PE20171346A1 - Compuestos derivados acetilados de geranilorcinol. procedimiento de sintesis de obtencion de dichos compuestos y uso de dichos compuestos como antifungicos frente a botrytis cinerea - Google Patents
Compuestos derivados acetilados de geranilorcinol. procedimiento de sintesis de obtencion de dichos compuestos y uso de dichos compuestos como antifungicos frente a botrytis cinereaInfo
- Publication number
- PE20171346A1 PE20171346A1 PE2017001281A PE2017001281A PE20171346A1 PE 20171346 A1 PE20171346 A1 PE 20171346A1 PE 2017001281 A PE2017001281 A PE 2017001281A PE 2017001281 A PE2017001281 A PE 2017001281A PE 20171346 A1 PE20171346 A1 PE 20171346A1
- Authority
- PE
- Peru
- Prior art keywords
- compounds
- solution
- mmol
- botrytis cinerea
- synthesis procedure
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 241000123650 Botrytis cinerea Species 0.000 title abstract 2
- 230000000843 anti-fungal effect Effects 0.000 title abstract 2
- 229940121375 antifungal agent Drugs 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 abstract 3
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 abstract 1
- 239000005792 Geraniol Substances 0.000 abstract 1
- 239000007832 Na2SO4 Substances 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 150000007960 acetonitrile Chemical class 0.000 abstract 1
- 229940113087 geraniol Drugs 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- 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
- A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
-
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
- C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Insects & Arthropods (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Se refiere a un procedimiento de sintesis para obtener compuestos derivados acetilados de geranilorcinoles lineales, que comprende: preparar una solucion mezclando orcinol (1,22 g, 9,8 mmol), con geraniol (1,51 g, 9,8 mmol) y acetonitrilo (2mL); adicionar la solucion anterior en una solucion de acetonitrilo saturada en AgNO3 (2mL); agitar la solucion a temperatura ambiente bajo atmosfera de nitrogeno; inyectar lenta y directamente BF3Et2O (0,46 g, 3,2 mmol); agitar durante 48 horas; agregar hielo molido (aproximadamente 30 g) y abundante sal (NaCl); filtrar al vacio; extraer la fase organica con AcOEt (3 x 20 mL); lavar la fase organica con una solucion de NAHCO3 (15 mL, 5%) y agua (2 x 15 mL); secar sobre Na2SO4 anhidro y filtrar y evaporar a sequedad. Tambien se refiere a un compuesto de formula 2 y 4. Dicho compuesto es util como antifungico contra Botrytis cinerea
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CL2015000200A CL2015000200A1 (es) | 2015-01-27 | 2015-01-27 | Procedimiento de síntesis de compuestos derivados de geranil orcinol lineales; compuestos; y uso de dichos compuesto como antifúngico para tratar botrytis cinerea. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20171346A1 true PE20171346A1 (es) | 2017-09-13 |
Family
ID=56542090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2017001281A PE20171346A1 (es) | 2015-01-27 | 2016-01-25 | Compuestos derivados acetilados de geranilorcinol. procedimiento de sintesis de obtencion de dichos compuestos y uso de dichos compuestos como antifungicos frente a botrytis cinerea |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10524469B2 (es) |
| EP (1) | EP3251509A4 (es) |
| CL (1) | CL2015000200A1 (es) |
| PE (1) | PE20171346A1 (es) |
| WO (1) | WO2016119074A1 (es) |
| ZA (1) | ZA201705804B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CL2015001918A1 (es) * | 2015-07-06 | 2016-04-22 | Univ Técnica Federico Santa María | Composición pesticida de sustancias de origen natural que comprende dos compuestos acetilados de compuestos prenilados de hidroquinona y de orcinol; los compuestos acetilados, procedimientos de preparación y usos como fungicidas en el control del hongo fitopatógeno botrytis cinerea. |
| CN112379711B (zh) * | 2020-11-12 | 2021-09-03 | 浙江宜葆生物科技有限公司 | 一种基于物联网的草莓灰霉病预报系统 |
| CN115251052A (zh) * | 2021-04-30 | 2022-11-01 | 迈图高新材料公司 | 基于精油的农业组合物及使用其防控害虫的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040005351A1 (en) * | 2002-03-29 | 2004-01-08 | Kwon Glen S. | Polymeric micelle formulations of hydrophobic compounds and methods |
-
2015
- 2015-01-27 CL CL2015000200A patent/CL2015000200A1/es unknown
-
2016
- 2016-01-25 US US15/546,910 patent/US10524469B2/en active Active
- 2016-01-25 WO PCT/CL2016/050004 patent/WO2016119074A1/es not_active Ceased
- 2016-01-25 PE PE2017001281A patent/PE20171346A1/es unknown
- 2016-01-25 EP EP16742628.7A patent/EP3251509A4/en not_active Withdrawn
-
2017
- 2017-08-25 ZA ZA2017/05804A patent/ZA201705804B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016119074A1 (es) | 2016-08-04 |
| CL2015000200A1 (es) | 2015-06-26 |
| EP3251509A1 (en) | 2017-12-06 |
| EP3251509A4 (en) | 2018-06-27 |
| ZA201705804B (en) | 2022-03-30 |
| US10524469B2 (en) | 2020-01-07 |
| US20180035669A1 (en) | 2018-02-08 |
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