IL126645A - טריאזוליל מרקפטידים, תהליך להכנתם ותכשירים קוטלי חיידקים המכילים אותם - Google Patents
טריאזוליל מרקפטידים, תהליך להכנתם ותכשירים קוטלי חיידקים המכילים אותםInfo
- Publication number
- IL126645A IL126645A IL12664597A IL12664597A IL126645A IL 126645 A IL126645 A IL 126645A IL 12664597 A IL12664597 A IL 12664597A IL 12664597 A IL12664597 A IL 12664597A IL 126645 A IL126645 A IL 126645A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- formula
- halogen
- alkoxy
- moiety
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 64
- 230000003641 microbiacidal effect Effects 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000001425 triazolyl group Chemical group 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 146
- 239000011734 sodium Substances 0.000 claims abstract description 58
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 239000010949 copper Substances 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052802 copper Inorganic materials 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 7
- 239000011701 zinc Substances 0.000 claims abstract description 7
- YWMAPNNZOCSAPF-UHFFFAOYSA-N Nickel(1+) Chemical compound [Ni+] YWMAPNNZOCSAPF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940006444 nickel cation Drugs 0.000 claims abstract description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 5
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011777 magnesium Substances 0.000 claims abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011575 calcium Substances 0.000 claims abstract description 4
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- -1 fluoro-tert-butyl Chemical group 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical class SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000004679 hydroxides Chemical class 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 150000001875 compounds Chemical class 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000000126 substance Substances 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 238000012360 testing method Methods 0.000 description 32
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 22
- 239000005864 Sulphur Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000843 powder Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
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- 230000001681 protective effect Effects 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
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- 239000012074 organic phase Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 235000019270 ammonium chloride Nutrition 0.000 description 14
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical group 0.000 description 12
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 10
- 238000011081 inoculation Methods 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- 241000221787 Erysiphe Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 229920000151 polyglycol Polymers 0.000 description 9
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- 208000015181 infectious disease Diseases 0.000 description 8
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- 239000003208 petroleum Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
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- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 150000002170 ethers Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000003852 triazoles Chemical class 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 206010037888 Rash pustular Diseases 0.000 description 4
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
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- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19617282A DE19617282A1 (de) | 1996-04-30 | 1996-04-30 | Triazolyl-mercaptide |
PCT/EP1997/001996 WO1997041107A1 (de) | 1996-04-30 | 1997-04-21 | Triazolyl-mercaptide und ihre verwendung als mikrobizide |
Publications (2)
Publication Number | Publication Date |
---|---|
IL126645A0 IL126645A0 (en) | 1999-08-17 |
IL126645A true IL126645A (he) | 2002-11-10 |
Family
ID=7792889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL12664597A IL126645A (he) | 1996-04-30 | 1997-04-21 | טריאזוליל מרקפטידים, תהליך להכנתם ותכשירים קוטלי חיידקים המכילים אותם |
Country Status (13)
Country | Link |
---|---|
US (1) | US6057353A (he) |
EP (1) | EP0906292B1 (he) |
JP (1) | JP2000509052A (he) |
KR (1) | KR20000064929A (he) |
CN (1) | CN1216984A (he) |
AU (1) | AU2700597A (he) |
BR (1) | BR9708882A (he) |
DE (2) | DE19617282A1 (he) |
DK (1) | DK0906292T3 (he) |
ES (1) | ES2198568T3 (he) |
IL (1) | IL126645A (he) |
PL (1) | PL329484A1 (he) |
WO (1) | WO1997041107A1 (he) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19734185A1 (de) * | 1997-08-07 | 1999-02-11 | Bayer Ag | Triazolinthion-Derivat |
DE10233171A1 (de) * | 2002-07-22 | 2004-02-12 | Bayer Cropscience Ag | Kristallmodifikation II des 2-[2-(Chlor-cyclopropyl)-3-(2-chlorphenyl)-2-hydroxy-propyl]-2,4dihydro-3H-1,2,4-triazol-3-thions |
KR20100093127A (ko) * | 2007-12-19 | 2010-08-24 | 바스프 에스이 | 아졸릴메틸옥시란, 이의 용도 및 이를 포함하는 작용제 |
US20100273651A1 (en) * | 2007-12-19 | 2010-10-28 | Basf Se | Azolylmethyloxiranes, use Thereof and Agents Containing the Same |
EP2224812A2 (de) * | 2007-12-19 | 2010-09-08 | Basf Se | Azolylmethyloxirane, ihre verwendung sowie sie enthaltende mittel |
US20110190122A1 (en) * | 2008-10-07 | 2011-08-04 | Basf Se | Triazole and Imidazole Compounds, Use Thereof and Agents Containing Them |
CN102177143A (zh) * | 2008-10-07 | 2011-09-07 | 巴斯夫欧洲公司 | 三唑和咪唑化合物、其应用和含有它们的试剂 |
AR076429A1 (es) * | 2009-04-24 | 2011-06-08 | Basf Se | Compuestos de triazol que llevan un sustituyente de azufre iv |
TW201043139A (en) * | 2009-04-24 | 2010-12-16 | Basf Se | Triazole compounds carrying a sulfur substituent III |
WO2010149414A1 (en) * | 2009-04-24 | 2010-12-29 | Basf Se | 5-mercapto-[1, 2, 4] triazolylmethyl-cyclopentanol compounds and their agricultural and pharmaceutical uses |
WO2010122167A1 (en) * | 2009-04-24 | 2010-10-28 | Basf Se | 5 -mercapto- [1, 2, 4] triazolylmethyl-cyclopentanol compounds and their agricultural and pharmaceutical uses |
WO2010142779A1 (en) | 2009-06-12 | 2010-12-16 | Basf Se | Antifungal 1,2,4-triazolyl derivatives having a 5- sulfur substituent |
AU2010261888A1 (en) * | 2009-06-18 | 2012-01-19 | Basf Se | Fungicidal mixtures |
KR20120062679A (ko) | 2009-06-18 | 2012-06-14 | 바스프 에스이 | 황 치환기를 보유하는 트리아졸 화합물 |
US20120088664A1 (en) * | 2009-06-18 | 2012-04-12 | Basf Se | Antifungal 1,2,4-triazolyl derivatives having a 5-sulfur subtituent |
WO2010146116A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
JP2012530110A (ja) * | 2009-06-18 | 2012-11-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 抗菌性1,2,4−トリアゾリル誘導体 |
WO2010146115A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
US20120108422A1 (en) | 2009-06-18 | 2012-05-03 | Basf Se | Antifungal 1,2,4-triazolyl Derivatives |
WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
BR112012001001A2 (pt) | 2009-07-14 | 2016-11-16 | Basf Se | compositos azol das formulas i e ii, compostos das formulas i e i, compostos de formula ix, composição agricola, uso de um composto farmaceutica, metodo para tratar infecções de câncer ou virus para combater fungos zoopatigênicos ou humanopatogenicos |
WO2011069912A1 (de) | 2009-12-07 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
WO2011069916A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung als fungizide sowie sie enthaltende mittel |
WO2011069894A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
BR112012015040A2 (pt) | 2009-12-18 | 2015-09-22 | Basf Se | processo para a preparação de grupos tio-triazol substituídos da fórmula geral (i) e compostos (lla) |
US8729272B2 (en) | 2010-03-16 | 2014-05-20 | Basf Se | Process using grignard reagents |
CN102958923A (zh) | 2010-05-27 | 2013-03-06 | 拜耳知识产权有限责任公司 | 新型杂环链烷醇衍生物 |
CN102947282B (zh) | 2010-05-27 | 2016-06-01 | 拜耳知识产权有限责任公司 | 作为杀真菌剂的杂环链烷醇衍生物 |
CN102985414B (zh) | 2010-05-27 | 2016-05-18 | 拜耳知识产权有限责任公司 | 作为杀真菌剂的杂环硫代取代链烷醇衍生物 |
CA2800626A1 (en) | 2010-05-27 | 2011-12-01 | Bayer Intellectual Property Gmbh | Heterocyclic alkanol derivatives as fungicides |
JP5872548B2 (ja) | 2010-05-27 | 2016-03-01 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 殺菌剤としてのヘテロ環式アルカノール誘導体 |
JP2013542199A (ja) | 2010-09-30 | 2013-11-21 | ビーエーエスエフ ソシエタス・ヨーロピア | チオトリアゾロ基含有化合物の合成方法 |
WO2012130823A1 (en) | 2011-03-30 | 2012-10-04 | Basf Se | Suspension concentrates |
CA2856711A1 (en) | 2011-11-25 | 2013-05-30 | Bayer Intellectual Property Gmbh | Novel heterocyclic alkanol-derivatives |
JP2016522800A (ja) | 2013-04-12 | 2016-08-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 新規トリアゾリンチオン誘導体 |
US20170197910A1 (en) * | 2014-07-18 | 2017-07-13 | Bayer Cropscience Aktiengesellschaft | Substituted vinyl and alkynyl cyanocycloalkanols and vinyl and alkynyl cyanoheterocycloalkanols as active agents against abiotic plant stress |
CN105218419B (zh) * | 2015-10-14 | 2017-03-29 | 北京彤程创展科技有限公司 | 一种有机硫醇锌盐的制备方法 |
WO2018054832A1 (en) | 2016-09-22 | 2018-03-29 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
PL3541794T3 (pl) * | 2016-11-18 | 2022-01-17 | Corteva Agriscience Llc | 4-((6-(2-(2,4-difluorofenylo)-1,1-difluoro-2-hydroksy-3-(5-merkapto-1h-1,2,4-triazol-1- ilo)propylo)pirydyn-3-ylo)oksy)benzonitryl i sposoby wytwarzania |
MX2019009310A (es) | 2017-02-08 | 2019-12-09 | Bayer Ag | Derivados de triazoletiona. |
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US4048318A (en) * | 1972-01-11 | 1977-09-13 | Bayer Aktiengesellschaft | 1-Substituted-1,2,4-triazole fungicides |
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AR228764A1 (es) * | 1980-12-20 | 1983-04-15 | Bayer Ag | 1-azolil-3,3-dimetilalcan(c3-4)-2-onas y-2-oles,sustituidos,procedimiento para su produccion y composiciones protectoras de plantas fungicidas y reguladoras del crecimiento de las plantas a base de dichos compuestos |
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US5266585A (en) * | 1981-05-12 | 1993-11-30 | Ciba-Geigy Corporation | Arylphenyl ether derivatives, compositions containing these compounds and use thereof |
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IT1204773B (it) * | 1986-01-23 | 1989-03-10 | Montedison Spa | Azolilderivati fungicidi |
US4729986A (en) * | 1986-04-24 | 1988-03-08 | E. I. Du Pont De Nemours And Company | Fungicidal triazoles and imidazoles |
US5084465A (en) * | 1986-06-23 | 1992-01-28 | Du Pont Merck Pharmaceutical Company | Antifungal carbinols |
US4965281A (en) * | 1986-06-23 | 1990-10-23 | E. I. Du Pont De Nemours And Cmopany | Antifungal carbinols |
US4952232A (en) * | 1987-04-29 | 1990-08-28 | E. I. Du Pont De Nemours And Company | Antifungal carbinols |
EP0251086B1 (en) * | 1986-06-23 | 1993-03-17 | The Du Pont Merck Pharmaceutical Company | Antifungal carbinols |
US5087635A (en) * | 1986-07-02 | 1992-02-11 | Rohm And Haas Company | Alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles |
JPH0625140B2 (ja) * | 1986-11-10 | 1994-04-06 | 呉羽化学工業株式会社 | 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤 |
DE3812967A1 (de) * | 1987-06-24 | 1989-01-05 | Bayer Ag | Azolylmethyl-cyclopropyl-derivate |
DE3725397A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | 1,4-disubstituierte 1-azolyl-3,3-dimethylbutan-derivate |
US5256683A (en) * | 1988-12-29 | 1993-10-26 | Rhone-Poulenc Agrochimie | Fungicidal compositions containing (benzylidene)-azolylmethylcycloalkane |
CA2006309C (fr) * | 1988-12-29 | 2001-12-18 | Jean Hutt | Azolylmethylcyclopentane benzylidene fongicide |
US5308743A (en) * | 1989-06-29 | 1994-05-03 | Fuji Photo Film Co., Ltd. | Positive image-forming process utilizing glass substrate with oxide film of indium-tin alloy, coated with o-quinonediazide photoresist, with etching of the oxide film in the imagewise exposed areas |
EP0680813A1 (de) * | 1994-05-02 | 1995-11-08 | Ciba-Geigy Ag | Verfahren zur Herstellung von faserverstärkten Formmassen |
DE19528046A1 (de) * | 1994-11-21 | 1996-05-23 | Bayer Ag | Triazolyl-Derivate |
DE19520097A1 (de) * | 1995-06-01 | 1996-12-05 | Bayer Ag | Triazolylmethyl-oxirane |
DE19520095A1 (de) * | 1995-06-01 | 1996-12-05 | Bayer Ag | Mercapto-triazolyl-silane |
DE19520096A1 (de) * | 1995-06-01 | 1996-12-05 | Bayer Ag | Cycloalkan-benzyliden-Derivate |
DE19520098A1 (de) * | 1995-06-01 | 1996-12-05 | Bayer Ag | Triazolylmethyl-cyclopentanole |
DE19520593A1 (de) * | 1995-06-06 | 1996-12-12 | Bayer Ag | Mercapto-triazolyl-butanole |
DE19521030A1 (de) * | 1995-06-09 | 1996-12-12 | Bayer Ag | Mercapto-triazolyl-ethanole |
DE19521487A1 (de) * | 1995-06-13 | 1996-12-19 | Bayer Ag | Mercapto-triazolyl-dioxacycloalkane |
DE19528300A1 (de) * | 1995-08-02 | 1997-02-06 | Bayer Ag | 2-Phenylethyl-mercapto-triazole |
DE19529089A1 (de) * | 1995-08-08 | 1997-02-13 | Bayer Ag | Mercapto-triazolyl-nitrile |
DE19529091A1 (de) * | 1995-08-08 | 1997-02-13 | Bayer Ag | Mercapto-triazolyl-ketone |
-
1996
- 1996-04-30 DE DE19617282A patent/DE19617282A1/de not_active Withdrawn
-
1997
- 1997-04-21 JP JP9538530A patent/JP2000509052A/ja active Pending
- 1997-04-21 IL IL12664597A patent/IL126645A/he not_active IP Right Cessation
- 1997-04-21 KR KR1019980708258A patent/KR20000064929A/ko not_active Application Discontinuation
- 1997-04-21 AU AU27005/97A patent/AU2700597A/en not_active Abandoned
- 1997-04-21 US US09/171,733 patent/US6057353A/en not_active Expired - Fee Related
- 1997-04-21 BR BR9708882A patent/BR9708882A/pt not_active Application Discontinuation
- 1997-04-21 DE DE59710423T patent/DE59710423D1/de not_active Expired - Fee Related
- 1997-04-21 WO PCT/EP1997/001996 patent/WO1997041107A1/de not_active Application Discontinuation
- 1997-04-21 PL PL97329484A patent/PL329484A1/xx unknown
- 1997-04-21 EP EP97920729A patent/EP0906292B1/de not_active Expired - Lifetime
- 1997-04-21 DK DK97920729T patent/DK0906292T3/da active
- 1997-04-21 ES ES97920729T patent/ES2198568T3/es not_active Expired - Lifetime
- 1997-04-21 CN CN97194253A patent/CN1216984A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
IL126645A0 (en) | 1999-08-17 |
DE19617282A1 (de) | 1997-11-06 |
US6057353A (en) | 2000-05-02 |
WO1997041107A1 (de) | 1997-11-06 |
PL329484A1 (en) | 1999-03-29 |
AU2700597A (en) | 1997-11-19 |
DK0906292T3 (da) | 2003-10-27 |
DE59710423D1 (de) | 2003-08-14 |
KR20000064929A (ko) | 2000-11-06 |
CN1216984A (zh) | 1999-05-19 |
JP2000509052A (ja) | 2000-07-18 |
ES2198568T3 (es) | 2004-02-01 |
EP0906292B1 (de) | 2003-07-09 |
EP0906292A1 (de) | 1999-04-07 |
BR9708882A (pt) | 1999-08-03 |
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MM9K | Patent not in force due to non-payment of renewal fees |