JP4918215B2 - 殺菌剤組成物及び植物病害の防除方法 - Google Patents
殺菌剤組成物及び植物病害の防除方法 Download PDFInfo
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- JP4918215B2 JP4918215B2 JP2004307847A JP2004307847A JP4918215B2 JP 4918215 B2 JP4918215 B2 JP 4918215B2 JP 2004307847 A JP2004307847 A JP 2004307847A JP 2004307847 A JP2004307847 A JP 2004307847A JP 4918215 B2 JP4918215 B2 JP 4918215B2
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 1
- VDLGAVXLJYLFDH-UHFFFAOYSA-N fenhexamid Chemical compound C=1C=C(O)C(Cl)=C(Cl)C=1NC(=O)C1(C)CCCCC1 VDLGAVXLJYLFDH-UHFFFAOYSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 description 1
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- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
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- 230000002070 germicidal effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WNDZGSZAABWBMU-UHFFFAOYSA-N hydroxyboron Chemical compound O[B] WNDZGSZAABWBMU-UHFFFAOYSA-N 0.000 description 1
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- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- BORBNQCRRSMQLM-UHFFFAOYSA-N iron;2,3,4-trimethoxy-6-methylbenzoyl cyanide Chemical compound [Fe].COC1=CC(C)=C(C(=O)C#N)C(OC)=C1OC BORBNQCRRSMQLM-UHFFFAOYSA-N 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
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- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
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- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- IUGMFAGXILFTSB-UHFFFAOYSA-M lithium;oxolane;chloride Chemical compound Cl[Li].C1CCOC1 IUGMFAGXILFTSB-UHFFFAOYSA-M 0.000 description 1
- DQZLQYHGCKLKGU-UHFFFAOYSA-N magnesium;propane Chemical compound [Mg+2].C[CH-]C.C[CH-]C DQZLQYHGCKLKGU-UHFFFAOYSA-N 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
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- 229920000940 maneb Polymers 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
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- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
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- 239000006072 paste Substances 0.000 description 1
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- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
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- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
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- 229920002635 polyurethane Polymers 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Description
(1)式(VI−1):
[式中、R1、R2'、R2”及びpは前述の通りであり、Mは金属原子である]で表される化合物とを遷移金属触媒存在下、一酸化炭素雰囲気下で反応させることにより、前記式(I)の化合物又はその塩を製造する方法。
(a)前記式(XIII)の化合物とハロゲン化剤とを反応させて、式(XV):
(b)第1工程で得られた式(XV)の化合物と、前記式(XIV)の化合物とのフリーデルクラフト反応によって、前記式(I)の化合物を得る第2工程から構成される方法。
3-(2,3,4-トリメトキシ-6-メチルベンゾイル)-4,5-ジクロロ-2-メトキシピリジン(化合物No.15)の合成
(a)ジイソプロピルアミン34.2 g(340 mmol)をテトラヒドロフラン400 mlに溶解した溶液中に、-20 ℃でn-ブチルリチウム(1.57 mol/lへキサン溶液)222 mlを滴下し、1時間攪拌した。溶液を-78 ℃に冷却し、2-フルオロピリジン32.0g(330 mmol)をテトラヒドロフラン50 mlに溶解した溶液を添加し、4時間攪拌し2-フルオロ-3-ピリジルリチウムを調製した。ついでこの溶液にヨウ素87.1 g(341 mmol)をテトラヒドロフラン150 mlに溶解した溶液を添加し1時間攪拌した。混合物に水200 mlを加えて反応を停止し、減圧下、テトラヒドロフランを留去した。エーテルで抽出後、有機層を硫酸ナトリウムで乾燥、ろ過し、減圧下で溶媒を留去し、2-フルオロ-3-ヨードピリジンの粗生成物67.4 g(粗収率92 %)を得た。
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 6.91-6.88(m,1H), 8.08-8.12(m,2H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 7.33(d,1H, J = 2.8 Hz), 7.51(d,1H, J = 5.2 Hz), 7.88(dd,1H, J=5.2 Hz, 2.8 Hz)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 3.86(s,3H), 7.12-7.16(m,2H), 7.79(d,1H, J = 5.6 Hz)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 3.91(s, 3H), 6.70(d, 1H, J = 2.0 Hz), 6.81(dd, 1H, J = 6.0 Hz, 2.0 Hz), 7.99(d,1H, J = 6.0 Hz)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 3.90(s, 3H), 6.85(s, 1H), 8.14(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.32(s, 3H), 3.52(s, 3H), 3.77(s, 3H), 3.82(s, 3H), 4.11(s, 3H), 5.32(d, 1H, J=10.0 Hz), 6.21(d, 1H, J=10.0 Hz), 6,55(s, 1H), 8.07(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.46(s,3H), 3.45(s,3H), 3.74(s,3H), 3.90(s,3H), 4.00(s,3H), 6.55(s,1H), 8.13(s,1H)
3-(2,3,4-トリメトキシ-6-メチルベンゾイル)-2-メトキシ-4,5-ジメチルピリジン(化合物No.20)の合成
(a)ジイソプロピルアミン4.02 g(39.8 mmol)をテトラヒドロフラン70 mlに溶解した溶液中に-78 ℃でn-ブチルリチウム(1.57 mol/lヘキサン溶液)26.5 mlを滴下し、30分攪拌した。この溶液に、2-フルオロ-5-メチルピリジン4.42 g(39.8 mmol)をテトラヒドロフラン18 mlに溶解した溶液を添加し、4時間攪拌し、2-フルオロ-5-メチル-3-ピリジルリチウムを調製した。ついでこの溶液にヨウ素10.1 g(39.8 mmol)をテトラヒドロフラン27 mlに溶解した溶液を添加し、2時間攪拌した。水16 ml、チオ硫酸ナトリウム水溶液120 mlを投入し、エーテルにて抽出後、有機層を硫酸マグネシウムで乾燥、ろ過し、減圧下で溶媒を留去し、得られた粗生成物をシリカゲルクロマトグラフィーにて精製し、2-フルオロ-3-ヨード-5-メチルピリジン3.15 g(収率33 %)を得た。
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.27(s, 3H), 7.95(m, 2H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.21(s, 3H), 2.42(s, 3H), 3.72(s, 3H), 3.79(s, 3H), 3.81(s, 3H), 4.97(d, 1H, J = 10.0 Hz), 6.08(d, 1H, J = 10.0 Hz), 6.46(s, 1H), 7.86(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.41(s, 3H), 2.50(s, 3H), 3.42(s, 3H), 3.90(s, 3H), 3.74(s, 3H), 6.57(s, 1H), 7.94(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.28(s, 3H), 2.32(s, 3H), 2.42(s, 3H), 3.35(s, 3H), 3.74(s, 3H), 3.90(s, 3H), 6.57(s, 1H), 7.94(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.19(s, 3H), 2.21(s, 3H), 2.39(s, 3H), 3.24(s, 3H), 3.70(s, 3H), 3.74(s, 3H), 3.87(s, 3H), 6.53(s, 1H), 7.87(s, 1H)
3-(2,3,4-トリメトキシ-6-メチルベンゾイル)-5-ブロモ-4-クロロ-2-メトキシピリジン(化合物No.23)の合成
(a)4-クロロ-2-メトキシピリジン5.76g(40.1mmol)をジメチルホルムアミド20 mlに溶解させ、N-ブロモ琥珀酸イミド8.01g(98%品、44.1mmol)のジメチルホルムアミド(20 ml)溶液を30分かけて滴下した。室温で2日間攪拌した後、未反応の原料が確認された為、更にN-ブロモ琥珀酸イミド2.85g(98%品、16 mmol)を加え室温で更に3日攪拌した。反応混合物を水250 mlに注ぎ込み、エーテル(各100 ml)で3回抽出した。有機層を水(100 ml)、チオ硫酸ナトリウム水溶液(100 ml)ついで飽和食塩水(100 ml)で洗浄し、硫酸マグネシウムで乾燥、ろ過し、減圧下溶媒を留去した。得られた粗生成物をシリカゲルクロマトグラフィーにて精製し、5-ブロモ-4-クロロ-2-メトキシピリジン7.10g(収率80 %)を得た。
1H-NMR(CDCl3、400MHz):δ(ppm)=3.91(s,3H)、6.89(s,1H)、8.28(s,1H)
反応混合物に飽和塩化アンモニウム水溶液37 ml、ついで水150 mlを加え、室温に昇温後、酢酸エチル(各150 ml)で3回抽出した。有機層を飽和食塩水(100 ml)で洗浄し、硫酸マグネシウムで乾燥、ろ過し、減圧下で溶媒を留去した。得られた粗生成物をシリカゲルクロマトグラフィーにて精製し、(2,3,4-トリメトキシ-6-メチルフェニル)(5-ブロモ-4-クロロ-2-メトキシ-3-ピリジル)メタノール6.53 g(収率56 %)を得た。
1H-NMR(CDCl3、400MHz):δ(ppm)=2.33(s,3H)、3.54(s,3H)、3.79(s,3H)、3.84(s,3H)、3.98(s,3H)、5.32(d,1H J=9.6Hz)、6.23(d,1H J=9.6Hz)、6.49(s,1H)、8.21(s,1H)
1H-NMR(CDCl3、400MHz):δ(ppm)=2.48(s,3H)、3.45(s,3H)、3.75(s,3H)、3.87(s,3H)、3.91(s,3H)、6.57(s,1H)、8.27(s,1H)
3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(化合物No.35)の合成
(a)2‐メトキシ‐4‐メチルピリジン8.0 g(65 mmol)のN,N‐ジメチルホルムアミド(DMF)15 ml溶液中にN‐クロロ琥珀酸イミド9.2 g(69 mmol)を投入し、18時間攪拌した。反応溶液に水を加え、水層をジエチルエーテルで抽出後、有機層を飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥後、ろ過、減圧下溶媒を留去した。粗生成物をシリカゲルカラムクロマトグラフィーにて精製し、5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(融点32 33 ℃)8.5g(収率82 %)を得た。
1HNMR(CDCl3, 300 MHz):δ2.32(s, 3H), 3.89(s, 3H), 6.62(s, 1H), 8.05(s, 1H)
1HNMR(CDCl3, 300 MHz):δ2.51(s, 3H), 3.98(s, 3H), 8.01(s, 1H)
1HNMR(CDCl3, 300 MHz):δ2.26(s, 3H), 2.27(s, 3H), 3.54(s, 3H), 3.80(s, 3H), 3.84(s, 3H), 3.94(s, 3H), 5.32(d, 1H, J = 9.0 Hz), 6.12(d, 1H, J = 9.0 Hz), 6.47(s, 1H), 8.02(s, 1H)
1HNMR(CDCl3, 300 MHz):δ2.31(s, 3H), 2.40(s, 3H), 3.30(s, 3H), 3.73(s, 3H), 3.74(s, 3H), 3.88(s, 3H), 6.54(s, 1H), 8.06(s, 1H)
3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐4‐トリフルオロメチル‐2‐メトキシ‐5‐メチルピリジン(化合物No.37)の合成
(a)2‐クロロ‐4‐トリフルオロメチルピリジン5.05 g(27.8 mmol)、ナトリウムメトキシド3.59 g(66.5 mmol)をメタノール40 mlに溶解した溶液を加熱還流下4時間撹拌した。水を加えて反応を停止し、ジエチルエーテルで抽出した後に有機層を無水硫酸ナトリウムで乾燥、シリカゲルケーキにてろ過した。減圧下で溶媒を留去し、4‐トリフルオロメチル‐2‐メトキシピリジン4.19 g(収率85 %)を得た。
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 3.96(s, 3H), 6.95(s, 1H), 7.05(d, 1H, J = 5.2 Hz), 8.29(d, 1H, J = 5.2 Hz)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 3.94(s, 3H), 7.03(s, 1H), 8.37(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.35(s, 3H), 3.29(s, 3H), 3.74(s, 3H), 3.82(s, 3H), 3.92(s, 3H), 4.87(d, 1H, J = 10.8 Hz), 6.21(d, 1H, J = 10.8 Hz), 6.51(s, 1H), 8.31(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.57(s, 3H), 3.36(s, 3H), 3.75(s, 3H), 3.86(s, 3H), 3.93(s, 3H), 6.59(s, 1H), 8.38(s, 1H)
1H-NMR(CDCl3, 400 MHz) : δ(ppm) = 2.41(s, 3H), 2.56(s, 3H), 3.29(s, 3H), 3.74(s, 3H), 3.83(s, 3H), 3.91(s, 3H), 6.58(s, 1H), 8.05(s, 1H)
4−(2,3,4−トリメトキシ−6−メチルベンゾイル)−2,5−ジクロロ−3−トリフルオロメチルピリジン(化合物No.39)の合成
(a)ジイソプロピルアミン3.6 ml(25 mmol)をジエチルエーテル60 mlに溶解した溶液中に 、0 ℃でn−ブチルリチウム(1.5 mol/lへキサン溶液)17 ml(25 mmol)を滴下し、45分攪拌した。溶液を−78 ℃に冷却し、2,3,6−トリクロロ−5−トリフルオロメチルピリジン6.0 g(24 mmol)をジエチルエーテル8 mlに溶解した溶液を添加し、25分攪拌して2,3,6‐トリクロロ‐5‐トリフルオロメチル‐4‐ピリジルリチウムを調製した後に、2,3,4−トリメトキシ−6−メチルベンズアルデヒド5.0 g(24 mmol)をトルエン12 mlに溶解した溶液を添加し、1時間攪拌した。混合物に水30 mlを加えて反応を停止し、水層を酢酸エチルで抽出後、有機層を無水硫酸ナトリウムで乾燥、ろ過し、減圧下で溶媒を留去し、(2,3,4−トリメトキシ−6−メチルフェニル)(2,3,6−トリクロロ−5−トリフルオロメチル−4−ピリジル)メタノール(融点131〜135 ℃)を得た。
4−(2,3,4−トリメトキシ−6−メチルベンゾイル)−2−クロロ−3−トリフルオロメチル−5−メトキシピリジン(化合物No.40)の合成
(a)ジイソプロピルアミン15.0 ml(107 mmol)のジエチルエーテル120 ml溶液中に、0℃でn−ブチルリチウム(1.5mol/lへキサン溶液)70.0 ml(106 mmol)を滴下し、1時間攪拌した。溶液を−78 ℃に冷却し、2,3−ジクロロ−5−トリフルオロメチルピリジン22.1 g(102 mmol)のジエチルエーテル10 ml溶液を添加し、30分攪拌し2,3‐ジクロロ‐5‐トリフルオロメチル‐4‐ピリジルリチウムを調製した後に2,3,4−トリメトキシ−6−メチルベンズアルデヒド21.0 g(100 mmol)のトルエン40 ml溶液を加え2時間撹拌した。混合物に水30 mlを加えて反応を停止し、水層を酢酸エチルで抽出後、有機層を無水硫酸ナトリウムで乾燥、ろ過し、減圧下で溶媒を留去した。粗生成物をシリカゲルカラムクロマトグラフィーにて精製し、(2,3,4−トリメトキシ−6−メチルフェニル)(2,3−ジクロロ−5−トリフルオロメチル−4−ピリジル)メタノール(融点95〜98 ℃)24.8 g(収率58 %)を得た。
(d)工程(c)で得られた4−(2,3,4−トリメトキシ−6−メチルベンゾイル)−3−クロロ−5−トリフルオロメチルピリジン18.5 g(47.5 mmol)、ヘキサメチルリン酸トリアミド16.6 ml(95.4 mmol)のトルエン150 ml溶液中にナトリウムメトキシド16.4 g(304 mmol)を加え、加熱還流下30分間撹拌した。水を加え反応を停止した後に、水層を酢酸エチルで抽出し有機層を無水硫酸ナトリウムで乾燥、ろ過し、減圧下で溶媒を留去した。粗生成物をシリカゲルカラムクロマトグラフィーにて精製し、4−(2,3,4−トリメトキシ−6−メチルベンゾイル)−3−メトキシ−5−トリフルオロメチルピリジン(融点103〜106 ℃)11.7 g(収率64 %)を得た。
3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(化合物No.35)の合成
(a)2,3,4‐トリメトキシ‐6‐メチルベンズアルデヒド45.6g(217mmol)をジメチルスルホキシド130mlに溶解させ、リン酸二水素ナトリウム5.2g(44mmol)水溶液(50ml)を20分かけて滴下した。ついで亜塩素酸ナトリウム28g(305mmol)水溶液(180ml)を3時間かけて滴下し、2時間攪拌した。発泡しなくなるまで飽和炭酸水素ナトリウム水溶液を加えて一時間攪拌した後に、反応溶液を酢酸エチル50mlで2回洗浄、ついで、濃塩酸を加えて水層を酸性にし、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥、ろ過し、減圧下溶媒を留去した。得られた結晶をヘキサンにて洗浄し、2,3,4‐トリメトキシ‐6‐メチル安息香酸(融点 95 97 ℃)45.6g(収率93%)を得た。
1HNMR:δ2.56(s, 3H), 3.86(s, 3H), 3.91(s, 3H), 4.03(s, 3H), 6.60(s, 1H)
(b−1)イソプロピルマグネシウムクロリド(2Mテトラヒドロフラン溶液)6.8ml(13.6mmol)を0℃に冷却し、3‐ブロモ‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン1.6g(6.6mmol)をテトラヒドロフラン5mlに溶解させた溶液を滴下し、同温度で3時間攪拌し、5‐クロロ‐2‐メトキシ‐4‐メチル‐3‐ピリジルマグネシウムクロリドを調整した。さらに反応溶液を‐78℃に冷却し、シアン化銅(I)1.2g(13.3mmol)及び塩化リチウム1.15g(27.1mmol)をテトラヒドロフラン15mlに溶解させた溶液を滴下し、5‐クロロ‐2‐メトキシ‐4‐メチル‐3‐ピリジル銅反応剤を調整した。一方、(a)工程で合成した2,3,4‐トリメトキシ‐6‐メチル安息香酸3.2g(14.3mmol)を塩化チオニル7ml中で3時間加熱還流し、過剰の塩化チオニルを減圧下留去して調整した2,3,4‐トリメトキシ‐6‐メチル安息香酸クロリドをテトラヒドロフラン7mlに溶解させた溶液を、先に調整したピリジル銅反応剤中に‐78℃で滴下し、1時間攪拌した後に室温に上昇させ、更に2時間攪拌した。反応溶液に水、アンモニア水を加えて反応を停止し、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥後、ろ過、減圧下で溶媒を留去した。粗生成物をシリカゲルカラムクロマトグラフィーにて精製し 3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(融点85 88 ℃)2.6g(収率57%)を得、1HNMRにて化合物を同定した。
(b−2) イソプロピルマグネシウムクロリド1Mテトラヒドロフラン溶液11ml(11.0mmol)、 3‐ブロモ‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン2.5g(10.6mmol) を用いて工程(b−1)と同様の反応を行い、シアン化銅(I)、塩化リチウムテトラヒドロフラン溶液の代わりにテトラキストリフェニルホスフィンパラジウム1.25g(1.1mmol)を用い2,3,4‐トリメトキシ‐6‐メチル安息香酸2.4g(10.6mmol)と塩化チオニル5mlから調整した2,3,4‐トリメトキシ‐6‐メチル安息香酸クロリドを0℃で2時間かけて滴下し、同温度で15時間撹拌し、3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン1.7g(収率43%)を得、1HNMRにて化合物を同定した。
(b−3) 工程(b−2)と同様の反応で、イソプロピルマグネシウムクロリド1Mテトラヒドロフラン溶液の代わりにイソプロピルマグネシウムクロリド0.5Mテトラヒドロフラン溶液22ml(22.0mmol)、テトラキストリフェニルホスフィンパラジウムの代わりに塩化銅1.14g(11.5mmol)を用いて、3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン1.7g(収率43%)を得、1HNMRにて化合物を同定した。
3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(化合物No.35)の合成
(a)2‐ブロモ‐3,4,5‐トリメトキシトルエン5.0g(19mmol)をジエチルエーテル50mlに溶解した溶液を‐78℃に冷却し、n‐ブチルリチウム(1.6Mヘキサン溶液)15ml(24mmol)を滴下し、1.5時間攪拌し、2,3,4‐トリメトキシ‐6‐メチル‐2‐フェニルリチウムを発生させた後に、ボロン酸トリメチル4.9ml(43mmol)を滴下し、更に1時間攪拌した。希硫酸を加えて反応を停止し、30分攪拌した後に、更に水を加えた。水層を酢酸エチルで抽出し、有機層を飽和食塩水で洗浄、無水硫酸マグネシウムで乾燥、ろ過し、減圧下溶媒を留去し、2,3,4‐トリメトキシ‐6‐メチルフェニルボロン酸(融点 99 102 ℃)3.26g(収率75%)を得た。
1HNMR:δ2.52(s, 3H), 3.83(s, 3H), 3.88(s, 3H), 3.94(s, 3H), 6.56(s, 1H)
(b)200mlオートクレーブに3‐ブロモ‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン1.0g(4.3mmol)、2,3,4‐トリメトキシ‐6‐メチルフェニルボロン酸1.2g(5.4mmol)、炭酸カリウム1.8g(13mmol)、塩化パラジウム46mg(0.26mmol)、トリシクロヘキシルホスフィン147mg(0.52mmol)、テトラヒドロフラン40mlを入れ、一酸化炭素ガスを10気圧封入し、120℃で20時間攪拌した。反応溶液をセライトろ過し、水を加え減圧下テトラヒドロフランを留去した。水層を酢酸エチルで抽出し、有機層を無水硫酸マグネシウムで乾燥後、ろ過し、減圧下溶媒を留去した。粗生成物をシリカゲルカラムクロマトグラフィーにて精製し 3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(融点92 94 ℃)0.31g(収率20%)を得、1HNMRにて化合物を同定した。
3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(化合物No.35)の合成
(a) 攪拌機、冷却器、温度計及び窒素風船を備えた500ml四つ口フラスコに、マグネシウム5.4g(222 mmol)及びテトラヒドロフラン95 mlを仕込み、系内温度を40℃に保ちながらイソプロピルクロライド17.3 g(220 mmol)を滴下し、一晩攪拌した。続いて、系内温度を0℃以下に保ちながら3-ブロモ-5-クロロ-2-メトキシ-4-メチルピリジン47.3g(200 mmol)のテトラヒドロフラン95 ml溶液を滴下し、3時間攪拌後、ドライアイスの中に反応液を滴下した。
水300 ml中に反応液を投入し、分液後、水層に塩酸水を滴下して酸性化し、ジエチルエーテルで抽出した。減圧下溶媒を留去して5-クロロ-2-メトキシ-4-メチルニコチン酸(融点127-129℃)26g(収率65%)を得た。
(b) 攪拌機、冷却器、温度計及び窒素風船を備えた50 ml四つ口フラスコに、5-クロロ-2-メトキシ-4-メチルニコチン酸1.0g(4.96 mmol)、3,4,5-トリメトキシトルエン0.9g(4.94 mmol)、1,2-ジクロロエタン20 ml及び五酸化二りん7.1g(50.0 mmol)を仕込み、還流下1時間攪拌した。
水50 ml中に反応液を投入し、水酸化ナトリウム水溶液を加えてアルカリ性化し、分液後、減圧下溶媒を留去した。得られた残さにヘキサン5 mlを加え、析出した結晶を濾過して、目的物0.4g(収率22%)を得た。
3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(化合物No.35)の合成
還流冷却器を備えた20 mlナスフラスコに、5-クロロ-2-メトキシ-4-メチルニコチン酸1.0g(5.0 mmol)、1,2-ジクロロエタン10 g及び塩化オキサリル0.62g(5.0 mmol)を仕込み、25℃で20分攪拌した後、60℃〜65℃で2時間加熱した。25℃に冷却した後、反応混合物に3,4,5-トリメトキシトルエン0.80g(4.4 mmol)、無水塩化アルミニウム0.70g(5.2 mmol)を加えて、25℃で3時間攪拌した。
反応混合物に水及び酢酸エチルを加え抽出、分液後、有機層を硫酸ナトリウムで乾燥し、減圧下で溶媒を留去した。析出した固体にn-ヘキサンを加えろ過、乾燥し目的物0.66g(収率36.1%)を得た。
3‐(2,3,4‐トリメトキシ‐6‐メチルベンゾイル)‐5‐クロロ‐2‐メトキシ‐4‐メチルピリジン(化合物No.35)の合成
(a) 2,3,4‐トリメトキシ‐6‐メチル安息香酸6.0g(26.6mmol)に塩化チオニル10mlを加え加熱還流下4時間撹拌した後、減圧下で過剰の塩化チオニルを留去した。そこへトルエン20ml、アセトニトリル8ml、シアン化銅(I)3.1g(34.5mmol)を加え加熱還流下16時間撹拌した。室温に冷却後、反応溶液をセライトで濾過し、減圧下溶媒を留去した。粗生成物をシリカゲルカラムクロマトグラフィーにて精製し、2,3,4‐トリメトキシ‐6‐メチルベンゾイルシアニド2.8g(収率45%)を得た。
1HNMR:δ2.44(s, 3H), 3.85(s, 3H), 3.95(s, 3H), 4.14(s, 3H), 6.53(s, 1H)
(a)攪拌機、温度計及びガス導入管(入)を備えた2L四つ口フラスコに、2-アミノ-4-メチルピリジン324 g(3.00 mol)及びメタノール485 gを仕込み混合溶解した後、系内温度を10-30℃に保ちながら塩化水素ガス361.4g(9.90 mol)を1時間30分かけて導入した。
次に、攪拌機、温度計、滴下ロート及びガス発生装置とジアゾ化反応装置を連結させた気泡カウンター付きの導入管(出)を備えた2L四つ口フラスコに、亜硝酸ナトリウム414g(6.00 mol)、メタノール211g(6.60 mol)及び水454gを混合し、系内温度を20-30℃に保ちながら38%硫酸水溶液812.4g(3.15 mol)を5時間かけて滴下した。
亜硝酸メチル発生装置では、38%硫酸水溶液が滴下されると同時に相当の亜硝酸メチルガスが発生し、気泡カウンターを通じジアゾ化反応装置に導入される。
一方、ジアゾ化反応においては系内温度を20-30℃に維持出来るように水冷した。
亜硝酸メチルガス導入終了後、同温にて13時間攪拌し反応を終了させた。
メタノールを減圧留去した後、水648 gを投入し、さらに30℃以下で40%水酸化ナトリウム水溶液518gを滴下し系内のpHを12に調整した。
生成オイルを910gのジエチルエーテルで抽出し、分液後、減圧下溶媒を留去し、375.3 gのオイルを得た。尚、このオイル(粗生成物)の組成は2-クロロ-4-メチルピリジン70.7%(収率69.5%)、2-メトキシ-4-メチルピリジン26.6%(収率27.2%)、2-アミノ-4-メチルピリジン2.6%であった。
滴下終了後、メタノールを留去しながら3時間加熱還流した。(この間のメタノールの留去量は120gであった。)
反応終了後、系内の残存メタノールを減圧留去した後、水750gを投入し、無機塩を溶解した。
生成オイルを1050gのジエチルエーテルで抽出し、分液後、減圧下溶媒を留去し、370gのオイル(粗生成物)を得た。尚、得られた2-メトキシ-4-メチルピリジンの純度は95%であった。(2-アミノ-4-メチルピリジンからの2段階収率は95%)
5-クロロ-4-メチル-2-メトキシ-ニコチン酸の合成
(a)4,4-ジシアノ-3-メチル-3-ブテナール-ジメチルアセタール、1,1-ジシアノ-4-メトキシ-2-メチル-1,3-ブタジエンの混合物の合成
ピペリジン3.15g(37mmol)のトルエン100ml溶液に酢酸2.28g(37mmol)を加え室温で1時間攪拌した後、アセチルアセトアルデヒドジメチルアセタール49.3g(373 mmol)のトルエン20ml溶液を加えた。更にマロノニトリル24.65g(373 mmol)のトルエン30ml溶液を20分かけてゆっくりと加え、室温で5日間攪拌を行なった。反応混合物を水50mlで洗浄後、硫酸マグネシウムで乾燥、減圧下溶媒を留去し4,4-ジシアノ-3-メチル-3-ブテナール-ジメチルアセタール、1,1-ジシアノ-4-メトキシ-2-メチル-1,3-ブタジエンの混合物69.35gが得られた。
(a)で得られた4,4-ジシアノ-3-メチル-3-ブテナール-ジメチルアセタール、1,1-ジシアノ-4-メトキシ-2-メチル-1,3-ブタジエンの混合物69.35gを濃硫酸113gに30℃を超えないように3時間かけてゆっくと加えた。室温で20分攪拌した後、50℃に昇温し、同温度で2時間攪拌を行なった。放冷後反応混合物を水−氷(500ml)にゆっくりと注加し、得られた結晶を濾取、結晶を水100mlで洗浄した。結晶を一週間風乾し、更に減圧下70℃で8時間乾燥し、3-シアノ-4-メチルピリドン34.2g(2段階収率68%)の粗結晶を得た。1H-NMR(400MHz、DMSO-d6):δ(ppm) 2.35(s,3H)、6.29(d,J=6.4Hz,1H) 、7.64(d,J=6.4Hz,1H)
五塩化リン6.52g(31.3mmol)、オキシ塩化リン30ml(48g、313mmol)の混合物に3-シアノ-4-メチルピリドン14g(104mmol)をゆっくりと加え、室温で70分、次いで加熱還流下、2時間攪拌を行なった。放冷後、反応混合物を氷−水(400ml)に注ぎ過剰の反応剤を分解した後、ジクロロメタン100mlで3回抽出を行なった。ジクロロメタン溶液を飽和食塩水100mlで洗浄、硫酸マグネシウムで乾燥、減圧下溶媒を留去し、2-クロロ-3-シアノ-4-メチルピリジンの粗結晶15.1gを得た。1H-NMR(400MHz、DMSO-d6):δ(ppm) 2.86(s,3H)、7.89(d,J=5.6Hz,1H) 、8.86(d,J=5.6Hz,1H)
(c)で得られた2-クロロ-3-シアノ-4-メチルピリジンの粗結晶15.1gを無水メタノール150mlに溶解し、28%ナトリウムメトキシドのメタノール溶液24.9g(129mmol)を加え、室温で2日間攪拌した。反応混合物を飽和食塩水200mlに注ぎ込み、酢酸エチル100mlで3回抽出した。酢酸エチル溶液を硫酸マグネシウムで乾燥、セライト−シリカゲルカラムを通して濾過、カラムを酢酸エチルで十分に洗浄した。濾液、洗浄液を併せ減圧下溶媒を留去し、3-シアノ-4-メチル-2-メトキシピリジン14.04gの粗結晶を得た。1H-NMR(400MHz、CDCl3):δ(ppm) 2.51(s,3H)、4.03(s,3H)、6.84(d,J=5.2Hz,1H) 、8.18(d,J=5.2 Hz,1H)
(d)で得られた3-シアノ-4-メチル-2-メトキシピリジン14.04g(95mmol)をジメチルホルムアミド100mlに溶解し、N-クロロコハク酸イミド25.4g(190mmol)を加え室温で3日攪拌を行なった。薄層クロマトグラフィーで反応の進行を確認したところ、原料の残存がみとめられた為、50℃で22時間、次いで60℃で22時間攪拌を行なった。放冷後、反応混合物を水300mlに注ぎ、酢酸エチル100mlで3回抽出を行なった。酢酸エチル溶液を水150mlで2回、次いで飽和食塩水100mlで順次洗浄し、硫酸マグネシウムで乾燥、減圧下溶媒を留去した。得られた残さをシリカゲルカラムで精製し、5-クロロ-3-シアノ-4-メチル-2-メトキシピリジン13.68g(3段階収率79%)を得た。1H-NMR(400MHz、CDCl3):δ(ppm) 2.56(s,3H)、4.03(s,3H)、8.23(s,1H)
5-クロロ-3-シアノ-4-メチル-2-メトキシピリジン2.47g(13.5mmol)を無水ジクロロメタン50mlに溶解し、‐78℃に冷却後、1Mジイソブチルアルミニウムヒドリドのトルエン溶液20.3ml(20.3mmol)をゆっくりと滴下した。‐78℃で2時間半攪拌した後、徐々に室温に昇温し、同温度で3日間攪拌を行なった。得られた溶液を氷浴で冷却し、水30mlをゆっくりと加え、反応を終結させた。反応混合物を1N塩酸150mに注ぎ込み、ジクロロメタン100mlで2回抽出を行なった。ジクロロメタン溶液を飽和食塩水100mlで洗浄、硫酸マグネシウムで乾燥、減圧下溶媒を留去し粗5-クロロ-3-ホルミル-4-メチル-2-メトキシピリジンを得た。1H-NMR(400MHz、CDCl3):δ(ppm) 2.65(s,3H)、4.03(s,3H)、8.25(s,1H)、10.48(s,1H)
(f)で得られた粗5-クロロ-3-ホルミル-4-メチル-2-メトキシピリジンをジメチルスルホキシド14mlに溶解し、リン酸二水素ナトリウム0.33g(2.7mmol)水溶液5.7mlを加え、更に亜塩素酸ナトリウム2.16g(79%品、18.9mmol)水溶液20mlを3時間かけてゆっくりと滴下した。得られた混合物を室温で5日間攪拌し、飽和重曹水50mlを加え一夜攪拌を行なった。得られた溶液を酢酸エチル50mlで2回洗浄した後、水層を濃塩酸で酸性にし、酢酸エチル70mlで3回抽出を行なった。酢酸エチル溶液を飽和食塩水50mlで洗浄、硫酸マグネシウムで乾燥、減圧下溶媒を留去し粗結晶を得た。再度粗結晶を酢酸エチル50mlに溶解し、飽和重曹水50mlで2回逆抽出、水層を濃塩酸で酸性にし、酢酸エチル70mlで3回抽出を行なった。酢酸エチル溶液を飽和食塩水50mlで洗浄し、硫酸マグネシウムで乾燥、減圧下溶媒を留去し白色の結晶を得た。ヘキサン50mlで結晶を洗浄後、風乾し、5-クロロ-4-メチル-2-メトキシ-ニコチン酸0.55g(2段階収率20%)を得た。1H-NMR(400MHz、CDCl3):δ(ppm) 2.46(s,3H)、3.99(s,3H)、8.16(s,1H)、
コムギうどんこ病予防効果試験
直径7.5 cmのポリ鉢でコムギ(品種:農林61号)を栽培し、1.5葉期に達した時に各供試化合物を所定濃度に調整した混合薬液をスプレーガンにて200L/haに相当するよう散布した。薬液が乾燥した後、うどんこ病菌の分生胞子を振り掛け接種し、20 ℃の恒温室内に保った。接種6から8日後に胞子形成面積を調査し、下記計算式によって発病率を求め、その結果を第1表〜第53表に示した。なお、無処理区の平均病斑面積は、薬液に代えて水をスプレーガンにて散布したこと以外は処理区と同様の操作を行なうことによって求めた。
発病率=(a/b)×100
a:処理区の平均病斑面積
b:無処理区の平均病斑面積
コルビーの式により、理論値を計算した。実験値が理論値よりも低い場合に、本発明の殺菌剤組成物は、コムギうどんこ病予防効果試験に関し相乗効果を有する。こういった場合におけるコルビーの式による理論値を第1表〜第53表の( )内に併せ示した。
直径7.5 cm のポリ鉢でキュウリ(品種:四葉)を栽培し、1.5 葉期に達した時に本発明化合物を所定濃度に調整した混合薬液10 mLをスプレーガンにて散布した。薬液が乾燥した後、うどんこ病菌の分生胞子懸濁液を噴霧接種し、20 ℃の恒温室内に保った。接種6〜11日後に胞子形成面積を調査し試験例3と同様にして発病率を求め、その結果を第54表〜第96表に示した。無処理区の平均病斑面積は、薬液に代えて水をスプレーガンにて散布したこと以外は処理区と同様の操作を行なうことによって求めた。
また、コルビーの式による理論値を第54表〜第96表の( )内に併せ示した。
製剤例1
(a)カオリン 78重量部
(b)β−ナフタレンスルホン酸ソーダホルマリン縮合物 2重量部
(c)ポリオキシエチレンアルキルアリールサルフェート 5重量部
(d)含水無晶形二酸化ケイ素 15重量部
以上の各成分の混合物と、式(I)の化合物と、エポキシコナゾールとを8:1:1の重量割合で混合し、水和剤が得られる。
(a)式(I)の化合物 0.5 重量部
(b)エポキシコナゾール 0.5 重量部
(c)ベントナイト 20 重量部
(d)カオリン 74 重量部
(e)リグニンスルホン酸ソーダ 5 重量部
以上の各成分に適量の造粒所要水を加え、混合、造粒して粒剤が得られる。
(a)本発明化合物 2重量部
(b)エポキシコナゾール 3重量部
(c)タルク 95重量部
以上の各成分を均一に混合して粉剤が得られる。
Claims (3)
- (a)3−(2,3,4−トリメトキシ−6−メチルベンゾイル)−5−クロロ−2−メトキシ−4−メチルピリジンと、(b)クレソキシムメチル及びアゾキシストロビンからなる群から選択される少なくとも1種の殺菌剤とを有効成分として含有することを特徴とする殺菌剤組成物。
- (a)の3−(2,3,4−トリメトキシ−6−メチルベンゾイル)−5−クロロ−2−メトキシ−4−メチルピリジンと、(b)の殺菌剤との混合重量比が1:10000 〜 10000:1である請求項1に記載の殺菌剤組成物。
- 請求項1に記載の殺菌剤組成物を植物に施用することを特徴とする植物病害の防除方法。
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