DD215462A5 - Fungizide mittel - Google Patents

Fungizide mittel Download PDF

Info

Publication number: DD215462A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; optionally substituted; formula; methyl; alkyl
Prior art date: 1982-11-15

Application number

DD83256667A

Other languages

German (de)

English (en)

Inventor

Wolfgang Kraemer

Karl H Buechel

Graham Holmwood

Erik Regel

Paul Reinecke

Wilhelm Brandes

Original Assignee

Bayer 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.)

1982-11-15

Filing date

1983-11-14

Publication date

1984-11-14

1983-11-14 Application filed by Bayer Ag filed Critical Bayer Ag

1984-11-14 Publication of DD215462A5 publication Critical patent/DD215462A5/de

Links

239000000417 fungicide Substances 0.000 title claims description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 18
239000002253 acid Substances 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
229910052751 metal Chemical class 0.000 claims abstract description 10
239000002184 metal Chemical class 0.000 claims abstract description 10
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 7
230000000855 fungicidal effect Effects 0.000 claims abstract description 6
IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract description 5
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract description 4
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 4
125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims abstract description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 3
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 3
-1 dioxolan-2-yl Chemical group 0.000 claims description 80
238000000034 method Methods 0.000 claims description 47
150000001875 compounds Chemical class 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 40
239000000460 chlorine Substances 0.000 claims description 38
239000003921 oil Substances 0.000 claims description 33
239000000203 mixture Substances 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000004995 haloalkylthio group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000004438 haloalkoxy group Chemical group 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
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
239000011814 protection agent Substances 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
241000233866 Fungi Species 0.000 claims 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 7
125000005879 dioxolanyl group Chemical group 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
235000002639 sodium chloride Nutrition 0.000 description 16
150000002576 ketones Chemical class 0.000 description 15
239000007858 starting material Substances 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
239000003960 organic solvent Substances 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000003085 diluting agent Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000002585 base Substances 0.000 description 9
150000002924 oxiranes Chemical class 0.000 description 9
239000000126 substance Substances 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000012071 phase Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
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 5
239000004480 active ingredient Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000009835 boiling Methods 0.000 description 5
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000008187 granular material Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
238000002955 isolation Methods 0.000 description 5
150000002902 organometallic compounds Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
238000005554 pickling Methods 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
FWHFTQXMTWUZJR-UHFFFAOYSA-N 1-(1,2,4-triazol-4-yl)butan-2-ol Chemical compound CCC(O)CN1C=NN=C1 FWHFTQXMTWUZJR-UHFFFAOYSA-N 0.000 description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
LYKMESDYTURFJE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-(1,3-dioxolan-2-yl)-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)(C)C1OCCO1 LYKMESDYTURFJE-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
SNXWTJHCMDIPCN-UHFFFAOYSA-N C1=CNC2=C1O2 Chemical class C1=CNC2=C1O2 SNXWTJHCMDIPCN-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
150000003851 azoles Chemical class 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
150000002440 hydroxy compounds Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
150000002901 organomagnesium compounds Chemical class 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
238000005507 spraying Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
UPZUWFGCTWMOAG-UHFFFAOYSA-N 1-(4-chlorophenoxy)-2-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O)COC1=CC=C(Cl)C=C1 UPZUWFGCTWMOAG-UHFFFAOYSA-N 0.000 description 2
YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 2
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
SGKSEUBLNUWHPF-UHFFFAOYSA-N 2-[2-[2-[(4-fluorophenoxy)methyl]oxiran-2-yl]propan-2-yl]-1,3-dioxolane Chemical compound C1OC1(COC=1C=CC(F)=CC=1)C(C)(C)C1OCCO1 SGKSEUBLNUWHPF-UHFFFAOYSA-N 0.000 description 2
SKSGRDHIXHTURP-UHFFFAOYSA-N 2-[2-[2-[2-(2,4-dichlorophenyl)ethyl]oxiran-2-yl]propan-2-yl]-1,3-dioxolane Chemical compound C1OC1(CCC=1C(=CC(Cl)=CC=1)Cl)C(C)(C)C1OCCO1 SKSGRDHIXHTURP-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
229920001817 Agar Polymers 0.000 description 2
241001465180 Botrytis Species 0.000 description 2
241000123650 Botrytis cinerea Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
241000221300 Puccinia Species 0.000 description 2
241001123569 Puccinia recondita Species 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000008272 agar Substances 0.000 description 2
125000003172 aldehyde group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/185—Saturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Environmental Sciences (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Health & Medical Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyrrole Compounds (AREA)
Polymerization Catalysts (AREA)
Peptides Or Proteins (AREA)
Steroid Compounds (AREA)
Detergent Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD83256667A 1982-11-15 1983-11-14 Fungizide mittel DD215462A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823242252 DE3242252A1 (de)	1982-11-15	1982-11-15	Heterocyclisch substituierte hydroxyalkyl-azolyl-derivate

Publications (1)

Publication Number	Publication Date
DD215462A5 true DD215462A5 (de)	1984-11-14

Family

ID=6178198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83256667A DD215462A5 (de)	1982-11-15	1983-11-14	Fungizide mittel

Country Status (21)

Country	Link
US (1)	US4639462A (fr)
EP (2)	EP0193642B1 (fr)
JP (1)	JPS59104380A (fr)
KR (1)	KR900003302B1 (fr)
AT (2)	ATE25978T1 (fr)
AU (2)	AU565099B2 (fr)
BR (1)	BR8306240A (fr)
CA (1)	CA1212951A (fr)
DD (1)	DD215462A5 (fr)
DE (3)	DE3242252A1 (fr)
DK (1)	DK520683A (fr)
ES (1)	ES527258A0 (fr)
GR (1)	GR79069B (fr)
HU (1)	HU194483B (fr)
IE (1)	IE56307B1 (fr)
IL (1)	IL70197A (fr)
NZ (1)	NZ206251A (fr)
PH (1)	PH19094A (fr)
PT (1)	PT77619B (fr)
TR (1)	TR22215A (fr)
ZA (1)	ZA838468B (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
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DE3426906A1 (de) *	1984-07-20	1986-01-30	Bayer Ag, 5090 Leverkusen	Verfahren und zwischenprodukte zur synthese diastereomerer verbindungen
DE3436452A1 (de) *	1984-10-05	1986-04-10	Bayer Ag, 5090 Leverkusen	Antimykotisches mittel
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
DE3813841A1 (de) *	1987-06-03	1988-12-15	Bayer Ag	Heterocyclische hydroxyethylazole
DE3827134A1 (de) *	1988-08-10	1990-03-15	Bayer Ag	Substituierte triazolyl- bzw. imidazolyl-hydroxyalkyldioxolane, verfahren zu ihrer herstellung und ihre verwendung als mikrobizide, oxiranyldioxolane, dioxolanylketone, oxiranylketone und (alpha)-halogenketone als zwischenprodukte und verfahren zu deren herstellung
GB8819308D0 (en) *	1988-08-13	1988-09-14	Pfizer Ltd	Triazole antifungal agents
GB9002375D0 (en) *	1990-02-02	1990-04-04	Pfizer Ltd	Triazole antifungal agents
US6777217B1 (en)	1996-03-26	2004-08-17	President And Fellows Of Harvard College	Histone deacetylases, and uses related thereto
US20030129724A1 (en)	2000-03-03	2003-07-10	Grozinger Christina M.	Class II human histone deacetylases, and uses related thereto
WO2002089782A2 (fr) *	2001-05-09	2002-11-14	President And Fellows Of Harvard College	Dioxanes et leurs utilisations
US7244853B2 (en)	2001-05-09	2007-07-17	President And Fellows Of Harvard College	Dioxanes and uses thereof
US8999289B2 (en)	2005-03-22	2015-04-07	President And Fellows Of Harvard College	Treatment of protein degradation disorders
US8222423B2 (en)	2006-02-14	2012-07-17	Dana-Farber Cancer Institute, Inc.	Bifunctional histone deacetylase inhibitors
WO2007095584A2 (fr)	2006-02-14	2007-08-23	The President And Fellows Of Harvard College	Inhibiteurs de l'histone desacetylase
US8304451B2 (en)	2006-05-03	2012-11-06	President And Fellows Of Harvard College	Histone deacetylase and tubulin deacetylase inhibitors
AU2009274549B2 (en)	2008-07-23	2014-05-01	Dana-Farber Cancer Institute, Inc.	Deacetylase inhibitors and uses thereof
WO2011019393A2 (fr)	2009-08-11	2011-02-17	President And Fellows Of Harvard College	Inhibiteurs de hdac classe- et isoforme-spécifiques et utilisations de ceux-ci
US8822679B2 (en) *	2011-06-24	2014-09-02	California Institute Of Technology	Quaternary heteroatom containing compounds
US20130267699A1 (en)	2011-06-24	2013-10-10	California Institute Of Technology	Quaternary heteroatom containing compounds
US10421696B2 (en)	2014-12-18	2019-09-24	California Institute Of Technology	Enantioselective synthesis of α-quaternary mannich adducts by palladium-catalyzed allylic alkylation
WO2017156239A1 (fr)	2016-03-11	2017-09-14	California Institute Of Technology	Compositions et procédés d'acylation de lactames
EP3480190B1 (fr)	2017-11-01	2023-01-04	California Institute of Technology	Procédés d'alkylation allylique énantiosélective d'esters, lactones et lactames avec des alcools allyliques inactivés
US11214568B2 (en)	2018-10-18	2022-01-04	California Institute Of Technology	Gem-disubstituted pyrrolidines, piperazines, and diazepanes, and compositions and methods of making the same
EP4130094B1 (fr) *	2020-03-31	2024-11-27	Namics Corporation	Catalyseur de durcissement, composition de résine, matériau d'étanchéité, adhésif et produit durci

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3018866A1 (de) *	1980-05-16	1981-11-26	Bayer Ag, 5090 Leverkusen	1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide
DE3025879A1 (de) *	1980-07-09	1982-02-11	Basf Ag, 6700 Ludwigshafen	1,3-dioxan-5-yl-alkyltriazole, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer
AU7341381A (en) *	1980-08-20	1982-02-25	Imperial Chemical Industries Ltd.	Azoles
AU553482B2 (en) *	1980-08-28	1986-07-17	Imperial Chemical Industries Plc	Pharmaceutical compositions of fungicidal triazole derivatives
ZA817473B (en) *	1980-11-19	1982-10-27	Ici Plc	Triazole and imidazole compounds
DE3113628A1 (de) *	1981-04-04	1982-10-21	Basf Ag, 6700 Ludwigshafen	Fungizide mittel, enthaltend triazolylderivate und verfahren zur bekaempfung von pilzen mit ihnen
DE3275088D1 (en) *	1981-08-19	1987-02-19	Ici Plc	Triazole derivatives, processes for preparing them, compositions containing them and processes for combating fungi and regulating plant growth
DE3202601A1 (de) *	1982-01-27	1983-08-04	Bayer Ag, 5090 Leverkusen	Substituierte 1 -hydroxyalkyl-azolyl-derivate, verfahren zu ihrer herstellung sowie ihrer verwendung als fungizide und pflanzenwachstumsregulatoren
DE3202604A1 (de) *	1982-01-27	1983-08-04	Bayer Ag, 5090 Leverkusen	Ether-derivate von substituierten 1-hydroxyalkyl-azolen, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren
DE3242236A1 (de) *	1982-11-15	1984-05-17	Bayer Ag, 5090 Leverkusen	"antimykotische mittel"
DE3242222A1 (de) *	1982-11-15	1984-05-17	Bayer Ag, 5090 Leverkusen	Hydroxyalkinyl-azolyl-derivate

1982
- 1982-11-15 DE DE19823242252 patent/DE3242252A1/de not_active Withdrawn
1983
- 1983-10-21 PH PH29738A patent/PH19094A/en unknown
- 1983-11-01 US US06/547,807 patent/US4639462A/en not_active Expired - Fee Related
- 1983-11-04 EP EP85113427A patent/EP0193642B1/fr not_active Expired - Lifetime
- 1983-11-04 AT AT83110995T patent/ATE25978T1/de active
- 1983-11-04 AT AT85113427T patent/ATE50994T1/de active
- 1983-11-04 DE DE8383110995T patent/DE3370329D1/de not_active Expired
- 1983-11-04 EP EP83110995A patent/EP0111711B1/fr not_active Expired
- 1983-11-04 DE DE8585113427T patent/DE3381314D1/de not_active Expired - Lifetime
- 1983-11-07 AU AU21036/83A patent/AU565099B2/en not_active Ceased
- 1983-11-07 PT PT77619A patent/PT77619B/pt not_active IP Right Cessation
- 1983-11-11 IL IL70197A patent/IL70197A/xx unknown
- 1983-11-11 JP JP58211118A patent/JPS59104380A/ja active Pending
- 1983-11-14 DD DD83256667A patent/DD215462A5/de not_active IP Right Cessation
- 1983-11-14 CA CA000441096A patent/CA1212951A/fr not_active Expired
- 1983-11-14 HU HU833904A patent/HU194483B/hu not_active IP Right Cessation
- 1983-11-14 IE IE2650/83A patent/IE56307B1/xx unknown
- 1983-11-14 GR GR72965A patent/GR79069B/el unknown
- 1983-11-14 ZA ZA838468A patent/ZA838468B/xx unknown
- 1983-11-14 DK DK520683A patent/DK520683A/da not_active Application Discontinuation
- 1983-11-14 BR BR8306240A patent/BR8306240A/pt unknown
- 1983-11-14 ES ES527258A patent/ES527258A0/es active Granted
- 1983-11-14 NZ NZ206251A patent/NZ206251A/en unknown
- 1983-11-15 KR KR1019830005409A patent/KR900003302B1/ko not_active Expired
- 1983-11-15 TR TR22215A patent/TR22215A/xx unknown
1987
- 1987-03-23 AU AU70527/87A patent/AU593337B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IL70197A0 (en)	1984-02-29
PT77619A (en)	1983-12-01
AU2103683A (en)	1984-06-21
IE56307B1 (en)	1991-06-19
DK520683A (da)	1984-05-16
EP0193642A2 (fr)	1986-09-10
DE3370329D1 (en)	1987-04-23
AU593337B2 (en)	1990-02-08
PH19094A (en)	1985-12-19
BR8306240A (pt)	1984-06-19
ATE25978T1 (de)	1987-04-15
AU565099B2 (en)	1987-09-03
EP0193642B1 (fr)	1990-03-14
DE3242252A1 (de)	1984-05-17
CA1254574C (fr)	1989-05-23
PT77619B (en)	1986-03-19
DK520683D0 (da)	1983-11-14
AU7052787A (en)	1987-07-02
EP0193642A3 (en)	1986-12-17
CA1212951A (fr)	1986-10-21
DE3381314D1 (de)	1990-04-19
NZ206251A (en)	1986-11-12
ATE50994T1 (de)	1990-03-15
EP0111711A2 (fr)	1984-06-27
ES8406155A1 (es)	1984-07-16
IL70197A (en)	1987-03-31
KR840006647A (ko)	1984-12-01
TR22215A (tr)	1986-10-06
KR900003302B1 (ko)	1990-05-14
ZA838468B (en)	1984-07-25
EP0111711A3 (en)	1984-10-03
EP0111711B1 (fr)	1987-03-18
IE832650L (en)	1984-05-15
HU194483B (en)	1988-02-29
ES527258A0 (es)	1984-07-16
GR79069B (fr)	1984-10-02
JPS59104380A (ja)	1984-06-16
US4639462A (en)	1987-01-27

Legal Events

Date	Code	Title	Description
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0111711B1 (fr)	1987-03-18	Dérivés hydroxyalkyl-azolyles substitués par des hétérocycles
EP0110048B1 (fr)	1986-12-03	Dérivés 1-hydroxyéthyl triazoliques substitués
EP0054865B1 (fr)	1986-02-26	1-Azolyl-butan-2-ones substitués, procédé de leur préparation et leur application comme fongicides ainsi que comme intermédiaires
EP0019189B1 (fr)	1982-07-28	Agents fongicides, procédé pour leur préparation, ainsi que leur utilisation comme fongicides
EP0121171B1 (fr)	1989-05-10	Fongicides, leur procédé de préparation et leur application
EP0111234B1 (fr)	1986-10-08	Agents fongicides, leur préparation et utilisation
EP0121888B1 (fr)	1988-05-25	Dérivés 1-azolyl-3-pyrazolyl-2-propanols, leur procédé de préparation et leur application comme fongicides
EP0104549B1 (fr)	1987-07-29	Azolylbutanoles
EP0131845A2 (fr)	1985-01-23	Utilisation de diazolylalkylecarbinols substitués pour la protection de plantes contre les champignons
EP0047405A2 (fr)	1982-03-17	Dérivés azolylalkyles, leur procédé de préparation et leur application comme fongicides
EP0118069B1 (fr)	1986-12-30	Fongicides contenant des 1,3-diazolyl-propanols
EP0102578B1 (fr)	1986-07-30	2-Aryl-2-azolylméthyl-1,3-dioxépines
DE3021551A1 (de)	1981-12-24	4-substituierte 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-one und -ole, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0141204B1 (fr)	1990-05-02	Dérivés de hydroxyéthylazoles
EP0057864B1 (fr)	1984-10-03	Dérivés de 2-azolylméthyl-1,3-dioxolanne et - dioxanne, procédé pour leur préparation et leur application comme fongicide
EP0102591B1 (fr)	1986-12-30	Ethers azolyl-cétones et -carbinoles substitués
EP0019190B1 (fr)	1983-03-30	Utilisation des hydroxyalkyl-imidazoles comme fongicides
EP0405267A1 (fr)	1991-01-02	Dérivés de l'hydroxyéthyl-cyclopropyl-azolyle
CA1254574A (fr)	1989-05-23	Derives de substitution heterocyclises d'hydroxyalcoylazolyle
EP0182188A2 (fr)	1986-05-28	Triazolylméthylcarbinol-arylacétales
EP0405240A1 (fr)	1991-01-02	Utilisation de dérivés bis-azolylés substitués pour la lutte contre les champignons dans la protection des plantes
DD202613A5 (de)	1983-09-28	Fungizide mittel