IE51003B1 - Fungicidal alpha-aryl 1h-1,2,4-triazole-1-ethanols - Google Patents
Fungicidal alpha-aryl 1h-1,2,4-triazole-1-ethanolsInfo
- Publication number
- IE51003B1 IE51003B1 IE2353/80A IE235380A IE51003B1 IE 51003 B1 IE51003 B1 IE 51003B1 IE 2353/80 A IE2353/80 A IE 2353/80A IE 235380 A IE235380 A IE 235380A IE 51003 B1 IE51003 B1 IE 51003B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- ethanol
- butyl
- triazole
- carbon atoms
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 239000000417 fungicide Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 9
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 23
- 241000233866 Fungi Species 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 150000003839 salts Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 239000002689 soil Substances 0.000 claims description 14
- 239000012141 concentrate Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 150000004696 coordination complex Chemical group 0.000 claims description 7
- -1 m-cyanophenyl Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004952 trihaloalkoxy group Chemical group 0.000 claims description 2
- 230000003032 phytopathogenic effect Effects 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000007921 spray Substances 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 13
- 244000046052 Phaseolus vulgaris Species 0.000 description 12
- 241000209140 Triticum Species 0.000 description 12
- 235000021307 Triticum Nutrition 0.000 description 12
- 238000010998 test method Methods 0.000 description 12
- 241000221785 Erysiphales Species 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 240000005979 Hordeum vulgare Species 0.000 description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000003359 percent control normalization Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- 241000221300 Puccinia Species 0.000 description 6
- 235000021536 Sugar beet Nutrition 0.000 description 6
- 241000221576 Uromyces Species 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 240000007154 Coffea arabica Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 240000006365 Vitis vinifera Species 0.000 description 5
- 235000014787 Vitis vinifera Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000220225 Malus Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 2-pyrrol-1-ylethanol Chemical compound OCCN1C=CC=C1 ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000371644 Curvularia ravenelii 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
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 241000221535 Pucciniales Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000003415 peat Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- PKHVUMMJMYKRNO-UHFFFAOYSA-N 2-(triazol-1-yl)ethanol Chemical compound OCCN1C=CN=N1 PKHVUMMJMYKRNO-UHFFFAOYSA-N 0.000 description 2
- AFIXWUUQSLBWBE-UHFFFAOYSA-N 2-tert-butyl-2-(4-methylphenyl)oxirane Chemical compound C1=CC(C)=CC=C1C1(C(C)(C)C)OC1 AFIXWUUQSLBWBE-UHFFFAOYSA-N 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241001444080 Aphanomyces euteiches Species 0.000 description 2
- 240000007087 Apium graveolens Species 0.000 description 2
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 2
- 235000010591 Appio Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 241000498271 Necator Species 0.000 description 2
- 241000440444 Phakopsora Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 244000141353 Prunus domestica Species 0.000 description 2
- 241001123569 Puccinia recondita Species 0.000 description 2
- 206010037888 Rash pustular Diseases 0.000 description 2
- 235000004789 Rosa xanthina Nutrition 0.000 description 2
- 241000109329 Rosa xanthina Species 0.000 description 2
- 241000222646 Stereum Species 0.000 description 2
- 241000865903 Thielaviopsis Species 0.000 description 2
- 241001409775 Tranzschelia Species 0.000 description 2
- 241000510929 Uncinula Species 0.000 description 2
- 244000301083 Ustilago maydis Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 208000029561 pustule Diseases 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000028070 sporulation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 1
- ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000380131 Ammophila arenaria Species 0.000 description 1
- 240000001436 Antirrhinum majus Species 0.000 description 1
- 241001444083 Aphanomyces Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000593874 Chondrostereum purpureum Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000010071 Cucumis prophetarum Nutrition 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PWNAWOCHVWERAR-UHFFFAOYSA-N Flumetralin Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CC)CC1=C(F)C=CC=C1Cl PWNAWOCHVWERAR-UHFFFAOYSA-N 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000879806 Fusarium oxysporum f. sp. vasinfectum Species 0.000 description 1
- 241000427940 Fusarium solani Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241001181532 Hemileia vastatrix Species 0.000 description 1
- 244000081841 Malus domestica Species 0.000 description 1
- 241000219071 Malvaceae Species 0.000 description 1
- 241000221574 Melampsora lini Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241001602876 Nata Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000208181 Pelargonium Species 0.000 description 1
- 241001503951 Phoma Species 0.000 description 1
- 241000975369 Phoma betae Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241001149949 Phytophthora cactorum Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000514450 Podocarpus latifolius Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000221301 Puccinia graminis Species 0.000 description 1
- 241001123583 Puccinia striiformis Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 240000000359 Triticum dicoccon Species 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 235000015919 Ustilago maydis Nutrition 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- LWXGIHBXXQBLEU-UHFFFAOYSA-N bis(2-tert-butyl-4-methylphenyl)methanone Chemical compound C(C)(C)(C)C1=C(C=CC(=C1)C)C(=O)C1=C(C=C(C=C1)C)C(C)(C)C LWXGIHBXXQBLEU-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001586 eradicative effect Effects 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical group [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE2159/84A IE51004B1 (en) | 1979-11-13 | 1980-11-12 | Fungicidal alpha-aryl 1h-1,2,4-triazole-1-ethanols |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9379979A | 1979-11-13 | 1979-11-13 | |
| US16861380A | 1980-07-14 | 1980-07-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE802353L IE802353L (en) | 1981-05-13 |
| IE51003B1 true IE51003B1 (en) | 1986-09-03 |
Family
ID=26787917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2353/80A IE51003B1 (en) | 1979-11-13 | 1980-11-12 | Fungicidal alpha-aryl 1h-1,2,4-triazole-1-ethanols |
Country Status (25)
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4927839A (en) * | 1979-03-07 | 1990-05-22 | Imperial Chemical Industries Plc | Method of preventing fungal attack on wood, hides, leather or paint films using a triazole |
| ATE81852T1 (de) * | 1980-08-18 | 1992-11-15 | Ici Plc | Triazol-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als fungizide und pflanzenwachstumsregulatoren. |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
| US4533659A (en) * | 1982-06-09 | 1985-08-06 | Ciba-Geigy Corporation | Microbicidal 2-(1H-1,2,4-triazolylmethyl-1'-yl)-2-siloxy-2-phenyl-acetates |
| US4517194A (en) * | 1982-06-25 | 1985-05-14 | Ciba-Geigy Corporation | Azolylmandelic acid derivatives and use thereof for controlling microorganisms |
| DE3337937A1 (de) * | 1982-10-28 | 1984-05-03 | Sandoz-Patent-GmbH, 7850 Lörrach | Neue azolderivate |
| DE3381852D1 (de) * | 1982-11-10 | 1990-10-04 | Ici Plc | Verfahren zur herstellung von verbindungen mit doppelter kohlenstoff-kohlenstoffbindung durch dehydrierung des korrespondierenden alkohols. |
| PH19709A (en) * | 1982-11-23 | 1986-06-16 | Ciba Geigy Ag | Microbicidal 1-carbonyl-1-phenoxyphenyl-2-azolylethanol derivatives |
| AT395363B (de) * | 1983-03-04 | 1992-12-10 | Sandoz Ag | Verfahren zur bekaempfung phytopathogener fungi |
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
| ATE66676T1 (de) * | 1983-05-19 | 1991-09-15 | Ciba Geigy Ag | Verfahren zur herstellung von 1triazolylethylether-derivaten, sowie mikrobizide mittel enthaltende neue 1-triazolyl- phenoxyphenylethylether-derivate als wirkstoffe und deren verwendung. |
| NL8402548A (nl) * | 1983-09-01 | 1985-04-01 | Sandoz Ag | Nieuwe azoolverbindingen. |
| CH668772A5 (de) * | 1984-07-13 | 1989-01-31 | Sandoz Ag | 1,2,4-triazol-derivat, verfahren zu dessen herstellung und seine verwendung. |
| GB8603951D0 (en) * | 1986-02-18 | 1986-03-26 | Ici Plc | Heterocyclic compounds |
| GB8617780D0 (en) * | 1986-07-21 | 1986-08-28 | Sandoz Ltd | Fungicides |
| FR2609368B1 (fr) * | 1987-01-14 | 1990-04-13 | Sandoz Sa Produits | Utilisation de derives du 1, 2, 4-triazole pour combattre les maladies de plaies de taille des plantes perennes |
| DE3800094C2 (de) * | 1987-01-14 | 1998-05-14 | Ciba Geigy Ag | Verfahren und hydrophobe Zubereitung zur Bekämpfung von Schnittwundparasiten bei Pflanzen |
| ES2016660B3 (es) * | 1987-01-21 | 1990-11-16 | Ciba-Geigy Ag | Agente microbicida. |
| BE1001499A5 (fr) * | 1988-07-14 | 1989-11-14 | Sandoz Sa | Procede pour combattre les maladies de plaies de taille des plantes perennes. |
| DE3909862A1 (de) * | 1989-03-25 | 1990-09-27 | Basf Ag | Azolylethylcyclopropane, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel |
| GB9307924D0 (en) * | 1993-04-16 | 1993-06-02 | Zeneca Ltd | Chrial synthesis |
| HU212424B (en) * | 1993-09-23 | 1996-06-28 | Richter Gedeon Vegyeszet | New propan-2-ol derivatives substituted with triazole or imidazole and process for producing them |
| EP1606999A1 (de) * | 2004-06-18 | 2005-12-21 | Bayer CropScience AG | Saatgutbehandlungsmittel für Soja |
| WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
| WO2012165499A1 (ja) | 2011-05-31 | 2012-12-06 | 株式会社クレハ | トリアゾール化合物、およびその利用 |
| WO2014082871A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| EP2928873A1 (en) | 2012-11-27 | 2015-10-14 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| EP2935237A1 (en) | 2012-12-19 | 2015-10-28 | Basf Se | Substituted [1,2,4]triazole compounds and their use as fungicides |
| EP3173406A1 (en) | 2012-12-19 | 2017-05-31 | Basf Se | Substituted [1,2,4]triazole compounds and their use as fungicides |
| CN105050406B (zh) * | 2012-12-20 | 2017-09-15 | 巴斯夫农业公司 | 包含三唑化合物的组合物 |
| EP3219707B1 (en) | 2013-01-09 | 2019-06-26 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
| EP3019013B1 (en) * | 2013-07-08 | 2020-12-23 | BASF Agro B.V. | Compositions comprising a triazole compound and a biopesticide |
| MX377786B (es) | 2013-12-18 | 2025-03-10 | Basf Agro Bv | Procedimiento para la preparacion de cetonas fenoxifenilicas sustituidas. |
| AR100743A1 (es) * | 2014-06-06 | 2016-10-26 | Basf Se | Compuestos de [1,2,4]triazol sustituido |
| EP2952507A1 (en) * | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
| UA119672C2 (uk) | 2014-06-25 | 2019-07-25 | Басф Агро Б.В. | Пестицидні композиції |
| ES2688377T3 (es) | 2014-07-08 | 2018-11-02 | BASF Agro B.V. | Proceso para la preparación de oxiranos y triazoles sustituidos |
| PL3214937T3 (pl) | 2014-11-07 | 2024-10-14 | Basf Se | Mieszaniny szkodnikobójcze |
| CN104814029B (zh) * | 2015-03-12 | 2017-10-17 | 南京林业大学 | 水载型复合有机木材防腐剂及其制备方法和应用 |
| EP3294700B1 (en) | 2015-05-08 | 2020-01-29 | BASF Agro B.V. | A process for the preparation of limonene-4-ol |
| US10344008B2 (en) | 2015-05-08 | 2019-07-09 | BASF Agro B.V. | Process for the preparation of terpinolene epoxide |
| BR112018068695B1 (pt) | 2016-03-16 | 2022-12-27 | Basf Se | Uso de um composto e método para controlar fungos fitopatogênicos |
| WO2017157916A1 (en) | 2016-03-16 | 2017-09-21 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean |
| CA3015744C (en) | 2016-03-16 | 2024-04-23 | Basf Se | Use of 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one for combating resistant phytopathogenic fungi on cereals |
| US11072593B2 (en) | 2016-06-15 | 2021-07-27 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| US10640477B2 (en) | 2016-06-15 | 2020-05-05 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| CN110740995B (zh) * | 2017-06-14 | 2023-07-14 | 巴斯夫农业公司 | 制备取代苯氧基苯基醇的方法 |
| CN107602547A (zh) * | 2017-09-28 | 2018-01-19 | 南开大学 | 一类杂环三唑衍生物及其制备方法和用途 |
| EP3670487A1 (en) | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of substituted phenoxyphenyl ketones |
| EP3670491A1 (en) | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-trifluoromethyl-acetophenone |
| EP3670492A1 (en) | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-(trifluoromethyl)-1-(1-nitroethyl)-benzene |
| EP3696165A1 (en) | 2019-02-14 | 2020-08-19 | BASF Agro B.V. | Process for the preparation of 4-halophenoxy-2-trifluoromethyl benzonitrile |
| EP3696164A1 (en) | 2019-02-14 | 2020-08-19 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-(trifluoromethyl)-benzonitrile |
| EP3696159A1 (en) | 2019-02-14 | 2020-08-19 | BASF Agro B.V. | Process for the preparation of substituted phenoxyphenyl ketones |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IE44186B1 (en) * | 1975-12-03 | 1981-09-09 | Ici Ltd | 1,2,4-triazolyl alkanols and their use as pesticides |
| IE45765B1 (en) * | 1976-08-19 | 1982-11-17 | Ici Ltd | Triazoles and imidazoles useful as plant fungicides and growth regulating agents |
| DE2738725A1 (de) * | 1977-08-27 | 1979-03-08 | Basf Ag | Azolylalkohole |
| DE2743767A1 (de) * | 1977-09-29 | 1979-04-12 | Bayer Ag | Diastereomere triazolyl-0,n-acetale, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1980
- 1980-11-06 CH CH8251/80A patent/CH647513A5/de not_active IP Right Cessation
- 1980-11-08 DE DE19803042302 patent/DE3042302A1/de active Granted
- 1980-11-10 IT IT50119/80A patent/IT1184252B/it active
- 1980-11-10 CA CA000364347A patent/CA1171866A/en not_active Expired
- 1980-11-10 GB GB8036066A patent/GB2064520B/en not_active Expired
- 1980-11-11 PT PT72047A patent/PT72047B/pt unknown
- 1980-11-11 EG EG80704A patent/EG14737A/xx active
- 1980-11-11 ES ES496714A patent/ES496714A0/es active Granted
- 1980-11-11 AU AU64263/80A patent/AU545756B2/en not_active Expired
- 1980-11-11 IL IL61453A patent/IL61453A/xx not_active IP Right Cessation
- 1980-11-11 AT AT0553580A patent/AT378368B/de not_active IP Right Cessation
- 1980-11-11 HU HU802702A patent/HU185917B/hu unknown
- 1980-11-11 GR GR63332A patent/GR71877B/el unknown
- 1980-11-12 FR FR8024029A patent/FR2469408A1/fr active Granted
- 1980-11-12 DK DK483680A patent/DK158041C/da not_active IP Right Cessation
- 1980-11-12 IE IE2353/80A patent/IE51003B1/en not_active IP Right Cessation
- 1980-11-12 NL NLAANVRAGE8006170,A patent/NL185207C/xx not_active IP Right Cessation
- 1980-11-12 PL PL1980227788A patent/PL126776B1/pl unknown
- 1980-11-12 CS CS807663A patent/CS235510B2/cs unknown
- 1980-11-12 BR BR8007385A patent/BR8007385A/pt unknown
- 1980-11-12 DZ DZ806017A patent/DZ253A1/fr active
- 1980-11-12 YU YU02891/80A patent/YU289180A/xx unknown
-
1981
- 1981-03-27 PH PH25440A patent/PH17803A/en unknown
-
1986
- 1986-10-14 KE KE3668A patent/KE3668A/xx unknown
- 1986-12-30 MY MY442/86A patent/MY8600442A/xx unknown
-
1987
- 1987-12-30 MY MY561/87A patent/MY8700561A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE51003B1 (en) | Fungicidal alpha-aryl 1h-1,2,4-triazole-1-ethanols | |
| US4992093A (en) | Azolylcyclopentanol derivatives and agricultural and horticultural composition containing the same as active ingredients | |
| US4438122A (en) | Combating fungi with 1-phenoxy-2-pyridinyl-alkanols | |
| GB2063260A (en) | alpha -aryl-1 -H-imidazole-1-ethanol Derivatives and their Use as Fungicides | |
| JPS58128378A (ja) | 置換された１−ヒドロキシアルキル−アゾリル誘導体類、それらの製造法および殺菌剤もしくは植物生長調節剤としての用途 | |
| JPS5912668B2 (ja) | トリアゾリル−ｏ，ｎ−アセタ−ルの製造法 | |
| JPH02237979A (ja) | （ベンジリデン）―アゾリルメチルシクロアルカン及びその殺菌剤としての用途 | |
| JPH02167273A (ja) | オキシラン類 | |
| JPS59175488A (ja) | トリアゾ−ル又はイミダゾ−ル化合物、その製造法及びそれを含有する殺カビ又は植物生長調整組成物 | |
| US4432989A (en) | αAryl-1H-imidazole-1-ethanols | |
| US4205075A (en) | Processes and composition for combating fungi | |
| JPH0216301B2 (enrdf_load_stackoverflow) | ||
| RU2047605C1 (ru) | Производные азола и промежуточные соединения для их получения | |
| JPS60215674A (ja) | トリアゾ−ル又はイミダゾ−ル化合物、その製造法及びそれを含有する殺カビ又は植物生長調節組成物 | |
| JPS59112904A (ja) | 殺菌剤 | |
| JPH0345065B2 (enrdf_load_stackoverflow) | ||
| JPS6026111B2 (ja) | 新規な１−アゾリル−４−ヒドロキシ−ブタン誘導体，その製造方法およびそれを活性成分として含有する殺菌剤組成物 | |
| US4766132A (en) | Aroylaminomethylpyridines, composition containing them, and method of combatting fungi using them | |
| JPS60222459A (ja) | （アリ−ルチオ）−ピリジルアルカノ−ル | |
| US4895589A (en) | Heterocyclic compounds | |
| JPS62149667A (ja) | 新規なアゾール誘導体、その製造法及び該誘導体を含有する農園芸用薬剤 | |
| JPS6344154B2 (enrdf_load_stackoverflow) | ||
| JPS59184177A (ja) | 殺菌活性を有するフラン誘導体 | |
| JPS61122279A (ja) | トリアゾリルメチルカルビノール‐アリールアセタール類 | |
| AT393589B (de) | Fungizide mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |