IE55403B1 - Hydroxyalkynyl-azolyl derivatives,processes for their preparation and their use as fungicides - Google Patents
Hydroxyalkynyl-azolyl derivatives,processes for their preparation and their use as fungicidesInfo
- Publication number
- IE55403B1 IE55403B1 IE1368/83A IE136883A IE55403B1 IE 55403 B1 IE55403 B1 IE 55403B1 IE 1368/83 A IE1368/83 A IE 1368/83A IE 136883 A IE136883 A IE 136883A IE 55403 B1 IE55403 B1 IE 55403B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- carbon atoms
- phenyl
- hydroxyalkynyl
- bromine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 18
- 239000000417 fungicide Substances 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052751 metal Chemical class 0.000 claims abstract description 15
- 239000002184 metal Chemical class 0.000 claims abstract description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 52
- -1 phenoxy, phenylthio Chemical group 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 150000001398 aluminium Chemical class 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 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000007259 addition reaction Methods 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 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
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
- 125000004660 phenylalkylthio group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims 5
- 150000004696 coordination complex Chemical class 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 10
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 17
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- 239000000203 mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
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- 238000012360 testing method Methods 0.000 description 9
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- 238000009472 formulation Methods 0.000 description 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
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- 239000008187 granular material Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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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
- A01N43/48—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
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
- C07C33/483—Monocyclic
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823222191 DE3222191A1 (de) | 1982-06-12 | 1982-06-12 | Hydroxyalkinyl-azolyl-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE831368L IE831368L (en) | 1983-12-12 |
| IE55403B1 true IE55403B1 (en) | 1990-09-12 |
Family
ID=6165954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1368/83A IE55403B1 (en) | 1982-06-12 | 1983-06-10 | Hydroxyalkynyl-azolyl derivatives,processes for their preparation and their use as fungicides |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4578396A (en, 2012) |
| EP (2) | EP0096786B1 (en, 2012) |
| JP (1) | JPS5921667A (en, 2012) |
| AT (2) | ATE45350T1 (en, 2012) |
| AU (1) | AU567100B2 (en, 2012) |
| BR (1) | BR8303091A (en, 2012) |
| CS (1) | CS236885B2 (en, 2012) |
| DD (1) | DD209719A5 (en, 2012) |
| DE (3) | DE3222191A1 (en, 2012) |
| DK (1) | DK269083A (en, 2012) |
| EG (1) | EG16342A (en, 2012) |
| ES (1) | ES8403466A1 (en, 2012) |
| GR (1) | GR78616B (en, 2012) |
| HU (1) | HU189293B (en, 2012) |
| IE (1) | IE55403B1 (en, 2012) |
| IL (1) | IL68937A0 (en, 2012) |
| NZ (1) | NZ204500A (en, 2012) |
| PT (1) | PT76813B (en, 2012) |
| TR (1) | TR21499A (en, 2012) |
| ZA (1) | ZA834261B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA834100B (en) * | 1982-06-14 | 1984-02-29 | Ici Plc | Heterocyclic compounds |
| EP0097425B1 (en) * | 1982-06-14 | 1987-04-08 | Imperial Chemical Industries Plc | Fungicidal or plant growth regulating triazolyl ethanols |
| FR2606408B1 (fr) * | 1983-09-01 | 1989-11-24 | Sandoz Sa | Nouveau derive de l'ethanol, sa preparation et son utilisation comme fongicide |
| NL8402548A (nl) * | 1983-09-01 | 1985-04-01 | Sandoz Ag | Nieuwe azoolverbindingen. |
| DE3501245A1 (de) * | 1985-01-16 | 1986-07-17 | Bayer Ag | Azolyl-aroxymethyl-dimethylpentinole |
| GB8511344D0 (en) * | 1985-05-03 | 1985-06-12 | Ici Plc | Heterocyclic compounds |
| DE3628545A1 (de) * | 1985-09-23 | 1987-04-23 | Hoechst Ag | Arylmethylazole und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| GB8530429D0 (en) * | 1985-12-10 | 1986-01-22 | Ici Plc | Heterocyclic compounds |
| GB8620501D0 (en) * | 1986-08-22 | 1986-10-01 | Ici Plc | Heterocyclic compounds |
| JPH07116636B2 (ja) * | 1986-09-26 | 1995-12-13 | 川崎製鉄株式会社 | ラジアル型めつきセル |
| DE3707151A1 (de) * | 1987-03-06 | 1988-09-15 | Hoechst Ag | 1-(1-aryl-2-hydroxy-ethyl)-imidazole und deren salze, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| GB8816772D0 (en) * | 1988-07-14 | 1988-08-17 | Ici Plc | Heterocyclic compounds |
| JPH0572881U (ja) * | 1992-03-06 | 1993-10-05 | ミサワホーム株式会社 | 資材搬入装置 |
| JP2000053657A (ja) | 1998-08-12 | 2000-02-22 | Rikagaku Kenkyusho | ブラシノステロイド生合成阻害剤 |
| CN106632107A (zh) * | 2012-12-19 | 2017-05-10 | 巴斯夫欧洲公司 | 取代[1,2,4]三唑及其作为杀真菌剂的用途 |
| 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. |
| CN111777565B (zh) * | 2020-06-29 | 2022-03-18 | 江苏七洲绿色化工股份有限公司 | 一种氯唑酮的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4413003A (en) * | 1977-07-29 | 1983-11-01 | Rohm And Haas Company | β-Hydroxyarylethylimidazoles |
| DE2934507A1 (de) * | 1979-08-27 | 1981-04-02 | Basf Ag, 6700 Ludwigshafen | Triazolylether enthaltende mittel zur regulierung des pflanzenwachstums |
| US4414210A (en) * | 1979-10-02 | 1983-11-08 | Rohm And Haas Company | 2-Hydroxyarylethyltriazole fungicides |
| DE2951163A1 (de) * | 1979-12-19 | 1981-07-16 | Bayer Ag, 5090 Leverkusen | Substituierte triazolylmethyl-tert.-butyl-carbinole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte |
| DE3003933A1 (de) * | 1980-02-04 | 1981-08-13 | Basf Ag, 6700 Ludwigshafen | (beta) -imidazolylalkohole, verfahren zu ihrer herstellung, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit ihnen |
| DE3021551A1 (de) * | 1980-06-07 | 1981-12-24 | Bayer Ag, 5090 Leverkusen | 4-substituierte 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-one und -ole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
| DE3124580A1 (de) * | 1981-06-23 | 1983-01-05 | Bayer Ag, 5090 Leverkusen | Fungizide mittel |
| EP0097425B1 (en) * | 1982-06-14 | 1987-04-08 | Imperial Chemical Industries Plc | Fungicidal or plant growth regulating triazolyl ethanols |
| DE3242222A1 (de) * | 1982-11-15 | 1984-05-17 | Bayer Ag, 5090 Leverkusen | Hydroxyalkinyl-azolyl-derivate |
-
1982
- 1982-06-12 DE DE19823222191 patent/DE3222191A1/de not_active Withdrawn
-
1983
- 1983-05-27 US US06/498,606 patent/US4578396A/en not_active Expired - Fee Related
- 1983-05-30 AT AT86100632T patent/ATE45350T1/de not_active IP Right Cessation
- 1983-05-30 EP EP83105313A patent/EP0096786B1/de not_active Expired
- 1983-05-30 DE DE8383105313T patent/DE3373654D1/de not_active Expired
- 1983-05-30 DE DE8686100632T patent/DE3380350D1/de not_active Expired
- 1983-05-30 AT AT83105313T patent/ATE29719T1/de not_active IP Right Cessation
- 1983-05-30 EP EP86100632A patent/EP0192055B1/de not_active Expired
- 1983-06-03 PT PT76813A patent/PT76813B/pt unknown
- 1983-06-08 CS CS834128A patent/CS236885B2/cs unknown
- 1983-06-08 EG EG347/83A patent/EG16342A/xx active
- 1983-06-08 TR TR21499A patent/TR21499A/xx unknown
- 1983-06-09 DD DD83251863A patent/DD209719A5/de unknown
- 1983-06-09 IL IL68937A patent/IL68937A0/xx unknown
- 1983-06-09 NZ NZ204500A patent/NZ204500A/en unknown
- 1983-06-10 HU HU832073A patent/HU189293B/hu not_active IP Right Cessation
- 1983-06-10 IE IE1368/83A patent/IE55403B1/en unknown
- 1983-06-10 GR GR71621A patent/GR78616B/el unknown
- 1983-06-10 DK DK269083A patent/DK269083A/da not_active Application Discontinuation
- 1983-06-10 JP JP58103006A patent/JPS5921667A/ja active Granted
- 1983-06-10 ZA ZA834261A patent/ZA834261B/xx unknown
- 1983-06-10 BR BR8303091A patent/BR8303091A/pt not_active IP Right Cessation
- 1983-06-10 ES ES523165A patent/ES8403466A1/es not_active Expired
- 1983-06-14 AU AU15732/83A patent/AU567100B2/en not_active Ceased
-
1985
- 1985-10-04 US US06/784,405 patent/US4945101A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CS236885B2 (en) | 1985-05-15 |
| JPH0463068B2 (en, 2012) | 1992-10-08 |
| DE3380350D1 (en) | 1989-09-14 |
| PT76813B (en) | 1986-02-03 |
| EP0192055A3 (en) | 1986-09-03 |
| EP0096786A3 (en) | 1984-03-28 |
| US4945101A (en) | 1990-07-31 |
| TR21499A (tr) | 1984-07-18 |
| DD209719A5 (de) | 1984-05-23 |
| EP0192055A2 (de) | 1986-08-27 |
| EG16342A (en) | 1987-10-30 |
| DE3373654D1 (en) | 1987-10-22 |
| ES523165A0 (es) | 1984-03-16 |
| NZ204500A (en) | 1988-03-30 |
| HU189293B (en) | 1986-06-30 |
| ATE45350T1 (de) | 1989-08-15 |
| ZA834261B (en) | 1984-03-28 |
| DK269083D0 (da) | 1983-06-10 |
| EP0096786B1 (de) | 1987-09-16 |
| EP0192055B1 (de) | 1989-08-09 |
| GR78616B (en, 2012) | 1984-09-27 |
| EP0096786A2 (de) | 1983-12-28 |
| DK269083A (da) | 1983-12-13 |
| JPS5921667A (ja) | 1984-02-03 |
| ATE29719T1 (de) | 1987-10-15 |
| ES8403466A1 (es) | 1984-03-16 |
| US4578396A (en) | 1986-03-25 |
| IE831368L (en) | 1983-12-12 |
| AU567100B2 (en) | 1987-11-12 |
| IL68937A0 (en) | 1983-10-31 |
| PT76813A (en) | 1983-07-01 |
| BR8303091A (pt) | 1984-01-31 |
| AU1573283A (en) | 1983-12-15 |
| DE3222191A1 (de) | 1983-12-15 |
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