26046-85-5

Basic information

• Product Name: D-Phenothrin
• Synonyms: (1r)-trans-phenothrin;(1r-trans)-henyl)methyleste;2,2-dimethyl-3-(2-methyl-1-propenyl)-,(3-phenoxyphenyl)methylester,(1r-trans)-cyclopropanecarboxylicaci;D-TRANS-PHENOTHRIN;D-PHENOTHRIN;(1R-trans)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid-(3-phenoxyphenyl)methyl ester-;m-phenoxybenzyl (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate;d-trans-phenothrin (bsi,ido,ban)
• CAS NO: 26046-85-5
• Molecular Formula: C₂₃H₂₆O₃
• Molecular Weight: 350.45
• EINECS: 247-431-2
• Mol File: 26046-85-5.mol

Chemical Properties

• Boiling Point: 437 °C at 760 mmHg
• Flash Point: 186.6 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: 0-6°C
• Water Solubility: <0.01 mg l-1 (25 °C)
• CAS DataBase Reference: D-Phenothrin(CAS DataBase Reference)
• NIST Chemistry Reference: D-Phenothrin(26046-85-5)
• EPA Substance Registry System: D-Phenothrin(26046-85-5)

Safety Data

• Hazardous Substances Data: 26046-85-5(Hazardous Substances Data)

Usage

Uses

Used in Public Health:
D-Phenothrin is used as an insect control agent for public health purposes. It is particularly effective against mosquitoes, flies, and other insects that can transmit diseases to humans. The application of D-Phenothrin helps in reducing the spread of vector-borne illnesses, thus contributing to a healthier population.
Used in Stored Grain Protection:
In the agricultural industry, D-Phenothrin is used as a protectant for stored grain. It helps in preventing infestations by various stored product pests, such as beetles, weevils, and moths. By controlling these insects, D-Phenothrin ensures the preservation of grain quality and quantity, reducing losses and maintaining food security.

Metabolic pathway

Phenothrin is the name given to the 1RS-cis-trans isomer mixture (racemic). The product now used is d-phenothrin which is 95% 1R and 75% trans. It has no field use because the chrysanthemate moiety is very sensitive to photodegradation. Nevertheless, information on its photochemistry and its fate in soils and plants has been published. Several studies in rodents have been reported; this is a reflection of its use in public health. Phenothrin is degraded mainly by photo-oxidation and by hydrolysis and oxidation in plants and animals.

Degradation

Phenothrin is stable under normal storage conditions but it is labile to base, being hydrolysed to trans-2,2-dimethyl-3-(2-methylprop-1-enyl)- cyclopropanecarboxylic acid (11, trans-chrysanthemic acid) and 3-phenoxybenzyl alcohol (13,3PBAlc) (Scheme 2). It is sensitive to light and, for example, as a thin film at midday in the summer at 55 ° N, it was degraded with a DT50 of 2.5-3.0 hours (Samsonov and Makarov, 1996). When (lR)-trans-[14C-carboxyl]phenotwhraisn irradiated in degassed benzene solution, the only product was the cis-isomer. However, in oxygenated benzene solution, degradation was about 10-fold faster and many products were detected (Ruzo et al., 1982). A similar array of products was seen on exposure of thin films to sunlight. Major products (Scheme 1) were formed by oxidation at the isobutylene substituent giving the epoxide (2), the alcohol (3), the aldehyde (4) and the carboxylic acid (5). Caronaldehyde (6) and the caronic acid derivative (7) were formed by cleavage of ozonolysis products and the hydroperoxide (8) was formed by ene reactions at the 1’-position. Ester cleavage to 3PBAlc, 3PBAl and 3PBA (not shown in Scheme 1) was relatively minor.

InChI:InChI=1/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3/t20?,21-/m0/s1

Upstream product

• 884846-74-6 vinyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 
• 13826-35-2 3-Phenoxybenzyl alcohol 
• 4489-14-9 (1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride 
• 79-37-8 oxalyl dichloride 
• 13499-05-3 hafnium tetrachloride 
• 10453-89-1 chrysanthemumic acid 
• 10026-11-6 zirconium(IV) chloride 

Downstream Products

• 68086-49-7 (1R,3S)-3-((Z)-2-Chloro-3,3,3-trifluoro-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 107686-47-5 (3-phenoxyphenyl)methyl (1RS,3SR)-3-(2,2-dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,2-dimethylcyclopropanecarboxylate 
• 107686-50-0 (3-phenoxyphenyl)methyl (1RS,3SR)-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)-2,2-dimethylcyclopropanecarboxylate 
• 52611-74-2 (1R,3R)-3-((S)-3,3-Dimethyl-oxiranyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 52611-73-1 (1R,3R)-3-((R)-3,3-Dimethyl-oxiranyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 146205-06-3 (1R,3R)-3-((E)-2-Formyl-3-hydroxy-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 145551-95-7 (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxo-propenyl)-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 145551-94-6 (1R,3R)-3-((E)-3-Hydroxy-2-methyl-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 

Relevant articles and documents

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