JPH0434548B2 - - Google Patents
Info
- Publication number
- JPH0434548B2 JPH0434548B2 JP58173672A JP17367283A JPH0434548B2 JP H0434548 B2 JPH0434548 B2 JP H0434548B2 JP 58173672 A JP58173672 A JP 58173672A JP 17367283 A JP17367283 A JP 17367283A JP H0434548 B2 JPH0434548 B2 JP H0434548B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- triiodoallyl
- formula
- yield
- reaction
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims description 9
- 229940121375 antifungal agent Drugs 0.000 claims description 8
- 239000003429 antifungal agent Substances 0.000 claims description 7
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 238000000921 elemental analysis Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- 241000233866 Fungi Species 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 aralkyl ethers Chemical class 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003536 tetrazoles Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- SQRDRPSVGROPHX-UHFFFAOYSA-N 2,3,3-triiodoprop-2-en-1-ol Chemical compound OCC(I)=C(I)I SQRDRPSVGROPHX-UHFFFAOYSA-N 0.000 description 1
- LEDKKDPOPIKMSZ-UHFFFAOYSA-M 2,4,5-trichlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl LEDKKDPOPIKMSZ-UHFFFAOYSA-M 0.000 description 1
- OVOJUAKDTOOXRF-UHFFFAOYSA-M 2,4-dinitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C([N+]([O-])=O)=C1 OVOJUAKDTOOXRF-UHFFFAOYSA-M 0.000 description 1
- XXKZYJFUOPNRCL-UHFFFAOYSA-M 2-cyanobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1C#N XXKZYJFUOPNRCL-UHFFFAOYSA-M 0.000 description 1
- WIWQDBABYGRKEW-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 WIWQDBABYGRKEW-UHFFFAOYSA-N 0.000 description 1
- ITQJQEXFJIPBSO-UHFFFAOYSA-N 3-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=CC(S(O)(=O)=O)=C1 ITQJQEXFJIPBSO-UHFFFAOYSA-N 0.000 description 1
- FNMPWSYBWQWZSF-UHFFFAOYSA-N 4-carbamoylbenzenesulfonic acid Chemical compound NC(=O)C1=CC=C(S(O)(=O)=O)C=C1 FNMPWSYBWQWZSF-UHFFFAOYSA-N 0.000 description 1
- RPKWNMFDAOACCX-UHFFFAOYSA-M 4-chloro-3-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC(S([O-])(=O)=O)=CC=C1Cl RPKWNMFDAOACCX-UHFFFAOYSA-M 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 description 1
- IWYVYUZADLIDEY-UHFFFAOYSA-M 4-methoxybenzenesulfonate Chemical compound COC1=CC=C(S([O-])(=O)=O)C=C1 IWYVYUZADLIDEY-UHFFFAOYSA-M 0.000 description 1
- HHDRWGJJZGJSGZ-UHFFFAOYSA-N 5-benzyl-2h-tetrazole Chemical compound C=1C=CC=CC=1CC=1N=NNN=1 HHDRWGJJZGJSGZ-UHFFFAOYSA-N 0.000 description 1
- KYRMPMCAOPMOIR-UHFFFAOYSA-N 5-ethyl-2h-tetrazole Chemical compound CCC=1N=NNN=1 KYRMPMCAOPMOIR-UHFFFAOYSA-N 0.000 description 1
- YQMOOZYBLZGKRU-UHFFFAOYSA-N 5-heptyl-2h-tetrazole Chemical compound CCCCCCCC1=NN=NN1 YQMOOZYBLZGKRU-UHFFFAOYSA-N 0.000 description 1
- OKIYPFZZDQLNMP-UHFFFAOYSA-N 5-pentyl-2h-tetrazole Chemical compound CCCCCC=1N=NNN=1 OKIYPFZZDQLNMP-UHFFFAOYSA-N 0.000 description 1
- RFFXUEDBNNOGDO-UHFFFAOYSA-N 5-propan-2-yl-2h-tetrazole Chemical compound CC(C)C=1N=NNN=1 RFFXUEDBNNOGDO-UHFFFAOYSA-N 0.000 description 1
- JAHCQVVOKAFXQU-UHFFFAOYSA-N 5-propyl-2h-tetrazole Chemical compound CCCC=1N=NNN=1 JAHCQVVOKAFXQU-UHFFFAOYSA-N 0.000 description 1
- ZEKBKTMMBLWNGK-UHFFFAOYSA-N 5-tert-butyl-2h-tetrazole Chemical compound CC(C)(C)C=1N=NNN=1 ZEKBKTMMBLWNGK-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 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
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 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
- 239000003350 kerosene Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- UJJUJHTVDYXQON-UHFFFAOYSA-N nitro benzenesulfonate Chemical compound [O-][N+](=O)OS(=O)(=O)C1=CC=CC=C1 UJJUJHTVDYXQON-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17367283A JPS6064970A (ja) | 1983-09-19 | 1983-09-19 | トリヨ−ドアリルテトラゾ−ルおよびその製法並びにそれを有効成分とする抗菌，抗カビ剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17367283A JPS6064970A (ja) | 1983-09-19 | 1983-09-19 | トリヨ−ドアリルテトラゾ−ルおよびその製法並びにそれを有効成分とする抗菌，抗カビ剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6064970A JPS6064970A (ja) | 1985-04-13 |
| JPH0434548B2 true JPH0434548B2 (de) | 1992-06-08 |
Family
ID=15964956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17367283A Granted JPS6064970A (ja) | 1983-09-19 | 1983-09-19 | トリヨ−ドアリルテトラゾ−ルおよびその製法並びにそれを有効成分とする抗菌，抗カビ剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6064970A (de) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0080051A2 (de) * | 1981-10-07 | 1983-06-01 | Meiji Seika Kaisha Ltd. | Heterocyclische Verbindungen und fungizide und bakterizide Zusammensetzungen die sie enthalten |
-
1983
- 1983-09-19 JP JP17367283A patent/JPS6064970A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0080051A2 (de) * | 1981-10-07 | 1983-06-01 | Meiji Seika Kaisha Ltd. | Heterocyclische Verbindungen und fungizide und bakterizide Zusammensetzungen die sie enthalten |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6064970A (ja) | 1985-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5823671A (ja) | イミダゾリル−ｏ，ｎ−アセタ−ルおよびその塩の製法 | |
| JPS62201849A (ja) | ベンジルアミン誘導体、その製造法およびその用途 | |
| EP0245989B1 (de) | Fluorphthalimide | |
| KR880001998B1 (ko) | 테트라졸화합물의 제조방법 | |
| JPH0434548B2 (de) | ||
| DE3701142C2 (de) | ||
| EP0429281A2 (de) | Guanidin-Derivate und dieselben enthaltende Fungizide für Landwirtschaft und Gartenbau | |
| EP0205327B1 (de) | Phenoxyacetylamidderivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| FR2514757A1 (fr) | Phenoxyalkylamides, leur preparation, compositions herbicides en contenant et leur utilisation dans la destruction des mauvaises herbes | |
| JPS61291555A (ja) | Ｎ−置換グルタミン酸およびその用途 | |
| HU182546B (en) | Fungicide compositions containing 3-phenyl-pyrrol derivatives as active agents, and process for producing these compounds | |
| JPS58183672A (ja) | ヨ−ドプロパルギル化合物、その製造法及びそれを有効成分とする抗カビ剤 | |
| JPS6064969A (ja) | ヨ−ドプロパルギルテトラゾ−ルおよびその製法並びにそれを有効成分とする抗菌，抗カビ剤 | |
| JPS58219159A (ja) | スルホンアミド系化合物 | |
| JPS62181260A (ja) | ピリジン誘導体およびそれを有効成分とする農園芸用殺菌剤 | |
| US4136189A (en) | 2-(5-nitro-furfurylidene)-amino-benzimidoles and fungicidal compositions containing the same | |
| KR790001342B1 (ko) | 트리아졸릴-0, n-아세탈류의 제법 | |
| KR810000679B1 (ko) | 페닐피롤 유도체의 제조방법 | |
| JPS63238068A (ja) | ４−アニリノ−５−トリフルオロメチルピリミジン誘導体及びそれを有効成分とする農園芸用殺菌、殺ダニ剤 | |
| CH644846A5 (fr) | Esters et thioesters d'aminoacides, leur utilisation pour la lutte contre les parasites et leur preparation. | |
| JPS617259A (ja) | トリアゾリルアシルオキシエタン類及びこれを有効成分とする殺菌剤 | |
| JPS58105971A (ja) | イミダゾ−ル誘導体及びそれを有効成分とする抗菌，抗かび剤 | |
| JP2002205985A (ja) | ピラゾール−３−カルボキサミド誘導体およびこれを有効成分とする殺菌剤 | |
| JPH0368558A (ja) | ピラゾールアミド類およびこれを有効成分とする殺菌剤 | |
| JPH03106856A (ja) | ヒドロキシ酢酸アラルキルオキシアミド誘導体および農園芸用殺菌剤 |