NO784041L - Azolylalkyl-pyridinyl-etere, fremgangsmaate til deres fremstilling samt deres anvendelse som fungicider - Google Patents
Azolylalkyl-pyridinyl-etere, fremgangsmaate til deres fremstilling samt deres anvendelse som fungiciderInfo
- Publication number
- NO784041L NO784041L NO784041A NO784041A NO784041L NO 784041 L NO784041 L NO 784041L NO 784041 A NO784041 A NO 784041A NO 784041 A NO784041 A NO 784041A NO 784041 L NO784041 L NO 784041L
- Authority
- NO
- Norway
- Prior art keywords
- dimethyl
- butan
- oxy
- azol
- formula
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 28
- 238000002360 preparation method Methods 0.000 title description 10
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910052751 metal Chemical class 0.000 claims description 9
- 239000002184 metal Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- GKMQWTVAAMITHR-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O.CCC(C)O GKMQWTVAAMITHR-UHFFFAOYSA-N 0.000 description 48
- 239000013543 active substance Substances 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 33
- -1 halogen ether ketones Chemical class 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 240000005979 Hordeum vulgare Species 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 241000221785 Erysiphales Species 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- CLNNBQDAAGDAHI-UHFFFAOYSA-N 6-chloro-1h-pyridin-2-one Chemical compound OC1=CC=CC(Cl)=N1 CLNNBQDAAGDAHI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000005554 pickling Methods 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 244000141359 Malus pumila Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 241001480061 Blumeria graminis Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 208000024386 fungal infectious disease Diseases 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
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- 230000009885 systemic effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229910052727 yttrium Inorganic materials 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YYPWIRITDXMPSJ-UHFFFAOYSA-N 1-bromo-1-(6-chloropyridin-2-yl)oxy-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Br)OC1=CC=CC(Cl)=N1 YYPWIRITDXMPSJ-UHFFFAOYSA-N 0.000 description 2
- 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
- FMWWRALTYIWZEB-UHFFFAOYSA-N 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)CN1C=NC=N1 FMWWRALTYIWZEB-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- 241000221787 Erysiphe Species 0.000 description 2
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- 241000489964 Fusicladium Species 0.000 description 2
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- 206010037888 Rash pustular Diseases 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
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- UDWZXMQIEHAAQT-UHFFFAOYSA-N 1,1-dichloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Cl)Cl UDWZXMQIEHAAQT-UHFFFAOYSA-N 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- CNXKQVWAYJJREU-UHFFFAOYSA-N 1-(2,6-dibromopyridin-4-yl)oxy-3,3-dimethyl-1-pyrrol-1-ylbutan-2-one Chemical compound C1=CC=CN1C(C(=O)C(C)(C)C)OC1=CC(Br)=NC(Br)=C1 CNXKQVWAYJJREU-UHFFFAOYSA-N 0.000 description 1
- IFTIZBIVZOGDJC-UHFFFAOYSA-N 1-(2,6-dichloropyridin-4-yl)oxy-3,3-dimethyl-1-pyrrol-1-ylbutan-2-one Chemical compound C1=CC=CN1C(C(=O)C(C)(C)C)OC1=CC(Cl)=NC(Cl)=C1 IFTIZBIVZOGDJC-UHFFFAOYSA-N 0.000 description 1
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- JKFKUDRSQHGGAG-UHFFFAOYSA-N 1-(2-chloropyridin-4-yl)oxy-3,3-dimethyl-1-pyrrol-1-ylbutan-2-one Chemical compound C1=CC=CN1C(C(=O)C(C)(C)C)OC1=CC=NC(Cl)=C1 JKFKUDRSQHGGAG-UHFFFAOYSA-N 0.000 description 1
- PYSZDYPYWRDDCQ-UHFFFAOYSA-N 1-(2-fluoropyridin-4-yl)oxy-3,3-dimethyl-1-pyrrol-1-ylbutan-2-one Chemical compound C1=CC=CN1C(C(=O)C(C)(C)C)OC1=CC=NC(F)=C1 PYSZDYPYWRDDCQ-UHFFFAOYSA-N 0.000 description 1
- REASNOSAYVQZDH-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)oxy-3,3-dimethyl-1-pyrrol-1-ylbutan-2-one Chemical compound C1=CC=CN1C(C(=O)C(C)(C)C)OC1=CC(Cl)=CC=N1 REASNOSAYVQZDH-UHFFFAOYSA-N 0.000 description 1
- XJQJNTVFVMNTHP-UHFFFAOYSA-N 1-(5-bromopyridin-2-yl)oxy-3,3-dimethyl-1-pyrrol-1-ylbutan-2-one Chemical compound C1=CC=CN1C(C(=O)C(C)(C)C)OC1=CC=C(Br)C=N1 XJQJNTVFVMNTHP-UHFFFAOYSA-N 0.000 description 1
- QIIUJEUPXKCZMS-UHFFFAOYSA-N 1-(5-iodopyridin-3-yl)oxy-3,3-dimethyl-1-pyrrol-1-ylbutan-2-one Chemical compound C1=CC=CN1C(C(=O)C(C)(C)C)OC1=CN=CC(I)=C1 QIIUJEUPXKCZMS-UHFFFAOYSA-N 0.000 description 1
- JRQZWRXXLFCQIZ-UHFFFAOYSA-N 1-(6-chloropyridin-2-yl)oxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=CC(Cl)=N1 JRQZWRXXLFCQIZ-UHFFFAOYSA-N 0.000 description 1
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- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 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
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000002294 pubertal effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 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
- 239000000779 smoke Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772756269 DE2756269A1 (de) | 1977-12-16 | 1977-12-16 | Azolylalkyl-pyridinyl-aether, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO784041L true NO784041L (no) | 1979-06-19 |
Family
ID=6026376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO784041A NO784041L (no) | 1977-12-16 | 1978-12-01 | Azolylalkyl-pyridinyl-etere, fremgangsmaate til deres fremstilling samt deres anvendelse som fungicider |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4396624A (xx) |
| EP (1) | EP0002678B1 (xx) |
| JP (1) | JPS5488274A (xx) |
| AR (1) | AR219778A1 (xx) |
| AT (1) | AT361253B (xx) |
| AU (1) | AU518564B2 (xx) |
| BG (1) | BG28693A3 (xx) |
| BR (1) | BR7808203A (xx) |
| CA (1) | CA1134365A (xx) |
| CS (1) | CS208765B2 (xx) |
| DD (1) | DD141255A5 (xx) |
| DE (2) | DE2756269A1 (xx) |
| DK (1) | DK564778A (xx) |
| EG (1) | EG13541A (xx) |
| ES (1) | ES476041A1 (xx) |
| FI (1) | FI783842A (xx) |
| HU (1) | HU181853B (xx) |
| IL (1) | IL56200A (xx) |
| NO (1) | NO784041L (xx) |
| NZ (1) | NZ189160A (xx) |
| OA (1) | OA06127A (xx) |
| PH (1) | PH15108A (xx) |
| PL (1) | PL113536B1 (xx) |
| PT (1) | PT68901A (xx) |
| TR (1) | TR19888A (xx) |
| ZA (1) | ZA787043B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5722630Y2 (xx) * | 1979-06-29 | 1982-05-17 | ||
| DE2937595A1 (de) * | 1979-09-18 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1-azolyl-1-phenoxy-alkan-2-onen |
| DE3000244A1 (de) * | 1980-01-05 | 1981-07-09 | Bayer Ag, 5090 Leverkusen | Triazolylphenacyl-pyridyl-ether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE3028669A1 (de) * | 1980-07-29 | 1982-02-25 | Bayer Ag, 5090 Leverkusen | Substituierte triazolylalkyl-pyridylether, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| CA1175434A (en) * | 1980-09-10 | 1984-10-02 | Hoffmann-La Roche Limited | ¬(2-phenylamino-1-imidazolidinyloxy)methyl| pyridine 1-oxide derivatives |
| DE3443597A1 (de) * | 1984-11-29 | 1986-05-28 | Bayer Ag, 5090 Leverkusen | Substituierte azolylalkyl-pyridinyl-ether |
| CN113004247B (zh) * | 2019-12-19 | 2023-04-07 | 沈阳化工研究院有限公司 | 一种三唑衍生物及其应用 |
| CN114685211B (zh) * | 2020-12-11 | 2023-01-24 | 沈阳化工研究院有限公司 | 一种药肥组合物及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927011A (en) * | 1973-05-10 | 1975-12-16 | Yoshitomi Pharmaceutical | 2-Aminoalkyl-1-(pyridylcarbonylphenyl)imidazole compounds |
| DE2406665C3 (de) * | 1974-02-12 | 1978-11-16 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 1,2,4-Triazol-Derivaten |
| DE2423987C2 (de) * | 1974-05-17 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| DE2522176A1 (de) * | 1975-05-17 | 1976-11-25 | Hoechst Ag | 1-methyl-2-(pyridyl-oxymethyl)-nitro- imidazole und verfahren zu ihrer herstellung |
| GB1511390A (en) * | 1975-12-04 | 1978-05-17 | Pfizer Ltd | Imidazolylalkyl sulphide antifungal agents |
| US4166854A (en) * | 1978-11-02 | 1979-09-04 | The Dow Chemical Company | Substituted 1-pyridinyloxy-1-(imidazolyl)-2-butanone compounds and their use as fungicides |
-
1977
- 1977-12-16 DE DE19772756269 patent/DE2756269A1/de not_active Withdrawn
-
1978
- 1978-11-29 US US05/964,768 patent/US4396624A/en not_active Expired - Lifetime
- 1978-12-01 NO NO784041A patent/NO784041L/no unknown
- 1978-12-04 DE DE7878101534T patent/DE2861491D1/de not_active Expired
- 1978-12-04 EP EP78101534A patent/EP0002678B1/de not_active Expired
- 1978-12-11 BG BG041682A patent/BG28693A3/xx unknown
- 1978-12-12 OA OA56680A patent/OA06127A/xx unknown
- 1978-12-12 PT PT68901A patent/PT68901A/pt unknown
- 1978-12-13 CS CS788295A patent/CS208765B2/cs unknown
- 1978-12-13 IL IL56200A patent/IL56200A/xx unknown
- 1978-12-13 TR TR19888A patent/TR19888A/xx unknown
- 1978-12-13 NZ NZ189160A patent/NZ189160A/xx unknown
- 1978-12-13 EG EG701/78A patent/EG13541A/xx active
- 1978-12-14 CA CA000317967A patent/CA1134365A/en not_active Expired
- 1978-12-14 AT AT890878A patent/AT361253B/de not_active IP Right Cessation
- 1978-12-14 JP JP15382178A patent/JPS5488274A/ja active Pending
- 1978-12-14 BR BR7808203A patent/BR7808203A/pt unknown
- 1978-12-14 PH PH21948A patent/PH15108A/en unknown
- 1978-12-14 FI FI783842A patent/FI783842A/fi unknown
- 1978-12-15 AU AU42600/78A patent/AU518564B2/en not_active Expired
- 1978-12-15 PL PL1978211792A patent/PL113536B1/pl unknown
- 1978-12-15 DK DK564778A patent/DK564778A/da not_active Application Discontinuation
- 1978-12-15 DD DD78209815A patent/DD141255A5/de unknown
- 1978-12-15 ZA ZA00787043A patent/ZA787043B/xx unknown
- 1978-12-15 ES ES476041A patent/ES476041A1/es not_active Expired
- 1978-12-15 HU HU78BA3739A patent/HU181853B/hu unknown
- 1978-12-15 AR AR274823A patent/AR219778A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| IL56200A0 (en) | 1979-03-12 |
| AU518564B2 (en) | 1981-10-08 |
| US4396624A (en) | 1983-08-02 |
| FI783842A (fi) | 1979-06-17 |
| ES476041A1 (es) | 1979-04-16 |
| DE2756269A1 (de) | 1979-06-21 |
| CS208765B2 (en) | 1981-09-15 |
| OA06127A (fr) | 1981-06-30 |
| PT68901A (de) | 1979-01-01 |
| BG28693A3 (en) | 1980-06-16 |
| IL56200A (en) | 1982-07-30 |
| DD141255A5 (de) | 1980-04-23 |
| AR219778A1 (es) | 1980-09-15 |
| CA1134365A (en) | 1982-10-26 |
| EP0002678B1 (de) | 1981-12-30 |
| AU4260078A (en) | 1979-06-21 |
| EP0002678A3 (en) | 1979-07-25 |
| EG13541A (en) | 1981-12-31 |
| PL113536B1 (en) | 1980-12-31 |
| PH15108A (en) | 1982-08-10 |
| DK564778A (da) | 1979-06-17 |
| ZA787043B (en) | 1979-11-28 |
| PL211792A1 (pl) | 1979-11-19 |
| HU181853B (en) | 1983-11-28 |
| AT361253B (de) | 1981-02-25 |
| ATA890878A (de) | 1980-07-15 |
| EP0002678A2 (de) | 1979-07-11 |
| TR19888A (tr) | 1980-04-09 |
| BR7808203A (pt) | 1979-08-07 |
| NZ189160A (en) | 1981-01-23 |
| DE2861491D1 (en) | 1982-02-18 |
| JPS5488274A (en) | 1979-07-13 |
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