JPS6055518B2 - Ｎ‐トリチル‐アゾールの金属錯体、その製法および殺菌剤としての使用 - Google Patents
Ｎ‐トリチル‐アゾールの金属錯体、その製法および殺菌剤としての使用Info
- Publication number
- JPS6055518B2 JPS6055518B2 JP51005999A JP599976A JPS6055518B2 JP S6055518 B2 JPS6055518 B2 JP S6055518B2 JP 51005999 A JP51005999 A JP 51005999A JP 599976 A JP599976 A JP 599976A JP S6055518 B2 JPS6055518 B2 JP S6055518B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- formulas
- trityl
- azole
- manufacturing
- 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
- 239000002184 metal Substances 0.000 title claims description 10
- 229910052751 metal Inorganic materials 0.000 title claims description 10
- WDVPOTIYAXHVEQ-UHFFFAOYSA-N 1-tritylpyrrole Chemical compound C1=CC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WDVPOTIYAXHVEQ-UHFFFAOYSA-N 0.000 title claims description 7
- 239000000417 fungicide Substances 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 239000000645 desinfectant Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 241000233866 Fungi Species 0.000 description 11
- 239000003085 diluting agent Substances 0.000 description 11
- 208000015181 infectious disease Diseases 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- -1 trityl halide Chemical class 0.000 description 7
- 241000221785 Erysiphales Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- NPZDCTUDQYGYQD-UHFFFAOYSA-N 1-tritylimidazole Chemical compound C1=NC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NPZDCTUDQYGYQD-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- HAGYXNVNFOULKK-UHFFFAOYSA-N 1-trityl-1,2,4-triazole Chemical compound N1=CN=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HAGYXNVNFOULKK-UHFFFAOYSA-N 0.000 description 2
- 241000221198 Basidiomycota Species 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PSBVYDIEBNSUQB-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)-diphenylmethyl]-1,2,4-triazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C(N1N=CN=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 PSBVYDIEBNSUQB-UHFFFAOYSA-N 0.000 description 1
- QGCQRZWXVPJNLV-UHFFFAOYSA-N 1-[(3-chlorophenyl)-diphenylmethyl]imidazole Chemical compound ClC1=CC=CC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)N2C=NC=C2)=C1 QGCQRZWXVPJNLV-UHFFFAOYSA-N 0.000 description 1
- NPZDCTUDQYGYQD-UHFFFAOYSA-O 1-trityl-1h-imidazol-1-ium Chemical class C1=NC=C[NH+]1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NPZDCTUDQYGYQD-UHFFFAOYSA-O 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000195955 Equisetum hyemale Species 0.000 description 1
- 241000925440 Erysiphe sp. Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 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
- 241001465754 Metazoa Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000896242 Podosphaera Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241001203501 Venturia sp. (in: Fungi) Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- FAFUJZWQZMBFEA-UHFFFAOYSA-K [Na+].[Na+].[Ca+2].[O-][N+]([O-])=O.[O-]P([O-])([O-])=O Chemical compound [Na+].[Na+].[Ca+2].[O-][N+]([O-])=O.[O-]P([O-])([O-])=O FAFUJZWQZMBFEA-UHFFFAOYSA-K 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940079721 copper chloride Drugs 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide 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
- 229920005610 lignin Polymers 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2502932A DE2502932C2 (de) | 1975-01-24 | 1975-01-24 | Metallkomplexe von N-Trityl-azolen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| DE2502932.7 | 1975-01-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5198273A JPS5198273A (en) | 1976-08-30 |
| JPS6055518B2 true JPS6055518B2 (ja) | 1985-12-05 |
Family
ID=5937242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51005999A Expired JPS6055518B2 (ja) | 1975-01-24 | 1976-01-23 | Ｎ‐トリチル‐アゾールの金属錯体、その製法および殺菌剤としての使用 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4073901A (en, 2012) |
| JP (1) | JPS6055518B2 (en, 2012) |
| AT (1) | AT345616B (en, 2012) |
| BE (1) | BE837854A (en, 2012) |
| BR (1) | BR7600384A (en, 2012) |
| CH (1) | CH616664A5 (en, 2012) |
| CS (1) | CS186728B2 (en, 2012) |
| DD (1) | DD125645A5 (en, 2012) |
| DE (1) | DE2502932C2 (en, 2012) |
| DK (1) | DK140460C (en, 2012) |
| EG (1) | EG12115A (en, 2012) |
| ES (1) | ES444564A1 (en, 2012) |
| FR (1) | FR2298542A1 (en, 2012) |
| GB (1) | GB1463429A (en, 2012) |
| IE (1) | IE42407B1 (en, 2012) |
| IL (1) | IL48883A (en, 2012) |
| IT (1) | IT1054464B (en, 2012) |
| LU (1) | LU74228A1 (en, 2012) |
| NL (1) | NL7600612A (en, 2012) |
| PL (1) | PL96760B1 (en, 2012) |
| PT (1) | PT64712B (en, 2012) |
| SU (1) | SU577934A3 (en, 2012) |
| TR (1) | TR18811A (en, 2012) |
| ZA (1) | ZA76384B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4143137A (en) * | 1976-01-07 | 1979-03-06 | Rohm And Haas Company | Substituted arylcyanoalkyl and diarylcyanoalkylimidazole metal salt complexes and fungicidal compositions and methods utilizing them |
| DE2725214A1 (de) * | 1977-06-03 | 1978-12-14 | Bayer Ag | Metallsalzkomplexe von 1-phenyl-2- triazolyl-aethyl-derivaten, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2847441A1 (de) * | 1978-11-02 | 1980-05-22 | Basf Ag | Imidazol-kupferkomplexverbindungen |
| HU195513B (en) * | 1984-10-16 | 1988-05-30 | Richter Gedeon Vegyeszet | Process for producing stable solutions of alkaloides with bis-indole skeleton |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321366A (en) * | 1965-11-15 | 1967-05-23 | Dow Chemical Co | Fungicidal methods and compositions |
| DE1670976B2 (de) * | 1968-01-29 | 1976-07-22 | N-trityl-imidazole | |
| CH488713A (de) * | 1968-08-28 | 1970-04-15 | Bayer Ag | Verfahren zur Herstellung von 1-Trityl-1,2,4-triazolen |
| US3647810A (en) * | 1969-07-03 | 1972-03-07 | Rohm & Haas | 1 2 4-triazole metal salt complexes |
| DE2423987C2 (de) * | 1974-05-17 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
-
1975
- 1975-01-24 DE DE2502932A patent/DE2502932C2/de not_active Expired
- 1975-10-23 GB GB4359575A patent/GB1463429A/en not_active Expired
-
1976
- 1976-01-14 US US05/649,161 patent/US4073901A/en not_active Expired - Lifetime
- 1976-01-16 CS CS7600000303A patent/CS186728B2/cs unknown
- 1976-01-19 PT PT64712A patent/PT64712B/pt unknown
- 1976-01-19 SU SU7602314955A patent/SU577934A3/ru active
- 1976-01-19 CH CH59776A patent/CH616664A5/de not_active IP Right Cessation
- 1976-01-19 EG EG24/76A patent/EG12115A/xx active
- 1976-01-21 IL IL48883A patent/IL48883A/xx unknown
- 1976-01-21 NL NL7600612A patent/NL7600612A/xx not_active Application Discontinuation
- 1976-01-22 IT IT19488/76A patent/IT1054464B/it active
- 1976-01-22 DK DK25476A patent/DK140460C/da not_active IP Right Cessation
- 1976-01-22 DD DD190919A patent/DD125645A5/xx unknown
- 1976-01-22 LU LU74228A patent/LU74228A1/xx unknown
- 1976-01-22 PL PL1976186706A patent/PL96760B1/pl unknown
- 1976-01-22 BR BR7600384A patent/BR7600384A/pt unknown
- 1976-01-23 ZA ZA384A patent/ZA76384B/xx unknown
- 1976-01-23 JP JP51005999A patent/JPS6055518B2/ja not_active Expired
- 1976-01-23 BE BE163754A patent/BE837854A/xx not_active IP Right Cessation
- 1976-01-23 TR TR18811A patent/TR18811A/xx unknown
- 1976-01-23 IE IE132/76A patent/IE42407B1/en unknown
- 1976-01-23 AT AT45976A patent/AT345616B/de not_active IP Right Cessation
- 1976-01-23 ES ES444564A patent/ES444564A1/es not_active Expired
- 1976-01-23 FR FR7601851A patent/FR2298542A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1463429A (en) | 1977-02-02 |
| DE2502932A1 (de) | 1976-07-29 |
| AU8791075A (en) | 1977-07-07 |
| IL48883A0 (en) | 1976-03-31 |
| EG12115A (en) | 1978-09-30 |
| TR18811A (tr) | 1977-11-01 |
| US4073901A (en) | 1978-02-14 |
| IT1054464B (it) | 1981-11-10 |
| DK140460C (da) | 1980-02-04 |
| CH616664A5 (en, 2012) | 1980-04-15 |
| FR2298542B1 (en, 2012) | 1980-06-13 |
| DE2502932C2 (de) | 1985-04-18 |
| AT345616B (de) | 1978-09-25 |
| DD125645A5 (en, 2012) | 1977-05-11 |
| BE837854A (fr) | 1976-07-23 |
| ES444564A1 (es) | 1977-06-16 |
| IL48883A (en) | 1978-09-29 |
| BR7600384A (pt) | 1976-08-31 |
| FR2298542A1 (fr) | 1976-08-20 |
| JPS5198273A (en) | 1976-08-30 |
| SU577934A3 (ru) | 1977-10-25 |
| PT64712B (fr) | 1977-08-11 |
| IE42407B1 (en) | 1980-07-30 |
| DK25476A (da) | 1976-07-25 |
| ZA76384B (en) | 1977-01-26 |
| DK140460B (da) | 1979-09-03 |
| IE42407L (en) | 1976-07-24 |
| NL7600612A (nl) | 1976-07-27 |
| LU74228A1 (en, 2012) | 1976-12-31 |
| ATA45976A (de) | 1978-01-15 |
| CS186728B2 (en) | 1978-12-29 |
| PL96760B1 (pl) | 1978-01-31 |
| PT64712A (fr) | 1976-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5953266B2 (ja) | トリアゾリル−アルカノンおよびこれらの塩の製造方法 | |
| IL44793A (en) | 1-phenoxy-1-(1,2,4-triazolyl)-alkanols their preparation and fungicidal compositions containing them | |
| JPS6128668B2 (en, 2012) | ||
| US4239760A (en) | Combating fungi and bacteria with 3-azolyl-benzo-1,2,4-triazines and 1-oxides thereof | |
| HU176919B (hu) | Fungicidnye preparaty soderzhahhie galogenozamehhjonnye proizvodnye 1-azolil-butana i sposob poluchenija aktivnykh vehhestv | |
| JPS5932463B2 (ja) | 新規なイミダゾリル誘導体およびその塩の製法 | |
| JPH0133467B2 (en, 2012) | ||
| CA1247110A (en) | .alpha.-ARYL-1H-AZOLE-1-ETHANOLS | |
| US4316932A (en) | Combating fungi with α-azolyl-keto derivatives | |
| JPS6052148B2 (ja) | α−アゾリル−β−ヒドロキシ−ケトン、その製造方法および殺菌剤組成物 | |
| HU177167B (en) | Fungicide compositions and process for preparing 4-azolyl-4-phenoxy-butanoic acid derivatives as active substances thereof | |
| JPS5941988B2 (ja) | １−プロピル−１，２，４−トリアゾリル誘導体およびそれらの塩の製造法 | |
| IL44821A (en) | Plant fungicidal and mircobicidal compositions containing certaining certain omega-imidazolyl-omega-phenoxy(or phenylthio)-alkanones | |
| JPS6337764B2 (en, 2012) | ||
| CS195322B2 (en) | Fungicide and method of preparing active substances therefor | |
| HU193271B (en) | Fungicide compositions containing azolyl-alkyl-terc-butyl-carbinol derivatives as active agents and process for producing azolyl-alkyl-terc-butyl-keton and -carbinol derivatives | |
| JPS6337788B2 (en, 2012) | ||
| JPS5835190B2 (ja) | シンキ １− エチル − トリアゾ−ルノ セイホウ | |
| JPS6026111B2 (ja) | 新規な１−アゾリル−４−ヒドロキシ−ブタン誘導体，その製造方法およびそれを活性成分として含有する殺菌剤組成物 | |
| HU176746B (en) | Fungicide compositions comtaining 1-bracket-2-halogeno-2-phenyl-ethyl-bracket closed-triasole derivatives as active agents and process for producing the active agents | |
| HU184047B (en) | Fungicide compositions containing 1-ethen-azol derivatives as active agents, and process for producing the active agents | |
| JPS6055518B2 (ja) | Ｎ‐トリチル‐アゾールの金属錯体、その製法および殺菌剤としての使用 | |
| SK30493A3 (en) | Triazole and imidazole derivatives, process for their preparation and their fungicidal composition | |
| JPS599553B2 (ja) | 新規ハロゲントリアゾ−ル誘導体の製法 | |
| HU181853B (en) | Fungicide compositions containing azolyl-alkyl-pyridinyl-ether derivatives and process for preparing azolyl-alkyl-pyridinyl-ether derivatives |