DE3019049A1 - Neue azolverbindungen - Google Patents
Neue azolverbindungenInfo
- Publication number
- DE3019049A1 DE3019049A1 DE19803019049 DE3019049A DE3019049A1 DE 3019049 A1 DE3019049 A1 DE 3019049A1 DE 19803019049 DE19803019049 DE 19803019049 DE 3019049 A DE3019049 A DE 3019049A DE 3019049 A1 DE3019049 A1 DE 3019049A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- optionally
- plants
- alkyl
- 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- Withdrawn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
- 150000003851 azoles Chemical class 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000000417 fungicide Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 9
- 229910052751 metal Chemical class 0.000 claims abstract description 8
- 239000002184 metal Chemical class 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- -1 aryloxyalkyl halide Chemical class 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 23
- 239000003085 diluting agent Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 230000001105 regulatory effect Effects 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 150000003333 secondary alcohols Chemical class 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 230000008635 plant growth Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 4
- 239000004094 surface-active agent Substances 0.000 claims 2
- 230000002538 fungal effect Effects 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 239000003630 growth substance Substances 0.000 abstract description 9
- 150000007513 acids Chemical class 0.000 abstract description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000001309 chloro group Chemical group Cl* 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 230000012010 growth Effects 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000005648 plant growth regulator Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000013339 cereals Nutrition 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 229910052727 yttrium Inorganic materials 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 238000003306 harvesting Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 230000009105 vegetative growth Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 240000000111 Saccharum officinarum Species 0.000 description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 description 3
- 241000209056 Secale Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005795 Imazalil Substances 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 229960002125 enilconazole Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000003966 growth inhibitor Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000003898 horticulture Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
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- 150000007522 mineralic acids Chemical class 0.000 description 2
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- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
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- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
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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 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
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- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
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- 238000010186 staining Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- 235000005074 zinc chloride Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Fertilizers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19803019049 DE3019049A1 (de) | 1980-05-19 | 1980-05-19 | Neue azolverbindungen |
CA000376539A CA1163638A (en) | 1980-05-19 | 1981-04-29 | Azole compounds, their preparation, their use for crop treatment, and agents for this purpose |
IL62749A IL62749A (en) | 1980-05-19 | 1981-04-29 | Azolyl-phenoxy-alkanol and alkanone derivatives,their manufacture and their use for treating plants |
US06/258,789 US4380546A (en) | 1980-05-19 | 1981-04-29 | Azole compounds, their preparation, their use for crop treatment, and agents for this purpose |
EP81103348A EP0040350B1 (de) | 1980-05-19 | 1981-05-04 | Neue Azolverbindungen, ihre Herstellung, ihre Verwendung zur Pflanzenbehandlung und Mittel dafür |
DE8181103348T DE3160937D1 (en) | 1980-05-19 | 1981-05-04 | Azole compounds, their preparation, their use in treating plants, and agents therefor |
AT81103348T ATE4710T1 (de) | 1980-05-19 | 1981-05-04 | Neue azolverbindungen, ihre herstellung, ihre verwendung zur pflanzenbehandlung und mittel dafuer. |
KR1019810001650A KR850000494B1 (ko) | 1980-05-19 | 1981-05-13 | 아졸 화합물의 제조방법 |
DD81229998A DD158845A5 (de) | 1980-05-19 | 1981-05-15 | Pflanzenbehandlungsmittel |
PL1981231192A PL127553B2 (en) | 1980-05-19 | 1981-05-15 | Agent for treating of plants |
BR8103029A BR8103029A (pt) | 1980-05-19 | 1981-05-15 | Composicoes para tratamento de plantas |
CS813671A CS225838B2 (en) | 1980-05-19 | 1981-05-18 | The fungicide agent and the agent for the regulation of the plant growth |
ZA00813281A ZA813281B (en) | 1980-05-19 | 1981-05-18 | Novel azole compounds,their preparation,their use for crop treatment,and agents for this purpose |
HU811407A HU186884B (en) | 1980-05-19 | 1981-05-18 | Fungicide compositions with activity of controlling growth of plants containing azole compounds as active agents, and process for producing the active agents |
NZ197127A NZ197127A (en) | 1980-05-19 | 1981-05-18 | Azole compounds and use for crop treatment |
PH25647A PH17873A (en) | 1980-05-19 | 1981-05-18 | Novel azole compounds,their preparation,their use for crop treatment,and agents for this purpose |
AU70673/81A AU539440B2 (en) | 1980-05-19 | 1981-05-18 | Azole compounds |
JP7362181A JPS5716870A (en) | 1980-05-19 | 1981-05-18 | Novel azole compound,manufacture,plant treating agent containing it and treatment thereby |
DK217681A DK160937C (da) | 1980-05-19 | 1981-05-18 | 1,2,4-triazolylforbindelser, fremgangsmaade til fremstilling af saadanne forbindelser og plantebeskyttelsesmiddel indeholdende disse forbindelser |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19803019049 DE3019049A1 (de) | 1980-05-19 | 1980-05-19 | Neue azolverbindungen |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3019049A1 true DE3019049A1 (de) | 1981-12-03 |
Family
ID=6102758
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19803019049 Withdrawn DE3019049A1 (de) | 1980-05-19 | 1980-05-19 | Neue azolverbindungen |
DE8181103348T Expired DE3160937D1 (en) | 1980-05-19 | 1981-05-04 | Azole compounds, their preparation, their use in treating plants, and agents therefor |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8181103348T Expired DE3160937D1 (en) | 1980-05-19 | 1981-05-04 | Azole compounds, their preparation, their use in treating plants, and agents therefor |
Country Status (18)
Country | Link |
---|---|
US (1) | US4380546A (en, 2012) |
EP (1) | EP0040350B1 (en, 2012) |
JP (1) | JPS5716870A (en, 2012) |
KR (1) | KR850000494B1 (en, 2012) |
AT (1) | ATE4710T1 (en, 2012) |
AU (1) | AU539440B2 (en, 2012) |
BR (1) | BR8103029A (en, 2012) |
CA (1) | CA1163638A (en, 2012) |
CS (1) | CS225838B2 (en, 2012) |
DD (1) | DD158845A5 (en, 2012) |
DE (2) | DE3019049A1 (en, 2012) |
DK (1) | DK160937C (en, 2012) |
HU (1) | HU186884B (en, 2012) |
IL (1) | IL62749A (en, 2012) |
NZ (1) | NZ197127A (en, 2012) |
PH (1) | PH17873A (en, 2012) |
PL (1) | PL127553B2 (en, 2012) |
ZA (1) | ZA813281B (en, 2012) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3321023A1 (de) * | 1983-06-10 | 1984-12-13 | Basf Ag, 6700 Ludwigshafen | Triazolylalkohole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
EP0150404A1 (de) * | 1984-01-12 | 1985-08-07 | BASF Aktiengesellschaft | Alpha-Halogen-phenoxyalkylketone, Phenoxyalkylketone, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Zwischenprodukte zur Herstellung von Fungiziden |
EP0163895A1 (de) * | 1984-05-04 | 1985-12-11 | BASF Aktiengesellschaft | Verfahren zur diastereoselektiven Reduktion von -Triazolyl ketonen zu ss-Triazolylcarbinolen |
EP0199982A2 (de) | 1985-04-01 | 1986-11-05 | BASF Aktiengesellschaft | Azolverbindungen, Verfahren zu ihrer Herstellung und Mittel zur Regulierung des Pflanzenwachstums |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3126022A1 (de) * | 1981-07-02 | 1983-01-13 | Basf Ag, 6700 Ludwigshafen | Azolverbindungen, verfahren zu ihrer herstellung und diese enthaltende fungizide |
DE3200414A1 (de) * | 1982-01-09 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Azolyl-thioether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren |
DE3209431A1 (de) * | 1982-03-16 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Phenoxypropyltriazolyl-ketone und -carbinole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE3211850A1 (de) * | 1982-03-31 | 1983-10-06 | Basf Ag | Triazolverbindungen, verfahren zu ihrer herstellung und diese enthaltende fungizide |
ATE24900T1 (de) * | 1982-04-22 | 1987-01-15 | Ici Plc | Antifungische azolyl-phenyl substituierte alicyclische alkohole. |
US4648988A (en) * | 1983-12-21 | 1987-03-10 | Janssen Pharmaceutica, N.V. | Water-dilutable wood-preserving liquids |
CA1249832A (en) * | 1984-02-03 | 1989-02-07 | Shionogi & Co., Ltd. | Azolyl cycloalkanol derivatives and agricultural fungicides |
DE3415486A1 (de) * | 1984-04-26 | 1985-10-31 | Basf Ag, 6700 Ludwigshafen | Azolverbindungen, verfahren zu ihrer herstellung und diese enthaltende fungizide |
IL75017A (en) * | 1984-05-04 | 1989-07-31 | Basf Ag | Diastereoselective reduction of alpha-triazolylketones to beta-triazolylcarbinols |
DE3420227A1 (de) * | 1984-05-30 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | Vinylazole, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von pilzen |
DE3437919A1 (de) * | 1984-10-17 | 1986-04-17 | Basf Ag, 6700 Ludwigshafen | Benzyloxyalkylazole und diese enthaltende fungizide |
DE3515309A1 (de) * | 1985-04-27 | 1986-10-30 | Basf Ag, 6700 Ludwigshafen | 1,3-dioxan-5-yl-alkyltriazole, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer |
DE3702301A1 (de) * | 1986-03-06 | 1987-09-10 | Bayer Ag | 2-hydroxyethyl-azol-derivate |
ATE54312T1 (de) * | 1986-03-06 | 1990-07-15 | Bayer Ag | 2-hydroxyethyl-azol-derivate. |
DE3642632A1 (de) * | 1986-12-13 | 1988-06-23 | Basf Ag | Verfahren zur herstellung von phenoxysubstituierten estern und zwischenprodukte hierfuer |
DE3709806A1 (de) * | 1987-03-25 | 1988-10-06 | Basf Ag | Mittel zur regulierung des pflanzenwachstums |
DE3721695A1 (de) * | 1987-07-01 | 1989-01-12 | Bayer Ag | 1-phenoxy-3-triazolyl-1-hexen-derivate |
DE3813129A1 (de) * | 1987-07-01 | 1989-01-12 | Bayer Ag | Hydroxyethyl-azolyl-derivate |
DE3800306A1 (de) * | 1988-01-08 | 1989-07-20 | Basf Ag | Tert.-butylalkinole, verfahren zu ihrer herstellung und deren verwendung |
WO2010029028A1 (de) * | 2008-09-09 | 2010-03-18 | Basf Se | Imidazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
US20110160056A1 (en) * | 2008-09-09 | 2011-06-30 | Basf Se | Triazole compounds, the use thereof and preparations containing these compounds |
WO2010029003A1 (de) * | 2008-09-09 | 2010-03-18 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
BRPI0918230A2 (pt) * | 2008-09-09 | 2015-12-08 | Basf Se | composto, composição de composto ativo, método para controlar fungos fitopatogênicos, medicamento, e, método para preparar um antimicótico |
JP2012502003A (ja) * | 2008-09-09 | 2012-01-26 | ビーエーエスエフ ソシエタス・ヨーロピア | トリアゾール化合物、その使用およびこれらの化合物を含む製剤 |
JP2012501997A (ja) * | 2008-09-10 | 2012-01-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌剤としてのイミダゾールおよびトリアゾール化合物 |
WO2010028974A1 (de) * | 2008-09-10 | 2010-03-18 | Basf Se | Imidazol- und triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
US20110172097A1 (en) * | 2008-09-22 | 2011-07-14 | Basf Se | Imidazole and Triazole Compounds, Their Use and Agents Containing The Same |
BRPI0918548A2 (pt) * | 2008-09-22 | 2015-09-22 | Basf Se | composto, combinação de ingrediente ativo, semente, método para combater fungos fitopatogênicos, medicamentos, e, método para preparar um antimicótico. |
US20110177950A1 (en) * | 2008-09-22 | 2011-07-21 | Basf Se | Imidazole and Triazole Compounds, Their Use and Agents Containing the Same |
WO2010040717A1 (de) * | 2008-10-07 | 2010-04-15 | Basf Se | Triazol- und imidazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
MX2011003401A (es) * | 2008-10-07 | 2011-04-26 | Basf Se | Compuestos de triazol e imidazol, uso de los mismos y agentes que los contienen. |
JP2013056832A (ja) * | 2010-01-12 | 2013-03-28 | Univ Of Tokyo | ストリゴラクトン生合成阻害剤 |
WO2011110583A2 (en) * | 2010-03-10 | 2011-09-15 | Basf Se | Fungicidal mixtures comprising triazole derivatives |
CN116082245B (zh) * | 2022-12-26 | 2024-11-22 | 武汉工程大学 | 一种恩康唑晶体及其制备方法和应用 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3658813A (en) * | 1970-01-13 | 1972-04-25 | Janssen Pharmaceutica Nv | 1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles |
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 |
DE2423987C2 (de) * | 1974-05-17 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
DE2429513A1 (de) * | 1974-06-20 | 1976-01-15 | Bayer Ag | Eckige klammer auf 1-imidazolyl-(1) eckige klammer zu-eckige klammer auf 2-(4'(4''-chlorphenyl)-phenoxy eckige klammer zu -4,4-dimethyl-pentan-3-on und seine salze, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
DE2431073A1 (de) * | 1974-06-28 | 1976-01-15 | Bayer Ag | Fungizides mittel |
GB1535777A (en) * | 1975-08-26 | 1978-12-13 | Ici Ltd | Imidazole and 1,2,4-triazole compounds and their use as pesticides |
DE2600799A1 (de) * | 1976-01-10 | 1977-07-14 | Bayer Ag | Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
GB1601453A (en) * | 1977-05-05 | 1981-10-28 | Ici Ltd | Triazole and imidazole derivatives useful in agriculture |
DE2720949A1 (de) * | 1977-05-10 | 1978-11-23 | Bayer Ag | Azolylaether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
DE2738725A1 (de) * | 1977-08-27 | 1979-03-08 | Basf Ag | Azolylalkohole |
JPS6053018B2 (ja) * | 1977-09-07 | 1985-11-22 | 住友化学工業株式会社 | アゾ−ル系化合物、その製造法および該化合物からなる殺菌剤 |
DE2800544A1 (de) * | 1978-01-07 | 1979-07-19 | Bayer Ag | Carbamoyl-triazolyl-o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE2832234A1 (de) * | 1978-07-21 | 1980-01-31 | Bayer Ag | Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE2842137A1 (de) * | 1978-09-28 | 1980-04-17 | Bayer Ag | Halogenierte 1-azolyl-1-fluorphenoxy- butan-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1980
- 1980-05-19 DE DE19803019049 patent/DE3019049A1/de not_active Withdrawn
-
1981
- 1981-04-29 IL IL62749A patent/IL62749A/xx not_active IP Right Cessation
- 1981-04-29 US US06/258,789 patent/US4380546A/en not_active Expired - Lifetime
- 1981-04-29 CA CA000376539A patent/CA1163638A/en not_active Expired
- 1981-05-04 EP EP81103348A patent/EP0040350B1/de not_active Expired
- 1981-05-04 DE DE8181103348T patent/DE3160937D1/de not_active Expired
- 1981-05-04 AT AT81103348T patent/ATE4710T1/de not_active IP Right Cessation
- 1981-05-13 KR KR1019810001650A patent/KR850000494B1/ko not_active Expired
- 1981-05-15 PL PL1981231192A patent/PL127553B2/xx unknown
- 1981-05-15 BR BR8103029A patent/BR8103029A/pt unknown
- 1981-05-15 DD DD81229998A patent/DD158845A5/de not_active IP Right Cessation
- 1981-05-18 NZ NZ197127A patent/NZ197127A/xx unknown
- 1981-05-18 DK DK217681A patent/DK160937C/da not_active IP Right Cessation
- 1981-05-18 CS CS813671A patent/CS225838B2/cs unknown
- 1981-05-18 HU HU811407A patent/HU186884B/hu unknown
- 1981-05-18 ZA ZA00813281A patent/ZA813281B/xx unknown
- 1981-05-18 PH PH25647A patent/PH17873A/en unknown
- 1981-05-18 JP JP7362181A patent/JPS5716870A/ja active Granted
- 1981-05-18 AU AU70673/81A patent/AU539440B2/en not_active Ceased
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3321023A1 (de) * | 1983-06-10 | 1984-12-13 | Basf Ag, 6700 Ludwigshafen | Triazolylalkohole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
EP0150404A1 (de) * | 1984-01-12 | 1985-08-07 | BASF Aktiengesellschaft | Alpha-Halogen-phenoxyalkylketone, Phenoxyalkylketone, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Zwischenprodukte zur Herstellung von Fungiziden |
EP0163895A1 (de) * | 1984-05-04 | 1985-12-11 | BASF Aktiengesellschaft | Verfahren zur diastereoselektiven Reduktion von -Triazolyl ketonen zu ss-Triazolylcarbinolen |
EP0199982A2 (de) | 1985-04-01 | 1986-11-05 | BASF Aktiengesellschaft | Azolverbindungen, Verfahren zu ihrer Herstellung und Mittel zur Regulierung des Pflanzenwachstums |
Also Published As
Publication number | Publication date |
---|---|
ZA813281B (en) | 1982-06-30 |
NZ197127A (en) | 1983-04-12 |
CS225838B2 (en) | 1984-02-13 |
IL62749A (en) | 1984-11-30 |
JPH0420911B2 (en, 2012) | 1992-04-07 |
IL62749A0 (en) | 1981-06-29 |
US4380546A (en) | 1983-04-19 |
DK217681A (da) | 1981-11-20 |
KR850000494B1 (ko) | 1985-04-11 |
KR830006225A (ko) | 1983-09-20 |
EP0040350B1 (de) | 1983-09-21 |
PL127553B2 (en) | 1983-11-30 |
PL231192A2 (en, 2012) | 1982-01-18 |
HU186884B (en) | 1985-10-28 |
EP0040350A1 (de) | 1981-11-25 |
JPS5716870A (en) | 1982-01-28 |
AU7067381A (en) | 1981-11-26 |
DK160937C (da) | 1991-10-21 |
DK160937B (da) | 1991-05-06 |
BR8103029A (pt) | 1982-02-09 |
DD158845A5 (de) | 1983-02-09 |
ATE4710T1 (de) | 1983-10-15 |
DE3160937D1 (en) | 1983-10-27 |
AU539440B2 (en) | 1984-09-27 |
CA1163638A (en) | 1984-03-13 |
PH17873A (en) | 1985-01-14 |
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