CH626361A5 - Process for the preparation of novel 1,3-dioxolan-2-ylmethylimidazoles - Google Patents

Process for the preparation of novel 1,3-dioxolan-2-ylmethylimidazoles Download PDF

Info

Publication number: CH626361A5
Authority: CH; Switzerland
Prior art keywords: group; imidazole; parts; dioxolan; hno3
Prior art date: 1975-01-27

Application number

CH94276A

Other languages

German (de)

English (en)

Inventor

Jan Heeres

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-01-27

Filing date

1976-01-26

Publication date

1981-11-13

1975-01-27 Priority claimed from US05/544,157 external-priority patent/US3936470A/en

1976-01-26 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1976-10-15 Priority claimed from US05/732,826 external-priority patent/US4101666A/en

1981-11-13 Publication of CH626361A5 publication Critical patent/CH626361A5/de

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 10
QHXXHJLSKPQNAQ-UHFFFAOYSA-N 2-(1,3-dioxolan-2-ylmethyl)-1h-imidazole Chemical class N=1C=CNC=1CC1OCCO1 QHXXHJLSKPQNAQ-UHFFFAOYSA-N 0.000 title claims description 5
239000000460 chlorine Substances 0.000 claims description 162
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 110
-1 alkyl radical Chemical class 0.000 claims description 80
150000003839 salts Chemical class 0.000 claims description 52
150000001875 compounds Chemical class 0.000 claims description 50
239000002253 acid Substances 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
150000002460 imidazoles Chemical class 0.000 claims description 13
150000003254 radicals Chemical class 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000006331 halo benzoyl group Chemical group 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
239000003139 biocide Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000004970 halomethyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims 2
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
150000003851 azoles Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 58
239000000203 mixture Substances 0.000 description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 40
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 40
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 33
125000001309 chloro group Chemical group Cl* 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
229910002651 NO3 Inorganic materials 0.000 description 25
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 23
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 22
239000000047 product Substances 0.000 description 22
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
239000000284 extract Substances 0.000 description 19
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 19
239000007858 starting material Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000010992 reflux Methods 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
239000004305 biphenyl Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
125000005997 bromomethyl group Chemical group 0.000 description 13
239000000243 solution Substances 0.000 description 13
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000002585 base Substances 0.000 description 11
238000004440 column chromatography Methods 0.000 description 11
239000003480 eluent Substances 0.000 description 11
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
229910017604 nitric acid Inorganic materials 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
230000003385 bacteriostatic effect Effects 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
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 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
235000009518 sodium iodide Nutrition 0.000 description 7
239000007787 solid Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000000969 carrier Substances 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000005907 ketalization reaction Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
230000017066 negative regulation of growth Effects 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
241000233866 Fungi Species 0.000 description 3
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
150000001649 bromium compounds Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
230000000855 fungicidal effect Effects 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
229910001511 metal iodide Inorganic materials 0.000 description 3
239000002674 ointment Substances 0.000 description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QSWSKDXFOIOXKW-UHFFFAOYSA-N 1h-imidazole;nitric acid Chemical compound O[N+]([O-])=O.C1=CNC=N1 QSWSKDXFOIOXKW-UHFFFAOYSA-N 0.000 description 2
125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
MOQVHOPVBREXLY-UHFFFAOYSA-N 3h-dioxol-4-ylmethanol Chemical compound OCC1=COOC1 MOQVHOPVBREXLY-UHFFFAOYSA-N 0.000 description 2
235000001674 Agaricus brunnescens Nutrition 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
241000235395 Mucor Species 0.000 description 2
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
229940113088 dimethylacetamide Drugs 0.000 description 2
150000004862 dioxolanes Chemical class 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
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 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
150000002823 nitrates Chemical class 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000005507 spraying Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
BSGWEYJWOWEYBR-UHFFFAOYSA-N 1H-imidazole oxalic acid Chemical compound c1c[nH]cn1.c1c[nH]cn1.OC(=O)C(O)=O.OC(=O)C(O)=O.OC(=O)C(O)=O BSGWEYJWOWEYBR-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
YFRGZQBENALZLU-UHFFFAOYSA-N 2-(bromomethyl)-2-(2-chlorophenyl)-4-(4-chlorophenyl)-1,3-dioxolane Chemical compound C1=CC(Cl)=CC=C1C1OC(CBr)(C=2C(=CC=CC=2)Cl)OC1 YFRGZQBENALZLU-UHFFFAOYSA-N 0.000 description 1
OQLAYRXVDJTGHJ-UHFFFAOYSA-N 2-(bromomethyl)-2-(4-chlorophenyl)-4-phenyl-1,3-dioxolane Chemical compound C1=CC(Cl)=CC=C1C1(CBr)OC(C=2C=CC=CC=2)CO1 OQLAYRXVDJTGHJ-UHFFFAOYSA-N 0.000 description 1
FZSFLABXZKPYRI-UHFFFAOYSA-N 2-(bromomethyl)-4-[(4-bromophenoxy)methyl]-2-(2,3-dichlorophenyl)-1,3-dioxolane Chemical compound ClC1=CC=CC(C2(CBr)OC(COC=3C=CC(Br)=CC=3)CO2)=C1Cl FZSFLABXZKPYRI-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000006040 2-hexenyl group Chemical group 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241001225321 Aspergillus fumigatus Species 0.000 description 1
241001341614 Basidiobolus meristosporus Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
UTFLUQXHFRNOSW-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.ClC1=CC=C(C=C1)CCC1OC(OC1)(C1=C(C=C(C=C1)Cl)Cl)CN1C=NC=C1 Chemical compound C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.ClC1=CC=C(C=C1)CCC1OC(OC1)(C1=C(C=C(C=C1)Cl)Cl)CN1C=NC=C1 UTFLUQXHFRNOSW-UHFFFAOYSA-N 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
241000222178 Candida tropicalis Species 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
201000007336 Cryptococcosis Diseases 0.000 description 1
241000221204 Cryptococcus neoformans Species 0.000 description 1
241000186810 Erysipelothrix rhusiopathiae Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000144128 Lichtheimia corymbifera Species 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000893980 Microsporum canis Species 0.000 description 1
241000235575 Mortierella Species 0.000 description 1
MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 1
MMPOTNFPDMJTRR-UHFFFAOYSA-N OOOOOOOOOOO Chemical compound OOOOOOOOOOO MMPOTNFPDMJTRR-UHFFFAOYSA-N 0.000 description 1
ZQTQPYJGMWHXMO-UHFFFAOYSA-N OOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOO ZQTQPYJGMWHXMO-UHFFFAOYSA-N 0.000 description 1
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
241001531356 Phialophora verrucosa Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000235527 Rhizopus Species 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
241000607683 Salmonella enterica subsp. enterica serovar Pullorum Species 0.000 description 1
241000233667 Saprolegnia Species 0.000 description 1
241001149963 Sporothrix schenckii Species 0.000 description 1
241000191984 Staphylococcus haemolyticus Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
241001045770 Trichophyton mentagrophytes Species 0.000 description 1
241000223229 Trichophyton rubrum Species 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
150000001504 aryl thiols Chemical class 0.000 description 1
229940091771 aspergillus fumigatus Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
MGHMNKBPWSKDKH-UHFFFAOYSA-N benzoic acid;nitric acid Chemical compound O[N+]([O-])=O.OC(=O)C1=CC=CC=C1 MGHMNKBPWSKDKH-UHFFFAOYSA-N 0.000 description 1
ZITKUGXCXLDTFZ-UHFFFAOYSA-N benzonitrile;nitric acid Chemical compound O[N+]([O-])=O.N#CC1=CC=CC=C1 ZITKUGXCXLDTFZ-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000007799 cork Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229960003887 dichlorophen Drugs 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
230000029087 digestion Effects 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical group CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000006028 limestone Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000003595 mist Substances 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 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
230000009965 odorless effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
231100000194 ovacidal Toxicity 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229960003531 phenolsulfonphthalein Drugs 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 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
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
- 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
- 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
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen 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
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
- 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
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen 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
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- 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
- 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
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
- 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
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
- 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
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
- 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
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Agronomy & Crop Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH94276A 1975-01-27 1976-01-26 Process for the preparation of novel 1,3-dioxolan-2-ylmethylimidazoles CH626361A5 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US05/544,157 US3936470A (en)	1975-01-27	1975-01-27	1,3-Dioxolan-2-ylmethylimidazoles
US61986375A	1975-10-06	1975-10-06
US71099476A	1976-08-02	1976-08-02
US05/732,826 US4101666A (en)	1975-10-06	1976-10-15	1-(2-Ar-4-R-1,3-dioxolan-2-ylmethyl)imidazoles
US05/732,828 US4101664A (en)	1975-10-06	1976-10-15	1-(2-Ar-4-aryloxymethyl-1,3-dioxolan-2-ylmethyl)-imidazoles

Publications (1)

Publication Number	Publication Date
CH626361A5 true CH626361A5 (en)	1981-11-13

Family

ID=27541875

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH94276A CH626361A5 (en)	1975-01-27	1976-01-26	Process for the preparation of novel 1,3-dioxolan-2-ylmethylimidazoles

Country Status (8)

Country	Link
JP (1)	JPS6135196B2 (pl)
AU (1)	AU503981B2 (pl)
CA (1)	CA1065873A (pl)
CH (1)	CH626361A5 (pl)
DE (1)	DE2602770A1 (pl)
FR (1)	FR2298328A1 (pl)
GB (1)	GB1528639A (pl)
NL (1)	NL181906C (pl)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4160841A (en) *	1977-01-31	1979-07-10	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
US4144346A (en) *	1977-01-31	1979-03-13	Janssen Pharmaceutica N.V.	Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
CH637392A5 (en) *	1978-07-24	1983-07-29	Janssen Pharmaceutica Nv	2-Phenyl-2-azolylmethyl-cyclohexa(d)-1,3-dioxolane derivatives, processes for their preparation, compositions containing these active substances as microbicides, and their use
CH634842A5 (en) *	1978-07-25	1983-02-28	Janssen Pharmaceutica Nv	2-Phenyl-2-(1(H)-imidazolylmethyl)-1,3-dioxane derivatives, processes for their preparation, microbicides containing these active substances, and their use
US4277486A (en) *	1979-03-09	1981-07-07	Syntex (U.S.A.) Inc.	1-[(Substituted-naphthyl)ethyl]-imidazole derivatives
US4321272A (en) *	1980-08-25	1982-03-23	Syntex (U.S.A.) Inc.	Derivatives of substituted N-alkylimidazoles
DE3039087A1 (de)	1980-10-16	1982-05-19	Hoechst Ag, 6000 Frankfurt	1-(1,3-dioxolan-2-ylmethyl)-azole, ihre salze, verfahren zu ihrer herstellung und ihre verwendung
DE3166517D1 (de) *	1980-11-24	1984-11-08	Janssen Pharmaceutica Nv	Novel (2-aryl-4-phenylthioalkyl-1,3-dioxolan-2-yl-methyl)azole derivatives
DE3144318A1 (de) *	1981-11-07	1983-05-19	Bayer Ag, 5090 Leverkusen	2-imidazolylmethyl-2-phenyl-1, 3-dioxolane, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
JPS58134089A (ja) *	1982-02-02	1983-08-10	Yoshiki Hamada	１、３―ジオキソランベンザート誘導体，その製造法及び抗菌剤
DK354185A (da) *	1984-08-31	1986-03-01	Hoffmann La Roche	1,3-dioxolanderivater
US4940799A (en) *	1987-07-20	1990-07-10	Ciba-Geigy Corporation	Preparation of the diastereomeric mixture 2R,4S-1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
EP3925957A4 (en) *	2019-02-15	2022-11-02	Tohoku University	1,3-DIOXOLANE DERIVATIVE

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU557755A3 (ru) *	1968-08-19	1977-05-05	Янссен Фармасьютика Н.В. (Фирма)	Способ получени производных имидазола
US3575999A (en) *	1968-08-19	1971-04-20	Janssen Pharmaceutica Nv	Ketal derivatives of imidazole
US3658813A (en) *	1970-01-13	1972-04-25	Janssen Pharmaceutica Nv	1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles
DE2037610A1 (de) *	1970-07-29	1972-02-03	Bayer Ag	Neue alpha-substituierte Benzyl-azole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2041771C3 (de) *	1970-08-22	1979-07-26	Bayer Ag, 5090 Leverkusen	derivate

1975
- 1975-11-26 CA CA240,561A patent/CA1065873A/en not_active Expired
- 1975-12-10 NL NLAANVRAGE7514381,A patent/NL181906C/xx not_active IP Right Cessation
1976
- 1976-01-09 GB GB846/76A patent/GB1528639A/en not_active Expired
- 1976-01-12 FR FR7600614A patent/FR2298328A1/fr active Granted
- 1976-01-22 AU AU10496/76A patent/AU503981B2/en not_active Expired
- 1976-01-23 JP JP51006041A patent/JPS6135196B2/ja not_active Expired
- 1976-01-26 CH CH94276A patent/CH626361A5/de not_active IP Right Cessation
- 1976-01-26 DE DE19762602770 patent/DE2602770A1/de active Granted

Also Published As

Publication number	Publication date
FR2298328B1 (pl)	1978-08-18
NL181906B (nl)	1987-07-01
AU1049676A (en)	1977-07-28
CA1065873A (en)	1979-11-06
NL181906C (nl)	1987-12-01
NL7514381A (nl)	1976-07-29
GB1528639A (en)	1978-10-18
DE2602770A1 (de)	1976-07-29
JPS6135196B2 (pl)	1986-08-12
FR2298328A1 (fr)	1976-08-20
AU503981B2 (en)	1979-09-27
JPS51100073A (pl)	1976-09-03

Legal Events

Date	Code	Title	Description
1994-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US4156008A (en)	1979-05-22	1-(4-Alkyl-2-aryl-1,3-dioxolan-2-ylmethyl)-1H-imidazoles
EP0061051B1 (de)	1985-09-18	Substituierte Triazolylmethyl-oxirane, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Zwischenprodukte
CH615676A5 (en)	1980-02-15	Process for the preparation of novel 1-(beta-aryl)-ethyl-1H-1,2,4-triazol ketals and salts thereof and their use in fungicides
EP0111711B1 (de)	1987-03-18	Heterocyclisch substituierte Hydroxyalkyl-azolyl-Derivate
EP0199047B1 (de)	1988-10-05	Neue Iodpropargylether, ein Verfahren zu ihrer Herstellung und ihre Verwendung
DE1940388B2 (de)	1977-09-15	1-(beta-aryl) aethylimidazolderivate, ihre herstellung und diese enthaltende fungizide und bakterizide mittel
US4101664A (en)	1978-07-18	1-(2-Ar-4-aryloxymethyl-1,3-dioxolan-2-ylmethyl)-imidazoles
DD148219A5 (de)	1981-05-13	Verfahren zur herstellung von hydroxyethyl-azolen
EP0112284A2 (de)	1984-06-27	Neue Arylphenylether-derivate
DE2504114A1 (de)	1975-08-07	Imidazoliumsalze
DE2602770A1 (de)	1976-07-29	1,3-dioxolan-2-ylmethylimidazole, verfahren zu ihrer herstellung und ihre verwendung als biozide
DE2851086A1 (de)	1980-06-04	Hydroxypropyl-triazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE1670976A1 (de)	1971-06-16	N-Trityl-imidazole
CH648843A5 (de)	1985-04-15	1-(2-aryl-1,3-dioxolan-2-ylmethyl)-1h-1,2,4-triazole.
EP0180850A2 (de)	1986-05-14	Antimykotische Azolylmethyl-cyclopropyl-carbinol Derivate
DE3902031A1 (de)	1990-07-26	Substituierte azolylmethylcycloalkan-derivate, ihre herstellung und verwendung sowie diese enthaltende arzneimittel
EP0088874B1 (de)	1986-04-09	Azolyl-phenoxy-tetrahydrofuran-2-yliden-methane, Verfahren zu ihrer Herstellung sowie antimikrobielle Mittel, die diese Stoffe enthalten
DE2334352C3 (de)	1981-10-01	Im Heterocyclus halogenierte 1-(1,2,4-Triazol-1-yl)-1-phenoxy-3,3-dimethyl-butan-2-on- Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0040368B1 (de)	1983-09-28	Triazolyl-vinyl-ketone und -carbinole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EP0149814B1 (de)	1988-04-27	Azolylmethylcycloacetale, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0040366A1 (de)	1981-11-25	Imidazolyl-vinyl-ketone und -carbinole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EP0069754B1 (de)	1984-10-10	Verfahren zur herstellung von imidazolylvinylethern
EP0290907B1 (de)	1991-12-11	Verfahren zur Herstellung von Acetylenepoxiden und deren Verwendung
EP0073331B1 (de)	1986-04-09	5-Aryloxy-5-azolyl-3,3-dimethyl-1-penten-4-one und -ole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EP0096801B1 (de)	1987-09-09	Azolylmethyl-ketone, Verfahren zu ihrer Herstellung und ihre Verwendung als Zwischenprodukte