JP4785154B2 - 木材保存用防腐剤及び木材処理方法 - Google Patents
木材保存用防腐剤及び木材処理方法 Download PDFInfo
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- JP4785154B2 JP4785154B2 JP2010544114A JP2010544114A JP4785154B2 JP 4785154 B2 JP4785154 B2 JP 4785154B2 JP 2010544114 A JP2010544114 A JP 2010544114A JP 2010544114 A JP2010544114 A JP 2010544114A JP 4785154 B2 JP4785154 B2 JP 4785154B2
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- 239000002023 wood Substances 0.000 title claims description 58
- 239000003755 preservative agent Substances 0.000 title claims description 37
- 230000002335 preservative effect Effects 0.000 title claims description 34
- 238000004321 preservation Methods 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 34
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- 230000003115 biocidal effect Effects 0.000 claims description 16
- 230000000855 fungicidal effect Effects 0.000 claims description 16
- 230000002421 anti-septic effect Effects 0.000 claims description 15
- 150000003852 triazoles Chemical class 0.000 claims description 13
- 150000001880 copper compounds Chemical class 0.000 claims description 10
- 239000005749 Copper compound Substances 0.000 claims description 8
- 239000003171 wood protecting agent Substances 0.000 claims description 8
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- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims description 5
- 239000005757 Cyproconazole Substances 0.000 claims description 5
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- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims 1
- 238000003672 processing method Methods 0.000 claims 1
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- 230000015572 biosynthetic process Effects 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 39
- 229940126062 Compound A Drugs 0.000 description 23
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 23
- -1 triazole compound Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
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- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 14
- 241000233866 Fungi Species 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 238000002360 preparation method Methods 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
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- 239000004480 active ingredient Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XCCNRBCNYGWTQX-UHFFFAOYSA-N 3-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(N)=C1 XCCNRBCNYGWTQX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 230000000694 effects Effects 0.000 description 6
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- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 5
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- 239000003795 chemical substances by application Substances 0.000 description 5
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 3
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- 241001600095 Coniophora puteana Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 239000001099 ammonium carbonate Substances 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229940116318 copper carbonate Drugs 0.000 description 3
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000011120 plywood Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- 239000000243 solution Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- AGMMRUPNXPWLGF-AATRIKPKSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methyl 2,2-dimethyl-3-[(e)-prop-1-enyl]cyclopropane-1-carboxylate Chemical compound CC1(C)C(/C=C/C)C1C(=O)OCC1=C(F)C(F)=C(C)C(F)=C1F AGMMRUPNXPWLGF-AATRIKPKSA-N 0.000 description 2
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- MVIVDSWUOGNODP-UHFFFAOYSA-N 2-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1I MVIVDSWUOGNODP-UHFFFAOYSA-N 0.000 description 2
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
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- 230000007613 environmental effect Effects 0.000 description 2
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- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000001294 propane Substances 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
- 235000019260 propionic acid Nutrition 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LEZAYTDLNNEFJT-UHFFFAOYSA-N tetracosasodium octaborate tetrahydrate Chemical compound O.O.O.O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] LEZAYTDLNNEFJT-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical class 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
- 229910052725 zinc Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- MTYHLWRUYCUTPA-UHFFFAOYSA-L zinc;naphthalene-1-carboxylate Chemical compound [Zn+2].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 MTYHLWRUYCUTPA-UHFFFAOYSA-L 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/16—Inorganic impregnating agents
- B27K3/22—Compounds of zinc or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/343—Heterocyclic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/38—Aromatic compounds
- B27K3/40—Aromatic compounds halogenated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Description
(1)次式
(2)さらに、トリアゾール系殺菌剤を含有する前記(1)に記載の木材保存用防腐剤。
(3)トリアゾール系殺菌剤が、シプロコナゾール、エポキシコナゾール、およびテトラコナゾールから選ばれる1以上の殺菌剤である前記(2)に記載の木材保存用防腐剤。
防腐剤。
(4)さらに、他の抗生物性化合物を含む前記(1)〜(3)のいずれかに記載の木材保存用防腐剤。
(5)抗生物性化合物が、銅化合物から選択されるものである前記(4)に記載の木材保存用防腐剤。
(6)前記(1)〜(5)のいずれかに記載の防腐剤を用いて処理を行うことを特徴とする木材保存処理方法。
本発明の木材保存用防腐剤は各種の木材腐朽菌に対して極めて低薬量にて優れた防腐効果を有し、経済性に優れ、環境に対する負荷が小さい。
反応時間は、特に限定されないが、好適には0.5〜3時間程度である。
製剤化に使用される界面活性剤としては、アニオン系、ノニオン系、カチオン系、または両性イオン系の界面活性剤を使用することができる。
また、本発明における木材保存用防腐剤を木材に施用する場合の濃度は、通常0.1〜500g/m3(木材)、好ましくは、1〜100g/m3(木材)である。
で示される第四級アンモニウム化合物も、本発明の目的で用いることのできる抗生物性化合物の好適な例として挙げられる。具体的には、塩化ジデシルジメチルアンモニウム、塩化ベンザルコニウム、塩化ジオクチルジメチルアンモニウム、塩化ジラウリルジメチルアンモニウム、塩化ラウリルトチメチルアンモニウム、塩化セチルトチメチルアンモニウム、塩化オクタデシルピコリニウム、塩化オクチルジデシルピリジニウムアンモニウム、臭化ラウリルイソキノリニウムが挙げられる。
また、これらの抗生物性化合物は単独で用いても組み合わせて用いてもよい。
本発明の木材保存用防腐剤が有効に作用する木材腐朽菌には以下の菌種が含まれる。コニオフォラ・プテアナ(イドタケ)(Coniophora puteana)、トラメテス・ベルシコラー(カワラタケ)(Trametes versicolor)、ポスティア・プラセンタ(Postia placenta)、ポスティア・バポラリア(Poria vaporaria)、ポリア・バイランティー(Poria vaillantii)、グロエオフィリウム・セピアリウム(Gloeophylium sepiarium)、グロエオフィリウム・アドラタム(Gloeophylium adoratum)、グロエオフィリウム・アビエティナム(Gloeophylium abietinum)、グロエオフィリウム・トラベウム(Gloeophylium trabeum)、グロエオフィリウム・プロタクタム(Gloeophylium protactum)、レンティナス・レピドウス(Lentinus lepideus)、レンティナス・エドデス(Lentinus edodes)、レンティナス・シアチフォルメス(Lentinus cyathiformes)、レンティナス・スクアロロサス(Lentinus squarrolosus)、パキシラス・パヌオイデス(Paxillus panuoides)、ホミトプシス・パルストリス(Fomitopsis palustris)、プレウロタス・オストレアタス(Pleurotus ostreatus)、ドンキオポリア・エクスパンサ(Donkioporia expansa)、セルプウラ・ラクリマンス(ナミダタケ)(Serpula lacrymans)、セルプウラ・ヒマントイデス(Serpula himantoides)、グレノスポラ・グラフィー(Glenospora graphii)、ホミトプシス・リラシノギルバ(Fomitopsis lilacino-gilva) 、ペレニポリア・テフロポラ(Perenniporia tephropora)、アントロディア・キサンタ(Antrodia xantha)、アントロディア・バイランティー(Antrodia vaillantii)を含む担子菌類、クラドスポリウム・ヘルバラム(Cladosporium herbarum)を含む不完全菌類、ケトミウム・グロブサム(Chaetomiumu globsum)、ケトミウム・アルバアレナラム(Chaetomium alba-arenulum)、ペトリエラ・セティフェラ(Petriella setifera)、トリチュラス・スピラリス(Trichurus spiralis)、フミコウラ・グリセラ(Humicola grisera)を含む子嚢菌類。
オーレオバシディウム・プルランス(Aureobasidium pullulans)、スクレロフ・ピティオフィラ(Scleroph pithyophila)、スコプウラ・フィコミセス(Scopular phycomyces)、アスペルギルス・ニガー(Aspergillus niger)、ペニシリウム・バリアビル(Penicillium variabile)、トリコデルマ・ビリデ(Trichoderma viride)、トリコデルマ・リグノラム(Trichoderma rignorum)、ダクティレウム・フサリオイデス(Dactyleum fusarioides)を含む不完全菌類。カラトシステス・ミナー(Caratocystis minor)を含む子嚢菌類。ムコール・スピノサス(Mucor spinosus)を含む接合菌類。
本発明の木材保存用防腐剤は、様々な木製物質の処理剤として利用可能であり、木材、木片、木粉、合板、単板積層材、ファイバーボード、パーティクルボード、木質加工品、モミ、藁、竹材等の処理において好ましい効果を得ることができる。
本発明の木材保存用防腐剤は、製材、木材、木材加工品及び建造物の処理に使用できる。例えば、土台、大引、根太、床板、胴縁、間柱、床下地板、筋かい、垂木、屋根下地板、浴室軸組及び床組材、外構部材、ログハウス、バルコニー、テラス、門塀、東屋、ぬれ縁、デッキ材等の屋外建築用部材、枕木、電柱、基礎杭、道路用防音壁、橋梁等の土木用等に用いられる。木材の形状は、丸太、板材、角材、棒材、合板、単板積層材、チップボード等のいずれにも適用できる。
合成例1:化合物A
2−トリフルオロメチル安息香酸クロライド(シグマアルドリッチジャパン株式会社)1.3gを塩化メチレン20mlに溶解し、氷冷下、トリエチルアミン(和光純薬工業株式会社)0.88mlを加えた。3−イソプロピルアニリン(東京化成工業株式会社)0.85gを加え、室温で1時間撹拌後、1時間リフラックスを行い反応させた。冷却後、塩化メチレン20mlを加え、1N NaOH 40ml、1N HCl 40ml、飽和食塩水40mlで洗浄後、Na2SO4で脱水して、エバポレーターにて濃縮した。得られた反応物をシリカゲルカラムクロマトグラフィーにより精製し、酢酸エチル/ヘキサン系溶媒にて再結晶を行い、3’−イソプロピル−2−トリフルオロメチル安息香酸アニリドの淡黄色結晶1.8gを取得した。
融点;98〜101℃、
1HNMR(CDCl3)δppm;7.74−6.68(8H,m),3.00−2.77(1H,m),1.30(3H,s),1.23(3H,s)。
2−トリフルオロメチル安息香酸クロライド1.0g、トリエチルアミン0.70mlおよび3−イソプロポキシアニリン(シグマアルドリッチジャパン株式会社)0.76gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−イソプロポキシ−2−トリフルオロメチル安息香酸アニリドの淡黄色結晶1.5gを取得した。
融点;103〜106℃、
1HNMR(CDCl3)δppm;7.88−6.64(9H,m),4.69−4.42(1H,m),1.37(3H,s),1.30(3H,s)。
2−メチル安息香酸クロライド(シグマアルドリッチジャパン株式会社)0.77g、トリエチルアミン0.70mlおよび3−イソプロポキシアニリン0.76gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−イソプロポキシ−2−メチル安息香酸アニリドの淡黄色結晶1.3gを取得した。
融点;87〜90℃、
1HNMR(CDCl3)δppm;7.49−6.62(9H,m),4.69−4.43(1H,m),2.47(3H,s),1.36(3H,s),1.30(3H,s)。
2−メチル安息香酸クロライド1.0g、トリエチルアミン0.88mlおよび3−イソプロピルアニリン0.85gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−イソプロピル−2−メチル安息香酸アニリドの淡褐色結晶1.5gを取得した。
融点;80〜83℃、
1HNMR(CDCl3)δppm;7.53−6.92(9H,m),3.07−2.70(1H,m),2.51(3H,s),1.30(3H,s),1.23(3H,s)。
2−ヨード安息香酸クロライド(シグマアルドリッチジャパン株式会社)1.1g、トリエチルアミン0.56mlおよび3−イソプロピルアニリン0.54gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−イソプロピル−2−ヨード安息香酸アニリドの白色結晶0.8gを取得した。
融点;119〜122℃、
1HNMR(CDCl3)δppm;7.95−6.98(9H,m),3.08−2.78(1H,m),1.30(3H,s),1.23(3H,s)。
2−ヨード安息香酸クロライド1.1g、トリエチルアミン0.56mlおよび3−イソプロポキシアニリン0.60gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−イソプロポキシ−2−ヨード安息香酸アニリドの淡褐色結晶0.9gを取得した。
融点;97〜100℃、
1HNMR(CDCl3)δppm;7.90−6.61(9H,m),4.69−4.42(1H,m),1.36(3H,s),1.29(3H,s)。
2−ニトロ安息香酸クロライド(シグマアルドリッチジャパン株式会社)1.2g、トリエチルアミン0.88mlおよび3−イソプロピルアニリン0.85gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−イソプロピル−2−ニトロ安息香酸アニリドの淡黄色結晶1.5gを取得した。
融点;71〜74℃、
1HNMR(CDCl3)δppm;7.72−6.91(9H,m),3.07−2.77(1H,m),1.30(3H,s),1.22(3H,s)。
2−ブロム安息香酸クロライド(シグマアルドリッチジャパン株式会社)1.1g、トリエチルアミン0.7mlおよび3−イソプロピルアニリン0.67gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−イソプロピル−2−ブロム安息香酸アニリドの白色結晶1.0gを取得した。
融点;86〜89℃、
1HNMR(CDCl3)δppm;7.95−6.98(9H,m),3.08−2.78(1H,m),1.30(3H,s),1.23(3H,s)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよびアニリン(シグマアルドリッチジャパン株式会社)0.23gを用い、合成例1の場合と同様の反応および後処理操作を行い、2−トリフルオロメチル安息香酸アニリドの無色結晶0.5gを取得した。
融点;151〜152℃、
1HNMR(CDCl3)δppm;7.95−6.98(10H,m)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび2−イソプロピルアニリン(シグマアルドリッチジャパン株式会社)0.27gを用い、合成例1の場合と同様の反応および後処理操作を行い、2’−イソプロピル−2−トリフルオロメチル安息香酸アニリドの無色結晶0.52gを取得した。
融点;165〜168℃、
1HNMR(CDCl3)δppm;7.94−7.17(9H,m),3.22−2.92(1H,m),1.29(3H,s),1.21(3H,s)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび4−イソプロピルアニリン(シグマアルドリッチジャパン株式会社)0.34gを用い、合成例1の場合と同様の反応および後処理操作を行い、4’−イソプロピル−2−トリフルオロメチル安息香酸アニリドの無色結晶0.37gを取得した。
融点;166〜168℃、
1HNMR(CDCl3)δppm;7.90−7.17(9H,m),3.06−2.75(1H,m),1.29(3H,s),1.21(3H,s)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよびm−トルイジン(シグマアルドリッチジャパン株式会社)0.27gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−メチル−2−トリフルオロメチル安息香酸アニリドの淡黄色結晶0.7gを取得した。
融点;132〜135℃、
1HNMR(CDCl3)δppm;7.63−6.96(9H,m),2.37(3H,s)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび3−エチルアニリン(シグマアルドリッチジャパン株式会社)0.30gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−エチル−2−トリフルオロメチル安息香酸アニリドの淡黄色結晶0.6gを取得した。
融点;86〜89℃、
1HNMR(CDCl3)δppm;7.72−6.97(9H,m)、2.78−2.53(2H,q),1.32−1.16(3H,t)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび3−トリフルオロメチルアニリン(シグマアルドリッチジャパン株式会社)0.40gを用い、合成例1の場合と同様の反応および後処理操作を行い、2,3’−トリフルオロメチル安息香酸アニリドの淡黄色結晶0.8gを取得した。
融点;112〜115℃、
1HNMR(CDCl3)δppm;7.83−7.25(m)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび3−トリフルオロメトキシアニリン(シグマアルドリッチジャパン株式会社)0.44gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−トリフルオロメトキシ−2−トリフルオロメチル安息香酸アニリドの淡黄色結晶0.86gを取得した。
融点;67〜70℃、
1HNMR(CDCl3)δppm;7.63−7.00(m)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび3−フルオロアニリン(シグマアルドリッチジャパン株式会社)0.28gを用い、合成例合成例1の場合と同様の反応および後処理操作を行い、3’−フルオロ−2−トリフルオロメチル安息香酸アニリドの白色結晶0.39gを取得した。
融点;119〜122℃、
1HNMR(CDCl3)δppm;7.80−6.78(m)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび3−クロロアニリン(シグマアルドリッチジャパン株式会社)0.32gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−クロロ−2−トリフルオロメチル安息香酸アニリドの白色結晶0.59gを取得した。
融点;128〜131℃、
1HNMR(CDCl3)δppm;7.78−7.09(m)。
2−トリフルオロメチル安息香酸クロライド 0.5g、トリエチルアミン0.35mlおよび3−ブロムアニリン(シグマアルドリッチジャパン株式会社)0.43gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−ブロム−2−トリフルオロメチル安息香酸アニリドの白色結晶0.62gを取得した。
融点;143〜146℃、
1HNMR(CDCl3)δppm;7.84−7.20(m)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび3−ヨードアニリン(シグマアルドリッチジャパン株式会社)0.55gを用い、合成例1の場合と同様の反応および後処理操作を行い、3’−ヨード−2−トリフルオロメチル安息香酸アニリドの白色結晶0.93gを取得した。
融点;150〜153℃、
1HNMR(CDCl3)δppm;7.98−6.98(m)。
2−トリフルオロメチル安息香酸クロライド0.5g、トリエチルアミン0.35mlおよび5−イソプロピル−2−メチル−アニリン(東京化成工業株式会社)0.37gを用い、合成例1の場合と同様の反応および後処理操作を行い、5’−イソプロピル−2’−メチル−2−トリフルオロメチル安息香酸アニリドの淡黄色結晶0.78gを取得した。
融点;129〜132℃、
1HNMR(CDCl3)δppm;7.88−6.90(8H,m)、3.08−2.78(1H,m),2.25(3H,s),1.30(3H,s)、1.23(3H,s)。
化合物A、比較化合物1〜19の1%w/vジメチルスルホオキシド溶液をそれぞれ調製した。この薬剤をジメチルスルホオキシドで希釈し、所定量を滅菌後のポテトデキストロース寒天培地に十分混合し、直径90mmのシャーレ内に15ml注ぎ込み、室温に放置した。なお、コントロールとして、ジメチルスルホオキシドのみを添加したポテトデキストロース寒天培地も同様に作成した。培地が固まった後、あらかじめ培養しておいた代表的な木材腐朽菌であるイドタケ(Coniophora puteana)のコロニーから、菌糸を直径5mmのコルクボーラーで培地ごとくり抜き試験培地の中央に接種した。シャーレを25℃にて培養し、7日目に接種源から広がったコロニーの直径を測定し、下記式によってコントロールのコロニーの直径と比較した菌の生育阻害率を求め、阻害度として表した。結果を表1に示す。化合物Aのイドタケに対する効果はこれまで開示されてきた化合物に比べ明らかに強いものであった。
化合物A、シプロコナゾール(和光純薬工業株式会社)、エポキシコナゾール(和光純薬工業株式会社)、テトラコナゾール(和光純薬工業株式会社)の1%w/vジメチルスルホオキシド溶液をそれぞれ調製した。この薬剤をジメチルスルホオキシドで希釈し、所定量を滅菌後のポテトデキストロース寒天培地に十分混合し、直径90mmのシャーレ内に15ml注ぎ込み、室温に放置した。なお、コントロールとして、ジメチルスルホオキシドのみを添加したポテトデキストロース寒天培地も同様に作成した。培地が固まった後、あらかじめ培養しておいた代表的な木材腐朽菌であるカワラタケ(Trametes versicolor)のコロニーから、菌糸を直径5mmのコルクボーラーで培地ごとくり抜き試験培地の中央に接種した。シャーレを25℃にて培養し、7日目に接種源から広がったコロニーの直径を測定し、上記式によってコントロールのコロニーの直径と比較した菌の生育阻害率を求め、実測生育阻害率として表した。結果を表2に示す。活性成分の混合物の理論有効率(理論生育阻害率)は、下記コルビーの式[R. S. Colby, Weeds 15, 20-22 (1967)]を用いて求め、実測有効率(理論生育阻害率)と比較した。この結果は、化合物Aとトリアゾール系殺菌剤とに相乗効果があることを明白に示している。
蒸留水を溶媒として、塩基性炭酸銅16質量%、モノエタノールアミン40質量%、安息香酸5質量%を含む木材保存薬剤を調製した。この木材保存薬剤に、少量のエタノールにあらかじめ溶解した化合物Aおよびエポキシコナゾールを、所定の濃度になるように添加した。
木材保存剤の実験室での腐朽評価用プロトコル(オーストララシアン木材保存委員会)(PROTOCOLS FOR ASSESSMENT OF WOOD PRESERVATIVES, LABORATORY DECAY(THE AUSTRALASIAN WOOD PRESERVATION COMMITTEE))に準拠し、この木材保存薬剤を所定濃度になるように蒸留水で希釈し、試験体ラジアタパイン辺材(20×20×20mm)に加圧注入した後、風乾し、プロトコルに従って耐侯操作を行った。この試験体をプロトコルに従い生育させたナミダタケ(Serpula lacrymans)の菌叢上に設置し、20℃で12週間腐朽させた後、試験前後の試験体の腐朽による質量減少率を測定した。なお、結果は1条件につきいずれも試験体9個を用いて平均値を算出したものである。結果を表3に示す。化合物Aを用いることにより、低薬量にて効果の高い木材保存用防腐剤が得られ、さらにトリアゾール系殺菌剤を同時に配合することで、極めて低薬量にて効果の高い木材保存用防腐剤が得られることが明らかとなった。
Claims (6)
- さらに、トリアゾール系殺菌剤を含有する請求項1に記載の木材保存用防腐剤。
- トリアゾール系殺菌剤が、シプロコナゾール、エポキシコナゾール、およびテトラコナゾールから選ばれる1以上の殺菌剤である請求項2に記載の木材保存用防腐剤。
- さらに、他の抗生物性化合物を含む請求項1〜3のいずれかに記載の木材保存用防腐剤。
- 抗生物性化合物が、銅化合物から選択されるものである請求項4に記載の木材保存用防腐剤。
- 請求項1〜5のいずれかに記載の防腐剤を用いて処理を行うことを特徴とする木材保存処理方法。
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JP2010544114A JP4785154B2 (ja) | 2008-12-25 | 2009-12-24 | 木材保存用防腐剤及び木材処理方法 |
PCT/JP2009/071405 WO2010074129A1 (ja) | 2008-12-25 | 2009-12-24 | 木材保存用防腐剤及び木材処理方法 |
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US (1) | US20110256238A1 (ja) |
JP (1) | JP4785154B2 (ja) |
AU (1) | AU2009331207B2 (ja) |
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JP5536434B2 (ja) * | 2009-12-14 | 2014-07-02 | 株式会社エス・ディー・エス バイオテック | 木材の保存処理方法及び保存処理木材 |
BR112016008555A8 (pt) | 2013-10-18 | 2020-03-10 | Basf Agrochemical Products Bv | usos do composto carboxamida ativo pesticida e método de proteção de material de propagação vegetal |
UA124503C2 (uk) | 2013-10-18 | 2021-09-29 | Басф Агрокемікал Продактс Б.В. | Інсектицидно активні суміші, які містять сполуку карбоксаміду |
EP3942933A1 (en) * | 2013-10-18 | 2022-01-26 | BASF Agrochemical Products B.V. | Agricultural mixtures comprising carboxamide compound |
WO2019224794A1 (en) * | 2018-05-24 | 2019-11-28 | Indofil Industries Limited | Synergistic fungicidal composition and a process for preparation thereof |
JPWO2022264768A1 (ja) * | 2021-06-15 | 2022-12-22 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57149204A (en) * | 1981-03-10 | 1982-09-14 | Kumiai Chem Ind Co Ltd | Preservative and mildew-proofing agent of wood |
JPS5885803A (ja) * | 1981-11-16 | 1983-05-23 | Ihara Chem Ind Co Ltd | 木材防腐剤 |
JPS60197603A (ja) * | 1984-03-19 | 1985-10-07 | Nippon Nohyaku Co Ltd | ナミダタケ防除剤 |
JPH01143804A (ja) * | 1987-12-01 | 1989-06-06 | Aguro Kanesho Kk | 農園芸用殺菌剤 |
JPH04134003A (ja) * | 1990-09-25 | 1992-05-07 | Ihara Chem Ind Co Ltd | 水中生物付着防止剤 |
Family Cites Families (2)
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JPH1143804A (ja) * | 1997-07-22 | 1999-02-16 | Koko Beniiniyu Japan:Kk | 靴 下 |
US20090162410A1 (en) * | 2007-12-21 | 2009-06-25 | Jun Zhang | Process for preparing fine particle dispersion for wood preservation |
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2009
- 2009-12-24 JP JP2010544114A patent/JP4785154B2/ja active Active
- 2009-12-24 US US13/142,166 patent/US20110256238A1/en not_active Abandoned
- 2009-12-24 NZ NZ594165A patent/NZ594165A/xx not_active IP Right Cessation
- 2009-12-24 AU AU2009331207A patent/AU2009331207B2/en not_active Ceased
- 2009-12-24 WO PCT/JP2009/071405 patent/WO2010074129A1/ja active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57149204A (en) * | 1981-03-10 | 1982-09-14 | Kumiai Chem Ind Co Ltd | Preservative and mildew-proofing agent of wood |
JPS5885803A (ja) * | 1981-11-16 | 1983-05-23 | Ihara Chem Ind Co Ltd | 木材防腐剤 |
JPS60197603A (ja) * | 1984-03-19 | 1985-10-07 | Nippon Nohyaku Co Ltd | ナミダタケ防除剤 |
JPH01143804A (ja) * | 1987-12-01 | 1989-06-06 | Aguro Kanesho Kk | 農園芸用殺菌剤 |
JPH04134003A (ja) * | 1990-09-25 | 1992-05-07 | Ihara Chem Ind Co Ltd | 水中生物付着防止剤 |
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WO2010074129A1 (ja) | 2010-07-01 |
NZ594165A (en) | 2013-10-25 |
US20110256238A1 (en) | 2011-10-20 |
AU2009331207B2 (en) | 2014-12-18 |
JPWO2010074129A1 (ja) | 2012-06-21 |
AU2009331207A1 (en) | 2011-08-11 |
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