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FENPYRITHRIN

FENPYRITHRIN structure

FENPYRITHRIN 

structure
  • CAS No:

    68523-18-2

  • Formula:

    C21H18Cl2N2O3

  • Chemical Name:

    FENPYRITHRIN

  • Synonyms:

    DC 417;Dowco 417;Vivithrin;FENPYRITHRIN;(R,S)-α-cyano-(6-phenoxy-2-pyridinyl) methyl (R,S)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethyl cyclopropanecarboxylate;cyano(6-phenoxypyridin-2-yl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(6-phenoxy-2-pyridinyl)methyl ester

  • Categories:

    Agrochemicals  >  Insecticides

FENPYRITHRIN Basic Attributes

417.29

417.29

X6EI42CYQ5

DTXSID3058161

Characteristics

72.2

5.4

FENPYRITHRIN Use and Manufacturing

Methods of Manufacturing

Preparation method 1: Preparation of 6-phenoxypyridinecarbaldehyde cyanohydrin Add a mixture of 0.61mol 6-phenoxypyridinecarbaldehyde and 0.73mol sodium bisulfite to 750mL water, stir to dissolve, and extract with dichloromethane to remove water-insoluble substances , Then add 0.73 mol of sodium bisulfate mixture, react for 2h, and then extract with dichloromethane. The extract is washed with sodium bisulfite aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a yellow solid. Alkane, stirring, and drying to obtain 6-phenoxypyridinecarbaldehyde cyanohydrin, melting point 84.5 ℃. Synthesis of cypermethrin 0.112mol of phenoxypyridinecarbaldehyde cyanohydrin and 0.123mol of dipermethrin (cis:trans=4:6), add to 300mL of anhydrous ether, cool to 0℃ in an ice bath, and slowly add 25mL Triethylamine, stirred and reacted for 2h, warmed to room temperature at the same time, diluted with water, stood still, separated, washed with water, acid washed, alkali washed, dried, concentrated, and collected 125℃/6.65Pa fraction under reduced pressure to obtain a yellow oil, namely Crude cypermethrin. Preparation method Cypermethrin can also be synthesized by using dipermethrin, 6-phenoxypyridinecarbaldehyde and sodium cyanide in the presence of a phase transfer catalyst.

Uses

The product has stomach toxicity and contact killing effect, is a broad-spectrum insecticide, and has a good effect in controlling cotton bollworm, cotton bollworm, small leaf moth and cotton whitefly.

Production

Fenpirithrin was manufactured using the same multi step ester assembly strategy typical of synthetic pyrethroids. Its production centred on preparing two key fragments. Firstly, a cyclopropanecarboxylic acid derivative bearing the characteristic 2,2 dichlorovinyl and 2,2 dimethyl substituents, and secondly a cyano(6 phenoxy 2 pyridyl)methyl alcohol, produced through pyridyl phenoxy coupling and cyanohydrin formation. These intermediates were then esterified to form technical grade fenpirithrin, which was purified and formulated

Computed Properties

Molecular Weight:417.3
XLogP3:5.4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:416.0694478
Monoisotopic Mass:416.0694478
Topological Polar Surface Area:72.2
Heavy Atom Count:28
Complexity:647
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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