JPS6128674B2 - - Google Patents
Info
- Publication number
- JPS6128674B2 JPS6128674B2 JP76476A JP76476A JPS6128674B2 JP S6128674 B2 JPS6128674 B2 JP S6128674B2 JP 76476 A JP76476 A JP 76476A JP 76476 A JP76476 A JP 76476A JP S6128674 B2 JPS6128674 B2 JP S6128674B2
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- parts
- ylmethyl
- dioxolan
- dichlorophenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- -1 halotienyl Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 230000008018 melting Effects 0.000 description 42
- 238000002844 melting Methods 0.000 description 42
- 238000000034 method Methods 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 25
- 239000004480 active ingredient Substances 0.000 description 24
- 238000011282 treatment Methods 0.000 description 21
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 230000012010 growth Effects 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 241000222122 Candida albicans Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 description 10
- 239000012876 carrier material Substances 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 241000894006 Bacteria Species 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 9
- 230000000694 effects Effects 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 229910002651 NO3 Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000001105 regulatory effect Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- 240000008067 Cucumis sativus Species 0.000 description 7
- 229940095731 candida albicans Drugs 0.000 description 7
- 229960001701 chloroform Drugs 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 230000008635 plant growth Effects 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 230000001276 controlling effect Effects 0.000 description 6
- 239000002674 ointment Substances 0.000 description 6
- 241000700198 Cavia Species 0.000 description 5
- 206010061217 Infestation Diseases 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 201000003984 candidiasis Diseases 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 244000061176 Nicotiana tabacum Species 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 3
- NMAWVAOKKSGWHX-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 NMAWVAOKKSGWHX-UHFFFAOYSA-N 0.000 description 3
- LRZAKZPYSBPLLA-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-pentyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(CCCCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 LRZAKZPYSBPLLA-UHFFFAOYSA-N 0.000 description 3
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010007134 Candida infections Diseases 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 241000896242 Podosphaera Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 230000009545 invasion Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- OOSNUUSSUUDQNI-UHFFFAOYSA-N oxalic acid 1H-1,2,4-triazole Chemical compound C(C(=O)O)(=O)O.N1N=CN=C1 OOSNUUSSUUDQNI-UHFFFAOYSA-N 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- HTZGPEHWQCRXGZ-UHFFFAOYSA-N 1-(5-chlorothiophen-2-yl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)S1 HTZGPEHWQCRXGZ-UHFFFAOYSA-N 0.000 description 2
- PJEXBMOOBWGMBY-UHFFFAOYSA-N 2-bromo-1-(4-bromo-2-methylphenyl)ethanone Chemical compound CC1=CC(Br)=CC=C1C(=O)CBr PJEXBMOOBWGMBY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 208000032544 Cicatrix Diseases 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- 241000896218 Golovinomyces orontii Species 0.000 description 2
- 241000234435 Lilium Species 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 241000286209 Phasianidae Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000006159 Sabouraud's agar Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010042938 Systemic candida Diseases 0.000 description 2
- 229960000250 adipic acid Drugs 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 230000001332 colony forming effect Effects 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000004862 dioxolanes Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 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
- 238000005907 ketalization reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000002373 plant growth inhibitor Substances 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000012449 sabouraud dextrose agar Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- 230000037387 scars Effects 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 206010052366 systemic mycosis Diseases 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
- 230000001225 therapeutic effect Effects 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSESDZHLGIIHPS-UHFFFAOYSA-N 1-(4-amino-2-methoxyphenyl)ethanone Chemical compound COC1=CC(N)=CC=C1C(C)=O WSESDZHLGIIHPS-UHFFFAOYSA-N 0.000 description 1
- AKIAOKWHBCDYGR-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)ethanone Chemical compound COC1=CC(Cl)=CC=C1C(C)=O AKIAOKWHBCDYGR-UHFFFAOYSA-N 0.000 description 1
- TVNNKARIRPIZGM-UHFFFAOYSA-N 1-[(2-phenyl-1,3-dioxolan-2-yl)methyl]-1,2,4-triazole Chemical compound O1CCOC1(C=1C=CC=CC=1)CN1C=NC=N1 TVNNKARIRPIZGM-UHFFFAOYSA-N 0.000 description 1
- AQGZPSRLMVVDGN-UHFFFAOYSA-N 1-[[2-(2,3-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole oxalic acid Chemical compound C(C(=O)O)(=O)O.ClC1=C(C=CC=C1Cl)C1(OCCO1)CN1N=CN=C1 AQGZPSRLMVVDGN-UHFFFAOYSA-N 0.000 description 1
- XGUXTAKNQYKIIM-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole;nitric acid Chemical compound O[N+]([O-])=O.ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 XGUXTAKNQYKIIM-UHFFFAOYSA-N 0.000 description 1
- RPPNAOMKCXYWEE-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-hexyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole;nitric acid Chemical compound O[N+]([O-])=O.O1C(CCCCCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 RPPNAOMKCXYWEE-UHFFFAOYSA-N 0.000 description 1
- ZYVAOQMVHLIXFI-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole;nitric acid Chemical compound O[N+]([O-])=O.O1C(C)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 ZYVAOQMVHLIXFI-UHFFFAOYSA-N 0.000 description 1
- RTOLRPTWGBZHFP-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-octyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole;nitric acid Chemical compound O[N+]([O-])=O.O1C(CCCCCCCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 RTOLRPTWGBZHFP-UHFFFAOYSA-N 0.000 description 1
- DDIQRXJEBZSWON-UHFFFAOYSA-N 1-[[2-(2-chloro-4-methoxyphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole oxalic acid Chemical compound C(C(=O)O)(=O)O.ClC1=C(C=CC(=C1)OC)C1(OCCO1)CN1N=CN=C1 DDIQRXJEBZSWON-UHFFFAOYSA-N 0.000 description 1
- OTESLOVDNPLKHH-UHFFFAOYSA-N 1-[[2-(3-bromo-4-methylphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1=C(Br)C(C)=CC=C1C1(CN2N=CN=C2)OCCO1 OTESLOVDNPLKHH-UHFFFAOYSA-N 0.000 description 1
- XRZNSGVOZBKWIE-UHFFFAOYSA-N 1-[[2-(3-bromophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound BrC1=CC=CC(C2(CN3N=CN=C3)OCCO2)=C1 XRZNSGVOZBKWIE-UHFFFAOYSA-N 0.000 description 1
- UFVCZYXWRHHULC-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound ClC1=CC=CC(C2(CN3N=CN=C3)OCCO2)=C1 UFVCZYXWRHHULC-UHFFFAOYSA-N 0.000 description 1
- BNEQDWJZQUWSKR-UHFFFAOYSA-N 1-[[2-(3-methylphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound CC1=CC=CC(C2(CN3N=CN=C3)OCCO2)=C1 BNEQDWJZQUWSKR-UHFFFAOYSA-N 0.000 description 1
- GXSOEROGCZOXKZ-UHFFFAOYSA-N 1-[[2-(3-nitrophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1(OCCO1)CN1N=CN=C1 GXSOEROGCZOXKZ-UHFFFAOYSA-N 0.000 description 1
- HAGTYIJQUJCOKV-UHFFFAOYSA-N 1-[[2-(4-bromo-2-methylphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound CC1=CC(Br)=CC=C1C1(CN2N=CN=C2)OCCO1 HAGTYIJQUJCOKV-UHFFFAOYSA-N 0.000 description 1
- INXAXLYXGDBVCK-UHFFFAOYSA-N 1-[[2-(4-bromophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC(Br)=CC=C1C1(CN2N=CN=C2)OCCO1 INXAXLYXGDBVCK-UHFFFAOYSA-N 0.000 description 1
- KPQBEDVJCNRGRP-UHFFFAOYSA-N 1-[[2-(4-chloro-2-methylphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound ClC1=CC(=C(C=C1)C1(OCCO1)CN1N=CN=C1)C KPQBEDVJCNRGRP-UHFFFAOYSA-N 0.000 description 1
- XXSQUNBVMWXADL-UHFFFAOYSA-N 1-[[2-(4-iodophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole oxalic acid Chemical compound C(C(=O)O)(=O)O.IC1=CC=C(C=C1)C1(OCCO1)CN1N=CN=C1 XXSQUNBVMWXADL-UHFFFAOYSA-N 0.000 description 1
- PWUWDKSOLFJLJH-UHFFFAOYSA-N 1-[[2-(4-nitrophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(CN2N=CN=C2)OCCO1 PWUWDKSOLFJLJH-UHFFFAOYSA-N 0.000 description 1
- VAKPKJCPSHKYGY-UHFFFAOYSA-N 1-[[2-(5-chlorothiophen-2-yl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound S1C(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 VAKPKJCPSHKYGY-UHFFFAOYSA-N 0.000 description 1
- IJMUKNNEMKMARC-UHFFFAOYSA-N 1-[[2-(9h-fluoren-2-yl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1CCOC1(C=1C=C2C(C3=CC=CC=C3C2)=CC=1)CN1C=NC=N1 IJMUKNNEMKMARC-UHFFFAOYSA-N 0.000 description 1
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 description 1
- PTXMTZUUIOZOKF-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1,3-dioxolane Chemical compound ClC1=CC(Cl)=CC=C1C1OCCO1 PTXMTZUUIOZOKF-UHFFFAOYSA-N 0.000 description 1
- KXUZOBLKRVZJOK-UHFFFAOYSA-N 2-(bromomethyl)-2-(2,4-dibromophenyl)-1,3-dioxolane Chemical compound C=1C=C(Br)C=C(Br)C=1C1(CBr)OCCO1 KXUZOBLKRVZJOK-UHFFFAOYSA-N 0.000 description 1
- UZODYYMXCMVQFJ-UHFFFAOYSA-N 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxolane Chemical compound O1C(C)COC1(CBr)C1=CC=C(Cl)C=C1Cl UZODYYMXCMVQFJ-UHFFFAOYSA-N 0.000 description 1
- BDIGWTGOEGDCDT-UHFFFAOYSA-N 2-(bromomethyl)-2-(4-bromo-2-methylphenyl)-1,3-dioxolane Chemical compound CC1=CC(Br)=CC=C1C1(CBr)OCCO1 BDIGWTGOEGDCDT-UHFFFAOYSA-N 0.000 description 1
- ZIJLKJSYVNDWCR-UHFFFAOYSA-N 2-(bromomethyl)-2-(4-chloro-2-methoxyphenyl)-1,3-dioxolane Chemical compound BrCC1(OCCO1)C1=C(C=C(C=C1)Cl)OC ZIJLKJSYVNDWCR-UHFFFAOYSA-N 0.000 description 1
- ZUDKIXCPBPASBW-UHFFFAOYSA-N 2-(bromomethyl)-2-(5-chlorothiophen-2-yl)-1,3-dioxolane Chemical compound S1C(Cl)=CC=C1C1(CBr)OCCO1 ZUDKIXCPBPASBW-UHFFFAOYSA-N 0.000 description 1
- PTOYHZNVRQUIKP-UHFFFAOYSA-N 2-(bromomethyl)-2-(9h-fluoren-2-yl)-1,3-dioxolane Chemical compound C=1C=C(C2=CC=CC=C2C2)C2=CC=1C1(CBr)OCCO1 PTOYHZNVRQUIKP-UHFFFAOYSA-N 0.000 description 1
- ICBRDCHYCWKNBH-UHFFFAOYSA-N 2-(bromomethyl)-2-naphthalen-2-yl-1,3-dioxolane Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CBr)OCCO1 ICBRDCHYCWKNBH-UHFFFAOYSA-N 0.000 description 1
- NTRATOUBIPAKPQ-UHFFFAOYSA-N 2-(bromomethyl)-2-phenyl-1,3-dioxolane Chemical compound C=1C=CC=CC=1C1(CBr)OCCO1 NTRATOUBIPAKPQ-UHFFFAOYSA-N 0.000 description 1
- IDRUFHLMTBZQBT-IHWYPQMZSA-N 2-[(Z)-prop-1-enyl]propanedioic acid Chemical compound C\C=C/C(C(O)=O)C(O)=O IDRUFHLMTBZQBT-IHWYPQMZSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- LYINTWKRUWVLBA-UHFFFAOYSA-N 2-phenyl-1,3-dioxolane Chemical compound O1CCOC1C1=CC=CC=C1 LYINTWKRUWVLBA-UHFFFAOYSA-N 0.000 description 1
- KNGOKMSCODQKMQ-UHFFFAOYSA-N 3,4-dihydroxyhexanedioic acid Chemical compound OC(=O)CC(O)C(O)CC(O)=O KNGOKMSCODQKMQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- UPIQMVADUQYNGB-UHFFFAOYSA-N 4-[2-(bromomethyl)-1,3-dioxolan-2-yl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C1(CBr)OCCO1 UPIQMVADUQYNGB-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 1
- 240000006108 Allium ampeloprasum Species 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000223602 Alternaria alternata Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- JVFBIWKLPMTOMR-UHFFFAOYSA-N C(C(=O)O)(=O)O.COC1=C(C=CC=C1)C1(OCCO1)CN1N=CN=C1 Chemical compound C(C(=O)O)(=O)O.COC1=C(C=CC=C1)C1(OCCO1)CN1N=CN=C1 JVFBIWKLPMTOMR-UHFFFAOYSA-N 0.000 description 1
- SPXLCXAINOAJSA-UHFFFAOYSA-N C(C(=O)O)(=O)O.ClC1=CC(=C(C=C1)C1(OCCO1)CN1N=CN=C1)OC Chemical compound C(C(=O)O)(=O)O.ClC1=CC(=C(C=C1)C1(OCCO1)CN1N=CN=C1)OC SPXLCXAINOAJSA-UHFFFAOYSA-N 0.000 description 1
- DRKWHGRKQUABAI-UHFFFAOYSA-N C(C(=O)O)(=O)O.ClC=1C=C(C=C(C1)Cl)C1(OCCO1)CN1N=CN=C1 Chemical compound C(C(=O)O)(=O)O.ClC=1C=C(C=C(C1)Cl)C1(OCCO1)CN1N=CN=C1 DRKWHGRKQUABAI-UHFFFAOYSA-N 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 201000007336 Cryptococcosis Diseases 0.000 description 1
- 241000221204 Cryptococcus neoformans Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000896222 Erysiphe polygoni Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000893980 Microsporum canis Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- 241001507673 Penicillium digitatum Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000222831 Phialophora <Chaetothyriales> Species 0.000 description 1
- 241000896203 Podosphaera pannosa Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241001427555 Polyphaga <Blattaria> Species 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000561282 Thielaviopsis basicola Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N beta-hydroxyethanesulfonic acid Natural products OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000005200 bud stage Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 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
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 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
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000003630 growth substance Substances 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- ZFVNPQBTVHWDOK-UHFFFAOYSA-N nitric acid;1h-1,2,4-triazole Chemical compound O[N+]([O-])=O.C=1N=CNN=1 ZFVNPQBTVHWDOK-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000021590 normal diet Nutrition 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
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GILUHUDJUVHQJX-UHFFFAOYSA-N oxalic acid 1-[[2-(2,4,5-trichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C(C(=O)O)(=O)O.ClC1=C(C=C(C(=C1)Cl)Cl)C1(OCCO1)CN1N=CN=C1 GILUHUDJUVHQJX-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000011121 vaginal smear Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/620,989 US4079062A (en) | 1974-11-18 | 1975-10-09 | Triazole derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5246075A JPS5246075A (en) | 1977-04-12 |
JPS6128674B2 true JPS6128674B2 (da) | 1986-07-01 |
Family
ID=24488262
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP76476A Granted JPS5246075A (en) | 1975-10-09 | 1976-01-01 | 11*betaaaryl* ethyll1hh 1*2*44triazolketal and pharmaceutically acceptable acid adduct salt thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5246075A (da) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ196075A (en) * | 1980-02-04 | 1982-12-07 | Janssen Pharmaceutica Nv | Agent to protect wood coatings and detergents from micro-organisms using a triazole |
US4753954A (en) * | 1986-02-14 | 1988-06-28 | Ciba-Geigy Corporation | Fungicidal compositions and methods of combatting fungi employing a synergistic combination of propiconazol and fenpropidin |
JPS62212307A (ja) * | 1986-03-06 | 1987-09-18 | チバ−ガイギ− アクチエンゲゼルシヤフト | 殺菌剤組成物及びその使用方法 |
JP5958905B2 (ja) * | 2011-10-20 | 2016-08-02 | 公立大学法人秋田県立大学 | 植物成長調節剤 |
-
1976
- 1976-01-01 JP JP76476A patent/JPS5246075A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5246075A (en) | 1977-04-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4079062A (en) | Triazole derivatives | |
CA1094079A (en) | Triazole derivatives | |
US4160838A (en) | Antimicrobial and plant-growth-regulating triazole derivatives | |
US4156008A (en) | 1-(4-Alkyl-2-aryl-1,3-dioxolan-2-ylmethyl)-1H-imidazoles | |
US4849439A (en) | α-phenyl-α-cyclopropylalkyene-1H-imidazole- and 1,2,4 triazole-ethanols as antimycotic agents | |
CA1215989A (en) | Substituted 1-hydroxyethyl-triazolyl derivatives | |
EP0111711B1 (de) | Heterocyclisch substituierte Hydroxyalkyl-azolyl-Derivate | |
US4101664A (en) | 1-(2-Ar-4-aryloxymethyl-1,3-dioxolan-2-ylmethyl)-imidazoles | |
EP0237962A2 (de) | 2-Azolylmethyl-2-aryl-1,3-dioxolane und deren Salze, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung | |
HU184634B (en) | Fungicide compositions and process for producing 1-bracket-2-phenyl-4,5-disubstituted-1,3-dioxolan-2-yl-methyl-bracket closed-1h-imidazol- and 1h-1,2,4-triazol derivatives as active agents | |
GB1589852A (en) | 1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles | |
HU176919B (hu) | Fungicidnye preparaty soderzhahhie galogenozamehhjonnye proizvodnye 1-azolil-butana i sposob poluchenija aktivnykh vehhestv | |
HU179414B (en) | Process for producing hydroxy-propyl-triasole derivatives and pharmaceutical compositions containing them as active agents | |
SU1396966A3 (ru) | Способ получени производных азола или их фитофармацевтически приемлемых кислотно-аддитивных солей | |
CH648843A5 (de) | 1-(2-aryl-1,3-dioxolan-2-ylmethyl)-1h-1,2,4-triazole. | |
KR870001829B1 (ko) | 비스-트리아졸 유도체의 제조방법 | |
IE57056B1 (en) | Triazole antifungal agents | |
JPS6128674B2 (da) | ||
DE2846980A1 (de) | 1-ethen-azol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
EP0183494A2 (en) | Triazole antifungal agents | |
JPS6328916B2 (da) | ||
EP0133805B1 (en) | Triazole antifungal agents | |
DD200215A5 (de) | Fungizide mittel | |
JPH0121147B2 (da) | ||
JPS61122279A (ja) | トリアゾリルメチルカルビノール‐アリールアセタール類 |