DE3132335A1 - Substituierte azolyl-phenoxy-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide - Google Patents
Substituierte azolyl-phenoxy-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizideInfo
- Publication number
- DE3132335A1 DE3132335A1 DE19813132335 DE3132335A DE3132335A1 DE 3132335 A1 DE3132335 A1 DE 3132335A1 DE 19813132335 DE19813132335 DE 19813132335 DE 3132335 A DE3132335 A DE 3132335A DE 3132335 A1 DE3132335 A1 DE 3132335A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- stands
- alkyl
- butyl
- substituted
- 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.)
- Withdrawn
Links
- -1 AZOLYL-PHENOXY Chemical class 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 35
- 239000000417 fungicide Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000460 chlorine Substances 0.000 claims description 25
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052751 metal Chemical class 0.000 claims description 10
- 239000002184 metal Chemical class 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229910052783 alkali metal 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 241000233866 Fungi Species 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 241000209219 Hordeum Species 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000005554 pickling Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011435 rock Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XBMQBGQLUVPOPF-UHFFFAOYSA-N 1-imidazol-1-yl-1-(4-methoxyimino-2-methylcyclohexa-1,5-dien-1-yl)oxy-3,3-dimethylbutan-2-one Chemical compound CC(C(C(OC1=C(CC(C=C1)=NOC)C)N1C=NC=C1)=O)(C)C XBMQBGQLUVPOPF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 241000228454 Pyrenophora graminea Species 0.000 description 3
- 241000520648 Pyrenophora teres Species 0.000 description 3
- 206010039509 Scab Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000221577 Uromyces appendiculatus Species 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
- 239000000969 carrier Substances 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
- 239000000839 emulsion Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HDPBJRFWHXHXNF-UHFFFAOYSA-N 3-(methoxyiminomethyl)phenol Chemical compound CON=CC1=CC=CC(O)=C1 HDPBJRFWHXHXNF-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
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKEKURXRUXRNES-UHFFFAOYSA-N bis(1h-pyrrol-2-yl)methanone Chemical class C=1C=CNC=1C(=O)C1=CC=CN1 DKEKURXRUXRNES-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000013339 cereals Nutrition 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
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000000463 material Substances 0.000 description 2
- 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 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RBEPFJJTENPUKJ-UHFFFAOYSA-N 1-[4-(methoxyiminomethyl)phenoxy]-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=CC(C=NOC)=CC=C1OC(C(=O)C(C)(C)C)N1N=CN=C1 RBEPFJJTENPUKJ-UHFFFAOYSA-N 0.000 description 1
- LTSVKZVKZDLEEK-UHFFFAOYSA-N 1-bromo-1-fluoro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(F)Br LTSVKZVKZDLEEK-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- DBFWHMRLUANEKP-UHFFFAOYSA-N 1-fluoro-1-(4-methoxyimino-2-methylcyclohexa-1,5-dien-1-yl)oxy-3,3-dimethylbutan-2-one Chemical compound CC(C(C(OC1=C(CC(C=C1)=NOC)C)F)=O)(C)C DBFWHMRLUANEKP-UHFFFAOYSA-N 0.000 description 1
- KOCUOUFHAVVFMC-UHFFFAOYSA-N 1-phenoxy-1-(1,2,4-triazol-1-yl)butan-2-one Chemical class C1=NC=NN1C(C(=O)CC)OC1=CC=CC=C1 KOCUOUFHAVVFMC-UHFFFAOYSA-N 0.000 description 1
- YCGAFVMCJLAIGM-UHFFFAOYSA-N 2-(methoxyiminomethyl)phenol Chemical compound CON=CC1=CC=CC=C1O YCGAFVMCJLAIGM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 244000215068 Acacia senegal Species 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000760356 Chytridiomycetes Species 0.000 description 1
- 241000228437 Cochliobolus Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D233/60—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 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813132335 DE3132335A1 (de) | 1981-08-17 | 1981-08-17 | Substituierte azolyl-phenoxy-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| AU86077/82A AU549479B2 (en) | 1981-08-17 | 1982-07-16 | Azolyl-phenoxy derivatives |
| US06/403,988 US4472416A (en) | 1981-08-17 | 1982-08-02 | Combating fungi with substituted azolyl-phenoxy derivatives |
| DE8282107071T DE3271363D1 (en) | 1981-08-17 | 1982-08-05 | Substituted phenoxy azolyl derivatives, process for their synthesis and their use as fungicides |
| EP82107071A EP0076370B1 (de) | 1981-08-17 | 1982-08-05 | Substituierte Azolyl-phenoxy-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| AT82107071T ATE20058T1 (de) | 1981-08-17 | 1982-08-05 | Substituierte azolyl-phenoxy-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide. |
| PT75398A PT75398B (en) | 1981-08-17 | 1982-08-09 | Process for the preparation of a fungicidal composition containing substituted azolyl-phenoxy derivatives |
| IL66542A IL66542A0 (en) | 1981-08-17 | 1982-08-13 | Substituted azolyl-phenoxy derivatives,their preparation and their use as fungicides |
| NZ201578A NZ201578A (en) | 1981-08-17 | 1982-08-13 | Imidazole and 1,2,4-triazole derivatives;fungicides |
| DD82242510A DD206528A5 (de) | 1981-08-17 | 1982-08-13 | Fungizide mittel |
| DK364682A DK168818B1 (da) | 1981-08-17 | 1982-08-13 | Substituerede azolylphenoxyderivater samt syreadditionssalte og metalsaltkomplekser deraf, deres fremstilling og anvendelse som fungicider |
| JP57139986A JPS5839670A (ja) | 1981-08-17 | 1982-08-13 | 置換されたアゾリル−フエノキシ誘導体、その製造法及び殺菌剤としての使用 |
| AR290311A AR231833A1 (es) | 1981-08-17 | 1982-08-13 | Derivados sustituidos de 1-azolil-1-(alcoxiiminometilfenoxi)-alcan-2-onas y 1-azolil-1-(alcoxiiminometilfenoxi)-alcan-2-oles,procedimientos para su obtencion y composiciones fitofungicidas que los contienen |
| GR69039A GR76255B (en, 2012) | 1981-08-17 | 1982-08-13 | |
| TR21372A TR21372A (tr) | 1981-08-17 | 1982-08-16 | S*bstit*e edilmis azolil-fenoksi t*revleri,bunlarin hazirlanmasi icin usuller ve bunlarin fungisitler olarak kullanilmalari |
| BR8204776A BR8204776A (pt) | 1981-08-17 | 1982-08-16 | Processo para a preparacao de derivados de azolil-fenoxi substituidos composicoes fungicidas processos para o combate de fungos e para a preparacao de composicoes |
| IE1978/82A IE53871B1 (en) | 1981-08-17 | 1982-08-16 | Substituted azolyl-phenoxy derivatives, processes for their preparation, and their use as fungicides |
| ES515031A ES515031A0 (es) | 1981-08-17 | 1982-08-16 | Procedimiento para la obtencion de derivados de azolil-fenoxisustituidos. |
| ZA825912A ZA825912B (en) | 1981-08-17 | 1982-08-16 | Substituted azolyl-pheonxy derivatives, process for their preparation, and their use as fungicides |
| PL1982237928A PL133290B1 (en) | 1981-08-17 | 1982-08-16 | Fungicide and method of manufacture of novel substituted azolyl-phenoxyl derivatives |
| CA000409518A CA1185981A (en) | 1981-08-17 | 1982-08-16 | Substituted azolyl-phenoxy derivatives, processes for their preparation, and their use as fungicides |
| EG82499A EG15752A (en) | 1981-08-17 | 1982-08-16 | Substituted azolyl-phenoxy derivatives,process for their preparation,and their use as fungicides |
| KR8203681A KR890001547B1 (ko) | 1981-08-17 | 1982-08-17 | 치환된 아졸린-페녹시 유도체의 제조방법 |
| HU822636A HU190409B (en) | 1981-08-17 | 1982-08-17 | Fungicide compositions containing azolyl-phenoxy derivatives as active agents and process for producing the active agents |
| CS826052A CS228938B2 (en) | 1981-08-17 | 1982-08-17 | Fungicide and method of preparing active component thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813132335 DE3132335A1 (de) | 1981-08-17 | 1981-08-17 | Substituierte azolyl-phenoxy-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3132335A1 true DE3132335A1 (de) | 1983-03-03 |
Family
ID=6139410
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813132335 Withdrawn DE3132335A1 (de) | 1981-08-17 | 1981-08-17 | Substituierte azolyl-phenoxy-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE8282107071T Expired DE3271363D1 (en) | 1981-08-17 | 1982-08-05 | Substituted phenoxy azolyl derivatives, process for their synthesis and their use as fungicides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282107071T Expired DE3271363D1 (en) | 1981-08-17 | 1982-08-05 | Substituted phenoxy azolyl derivatives, process for their synthesis and their use as fungicides |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4472416A (en, 2012) |
| EP (1) | EP0076370B1 (en, 2012) |
| JP (1) | JPS5839670A (en, 2012) |
| KR (1) | KR890001547B1 (en, 2012) |
| AR (1) | AR231833A1 (en, 2012) |
| AT (1) | ATE20058T1 (en, 2012) |
| AU (1) | AU549479B2 (en, 2012) |
| BR (1) | BR8204776A (en, 2012) |
| CA (1) | CA1185981A (en, 2012) |
| CS (1) | CS228938B2 (en, 2012) |
| DD (1) | DD206528A5 (en, 2012) |
| DE (2) | DE3132335A1 (en, 2012) |
| DK (1) | DK168818B1 (en, 2012) |
| EG (1) | EG15752A (en, 2012) |
| ES (1) | ES515031A0 (en, 2012) |
| GR (1) | GR76255B (en, 2012) |
| HU (1) | HU190409B (en, 2012) |
| IE (1) | IE53871B1 (en, 2012) |
| IL (1) | IL66542A0 (en, 2012) |
| NZ (1) | NZ201578A (en, 2012) |
| PL (1) | PL133290B1 (en, 2012) |
| PT (1) | PT75398B (en, 2012) |
| TR (1) | TR21372A (en, 2012) |
| ZA (1) | ZA825912B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3237400A1 (de) * | 1982-10-08 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Substituierte 1-hydroxyethyl-triazolyl-derivate |
| US4690942A (en) * | 1983-12-20 | 1987-09-01 | Ciba-Geigy Corporation | 1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters, and ethers, composition containing them, and use of them to control phytopathogenic microorganisms |
| DE3427844A1 (de) * | 1984-07-27 | 1986-02-06 | Bayer Ag, 5090 Leverkusen | Substituierte hydroxyalkyl-azole, verfahren zu ihrer herstellung sowie diese enthaltende antimykotische mittel |
| DE3545034A1 (de) * | 1985-12-19 | 1987-06-25 | Bayer Ag | Diastereomeres (a) des 3,3-dimethyl-1-(4-methoximinomethyl-phenoxy)-1-(1,2,4-triazol-1-yl)-butan-2-ols |
| DE3618379A1 (de) * | 1986-05-31 | 1987-12-03 | Bayer Ag | Verfahren zur herstellung eines azol-derivates |
| DE3620166A1 (de) * | 1986-06-14 | 1987-12-17 | Bayer Ag | Verfahren zur herstellung von hydroxybenzaldoxim-o-ethern |
| DE3701715A1 (de) * | 1987-01-22 | 1988-08-04 | Bayer Ag | Fungizide wirkstoffkombinationen |
| AUPQ105499A0 (en) * | 1999-06-18 | 1999-07-08 | Biota Scientific Management Pty Ltd | Antiviral agents |
| AUPR213700A0 (en) * | 2000-12-18 | 2001-01-25 | Biota Scientific Management Pty Ltd | Antiviral agents |
| US20030165413A1 (en) * | 2001-07-18 | 2003-09-04 | Benjamin Scharifker | Process to recover vanadium contained in acid solutions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1571C (de) * | 1877-12-14 | OHM, Apotheker in Chemnitz und Dr. LANG in j Leer | Einric htungen anDampf-Zerstäubungs-Apparaten | |
| US4147791A (en) * | 1972-01-11 | 1979-04-03 | Bayer Aktiengesellschaft | 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants |
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| DE2325156A1 (de) * | 1973-05-18 | 1974-12-05 | Bayer Ag | Fungizide und mikrobizide mittel |
| DE2333354C2 (de) * | 1973-06-30 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | 2-Aryloxy-2-(imidazol-1-yl)-äthanole sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| DE2600799A1 (de) * | 1976-01-10 | 1977-07-14 | Bayer Ag | Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2745827A1 (de) * | 1977-10-12 | 1979-04-26 | Basf Ag | Phenylazophenyloxy-triazolylverbindungen |
-
1981
- 1981-08-17 DE DE19813132335 patent/DE3132335A1/de not_active Withdrawn
-
1982
- 1982-07-16 AU AU86077/82A patent/AU549479B2/en not_active Ceased
- 1982-08-02 US US06/403,988 patent/US4472416A/en not_active Expired - Fee Related
- 1982-08-05 EP EP82107071A patent/EP0076370B1/de not_active Expired
- 1982-08-05 DE DE8282107071T patent/DE3271363D1/de not_active Expired
- 1982-08-05 AT AT82107071T patent/ATE20058T1/de not_active IP Right Cessation
- 1982-08-09 PT PT75398A patent/PT75398B/pt not_active IP Right Cessation
- 1982-08-13 DK DK364682A patent/DK168818B1/da not_active IP Right Cessation
- 1982-08-13 AR AR290311A patent/AR231833A1/es active
- 1982-08-13 IL IL66542A patent/IL66542A0/xx not_active IP Right Cessation
- 1982-08-13 NZ NZ201578A patent/NZ201578A/en unknown
- 1982-08-13 JP JP57139986A patent/JPS5839670A/ja active Granted
- 1982-08-13 GR GR69039A patent/GR76255B/el unknown
- 1982-08-13 DD DD82242510A patent/DD206528A5/de unknown
- 1982-08-16 ES ES515031A patent/ES515031A0/es active Granted
- 1982-08-16 EG EG82499A patent/EG15752A/xx active
- 1982-08-16 BR BR8204776A patent/BR8204776A/pt unknown
- 1982-08-16 CA CA000409518A patent/CA1185981A/en not_active Expired
- 1982-08-16 TR TR21372A patent/TR21372A/xx unknown
- 1982-08-16 PL PL1982237928A patent/PL133290B1/pl unknown
- 1982-08-16 IE IE1978/82A patent/IE53871B1/en unknown
- 1982-08-16 ZA ZA825912A patent/ZA825912B/xx unknown
- 1982-08-17 HU HU822636A patent/HU190409B/hu not_active IP Right Cessation
- 1982-08-17 KR KR8203681A patent/KR890001547B1/ko not_active Expired
- 1982-08-17 CS CS826052A patent/CS228938B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8607782A (en) | 1983-02-24 |
| ZA825912B (en) | 1983-06-29 |
| DK364682A (da) | 1983-02-18 |
| PT75398B (en) | 1984-12-10 |
| JPS5839670A (ja) | 1983-03-08 |
| DE3271363D1 (en) | 1986-07-03 |
| KR890001547B1 (ko) | 1989-05-08 |
| GR76255B (en, 2012) | 1984-08-04 |
| IL66542A0 (en) | 1982-12-31 |
| ATE20058T1 (de) | 1986-06-15 |
| EP0076370B1 (de) | 1986-05-28 |
| IE53871B1 (en) | 1989-03-29 |
| PL237928A1 (en) | 1984-02-27 |
| NZ201578A (en) | 1985-01-31 |
| AU549479B2 (en) | 1986-01-30 |
| CA1185981A (en) | 1985-04-23 |
| PL133290B1 (en) | 1985-05-31 |
| ES8306480A1 (es) | 1983-06-01 |
| IE821978L (en) | 1983-02-17 |
| US4472416A (en) | 1984-09-18 |
| HU190409B (en) | 1986-09-29 |
| CS228938B2 (en) | 1984-05-14 |
| DK168818B1 (da) | 1994-06-20 |
| JPS6146474B2 (en, 2012) | 1986-10-14 |
| ES515031A0 (es) | 1983-06-01 |
| BR8204776A (pt) | 1983-08-02 |
| EP0076370A1 (de) | 1983-04-13 |
| AR231833A1 (es) | 1985-03-29 |
| KR840001141A (ko) | 1984-03-28 |
| EG15752A (en) | 1986-06-30 |
| TR21372A (tr) | 1984-04-25 |
| PT75398A (en) | 1982-09-01 |
| DD206528A5 (de) | 1984-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |