FR2453140A1 - Insecticide and acaricide-phenoxy-benzyl pyrethroid ester prodn. - by reaction of acid chloride with 3-phenoxy-benzaldehyde and alkali cyanide in two=phase system in presence of a phase-transfer catalyst - Google Patents
Insecticide and acaricide-phenoxy-benzyl pyrethroid ester prodn. - by reaction of acid chloride with 3-phenoxy-benzaldehyde and alkali cyanide in two=phase system in presence of a phase-transfer catalystInfo
- Publication number
- FR2453140A1 FR2453140A1 FR8007522A FR8007522A FR2453140A1 FR 2453140 A1 FR2453140 A1 FR 2453140A1 FR 8007522 A FR8007522 A FR 8007522A FR 8007522 A FR8007522 A FR 8007522A FR 2453140 A1 FR2453140 A1 FR 2453140A1
- Authority
- FR
- France
- Prior art keywords
- phenoxy
- phase
- formula
- prodn
- acid chloride
- 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.)
- Pending
Links
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 239000002917 insecticide Substances 0.000 title abstract 2
- 239000003444 phase transfer catalyst Substances 0.000 title abstract 2
- 239000002728 pyrethroid Substances 0.000 title abstract 2
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 title 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title 1
- 239000003513 alkali Substances 0.000 title 1
- 241000238876 Acari Species 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000000642 acaricide Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal cyanide Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000003983 crown ethers Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000004714 phosphonium salts Chemical class 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
For the prodn. of gamma-cyano-3-phenoxybenzyl esters of formula (I), an acid chloride of formula R-CO-Cl (II) is reacted with an equimolar amt or a slight excess of an aldehyde of formula (III) and an equimolar amt or an excess of alkali metal cyanide in the presence of a 2-phase mixt of an insert organic solvent and water and in the presence of 0.1-10 mol% of a phase-transfer catalyst consisting of an organic ammonium salt, an organic phosphonium salt or a crown ether at 20-50 degrees C for the time sufficient for substantially complete reaction. In (I), R is a residue of formula (Ia) or (Ib). (I) are known pyrethroid insecticides and acaricides. They can be used in plant protection, and can also be used against ectropanasites or domesticalted warm-blooded animals. Suprisingly, (I) may be administered orally or parenterally to afford protection against ectoparasitic ticks or insects.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000324757A CA1142953A (en) | 1979-04-03 | 1979-04-03 | Process for the preparation of pesticidal esters of certain carboxylic acids using phase transfer catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2453140A1 true FR2453140A1 (en) | 1980-10-31 |
Family
ID=4113909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8007522A Pending FR2453140A1 (en) | 1979-04-03 | 1980-04-03 | Insecticide and acaricide-phenoxy-benzyl pyrethroid ester prodn. - by reaction of acid chloride with 3-phenoxy-benzaldehyde and alkali cyanide in two=phase system in presence of a phase-transfer catalyst |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS55133349A (en) |
| BR (1) | BR8001910A (en) |
| CA (1) | CA1142953A (en) |
| DE (1) | DE3012918A1 (en) |
| DK (1) | DK144580A (en) |
| ES (1) | ES8104793A1 (en) |
| FR (1) | FR2453140A1 (en) |
| IT (1) | IT1127364B (en) |
| SE (1) | SE8002551L (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE76059T1 (en) * | 1987-02-13 | 1992-05-15 | Lucky Ltd | PROCESSES FOR PREPARING PYRETHROID-TYPE ESTERS COMPOUNDS. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2342960A1 (en) * | 1976-03-01 | 1977-09-30 | Shell Int Research | PREPARATION OF BENZYL ESTERS PESTICIDES |
| EP0000345A1 (en) * | 1977-07-06 | 1979-01-24 | Bayer Ag | Substituted phenoxybenzyloxycarbonyl derivatives, their preparation and their use as insecticides and acaricides |
| EP0036774A1 (en) * | 1980-03-24 | 1981-09-30 | Sumitomo Chemical Company, Limited | Preparation of insecticidal optically active alpha-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates |
-
1979
- 1979-04-03 CA CA000324757A patent/CA1142953A/en not_active Expired
-
1980
- 1980-02-27 IT IT48019/80A patent/IT1127364B/en active
- 1980-03-19 JP JP3419980A patent/JPS55133349A/en active Pending
- 1980-03-28 BR BR8001910A patent/BR8001910A/en unknown
- 1980-04-01 ES ES490185A patent/ES8104793A1/en not_active Expired
- 1980-04-02 DE DE19803012918 patent/DE3012918A1/en not_active Withdrawn
- 1980-04-02 SE SE8002551A patent/SE8002551L/en not_active Application Discontinuation
- 1980-04-02 DK DK144580A patent/DK144580A/en not_active Application Discontinuation
- 1980-04-03 FR FR8007522A patent/FR2453140A1/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2342960A1 (en) * | 1976-03-01 | 1977-09-30 | Shell Int Research | PREPARATION OF BENZYL ESTERS PESTICIDES |
| EP0000345A1 (en) * | 1977-07-06 | 1979-01-24 | Bayer Ag | Substituted phenoxybenzyloxycarbonyl derivatives, their preparation and their use as insecticides and acaricides |
| EP0036774A1 (en) * | 1980-03-24 | 1981-09-30 | Sumitomo Chemical Company, Limited | Preparation of insecticidal optically active alpha-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates |
Also Published As
| Publication number | Publication date |
|---|---|
| DK144580A (en) | 1980-10-04 |
| ES490185A0 (en) | 1981-05-16 |
| ES8104793A1 (en) | 1981-05-16 |
| CA1142953A (en) | 1983-03-15 |
| BR8001910A (en) | 1980-11-25 |
| IT1127364B (en) | 1986-05-21 |
| SE8002551L (en) | 1980-10-04 |
| DE3012918A1 (en) | 1980-10-23 |
| JPS55133349A (en) | 1980-10-17 |
| IT8048019A0 (en) | 1980-02-27 |
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