 3.43-3.24 (m, 8H), 2.52-2.42 (m, 3H), 2.08-1.80 (m, 1H), 1.80-1.47 (m, 4H), 1.04-0.76 (m, 6H)。
3-006: δ7.28-7.21 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.13-5.88 (m, 1H), 4.59-4.46 (m, 2H), 4.02-3.76 (m, 9H), 3.76-3.57 (m, 2H), 3.42-3.26 (m, 5H), 3.01-2.92 (m, 3H), 2.53-2.45 (m, 3H), 2.10-2.02 (m, 3H), 1.83-1.47 (m, 4H)。
3-007: δ7.28-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.30-6.21 (m, 1H), 6.12-5.99 (m, 2H), 4.54-4.49 (m, 2H), 3.98-3.83 (m, 6H), 3.73-3.57 (m, 2H), 3.40-3.26 (m, 5H), 3.03-2.92 (m, 3H), 2.53-2.43 (m, 3H), 1.83-1.46 (m, 4H)。
3-008: δ7.23-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.87 (m, 1H), 4.63-4.46 (m, 2H), 4.06-3.86 (m, 4H), 3.79-3.51 (m, 5H), 3.42-3.21 (m, 8H), 2.52-2.41 (m, 3H), 2.12-1.96 (m, 3H), 1.82-1.44 (m, 4H)。
3-009: δ7.82-7.72 (m, 1H), 7.29-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.07-5.92 (m, 1H), 4.58-4.40 (m, 4H), 3.97-3.83 (m, 4H), 3.72-3.55 (m, 2H), 3.40-3.23 (m, 5H), 3.03-2.94 (m, 3H), 2.53-2.44 (m, 3H), 1.79-1.44 (m, 4H)。
3-010: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.12-5.93 (m, 1H), 4.59-4.45 (m, 2H), 4.03-3.83 (m, 6H), 3.74-3.60 (m, 2H), 3.44-3.23 (m, 8H), 2.51-2.43 (m, 3H), 1.83-1.44 (m, 4H), 1.04-0.75 (m, 9H)。
3-014: δ8.13-7.23 (m, 5H), 7.23-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.23-5.75 (m, 1H), 4.63-4.39 (m, 2H), 4.04-3.79 (m, 4H), 3.77-3.54 (m, 2H), 3.47-3.15 (m, 8H), 2.55-2.36 (m, 3H), 1.86-1.31 (m, 4H)。
3-015: δ8.15-7.81 (m, 1H), 7.24-7.17 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.86 (m, 1H), 6.12-5.91 (m, 1H), 4.57-4.41 (m, 2H), 3.99-3.81 (m, 4H), 3.79-3.54 (m, 2H), 3.50-3.20 (m, 8H), 2.50-2.40 (m, 3H), 1.83-1.40 (m, 4H)。
3-016: δ8.17-8.07 (m, 1H), 7.23-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.16-5.84 (m, 1H), 4.57-4.43 (m, 2H), 4.00-3.84 (m, 4H), 3.79-3.53 (m, 2H), 3.51-3.21 (m, 8H), 2.53-2.39 (m, 3H), 1.82-0.98 (m, 13H)。
3-017: δ7.51-7.45 (m, 1H), 7.23-7.06 (m, 2H), 6.95-6.86 (m, 1H), 6.69-6.62 (m, 1H), 6.15-5.83 (m, 1H), 4.62-4.43 (m, 2H), 4.04-3.78 (m, 4H), 3.78-3.56 (m, 2H), 3.46-3.11 (m, 8H), 2.56-2.35 (m, 6H), 1.81-1.29 (m, 4H)。
3-018: δ7.50-7.42 (m, 1H), 7.22-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.88-6.81 (m, 1H), 6.13-5.79 (m, 1H), 4.60-4.46 (m, 2H), 4.03-3.82 (m, 4H), 3.80-3.56 (m, 2H), 3.49-3.12 (m, 8H), 2.54-2.42 (m, 3H), 1.83-1.34 (m, 4H)。
3-019: δ7.27-7.05 (m, 2H), 6.96-6.87 (m, 1H), 6.14-5.89 (m, 1H), 4.57-4.46 (m, 2H), 3.98-3.86 (m, 4H), 3.77-3.60 (m, 2H), 3.48-3.17 (m, 8H), 2.72-2.08 (m, 4H), 2.06-1.01 (m, 14H)。
3-020: δ7.27-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.14-5.88 (m, 1H), 4.60-4.45 (m, 2H), 4.00-3.86 (m, 4H), 3.76-3.60 (m, 2H), 3.50-3.21 (m, 8H), 3.14-2.52 (m, 1H), 2.52-2.41 (m, 3H), 2.08-1.36 (m, 12H)。
3-021: δ7.28-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.18-5.92 (m, 1H), 4.59-4.44 (m, 2H), 4.04-3.84 (m, 4H), 3.77-3.60 (m, 2H), 3.52-3.21 (m, 8H), 2.74-2.06 (m, 4H), 1.88-1.36 (m, 8H), 1.10-0.77 (m, 6H)。
3-022: δ7.26-7.18 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 6.15-5.86 (m, 2H), 4.58-4.41 (m, 2H), 4.10-4.01 (m, 1H), 3.99-2.98 (m, 15H), 2.53-2.43 (m, 3H), 1.81-1.41 (m, 4H)。
3-023: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.12-5.95 (m, 1H), 4.86-4.62 (m, 1H), 4.60-4.45 (m, 2H), 4.07-3.22 (m, 14H), 2.54-2.42 (m, 3H), 2.00-1.10 (m, 14H)。
3-024: δ7.27-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.95-6.87 (m, 2H), 6.07-5.89 (m, 1H), 4.73-4.49 (m, 4H), 3.97-3.80 (m, 4H), 3.72-3.45 (m, 4H), 3.39-3.21 (m, 2H), 3.07-2.92 (m, 3H), 2.55-2.39 (m, 3H), 1.78-1.42 (m, 4H), 1.30-1.13 (m, 3H)。
3-025: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.10-5.94 (m, 1H), 4.65-4.49 (m, 2H), 4.05-3.46 (m, 10H), 3.42-3.25 (m, 5H), 2.51-2.42 (m, 3H), 2.07-1.81 (m, 1H), 1.80-1.47 (m, 4H), 1.30-1.17 (m, 3H), 1.02-0.75 (m, 6H)。
3-026: δ7.68-7.61 (m, 1H), 7.36-7.30 (m, 1H), 7.21-7.08 (m, 2H), 6.98-6.87 (m, 2H), 6.11-5.72 (m, 1H), 4.62-4.45 (m, 2H), 3.99-3.76 (m, 4H), 3.76-3.19 (m, 11H), 3.11-2.77 (m, 2H), 2.53-2.42 (m, 3H), 1.73-1.18 (m, 4H)。
3-027: δ7.73-7.64 (m, 1H), 7.52-6.81 (m, 5H), 5.76-5.25 (m, 1H), 4.63-4.47 (m, 2H), 4.34-4.07 (m, 1H), 3.90-3.79 (m, 4H), 3.54-3.32 (m, 6H), 2.87-2.45 (m, 6H), 1.33-1.10 (m, 3H)。
3-028: δ7.40-6.74 (m, 5H), 6.14-5.78 (m, 1H), 4.63-4.43 (m, 2H), 4.03-2.89 (m, 17H), 2.57-2.39 (m, 6H), 1.72-1.21 (m, 4H)。
3-029: δ8.87-7.90 (m, 2H), 7.25-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.11-5.88 (m, 1H), 4.61-4.44 (m, 2H), 4.01-2.98 (m, 17H), 2.55-2.39 (m, 3H), 1.75-1.16 (m, 4H)。
3-030: δ8.90-7.26 (m, 3H), 7.19-7.02 (m, 2H), 6.92-6.82 (m, 1H), 5.69-5.29 (m, 1H), 4.61-4.44 (m, 2H), 4.35-4.16 (m, 1H), 3.93-3.76 (m, 3H), 3.54-3.31 (m, 6H), 2.87-2.30 (m, 6H), 1.39-1.16 (m, 3H)。
3-031: δ8.12-7.07 (m, 7H), 6.96-6.86 (m, 1H), 6.13-5.75 (m, 1H), 4.61-4.38 (m, 2H), 4.04-2.91 (m, 17H), 2.54-2.35 (m, 3H), 1.72-1.21 (m, 4H)。
3-032: δ7.25-7.17 (m, 2H), 7.15-7.06 (m, 1H), 7.05-6.99 (m, 1H), 6.94-6.84 (m, 2H), 6.06-5.87 (m, 1H), 4.74-4.41 (m, 4H), 3.97-3.82 (m, 4H), 3.69-3.55 (m, 3H), 3.45-3.07 (m, 7H), 3.04-2.95 (m, 3H), 2.53-2.41 (m, 3H), 1.72-1.41 (m, 4H)。
3-034: δ7.25-7.17 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.28-6.19 (m, 1H), 6.11-5.95 (m, 2H), 4.65-4.43 (m, 2H), 4.00-3.81 (m, 6H), 3.65-3.55 (m, 3H), 3.50-3.10 (m, 7H), 3.00-2.92 (m, 3H), 2.53-2.43 (m, 3H), 1.73-1.44 (m, 4H)。
3-035: δ7.85-7.47 (m, 1H), 7.22-7.02 (m, 2H), 6.93-6.83 (m, 1H), 6.45-5.94 (m, 2H), 5.59-5.44 (m, 1H), 4.57-4.45 (m, 2H), 4.35-4.22 (m, 1H), 4.06-3.78 (m, 5H), 3.45-3.33 (m, 3H), 3.10-2.95 (m, 3H), 2.95-2.78 (m, 3H), 2.55-2.39 (m, 3H), 1.41-1.30 (m, 3H)。
3-036: δ7.80-7.71 (m, 1H), 7.27-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.09-5.88 (m, 1H), 4.59-4.39 (m, 4H), 3.99-3.82 (m, 4H), 3.66-3.56 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.94 (m, 3H), 2.53-2.43 (m, 3H), 1.71-1.43 (m, 4H)。
3-037: δ7.24-7.06 (m, 2H), 6.95-6.87 (m, 1H), 6.05-5.92 (m, 1H), 4.59-4.43 (m, 2H), 4.06-3.86 (m, 6H), 3.81-3.15 (m, 13H), 2.54-2.41 (m, 3H), 2.12-1.75 (m, 1H), 1.74-1.46 (m, 4H), 1.07-0.73 (m, 6H)。
3-038: δ7.79-7.47 (m, 1H), 7.25-7.01 (m, 2H), 6.92-6.82 (m, 1H), 5.67-5.46 (m, 1H), 4.62-4.45 (m, 2H), 4.35-4.21 (m, 1H), 4.06-3.69 (m, 5H), 3.48-3.25 (m, 6H), 2.90-2.73 (m, 3H), 2.55-2.37 (m, 3H), 2.14-1.74 (m, 1H), 1.40-0.73 (m, 9H)。
3-039: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.07-5.90 (m, 1H), 4.60-4.40 (m, 2H), 4.00-3.76 (m, 9H), 3.66-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.00-2.89 (m, 3H), 2.56-2.44 (m, 3H), 2.09-2.01 (m, 3H), 1.71-1.47 (m, 4H)。
3-041: δ7.25-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.07-5.84 (m, 1H), 4.62-4.40 (m, 2H), 4.04-3.83 (m, 4H), 3.73-2.92 (m, 16H), 2.52-2.43 (m, 3H), 2.12-1.95 (m, 3H), 1.78-1.39 (m, 4H)。
3-042: δ7.76-7.52 (m, 1H), 7.22-7.00 (m, 2H), 6.92-6.83 (m, 1H), 5.72-5.25 (m, 1H), 4.62-4.45 (m, 2H), 4.35-4.21 (m, 1H), 4.07-3.27 (m, 12H), 2.86-2.74 (m, 3H), 2.53-2.39 (m, 3H), 2.14-1.92 (m, 3H), 1.41-1.21 (m, 3H)。
3-043: δ7.25-7.07 (m, 2H), 7.02-6.87 (m, 2H), 6.10-5.93 (m, 1H), 4.58-4.41 (m, 2H), 4.04-3.11 (m, 17H), 2.51-2.39 (m, 3H), 1.72-1.49 (m, 4H), 1.33-1.18 (m, 9H)。
3-044: δ7.61-7.39 (m, 5H), 6.12-6.02 (m, 1H), 4.59-4.44 (m, 2H), 4.10-3.93 (m, 3H), 3.85-3.57 (m, 3H), 3.56-3.07 (m, 10H), 2.55-2.39 (m, 3H), 2.10-1.78 (m, 1H), 1.77-1.46 (m, 4H), 1.06-0.75 (m, 6H)。
3-045: δ7.58-7.35 (m, 5H), 5.49-5.23 (m, 1H), 4.64-4.43 (m, 2H), 4.20-3.65 (m, 3H), 3.45-3.16 (m, 6H), 2.98-2.70 (m, 3H), 2.54-2.37 (m, 3H), 2.11-1.75 (m, 1H), 1.66-1.37 (m, 3H), 1.31-0.71 (m, 6H)。
※NHに由来するプロトンは観測されなかった。
3-046: δ7.62-7.54 (m, 2H), 7.50-7.38 (m, 3H), 6.14-6.04 (m, 1H), 4.60-4.44 (m, 2H), 4.12-3.75 (m, 3H), 3.74-3.59 (m, 2H), 3.44-3.24 (m, 8H), 2.56-2.41 (m, 3H), 2.08-1.48 (m, 5H), 1.06-0.76 (m, 6H)。
3-047: δ7.64-7.54 (m, 2H), 7.49-7.38 (m, 3H), 6.17-6.02 (m, 1H), 4.62-4.41 (m, 2H), 4.08-3.95 (m, 1H), 3.93-3.75 (m, 5H), 3.66-3.58 (m, 3H), 3.50-3.28 (m, 5H), 3.27-3.10 (m, 2H), 3.00-2.87 (m, 3H), 2.55-2.40 (m, 3H), 2.14-1.98 (m, 3H), 1.78-1.49 (m, 4H)。
3-049: δ7.62-7.55 (m, 2H), 7.48-7.38 (m, 3H), 6.17-6.04 (m, 1H), 4.58-4.43 (m, 2H), 4.08-3.95 (m, 1H), 3.92-3.72 (m, 5H), 3.72-3.58 (m, 2H), 3.39-3.26 (m, 5H), 3.02-2.88 (m, 3H), 2.51-2.45 (m, 3H), 2.09-2.01 (m, 3H), 1.85-1.49 (m, 4H)。
3-050: δ7.61-7.54 (m, 2H), 7.49-7.41 (m, 3H), 7.23-7.18 (m, 1H), 7.05-7.01 (m, 1H), 6.92-6.86 (m, 1H), 6.13-6.01 (m, 1H), 4.73-4.55 (m, 2H), 4.55-4.43 (m, 2H), 4.04-3.93 (m, 1H), 3.70-3.56 (m, 3H), 3.51-3.32 (m, 5H), 3.25-3.04 (m, 2H), 3.03-2.96 (m, 3H), 2.54-2.42 (m, 3H), 1.75-1.42 (m, 4H)。
3-051: δ7.56-7.36 (m, 5H), 7.29-7.16 (m, 1H), 7.02-6.79 (m, 2H), 5.47-5.22 (m, 1H), 4.94-4.67 (m, 1H), 4.57-3.71 (m, 4H), 3.44-3.25 (m, 3H), 3.14-2.72 (m, 6H), 2.52-2.35 (m, 3H), 1.48-0.72 (m, 3H)。
※NHに由来するプロトンは観測されなかった。
3-052: δ7.62-7.55 (m, 2H), 7.48-7.41 (m, 3H), 7.24-7.19 (m, 1H), 7.06-7.01 (m, 1H), 6.93-6.87 (m, 1H), 6.10-6.06 (m, 1H), 4.73-4.55 (m, 2H), 4.51-4.46 (m, 2H), 4.07-3.93 (m, 1H), 3.72-3.56 (m, 2H), 3.39-3.20 (m, 5H), 3.04-2.96 (m, 3H), 2.52-2.45 (m, 3H), 1.82-1.45 (m, 4H)。
3-054: δ7.58-7.38 (m, 5H), 6.34-6.13 (m, 1H), 6.08-5.92 (m, 1H), 5.48-5.22 (m, 1H), 4.64-3.70 (m, 6H), 3.43-3.28 (m, 3H), 3.02-2.74 (m, 6H), 2.54-2.39 (m, 3H), 1.48-0.97 (m, 3H)。
3-055: δ7.68-7.38 (m, 5H), 6.33-5.98 (m, 3H), 4.60-4.43 (m, 2H), 4.19-3.83 (m, 3H), 3.76-3.61 (m, 2H), 3.48-3.26 (m, 5H), 3.08-2.92 (m, 3H), 2.58-2.42 (m, 3H), 1.87-1.49 (m, 4H)。
3-056: δ7.83-7.69 (m, 1H), 7.62-7.54 (m, 2H), 7.49-7.40 (m, 3H), 7.24-7.16 (m, 1H), 7.15-7.07 (m, 1H), 7.04-6.94 (m, 1H), 6.15-6.02 (m, 1H), 4.57-4.40 (m, 4H), 4.07-3.94 (m, 1H), 3.65-3.57 (m, 3H), 3.48-3.28 (m, 5H), 3.26-3.06 (m, 2H), 3.04-2.91 (m, 3H), 2.54-2.41 (m, 3H), 1.83-1.43 (m, 4H)。
3-057: δ7.76-7.36 (m, 6H), 7.24-7.15 (m, 1H), 7.15-6.92 (m, 2H), 5.55-5.11 (m, 1H), 4.61-4.27 (m, 4H), 4.07-3.77 (m, 1H), 3.42-3.26 (m, 3H), 3.05-2.79 (m, 6H), 2.52-2.37 (m, 3H), 1.47-0.85 (m, 3H)。
※NHに由来するプロトンは観測されなかった。
3-058: δ7.80-7.71 (m, 1H), 7.62-7.55 (m, 2H), 7.48-7.39 (m, 3H), 7.27-7.16 (m, 1H), 7.16-7.08 (m, 1H), 7.04-6.95 (m, 1H), 6.17-6.04 (m, 1H), 4.58-4.41 (m, 4H), 4.08-3.96 (m, 1H), 3.71-3.56 (m, 2H), 3.43-3.21 (m, 5H), 3.04-2.90 (m, 3H), 2.55-2.42 (m, 3H), 1.83-1.42 (m, 4H)。
3-059: δ7.69-7.31 (m, 7H), 7.00-6.93 (m, 1H), 6.16-5.88 (m, 1H), 4.61-4.45 (m, 2H), 4.03-3.87 (m, 1H), 3.75-2.65 (m, 13H), 2.55-2.40 (m, 3H), 1.82-1.30 (m, 4H)。
3-061: δ7.68-7.36 (m, 7H), 7.03-6.97 (m, 1H), 6.17-5.90 (m, 1H), 4.59-4.45 (m, 2H), 4.06-3.92 (m, 1H), 3.79-3.57 (m, 2H), 3.47-3.33 (m, 6H), 3.31-3.09 (m, 2H), 2.54-2.40 (m, 3H), 1.87-1.29 (m, 4H)。
3-062: δ7.64-6.75 (m, 7H), 6.18-5.92 (m, 1H), 4.60-4.42 (m, 2H), 4.18-3.88 (m, 1H), 3.76-2.79 (m, 13H), 2.57-2.40 (m, 6H), 1.81-1.20 (m, 4H)。
3-064: δ7.64-6.75 (m, 7H), 6.19-5.95 (m, 1H), 4.60-4.42 (m, 2H), 4.17-3.91 (m, 1H), 3.78-3.58 (m, 2H), 3.46-3.10 (m, 8H), 2.57-2.39 (m, 6H), 1.89-1.33 (m, 4H)。
3-065: δ7.73-7.19 (m, 10H), 6.18-5.88 (m, 1H), 4.62-4.39 (m, 2H), 4.18-3.81 (m, 1H), 3.78-2.80 (m, 13H), 2.57-2.41 (m, 3H), 1.81-1.17 (m, 4H)。
3-067: δ7.71-7.22 (m, 10H), 6.19-5.89 (m, 1H), 4.60-4.42 (m, 2H), 4.03-3.82 (m, 1H), 3.76-3.54 (m, 2H), 3.45-3.09 (m, 8H), 2.54-2.40 (m, 3H), 1.88-1.21 (m, 4H)。
3-068: δ7.62-7.38 (m, 5H), 7.05-6.94 (m, 1H), 6.15-6.04 (m, 1H), 4.59-4.45 (m, 2H), 4.18-4.03 (m, 1H), 3.86-3.11 (m, 13H), 2.52-2.41 (m, 3H), 1.81-1.46 (m, 4H), 1.33-1.19 (m, 9H)。
3-069: δ7.57-7.33 (m, 5H), 7.10-6.95 (m, 1H), 5.53-5.12 (m, 1H), 4.66-4.42 (m, 2H), 4.18-3.87 (m, 1H), 3.81-3.22 (m, 6H), 2.99-2.74 (m, 3H), 2.47-2.38 (m, 3H), 1.53-1.37 (m, 3H), 1.36-1.16 (m, 9H)。
※NHに由来するプロトンは観測されなかった。
3-070: δ7.62-7.39 (m, 5H), 6.13-5.96 (m, 1H), 4.59-4.45 (m, 2H), 4.10-2.93 (m, 17H), 2.54-2.40 (m, 3H), 2.13-1.97 (m, 3H), 1.82-1.40 (m, 4H)。
3-072: δ7.62-7.52 (m, 2H), 7.51-7.40 (m, 3H), 6.15-5.97 (m, 1H), 4.61-4.45 (m, 2H), 4.10-3.21 (m, 14H), 2.54-2.40 (m, 3H), 2.13-1.97 (m, 3H), 1.86-1.47 (m, 4H)。
3-073: δ8.95-7.35 (m, 7H), 6.17-6.02 (m, 1H), 4.61-4.44 (m, 2H), 4.16-2.89 (m, 14H), 2.54-2.39 (m, 3H), 1.84-1.17 (m, 4H)。
3-075: δ8.87-7.37 (m, 7H), 6.18-6.06 (m, 1H), 4.59-4.44 (m, 2H), 4.17-3.97 (m, 1H), 3.87-3.15 (m, 10H), 2.52-2.40 (m, 3H), 1.87-1.42 (m, 4H)。
3-076: δ7.51-6.86 (m, 7H), 5.94-5.80 (m, 1H), 4.73-4.57 (m, 2H), 4.54-4.44 (m, 2H), 3.97-3.87 (m, 4H), 3.70-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.05-2.97 (m, 3H), 2.53-2.43 (m, 3H), 1.76-1.44 (m, 4H)。
3-077: δ7.51-7.37 (m, 2H), 7.22-7.16 (m, 1H), 7.06-6.85 (m, 4H), 5.92-5.81 (m, 1H), 4.73-4.45 (m, 4H), 3.95-3.83 (m, 4H), 3.65-3.57 (m, 3H), 3.46-3.07 (m, 7H), 3.05-2.95 (m, 3H), 2.53-2.42 (m, 3H), 1.71-1.18 (m, 4H)。
3-078: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 6.30-6.21 (m, 1H), 6.12-6.00 (m, 1H), 5.94-5.80 (m, 1H), 4.57-4.47 (m, 2H), 4.01-3.25 (m, 13H), 3.03-2.94 (m, 3H), 2.54-2.44 (m, 3H), 1.78-1.47 (m, 4H)。
3-079: δ7.50-7.38 (m, 2H), 7.07-6.93 (m, 2H), 6.28-6.19 (m, 1H), 6.11-5.99 (m, 1H), 5.86-5.78 (m, 1H), 4.56-4.48 (m, 2H), 4.00-3.83 (m, 6H), 3.65-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.01-2.93 (m, 3H), 2.53-2.43 (m, 3H), 1.70-1.18 (m, 4H)。
3-080: δ7.84-6.93 (m, 8H), 5.95-5.86 (m, 1H), 4.59-4.40 (m, 4H), 4.00-3.85 (m, 4H), 3.70-3.53 (m, 2H), 3.41-3.22 (m, 5H), 3.04-2.94 (m, 3H), 2.53-2.45 (m, 3H), 1.78-1.44 (m, 4H)。
3-081: δ7.82-6.92 (m, 8H), 5.95-5.83 (m, 1H), 4.57-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.64-3.56 (m, 2H), 3.45-3.10 (m, 8H), 3.01-2.92 (m, 3H), 2.52-2.44 (m, 3H), 1.70-1.21 (m, 4H)。
3-082: δ7.52-7.39 (m, 2H), 7.33-7.28 (m, 1H), 7.26-7.20 (m, 2H), 7.06-6.94 (m, 2H), 5.95-5.85 (m, 1H), 4.55-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.72-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.04-2.95 (m, 3H), 2.52-2.45 (m, 3H), 1.78-1.47 (m, 4H)。
3-083: δ7.51-7.38 (m, 2H), 7.31-7.26 (m, 1H), 7.25-7.18 (m, 2H), 7.05-6.93 (m, 2H), 5.90-5.81 (m, 1H), 4.54-4.38 (m, 4H), 3.96-3.84 (m, 4H), 3.66-3.57 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.92 (m, 3H), 2.52-2.42 (m, 3H), 1.70-1.17 (m, 4H)。
3-084: δ8.86-7.38 (m, 4H), 7.05-6.92 (m, 2H), 5.99-5.82 (m, 1H), 4.58-4.45 (m, 2H), 4.02-3.18 (m, 17H), 2.51-2.37 (m, 3H), 1.80-1.37 (m, 4H)。
3-085: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.95-5.87 (m, 1H), 4.56-4.48 (m, 2H), 3.98-3.77 (m, 9H), 3.71-3.55 (m, 2H), 3.39-3.24 (m, 5H), 2.99-2.91 (m, 3H), 2.53-2.44 (m, 3H), 2.09-2.02 (m, 3H), 1.78-1.48 (m, 4H)。
3-086: δ7.51-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.87-5.84 (m, 1H), 4.55-4.48 (m, 2H), 3.97-3.75 (m, 9H), 3.74-3.59 (m, 5H), 3.43-3.13 (m, 5H), 2.97-2.91 (m, 3H), 2.51-2.44 (m, 3H), 2.07-2.02 (m, 3H), 1.66-1.50 (m, 4H)。
3-087: δ7.49-7.37 (m, 2H), 7.08-6.93 (m, 2H), 5.95-5.82 (m, 1H), 4.60-4.45 (m, 2H), 4.05-3.22 (m, 16H), 2.53-2.43 (m, 3H), 2.06-1.80 (m, 1H), 1.78-1.47 (m, 4H), 1.03-0.75 (m, 6H)。
3-088: δ7.49-7.37 (m, 2H), 7.06-6.93 (m, 2H), 5.90-5.80 (m, 1H), 4.61-4.46 (m, 2H), 4.06-3.14 (m, 19H), 2.53-2.42 (m, 3H), 2.08-1.73 (m, 1H), 1.68-1.16 (m, 4H), 1.03-0.73 (m, 6H)。
3-089: δ7.71-7.65 (m, 1H), 7.50-7.36 (m, 3H), 7.06-6.93 (m, 3H), 6.02-5.70 (m, 1H), 4.60-4.46 (m, 2H), 4.03-3.13 (m, 14H), 2.53-2.42 (m, 3H), 1.78-1.30 (m, 4H)。
3-090: δ7.93-6.91 (m, 7H), 5.99-5.52 (m, 1H), 4.62-4.47 (m, 2H), 4.01-2.79 (m, 17H), 2.53-2.41 (m, 3H), 1.69-1.14 (m, 4H)。
3-091: δ7.54-6.79 (m, 6H), 6.04-5.71 (m, 1H), 4.60-4.44 (m, 2H), 4.03-3.81 (m, 4H), 3.75-3.57 (m, 2H), 3.45-3.15 (m, 8H), 2.59-2.39 (m, 6H), 1.79-1.16 (m, 4H)。
3-092: δ7.55-6.76 (m, 6H), 6.02-5.68 (m, 1H), 4.63-4.45 (m, 2H), 4.04-2.91 (m, 17H), 2.61-2.39 (m, 6H), 1.69-1.13 (m, 4H)。
3-093: δ7.62-7.06 (m, 6H), 6.59-6.40 (m, 1H), 6.23-6.00 (m, 1H), 4.60-4.46 (m, 2H), 4.04-3.91 (m, 1H), 3.81-3.14 (m, 10H), 2.53-2.41 (m, 3H), 1.87-1.47 (m, 4H)。
3-094: δ8.73-7.20 (m, 8H), 6.26-6.03 (m, 1H), 4.61-4.43 (m, 2H), 4.11-3.91 (m, 1H), 3.79-3.17 (m, 10H), 2.53-2.37 (m, 3H), 1.88-1.20 (m, 4H)。
3-095: δ7.65-7.20 (m, 4H), 6.21-6.06 (m, 1H), 4.63-4.45 (m, 2H), 4.10-3.99 (m, 1H), 3.78-3.65 (m, 2H), 3.48-3.22 (m, 8H), 2.55-2.45 (m, 3H), 2.45-1.95 (m, 2H), 1.88-1.47 (m, 4H), 1.08-0.83 (m, 7H)。
3-096: δ8.77-7.20 (m, 7H), 6.21-5.87 (m, 1H), 4.61-4.43 (m, 2H), 4.04-3.90 (m, 1H), 3.78-3.63 (m, 2H), 3.44-3.15 (m, 8H), 2.52-2.40 (m, 3H), 1.82-1.34 (m, 4H)。
3-097: δ8.00-7.34 (m, 6H), 6.21-6.06 (m, 1H), 4.60-4.46 (m, 2H), 4.09-3.94 (m, 1H), 3.82-3.58 (m, 2H), 3.53-3.16 (m, 8H), 2.51-2.39 (m, 3H), 1.88-1.39 (m, 4H)。
3-099: δ7.61-7.27 (m, 5H), 6.66-6.26 (m, 1H), 6.19-5.95 (m, 1H), 4.56-4.46 (m, 2H), 4.10-3.90 (m, 4H), 3.79-3.65 (m, 2H), 3.51-3.16 (m, 8H), 2.52-2.39 (m, 3H), 1.88-1.13 (m, 4H)。
3-100: δ7.91-7.32 (m, 6H), 6.22-5.95 (m, 1H), 4.57-4.47 (m, 2H), 4.03-3.13 (m, 14H), 2.82-2.42 (m, 3H), 1.87-1.17 (m, 4H)。
3-102: δ7.88-6.88 (m, 6H), 6.25-5.99 (m, 1H), 4.60-4.44 (m, 2H), 4.11-3.89 (m, 1H), 3.79-3.62 (m, 2H), 3.49-3.16 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.31 (m, 4H)。
3-103: δ8.70-7.36 (m, 7H), 6.25-5.99 (m, 1H), 4.60-4.45 (m, 2H), 4.10-3.93 (m, 1H), 3.80-3.18 (m, 10H), 2.52-2.36 (m, 3H), 1.88-1.33 (m, 4H)。
3-104: δ8.08-8.02 (m, 1H), 7.75-7.67 (m, 1H), 7.61-7.23 (m, 5H), 6.23-6.05 (m, 1H), 4.58-4.49 (m, 2H), 4.08-3.92 (m, 1H), 3.78-3.18 (m, 10H), 2.52-2.38 (m, 3H), 1.86-1.33 (m, 4H)。
3-105: δ7.29-6.81 (m, 6H), 6.01-5.89 (m, 1H), 4.73-4.39 (m, 4H), 4.02-3.68 (m, 7H), 3.40-3.29 (m, 3H), 3.05-2.92 (m, 3H), 2.53-2.42 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H)。
3-106: δ7.31-7.05 (m, 5H), 6.97-6.87 (m, 1H), 6.01-5.89 (m, 1H), 4.55-4.37 (m, 4H), 4.02-3.68 (m, 7H), 3.39-3.29 (m, 3H), 3.01-2.89 (m, 3H), 2.52-2.43 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H)。
3-107: δ7.59-7.50 (m, 2H), 7.35-7.17 (m, 4H), 7.17-7.06 (m, 1H), 6.97-6.87 (m, 1H), 6.04-5.91 (m, 1H), 4.55-4.34 (m, 4H), 4.02-3.68 (m, 7H), 3.39-3.29 (m, 3H), 2.96-2.86 (m, 3H), 2.52-2.45 (m, 3H), 2.45-1.88 (m, 4H), 1.83-1.51 (m, 4H)。
3-108: δ7.82-7.72 (m, 1H), 7.30-6.88 (m, 6H), 6.04-5.93 (m, 1H), 4.57-4.39 (m, 4H), 4.02-3.60 (m, 7H), 3.40-3.30 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.89 (m, 4H), 1.84-1.53 (m, 4H)。
3-109: δ7.27-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.89 (m, 1H), 6.29-6.20 (m, 1H), 6.11-5.89 (m, 2H), 4.56-4.43 (m, 2H), 4.04-3.73 (m, 9H), 3.40-3.31 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.43 (m, 3H), 2.43-1.92 (m, 4H), 1.85-1.54 (m, 4H)。
3-110: δ7.28-7.18 (m, 1H), 7.18-7.07 (m, 1H), 6.96-6.86 (m, 1H), 6.05-5.89 (m, 1H), 4.59-4.44 (m, 2H), 4.07-3.95 (m, 1H), 3.94-3.69 (m, 6H), 3.58-3.13 (m, 6H), 2.50-2.40 (m, 3H), 2.41-1.91 (m, 4H), 1.89-1.14 (m, 13H)。
3-111: δ7.62-7.20 (m, 7H), 7.01-6.90 (m, 1H), 6.19-6.08 (m, 1H), 4.63-4.36 (m, 4H), 4.02-3.92 (m, 1H), 3.66-3.56 (m, 3H), 3.47-3.03 (m, 7H), 2.98-2.87 (m, 3H), 2.54-2.43 (m, 3H), 1.74-1.37 (m, 4H)。
3-112: δ7.61-6.95 (m, 8H), 6.17-6.07 (m, 1H), 4.61-4.33 (m, 4H), 4.02-3.91 (m, 1H), 3.67-3.56 (m, 3H), 3.46-3.05 (m, 7H), 2.96-2.87 (m, 3H), 2.53-2.44 (m, 3H), 1.73-1.41 (m, 4H)。
3-113: δ7.61-7.08 (m, 8H), 6.20-6.09 (m, 1H), 4.56-4.34 (m, 4H), 4.01-3.89 (m, 1H), 3.69-3.56 (m, 3H), 3.47-3.30 (m, 5H), 3.25-3.09 (m, 2H), 2.99-2.87 (m, 3H), 2.54-2.42 (m, 6H), 1.75-1.42 (m, 4H)。
3-114: δ7.75-7.35 (m, 5H), 7.25-7.17 (m, 1H), 6.98-6.91 (m, 1H), 6.85-6.80 (m, 1H), 6.21-6.09 (m, 1H), 4.57-4.34 (m, 4H), 4.02-3.92 (m, 1H), 3.85-3.73 (m, 3H), 3.67-3.56 (m, 3H), 3.46-3.29 (m, 5H), 3.26-3.07 (m, 2H), 3.03-2.93 (m, 3H), 2.55-2.43 (m, 3H), 1.73-1.42 (m, 4H)。
3-115: δ7.60-7.17 (m, 5H), 6.89-6.82 (m, 2H), 6.21-6.10 (m, 1H), 4.57-4.39 (m, 4H), 4.03-3.93 (m, 1H), 3.68-3.57 (m, 3H), 3.53-3.31 (m, 5H), 3.26-3.10 (m, 2H), 3.10-3.00 (m, 3H), 2.51-2.36 (m, 3H), 1.77-1.45 (m, 4H)。
3-116: δ7.61-7.35 (m, 4H), 7.13-7.09 (m, 1H), 6.79-6.74 (m, 1H), 6.19-6.10 (m, 1H), 4.68-4.43 (m, 4H), 4.01-3.91 (m, 1H), 3.68-3.58 (m, 3H), 3.48-3.30 (m, 5H), 3.26-3.06 (m, 2H), 3.02-2.93 (m, 3H), 2.52-2.43 (m, 3H), 2.31-2.21 (m, 3H), 1.74-1.42 (m, 4H)。
3-117: δ8.90-7.03 (m, 6H), 6.20-6.10 (m, 1H), 4.89-4.47 (m, 4H), 4.05-3.92 (m, 1H), 3.66-3.58 (m, 3H), 3.47-3.29 (m, 5H), 3.25-3.01 (m, 5H), 2.52-2.45 (m, 3H), 1.76-1.42 (m, 4H)。
3-118: δ7.61-7.35 (m, 5H), 6.13-6.04 (m, 1H), 4.64-4.46 (m, 4H), 4.04-3.93 (m, 1H), 3.68-3.58 (m, 3H), 3.47-3.30 (m, 5H), 3.26-3.07 (m, 2H), 3.03-2.91 (m, 3H), 2.53-2.41 (m, 3H), 1.74-1.44 (m, 4H)。
3-119: δ8.46-7.21 (m, 7H), 6.15-6.03 (m, 1H), 4.77-4.36 (m, 4H), 4.04-3.93 (m, 1H), 3.67-3.56 (m, 3H), 3.45-3.06 (m, 7H), 2.98-2.89 (m, 3H), 2.52-2.41 (m, 3H), 1.74-1.44 (m, 4H)。
3-120: δ7.61-7.36 (m, 4H), 6.20-6.08 (m, 1H), 4.59-4.46 (m, 2H), 4.05-3.93 (m, 1H), 3.69-3.56 (m, 3H), 3.52-3.32 (m, 5H), 3.24-3.08 (m, 4H), 3.07-2.97 (m, 3H), 2.54-2.43 (m, 3H), 1.79-1.48 (m, 4H), 1.04-0.89 (m, 1H), 0.46-0.32 (m, 2H), 0.15-0.06 (m, 2H)。
3-121: δ7.61-7.36 (m, 4H), 6.20-5.94 (m, 3H), 4.57-4.46 (m, 2H), 4.18-4.08 (m, 2H), 4.04-3.94 (m, 1H), 3.67-3.61 (m, 3H), 3.49-3.32 (m, 5H), 3.27-3.10 (m, 2H), 3.07-3.00 (m, 3H), 2.51-2.42 (m, 3H), 1.76-1.45 (m, 4H)。
3-122: δ8.97-7.33 (m, 7H), 7.29-7.20 (m, 1H), 6.22-5.91 (m, 1H), 4.56-4.43 (m, 2H), 4.09-3.86 (m, 1H), 3.78-3.58 (m, 2H), 3.46-3.14 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.29 (m, 4H)。
3-125: δ7.90-7.83 (m, 2H), 7.37-7.20 (m, 4H), 7.15-7.05 (m, 1H), 6.94-6.87 (m, 1H), 5.98-5.85 (m, 1H), 4.64-4.34 (m, 4H), 4.00-3.71 (m, 10H), 3.40-3.28 (m, 3H), 3.08-2.98 (m, 3H), 2.49-2.41 (m, 3H), 2.39-1.86 (m, 4H), 1.82-1.53 (m, 4H)。
3-126: δ7.28-7.21 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.03-5.91 (m, 1H), 4.55-4.42 (m, 2H), 4.02-3.70 (m, 12H), 3.39-3.30 (m, 3H), 2.96-2.89 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.91 (m, 7H), 1.84-1.51 (m, 4H)。
3-128: δ7.86-7.06 (m, 5H), 6.96-6.87 (m, 1H), 6.09-5.78 (m, 1H), 4.57-4.41 (m, 2H), 4.07-3.72 (m, 7H), 3.50-3.32 (m, 6H), 2.57-1.88 (m, 7H), 1.87-1.31 (m, 4H)。
3-129: δ8.86-8.25 (m, 2H), 7.24-7.18 (m, 1H), 7.16-7.08 (m, 1H), 6.96-6.87 (m, 1H), 6.08-5.91 (m, 1H), 4.59-4.43 (m, 2H), 4.06-3.73 (m, 7H), 3.50-3.32 (m, 6H), 2.50-1.88 (m, 7H), 1.78-1.50 (m, 4H)。
3-130: δ7.27-7.05 (m, 2H), 6.97-6.86 (m, 1H), 6.10-5.90 (m, 1H), 4.58-4.43 (m, 2H), 4.06-3.94 (m, 1H), 3.94-3.86 (m, 3H), 3.79-3.72 (m, 3H), 3.50-3.20 (m, 6H), 2.71-2.55 (m, 1H), 2.51-1.91 (m, 7H), 1.86-1.33 (m, 8H), 1.11-0.77 (m, 6H)。
3-131: δ7.72-7.64 (m, 1H), 7.56-7.40 (m, 2H), 7.35-7.07 (m, 4H), 6.96-6.86 (m, 1H), 6.11-5.76 (m, 1H), 4.58-4.38 (m, 2H), 4.18-3.70 (m, 7H), 3.42-3.28 (m, 6H), 2.54-1.39 (m, 11H)。
3-132: δ7.27-7.18 (m, 1H), 7.18-7.04 (m, 1H), 6.97-6.86 (m, 1H), 6.05-5.90 (m, 1H), 4.59-4.41 (m, 2H), 4.06-3.61 (m, 9H), 3.45-3.25 (m, 6H), 2.70-1.52 (m, 12H), 1.06-0.69 (m, 6H)。
3-133: δ7.27-7.19 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.02-5.97 (m, 1H), 4.55-4.47 (m, 2H), 4.03-3.86 (m, 4H), 3.78-3.70 (m, 3H), 3.39-3.31 (m, 3H), 3.28-3.17 (m, 2H), 3.02-2.92 (m, 3H), 2.52-2.45 (m, 3H), 2.45-2.10 (m, 4H), 2.07-0.78 (m, 13H)。
3-134: δ7.29-7.22 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.04-5.98 (m, 1H), 4.55-4.47 (m, 2H), 4.04-3.72 (m, 9H), 3.58-3.52 (m, 3H), 3.39-3.31 (m, 3H), 3.03-2.95 (m, 3H), 2.51-2.44 (m, 3H), 2.42-1.89 (m, 4H), 1.87-1.57 (m, 4H), 1.34-1.07 (m, 9H)。
3-135: δ7.25-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.85 (m, 1H), 4.60-4.44 (m, 2H), 4.05-2.97 (m, 16H), 2.53-1.92 (m, 10H), 1.81-1.55 (m, 4H)。
3-136: δ8.15-6.90 (m, 9H), 6.00-5.65 (m, 1H), 4.57-4.38 (m, 2H), 4.05-3.13 (m, 14H), 2.55-2.35 (m, 3H), 1.82-1.30 (m, 4H)。
3-137: δ8.14-6.90 (m, 9H), 5.97-5.62 (m, 1H), 4.58-4.43 (m, 2H), 4.03-2.87 (m, 17H), 2.54-2.37 (m, 3H), 1.70-1.20 (m, 4H)。
3-138: δ7.26-7.18 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.08-5.90 (m, 1H), 4.59-4.42 (m, 2H), 4.05-3.19 (m, 17H), 2.53-2.42 (m, 3H), 2.41-1.92 (m, 4H), 1.87-1.53 (m, 8H)。
3-139: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 5.99-5.93 (m, 1H), 4.56-4.47 (m, 2H), 4.04-3.94 (m, 1H), 3.93-3.85 (m, 3H), 3.78-3.71 (m, 3H), 3.41-3.33 (m,3H), 3.33-3.21 (m, 4H), 3.21-3.13 (m, 3H), 2.51-1.91 (m, 7H), 1.79-1.41 (m, 10H)。
3-140: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 5.94-5.88 (m, 1H), 4.55-4.47 (m, 2H), 4.28-4.14 (m, 1H), 4.04-3.92 (m, 1H), 3.92-3.85 (m, 3H), 3.78-3.70 (m, 3H), 3.41-3.33 (m,3H), 3.17-3.08 (m, 3H), 2.65-2.56 (m, 3H), 2.51-1.91 (m, 7H), 1.78-1.57 (m, 4H), 1.41-0.99 (m, 6H)。
4-001: δ7.40-6.80 (m, 3H), 6.09 (s, 1H), 6.02 (s, 1H), 4.30-3.20 (m, 17H), 2.95 (s, 3H), 2.55 (s, 3H), 2.10-2.00 (m, 3H), 1.80-1.50 (m, 4H)。
4-002: δ7.70-6.85 (m, 6H), 6.09 (s, 1H), 5.81 (s, 1H), 4.25-3.10 (m, 12H), 2.54 (s, 3H), 2.03 (s, 3H), 1.85-1.15 (m, 4H)。
4-003: δ7.25-7.19 (m, 2H), 7.16-7.07 (m, 1H), 7.07-7.01 (m, 1H), 6.95-6.87 (m, 2H), 6.05-5.87 (m, 1H), 4.73-4.51 (m, 2H), 3.98-3.82 (m, 4H), 3.71-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.06-2.93 (m, 3H), 2.65-2.51 (m, 3H), 2.37-2.23 (m, 3H), 1.79-1.44 (m, 4H)。
4-004: δ7.25-7.18 (m, 2H), 7.18-7.08 (m, 1H), 7.07-7.00 (m, 1H), 6.95-6.87 (m, 2H), 5.95-5.89 (m, 1H), 4.72-4.50 (m, 2H), 3.98-3.82 (m, 4H), 3.74-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.05-2.96 (m, 3H), 2.91-2.83 (m, 3H), 2.66-2.56 (m, 3H), 1.78-1.43 (m, 4H)。
4-006: δ7.80-6.80 (m, 6H), 6.00-5.20 (m, 2H), 3.90-3.20 (m, 15H), 2.50-2.40 (m, 3H), 1.80-1.50 (m, 4H)。
4-007: δ7.35-6.80 (m, 6H), 6.00-5.90 (m, 2H), 4.72-4.50 (m, 2H), 4.00-3.20 (m, 12H), 3.10-2.90 (m, 3H), 2.55-2.40 (m, 3H), 1.85-1.50 (m, 4H)。
4-011: δ7.78-7.68 (m, 1H), 7.64-7.55 (m, 1H), 7.50-6.90 (m, 6H), 6.17-6.09 (m, 1H), 4.54-4.41 (m, 2H), 4.34-4.24 (m, 2H), 4.05-3.93 (m, 1H), 3.75-3.61 (m, 2H), 3.51-3.40 (m, 2H), 3.39-3.25 (m, 2H), 3.03-2.95 (m, 3H), 2.92-2.83 (m, 3H), 1.84-1.70 (m, 2H), 1.63-1.46 (m, 2H)。
――――――――――――――――――――――――――――――――――
[試験例]
次に、本発明化合物の一態様に係る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が、本発明はこれらのみに限定されるものではない。なお、試験例中「RH」とは相対湿度(relative humidity)を表し、例えば、「湿度100%RH」の記載は、相対湿度が100%であることを表す。 [Table 7]
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No. 1 H-NMR
――――――――――――――――――――――――――――――――――
1-001: δ7.26-7.19 (m, 1H), 7.16-7.00 (m, 1H), 6.99-6.85 (m, 1H), 6.10&5.94 (s, 1H), 4.52-4.35 (m, 2H) ), 4.07-3.86 (m, 6H), 3.76-3.61 (m, 2H), 3.40-3.23 (m, 5H), 2.84&2.82 (s, 3H), 1.81-1.48 (m, 13H).
1-013: δ7.48-7.35 (m, 2H), 7.35-7.10 (m, 3H), 7.08-6.99 (m, 1H), 6.98-6.85 (m, 1H), 6.12 (s, 1H), 4.74 -4.55 (m, 2H), 4.50-4.38 (m, 2H), 4.07-3.93 (m, 3H), 3.73-3.59 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H) , 2.83 (s, 3H), 1.81-1.46 (m, 4H).
1-014: δ7.51-7.39 (m, 2H), 7.25-7.16 (m, 1H), 7.08-6.84 (m, 4H), 5.84 (s, 1H), 4.74-4.57 (m, 2H), 4.49 -4.35 (m, 2H), 4.08-3.87 (m, 6H), 3.73-3.56 (m, 2H), 3.39-3.22 (m, 2H), 3.01 (s, 3H), 2.82 (s, 3H), 1.80 -1.46 (m, 4H).
1-016: δ7.47-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.11 (m, 1H), 6.14 (s, 1H), 4.49-4.36 (m, 2H), 4.06 -3.96 (m, 3H), 3.90-3.76 (m, 5H), 3.74-3.61 (m, 2H), 3.40-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.85-1.50 (m, 4H).
1-017: δ7.29-7.37 (m, 2H), 7.19-7.13 (m, 2H), 7.05-6.90 (m, 3H), 5.85 (s, 1H), 4.65-4.49 (m, 2H), 4.45 -4.35 (m, 2H), 4.06-3.97 (m, 2H), 3.96-3.86 (m, 4H), 3.75-3.55 (m, 2H), 3.40-3.20 (m, 2H), 3.10 (s, 3H) , 2.78 (s, 3H), 1.80-1.45 (m, 4H).
1-018: δ7.45-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.20-7.10 (m, 3H), 7.00-6.92 (m, 1H), 6.13 (s, 1H), 4.64 -4.48 (m, 2H), 4.47-4.35 (m, 2H), 4.05-3.95 (m, 3H), 3.76-3.60 (m, 2H), 3.38-3.25 (m, 2H), 3.08 (s, 3H) , 2.79 (s, 3H), 1.85-1.50 (m, 4H).
1-025: δ8.56-8.52 (m, 1H), 8.34-8.29 (m, 1H), 7.50-7.38 (m, 2H), 7.05-6.94 (m, 2H), 5.85 (s, 1H), 4.49 -4.35 (m, 2H), 4.08-3.88 (m, 6H), 3.80-3.55 (m, 2H), 3.48 (s, 3H), 3.40-3.20 (m, 2H), 2.77 (s, 3H), 1.80 -1.45 (m, 4H).
1-026: δ8.60-8.55 (m, 1H), 8.35-8.30 (m, 1H), 7.47-7.34 (m, 2H), 7.32-7.24 (m, 1H), 7.21-7.12 (m, 1H) , 6.12 (s, 1H), 4.50-4.39 (m, 2H), 4.10-3.95 (m, 3H), 3.82-3.60 (m, 2H), 3.47 (s, 3H), 3.40-3.20 (m, 2H) , 2.77 (s, 3H), 1.86-1.43 (m, 4H).
1-027: δ7.50-7.40 (m, 2H), 7.10-6.95 (m, 2H), 6.91&5.84 (s, 1H), 4.50-4.35 (m, 2H), 4.08-3.75 (m, 8H) ), 3.73-3.59 (m, 2H), 3.40-3.27 (s, 5H), 2.82 (s, 3H), 2.05-1.45 (m, 5H), 1.02-0.78 (m, 6H).
1-028: δ7.47-7.35 (m, 2H), 7.32-7.25 (m, 1H), 7.23-7.13 (m, 1H), 6.17&6.11 (s, 1H), 4.50-4.37 (m, 2H) ), 4.10-3.75 (m, 5H), 3.75-3.61 (m, 2H), 3.40-3.20 (m, 5H), 2.82 (s, 3H), 2.05-1.50 (m, 5H), 1.01-0.78 (m , 6H).
1-031: δ7.25-7.19 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 5.98 (s, 1H), 4.48-4.35 (m, 2H), 4.06 -3.96 (m, 2H), 3.96-3.61 (m, 12H), 3.48-3.30 (m, 2H), 3.28-3.11 (m, 2H), 2.95 (s, 3H), 2.83 (s, 3H), 2.04 (s, 3H), 1.70-1.48 (m, 4H).
1-038: δ7.24-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.00&5.92 (s, 1H), 4.50-4.36 (m, 2H), 4.08-3.88 (m, 8H) ), 3.63 (s, 3H), 3.50-3.12 (m, 7H), 2.81 (s, 3H), 2.05-1.48 (m, 5H), 1.01-0.77 (m, 6H).
1-042: δ7.61-7.55 (m, 2H), 7.48-7.41 (m, 3H), 6.08 (s, 1H), 4.47-4.38 (m, 2H), 4.10-3.96 (m, 3H), 3.91 -3.77 (m, 2H), 3.80 (s, 3H), 3.71-3.60 (m, 2H), 3.39-3.26 (m, 2H), 2.96 (s, 3H), 2.83 (s, 3H), 2.05 (s , 3H), 1.82-1.50 (m, 4H).
1-046: δ7.62-7.55 (m, 2H), 7.50-7.40 (m, 3H), 6.06 (s, 1H), 4.49-4.34 (m, 2H), 4.08-3.97 (m, 3H), 3.91 -3.76 (m, 2H), 3.79 (s, 3H), 3.63 (s, 3H), 3.49-3.33 (m, 2H), 3.25-3.09 (m, 2H), 2.95 (s, 3H), 2.83 (s , 3H), 2.05 (s, 3H), 1.77-1.47 (m, 4H).
1-047: δ7.60-7.54 (m, 2H), 7.49-7.41 (m, 3H), 6.28-6.21 (m, 1H), 6.10-5.99 (m, 1H), 6.03 (s, 1H), 4.48 -4.39 (m, 2H), 4.09-3.82 (m, 4H), 3.73-3.65 (m, 1H), 3.62 (s, 3H), 3.52-3.38 (m, 2H), 3.20-3.05 (m, 2H) , 2.97 (s, 3H), 2.82 (s, 3H), 1.77-1.45 (m, 4H).
1-059: δ8.60-8.50 (m, 1H), 8.35-8.30 (m, 1H), 7.60-7.52 (m, 1H), 7.50-7.34 (m, 3H), 6.11 (s, 1H), 4.50 -4.37 (m, 2H), 4.10-3.89 (m, 3H), 3.80-3.60 (m, 2H), 3.46 (s, 3H), 3.40-3.15 (m, 2H), 2.77 (s, 3H), 1.90 -1.40 (m, 4H).
1-063: δ7.25-7.20 (m, 1H), 7.18-7.09 (m, 1H), 6.96-6.89 (m, 1H), 6.08&5.98 (s, 1H), 4.50-4.38 (m, 2H) ), 4.20-3.88 (m, 8H), 3.73-3.60 (m, 2H), 3.38-3.29 (m, 5H), 2.83&2.82 (s, 3H), 1.80-1.50 (m, 6H), 1.03- 0.80 (m, 3H).
1-064: δ7.60-7.58 (m, 1H), 7.50-7.36 (m, 3H), 7.24-7.20 (m, 1H), 7.06-7.03 (m, 1H), 6.95-6.90 (m, 1H) , 6.11 (s, 1H), 4.72-4.57 (m, 2H), 4.47-4.39 (m, 2H), 4.08-3.92 (m, 3H), 3.71-3.59 (m, 2H), 3.38-3.24 (m, 2H), 3.01 (s, 3H), 2.83 (s, 3H), 1.80-1.45 (m, 4H).
1-065: δ7.62-7.57 (m, 1H), 7.52-7.37 (m, 3H), 6.30-6.24 (m, 1H), 6.15-5.94 (m, 2H), 4.49-4.40 (m, 2H) , 4.06-3.84 (m, 5H), 3.72-3.62 (m, 2H), 3.38-3.29 (m, 2H), 2.98 (s, 3H), 2.83 (s, 3H), 1.80-1.50 (m, 4H) .
1-066: δ7.76-7.68 (m, 1H), 7.62-7.58 (m, 1H), 7.52-7.30 (m, 3H), 7.25-7.19 (m, 1H), 7.16-6.95 (m, 2H) , 6.13 (s, 1H), 4.54-4.38 (m, 4H), 4.06-3.90 (m, 3H), 3.70-3.60 (m, 2H), 3.39-3.25 (m, 2H), 2.99 (s, 3H) , 2.88&2.83 (s, 3H), 1.80-1.50 (m, 4H).
1-067: δ7.24-7.03 (m, 2H), 6.95-6.70 (m, 1H), 6.05 & 5.90 (s, 1H), 4.49-4.36 (m, 2H), 4.10-3.95 (m, 2H) , 3.90 & 3.89 (s, 3H), 3.85-3.72 (m, 1H), 3.30 & 3.25 (s, 3H), 2.84 & 2.82 (s, 3H), 2.75-2.51 (m, 2H), 2.40-2.20 ( m, 2H), 2.06-1.66 (m, 4H), 1.53 & 1.41 (s, 9H).
1-068: δ7.29-7.20 (m, 1H), 7.16-7.06 (m, 1H), 6.94-6.84 (m, 1H), 6.17-5.81 (m, 1H), 4.73-4.61 (m, 1H) , 4.47-4.34 (m, 2H), 4.08-3.97 (m, 2H), 3.92-3.84 (m, 3H), 3.38-3.22 (m, 6H), 3.05-2.97 (m, 3H), 2.86-2.77 ( m, 3H), 1.56-1.17 (m, 12H).
1-069: δ7.59-7.38 (m, 1H), 7.17-7.05 (m, 1H), 6.94-6.85 (m, 1H), 6.29-5.88 (m, 1H), 4.47-4.32 (m, 3H) , 4.07-3.96 (m, 2H), 3.93-3.87 (m, 3H), 3.40-3.04 (m, 5H), 2.86-2.71 (m, 6H), 2.20-2.00 (m, 2H), 1.57-1.34 ( m, 9H).
1-070: δ7.27-7.20 (m, 1H), 7.16-7.03 (m, 1H), 6.96-6.86 (m, 1H), 6.09 & 5.94 (s, 1H), 4.49-4.36 (m, 2H) , 4.10-3.96 (m, 2H), 3.90 & 3.89 (s, 3H), 3.74-3.62 (m, 1H), 3.29 & 3.24 (s, 3H), 2.84 & 2.82 (s, 3H), 1.74-1.01 ( m, 19H).
1-071: δ7.28-7.18 (m, 1H), 7.16-7.04 (m, 1H), 6.94-6.86 (m, 1H), 6.10-5.89 (m, 1H), 4.48-4.37 (m, 2H) , 4.08-3.98 (m, 2H), 3.92-3.86 (m, 3H), 3.82-3.68 (m, 1H), 3.30-3.06 (m, 7H), 2.85-2.78 (m, 3H), 1.86-1.13 ( m, 17H).
1-072: δ7.30-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.16-5.87 (m, 1H), 4.50-4.37 (m, 3H), 4.09-3.94 (m, 2H) , 3.94-3.86 (m, 3H), 3.73-3.33 (m, 4H), 3.30-3.21 (m, 3H), 2.86-2.79 (m, 3H), 2.14-1.97 (m, 3H), 1.67-1.19 ( m, 13H).
1-073: δ7.27-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.17-5.82 (m, 1H), 4.48-4.37 (m, 2H), 4.09-3.94 (m, 3H) , 3.93-3.87 (m, 3H), 3.58-3.08 (m, 7H), 2.85-2.77 (m, 3H), 2.34-2.18 (m, 2H), 1.72-1.34 (m, 13H), 1.13-1.03 ( m, 3H).
1-078: δ7.50-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.95-6.87 (m, 1H), 5.97-5.85 (m, 1H), 4.49-4.36 (m, 2H) , 4.09-3.94 (m, 3H), 3.93-3.88 (m, 3H), 3.77-3.73 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.78 (m, 3H), 2.43-2.15 ( m, 4H), 1.82-1.34 (m, 13H).
1-079: δ7.48-7.45 (m, 1H), 7.43-7.35 (m, 1H), 6.94-6.88 (m, 1H), 5.97 & 5.86 (s, 1H), 4.50-4.37 (m, 2H) , 4.09-3.87 (m, 3H), 3.91 & 3.90 (s, 3H), 3.62 (s, 3H), 3.50-3.11 (m, 4H), 3.28 & 3.23 (s, 3H), 2.85-2.78 (m, 3H), 1.72-1.23 (m, 13H).
1-086: δ7.28-7.07 (m, 2H), 6.98-6.84 (m, 1H), 6.09-5.88 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.22 (m, 12H) , 2.89-2.77 (m, 3H), 2.71-1.95 (m, 5H), 1.91-1.36 (m, 4H), 1.10-0.76 (m, 10H).
1-089: δ7.28-7.20 (m, 1H), 7.18-7.07 (m, 1H), 6.97-6.87 (m, 1H), 6.05-5.90 (m, 1H), 4.50-4.36 (m, 2H) , 4.10-3.94 (m, 5H), 3.93-3.88 (m, 3H), 3.28-3.20 (m, 3H), 2.84-2.79 (m, 3H), 2.46-1.93 (m, 4H), 1.79-1.62 ( m, 4H), 1.55-1.36 (m, 9H), 1.22-1.14 (m, 3H).
1-090: δ7.41-7.28 (m, 1H), 7.28-7.08 (m, 2H), 6.96-6.88 (m, 1H), 6.04-5.89 (m, 1H), 4.49-4.36 (m, 2H) , 4.10-3.96 (m, 3H), 3.93-3.86 (m, 3H), 3.29-3.19 (m, 3H), 2.85-2.78 (m, 3H), 2.48-1.95 (m, 4H), 1.82-1.61 ( m, 4H), 1.54-1.35 (m, 9H).
1-091: δ7.25-7.03 (m, 2H), 6.98-6.81 (m, 1H), 6.10-5.87 (m, 1H), 4.49-4.37 (m, 2H), 4.10-3.87 (m, 6H) , 3.62-3.56 (m, 3H), 3.32-3.22 (m, 3H), 2.86-2.79 (m, 3H), 2.28-1.17 (m, 18H).
1-092: δ7.33-7.20 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 5.98 (s, 1H), 4.52-4.37 (m, 4H), 4.07 -3.95 (m, 3H), 3.93-3.72 (m, 8H), 2.96-2.90 (m, 3H), 2.83-2.79 (m, 3H), 2.40-1.87 (m, 10H), 1.79-1.59 (m, 4H).
1-093: δ7.28-7.20 (m, 1H), 7.15-7.03 (m, 1H), 6.95-6.86 (m, 1H), 6.19-5.89 (m, 1H), 4.50-4.35 (m, 3H) , 4.09-3.94 (m, 4H), 3.93-3.81 (m, 3H), 3.80-3.71 (m, 3H), 3.70-3.59 (m, 1H), 3.04-2.93 (m, 3H), 2.84-2.69 ( m, 3H), 2.47-1.94 (m, 7H), 1.79-1.56 (m, 4H).
1-094: δ7.29-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.87 (m, 1H), 4.49-4.35 (m, 2H), 4.17-3.84 (m, 8H) , 3.56-3.03 (m, 7H), 2.84-2.76 (m, 3H), 1.76-1.14 (m, 16H).
1-096: δ7.29-7.08 (m, 2H), 6.96-6.86 (m, 1H), 5.96 (s, 1H), 4.49-4.39 (m, 2H), 4.09-3.98 (m, 3H), 3.90 (s, 3H), 3.41-2.73 (m, 10H), 2.68 (s, 3H), 1.88-1.65 (m, 4H), 1.57-1.49 (m, 9H).
1-100: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.02-5.91 (m, 1H), 4.49-4.38 (m, 2H), 4.17-3.94 (m, 4H) , 3.92-3.87 (m, 3H), 3.79-3.69 (m, 4H), 3.35-3.26 (m, 3H), 2.81 (s, 3H), 2.42-1.93 (m, 4H), 1.89-1.53 (m, 4H), 1.01-0.74 (m, 7H).
1-102: δ7.56-7.49 (m, 2H), 7.36-7.19 (m, 4H), 7.16-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.01-5.96 (m, 1H) , 4.49-4.35 (m, 4H), 4.07-3.89 (m, 3H), 3.91 (s, 3H), 3.75-3.71 (m, 3H), 2.92 (s, 3H), 2.83 (s, 3H), 2.40 -1.91 (m, 4H), 1.76-1.51 (m, 4H).
1-105: δ7.28-7.19 (m, 1H), 7.17-7.07 (m, 1H), 6.95-6.88 (m, 1H), 6.00-5.96 (m, 1H), 4.47-4.38 (m, 2H) , 4.07-3.70 (m, 14H), 2.96-2.91 (m, 3H), 2.84-2.81 (m, 3H), 2.52-1.59 (m, 11H).
1-106: δ7.28-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.29-6.20 (m, 1H), 6.10-5.93 (m, 2H) , 4.48-4.37 (m, 2H), 4.07-3.81 (m, 5H), 3.91 (s, 3H), 3.75 (s, 3H), 2.96 (s, 3H), 2.81 (s, 3H), 2.39-1.94 (m, 4H), 1.78-1.60 (m, 4H).
1-107: δ7.78-7.68 (m, 1H), 7.28-6.86 (m, 6H), 6.00-5.94 (m, 1H), 4.55-4.36 (m, 4H), 4.08-3.86 (m, 3H) , 3.91 (s, 3H), 3.76-3.71 (m, 3H), 2.96 (s, 3H), 2.82 (s, 3H), 2.38-1.92 (m, 4H), 1.76-1.53 (m, 4H).
1-108: δ7.29-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.04-5.85 (m, 1H), 4.50-4.39 (m, 2H), 4.18-3.94 (m, 3H) , 3.94-3.87 (m, 3H), 3.81-3.71 (m, 3H), 3.60-3.47 (m, 3H), 3.38-3.33 (m, 3H), 2.84-2.79 (m, 3H), 2.52-1.91 ( m, 7H), 1.84-1.54 (m, 4H).
1-109: δ7.25-7.08 (m, 2H), 7.04-6.88 (m, 1H), 6.07-5.88 (m, 1H), 4.49-4.39 (m, 2H), 4.08-3.88 (m, 6H) , 3.32-2.94 (m, 7H), 2.85-2.80 (m, 3H), 2.71 (s, 6H), 1.81-1.38 (m, 13H).
2-003: δ7.24-7.15 (m, 1H), 7.15-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.93 (s, 1H), 3.98-3.87 (m, 4H) ), 3.78-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.54&2.53 (s, 3H), 2.12&2.11 (s, 3H), 1.80-1.35 (m, 13H).
2-004: δ7.24-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.09&5.94 (s, 1H), 3.98-3.87 (m, 4H) ), 3.75-3.60 (m, 2H), 3.40-3.22 (m, 5H), 2.53&2.51 (s, 3H), 1.82-1.35 (m, 14H), 1.00-0.80 (m, 4H).
2-005: δ7.60-7.49 (m, 2H), 7.40-7.05 (m, 5H), 6.95-6.83 (m, 1H), 6.08-5.98 (m, 1H), 4.50-4.37 (m, 2H) , 3.98-3.84 (m, 4H), 3.70-3.51 (m, 2H), 3.39-3.22 (m, 2H), 3.00-2.89 (m, 3H), 2.54 (s, 3H), 2.11 (s, 3H) , 1.75-1.42 (m, 4H).
2-006: δ7.78-7.70 (m, 1H), 7.27-7.05 (m, 4H), 7.03-6.85 (m, 2H), 6.01 (s, 1H), 4.55-4.40 (m, 2H), 4.00 -3.85 (m, 4H), 3.69-3.50 (m, 2H), 3.39-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.79-1.45 (m, 4H).
2-007: δ7.59-7.49 (m, 2H), 7.38-7.09 (m, 5H), 6.95-6.88 (m, 1H), 5.99 (s, 1H), 4.49-4.35 (m, 2H), 3.95 -3.83 (m, 4H), 3.70-3.52 (m, 2H), 3.48 (s, 1H), 3.39-3.21 (m, 2H), 2.94 (s, 3H), 2.59 (s, 3H), 1.88-1.42 (m, 4H).
2-008: δ7.70-7.62 (m, 1H), 7.57-7.10 (m, 6H), 6.98-6.84 (m, 1H), 6.11&5.77 (s, 1H), 4.05-3.78 (m, 4H) ), 3.75-3.51 (m, 2H), 3.51&3.48 (s, 1H), 3.41-3.12 (m, 5H), 2.61&2.53 (s, 3H), 1.82-1.18 (m, 4H).
2-011: δ7.70-7.59 (m, 1H), 7.52-7.42 (m, 1H), 7.29-7.07 (m, 2H), 6.95-6.86 (m, 1H), 6.10-5.92 (m, 1H) , 4.04-3.83 (m, 4H), 3.80-3.55 (m, 2H), 3.49 (s, 3H), 3.44-3.18 (m, 2H), 2.58-2.45 (m, 3H), 2.13 (s, 3H) , 1.82-1.37 (m, 4H).
2-012: δ7.29-7.05 (m, 2H), 6.95-6.85 (m, 1H), 6.07-5.94 (m, 1H), 3.96-3.75 (m, 9H), 3.72-3.53 (m, 2H) , 3.41-3.28 (m, 2H), 3.00-2.89 (m, 3H), 2.64-2.46 (m, 3H), 2.16-2.11 (m, 3H), 2.09-2.00 (m, 3H), 1.78-1.49 ( m, 4H).
2-013: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.91 (m, 1H), 4.06-3.72 (m, 6H), 3.71-3.58 (m, 2H) , 3.41-3.26 (m, 5H), 2.55-2.45 (m, 3H), 2.17-2.06 (m, 3H), 2.05-1.80 (m, 1H), 1.76-1.45 (m, 4H), 1.07-0.70 ( m, 6H).
2-014: δ7.71-7.41 (m, 3H), 7.38-7.09 (m, 4H), 6.98-6.85 (m, 1H), 6.12&5.78 (s, 1H), 4.02-3.79 (m, 4H) ), 3.76-3.53 (m, 2H), 3.43-3.15 (m, 5H), 2.56&2.47 (s, 3H), 2.12&2.10 (s, 3H), 1.82-1.31 (m, 4H).
2-015: δ7.71-7.54 (m, 1H), 7.41-7.35 (m, 1H), 7.27-7.07 (m, 2H), 7.04-6.97 (m, 1H), 6.95-6.85 (m, 1H) , 5.84 (s, 1H), 4.00-3.80 (m, 4H), 3.78-3.59 (m, 2H), 3.41 (s, 3H), 3.32-3.15 (m, 2H), 2.59-2.47 (m, 3H) , 2.13 (s, 3H), 1.80-1.30 (m, 4H).
2-016: δ7.71-6.90 (m, 3H), 6.02 (s, 1H), 5.55 (br, 1H), 4.00-3.80 (m, 4H), 3.69-3.56 (m, 2H), 3.50 (s , 1H), 3.39-3.25 (m, 2H), 2.80 (s, 3H), 2.61 (s, 3H), 1.79-1.45 (m, 4H).
2-018: δ7.25-7.09 (m, 2H), 6.97-6.89 (m, 1H), 6.06-5.94 (m, 1H), 3.99-3.85 (m, 4H), 3.76-3.60 (m, 2H) , 3.41-3.23 (m, 5H), 2.57-2.34 (m, 6H), 2.12 (s, 3H), 1.78-1.50 (m, 4H).
2-019: δ7.29-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.94-6.87 (m, 2H), 5.99 (s, 1H), 4.70-4.53 (m, 2H), 3.98 -3.80 (m, 4H), 3.70-3.50 (m, 2H), 3.39-3.21 (m, 2H), 3.01 (s, 3H), 2.53 (s, 3H), 2.11 (s, 3H), 1.77-1.42 (m, 4H).
2-020: δ7.25-7.09 (m, 2H), 6.98-6.89 (m, 1H), 6.30-5.94 (m, 3H), 4.01-3.82 (m, 6H), 3.71-3.58 (m, 2H) , 3.40-3.25 (m, 2H), 2.97 (s, 3H), 2.53 (s, 3H), 2.12 (s, 3H), 1.78-1.44 (m, 4H).
2-022: δ8.85-8.54 (m, 1H), 8.32-8.25 (m, 1H), 7.24-7.08 (m, 2H), 6.96-6.89 (m, 1H), 6.12-5.97 (m, 1H) , 3.99-3.84 (m, 1H), 3.90 (s, 3H), 3.80-3.58 (m, 2H), 3.47 (s, 3H), 3.43-3.21 (m, 2H), 2.57-2.45 (m, 3H) , 2.12 (s, 3H), 1.83-1.42 (m, 4H).
3-001: δ7.28-7.18 (m, 2H), 7.16-6.99 (m, 2H), 6.96-6.85 (m, 2H), 6.04-5.88 (m, 1H), 4.74-4.55 (m, 2H) , 4.50 (s, 2H), 3.98-3.80 (m, 4H), 3.74-3.51 (m, 2H), 3.40-3.18 (m, 5H), 3.00 (s, 3H), 2.48 (s, 3H), 1.80 -1.44 (m, 4H).
3-002: δ7.70-7.62 (m, 1H), 7.41-7.34 (m, 1H), 7.23-7.05 (m, 2H), 7.04-6.86 (m, 2H), 6.15-5.81 (m, 1H) , 4.63-4.42 (m, 2H), 4.05-3.80 (m, 4H), 3.79-3.55 (m, 2H), 3.50-3.10 (m, 8H), 2.55-2.37 (m, 3H), 1.82-1.12 ( m, 4H).
3-003: δ8.86-8.51 (m, 1H), 8.33-8.23 (m, 1H), 7.28-7.04 (m, 2H), 6.97-6.85 (m, 1H), 6.16-5.90 (m, 1H) , 4.60-4.44 (m, 2H), 4.02-3.80 (m, 4H), 3.80-3.54 (m, 2H), 3.50-3.10 (m, 8H), 2.51-2.37 (m, 3H), 1.85-1.39 ( m, 4H).
3-004: δ7.28-7.18 (m, 2H), 7.17-7.07 (m, 1H), 7.03-6.88 (m, 2H), 6.13-6.06 (m, 1H), 4.58-4.47 (m, 2H) , 4.55-3.83 (m, 4H), 3.80-3.62 (m, 2H), 3.45-3.27 (m, 7H), 2.51-2.43 (m, 3H), 1.82-1.21 (m, 13H).
3-005: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.11-5.95 (m, 1H), 4.60-4.44 (m, 2H) , 4.05-3.75 (m, 6H), 3.75-3.57 (m, 2H), 3.43-3.24 (m, 8H), 2.52-2.42 (m, 3H), 2.08-1.80 (m, 1H), 1.80-1.47 ( m, 4H), 1.04-0.76 (m, 6H).
3-006: δ7.28-7.21 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.13-5.88 (m, 1H), 4.59-4.46 (m, 2H) , 4.02-3.76 (m, 9H), 3.76-3.57 (m, 2H), 3.42-3.26 (m, 5H), 3.01-2.92 (m, 3H), 2.53-2.45 (m, 3H), 2.10-2.02 ( m, 3H), 1.83-1.47 (m, 4H).
3-007: δ7.28-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.30-6.21 (m, 1H), 6.12-5.99 (m, 2H) , 4.54-4.49 (m, 2H), 3.98-3.83 (m, 6H), 3.73-3.57 (m, 2H), 3.40-3.26 (m, 5H), 3.03-2.92 (m, 3H), 2.53-2.43 ( m, 3H), 1.83-1.46 (m, 4H).
3-008: δ7.23-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.12-5.87 (m, 1H), 4.63-4.46 (m, 2H), 4.06-3.86 (m, 4H) , 3.79-3.51 (m, 5H), 3.42-3.21 (m, 8H), 2.52-2.41 (m, 3H), 2.12-1.96 (m, 3H), 1.82-1.44 (m, 4H).
3-009: δ7.82-7.72 (m, 1H), 7.29-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.07-5.92 (m, 1H), 4.58-4.40 (m, 4H) , 3.97-3.83 (m, 4H), 3.72-3.55 (m, 2H), 3.40-3.23 (m, 5H), 3.03-2.94 (m, 3H), 2.53-2.44 (m, 3H), 1.79-1.44 ( m, 4H).
3-010: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.88 (m, 1H), 6.12-5.93 (m, 1H), 4.59-4.45 (m, 2H) , 4.03-3.83 (m, 6H), 3.74-3.60 (m, 2H), 3.44-3.23 (m, 8H), 2.51-2.43 (m, 3H), 1.83-1.44 (m, 4H), 1.04-0.75 ( m, 9H).
3-014: δ8.13-7.23 (m, 5H), 7.23-7.06 (m, 2H), 6.97-6.87 (m, 1H), 6.23-5.75 (m, 1H), 4.63-4.39 (m, 2H) , 4.04-3.79 (m, 4H), 3.77-3.54 (m, 2H), 3.47-3.15 (m, 8H), 2.55-2.36 (m, 3H), 1.86-1.31 (m, 4H).
3-015: δ8.15-7.81 (m, 1H), 7.24-7.17 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.86 (m, 1H), 6.12-5.91 (m, 1H) , 4.57-4.41 (m, 2H), 3.99-3.81 (m, 4H), 3.79-3.54 (m, 2H), 3.50-3.20 (m, 8H), 2.50-2.40 (m, 3H), 1.83-1.40 ( m, 4H).
3-016: δ8.17-8.07 (m, 1H), 7.23-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.16-5.84 (m, 1H), 4.57-4.43 (m, 2H) , 4.00-3.84 (m, 4H), 3.79-3.53 (m, 2H), 3.51-3.21 (m, 8H), 2.53-2.39 (m, 3H), 1.82-0.98 (m, 13H).
3-017: δ7.51-7.45 (m, 1H), 7.23-7.06 (m, 2H), 6.95-6.86 (m, 1H), 6.69-6.62 (m, 1H), 6.15-5.83 (m, 1H) , 4.62-4.43 (m, 2H), 4.04-3.78 (m, 4H), 3.78-3.56 (m, 2H), 3.46-3.11 (m, 8H), 2.56-2.35 (m, 6H), 1.81-1.29 ( m, 4H).
3-018: δ7.50-7.42 (m, 1H), 7.22-7.08 (m, 2H), 6.97-6.88 (m, 1H), 6.88-6.81 (m, 1H), 6.13-5.79 (m, 1H) , 4.60-4.46 (m, 2H), 4.03-3.82 (m, 4H), 3.80-3.56 (m, 2H), 3.49-3.12 (m, 8H), 2.54-2.42 (m, 3H), 1.83-1.34 ( m, 4H).
3-019: δ7.27-7.05 (m, 2H), 6.96-6.87 (m, 1H), 6.14-5.89 (m, 1H), 4.57-4.46 (m, 2H), 3.98-3.86 (m, 4H) , 3.77-3.60 (m, 2H), 3.48-3.17 (m, 8H), 2.72-2.08 (m, 4H), 2.06-1.01 (m, 14H).
3-020: δ7.27-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.14-5.88 (m, 1H), 4.60-4.45 (m, 2H), 4.00-3.86 (m, 4H) , 3.76-3.60 (m, 2H), 3.50-3.21 (m, 8H), 3.14-2.52 (m, 1H), 2.52-2.41 (m, 3H), 2.08-1.36 (m, 12H).
3-021: δ7.28-7.05 (m, 2H), 6.96-6.86 (m, 1H), 6.18-5.92 (m, 1H), 4.59-4.44 (m, 2H), 4.04-3.84 (m, 4H) , 3.77-3.60 (m, 2H), 3.52-3.21 (m, 8H), 2.74-2.06 (m, 4H), 1.88-1.36 (m, 8H), 1.10-0.77 (m, 6H).
3-022: δ7.26-7.18 (m, 1H), 7.16-7.07 (m, 1H), 6.96-6.88 (m, 1H), 6.15-5.86 (m, 2H), 4.58-4.41 (m, 2H) , 4.10-4.01 (m, 1H), 3.99-2.98 (m, 15H), 2.53-2.43 (m, 3H), 1.81-1.41 (m, 4H).
3-023: δ7.26-7.18 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 6.12-5.95 (m, 1H), 4.86-4.62 (m, 1H) , 4.60-4.45 (m, 2H), 4.07-3.22 (m, 14H), 2.54-2.42 (m, 3H), 2.00-1.10 (m, 14H).
3-024: δ7.27-7.19 (m, 2H), 7.15-7.00 (m, 2H), 6.95-6.87 (m, 2H), 6.07-5.89 (m, 1H), 4.73-4.49 (m, 4H) , 3.97-3.80 (m, 4H), 3.72-3.45 (m, 4H), 3.39-3.21 (m, 2H), 3.07-2.92 (m, 3H), 2.55-2.39 (m, 3H), 1.78-1.42 ( m, 4H), 1.30-1.13 (m, 3H).
3-025: δ7.27-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.10-5.94 (m, 1H), 4.65-4.49 (m, 2H), 4.05-3.46 (m, 10H) , 3.42-3.25 (m, 5H), 2.51-2.42 (m, 3H), 2.07-1.81 (m, 1H), 1.80-1.47 (m, 4H), 1.30-1.17 (m, 3H), 1.02-0.75 ( m, 6H).
3-026: δ7.68-7.61 (m, 1H), 7.36-7.30 (m, 1H), 7.21-7.08 (m, 2H), 6.98-6.87 (m, 2H), 6.11-5.72 (m, 1H) , 4.62-4.45 (m, 2H), 3.99-3.76 (m, 4H), 3.76-3.19 (m, 11H), 3.11-2.77 (m, 2H), 2.53-2.42 (m, 3H), 1.73-1.18 ( m, 4H).
3-027: δ7.73-7.64 (m, 1H), 7.52-6.81 (m, 5H), 5.76-5.25 (m, 1H), 4.63-4.47 (m, 2H), 4.34-4.07 (m, 1H) , 3.90-3.79 (m, 4H), 3.54-3.32 (m, 6H), 2.87-2.45 (m, 6H), 1.33-1.10 (m, 3H).
3-028: δ7.40-6.74 (m, 5H), 6.14-5.78 (m, 1H), 4.63-4.43 (m, 2H), 4.03-2.89 (m, 17H), 2.57-2.39 (m, 6H) , 1.72-1.21 (m, 4H).
3-029: δ8.87-7.90 (m, 2H), 7.25-7.06 (m, 2H), 6.96-6.86 (m, 1H), 6.11-5.88 (m, 1H), 4.61-4.44 (m, 2H) , 4.01-2.98 (m, 17H), 2.55-2.39 (m, 3H), 1.75-1.16 (m, 4H).
3-030: δ8.90-7.26 (m, 3H), 7.19-7.02 (m, 2H), 6.92-6.82 (m, 1H), 5.69-5.29 (m, 1H), 4.61-4.44 (m, 2H) , 4.35-4.16 (m, 1H), 3.93-3.76 (m, 3H), 3.54-3.31 (m, 6H), 2.87-2.30 (m, 6H), 1.39-1.16 (m, 3H).
3-031: δ8.12-7.07 (m, 7H), 6.96-6.86 (m, 1H), 6.13-5.75 (m, 1H), 4.61-4.38 (m, 2H), 4.04-2.91 (m, 17H) , 2.54-2.35 (m, 3H), 1.72-1.21 (m, 4H).
3-032: δ7.25-7.17 (m, 2H), 7.15-7.06 (m, 1H), 7.05-6.99 (m, 1H), 6.94-6.84 (m, 2H), 6.06-5.87 (m, 1H) , 4.74-4.41 (m, 4H), 3.97-3.82 (m, 4H), 3.69-3.55 (m, 3H), 3.45-3.07 (m, 7H), 3.04-2.95 (m, 3H), 2.53-2.41 ( m, 3H), 1.72-1.41 (m, 4H).
3-034: δ7.25-7.17 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.28-6.19 (m, 1H), 6.11-5.95 (m, 2H) , 4.65-4.43 (m, 2H), 4.00-3.81 (m, 6H), 3.65-3.55 (m, 3H), 3.50-3.10 (m, 7H), 3.00-2.92 (m, 3H), 2.53-2.43 ( m, 3H), 1.73-1.44 (m, 4H).
3-035: δ7.85-7.47 (m, 1H), 7.22-7.02 (m, 2H), 6.93-6.83 (m, 1H), 6.45-5.94 (m, 2H), 5.59-5.44 (m, 1H) , 4.57-4.45 (m, 2H), 4.35-4.22 (m, 1H), 4.06-3.78 (m, 5H), 3.45-3.33 (m, 3H), 3.10-2.95 (m, 3H), 2.95-2.78 ( m, 3H), 2.55-2.39 (m, 3H), 1.41-1.30 (m, 3H).
3-036: δ7.80-7.71 (m, 1H), 7.27-7.06 (m, 4H), 7.04-6.87 (m, 2H), 6.09-5.88 (m, 1H), 4.59-4.39 (m, 4H) , 3.99-3.82 (m, 4H), 3.66-3.56 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.94 (m, 3H), 2.53-2.43 (m, 3H), 1.71-1.43 ( m, 4H).
3-037: δ7.24-7.06 (m, 2H), 6.95-6.87 (m, 1H), 6.05-5.92 (m, 1H), 4.59-4.43 (m, 2H), 4.06-3.86 (m, 6H) , 3.81-3.15 (m, 13H), 2.54-2.41 (m, 3H), 2.12-1.75 (m, 1H), 1.74-1.46 (m, 4H), 1.07-0.73 (m, 6H).
3-038: δ7.79-7.47 (m, 1H), 7.25-7.01 (m, 2H), 6.92-6.82 (m, 1H), 5.67-5.46 (m, 1H), 4.62-4.45 (m, 2H) , 4.35-4.21 (m, 1H), 4.06-3.69 (m, 5H), 3.48-3.25 (m, 6H), 2.90-2.73 (m, 3H), 2.55-2.37 (m, 3H), 2.14-1.74 ( m, 1H), 1.40-0.73 (m, 9H).
3-039: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.07-5.90 (m, 1H), 4.60-4.40 (m, 2H) , 4.00-3.76 (m, 9H), 3.66-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.00-2.89 (m, 3H), 2.56-2.44 (m, 3H), 2.09-2.01 ( m, 3H), 1.71-1.47 (m, 4H).
3-041: δ7.25-7.07 (m, 2H), 6.96-6.87 (m, 1H), 6.07-5.84 (m, 1H), 4.62-4.40 (m, 2H), 4.04-3.83 (m, 4H) , 3.73-2.92 (m, 16H), 2.52-2.43 (m, 3H), 2.12-1.95 (m, 3H), 1.78-1.39 (m, 4H).
3-042: δ7.76-7.52 (m, 1H), 7.22-7.00 (m, 2H), 6.92-6.83 (m, 1H), 5.72-5.25 (m, 1H), 4.62-4.45 (m, 2H) , 4.35-4.21 (m, 1H), 4.07-3.27 (m, 12H), 2.86-2.74 (m, 3H), 2.53-2.39 (m, 3H), 2.14-1.92 (m, 3H), 1.41-1.21 ( m, 3H).
3-043: δ7.25-7.07 (m, 2H), 7.02-6.87 (m, 2H), 6.10-5.93 (m, 1H), 4.58-4.41 (m, 2H), 4.04-3.11 (m, 17H) , 2.51-2.39 (m, 3H), 1.72-1.49 (m, 4H), 1.33-1.18 (m, 9H).
3-044: δ7.61-7.39 (m, 5H), 6.12-6.02 (m, 1H), 4.59-4.44 (m, 2H), 4.10-3.93 (m, 3H), 3.85-3.57 (m, 3H) , 3.56-3.07 (m, 10H), 2.55-2.39 (m, 3H), 2.10-1.78 (m, 1H), 1.77-1.46 (m, 4H), 1.06-0.75 (m, 6H).
3-045: δ7.58-7.35 (m, 5H), 5.49-5.23 (m, 1H), 4.64-4.43 (m, 2H), 4.20-3.65 (m, 3H), 3.45-3.16 (m, 6H) , 2.98-2.70 (m, 3H), 2.54-2.37 (m, 3H), 2.11-1.75 (m, 1H), 1.66-1.37 (m, 3H), 1.31-0.71 (m, 6H).
*Protons derived from NH were not observed.
3-046: δ7.62-7.54 (m, 2H), 7.50-7.38 (m, 3H), 6.14-6.04 (m, 1H), 4.60-4.44 (m, 2H), 4.12-3.75 (m, 3H) , 3.74-3.59 (m, 2H), 3.44-3.24 (m, 8H), 2.56-2.41 (m, 3H), 2.08-1.48 (m, 5H), 1.06-0.76 (m, 6H).
3-047: δ7.64-7.54 (m, 2H), 7.49-7.38 (m, 3H), 6.17-6.02 (m, 1H), 4.62-4.41 (m, 2H), 4.08-3.95 (m, 1H) , 3.93-3.75 (m, 5H), 3.66-3.58 (m, 3H), 3.50-3.28 (m, 5H), 3.27-3.10 (m, 2H), 3.00-2.87 (m, 3H), 2.55-2.40 ( m, 3H), 2.14-1.98 (m, 3H), 1.78-1.49 (m, 4H).
3-049: δ7.62-7.55 (m, 2H), 7.48-7.38 (m, 3H), 6.17-6.04 (m, 1H), 4.58-4.43 (m, 2H), 4.08-3.95 (m, 1H) , 3.92-3.72 (m, 5H), 3.72-3.58 (m, 2H), 3.39-3.26 (m, 5H), 3.02-2.88 (m, 3H), 2.51-2.45 (m, 3H), 2.09-2.01 ( m, 3H), 1.85-1.49 (m, 4H).
3-050: δ7.61-7.54 (m, 2H), 7.49-7.41 (m, 3H), 7.23-7.18 (m, 1H), 7.05-7.01 (m, 1H), 6.92-6.86 (m, 1H) , 6.13-6.01 (m, 1H), 4.73-4.55 (m, 2H), 4.55-4.43 (m, 2H), 4.04-3.93 (m, 1H), 3.70-3.56 (m, 3H), 3.51-3.32 ( m, 5H), 3.25-3.04 (m, 2H), 3.03-2.96 (m, 3H), 2.54-2.42 (m, 3H), 1.75-1.42 (m, 4H).
3-051: δ7.56-7.36 (m, 5H), 7.29-7.16 (m, 1H), 7.02-6.79 (m, 2H), 5.47-5.22 (m, 1H), 4.94-4.67 (m, 1H) , 4.57-3.71 (m, 4H), 3.44-3.25 (m, 3H), 3.14-2.72 (m, 6H), 2.52-2.35 (m, 3H), 1.48-0.72 (m, 3H).
*Protons derived from NH were not observed.
3-052: δ7.62-7.55 (m, 2H), 7.48-7.41 (m, 3H), 7.24-7.19 (m, 1H), 7.06-7.01 (m, 1H), 6.93-6.87 (m, 1H) , 6.10-6.06 (m, 1H), 4.73-4.55 (m, 2H), 4.51-4.46 (m, 2H), 4.07-3.93 (m, 1H), 3.72-3.56 (m, 2H), 3.39-3.20 ( m, 5H), 3.04-2.96 (m, 3H), 2.52-2.45 (m, 3H), 1.82-1.45 (m, 4H).
3-054: δ7.58-7.38 (m, 5H), 6.34-6.13 (m, 1H), 6.08-5.92 (m, 1H), 5.48-5.22 (m, 1H), 4.64-3.70 (m, 6H) , 3.43-3.28 (m, 3H), 3.02-2.74 (m, 6H), 2.54-2.39 (m, 3H), 1.48-0.97 (m, 3H).
3-055: δ7.68-7.38 (m, 5H), 6.33-5.98 (m, 3H), 4.60-4.43 (m, 2H), 4.19-3.83 (m, 3H), 3.76-3.61 (m, 2H) , 3.48-3.26 (m, 5H), 3.08-2.92 (m, 3H), 2.58-2.42 (m, 3H), 1.87-1.49 (m, 4H).
3-056: δ7.83-7.69 (m, 1H), 7.62-7.54 (m, 2H), 7.49-7.40 (m, 3H), 7.24-7.16 (m, 1H), 7.15-7.07 (m, 1H) , 7.04-6.94 (m, 1H), 6.15-6.02 (m, 1H), 4.57-4.40 (m, 4H), 4.07-3.94 (m, 1H), 3.65-3.57 (m, 3H), 3.48-3.28 ( m, 5H), 3.26-3.06 (m, 2H), 3.04-2.91 (m, 3H), 2.54-2.41 (m, 3H), 1.83-1.43 (m, 4H).
3-057: δ7.76-7.36 (m, 6H), 7.24-7.15 (m, 1H), 7.15-6.92 (m, 2H), 5.55-5.11 (m, 1H), 4.61-4.27 (m, 4H) , 4.07-3.77 (m, 1H), 3.42-3.26 (m, 3H), 3.05-2.79 (m, 6H), 2.52-2.37 (m, 3H), 1.47-0.85 (m, 3H).
*Protons derived from NH were not observed.
3-058: δ7.80-7.71 (m, 1H), 7.62-7.55 (m, 2H), 7.48-7.39 (m, 3H), 7.27-7.16 (m, 1H), 7.16-7.08 (m, 1H) , 7.04-6.95 (m, 1H), 6.17-6.04 (m, 1H), 4.58-4.41 (m, 4H), 4.08-3.96 (m, 1H), 3.71-3.56 (m, 2H), 3.43-3.21 ( m, 5H), 3.04-2.90 (m, 3H), 2.55-2.42 (m, 3H), 1.83-1.42 (m, 4H).
3-059: δ7.69-7.31 (m, 7H), 7.00-6.93 (m, 1H), 6.16-5.88 (m, 1H), 4.61-4.45 (m, 2H), 4.03-3.87 (m, 1H) , 3.75-2.65 (m, 13H), 2.55-2.40 (m, 3H), 1.82-1.30 (m, 4H).
3-061: δ7.68-7.36 (m, 7H), 7.03-6.97 (m, 1H), 6.17-5.90 (m, 1H), 4.59-4.45 (m, 2H), 4.06-3.92 (m, 1H) , 3.79-3.57 (m, 2H), 3.47-3.33 (m, 6H), 3.31-3.09 (m, 2H), 2.54-2.40 (m, 3H), 1.87-1.29 (m, 4H).
3-062: δ7.64-6.75 (m, 7H), 6.18-5.92 (m, 1H), 4.60-4.42 (m, 2H), 4.18-3.88 (m, 1H), 3.76-2.79 (m, 13H) , 2.57-2.40 (m, 6H), 1.81-1.20 (m, 4H).
3-064: δ7.64-6.75 (m, 7H), 6.19-5.95 (m, 1H), 4.60-4.42 (m, 2H), 4.17-3.91 (m, 1H), 3.78-3.58 (m, 2H) , 3.46-3.10 (m, 8H), 2.57-2.39 (m, 6H), 1.89-1.33 (m, 4H).
3-065: δ7.73-7.19 (m, 10H), 6.18-5.88 (m, 1H), 4.62-4.39 (m, 2H), 4.18-3.81 (m, 1H), 3.78-2.80 (m, 13H) , 2.57-2.41 (m, 3H), 1.81-1.17 (m, 4H).
3-067: δ7.71-7.22 (m, 10H), 6.19-5.89 (m, 1H), 4.60-4.42 (m, 2H), 4.03-3.82 (m, 1H), 3.76-3.54 (m, 2H) , 3.45-3.09 (m, 8H), 2.54-2.40 (m, 3H), 1.88-1.21 (m, 4H).
3-068: δ7.62-7.38 (m, 5H), 7.05-6.94 (m, 1H), 6.15-6.04 (m, 1H), 4.59-4.45 (m, 2H), 4.18-4.03 (m, 1H) , 3.86-3.11 (m, 13H), 2.52-2.41 (m, 3H), 1.81-1.46 (m, 4H), 1.33-1.19 (m, 9H).
3-069: δ7.57-7.33 (m, 5H), 7.10-6.95 (m, 1H), 5.53-5.12 (m, 1H), 4.66-4.42 (m, 2H), 4.18-3.87 (m, 1H) , 3.81-3.22 (m, 6H), 2.99-2.74 (m, 3H), 2.47-2.38 (m, 3H), 1.53-1.37 (m, 3H), 1.36-1.16 (m, 9H).
*Protons derived from NH were not observed.
3-070: δ7.62-7.39 (m, 5H), 6.13-5.96 (m, 1H), 4.59-4.45 (m, 2H), 4.10-2.93 (m, 17H), 2.54-2.40 (m, 3H) , 2.13-1.97 (m, 3H), 1.82-1.40 (m, 4H).
3-072: δ7.62-7.52 (m, 2H), 7.51-7.40 (m, 3H), 6.15-5.97 (m, 1H), 4.61-4.45 (m, 2H), 4.10-3.21 (m, 14H) , 2.54-2.40 (m, 3H), 2.13-1.97 (m, 3H), 1.86-1.47 (m, 4H).
3-073: δ8.95-7.35 (m, 7H), 6.17-6.02 (m, 1H), 4.61-4.44 (m, 2H), 4.16-2.89 (m, 14H), 2.54-2.39 (m, 3H) , 1.84-1.17 (m, 4H).
3-075: δ8.87-7.37 (m, 7H), 6.18-6.06 (m, 1H), 4.59-4.44 (m, 2H), 4.17-3.97 (m, 1H), 3.87-3.15 (m, 10H) , 2.52-2.40 (m, 3H), 1.87-1.42 (m, 4H).
3-076: δ7.51-6.86 (m, 7H), 5.94-5.80 (m, 1H), 4.73-4.57 (m, 2H), 4.54-4.44 (m, 2H), 3.97-3.87 (m, 4H) , 3.70-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.05-2.97 (m, 3H), 2.53-2.43 (m, 3H), 1.76-1.44 (m, 4H).
3-077: δ7.51-7.37 (m, 2H), 7.22-7.16 (m, 1H), 7.06-6.85 (m, 4H), 5.92-5.81 (m, 1H), 4.73-4.45 (m, 4H) , 3.95-3.83 (m, 4H), 3.65-3.57 (m, 3H), 3.46-3.07 (m, 7H), 3.05-2.95 (m, 3H), 2.53-2.42 (m, 3H), 1.71-1.18 ( m, 4H).
3-078: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 6.30-6.21 (m, 1H), 6.12-6.00 (m, 1H), 5.94-5.80 (m, 1H) , 4.57-4.47 (m, 2H), 4.01-3.25 (m, 13H), 3.03-2.94 (m, 3H), 2.54-2.44 (m, 3H), 1.78-1.47 (m, 4H).
3-079: δ7.50-7.38 (m, 2H), 7.07-6.93 (m, 2H), 6.28-6.19 (m, 1H), 6.11-5.99 (m, 1H), 5.86-5.78 (m, 1H) , 4.56-4.48 (m, 2H), 4.00-3.83 (m, 6H), 3.65-3.58 (m, 3H), 3.46-3.10 (m, 7H), 3.01-2.93 (m, 3H), 2.53-2.43 ( m, 3H), 1.70-1.18 (m, 4H).
3-080: δ7.84-6.93 (m, 8H), 5.95-5.86 (m, 1H), 4.59-4.40 (m, 4H), 4.00-3.85 (m, 4H), 3.70-3.53 (m, 2H) , 3.41-3.22 (m, 5H), 3.04-2.94 (m, 3H), 2.53-2.45 (m, 3H), 1.78-1.44 (m, 4H).
3-081: δ7.82-6.92 (m, 8H), 5.95-5.83 (m, 1H), 4.57-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.64-3.56 (m, 2H) , 3.45-3.10 (m, 8H), 3.01-2.92 (m, 3H), 2.52-2.44 (m, 3H), 1.70-1.21 (m, 4H).
3-082: δ7.52-7.39 (m, 2H), 7.33-7.28 (m, 1H), 7.26-7.20 (m, 2H), 7.06-6.94 (m, 2H), 5.95-5.85 (m, 1H) , 4.55-4.41 (m, 4H), 3.99-3.85 (m, 4H), 3.72-3.54 (m, 2H), 3.39-3.21 (m, 5H), 3.04-2.95 (m, 3H), 2.52-2.45 ( m, 3H), 1.78-1.47 (m, 4H).
3-083: δ7.51-7.38 (m, 2H), 7.31-7.26 (m, 1H), 7.25-7.18 (m, 2H), 7.05-6.93 (m, 2H), 5.90-5.81 (m, 1H) , 4.54-4.38 (m, 4H), 3.96-3.84 (m, 4H), 3.66-3.57 (m, 3H), 3.44-3.09 (m, 7H), 3.01-2.92 (m, 3H), 2.52-2.42 ( m, 3H), 1.70-1.17 (m, 4H).
3-084: δ8.86-7.38 (m, 4H), 7.05-6.92 (m, 2H), 5.99-5.82 (m, 1H), 4.58-4.45 (m, 2H), 4.02-3.18 (m, 17H) , 2.51-2.37 (m, 3H), 1.80-1.37 (m, 4H).
3-085: δ7.52-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.95-5.87 (m, 1H), 4.56-4.48 (m, 2H), 3.98-3.77 (m, 9H) , 3.71-3.55 (m, 2H), 3.39-3.24 (m, 5H), 2.99-2.91 (m, 3H), 2.53-2.44 (m, 3H), 2.09-2.02 (m, 3H), 1.78-1.48 ( m, 4H).
3-086: δ7.51-7.37 (m, 2H), 7.05-6.93 (m, 2H), 5.87-5.84 (m, 1H), 4.55-4.48 (m, 2H), 3.97-3.75 (m, 9H) , 3.74-3.59 (m, 5H), 3.43-3.13 (m, 5H), 2.97-2.91 (m, 3H), 2.51-2.44 (m, 3H), 2.07-2.02 (m, 3H), 1.66-1.50 ( m, 4H).
3-087: δ7.49-7.37 (m, 2H), 7.08-6.93 (m, 2H), 5.95-5.82 (m, 1H), 4.60-4.45 (m, 2H), 4.05-3.22 (m, 16H) , 2.53-2.43 (m, 3H), 2.06-1.80 (m, 1H), 1.78-1.47 (m, 4H), 1.03-0.75 (m, 6H).
3-088: δ7.49-7.37 (m, 2H), 7.06-6.93 (m, 2H), 5.90-5.80 (m, 1H), 4.61-4.46 (m, 2H), 4.06-3.14 (m, 19H) , 2.53-2.42 (m, 3H), 2.08-1.73 (m, 1H), 1.68-1.16 (m, 4H), 1.03-0.73 (m, 6H).
3-089: δ7.71-7.65 (m, 1H), 7.50-7.36 (m, 3H), 7.06-6.93 (m, 3H), 6.02-5.70 (m, 1H), 4.60-4.46 (m, 2H) , 4.03-3.13 (m, 14H), 2.53-2.42 (m, 3H), 1.78-1.30 (m, 4H).
3-090: δ7.93-6.91 (m, 7H), 5.99-5.52 (m, 1H), 4.62-4.47 (m, 2H), 4.01-2.79 (m, 17H), 2.53-2.41 (m, 3H) , 1.69-1.14 (m, 4H).
3-091: δ7.54-6.79 (m, 6H), 6.04-5.71 (m, 1H), 4.60-4.44 (m, 2H), 4.03-3.81 (m, 4H), 3.75-3.57 (m, 2H) , 3.45-3.15 (m, 8H), 2.59-2.39 (m, 6H), 1.79-1.16 (m, 4H).
3-092: δ7.55-6.76 (m, 6H), 6.02-5.68 (m, 1H), 4.63-4.45 (m, 2H), 4.04-2.91 (m, 17H), 2.61-2.39 (m, 6H) , 1.69-1.13 (m, 4H).
3-093: δ7.62-7.06 (m, 6H), 6.59-6.40 (m, 1H), 6.23-6.00 (m, 1H), 4.60-4.46 (m, 2H), 4.04-3.91 (m, 1H) , 3.81-3.14 (m, 10H), 2.53-2.41 (m, 3H), 1.87-1.47 (m, 4H).
3-094: δ8.73-7.20 (m, 8H), 6.26-6.03 (m, 1H), 4.61-4.43 (m, 2H), 4.11-3.91 (m, 1H), 3.79-3.17 (m, 10H) , 2.53-2.37 (m, 3H), 1.88-1.20 (m, 4H).
3-095: δ7.65-7.20 (m, 4H), 6.21-6.06 (m, 1H), 4.63-4.45 (m, 2H), 4.10-3.99 (m, 1H), 3.78-3.65 (m, 2H) , 3.48-3.22 (m, 8H), 2.55-2.45 (m, 3H), 2.45-1.95 (m, 2H), 1.88-1.47 (m, 4H), 1.08-0.83 (m, 7H).
3-096: δ8.77-7.20 (m, 7H), 6.21-5.87 (m, 1H), 4.61-4.43 (m, 2H), 4.04-3.90 (m, 1H), 3.78-3.63 (m, 2H) , 3.44-3.15 (m, 8H), 2.52-2.40 (m, 3H), 1.82-1.34 (m, 4H).
3-097: δ8.00-7.34 (m, 6H), 6.21-6.06 (m, 1H), 4.60-4.46 (m, 2H), 4.09-3.94 (m, 1H), 3.82-3.58 (m, 2H) , 3.53-3.16 (m, 8H), 2.51-2.39 (m, 3H), 1.88-1.39 (m, 4H).
3-099: δ7.61-7.27 (m, 5H), 6.66-6.26 (m, 1H), 6.19-5.95 (m, 1H), 4.56-4.46 (m, 2H), 4.10-3.90 (m, 4H) , 3.79-3.65 (m, 2H), 3.51-3.16 (m, 8H), 2.52-2.39 (m, 3H), 1.88-1.13 (m, 4H).
3-100: δ7.91-7.32 (m, 6H), 6.22-5.95 (m, 1H), 4.57-4.47 (m, 2H), 4.03-3.13 (m, 14H), 2.82-2.42 (m, 3H) , 1.87-1.17 (m, 4H).
3-102: δ7.88-6.88 (m, 6H), 6.25-5.99 (m, 1H), 4.60-4.44 (m, 2H), 4.11-3.89 (m, 1H), 3.79-3.62 (m, 2H) , 3.49-3.16 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.31 (m, 4H).
3-103: δ8.70-7.36 (m, 7H), 6.25-5.99 (m, 1H), 4.60-4.45 (m, 2H), 4.10-3.93 (m, 1H), 3.80-3.18 (m, 10H) , 2.52-2.36 (m, 3H), 1.88-1.33 (m, 4H).
3-104: δ8.08-8.02 (m, 1H), 7.75-7.67 (m, 1H), 7.61-7.23 (m, 5H), 6.23-6.05 (m, 1H), 4.58-4.49 (m, 2H) , 4.08-3.92 (m, 1H), 3.78-3.18 (m, 10H), 2.52-2.38 (m, 3H), 1.86-1.33 (m, 4H).
3-105: δ7.29-6.81 (m, 6H), 6.01-5.89 (m, 1H), 4.73-4.39 (m, 4H), 4.02-3.68 (m, 7H), 3.40-3.29 (m, 3H) , 3.05-2.92 (m, 3H), 2.53-2.42 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H).
3-106: δ7.31-7.05 (m, 5H), 6.97-6.87 (m, 1H), 6.01-5.89 (m, 1H), 4.55-4.37 (m, 4H), 4.02-3.68 (m, 7H) , 3.39-3.29 (m, 3H), 3.01-2.89 (m, 3H), 2.52-2.43 (m, 3H), 2.41-1.88 (m, 4H), 1.81-1.51 (m, 4H).
3-107: δ7.59-7.50 (m, 2H), 7.35-7.17 (m, 4H), 7.17-7.06 (m, 1H), 6.97-6.87 (m, 1H), 6.04-5.91 (m, 1H) , 4.55-4.34 (m, 4H), 4.02-3.68 (m, 7H), 3.39-3.29 (m, 3H), 2.96-2.86 (m, 3H), 2.52-2.45 (m, 3H), 2.45-1.88 ( m, 4H), 1.83-1.51 (m, 4H).
3-108: δ7.82-7.72 (m, 1H), 7.30-6.88 (m, 6H), 6.04-5.93 (m, 1H), 4.57-4.39 (m, 4H), 4.02-3.60 (m, 7H) , 3.40-3.30 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.89 (m, 4H), 1.84-1.53 (m, 4H).
3-109: δ7.27-7.20 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.89 (m, 1H), 6.29-6.20 (m, 1H), 6.11-5.89 (m, 2H) , 4.56-4.43 (m, 2H), 4.04-3.73 (m, 9H), 3.40-3.31 (m, 3H), 3.00-2.92 (m, 3H), 2.52-2.43 (m, 3H), 2.43-1.92 ( m, 4H), 1.85-1.54 (m, 4H).
3-110: δ7.28-7.18 (m, 1H), 7.18-7.07 (m, 1H), 6.96-6.86 (m, 1H), 6.05-5.89 (m, 1H), 4.59-4.44 (m, 2H) , 4.07-3.95 (m, 1H), 3.94-3.69 (m, 6H), 3.58-3.13 (m, 6H), 2.50-2.40 (m, 3H), 2.41-1.91 (m, 4H), 1.89-1.14 ( m, 13H).
3-111: δ7.62-7.20 (m, 7H), 7.01-6.90 (m, 1H), 6.19-6.08 (m, 1H), 4.63-4.36 (m, 4H), 4.02-3.92 (m, 1H) , 3.66-3.56 (m, 3H), 3.47-3.03 (m, 7H), 2.98-2.87 (m, 3H), 2.54-2.43 (m, 3H), 1.74-1.37 (m, 4H).
3-112: δ7.61-6.95 (m, 8H), 6.17-6.07 (m, 1H), 4.61-4.33 (m, 4H), 4.02-3.91 (m, 1H), 3.67-3.56 (m, 3H) , 3.46-3.05 (m, 7H), 2.96-2.87 (m, 3H), 2.53-2.44 (m, 3H), 1.73-1.41 (m, 4H).
3-113: δ7.61-7.08 (m, 8H), 6.20-6.09 (m, 1H), 4.56-4.34 (m, 4H), 4.01-3.89 (m, 1H), 3.69-3.56 (m, 3H) , 3.47-3.30 (m, 5H), 3.25-3.09 (m, 2H), 2.99-2.87 (m, 3H), 2.54-2.42 (m, 6H), 1.75-1.42 (m, 4H).
3-114: δ7.75-7.35 (m, 5H), 7.25-7.17 (m, 1H), 6.98-6.91 (m, 1H), 6.85-6.80 (m, 1H), 6.21-6.09 (m, 1H) , 4.57-4.34 (m, 4H), 4.02-3.92 (m, 1H), 3.85-3.73 (m, 3H), 3.67-3.56 (m, 3H), 3.46-3.29 (m, 5H), 3.26-3.07 ( m, 2H), 3.03-2.93 (m, 3H), 2.55-2.43 (m, 3H), 1.73-1.42 (m, 4H).
3-115: δ7.60-7.17 (m, 5H), 6.89-6.82 (m, 2H), 6.21-6.10 (m, 1H), 4.57-4.39 (m, 4H), 4.03-3.93 (m, 1H) , 3.68-3.57 (m, 3H), 3.53-3.31 (m, 5H), 3.26-3.10 (m, 2H), 3.10-3.00 (m, 3H), 2.51-2.36 (m, 3H), 1.77-1.45 ( m, 4H).
3-116: δ7.61-7.35 (m, 4H), 7.13-7.09 (m, 1H), 6.79-6.74 (m, 1H), 6.19-6.10 (m, 1H), 4.68-4.43 (m, 4H) , 4.01-3.91 (m, 1H), 3.68-3.58 (m, 3H), 3.48-3.30 (m, 5H), 3.26-3.06 (m, 2H), 3.02-2.93 (m, 3H), 2.52-2.43 ( m, 3H), 2.31-2.21 (m, 3H), 1.74-1.42 (m, 4H).
3-117: δ8.90-7.03 (m, 6H), 6.20-6.10 (m, 1H), 4.89-4.47 (m, 4H), 4.05-3.92 (m, 1H), 3.66-3.58 (m, 3H) , 3.47-3.29 (m, 5H), 3.25-3.01 (m, 5H), 2.52-2.45 (m, 3H), 1.76-1.42 (m, 4H).
3-118: δ7.61-7.35 (m, 5H), 6.13-6.04 (m, 1H), 4.64-4.46 (m, 4H), 4.04-3.93 (m, 1H), 3.68-3.58 (m, 3H) , 3.47-3.30 (m, 5H), 3.26-3.07 (m, 2H), 3.03-2.91 (m, 3H), 2.53-2.41 (m, 3H), 1.74-1.44 (m, 4H).
3-119: δ8.46-7.21 (m, 7H), 6.15-6.03 (m, 1H), 4.77-4.36 (m, 4H), 4.04-3.93 (m, 1H), 3.67-3.56 (m, 3H) , 3.45-3.06 (m, 7H), 2.98-2.89 (m, 3H), 2.52-2.41 (m, 3H), 1.74-1.44 (m, 4H).
3-120: δ7.61-7.36 (m, 4H), 6.20-6.08 (m, 1H), 4.59-4.46 (m, 2H), 4.05-3.93 (m, 1H), 3.69-3.56 (m, 3H) , 3.52-3.32 (m, 5H), 3.24-3.08 (m, 4H), 3.07-2.97 (m, 3H), 2.54-2.43 (m, 3H), 1.79-1.48 (m, 4H), 1.04-0.89 ( m, 1H), 0.46-0.32 (m, 2H), 0.15-0.06 (m, 2H).
3-121: δ7.61-7.36 (m, 4H), 6.20-5.94 (m, 3H), 4.57-4.46 (m, 2H), 4.18-4.08 (m, 2H), 4.04-3.94 (m, 1H) , 3.67-3.61 (m, 3H), 3.49-3.32 (m, 5H), 3.27-3.10 (m, 2H), 3.07-3.00 (m, 3H), 2.51-2.42 (m, 3H), 1.76-1.45 ( m, 4H).
3-122: δ8.97-7.33 (m, 7H), 7.29-7.20 (m, 1H), 6.22-5.91 (m, 1H), 4.56-4.43 (m, 2H), 4.09-3.86 (m, 1H) , 3.78-3.58 (m, 2H), 3.46-3.14 (m, 8H), 2.54-2.39 (m, 3H), 1.89-1.29 (m, 4H).
3-125: δ7.90-7.83 (m, 2H), 7.37-7.20 (m, 4H), 7.15-7.05 (m, 1H), 6.94-6.87 (m, 1H), 5.98-5.85 (m, 1H) , 4.64-4.34 (m, 4H), 4.00-3.71 (m, 10H), 3.40-3.28 (m, 3H), 3.08-2.98 (m, 3H), 2.49-2.41 (m, 3H), 2.39-1.86 ( m, 4H), 1.82-1.53 (m, 4H).
3-126: δ7.28-7.21 (m, 1H), 7.16-7.07 (m, 1H), 6.95-6.87 (m, 1H), 6.03-5.91 (m, 1H), 4.55-4.42 (m, 2H) , 4.02-3.70 (m, 12H), 3.39-3.30 (m, 3H), 2.96-2.89 (m, 3H), 2.52-2.44 (m, 3H), 2.44-1.91 (m, 7H), 1.84-1.51 ( m, 4H).
3-128: δ7.86-7.06 (m, 5H), 6.96-6.87 (m, 1H), 6.09-5.78 (m, 1H), 4.57-4.41 (m, 2H), 4.07-3.72 (m, 7H) , 3.50-3.32 (m, 6H), 2.57-1.88 (m, 7H), 1.87-1.31 (m, 4H).
3-129: δ8.86-8.25 (m, 2H), 7.24-7.18 (m, 1H), 7.16-7.08 (m, 1H), 6.96-6.87 (m, 1H), 6.08-5.91 (m, 1H) , 4.59-4.43 (m, 2H), 4.06-3.73 (m, 7H), 3.50-3.32 (m, 6H), 2.50-1.88 (m, 7H), 1.78-1.50 (m, 4H).
3-130: δ7.27-7.05 (m, 2H), 6.97-6.86 (m, 1H), 6.10-5.90 (m, 1H), 4.58-4.43 (m, 2H), 4.06-3.94 (m, 1H) , 3.94-3.86 (m, 3H), 3.79-3.72 (m, 3H), 3.50-3.20 (m, 6H), 2.71-2.55 (m, 1H), 2.51-1.91 (m, 7H), 1.86-1.33 ( m, 8H), 1.11-0.77 (m, 6H).
3-131: δ7.72-7.64 (m, 1H), 7.56-7.40 (m, 2H), 7.35-7.07 (m, 4H), 6.96-6.86 (m, 1H), 6.11-5.76 (m, 1H) , 4.58-4.38 (m, 2H), 4.18-3.70 (m, 7H), 3.42-3.28 (m, 6H), 2.54-1.39 (m, 11H).
3-132: δ7.27-7.18 (m, 1H), 7.18-7.04 (m, 1H), 6.97-6.86 (m, 1H), 6.05-5.90 (m, 1H), 4.59-4.41 (m, 2H) , 4.06-3.61 (m, 9H), 3.45-3.25 (m, 6H), 2.70-1.52 (m, 12H), 1.06-0.69 (m, 6H).
3-133: δ7.27-7.19 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.02-5.97 (m, 1H), 4.55-4.47 (m, 2H) , 4.03-3.86 (m, 4H), 3.78-3.70 (m, 3H), 3.39-3.31 (m, 3H), 3.28-3.17 (m, 2H), 3.02-2.92 (m, 3H), 2.52-2.45 ( m, 3H), 2.45-2.10 (m, 4H), 2.07-0.78 (m, 13H).
3-134: δ7.29-7.22 (m, 1H), 7.15-7.05 (m, 1H), 6.94-6.86 (m, 1H), 6.04-5.98 (m, 1H), 4.55-4.47 (m, 2H) , 4.04-3.72 (m, 9H), 3.58-3.52 (m, 3H), 3.39-3.31 (m, 3H), 3.03-2.95 (m, 3H), 2.51-2.44 (m, 3H), 2.42-1.89 ( m, 4H), 1.87-1.57 (m, 4H), 1.34-1.07 (m, 9H).
3-135: δ7.25-7.06 (m, 2H), 6.96-6.87 (m, 1H), 6.06-5.85 (m, 1H), 4.60-4.44 (m, 2H), 4.05-2.97 (m, 16H) , 2.53-1.92 (m, 10H), 1.81-1.55 (m, 4H).
3-136: δ8.15-6.90 (m, 9H), 6.00-5.65 (m, 1H), 4.57-4.38 (m, 2H), 4.05-3.13 (m, 14H), 2.55-2.35 (m, 3H) , 1.82-1.30 (m, 4H).
3-137: δ8.14-6.90 (m, 9H), 5.97-5.62 (m, 1H), 4.58-4.43 (m, 2H), 4.03-2.87 (m, 17H), 2.54-2.37 (m, 3H) , 1.70-1.20 (m, 4H).
3-138: δ7.26-7.18 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 6.08-5.90 (m, 1H), 4.59-4.42 (m, 2H) , 4.05-3.19 (m, 17H), 2.53-2.42 (m, 3H), 2.41-1.92 (m, 4H), 1.87-1.53 (m, 8H).
3-139: δ7.25-7.19 (m, 1H), 7.16-7.06 (m, 1H), 6.95-6.87 (m, 1H), 5.99-5.93 (m, 1H), 4.56-4.47 (m, 2H) , 4.04-3.94 (m, 1H), 3.93-3.85 (m, 3H), 3.78-3.71 (m, 3H), 3.41-3.33 (m,3H), 3.33-3.21 (m, 4H), 3.21-3.13 ( m, 3H), 2.51-1.91 (m, 7H), 1.79-1.41 (m, 10H).
3-140: δ7.25-7.17 (m, 1H), 7.17-7.06 (m, 1H), 6.96-6.87 (m, 1H), 5.94-5.88 (m, 1H), 4.55-4.47 (m, 2H) , 4.28-4.14 (m, 1H), 4.04-3.92 (m, 1H), 3.92-3.85 (m, 3H), 3.78-3.70 (m, 3H), 3.41-3.33 (m,3H), 3.17-3.08 ( m, 3H), 2.65-2.56 (m, 3H), 2.51-1.91 (m, 7H), 1.78-1.57 (m, 4H), 1.41-0.99 (m, 6H).
4-001: δ7.40-6.80 (m, 3H), 6.09 (s, 1H), 6.02 (s, 1H), 4.30-3.20 (m, 17H), 2.95 (s, 3H), 2.55 (s, 3H) ), 2.10-2.00 (m, 3H), 1.80-1.50 (m, 4H).
4-002: δ7.70-6.85 (m, 6H), 6.09 (s, 1H), 5.81 (s, 1H), 4.25-3.10 (m, 12H), 2.54 (s, 3H), 2.03 (s, 3H) ), 1.85-1.15 (m, 4H).
4-003: δ7.25-7.19 (m, 2H), 7.16-7.07 (m, 1H), 7.07-7.01 (m, 1H), 6.95-6.87 (m, 2H), 6.05-5.87 (m, 1H) , 4.73-4.51 (m, 2H), 3.98-3.82 (m, 4H), 3.71-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.06-2.93 (m, 3H), 2.65-2.51 ( m, 3H), 2.37-2.23 (m, 3H), 1.79-1.44 (m, 4H).
4-004: δ7.25-7.18 (m, 2H), 7.18-7.08 (m, 1H), 7.07-7.00 (m, 1H), 6.95-6.87 (m, 2H), 5.95-5.89 (m, 1H) , 4.72-4.50 (m, 2H), 3.98-3.82 (m, 4H), 3.74-3.54 (m, 2H), 3.39-3.21 (m, 2H), 3.05-2.96 (m, 3H), 2.91-2.83 ( m, 3H), 2.66-2.56 (m, 3H), 1.78-1.43 (m, 4H).
4-006: δ7.80-6.80 (m, 6H), 6.00-5.20 (m, 2H), 3.90-3.20 (m, 15H), 2.50-2.40 (m, 3H), 1.80-1.50 (m, 4H) .
4-007: δ7.35-6.80 (m, 6H), 6.00-5.90 (m, 2H), 4.72-4.50 (m, 2H), 4.00-3.20 (m, 12H), 3.10-2.90 (m, 3H) , 2.55-2.40 (m, 3H), 1.85-1.50 (m, 4H).
4-011: δ7.78-7.68 (m, 1H), 7.64-7.55 (m, 1H), 7.50-6.90 (m, 6H), 6.17-6.09 (m, 1H), 4.54-4.41 (m, 2H) , 4.34-4.24 (m, 2H), 4.05-3.93 (m, 1H), 3.75-3.61 (m, 2H), 3.51-3.40 (m, 2H), 3.39-3.25 (m, 2H), 3.03-2.95 ( m, 3H), 2.92-2.83 (m, 3H), 1.84-1.70 (m, 2H), 1.63-1.46 (m, 2H).
――――――――――――――――――――――――――――――――――
[Test example]
Next, the usefulness of the compound of the present invention as a pest control agent according to one embodiment will be specifically described in the following test examples, but the present invention is not limited thereto. In the test examples, "RH" represents relative humidity, and for example, the description "humidity 100% RH" means that the relative humidity is 100%.
試験薬液の調製
一態様に係る本発明化合物を、乳化白試料(ソルポール(登録商標)3005XL(東邦化学工業社製)、N-メチルピロリドン、及びソルベッソ(登録商標)200(エクソンモービル社製)[1:5:28(重量比)の混合物]中に溶解し、1質量%、5質量%又は20質量%濃度の乳剤を調製した。この乳剤を試験薬液として以下の試験例1~9に供試した。 Preparation of Test Drug Solution A compound of the present invention according to one embodiment was added to an emulsified white sample (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry Co., Ltd.), N-methylpyrrolidone, and Solvesso (registered trademark) 200 (manufactured by ExxonMobil) [ 1:5:28 (weight ratio)] to prepare emulsions with a concentration of 1% by mass, 5% by mass or 20% by mass.This emulsion is used as a test drug solution in Test Examples 1 to 9 below. tried.
一態様に係る本発明化合物を、乳化白試料(ソルポール(登録商標)3005XL(東邦化学工業社製)、N-メチルピロリドン、及びソルベッソ(登録商標)200(エクソンモービル社製)[1:5:28(重量比)の混合物]中に溶解し、1質量%、5質量%又は20質量%濃度の乳剤を調製した。この乳剤を試験薬液として以下の試験例1~9に供試した。 Preparation of Test Drug Solution A compound of the present invention according to one embodiment was added to an emulsified white sample (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry Co., Ltd.), N-methylpyrrolidone, and Solvesso (registered trademark) 200 (manufactured by ExxonMobil) [ 1:5:28 (weight ratio)] to prepare emulsions with a concentration of 1% by mass, 5% by mass or 20% by mass.This emulsion is used as a test drug solution in Test Examples 1 to 9 below. tried.
試験例1 コムギふ枯病防除効果試験
90cm3のプラスチックポットに、コムギ(品種:ハルユタカ)を植え、1.3葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、コムギふ枯病菌(Septoria nodorum)の分生胞子懸濁液を、コムギに噴霧接種し、温度20℃、湿度100%RHの接種箱内に2日間入れた。その後、空調温室(温度20℃、湿度80%RH)に置き、8日間保持した。形成された病斑の接種葉に占める割合を測定し、下記の計算式に従い、防除価を算出した。 Test Example 1 Wheat wilt disease control effect test Plant wheat (cultivar: Haruyutaka) in a 90 cm 3 plastic pot, and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water at the 1.3 leaf stage. processed. One day after spraying, the wheat was spray-inoculated with a conidial spore suspension of Septoria nodorum and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature 20° C., humidity 80% RH) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated according to the following formula.
90cm3のプラスチックポットに、コムギ(品種:ハルユタカ)を植え、1.3葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、コムギふ枯病菌(Septoria nodorum)の分生胞子懸濁液を、コムギに噴霧接種し、温度20℃、湿度100%RHの接種箱内に2日間入れた。その後、空調温室(温度20℃、湿度80%RH)に置き、8日間保持した。形成された病斑の接種葉に占める割合を測定し、下記の計算式に従い、防除価を算出した。 Test Example 1 Wheat wilt disease control effect test Plant wheat (cultivar: Haruyutaka) in a 90 cm 3 plastic pot, and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water at the 1.3 leaf stage. processed. One day after spraying, the wheat was spray-inoculated with a conidial spore suspension of Septoria nodorum and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature 20° C., humidity 80% RH) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated according to the following formula.
防除価=〔1-(処理区病斑面積率/無処理区病斑面積率)〕×100
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。 Control value = [1-(lesion area rate in treated area/lesion area rate in untreated area)] x 100
As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。 Control value = [1-(lesion area rate in treated area/lesion area rate in untreated area)] x 100
As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
化合物;No.2-005、2-011~2-014、2-018~2-022、3-107、3-120。
Compound; No. 2-005, 2-011 to 2-014, 2-018 to 2-022, 3-107, 3-120.
試験例2 コムギ赤さび病防除効果試験
90cm3のプラスチックポットに、コムギ(品種:農林61号)を植え、1.3葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、コムギ赤さび病菌(Puccinia recondita)の胞子懸濁液を、コムギに噴霧接種し、温度20℃、湿度100%RHの接種箱内に1日間入れた。その後、空調温室(温度20℃、湿度60%RH)に置き、8日間保持した。形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 2 Wheat leaf rust prevention effect test Wheat (variety: Norin No. 61) was planted in a 90 cm 3 plastic pot, and at the 1.3 leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was added. Treated by spraying. One day after spraying, wheat was spray-inoculated with a spore suspension of Puccinia recondita and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 1 day. After that, it was placed in an air-conditioned greenhouse (temperature 20° C., humidity 60% RH) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
90cm3のプラスチックポットに、コムギ(品種:農林61号)を植え、1.3葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、コムギ赤さび病菌(Puccinia recondita)の胞子懸濁液を、コムギに噴霧接種し、温度20℃、湿度100%RHの接種箱内に1日間入れた。その後、空調温室(温度20℃、湿度60%RH)に置き、8日間保持した。形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 2 Wheat leaf rust prevention effect test Wheat (variety: Norin No. 61) was planted in a 90 cm 3 plastic pot, and at the 1.3 leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was added. Treated by spraying. One day after spraying, wheat was spray-inoculated with a spore suspension of Puccinia recondita and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 1 day. After that, it was placed in an air-conditioned greenhouse (temperature 20° C., humidity 60% RH) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-001、2-002。
Compound; No. 1-001, 2-002.
試験例3 コムギうどんこ病防除効果試験
90cm3のプラスチックポットに、コムギ(品種:農林61号)を植え、1.3葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、空調温室(温度20℃、湿度70%RH)にコムギを置き、コムギうどんこ病菌(Blumeria graminis)の分生胞子を、コムギに接種した。その後、7日間保持し、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 3 Wheat Powdery Mildew Control Effect Test Wheat (variety: Norin No. 61) was planted in a 90 cm 3 plastic pot, and at the 1.3 leaf stage, the test chemical was diluted with water to 500 ppm. 5 ml was sprayed. One day after spraying, the wheat was placed in an air-conditioned greenhouse (temperature 20° C., humidity 70% RH) and inoculated with conidia of wheat powdery mildew (Blumeria graminis). Thereafter, the leaves were maintained for 7 days, and the ratio of the formed lesions to the inoculated leaves was measured.
90cm3のプラスチックポットに、コムギ(品種:農林61号)を植え、1.3葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、空調温室(温度20℃、湿度70%RH)にコムギを置き、コムギうどんこ病菌(Blumeria graminis)の分生胞子を、コムギに接種した。その後、7日間保持し、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 3 Wheat Powdery Mildew Control Effect Test Wheat (variety: Norin No. 61) was planted in a 90 cm 3 plastic pot, and at the 1.3 leaf stage, the test chemical was diluted with water to 500 ppm. 5 ml was sprayed. One day after spraying, the wheat was placed in an air-conditioned greenhouse (temperature 20° C., humidity 70% RH) and inoculated with conidia of wheat powdery mildew (Blumeria graminis). Thereafter, the leaves were maintained for 7 days, and the ratio of the formed lesions to the inoculated leaves was measured.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-001、1-003~1-014、1-016~1-031、1-033~1-040、1-042~1-050、1-054~1-059、1-062~1-066、2-002、2-004~2-008、2-011~2-015、2-017~2-022、3-001~3-041、3-043~3-051、3-053~3-059、3-061、3-062、3-064、3-065、3-067、3-068、3-070、3-072、3-073、3-075~3-086、4-001~4-006。
Compound; No. 1-001, 1-003 to 1-014, 1-016 to 1-031, 1-033 to 1-040, 1-042 to 1-050, 1-054 to 1-059, 1-062 to 1- 066, 2-002, 2-004-2-008, 2-011-2-015, 2-017-2-022, 3-001-3-041, 3-043-3-051, 3-053- 3-059, 3-061, 3-062, 3-064, 3-065, 3-067, 3-068, 3-070, 3-072, 3-073, 3-075 to 3-086, 4- 001 to 4-006.
試験例4 トマトうどんこ病防除効果試験
90cm3のプラスチックポットに、トマト(品種:桃太郎)を植え、2葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。風乾後、トマトを空調温室(温度20℃、湿度70%RH)に置き、トマトうどんこ病菌(Leveillula taurica)の分生胞子懸濁液を、噴霧接種した。14日間置いた後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 4 Tomato Powdery Mildew Control Effect Test Tomatoes (variety: Momotaro) were planted in a 90 cm 3 plastic pot, and at the two-leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was sprayed. . After air-drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying a conidia suspension of tomato powdery mildew (Leveillula taurica). After leaving for 14 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
90cm3のプラスチックポットに、トマト(品種:桃太郎)を植え、2葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。風乾後、トマトを空調温室(温度20℃、湿度70%RH)に置き、トマトうどんこ病菌(Leveillula taurica)の分生胞子懸濁液を、噴霧接種した。14日間置いた後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 4 Tomato Powdery Mildew Control Effect Test Tomatoes (variety: Momotaro) were planted in a 90 cm 3 plastic pot, and at the two-leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was sprayed. . After air-drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying a conidia suspension of tomato powdery mildew (Leveillula taurica). After leaving for 14 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-067、1-069~1-077、1-079~1-097、1-099~1-109、3-087~3-102、3-104~3-114、3-116、3-117、3-120~3-137、4-011。
Compound; No. 1-067, 1-069 to 1-077, 1-079 to 1-097, 1-099 to 1-109, 3-087 to 3-102, 3-104 to 3-114, 3-116, 3- 117, 3-120 to 3-137, 4-011.
試験例5 キュウリ灰色かび病防除効果試験
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理し、風乾した。その後、処理葉を切り取り、プラスチック容器に入れた。キュウリ灰色かび病菌(Botrytis cinerea)の分生胞子懸濁液と溶解させたPDA培地とを、1:1(体積比)の割合で混合し、処理葉に30μlずつ滴下接種した。接種後、20℃、多湿(湿度100%RH)下に3日間置いた。その後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 5 Cucumber gray mold control effect test A cucumber (cultivar: Frost-free ground) is planted in a 90 cm 3 plastic pot, and 5 ml of a chemical solution prepared by diluting the test chemical solution with water to 500 ppm is sprayed during the cotyledon stage. Treated and air dried. The treated leaves were then cut and placed in a plastic container. A conidia suspension of Botrytis cinerea and dissolved PDA medium were mixed at a ratio of 1:1 (volume ratio), and 30 μl of the mixture was inoculated dropwise onto the treated leaves. After inoculation, the plants were placed at 20° C. and high humidity (100% RH) for 3 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理し、風乾した。その後、処理葉を切り取り、プラスチック容器に入れた。キュウリ灰色かび病菌(Botrytis cinerea)の分生胞子懸濁液と溶解させたPDA培地とを、1:1(体積比)の割合で混合し、処理葉に30μlずつ滴下接種した。接種後、20℃、多湿(湿度100%RH)下に3日間置いた。その後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 5 Cucumber gray mold control effect test A cucumber (cultivar: Frost-free ground) is planted in a 90 cm 3 plastic pot, and 5 ml of a chemical solution prepared by diluting the test chemical solution with water to 500 ppm is sprayed during the cotyledon stage. Treated and air dried. The treated leaves were then cut and placed in a plastic container. A conidia suspension of Botrytis cinerea and dissolved PDA medium were mixed at a ratio of 1:1 (volume ratio), and 30 μl of the mixture was inoculated dropwise onto the treated leaves. After inoculation, the plants were placed at 20° C. and high humidity (100% RH) for 3 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-001~1-067、1-069~1-091、1-093~1-109、2-002~2-022、3-001~3-026、3-028、3-029、3-031~3-034、3-036~3-041、3-043~3-053、3-055~3-141、4-001~4-003、4-006~4-011。
Compound; No. 1-001 to 1-067, 1-069 to 1-091, 1-093 to 1-109, 2-002 to 2-022, 3-001 to 3-026, 3-028, 3-029, 3- 031-3-034, 3-036-3-041, 3-043-3-053, 3-055-3-141, 4-001-4-003, 4-006-4-011.
試験例6 キュウリ菌核病防除効果試験
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液5mlを散布処理し、風乾した。その後、処理葉をプラスチックコンテナーに入れた。予めPDA培地で培養したキュウリ菌核病(Sclerotinia sclerotiorum)の含菌寒天片(直径5mm)を、薬剤処理したキュウリの子葉に接種した。接種後、プラスチックコンテナーをビニールで覆い加湿(湿度100%RH)し、20℃に2日間置いた。その後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 6 Cucumber Sclerotinia Prevention Effect Test Plant cucumbers (variety: frost-free ground) in a 90 cm 3 plastic pot, and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water during the cotyledon stage. and air dried. The treated leaves were then placed in a plastic container. Sclerotinia sclerotiorum-containing agar pieces (5 mm in diameter) previously cultured in PDA medium were inoculated onto the drug-treated cucumber cotyledons. After inoculation, the plastic container was covered with vinyl, humidified (humidity 100% RH), and placed at 20° C. for 2 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液5mlを散布処理し、風乾した。その後、処理葉をプラスチックコンテナーに入れた。予めPDA培地で培養したキュウリ菌核病(Sclerotinia sclerotiorum)の含菌寒天片(直径5mm)を、薬剤処理したキュウリの子葉に接種した。接種後、プラスチックコンテナーをビニールで覆い加湿(湿度100%RH)し、20℃に2日間置いた。その後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 6 Cucumber Sclerotinia Prevention Effect Test Plant cucumbers (variety: frost-free ground) in a 90 cm 3 plastic pot, and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water during the cotyledon stage. and air dried. The treated leaves were then placed in a plastic container. Sclerotinia sclerotiorum-containing agar pieces (5 mm in diameter) previously cultured in PDA medium were inoculated onto the drug-treated cucumber cotyledons. After inoculation, the plastic container was covered with vinyl, humidified (humidity 100% RH), and placed at 20° C. for 2 days. Thereafter, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-001、1-013~1-028、2-002、2-016~2-021、3-001~3-008、4-001。
Compound; No. 1-001, 1-013 to 1-028, 2-002, 2-016 to 2-021, 3-001 to 3-008, 4-001.
試験例7 キュウリうどんこ病防除効果試験
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。風乾後、キュウリを空調温室(温度20℃、湿度70%RH)に置き、キュウリうどんこ病菌(Erysiphe polygoni)の分生胞子懸濁液を、噴霧接種した。9日間置いた後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 7 Cucumber Powdery Mildew Control Effect Test Plant cucumbers (cultivar: Frost-free ground) in a plastic pot of 90 cm 3 , and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water during the cotyledon stage. processed. After air-drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying with a conidia suspension of cucumber powdery mildew (Erysiphe polygoni). After leaving for 9 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。風乾後、キュウリを空調温室(温度20℃、湿度70%RH)に置き、キュウリうどんこ病菌(Erysiphe polygoni)の分生胞子懸濁液を、噴霧接種した。9日間置いた後、形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 7 Cucumber Powdery Mildew Control Effect Test Plant cucumbers (cultivar: Frost-free ground) in a plastic pot of 90 cm 3 , and spray 5 ml of a chemical solution prepared at 500 ppm by diluting the test chemical solution with water during the cotyledon stage. processed. After air-drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying with a conidia suspension of cucumber powdery mildew (Erysiphe polygoni). After leaving for 9 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-001~1-109、2-002~2-022、3-001~3-095、3-097~3-117、3-119~3-137、4-001~4-009、4-011。
Compound; No. 1-001 to 1-109, 2-002 to 2-022, 3-001 to 3-095, 3-097 to 3-117, 3-119 to 3-137, 4-001 to 4-009, 4- 011.
試験例8 キュウリ炭疽病防除効果試験
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、キュウリ炭疽病菌(Colletotrichum lagenarium)の分生胞子懸濁液を、キュウリに噴霧接種し、温度25℃、湿度100%RHの接種箱内に2日間入れた。その後、空調温室(温度23℃、湿度60%RH)に置き、7日間保持した。形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 8 Cucumber anthracnose control effect test A cucumber (cultivar: Frost-free ground) is planted in a 90 cm 3 plastic pot, and at the cotyledon stage, 5 ml of a chemical solution prepared by diluting the test chemical solution with water to 500 ppm is sprayed. did. One day after spraying, cucumbers were spray-inoculated with a conidial spore suspension of Colletotrichum lagenarium and placed in an inoculation box at a temperature of 25° C. and a humidity of 100% RH for 2 days. Then, it was placed in an air-conditioned greenhouse (temperature 23° C., humidity 60% RH) and held for 7 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
90cm3のプラスチックポットに、キュウリ(品種:霜知らず地這)を植え、子葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、キュウリ炭疽病菌(Colletotrichum lagenarium)の分生胞子懸濁液を、キュウリに噴霧接種し、温度25℃、湿度100%RHの接種箱内に2日間入れた。その後、空調温室(温度23℃、湿度60%RH)に置き、7日間保持した。形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 8 Cucumber anthracnose control effect test A cucumber (cultivar: Frost-free ground) is planted in a 90 cm 3 plastic pot, and at the cotyledon stage, 5 ml of a chemical solution prepared by diluting the test chemical solution with water to 500 ppm is sprayed. did. One day after spraying, cucumbers were spray-inoculated with a conidial spore suspension of Colletotrichum lagenarium and placed in an inoculation box at a temperature of 25° C. and a humidity of 100% RH for 2 days. Then, it was placed in an air-conditioned greenhouse (temperature 23° C., humidity 60% RH) and held for 7 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-001、1-003、1-005~1-015、1-017~1-051、1-053~1-059、1-062~1-091、1-093~1-109、2-002~2-009、2-011~2-015、2-017~2-022、3-001~3-005、3-007、3-009~3-015、3-017~3-026、3-028、3-029、3-031~3-037、3-040、3-041、3-043、3-044、3-046、3-047、3-049~3-053、3-056、3-058、3-059、3-061~3-065、3-068、3-070、3-073、3-075~3-137、4-001~4-006、4-011。
Compound; No. 1-001, 1-003, 1-005 to 1-015, 1-017 to 1-051, 1-053 to 1-059, 1-062 to 1-091, 1-093 to 1-109, 2- 002 to 2-009, 2-011 to 2-015, 2-017 to 2-022, 3-001 to 3-005, 3-007, 3-009 to 3-015, 3-017 to 3-026, 3-028, 3-029, 3-031 to 3-037, 3-040, 3-041, 3-043, 3-044, 3-046, 3-047, 3-049 to 3-053, 3- 056, 3-058, 3-059, 3-061 to 3-065, 3-068, 3-070, 3-073, 3-075 to 3-137, 4-001 to 4-006, 4-011.
試験例9 ダイズさび病防除効果試験
90cm3のプラスチックポットに、ダイズ(品種:エンレイ)を植え、単葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、ダイズさび病菌(Phakopsora pachyrhizi)の分生胞子懸濁液を、ダイズに噴霧接種し、温度20℃、湿度100%RHの接種箱内に2日間入れた。その後、空調温室(温度20℃、湿度60%RH)に置き、10日間保持した。形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 9 Soybean Rust Prevention Effect Test Soybeans (variety: Enrei) were planted in a 90 cm 3 plastic pot, and at the single leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was sprayed. One day after spraying, the soybeans were spray-inoculated with a conidia suspension of Phakopsora pachyrhizi and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature: 20°C, humidity: 60% RH) and held for 10 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
90cm3のプラスチックポットに、ダイズ(品種:エンレイ)を植え、単葉期に、試験薬液を水で希釈して500ppmに調製した薬液を、5ml散布処理した。散布1日後、ダイズさび病菌(Phakopsora pachyrhizi)の分生胞子懸濁液を、ダイズに噴霧接種し、温度20℃、湿度100%RHの接種箱内に2日間入れた。その後、空調温室(温度20℃、湿度60%RH)に置き、10日間保持した。形成された病斑の接種葉に占める割合を測定し、試験例1と同様の計算式から防除価を算出した。 Test Example 9 Soybean Rust Prevention Effect Test Soybeans (variety: Enrei) were planted in a 90 cm 3 plastic pot, and at the single leaf stage, 5 ml of a test chemical diluted with water to a concentration of 500 ppm was sprayed. One day after spraying, the soybeans were spray-inoculated with a conidia suspension of Phakopsora pachyrhizi and placed in an inoculation box at a temperature of 20° C. and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature: 20°C, humidity: 60% RH) and held for 10 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.
その結果、供試した化合物の内、以下の化合物が防除価70%以上を示した。
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
化合物;No.1-001~1-016、1-018、1-022、1-025~1-50、1-052、1-054~1-059、1-063~1-067、1-069~1-109、2-003~2-005、2-007~2-009、2-011~2-022、3-002~3-005、3-007、3-010~3-020、3-024~3-026、3-029、3-031、3-032、3-036、3-038~3-041、3-043、3-044、3-046~3-050、3-052、3-053、3-056、3-059、3-061、3-062、3-064、3-067、3-070、3-071、3-073~3-137、4-002~4-005、4-007~4-008、4-010、4-011。
Compound; No. 1-001 to 1-016, 1-018, 1-022, 1-025 to 1-50, 1-052, 1-054 to 1-059, 1-063 to 1-067, 1-069 to 1- 109, 2-003-2-005, 2-007-2-009, 2-011-2-022, 3-002-3-005, 3-007, 3-010-3-020, 3-024- 3-026, 3-029, 3-031, 3-032, 3-036, 3-038 to 3-041, 3-043, 3-044, 3-046 to 3-050, 3-052, 3- 053, 3-056, 3-059, 3-061, 3-062, 3-064, 3-067, 3-070, 3-071, 3-073 to 3-137, 4-002 to 4-005, 4-007 to 4-008, 4-010, 4-011.
また、試験例10及び11では以下の方法で試験薬液を調製した。まず、一態様に係る本発明化合物をジメチルスルホキシド中に溶解し、1%濃度の溶液を調製した。次いで、蒸留水を加えて所定の濃度(10ppm)に希釈した。
In addition, in Test Examples 10 and 11, test drug solutions were prepared by the following method. First, a compound of the present invention according to one aspect was dissolved in dimethylsulfoxide to prepare a 1% concentration solution. Distilled water was then added to dilute to a given concentration (10 ppm).
試験例10 クロコウジカビ菌に対する抗菌活性試験
96ウェルプレートに一態様に係る本発明化合物の試験薬液を、各ウェル当たり10μlずつ添加し、その上からクロコウジカビ菌(Aspergillus niger)培養上清(胞子10個/3μl)ポテト・デキストロースを90μlずつ加えた。プレートは暗黒条件下、25℃にて静置した。薬剤添加2日後の菌叢面積率(%)を判定し、無処理区に対するefficacy(%)を下式により算出した。
efficacy(%)=〔1-(処理区菌叢面積率/無処理区菌叢面積率)〕×100
その結果、供試した化合物の内、下記の化合物が70%以上のefficacy(%)を示した。 Test Example 10 Antibacterial activity test against Aspergillus niger To a 96-well plate, 10 μl of the test drug solution of the compound of the present invention according to one embodiment was added to each well, and then Aspergillus niger culture supernatant (10 spores) was added to each well. (pieces/3 μl) Potato dextrose was added in 90 μl portions. Plates were left at 25° C. in the dark. Two days after addition of the drug, the bacterial flora area ratio (%) was determined, and the efficiency (%) relative to the untreated plot was calculated by the following formula.
Efficacy (%) = [1-(treated area bacterial flora area / untreated area bacterial flora area ratio)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 70% or more.
96ウェルプレートに一態様に係る本発明化合物の試験薬液を、各ウェル当たり10μlずつ添加し、その上からクロコウジカビ菌(Aspergillus niger)培養上清(胞子10個/3μl)ポテト・デキストロースを90μlずつ加えた。プレートは暗黒条件下、25℃にて静置した。薬剤添加2日後の菌叢面積率(%)を判定し、無処理区に対するefficacy(%)を下式により算出した。
efficacy(%)=〔1-(処理区菌叢面積率/無処理区菌叢面積率)〕×100
その結果、供試した化合物の内、下記の化合物が70%以上のefficacy(%)を示した。 Test Example 10 Antibacterial activity test against Aspergillus niger To a 96-well plate, 10 μl of the test drug solution of the compound of the present invention according to one embodiment was added to each well, and then Aspergillus niger culture supernatant (10 spores) was added to each well. (pieces/3 μl) Potato dextrose was added in 90 μl portions. Plates were left at 25° C. in the dark. Two days after addition of the drug, the bacterial flora area ratio (%) was determined, and the efficiency (%) relative to the untreated plot was calculated by the following formula.
Efficacy (%) = [1-(treated area bacterial flora area / untreated area bacterial flora area ratio)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 70% or more.
化合物;No.1-015~1-028、3-001~3-007、3-009~3-015、3-017~3-023、4-001。
Compound; No. 1-015 to 1-028, 3-001 to 3-007, 3-009 to 3-015, 3-017 to 3-023, 4-001.
試験例11 Candida albicansに対する抗菌活性試験
96ウェルプレートに一態様に係る本発明化合物の試験薬液を、各ウェル当たり10μlずつ添加し、その上からCandida albicans 培養上清(5×103cell/ml)ポテト・デキストロースを90μlずつ加えた。プレートは暗黒条件下、25℃にて静置した。薬剤添加2日後の菌叢面積率(%)を判定し、無処理区に対するefficacy(%)を下式により算出した。
efficacy(%)=〔1-(処理区菌叢面積率/無処理区菌叢面積率)〕×100
その結果、供試した化合物の内、下記の化合物が70%以上のefficacy(%)を示した。 Test Example 11 Antibacterial activity test against Candida albicans To a 96-well plate, 10 μl of the test drug solution of the compound of the present invention according to one aspect was added to each well, and Candida albicans culture supernatant (5×10 3 cells/ml) was added thereon. Potato dextrose was added in 90 μl portions. Plates were left at 25° C. in the dark. Two days after addition of the drug, the bacterial flora area ratio (%) was determined, and the efficiency (%) relative to the untreated plot was calculated by the following formula.
Efficacy (%) = [1-(treated area bacterial flora area / untreated area bacterial flora area ratio)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 70% or more.
96ウェルプレートに一態様に係る本発明化合物の試験薬液を、各ウェル当たり10μlずつ添加し、その上からCandida albicans 培養上清(5×103cell/ml)ポテト・デキストロースを90μlずつ加えた。プレートは暗黒条件下、25℃にて静置した。薬剤添加2日後の菌叢面積率(%)を判定し、無処理区に対するefficacy(%)を下式により算出した。
efficacy(%)=〔1-(処理区菌叢面積率/無処理区菌叢面積率)〕×100
その結果、供試した化合物の内、下記の化合物が70%以上のefficacy(%)を示した。 Test Example 11 Antibacterial activity test against Candida albicans To a 96-well plate, 10 μl of the test drug solution of the compound of the present invention according to one aspect was added to each well, and Candida albicans culture supernatant (5×10 3 cells/ml) was added thereon. Potato dextrose was added in 90 μl portions. Plates were left at 25° C. in the dark. Two days after addition of the drug, the bacterial flora area ratio (%) was determined, and the efficiency (%) relative to the untreated plot was calculated by the following formula.
Efficacy (%) = [1-(treated area bacterial flora area / untreated area bacterial flora area ratio)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 70% or more.
化合物;No.1-015~1-020、1-022~1-028、3-001、3-009、3-010、3-013~3-015、3-017~3-019、3-021、3-023、4-001。
Compound; No. 1-015 to 1-020, 1-022 to 1-028, 3-001, 3-009, 3-010, 3-013 to 3-015, 3-017 to 3-019, 3-021, 3- 023, 4-001.
本発明に係るチエノウラシル化合物は、優れた有害生物防除活性、特に殺菌活性を示し、且つ、ホ乳動物、魚類及び有用昆虫等の非標的生物に対して、ほとんど悪影響の無い、極めて有用な化合物である。
The thienouracil compound according to the present invention is an extremely useful compound that exhibits excellent pesticidal activity, particularly fungicidal activity, and has almost no adverse effects on non-target organisms such as mammals, fish, and useful insects. be.
Claims (11)
- 式(1):
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-C(O)R9、フェニル、(Z1)mによって置換されたフェニル、G-1~G-64又はG-65を表し、
G-1~G-65は、それぞれ下記の構造式で表される構造を表し、
F-31及びF-34は、下記の構造式で表される構造を表し、
L-1~L-6、L-8及びL-9は、下記の構造式で表される構造を表し、
Rbは、水素原子を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル、E-1~E-90、L-5、L-6、L-8又はL-9を表し、
R7は、水素原子、C1~C6アルキル、C3~C6シクロアルキル、トリ(C1~C6アルキル)シリル又は-C(O)R10を表し、
E-1~E-90は、それぞれ下記の構造式で表される構造を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、C1~C6アルキルアミノ、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、(Z1)mによって置換されたフェニル、G-1~G-65、E-1~E-89又はE-90を表し、
R10は、フェニルを表し、
R11は、-OH、C1~C6アルコキシ、C1~C6アルキルアミノカルボニル、-C(O)N(ORa)Ra2、E-3、E-6、E-7又はE-38を表し、
R12は、水素原子又はC1~C6アルキルを表し、
R13は、水素原子又はC1~C6アルキルを表し、
R14は、C1~C6アルキル又はC1~C6アルキルカルボニルを表し、
R15は、シアノ、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルキル、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R17は、水素原子、C1~C6アルキル又は-CH2C(O)Raを表し、
R18は、水素原子、C1~C6アルキル又はフェニルを表し、
Raは、C1~C6アルキルを表し、
Ra1は、水素原子、C1~C6アルキル、フェニル又は(Z1)mによって置換されたフェニルを表し、
Ra2は、C1~C6アルキルを表し、
Zは、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
m1が2、3、4又は5の整数を示す場合には、各々のZは互いに同一であっても、又は互いに相異なっても良く、
Z1は、シアノ、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
mが2、3、4又は5の整数を示す場合には、各々のZ1は互いに同一であっても、又は互いに相異なっても良く、
Z9は、ハロゲン原子又はC1~C6アルキルを表し、
Z10は、C1~C6アルキルを表し、
Zaは、シアノ、C1~C6アルキル、C1~C6アルコキシ、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル、-CH2CN又は-C(O)C(O)ORaを表し、
Z9との関係において、p2が2の整数を表し、p3が2又は3の整数を表し、p4が、2、3又は4の整数を表し、p5が2、3、4又は5の整数を表し、p7が2、3、4、5、6又は7の整数を表す場合には、各々のZ9は互いに同一であっても、又は互いに相異なっても良く、
Z10との関係において、p3が2又は3の整数を表し、p5が2、3、4又は5の整数を表し、p6が2、3、4、5又は6の整数を表し、p7が、2、3、4、5、6又は7の整数を表し、p8が2、3、4、5、6、7又は8の整数を表し、p9が2、3、4、5、6、7、8又は9の整数を表し、p10が2、3、4、5、6、7、8、9又は10の整数を示す場合には、各々のZ10は互いに同一であっても、又は互いに相異なっても良く、
m及びm1は、1、2、3、4又は5の整数を表し、
rは0、1又は2の整数を表し、
p1は、0又は1の整数を表し、
p2は、0、1又は2の整数を表し、
p3は、0、1、2又は3の整数を表し、
p4は、0、1、2、3又は4の整数を表し、
p5は、0、1、2、3、4又は5の整数を表し、
p6は、0、1、2、3、4、5又は6の整数を表し、
p7は、0、1、2、3、4、5、6又は7の整数を表し、
p8は、0、1、2、3、4、5、6、7又は8の整数を表し、
p9は、0、1、2、3、4、5、6、7、8又は9の整数を表し、
p10は、0、1、2、3、4、5、6、7、8、9又は10の整数を表す。]
で表されるチエノウラシル化合物又はその塩。 Formula (1):
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 cycloalkoxycarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —C(O)R 9 , phenyl, phenyl substituted by (Z 1 ) m , G-1 to G-64 or represents G-65,
G-1 to G-65 each represent a structure represented by the following structural formula,
F-31 and F-34 represent structures represented by the following structural formulas,
L-1 to L-6, L-8 and L-9 represent structures represented by the following structural formulas,
R b represents a hydrogen atom,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 , E-1 to representing E-90, L-5, L-6, L-8 or L-9,
R 7 represents a hydrogen atom, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 6 alkyl)silyl or —C(O)R 10 ;
E-1 to E-90 each represent a structure represented by the following structural formula,
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkyl amino, di(C 1 -C 6 alkyl)amino, —C(=NOR a )R a1 , phenyl, phenyl substituted by (Z 1 ) m , G-1 to G-65, E-1 to E- 89 or E-90,
R 10 represents phenyl,
R 11 is —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylaminocarbonyl, —C(O)N(OR a )R a2 , E-3, E-6, E-7 or E- represents 38,
R 12 represents a hydrogen atom or C 1 -C 6 alkyl,
R 13 represents a hydrogen atom or C 1 -C 6 alkyl,
R 14 represents C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl,
R 15 represents cyano, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 17 represents a hydrogen atom, C 1 -C 6 alkyl or —CH 2 C(O)R a ,
R 18 represents a hydrogen atom, C 1 -C 6 alkyl or phenyl;
R a represents C 1 -C 6 alkyl,
R a1 represents a hydrogen atom, C 1 -C 6 alkyl, phenyl or phenyl substituted by (Z 1 ) m ;
R a2 represents C 1 -C 6 alkyl,
Z represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z may be the same or different;
Z 1 represents cyano, a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
when m represents an integer of 2, 3, 4 or 5, each Z 1 may be the same or different;
Z 9 represents a halogen atom or C 1 -C 6 alkyl,
Z 10 represents C 1 -C 6 alkyl,
Z a is cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 6 alkyl)aminocarbonyl, di(C 1 -C 6 alkyl)aminosulfonyl, —CH CN or —C ( O)C(O)OR a ,
In relation to Z9, p2 represents an integer of 2, p3 represents an integer of 2 or 3, p4 represents an integer of 2, 3 or 4, and p5 represents an integer of 2, 3, 4 or 5. and when p represents an integer of 2, 3, 4, 5, 6 or 7, each Z 9 may be the same as or different from each other,
In relation to Z 10 , p3 represents an integer of 2 or 3, p5 represents an integer of 2, 3, 4 or 5, p6 represents an integer of 2, 3, 4, 5 or 6, p7 is p8 represents an integer of 2, 3, 4, 5, 6 or 7, p8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, p9 represents an integer of 2, 3, 4, 5, 6, 7, When representing an integer of 8 or 9 and p10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z 10 may be identical to each other or relative to each other. can be different,
m and m represent an integer of 1, 2, 3, 4 or 5;
r represents an integer of 0, 1 or 2,
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p5 represents an integer of 0, 1, 2, 3, 4 or 5;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6;
p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7;
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
p9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
p10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; ]
A thienouracil compound represented by or a salt thereof. - R1は、C1~C6アルキルを表し、
R2は、水素原子、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6アルケニル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、C3~C6シクロアルコキシカルボニル、-C(O)R9又はフェニルを表し、
R3は、フェニル又は(Z)m1によって置換されたフェニルを表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、C3~C6シクロアルキル、R16によって置換されたC3~C6シクロアルキル、E-38、E-41、E-44、L-5又はL-6を表し、
R8は、C3~C6シクロアルキル、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-22、G-23又はG-53を表し、
R9は、C1~C6アルキル、C3~C6シクロアルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、ジ(C1~C6アルキル)アミノ、-C(=NORa)Ra1、フェニル、G-1、G-3、G-4、G-15~G-17、G-21、G-22、G-52、G-53、E-45又はE-76を表し、
R11は、C1~C6アルキルアミノカルボニル又は-C(O)N(ORa)Ra2を表し、
R15は、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル又はC1~C6アルキルスルホニルを表し、
R16は、C1~C6アルコキシ又はC1~C6アルコキシカルボニルを表し、
R18は、C1~C6アルキル又はフェニルを表し、
Ra1は、C1~C6アルキルを表し、
Z1は、ハロゲン原子、C1~C6アルキル又はC1~C6アルコキシを表し、
Zaは、C1~C6アルキル、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル、ジ(C1~C6アルキル)アミノカルボニル、ジ(C1~C6アルキル)アミノスルホニル又は-C(O)C(O)ORaを表し、
m及びm1は、1又は2の整数を表す、請求項1に記載のチエノウラシル化合物又はその塩。 R 1 represents C 1 -C 6 alkyl,
R 2 is a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, represents C 3 -C 6 cycloalkoxycarbonyl, —C(O)R 9 or phenyl,
R 3 represents phenyl or phenyl substituted by (Z) m1 ,
R 6 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted by R 16 , E-38, representing E-41, E-44, L-5 or L-6,
R 8 is C 3 -C 6 cycloalkyl, —C(═NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-22, G-23 or represents G-53,
R 9 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 6alkyl )amino, —C(=NOR a )R a1 , phenyl, G-1, G-3, G-4, G-15 to G-17, G-21, G-22, G-52, G -53, E-45 or E-76,
R 11 represents C 1 -C 6 alkylaminocarbonyl or —C(O)N(OR a )R a2 ,
R 15 represents C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkylsulfonyl;
R 16 represents C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
R 18 represents C 1 -C 6 alkyl or phenyl,
R a1 represents C 1 -C 6 alkyl,
Z 1 represents a halogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
Z a is C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, di(C 1 -C 6 alkyl)aminocarbonyl, di(C 1 - C6 alkyl)aminosulfonyl or —C(O)C(O)OR a ,
2. The thienouracil compound or salt thereof according to claim 1, wherein m and m1 represent an integer of 1 or 2. - R2は、C1~C6アルキル、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル、-C(O)R9又はフェニルを表し、
R4は、-C≡C-R7、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、C1~C6アルキル、R11によって置換されたC1~C6アルキル、E-38、E-44又はL-5を表し、
R7は、C1~C6アルキルを表し、
R8は、-C(=NOR17)R18、フェニル、(Z1)mによって置換されたフェニル、G-3、G-4、G-23又はG-53を表し、
R9は、C1~C6アルキル、C1~C6アルコキシカルボニル、C1~C6アルキルアミノカルボニル、-C(=NORa)Ra1、フェニル、G-3、G-4、G-15~G-17、G-21、G-22、G-52又はG-53を表し、
R11は、C1~C6アルキルアミノカルボニルを表し、
R12は、C1~C6アルキルを表し、
R15は、C1~C6アルコキシを表し、
R17は、C1~C6アルキルを表し、
Zaは、C1~C6アルキルカルボニル、C1~C6アルコキシカルボニル、C1~C6アルキルスルホニル又はジ(C1~C6アルキル)アミノカルボニルを表す、請求項2に記載のチエノウラシル化合物又はその塩。 R 2 is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 8 , C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl, —C(O)R 9 or phenyl; represent,
R 4 represents —C≡C—R 7 , C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by R 11 , E-38, E-44 or L-5;
R 7 represents C 1 -C 6 alkyl,
R 8 represents -C(=NOR 17 )R 18 , phenyl, phenyl substituted by (Z 1 ) m , G-3, G-4, G-23 or G-53;
R 9 is C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, —C(=NOR a )R a1 , phenyl, G-3, G-4, G- 15 to G-17, G-21, G-22, G-52 or G-53;
R 11 represents C 1 -C 6 alkylaminocarbonyl,
R 12 represents C 1 -C 6 alkyl,
R 15 represents C 1 -C 6 alkoxy,
R 17 represents C 1 -C 6 alkyl,
Thienouracil compounds according to claim 2, wherein Z a represents C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or di(C 1 -C 6 alkyl)aminocarbonyl. Or its salt. - R2は、R8によって置換されたC1~C6アルキル、C2~C6ハロアルケニル、C1~C6アルコキシカルボニル又は-C(O)R9を表し、
R4は、R15によって置換されたC1~C6アルキル又はL-1を表し、
R6は、E-38、E-44又はL-5を表し、
R8は、-C(=NOR17)R18、G-3又はG-4を表し、
R9は、G-3、G-4、G-21又はG-22を表し、
R18は、C1~C6アルキルを表し、
Zaは、C1~C6アルコキシカルボニルを表す、請求項3に記載のチエノウラシル化合物又はその塩。 R 2 represents C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl or —C(O)R 9 substituted by R 8 ;
R 4 represents C 1 -C 6 alkyl substituted by R 15 or L-1;
R 6 represents E-38, E-44 or L-5;
R 8 represents -C(=NOR 17 )R 18 , G-3 or G-4;
R 9 represents G-3, G-4, G-21 or G-22;
R 18 represents C 1 -C 6 alkyl,
A thienouracil compound or a salt thereof according to claim 3, wherein Z a represents C 1 -C 6 alkoxycarbonyl. - R4は、L-1を表す、請求項4に記載のチエノウラシル化合物又はその塩。 5. The thienouracil compound or salt thereof according to claim 4, wherein R 4 represents L-1.
- R4は、R15によって置換されたC1~C6アルキルを表す、請求項4に記載のチエノウラシル化合物又はその塩。 5. A thienouracil compound or a salt thereof according to claim 4, wherein R 4 represents C 1 -C 6 alkyl substituted by R 15 .
- 請求項1乃至請求項6の何れか1項に記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、農薬。 An agricultural chemical containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of claims 1 to 6.
- 請求項1乃至請求項6の何れか1項に記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、殺菌剤。 A fungicide containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of claims 1 to 6.
- 請求項1乃至請求項6の何れか1項に記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、農園芸用殺菌剤。 An agricultural and horticultural fungicide containing as an active ingredient one or more selected from the thienouracil compound and salts thereof according to any one of claims 1 to 6.
- 請求項1乃至請求項6の何れか1項に記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、抗真菌剤。 An antifungal agent containing, as an active ingredient, one or more selected from the thienouracil compounds and salts thereof according to any one of claims 1 to 6.
- 請求項1乃至請求項6の何れか1項に記載のチエノウラシル化合物及びその塩から選ばれる1種以上を有効成分として含有する、内部寄生虫防除剤。 An internal parasite control agent containing, as an active ingredient, one or more selected from the thienouracil compound and salts thereof according to any one of claims 1 to 6.
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---|---|---|---|---|
WO2019031384A1 (en) * | 2017-08-07 | 2019-02-14 | 日本曹達株式会社 | 1,3,5,6-tetrasubstituted thieno[2,3-d]pyrimidine-2,4-(1h,3h)dione compound and agricultural or horticultural bactericide |
WO2019072478A1 (en) * | 2017-10-10 | 2019-04-18 | Galderma Research & Development | Specific acetyl-coa carboxylase inhibitors for use in the treatment and/or prevention of acne |
WO2021149771A1 (en) * | 2020-01-22 | 2021-07-29 | 日産化学株式会社 | Thienouracil compound and pest control agent |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019031384A1 (en) * | 2017-08-07 | 2019-02-14 | 日本曹達株式会社 | 1,3,5,6-tetrasubstituted thieno[2,3-d]pyrimidine-2,4-(1h,3h)dione compound and agricultural or horticultural bactericide |
WO2019072478A1 (en) * | 2017-10-10 | 2019-04-18 | Galderma Research & Development | Specific acetyl-coa carboxylase inhibitors for use in the treatment and/or prevention of acne |
WO2021149771A1 (en) * | 2020-01-22 | 2021-07-29 | 日産化学株式会社 | Thienouracil compound and pest control agent |
Non-Patent Citations (2)
Title |
---|
AMEEN A. ABU-HASHEM; KHADIGA M. ABU-ZIED; MOHAMED F. EL-SHEHRY: "Synthetic utility of bifunctional thiophene derivatives and antimicrobial evaluation of the newly synthesized agents", MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY ; AN INTERNATIONAL JOURNAL OF CHEMISTRY, SPRINGER-VERLAG, AU, vol. 142, no. 5, 11 March 2011 (2011-03-11), AU , pages 539 - 545, XP019898682, ISSN: 1434-4475, DOI: 10.1007/s00706-011-0456-z * |
GABER HATEM M., BAGLEY MARK C., SHERIF SHERIF M.: "Antimicrobial investigations on synthetic p-tolylazo derivatives of thienopyrimidinone based on an ortho funtionalized thiophene nucleus", EUROPEAN JOURNAL OF CHEMISTRY, vol. 1, no. 2, 1 January 2010 (2010-01-01), pages 115 - 123, XP055968268, ISSN: 2153-2249, DOI: 10.5155/eurjchem.1.2.115-123.56 * |
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