DK171542B1 - Azolderivater, fremgangsmåde til deres fremstilling, oxiran-, cyklopentanon- og cyklopentancarboxylsyrederivater til fremstilling deraf og landbrugs- og havebrugsmidler indeholdende disse azolderivater - Google Patents
Azolderivater, fremgangsmåde til deres fremstilling, oxiran-, cyklopentanon- og cyklopentancarboxylsyrederivater til fremstilling deraf og landbrugs- og havebrugsmidler indeholdende disse azolderivater Download PDFInfo
- Publication number
- DK171542B1 DK171542B1 DK588687A DK588687A DK171542B1 DK 171542 B1 DK171542 B1 DK 171542B1 DK 588687 A DK588687 A DK 588687A DK 588687 A DK588687 A DK 588687A DK 171542 B1 DK171542 B1 DK 171542B1
- Authority
- DK
- Denmark
- Prior art keywords
- hydrogen atom
- derivative
- alkyl group
- formula
- atom
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- 238000002360 preparation method Methods 0.000 title claims description 30
- 239000003795 chemical substances by application Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title claims description 7
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 title claims description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 title description 13
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 9
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 title description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
- -1 benzyl halide Chemical class 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical class O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 claims description 18
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
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- 238000006243 chemical reaction Methods 0.000 claims description 15
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 238000006114 decarboxylation reaction Methods 0.000 claims description 6
- FXBPINRBSNMESY-UHFFFAOYSA-N 2-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1=O FXBPINRBSNMESY-UHFFFAOYSA-N 0.000 claims description 4
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- NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical class C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
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- 239000001257 hydrogen Substances 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 241000123650 Botrytis cinerea Species 0.000 description 4
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Classifications
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- 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
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
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- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/673—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 isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—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 isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- 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
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- 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
-
- 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
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- 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)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26555986 | 1986-11-10 | ||
| JP26555986 | 1986-11-10 | ||
| JP16112687 | 1987-06-30 | ||
| JP16112687 | 1987-06-30 | ||
| JP62271277A JPH0625140B2 (ja) | 1986-11-10 | 1987-10-27 | 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤 |
| JP27127787 | 1987-10-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK588687D0 DK588687D0 (da) | 1987-11-10 |
| DK588687A DK588687A (da) | 1988-05-11 |
| DK171542B1 true DK171542B1 (da) | 1996-12-30 |
Family
ID=27321802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK588687A DK171542B1 (da) | 1986-11-10 | 1987-11-10 | Azolderivater, fremgangsmåde til deres fremstilling, oxiran-, cyklopentanon- og cyklopentancarboxylsyrederivater til fremstilling deraf og landbrugs- og havebrugsmidler indeholdende disse azolderivater |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US4938792A (pt) |
| EP (1) | EP0267778B1 (pt) |
| JP (1) | JPH0625140B2 (pt) |
| AU (1) | AU584530B2 (pt) |
| BR (1) | BR8706104A (pt) |
| CA (1) | CA1331006C (pt) |
| DE (1) | DE3784999T2 (pt) |
| DK (1) | DK171542B1 (pt) |
| ES (1) | ES2053564T3 (pt) |
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| JPH0819108B2 (ja) * | 1986-12-22 | 1996-02-28 | 呉羽化学工業株式会社 | 新規アゾ−ル誘導体、その製造法及び該誘導体を活性成分として含有する農園芸用殺菌剤 |
| JPH0696530B2 (ja) * | 1987-06-05 | 1994-11-30 | 呉羽化学工業株式会社 | アゾール抗真菌剤 |
| US5240955A (en) * | 1987-06-05 | 1993-08-31 | Kureha Kagaku Kogyo Kabushiki Kaisha | Azole derivative and azole mycocide |
| JPH0739396B2 (ja) * | 1988-01-14 | 1995-05-01 | 呉羽化学工業株式会社 | 新規アゾール置換シクロアルカノール誘導体、その製造法及び該誘導体の農園芸用殺菌剤としての利用 |
| JPH0762001B2 (ja) * | 1988-02-16 | 1995-07-05 | 呉羽化学工業株式会社 | アゾリルメチルシクロアルカノール誘導体の製造法 |
| US5292764A (en) * | 1988-05-10 | 1994-03-08 | Kureha Kagaku Kogyo K.K. | Azole derivatives for protecting industrial materials from bacteria |
| GB8820603D0 (en) * | 1988-08-31 | 1988-09-28 | Shell Int Research | Cyclopentane derivatives |
| GB2225006B (en) * | 1988-08-31 | 1992-02-12 | Shell Int Research | Process for the preparation of cyclopentane derivatives |
| CA1339611C (en) * | 1988-08-31 | 1997-12-30 | Paul Howard Briner | Cyclopentane derivatives |
| US5262543A (en) * | 1988-08-31 | 1993-11-16 | Kureha Kagaku Kogyu Kabushiki Kaisha | Process for the preparation of cyclopentane derivatives |
| CA2006309C (fr) * | 1988-12-29 | 2001-12-18 | Jean Hutt | Azolylmethylcyclopentane benzylidene fongicide |
| FR2649700B2 (fr) * | 1988-12-29 | 1994-10-14 | Rhone Poulenc Agrochimie | Azolylmethylcyclopentane benzilidene et utilisation comme fongicide |
| US5256683A (en) * | 1988-12-29 | 1993-10-26 | Rhone-Poulenc Agrochimie | Fungicidal compositions containing (benzylidene)-azolylmethylcycloalkane |
| FR2641277B1 (fr) * | 1988-12-29 | 1994-08-26 | Rhone Poulenc Agrochimie | Azolylmethylcyclopentane ou cyclopentene benzolidene et utilisation comme fongicide |
| FR2649101B1 (fr) * | 1989-06-30 | 1994-10-28 | Rhone Poulenc Agrochimie | Azolylmethylcyclohexane benzilidene et utilisation comme fongicide |
| JP2637824B2 (ja) * | 1989-08-15 | 1997-08-06 | 呉羽化学工業株式会社 | 新規アゾール置換シクロアルカノール誘導体、その製造法及び該誘導体の農園芸用殺菌剤 |
| US5264450A (en) * | 1989-08-15 | 1993-11-23 | Kureha Kagaku Kogyo Kabushiki Kaisha | Imidazole substituted cycloalkanol derivatives and fungicidal compositions containing same |
| JPH03197464A (ja) * | 1989-12-16 | 1991-08-28 | Basf Ag | 置換アゾリルメチルシクロアルカノール及びこれを含有する殺菌剤 |
| FR2662911B1 (fr) * | 1990-06-12 | 1996-12-13 | Rhone Poulenc Agrochimie | Procede pour proteger les produits de multiplication des vegetaux et les vegetaux en resultant au moyen d'un triazolyl cyclopentanol. |
| FR2663196A1 (fr) * | 1990-06-13 | 1991-12-20 | Rhone Poulenc Agrochimie | Composition fongicide a base d'un triazole et d'une autre matiere active pour le traitement des semences. |
| FR2663195A1 (fr) * | 1990-06-13 | 1991-12-20 | Rhone Poulenc Agrochimie | Procede de traitement fongicide foliaire au moyen d'un triazole et composition fongicide pour mettre en óoeuvre le procede. |
| US5200535A (en) * | 1990-09-03 | 1993-04-06 | Shell Research Limited | Cyclohexanone derivatives |
| GB9019191D0 (en) * | 1990-09-03 | 1990-10-17 | Shell Int Research | Cyclopentanol derivatives |
| TW221288B (pt) * | 1990-09-03 | 1994-02-21 | Shell Int Research | |
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| JP2938223B2 (ja) * | 1991-06-07 | 1999-08-23 | 呉羽化学工業株式会社 | 切花の鮮度保持剤及び鮮度保持方法 |
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| FR2704388B1 (fr) * | 1993-04-27 | 1995-06-09 | Rhone Poulenc Agrochimie | Procede pour ameliorer la vigueur et ou la sante des vegetaux tels que les cereales par action d'un derive de type triazole. |
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| JPH07138160A (ja) * | 1993-11-18 | 1995-05-30 | Kureha Chem Ind Co Ltd | アゾール誘導体を含有する抗アロマターゼ剤 |
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| DE4425948A1 (de) * | 1994-07-21 | 1996-01-25 | Bayer Ag | Azolylmethyl-substituierte Cycloalkanole oder Mikrobzide |
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| JPWO2014057844A1 (ja) | 2012-10-11 | 2016-09-05 | 株式会社クレハ | シクロアルカノール誘導体の製造方法およびアゾール誘導体の製造方法 |
| US20150257383A1 (en) | 2012-10-12 | 2015-09-17 | Basf Se | Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
| CN104684881A (zh) * | 2012-11-27 | 2015-06-03 | 株式会社吴羽 | 羰基化合物的制备方法 |
| EP2746256A1 (en) * | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
| WO2014095249A1 (en) * | 2012-12-19 | 2014-06-26 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
| US10759767B2 (en) | 2012-12-20 | 2020-09-01 | BASF Agro B.V. | Compositions comprising a triazole compound |
| EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
| CN105308051A (zh) * | 2013-07-03 | 2016-02-03 | 株式会社吴羽 | 环氧乙烷衍生物的制备方法及唑衍生物的制备方法 |
| EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| EP3046915A1 (en) | 2013-09-16 | 2016-07-27 | Basf Se | Fungicidal pyrimidine compounds |
| EA201690802A1 (ru) | 2013-12-05 | 2016-08-31 | Куреха Корпорейшн | Сельскохозяйственное или садоводческое химическое средство, способ борьбы с болезнями растений и продукт для борьбы с болезнями растений |
| CA2931346A1 (en) | 2013-12-05 | 2015-06-11 | Kureha Corporation | Fungicide comprising an azole derivative and a compound having a ubiquinol reductase inhibitory capacity |
| UA114458C2 (uk) | 2013-12-05 | 2017-06-12 | Куреха Корпорейшн | Сільськогосподарський або садівничий хімікат, спосіб боротьби із захворюваннями рослин і продукт для боротьби із захворюваннями рослин |
| EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
| US10899932B2 (en) | 2014-10-24 | 2021-01-26 | Basf Se | Non-amphoteric, quaternisable and water-soluble polymers for modifying the surface charge of solid particles |
| WO2017001252A1 (en) | 2015-07-02 | 2017-01-05 | BASF Agro B.V. | Pesticidal compositions comprising a triazole compound |
| WO2017171095A1 (ja) * | 2016-04-01 | 2017-10-05 | 株式会社クレハ | アゾール誘導体の製造方法およびその中間体化合物 |
| CN114773279B (zh) * | 2022-04-13 | 2023-12-05 | 浙江工业大学 | 一种叶菌唑的新合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137731A (en) * | 1962-01-26 | 1964-06-16 | Givaudan Corp | Process for preparing substituted cyclopentenones |
| US3859357A (en) * | 1969-07-10 | 1975-01-07 | Nat Res Dev | Insecticides |
| US4654332A (en) * | 1979-03-07 | 1987-03-31 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| 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 |
| AU542623B2 (en) | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| EP0052425A3 (en) | 1980-11-13 | 1982-08-11 | Imperial Chemical Industries Plc | Triazole and imidazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| EP0052424B2 (en) | 1980-11-19 | 1990-02-28 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| ZA817473B (en) | 1980-11-19 | 1982-10-27 | Ici Plc | Triazole and imidazole compounds |
| DE3369131D1 (en) | 1982-04-22 | 1987-02-19 | Ici Plc | Antifungal azolyl phenyl substituted alicyclic alcohols |
| GB8405368D0 (en) * | 1984-03-01 | 1984-04-04 | Ici Plc | Heterocyclic compounds |
| JPS62149667A (ja) * | 1985-09-12 | 1987-07-03 | Kureha Chem Ind Co Ltd | 新規なアゾール誘導体、その製造法及び該誘導体を含有する農園芸用薬剤 |
| US4863505A (en) | 1985-09-12 | 1989-09-05 | Kureha Kagaku Kogyo Kabushiki Kaisha | Novel derivative of azole, and agricultural and horticultural composition containing the same as an active incredient |
-
1987
- 1987-10-27 JP JP62271277A patent/JPH0625140B2/ja not_active Expired - Fee Related
- 1987-10-30 US US07/115,084 patent/US4938792A/en not_active Expired - Lifetime
- 1987-11-06 CA CA000551296A patent/CA1331006C/en not_active Expired - Lifetime
- 1987-11-10 DK DK588687A patent/DK171542B1/da not_active IP Right Cessation
- 1987-11-10 DE DE8787309925T patent/DE3784999T2/de not_active Expired - Lifetime
- 1987-11-10 ES ES87309925T patent/ES2053564T3/es not_active Expired - Lifetime
- 1987-11-10 AU AU80961/87A patent/AU584530B2/en not_active Expired
- 1987-11-10 EP EP87309925A patent/EP0267778B1/en not_active Expired - Lifetime
- 1987-11-10 BR BR8706104A patent/BR8706104A/pt not_active IP Right Cessation
-
1990
- 1990-04-24 US US07/514,170 patent/US5028254A/en not_active Expired - Lifetime
-
1991
- 1991-04-25 US US07/691,406 patent/US5159118A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0267778A3 (en) | 1989-04-19 |
| US5159118A (en) | 1992-10-27 |
| DK588687A (da) | 1988-05-11 |
| JPH0193574A (ja) | 1989-04-12 |
| DK588687D0 (da) | 1987-11-10 |
| US5028254A (en) | 1991-07-02 |
| EP0267778A2 (en) | 1988-05-18 |
| AU8096187A (en) | 1988-05-19 |
| EP0267778B1 (en) | 1993-03-24 |
| CA1331006C (en) | 1994-07-26 |
| DE3784999T2 (de) | 1993-07-01 |
| DE3784999D1 (pt) | 1993-04-29 |
| JPH0625140B2 (ja) | 1994-04-06 |
| US4938792A (en) | 1990-07-03 |
| BR8706104A (pt) | 1988-06-14 |
| AU584530B2 (en) | 1989-05-25 |
| ES2053564T3 (es) | 1994-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |