FI119512B - Puunsuoja-aineena käytettävät oksatiatsiinit - Google Patents
Puunsuoja-aineena käytettävät oksatiatsiinit Download PDFInfo
- Publication number
- FI119512B FI119512B FI960829A FI960829A FI119512B FI 119512 B FI119512 B FI 119512B FI 960829 A FI960829 A FI 960829A FI 960829 A FI960829 A FI 960829A FI 119512 B FI119512 B FI 119512B
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- eller
- alkoxy
- hydrogen
- phenyl
- Prior art date
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- 239000002023 wood Substances 0.000 title claims abstract description 52
- 239000003755 preservative agent Substances 0.000 title description 2
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical class O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000002131 composite material Substances 0.000 claims abstract description 11
- -1 cyano, acetyl Chemical group 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 79
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000010875 treated wood Substances 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- SKSXVQHWKWTNPO-UHFFFAOYSA-N 3-bromo-2-chlorobenzonitrile Chemical compound ClC1=C(Br)C=CC=C1C#N SKSXVQHWKWTNPO-UHFFFAOYSA-N 0.000 claims 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 claims 1
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical group ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims 1
- 210000002445 nipple Anatomy 0.000 claims 1
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 230000002103 transcriptional effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 230000007774 longterm Effects 0.000 abstract description 3
- 238000004321 preservation Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 45
- 230000002538 fungal effect Effects 0.000 description 27
- 241000233866 Fungi Species 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003171 wood protecting agent Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000002775 capsule Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
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- 229920001817 Agar Polymers 0.000 description 6
- 241000223678 Aureobasidium pullulans Species 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
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- 210000002784 stomach Anatomy 0.000 description 5
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- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 241000223261 Trichoderma viride Species 0.000 description 4
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- FMYSHKHSQFXYRS-UHFFFAOYSA-N 1,4,2-oxathiazine Chemical compound O1C=CSC=N1 FMYSHKHSQFXYRS-UHFFFAOYSA-N 0.000 description 3
- 244000087596 Aglaonema pictum Species 0.000 description 3
- 241001149955 Cladosporium cladosporioides Species 0.000 description 3
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- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 3
- 241001515915 Ophiostoma piliferum Species 0.000 description 3
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- 235000008124 Picea excelsa Nutrition 0.000 description 3
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- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 235000011613 Pinus brutia Nutrition 0.000 description 3
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- 241001279364 Stachybotrys chartarum Species 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- VXBRQDSRTRLHPJ-UHFFFAOYSA-N 5,6-dihydro-1,4,2-oxathiazine Chemical compound C1CSC=NO1 VXBRQDSRTRLHPJ-UHFFFAOYSA-N 0.000 description 2
- BZHJKKOWVQHASL-UHFFFAOYSA-N 6-methyl-3-thiophen-2-yl-5,6-dihydro-1,4,2-oxathiazine 4,4-dioxide Chemical compound O1C(C)CS(=O)(=O)C(C=2SC=CC=2)=N1 BZHJKKOWVQHASL-UHFFFAOYSA-N 0.000 description 2
- HCQYXRNPRGHWBC-UHFFFAOYSA-N 6-methyl-3-thiophen-2-yl-5,6-dihydro-2h-1,2,4-oxadiazine Chemical compound N1OC(C)CN=C1C1=CC=CS1 HCQYXRNPRGHWBC-UHFFFAOYSA-N 0.000 description 2
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
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- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
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- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
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- YOSDUYOUGMGRNL-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5,6-dihydro-1,4,2-oxathiazine Chemical compound S1C(Cl)=CC=C1C1=NOCCS1 YOSDUYOUGMGRNL-UHFFFAOYSA-N 0.000 description 1
- QPAACYVYXIHGMJ-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5,6-dihydro-1,4,2-oxathiazine 4,4-dioxide Chemical compound S1C(Cl)=CC=C1C1=NOCCS1(=O)=O QPAACYVYXIHGMJ-UHFFFAOYSA-N 0.000 description 1
- QOOBXUSPGYRDNN-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5,6-dihydro-1,4,2-oxathiazine 4-oxide Chemical compound S1C(Cl)=CC=C1C1=NOCCS1=O QOOBXUSPGYRDNN-UHFFFAOYSA-N 0.000 description 1
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- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
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- PIZBMRZTDVXNOY-UHFFFAOYSA-N 6-methyl-3-thiophen-2-yl-5,6-dihydro-1,4,2-oxathiazine 4-oxide Chemical compound O1C(C)CS(=O)C(C=2SC=CC=2)=N1 PIZBMRZTDVXNOY-UHFFFAOYSA-N 0.000 description 1
- 241000266325 Alternaria atra Species 0.000 description 1
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- 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
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- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
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- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—Six-membered rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11138693A | 1993-08-24 | 1993-08-24 | |
| US11138693 | 1993-08-24 | ||
| US9409702 | 1994-08-24 | ||
| PCT/US1994/009702 WO1995006043A1 (en) | 1993-08-24 | 1994-08-24 | Wood preservative oxathiazines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI960829A0 FI960829A0 (fi) | 1996-02-23 |
| FI960829L FI960829L (fi) | 1996-04-19 |
| FI119512B true FI119512B (fi) | 2008-12-15 |
Family
ID=22338232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI960829A FI119512B (fi) | 1993-08-24 | 1996-02-23 | Puunsuoja-aineena käytettävät oksatiatsiinit |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US5777110A (cs) |
| EP (1) | EP0715625B1 (cs) |
| JP (1) | JP2761441B2 (cs) |
| KR (1) | KR100335756B1 (cs) |
| CN (1) | CN1059440C (cs) |
| AT (1) | ATE154017T1 (cs) |
| AU (1) | AU688371B2 (cs) |
| BR (1) | BR9407561A (cs) |
| CA (1) | CA2169654C (cs) |
| CZ (1) | CZ291537B6 (cs) |
| DE (1) | DE69403667T2 (cs) |
| DK (1) | DK0715625T3 (cs) |
| ES (1) | ES2102878T3 (cs) |
| FI (1) | FI119512B (cs) |
| GR (1) | GR3024590T3 (cs) |
| HU (1) | HU215235B (cs) |
| MX (1) | MX9406411A (cs) |
| MY (1) | MY137123A (cs) |
| NO (1) | NO305837B1 (cs) |
| NZ (1) | NZ273187A (cs) |
| PL (1) | PL180262B1 (cs) |
| RU (1) | RU2127266C1 (cs) |
| TW (1) | TW279784B (cs) |
| WO (1) | WO1995006043A1 (cs) |
| ZA (1) | ZA946450B (cs) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0823461A1 (en) * | 1996-08-07 | 1998-02-11 | Sigma Coatings B.V. | Increasing the self-polishing properties of antifouling paints |
| AU745587B2 (en) * | 1997-10-15 | 2002-03-21 | Bayer Aktiengesellschaft | Synergistic compositions comprising an oxathiazine and a benzothiophene-2-carboxamide-S,S-dioxide |
| US5965749A (en) * | 1998-03-16 | 1999-10-12 | Uniroyal Chemical Company, Inc. | Process for synthesizing substituted 2-benzo [b]thiophenecarboxylic acids and salts thereof |
| GB9826245D0 (en) * | 1998-11-30 | 1999-01-20 | Hickson Int Plc | Wood preserative formulations |
| US20060160791A1 (en) * | 1999-11-30 | 2006-07-20 | Gareth Williams | Wood preservative formulations |
| JP2002265310A (ja) * | 2001-03-06 | 2002-09-18 | Nagase Chemtex Corp | 抗微生物剤組成物 |
| CN1269401C (zh) | 2001-11-08 | 2006-08-16 | 詹森药业有限公司 | 含有4—溴—2—(4—氯苯基)—5—(三氟甲基)—1h—吡咯—3—腈的增效性抗污臭组合物 |
| WO2004011215A2 (en) * | 2002-07-26 | 2004-02-05 | Osmose, Inc. | Polymeric wood preservative compositions |
| US8637089B2 (en) * | 2003-04-09 | 2014-01-28 | Osmose, Inc. | Micronized wood preservative formulations |
| EP1624757A4 (en) | 2003-04-09 | 2007-07-04 | Osmose Inc | MICRONIZED WOOD CONSERVATIVE FORMULATIONS |
| US6960669B2 (en) | 2003-09-10 | 2005-11-01 | Crompton Co./Cie | Utilization of phosphorus pentasulfide in thionylations using phase transfer catalysis |
| WO2007014012A2 (en) * | 2005-07-21 | 2007-02-01 | Osmose, Inc. | Compositions and methods for wood preservation |
| NZ566638A (en) | 2006-02-01 | 2011-01-28 | Janssen Pharmaceutica Nv | Combinations of 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile and metal compounds |
| EP2051942B1 (en) | 2006-08-07 | 2009-11-04 | Janssen Pharmaceutica N.V. | Combinations of 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)- 1h-pyrrole-3-carbonitrile and oxidizing agents |
| US20080175913A1 (en) * | 2007-01-09 | 2008-07-24 | Jun Zhang | Wood preservative compositions comprising isothiazolone-pyrethroids |
| US20090162410A1 (en) * | 2007-12-21 | 2009-06-25 | Jun Zhang | Process for preparing fine particle dispersion for wood preservation |
| RU2400069C1 (ru) * | 2009-06-11 | 2010-09-27 | Галина Ивановна Эль-Регистан | Способ защиты материалов от микробного разрушения |
| MX2012014273A (es) | 2010-06-07 | 2013-03-22 | Novomedix Llc | Compuestos furanilo y su uso. |
| US20120142676A1 (en) | 2010-08-18 | 2012-06-07 | Gaik-Lean Chee | Oxathiazine and dithiine oxides as inhibitors of sulfhydryl-dependent biomolecules |
| CN102783502B (zh) * | 2012-08-22 | 2014-02-19 | 福建师范大学 | 一种竹材和竹制品专用防霉菌剂的制备及其应用 |
| CN107379175A (zh) * | 2017-09-07 | 2017-11-24 | 阜南县大自然工艺品有限公司 | 一种榆木工艺品的加工方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691015A (en) * | 1951-01-09 | 1954-10-05 | Goodrich Co B F | N-(4-thiazolinyl-2) sulfenimides |
| DE2001017C3 (de) * | 1970-01-10 | 1978-05-18 | Hoechst Ag, 6000 Frankfurt | 3,4-Dihydro-1,23-oxathiazin-4on-2,2-dioxide, ihre Herstellung und Verwendung |
| US4376513A (en) * | 1980-06-30 | 1983-03-15 | The Toro Company | Irrigation stream splitter |
| CA1273921A (en) * | 1982-09-28 | 1990-09-11 | Walter G. Brouwer | 3-aryl-5, 6-dihydro-1, 4, 2-oxathiazines and their oxides |
| US4569690A (en) * | 1982-09-28 | 1986-02-11 | Uniroyal, Inc. | 3-Aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides |
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-
1994
- 1994-08-23 MX MX9406411A patent/MX9406411A/es not_active IP Right Cessation
- 1994-08-23 MY MYPI94002201A patent/MY137123A/en unknown
- 1994-08-24 CA CA002169654A patent/CA2169654C/en not_active Expired - Fee Related
- 1994-08-24 ZA ZA946450A patent/ZA946450B/xx unknown
- 1994-08-24 BR BR9407561A patent/BR9407561A/pt not_active IP Right Cessation
- 1994-08-24 WO PCT/US1994/009702 patent/WO1995006043A1/en active IP Right Grant
- 1994-08-24 NZ NZ273187A patent/NZ273187A/en not_active IP Right Cessation
- 1994-08-24 ES ES94926617T patent/ES2102878T3/es not_active Expired - Lifetime
- 1994-08-24 RU RU96105384A patent/RU2127266C1/ru not_active IP Right Cessation
- 1994-08-24 US US08/295,117 patent/US5777110A/en not_active Expired - Lifetime
- 1994-08-24 CN CN94193747A patent/CN1059440C/zh not_active Expired - Fee Related
- 1994-08-24 EP EP94926617A patent/EP0715625B1/en not_active Expired - Lifetime
- 1994-08-24 JP JP7507780A patent/JP2761441B2/ja not_active Expired - Fee Related
- 1994-08-24 AT AT94926617T patent/ATE154017T1/de active
- 1994-08-24 DE DE69403667T patent/DE69403667T2/de not_active Expired - Lifetime
- 1994-08-24 KR KR1019960700888A patent/KR100335756B1/ko not_active Expired - Fee Related
- 1994-08-24 AU AU76401/94A patent/AU688371B2/en not_active Ceased
- 1994-08-24 PL PL94313136A patent/PL180262B1/pl not_active IP Right Cessation
- 1994-08-24 CZ CZ1996560A patent/CZ291537B6/cs not_active IP Right Cessation
- 1994-08-24 DK DK94926617.5T patent/DK0715625T3/da active
- 1994-08-24 HU HU9600437A patent/HU215235B/hu not_active IP Right Cessation
- 1994-09-22 TW TW083108750A patent/TW279784B/zh not_active IP Right Cessation
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1996
- 1996-02-21 NO NO960696A patent/NO305837B1/no not_active IP Right Cessation
- 1996-02-23 FI FI960829A patent/FI119512B/fi not_active IP Right Cessation
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1997
- 1997-09-02 GR GR970402234T patent/GR3024590T3/el unknown
- 1997-11-12 US US08/967,856 patent/US6372297B1/en not_active Expired - Fee Related
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