CH647513A5 - Triazol-derivate, deren herstellung und verwendung. - Google Patents

Triazol-derivate, deren herstellung und verwendung. Download PDF

Info

Publication number: CH647513A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; radical; butyl; ethanol; formula
Prior art date: 1979-11-13

Application number

CH8251/80A

Other languages

German (de)

English (en)

Inventor

Homer Kenneth Spencer

Original Assignee

Sandoz Ag

Priority date (The priority date 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 date listed.)

1979-11-13

Filing date

1980-11-06

Publication date

1985-01-31

1980-11-06 Application filed by Sandoz Ag filed Critical Sandoz Ag

1985-01-31 Publication of CH647513A5 publication Critical patent/CH647513A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 65
125000004432 carbon atom Chemical group C* 0.000 claims description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
241000233866 Fungi Species 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical group 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000013543 active substance Substances 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
150000004696 coordination complex Chemical class 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
239000000463 material Substances 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 27
239000000203 mixture Substances 0.000 description 23
230000005764 inhibitory process Effects 0.000 description 18
239000007921 spray Substances 0.000 description 15
241000209140 Triticum Species 0.000 description 13
235000021307 Triticum Nutrition 0.000 description 13
238000010998 test method Methods 0.000 description 12
241000221785 Erysiphales Species 0.000 description 10
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
239000004480 active ingredient Substances 0.000 description 9
230000000855 fungicidal effect Effects 0.000 description 9
229920000742 Cotton Polymers 0.000 description 8
240000008067 Cucumis sativus Species 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
244000299507 Gossypium hirsutum Species 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
235000013339 cereals Nutrition 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
241000220225 Malus Species 0.000 description 5
241000221300 Puccinia Species 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
235000021536 Sugar beet Nutrition 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
240000007154 Coffea arabica Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
241000221577 Uromyces appendiculatus Species 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
235000021016 apples Nutrition 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
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 3
240000001436 Antirrhinum majus Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000221787 Erysiphe Species 0.000 description 3
241001181537 Hemileia Species 0.000 description 3
206010061217 Infestation Diseases 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
-1 Sodium hydride Chemical class 0.000 description 3
240000003768 Solanum lycopersicum Species 0.000 description 3
244000301083 Ustilago maydis Species 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000007788 liquid Substances 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
235000021018 plums Nutrition 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
239000002904 solvent Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000593874 Chondrostereum purpureum Species 0.000 description 2
241001120669 Colletotrichum lindemuthianum Species 0.000 description 2
235000009849 Cucumis sativus Nutrition 0.000 description 2
241000371644 Curvularia ravenelii Species 0.000 description 2
241000510928 Erysiphe necator Species 0.000 description 2
241000223218 Fusarium Species 0.000 description 2
241000223221 Fusarium oxysporum Species 0.000 description 2
240000006240 Linum usitatissimum Species 0.000 description 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
241000221574 Melampsora lini Species 0.000 description 2
241000208181 Pelargonium Species 0.000 description 2
235000010632 Phaseolus coccineus Nutrition 0.000 description 2
244000042209 Phaseolus multiflorus Species 0.000 description 2
241000975369 Phoma betae Species 0.000 description 2
241000233614 Phytophthora Species 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
241001337928 Podosphaera leucotricha Species 0.000 description 2
241000221301 Puccinia graminis Species 0.000 description 2
241001123569 Puccinia recondita Species 0.000 description 2
241001123583 Puccinia striiformis Species 0.000 description 2
235000004789 Rosa xanthina Nutrition 0.000 description 2
241000109329 Rosa xanthina Species 0.000 description 2
241000561282 Thielaviopsis basicola Species 0.000 description 2
241001409775 Tranzschelia Species 0.000 description 2
241000221576 Uromyces Species 0.000 description 2
241000221566 Ustilago Species 0.000 description 2
235000015919 Ustilago maydis Nutrition 0.000 description 2
241000219094 Vitaceae Species 0.000 description 2
240000006365 Vitis vinifera Species 0.000 description 2
235000014787 Vitis vinifera Nutrition 0.000 description 2
239000008272 agar Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
244000038559 crop plants Species 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
235000021021 grapes Nutrition 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
241000894007 species Species 0.000 description 2
239000000758 substrate Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
PKHVUMMJMYKRNO-UHFFFAOYSA-N 2-(triazol-1-yl)ethanol Chemical compound OCCN1C=CN=N1 PKHVUMMJMYKRNO-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 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
241000221198 Basidiomycota Species 0.000 description 1
241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
241000222199 Colletotrichum Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 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
241000223194 Fusarium culmorum Species 0.000 description 1
241000223195 Fusarium graminearum Species 0.000 description 1
241000879841 Fusarium oxysporum f. cubense Species 0.000 description 1
241000427940 Fusarium solani Species 0.000 description 1
241000208152 Geranium Species 0.000 description 1
241000896246 Golovinomyces cichoracearum Species 0.000 description 1
241001181532 Hemileia vastatrix Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000896235 Leveillula Species 0.000 description 1
241000896221 Leveillula taurica Species 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
241001330975 Magnaporthe oryzae Species 0.000 description 1
241000219071 Malvaceae Species 0.000 description 1
241000221573 Melampsora Species 0.000 description 1
240000001140 Mimosa pudica Species 0.000 description 1
235000016462 Mimosa pudica Nutrition 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
241000498271 Necator 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
241000440444 Phakopsora Species 0.000 description 1
241000682645 Phakopsora pachyrhizi Species 0.000 description 1
241001503951 Phoma 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
241000896242 Podosphaera Species 0.000 description 1
241001516101 Puccinia pelargonii-zonalis Species 0.000 description 1
241000220324 Pyrus Species 0.000 description 1
239000006004 Quartz sand Substances 0.000 description 1
206010037888 Rash pustular Diseases 0.000 description 1
241001361634 Rhizoctonia Species 0.000 description 1
241000813090 Rhizoctonia solani Species 0.000 description 1
CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 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
241000222646 Stereum Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000865903 Thielaviopsis Species 0.000 description 1
240000000359 Triticum dicoccon Species 0.000 description 1
241000510929 Uncinula Species 0.000 description 1
241001319955 Unda Species 0.000 description 1
241000221561 Ustilaginales Species 0.000 description 1
235000009754 Vitis X bourquina Nutrition 0.000 description 1
235000012333 Vitis X labruscana Nutrition 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
150000001408 amides Chemical class 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
239000003899 bactericide agent Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 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
235000013532 brandy Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 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
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000021017 pears Nutrition 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
230000003032 phytopathogenic effect Effects 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
208000029561 pustule Diseases 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
229940043267 rhodamine b Drugs 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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)

CH8251/80A 1979-11-13 1980-11-06 Triazol-derivate, deren herstellung und verwendung. CH647513A5 (de)

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 (1)

Publication Number	Publication Date
CH647513A5 true CH647513A5 (de)	1985-01-31

Family

ID=26787917

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH8251/80A CH647513A5 (de)	1979-11-13	1980-11-06	Triazol-derivate, deren herstellung und verwendung.

Country Status (25)

Country	Link
AT (1)	AT378368B (fr)
AU (1)	AU545756B2 (fr)
BR (1)	BR8007385A (fr)
CA (1)	CA1171866A (fr)
CH (1)	CH647513A5 (fr)
CS (1)	CS235510B2 (fr)
DE (1)	DE3042302A1 (fr)
DK (1)	DK158041C (fr)
DZ (1)	DZ253A1 (fr)
EG (1)	EG14737A (fr)
ES (1)	ES496714A0 (fr)
FR (1)	FR2469408A1 (fr)
GB (1)	GB2064520B (fr)
GR (1)	GR71877B (fr)
HU (1)	HU185917B (fr)
IE (1)	IE51003B1 (fr)
IL (1)	IL61453A (fr)
IT (1)	IT1184252B (fr)
KE (1)	KE3668A (fr)
MY (2)	MY8600442A (fr)
NL (1)	NL185207C (fr)
PH (1)	PH17803A (fr)
PL (1)	PL126776B1 (fr)
PT (1)	PT72047B (fr)
YU (1)	YU289180A (fr)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
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
EP0047594A3 (fr) *	1980-08-18	1982-06-09	Imperial Chemical Industries Plc	Dérivés de triazole, leur procédé de préparation, leur utilisation comme fongicides et régulateurs de croissance des plantes
DE3175673D1 (en) *	1980-11-19	1987-01-15	Ici Plc	Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
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
EP0235714B1 (fr) *	1982-11-10	1990-08-29	Imperial Chemical Industries Plc	Procédé pour la préparation de composés ayant une double liaison carbone-carbone par déshydratation de l'alcool correspondant
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
DE3800094C2 (de) *	1987-01-14	1998-05-14	Ciba Geigy Ag	Verfahren und hydrophobe Zubereitung zur Bekämpfung von Schnittwundparasiten bei Pflanzen
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
ATE54313T1 (de) *	1987-01-21	1990-07-15	Ciba Geigy Ag	Mikrobizides mittel.
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 (fr) *	2004-06-18	2005-12-21	Bayer CropScience AG	Agent pour le traitement des semences de soja
WO2010149758A1 (fr)	2009-06-25	2010-12-29	Basf Se	Dérivés de 1,2,4-triazole antifongiques
JPWO2012165499A1 (ja)	2011-05-31	2015-02-23	株式会社クレハ	トリアゾール化合物、およびその利用
US20160029630A1 (en)	2012-11-27	2016-02-04	Basf Se	Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
CN105008336A (zh)	2012-11-27	2015-10-28	巴斯夫欧洲公司	取代2-[苯氧基苯基]-1-[1,2,4]三唑-1-基乙醇化合物及其作为杀真菌剂的用途
WO2014095548A1 (fr)	2012-12-19	2014-06-26	Basf Se	Composés triazoles substitués en [1,2,4] et leur utilisation comme fongicides
BR112015014579A2 (pt)	2012-12-19	2017-07-11	Basf Se	compostos da fórmula i, uso de um composto da fórmula i, método para combater fungos nocivos e sementes.
BR112015014753B8 (pt) *	2012-12-20	2020-03-03	Basf Agro Bv	composições, uso de uma composição, método para o combate de fungos fitopatogênicos e uso dos componentes
BR112015016446B1 (pt)	2013-01-09	2019-10-29	Basf Agro Bv	processo para preparar compostos de fórmula ii, solução aquosa e uso da solução aquosa
BR112016000299B8 (pt) *	2013-07-08	2021-04-20	Basf Agro Bv	composições, uso de uma composição, método para o combate dos fungos fitopatogênicos e uso dos componentes
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 (fr) *	2014-06-06	2015-12-09	Basf Se	Composés de [1,2,4] triazole substitué
AU2015281187B2 (en)	2014-06-25	2018-10-04	BASF Agro B.V.	Pesticidal compositions
US10053436B2 (en)	2014-07-08	2018-08-21	BASF Agro B.V.	Process for the preparation of substituted oxiranes and triazoles
UA120628C2 (uk)	2014-11-07	2020-01-10	Басф Се	Пестицидні суміші
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
WO2016180614A1 (fr)	2015-05-08	2016-11-17	Basf Se	Procédé de préparation de limonèn-4-ol
WO2016180642A1 (fr)	2015-05-08	2016-11-17	BASF Agro B.V.	Procédé de préparation de terpinolène époxyde
WO2017157920A1 (fr)	2016-03-16	2017-09-21	Basf Se	Utilisation de tétrazolinones pour lutter contre des champignons phytopathogènes résistants sur des fruits
EP3429357B1 (fr)	2016-03-16	2025-09-17	Basf Se	Utilisation d'une tétrazolinone spécifique pour lutter contre des champignons phytopathogènes résistants sur des céréales
US11241012B2 (en)	2016-03-16	2022-02-08	Basf Se	Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
KR20190017924A (ko)	2016-06-15	2019-02-20	바스프 아그로 비.브이.	4치환 알켄의 에폭시화 방법
ES2877169T3 (es)	2016-06-15	2021-11-16	Basf Agro Bv	Procedimiento para la epoxidación de un alqueno tetrasustituido
ES2891352T3 (es)	2017-06-14	2022-01-27	Basf Agro Bv	Proceso para la preparación de alcoholes fenoxifenil sustituidos
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 (fr)	2018-12-18	2020-06-24	BASF Agro B.V.	Procédé de préparation de cétones phénoxyphényle substituées
EP3670492A1 (fr)	2018-12-18	2020-06-24	BASF Agro B.V.	Procédé de préparation de 4-nitro-2-(trifluorométhyl)-1-(1-nitroethyl)-benzène
EP3670491A1 (fr)	2018-12-18	2020-06-24	BASF Agro B.V.	Procédé de préparation de 4-nitro-2-trifluorométhyle-acetophénone
EP3696164A1 (fr)	2019-02-14	2020-08-19	BASF Agro B.V.	Procede de preparation de 4-nitro-2-(trifluoromethyl)-benzonitrile
EP3696159A1 (fr)	2019-02-14	2020-08-19	BASF Agro B.V.	Procede pour la preparation de phénoxyphényl cétones substituées
EP3696165A1 (fr)	2019-02-14	2020-08-19	BASF Agro B.V.	Procede pour la preparation des 4-halophenoxy-2-trifluoromethyl-benzonitriles

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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 GB GB8036066A patent/GB2064520B/en not_active Expired
- 1980-11-10 IT IT50119/80A patent/IT1184252B/it active
- 1980-11-10 CA CA000364347A patent/CA1171866A/fr not_active Expired
- 1980-11-11 PT PT72047A patent/PT72047B/pt unknown
- 1980-11-11 GR GR63332A patent/GR71877B/el unknown
- 1980-11-11 AT AT0553580A patent/AT378368B/de not_active IP Right Cessation
- 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 HU HU802702A patent/HU185917B/hu unknown
- 1980-11-11 EG EG80704A patent/EG14737A/xx active
- 1980-11-12 NL NLAANVRAGE8006170,A patent/NL185207C/xx not_active IP Right Cessation
- 1980-11-12 FR FR8024029A patent/FR2469408A1/fr active Granted
- 1980-11-12 DZ DZ806017A patent/DZ253A1/fr active
- 1980-11-12 IE IE2353/80A patent/IE51003B1/en not_active IP Right Cessation
- 1980-11-12 PL PL1980227788A patent/PL126776B1/pl unknown
- 1980-11-12 YU YU02891/80A patent/YU289180A/xx unknown
- 1980-11-12 DK DK483680A patent/DK158041C/da not_active IP Right Cessation
- 1980-11-12 BR BR8007385A patent/BR8007385A/pt unknown
- 1980-11-12 CS CS807663A patent/CS235510B2/cs 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

Publication number	Publication date
YU289180A (en)	1983-09-30
IE51003B1 (en)	1986-09-03
NL185207B (nl)	1989-09-18
NL185207C (nl)	1990-02-16
DZ253A1 (fr)	2004-09-13
AU6426380A (en)	1981-05-21
GB2064520B (en)	1984-07-04
EG14737A (en)	1985-03-31
DK483680A (da)	1981-05-14
CS235510B2 (en)	1985-05-15
FR2469408A1 (fr)	1981-05-22
IL61453A (en)	1988-04-29
KE3668A (en)	1986-10-31
IL61453A0 (en)	1980-12-31
DE3042302C2 (fr)	1989-09-21
IT8050119A0 (it)	1980-11-10
PT72047A (en)	1980-12-01
ES8204428A1 (es)	1982-05-01
AT378368B (de)	1985-07-25
MY8600442A (en)	1986-12-31
CA1171866A (fr)	1984-07-31
AU545756B2 (en)	1985-08-01
MY8700561A (en)	1987-12-31
PT72047B (en)	1982-01-28
GR71877B (fr)	1983-08-02
FR2469408B1 (fr)	1983-06-24
ATA553580A (de)	1984-12-15
GB2064520A (en)	1981-06-17
IT1184252B (it)	1987-10-22
PH17803A (en)	1984-12-13
BR8007385A (pt)	1981-05-26
DE3042302A1 (de)	1981-08-27
DK158041C (da)	1990-08-13
NL8006170A (nl)	1981-06-01
ES496714A0 (es)	1982-05-01
HU185917B (en)	1985-04-28
PL126776B1 (en)	1983-08-31
IE802353L (en)	1981-05-13
PL227788A1 (fr)	1981-11-13
DK158041B (da)	1990-03-19

Legal Events

Date	Code	Title	Description
1997-05-15	PFA	Name/firm changed	Owner name: SANDOZ AG TRANSFER- NOVARTIS AG
2000-11-30	PL	Patent ceased

Publication	Publication Date	Title
DE3042302C2 (fr)	1989-09-21
DE2737489C2 (fr)	1991-07-11
DE3042303A1 (de)	1981-08-27	Organische verbindungen, deren herstellung und verwendung
DE2654890A1 (de)	1977-06-08	1,2,4-triazolverbindungen und diese verbindungen enthaltende fungizide mittel
EP0332579A2 (fr)	1989-09-13	Méthode de protection de plantes contre des maladies
US4432989A (en)	1984-02-21	αAryl-1H-imidazole-1-ethanols
DE2819879A1 (de)	1978-11-09	Imidazol- und triazolverbindungen, verfahren zu ihrer herstellung und sie enthaltende fungizide und das pflanzenwaschstum regulierende zusammensetzungen
DE2726043A1 (de)	1977-12-22	Triazolverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende zusammensetzungen
DE3877459T2 (de)	1993-05-13	Pyrimidinderivate.
DE2734426A1 (de)	1978-02-16	Zusammensetzung und verfahren zur bekaempfung von pilzen
EP0225886B1 (fr)	1990-06-20	Nouvelles compositions de pyridazine, leur procede de production et agents fongicides et anti-algues
DE2734365A1 (de)	1978-02-09	Heterocyclische verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende fungizide zusammensetzungen
EP0010143A2 (fr)	1980-04-30	Dérivés d'oxime pour la protection de plantes cultivées
EP0146047B1 (fr)	1991-05-22	Agent pour influencer la croissance des plantes
JPH0345065B2 (fr)	1991-07-09
EP0004315B1 (fr)	1981-02-25	Dérivés du 1.1-diphényléthène, procédé pour leur préparation et leur utilisation comme microbicides
DE2800010A1 (de)	1978-07-13	Pyrazinverbindungen
EP0390022A2 (fr)	1990-10-03	Azolyléthylcyclopropanes, leur procédé de préparation et leur application comme herbicides
DE2812662A1 (de)	1978-09-28	Imidazol-verbindungen
DD202235A5 (de)	1983-09-07	Fungizide mittel
DE2842801A1 (de)	1980-04-10	Beta-triazolyloxime
DE1567131A1 (de)	1970-05-27	Herbizide Komposition und Verfahren zu ihrer Anwendung
AT393589B (de)	1991-11-11	Fungizide mittel
DE2753823C2 (fr)	1987-06-11
EP0056087A1 (fr)	1982-07-21	Application d'alpha-azolylglycols comme régulateurs de la croissance des plantes