PL94736B1 - Sposob wytwarzania 2-triazolo(3,4-b)-benzotiazoli - Google Patents
Sposob wytwarzania 2-triazolo(3,4-b)-benzotiazoli Download PDFInfo
- Publication number
- PL94736B1 PL94736B1 PL1975178572A PL17857275A PL94736B1 PL 94736 B1 PL94736 B1 PL 94736B1 PL 1975178572 A PL1975178572 A PL 1975178572A PL 17857275 A PL17857275 A PL 17857275A PL 94736 B1 PL94736 B1 PL 94736B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compound
- meaning given
- given above
- general formula
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 alkyl radical Chemical class 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 229910052731 fluorine Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- BGFURDBGMRKOTL-UHFFFAOYSA-N [1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical class C1=CC=C2N3C=NN=C3SC2=C1 BGFURDBGMRKOTL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 13
- 239000002585 base Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011734 sodium Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 244000053095 fungal pathogen Species 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GJGRFPDNXNXBLC-UHFFFAOYSA-N 1-acetamido-3-(2-chlorophenyl)thiourea Chemical compound CC(=O)NNC(=S)NC1=CC=CC=C1Cl GJGRFPDNXNXBLC-UHFFFAOYSA-N 0.000 description 1
- UTIJPISSCPYYOL-UHFFFAOYSA-N 1-chloro-2-isothiocyanato-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(N=C=S)=C1 UTIJPISSCPYYOL-UHFFFAOYSA-N 0.000 description 1
- OAGDRIUTLPDSMJ-UHFFFAOYSA-N 1-fluoro-2-isothiocyanatobenzene Chemical compound FC1=CC=CC=C1N=C=S OAGDRIUTLPDSMJ-UHFFFAOYSA-N 0.000 description 1
- ODOTYLQYSDVPMA-UHFFFAOYSA-N 1-iodo-2-isothiocyanatobenzene Chemical class IC1=CC=CC=C1N=C=S ODOTYLQYSDVPMA-UHFFFAOYSA-N 0.000 description 1
- XMEQXRMNVMZFAB-UHFFFAOYSA-N 1-methyl-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound C1=CC=C2N3C(C)=NN=C3SC2=C1 XMEQXRMNVMZFAB-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- CUHCBWKQRDWQMN-UHFFFAOYSA-N 4-ethyl-2,5-dimethylheptane Chemical compound CCC(C)C(CC)CC(C)C CUHCBWKQRDWQMN-UHFFFAOYSA-N 0.000 description 1
- SBESMWZBVQPWTQ-UHFFFAOYSA-N 5-heptyl-1h-1,2,4-triazole Chemical compound CCCCCCCC1=NC=NN1 SBESMWZBVQPWTQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000010676 Ocimum basilicum Nutrition 0.000 description 1
- 240000007926 Ocimum gratissimum Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- MEXKFCWMWJZDMF-UHFFFAOYSA-N n,n-dibutylacetamide Chemical compound CCCCN(C(C)=O)CCCC MEXKFCWMWJZDMF-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical group [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical group [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/449,141 US3937713A (en) | 1974-03-07 | 1974-03-07 | Process for the preparation of s-triazolo[3,4-b]benzothiazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL94736B1 true PL94736B1 (pl) | 1977-08-31 |
Family
ID=23783026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975178572A PL94736B1 (pl) | 1974-03-07 | 1975-03-06 | Sposob wytwarzania 2-triazolo(3,4-b)-benzotiazoli |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US3937713A (en, 2012) |
| JP (1) | JPS5821916B2 (en, 2012) |
| AT (1) | AT344164B (en, 2012) |
| BE (1) | BE826343A (en, 2012) |
| BG (1) | BG26532A3 (en, 2012) |
| BR (1) | BR7501346A (en, 2012) |
| CA (1) | CA1048506A (en, 2012) |
| CH (2) | CH620930A5 (en, 2012) |
| CS (1) | CS183785B2 (en, 2012) |
| DD (1) | DD118284A5 (en, 2012) |
| DE (1) | DE2509843A1 (en, 2012) |
| DK (1) | DK91075A (en, 2012) |
| EG (1) | EG11669A (en, 2012) |
| ES (1) | ES435429A1 (en, 2012) |
| FR (1) | FR2269531B1 (en, 2012) |
| GB (2) | GB1506022A (en, 2012) |
| HU (3) | HU174300B (en, 2012) |
| IE (1) | IE40755B1 (en, 2012) |
| IL (3) | IL46759A (en, 2012) |
| IN (1) | IN141164B (en, 2012) |
| IT (1) | IT1049533B (en, 2012) |
| NL (1) | NL7502789A (en, 2012) |
| NZ (1) | NZ176843A (en, 2012) |
| PH (4) | PH12940A (en, 2012) |
| PL (1) | PL94736B1 (en, 2012) |
| RO (2) | RO66265B (en, 2012) |
| SE (1) | SE399895B (en, 2012) |
| TR (1) | TR18295A (en, 2012) |
| YU (2) | YU48381A (en, 2012) |
| ZA (1) | ZA751390B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3974286A (en) * | 1975-02-07 | 1976-08-10 | Eli Lilly And Company | S-Triazolo [5,1-b]benzothiazoles as fungicidal agents |
| US4144233A (en) * | 1977-02-16 | 1979-03-13 | The Dow Chemical Company | Method for preparing benzo-(1,3,4)-benzotriazepines |
| DE3015090A1 (de) * | 1980-04-19 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | ]-(trihalogenmethyl-sulfenyl)-4-aryl-1,2,4-triazolidin-5-one, verfahren zu ihrer herstellung, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit diesen verbindungen |
| US4761415A (en) * | 1986-08-28 | 1988-08-02 | Smithkline Beckman Corporation | Dopamine-β-hydroxylase inhibitors |
| US5202488A (en) * | 1991-04-15 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Method for the manufacture of 3-aminophenol |
| RU2223275C1 (ru) * | 2002-12-04 | 2004-02-10 | Мордовский государственный университет им. Н.П. Огарёва | Способ получения [1,2,4] триазоло [3,4-в] [1,3] бензтиазол-3 (2Н)-тиона |
| WO2005090320A2 (en) * | 2004-03-12 | 2005-09-29 | Wyeth | Triazole derivatives and method of using the same to treat hiv infections |
| CN102321103B (zh) * | 2011-07-22 | 2013-11-13 | 浙江工业大学 | 一种5-甲基-1,2,4-三氮唑并[3,4-b]苯并噻唑衍生物及其应用 |
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1974
- 1974-03-07 US US05/449,141 patent/US3937713A/en not_active Expired - Lifetime
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1975
- 1975-03-05 EG EG117A patent/EG11669A/xx active
- 1975-03-05 CS CS7500001487A patent/CS183785B2/cs unknown
- 1975-03-06 DE DE19752509843 patent/DE2509843A1/de not_active Withdrawn
- 1975-03-06 TR TR18295A patent/TR18295A/xx unknown
- 1975-03-06 RO RO81568A patent/RO66265B/ro unknown
- 1975-03-06 BR BR1346/75A patent/BR7501346A/pt unknown
- 1975-03-06 CA CA75221381A patent/CA1048506A/en not_active Expired
- 1975-03-06 NZ NZ176843A patent/NZ176843A/xx unknown
- 1975-03-06 PL PL1975178572A patent/PL94736B1/pl unknown
- 1975-03-06 IL IL46759A patent/IL46759A/xx unknown
- 1975-03-06 GB GB44476/77A patent/GB1506022A/en not_active Expired
- 1975-03-06 HU HU75EI756A patent/HU174300B/hu unknown
- 1975-03-06 HU HU75EI00000602A patent/HU171575B/hu unknown
- 1975-03-06 RO RO7590478A patent/RO70739A/ro unknown
- 1975-03-06 BE BE1006503A patent/BE826343A/xx not_active IP Right Cessation
- 1975-03-06 HU HU75EI757A patent/HU174301B/hu unknown
- 1975-03-06 ZA ZA00751390A patent/ZA751390B/xx unknown
- 1975-03-06 SE SE7502536A patent/SE399895B/xx not_active IP Right Cessation
- 1975-03-06 GB GB9270/75A patent/GB1506021A/en not_active Expired
- 1975-03-06 DK DK91075*#A patent/DK91075A/da unknown
- 1975-03-06 IT IT21006/75A patent/IT1049533B/it active
- 1975-03-07 BG BG029186A patent/BG26532A3/xx unknown
- 1975-03-07 ES ES435429A patent/ES435429A1/es not_active Expired
- 1975-03-07 JP JP50028593A patent/JPS5821916B2/ja not_active Expired
- 1975-03-07 CH CH295475A patent/CH620930A5/de not_active IP Right Cessation
- 1975-03-07 AT AT179075A patent/AT344164B/de not_active IP Right Cessation
- 1975-03-07 DD DD184649A patent/DD118284A5/xx unknown
- 1975-03-07 NL NL7502789A patent/NL7502789A/xx not_active Application Discontinuation
- 1975-03-07 PH PH16886A patent/PH12940A/en unknown
- 1975-03-07 IN IN449/CAL/75A patent/IN141164B/en unknown
- 1975-03-07 FR FR7507281A patent/FR2269531B1/fr not_active Expired
- 1975-03-26 IE IE485/75A patent/IE40755B1/xx unknown
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1977
- 1977-08-03 IL IL52642A patent/IL52642A0/xx unknown
- 1977-08-03 IL IL52641A patent/IL52641A0/xx unknown
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1978
- 1978-04-05 PH PH20978A patent/PH12494A/en unknown
- 1978-04-05 PH PH20977A patent/PH12478A/en unknown
- 1978-04-05 PH PH20981A patent/PH13353A/en unknown
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1979
- 1979-01-11 CH CH26279A patent/CH620219A5/de not_active IP Right Cessation
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1981
- 1981-02-25 YU YU00483/81A patent/YU48381A/xx unknown
- 1981-02-25 YU YU00482/81A patent/YU48281A/xx unknown
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