Pyriproxyfen

Base Information

• Chemical Name: Pyriproxyfen
• CAS No.: 95737-68-1
• Deprecated CAS: 126040-81-1,133695-78-0,133695-78-0
• Molecular Formula: C20H19NO3
• Molecular Weight: 321.376
• European Community (EC) Number: 429-800-1,619-166-6
• ICSC Number: 1269
• UN Number: 3077
• UNII: 3Q9VOR705O
• DSSTox Substance ID: DTXSID1032640
• Nikkaji Number: J227.495G
• Wikipedia: Pyriproxyfen
• Wikidata: Q413089
• Metabolomics Workbench ID: 56210
• ChEMBL ID: CHEMBL1883234
• Mol file: 95737-68-1.mol

Synonyms:(+--)-pyriproxyfen;2-(1-methyl-2-(4-phenoxyphenoxy)ethoxy)pyridine;4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether;juvinal;pyridine, 2-(1-methyl-2-(4-phenoxyphenoxy)ethoxy)-;pyriproxyfen;pyriproxyfen, (+--)-;pyriproxyfen, (R)-isomer;pyriproxyfen, (S)-isomer;S 31183;S-31183

Chemical Property of Pyriproxyfen

Chemical Property:

• Appearance/Colour: White to pale yellow crystalline powder
• Vapor Pressure: 2.83E-08mmHg at 25°C
• Melting Point: 45-47 °C
• Refractive Index: 1.58
• Boiling Point: 462 °C at 760 mmHg
• PKA: 3.2 (base, est.)
• Flash Point: 165.4 °C
• PSA: 40.58000
• Density: 1.151 g/cm³
• LogP: 4.72020
• Storage Temp.: 0-6°C
• Water Solubility.: 0.4 mg l-1 (25 °C)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 321.13649347
• Heavy Atom Count: 24
• Complexity: 338

Purity/Quality:

98% ^*data from raw suppliers

Pyriproxyfen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: CC(COC1=CC=C(C=C1)OC2=CC=CC=C2)OC3=CC=CC=N3
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Uses: 1. It is a kind of benzyl ethers class insect growth regulator and is a kind of juvenile hormone type inhibitor of chitin synthesis. It is characterized by its high efficiency, less medication, long duration, crop safety, low toxicity to fish, and the small impact on the ecological environment. It can be used to control Homoptera, Thysanoptera, Diptera, and Lepidoptera pests. Its inhibitory inhibition on insects is related to its influence on the molting and reproduction of insect. For mosquito class sanitation pests, applying low-dose of this product for 4th instar larvae in late phase that can result in larvae’s death at the pupation stage and inhibition of the formation of adults. For the application, apply the granules directly to the sewage pond or dispersing it in the breeding ground of mosquitoes and flies. It can also be used for prevention of sweetpotato whitefly and scale insects. Pyriproxyfen also has an inner suction transfer activity which can affect the larvae hidden in the back of the blade. 2. It is used for the control of public health pests. Pyriproxyfen is a pyridine-based pesticide used against a variety of arthropoda, in particular to protect cotton crops against whitefly. Pyriproxyfen is used for control of public health pests (flies, beetles, midges, mosquitoes) by application to breeding sites.
• Description: Pyriproxyfen is a pyridine compound and, in common with fenoxycarb, is a juvenile hormone mimic whose structure is unrelated to natural juvenile hormone. It is an insect growth regulator. Fleas absorb pyriproxyfen either by direct contact or by ingesting blood from a treated animal. Pyriproxyfen is a pyridine insecticide that mimics juvenile growth hormone, which prevents larvae from developing into reproduction-capable adults. The LD50 of pyriproxyfen in rats is >5,000 mg/kg, >1,300 mg/cubic meter/4 hours, and >2,000 mg/kg through oral, inhalation, or percutaneous dosing, respectively. It is used as a larvicide in the drinking water of 11 municipalities in Brazil and rumors suggested it may be correlated with the increase in cases of microcephaly in Brazil. The acceptable daily intake determined by the World Health Organization is 0.3 mg/L. The prevalence of microcephaly in Brazil is not higher in municipalities that use pyriproxyfen in the water supply, compared with municipalities that use the larvicide Bti. In addition, in zebrafish, even very high doses (0.1 μg/ml, compared with 0.01 μg/ml used in practice for pest control) pyriproxyfen does not induce microcephaly or other brain malformations. Formulations containing pyriproxyfen are used for flea control in dogs and as an insecticide for ants.

Technology Process of Pyriproxyfen

There total 2 articles about Pyriproxyfen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.9%

2-chloropyridine (109-09-1) + 4-phenoxyphenyl (R,S)-2-hydroxypropyl ether (57650-78-9) → pyriproxyfen (95737-68-1)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 50 - 110 ℃; Solvent; Temperature; Reagent/catalyst;

Reference yield:

→ pyriproxyfen (95737-68-1)

Guidance literature:

Reference yield: 95.0%

tetrafluoroboric acid diethyl ether (67969-82-8) + sodium tetrafluoroborate (13755-29-8) + thianthrene-5-oxide (2362-50-7) + pyriproxyfen (95737-68-1) → C32H26NO3S2(1+)*BF4(1-)

Guidance literature:

tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; pyriproxyfen; With trifluoroacetic anhydride; In acetonitrile; at 0 - 25 ℃; for 3h; Sealed tube;

sodium tetrafluoroborate; In dichloromethane; water;

upstream raw materials:

2-chloropyridine

4-phenoxyphenyl (R,S)-2-hydroxypropyl ether

Refernces

• 1、 -. "COMPLEX CATALYST, PROCESS FOR PRODUCING THE COMPLEX CATALYST, AND PROCESS FOR PRODUCING ALCOHOL DERIVATIVE WITH THE COMPLEX CATALYST". . . Retrieved 2008/06/13.
• 2、 -. "Insecticidal combination to control mammal fleas, in particular fleas on cats and dogs". . . Retrieved 2008/06/13.