Fenazaquin Chemical Properties

Melting point:

70-71° (Dreikorn); mp 77.5-80.0° (Gambie)

Boiling point:

447.01°C (rough estimate)

Density 

1.0970 (rough estimate)

vapor pressure 

3.4 x l0^-6 Pa (25 °C)

refractive index 

1.5700 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

Water Solubility 

0.102 mg l^-1 (20 °C, pH 7)

pka

2.88±0.30(Predicted)

form 

solid

color 

White to off-white

BRN 

8331263

Major Application

agriculture
environmental

InChI

1S/C20H22N2O/c1-20(2,3)16-10-8-15(9-11-16)12-13-23-19-17-6-4-5-7-18(17)21-14-22-19/h4-11,14H,12-13H2,1-3H3

InChIKey

DMYHGDXADUDKCQ-UHFFFAOYSA-N

SMILES

CC(C)(C)c1ccc(CCOc2ncnc3ccccc23)cc1

LogP

5.510

CAS DataBase Reference

120928-09-8(CAS DataBase Reference)

EPA Substance Registry System

Fenazaquin (120928-09-8)

Safety Information

Hazard Codes 

T,N

Risk Statements 

20-25-50/53

Safety Statements 

37-45-60-61

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

VA1382000

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Acute Tox. 3 Oral
Acute Tox. 4 Inhalation
Aquatic Acute 1
Aquatic Chronic 1

Hazardous Substances Data

120928-09-8(Hazardous Substances Data)

Toxicity

LD50 orally in rats, mice (mg/kg): 134, 1480; dermally in rabbits (mg/kg): >5000; LC50 (96 hr) in bluegill, trout (mg/l): 34.1, 3.8 (Longhurst)

MSDS

• Language:English Provider:Fenazaquin

Fenazaquin Usage And Synthesis

Uses

Fenazaquin is a non-systemic acaricide/insecticide used widely in controlling mites and other related pests in fruits, vegetables and tea.

Uses

Fenazaquin is an acaricide mainly used for control of mites (Eutetranychus, Panonychus and Tetranychus spp.) on pome and citrus fruits and glasshouse-grown ornamental plants.

Uses

Acaricide and insecticide.

Definition

ChEBI: Fenazaquin is a member of quinazolines. It has a role as an acaricide and a mitochondrial NADH:ubiquinone reductase inhibitor.

Synthesis

A novel method for the preparation of the acaricide fenazaquin:

1) 4-tert-butylphenethyl alcohol (5 g, 28.0 mmol) and THF (200 mL) were added in a 500 ml reactor, and PPh₃ (8.80 g, 33.7 mmol) was added in a single addition and N-bromosubstituted butylenediimide (NBS, 6.0 g, 33.7 mmol) was added in batches sequentially, and the reaction solution was stirred at 25??C for For 4h, the tetrahydrofuran in the reaction solution was spun dry, dissolved in dichloromethane, washed twice with 150 ml of water, washed once with 150 ml of saturated saline, and separated by column chromatography (petroleum ether: ethyl acetate = 10:1) to give compound 2-(4-tert-butylphenyl)ethyl bromide 5.8 g in 85.8% yield.

2) In a 500mL four-port reactor equipped with a stirrer, a thermometer and a dropping funnel, 4-hydroxyquinazoline (3.5 g, 24.0 mmol) and 200 ml of dichloromethane were added, and the reaction was carried out under stirring at a controlled temperature of 25??C with dropwise addition of 50 ml of dichloromethane solution of 2-(4-tert-butylphenyl)ethyl bromide (5.8 g, 24.0 mmol), and the drop was completed in about 1h, and then the reaction was Raise to 40 ?? reaction 3h, add 400mL of water, separation of the organic layer, the aqueous layer was extracted with 2× 50mL of dichloromethane, combined organic layer. Concentrated under reduced pressure, the crude product was recrystallized from n-hexane to obtain a white solid 5.88g, melting point 72-74 ??, content 98.1%, yield 80%.

Metabolic pathway

Fenazaquin is a lipophilic compound and hence is immobile in soils and is not translocated in plants. The main pathways of metabolism involve cleavage of the bridging group between the quinazoline and phenyl rings, oxidation of the tert-butyl sustituent and of the heterocyclic portion of the quinazoline ring and cleavage of that ring. Most of the information is taken from a pamphlet produced by the manufacturer of the compound in which full experimental details were not given (DowElanco, 1993).

Degradation

Fenazaquin is hydrolysed under acidic conditions but the rate is slow under neutral and alkaline conditions. Half-lives were 8,442 and 584 days (22 °C) at pH values of 5, 7 and 9, respectively. Hydrolysis occurs by cleavage of the ether linkage to form quinazolin-2-ol (2) and an alcohol (3) as shown in Scheme 1. The major route of degradation in aquatic environments is by photolysis, the main products (2 and 3) being formed by cleavage of the ether lmkage and include the alkene (4) (DowElanco, 1993).

Fenazaquin(120928-09-8)Related Product Information

• ACEQUINOCYL
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• Azocyclotin
• Benzoximate
• Diphenyl ether
• Ethoxyquin
• Phenyl salicylate
• PHENYL VALERATE
• Sulfaquinoxaline
• PHENYL RESIN
• 2-(4-tert-Butylphenyl)ethanol
• Phenylacetic acid
• Ethoxy
• Fenazaquin
• FENAZAQUIN SOLUTION 100UG/ML IN ACETONITRILE 1ML
• FENAZAQUIN SOLUTION 100UG/ML IN TOLUENE 1ML