AU570254B2 - Substituted diazolylalkyl - carbinols and their use as fungicidal agents - Google Patents
Substituted diazolylalkyl - carbinols and their use as fungicidal agentsInfo
- Publication number
- AU570254B2 AU570254B2 AU30571/84A AU3057184A AU570254B2 AU 570254 B2 AU570254 B2 AU 570254B2 AU 30571/84 A AU30571/84 A AU 30571/84A AU 3057184 A AU3057184 A AU 3057184A AU 570254 B2 AU570254 B2 AU 570254B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- phenyl
- benzyl
- chlorine
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000000417 fungicide Substances 0.000 title 1
- -1 methylallyl Chemical group 0.000 abstract 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 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 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 239000002253 acid Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 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 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 239000002184 metal Chemical class 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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
- A01N43/48—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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (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)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1. Use of substituted diazolyalkyl carbinols of the formula see diagramm : EP0131845,P16,F1 in which A represents a nitrogen atom or the CH group ; B represents a nitrogen atom or the CH group ; X represents hydrogen and straight-chain or branched alkyl with 1 to 4 carbon atoms ; Y represents straight-chain or branched alkyl with 1 to 4 carbon atoms ; and, if X represents hydrogen, also represents allyl, methylallyl, propargyl, methylpropargyl or benzyl which is optionally substituted in the phenyl part by flourine, chlorine, bromine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, triflouoromethyl, trifluoromethoxy, triflouromethylthio, nitro and cyano ; R represents phenyl which is mono- or disubstituted by identical or different substituents from the group comprising methylthio, triflouromethoxy, trifluoromethylthio, nitro, cyano, hydroxyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, 1-hydroximinoethyl, methoximinomethyl and 1-methoximinoethyl, and also comprising phenyl, phenoxy, benzyl or benzyloxy, each of which is optionally substituted by flourine, chlorine or methyl, and R furthermore represents the grouping see diagramm : EP0131845,P16,F2 wherein Alk**1 represents methyl or ethyl, Alak**2 represents methyl or ethyl ; Alk**1 and Alk**2 , together with the carbon atom to which they are bonded, represent cyclobutyl, cyclopentyl or cyclohexyl ; and R**1 represents methyl, ethyl, n-propyl, i-propyl, n-butyl, neopentyl, and phenyl, benzyl, phenethyl, phenoxy, phenylthio, pnenoxymethyl, phenoxyethyl, phenylthiomethyl, phenylthioethyl, benzyloxy or benzylthio, it being possible for each of the eleven aforementioned radicals to be substituted in the phenyl part by fluorine, chlorine, bromine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, nitro, cyano, hydroxyl, hydroxycarbonyl, hydroximinomethyl, 1-hydroximinoethyl, methoximinomethyl or 1-methoximinoethyl, and by phenyl, phenoxy, benzyl and/or benzyloxy, each of which is optionally substituted by fluorine, chlorine or methyl, and acid addition salts and metal salt complexes thereof for combating fungi in plant protection.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3325313 | 1983-07-13 | ||
| DE19833325313 DE3325313A1 (en) | 1983-07-13 | 1983-07-13 | FUNGICIDES, THEIR PRODUCTION AND USE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3057184A AU3057184A (en) | 1985-01-17 |
| AU570254B2 true AU570254B2 (en) | 1988-03-10 |
Family
ID=6203904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU30571/84A Ceased AU570254B2 (en) | 1983-07-13 | 1984-07-13 | Substituted diazolylalkyl - carbinols and their use as fungicidal agents |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0131845B1 (en) |
| JP (1) | JPS6038304A (en) |
| AT (1) | ATE29196T1 (en) |
| AU (1) | AU570254B2 (en) |
| BR (1) | BR8403499A (en) |
| DE (2) | DE3325313A1 (en) |
| DK (1) | DK343084A (en) |
| GR (1) | GR81505B (en) |
| HU (1) | HU195078B (en) |
| IL (1) | IL72365A0 (en) |
| NZ (1) | NZ208847A (en) |
| PH (1) | PH21345A (en) |
| PT (1) | PT78841B (en) |
| ZA (1) | ZA845389B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU653082B2 (en) * | 1991-11-25 | 1994-09-15 | Takeda Chemical Industries Ltd. | Optically active azole compounds their production and use |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK159205C (en) * | 1983-03-16 | 1991-03-04 | Pfizer | BIS (TRIAZOL) ALKANOL COMPOUNDS, APPLICATION OF THESE, PHARMACEUTICAL PREPARATIONS AND AGRICULTURAL FUNGICIDS CONTAINING THESE AND PROCEDURES FOR TREATING PLANTS OR SEEDS WHICH HAVE A FUNGI INFECTION |
| DE3730871A1 (en) * | 1987-09-15 | 1989-03-23 | Bayer Ag | BISAZOLYL HYDROXYALKYL DERIVATIVES |
| DE3732384A1 (en) * | 1987-09-25 | 1989-04-06 | Bayer Ag | BISAZOLYL-HYDROXYALKYL DERIVATIVES CONTAINING ANTIMYCOTIC AGENTS |
| DE3803833A1 (en) * | 1988-02-09 | 1989-08-17 | Bayer Ag | SUBSTITUTED AZOLYL METHYLOXIRANES |
| 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 |
| NZ270418A (en) * | 1994-02-07 | 1997-09-22 | Eisai Co Ltd | Polycyclic triazole & imidazole derivatives, antifungal compositions |
| US6297239B1 (en) | 1997-10-08 | 2001-10-02 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| EP2746275A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
| WO2014095555A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
| EP2746276A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
| WO2014184309A1 (en) * | 2013-05-17 | 2014-11-20 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2506384A (en) * | 1983-03-02 | 1984-09-06 | Bayer Aktiengesellschaft | Substituted diazolylalkyl-carbinols |
| AU2507684A (en) * | 1983-03-08 | 1984-09-13 | Imperial Chemical Industries Plc | Azolyl-propanol derivatives |
| AU2563684A (en) * | 1983-03-16 | 1984-09-20 | Pfizer Corp. | Bis-1,2,4-triazole antifungal derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| GB2099818A (en) * | 1981-06-06 | 1982-12-15 | Pfizer Ltd | Triazoles |
-
1983
- 1983-07-13 DE DE19833325313 patent/DE3325313A1/en not_active Withdrawn
-
1984
- 1984-07-03 PT PT78841A patent/PT78841B/en unknown
- 1984-07-04 AT AT84107728T patent/ATE29196T1/en active
- 1984-07-04 DE DE8484107728T patent/DE3465687D1/en not_active Expired
- 1984-07-04 EP EP84107728A patent/EP0131845B1/en not_active Expired
- 1984-07-10 NZ NZ208847A patent/NZ208847A/en unknown
- 1984-07-10 IL IL72365A patent/IL72365A0/en unknown
- 1984-07-11 GR GR75279A patent/GR81505B/el unknown
- 1984-07-11 JP JP59142486A patent/JPS6038304A/en active Pending
- 1984-07-11 PH PH30969A patent/PH21345A/en unknown
- 1984-07-12 HU HU872728A patent/HU195078B/en unknown
- 1984-07-12 BR BR8403499A patent/BR8403499A/en unknown
- 1984-07-12 DK DK343084A patent/DK343084A/en not_active Application Discontinuation
- 1984-07-12 ZA ZA845389A patent/ZA845389B/en unknown
- 1984-07-13 AU AU30571/84A patent/AU570254B2/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2506384A (en) * | 1983-03-02 | 1984-09-06 | Bayer Aktiengesellschaft | Substituted diazolylalkyl-carbinols |
| AU2507684A (en) * | 1983-03-08 | 1984-09-13 | Imperial Chemical Industries Plc | Azolyl-propanol derivatives |
| AU2563684A (en) * | 1983-03-16 | 1984-09-20 | Pfizer Corp. | Bis-1,2,4-triazole antifungal derivatives |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU653082B2 (en) * | 1991-11-25 | 1994-09-15 | Takeda Chemical Industries Ltd. | Optically active azole compounds their production and use |
Also Published As
| Publication number | Publication date |
|---|---|
| DK343084D0 (en) | 1984-07-12 |
| HU195078B (en) | 1988-04-28 |
| JPS6038304A (en) | 1985-02-27 |
| DE3465687D1 (en) | 1987-10-08 |
| BR8403499A (en) | 1985-06-25 |
| IL72365A0 (en) | 1984-11-30 |
| AU3057184A (en) | 1985-01-17 |
| GR81505B (en) | 1984-12-11 |
| NZ208847A (en) | 1986-10-08 |
| PT78841B (en) | 1986-06-02 |
| PT78841A (en) | 1984-08-01 |
| DE3325313A1 (en) | 1985-01-31 |
| EP0131845A2 (en) | 1985-01-23 |
| ZA845389B (en) | 1985-03-27 |
| ATE29196T1 (en) | 1987-09-15 |
| DK343084A (en) | 1985-01-14 |
| EP0131845A3 (en) | 1985-03-06 |
| EP0131845B1 (en) | 1987-09-02 |
| PH21345A (en) | 1987-10-13 |
| HUT34319A (en) | 1985-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU570254B2 (en) | Substituted diazolylalkyl - carbinols and their use as fungicidal agents | |
| ES8606299A1 (en) | Substituted triazoles, processes for making them, their use as fungicides and fungicidal compositions containing them. | |
| IE811093L (en) | Triazoles. | |
| ES473093A1 (en) | 1-Phenyl-2-azolyl-4,4-dimethyl-1-penten-3-ols and the fungicidal use thereof | |
| CA2320304A1 (en) | Fungicidal 7-alkyl-triazolopyrimidines | |
| PH23038A (en) | Benzoylurea derivatives having anti-tumor activity | |
| DK83684D0 (en) | SUBSTITUTED DIAZOLYLALKYL CARBINOLS, THEIR PREPARATION AND USE AS ANTIMYCOTIC AGENTS | |
| EP0094167A3 (en) | Azolyl fungicide and plant growth regulators and compositions containing them | |
| EP0061840A3 (en) | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them | |
| AU549461B2 (en) | (1,2,4 triazol-l-yl)/(1,3-diazol-l-yl) thioethers | |
| EP0258030A3 (en) | A fungicidal composition containing an iodopropargyl carbamate | |
| IE830508L (en) | Triazoles; fungicidal compositions | |
| RU93053026A (en) | N-ACETONILBENZAMIDES AND THEIR USE AS FUNGICIDES |