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D-Phenothrin

D-Phenothrin Structure
CAS No.
26046-85-5
Chemical Name:
D-Phenothrin
Synonyms
D-PHENOTHRIN;D-permethrin;D-trans-Phenot;D-TRANS-PHENOTHRIN;rich-d-t-Phenothrin;(-)-trans-Phenothrin;(1r)-trans-phenothrin;Pesticide D-Phenothrin;(1r-trans)-henyl)methyleste;d-trans-phenothrin (bsi,ido,ban)
CBNumber:
CB9699395
Molecular Formula:
C23H26O3
Molecular Weight:
350.45
MOL File:
26046-85-5.mol
MSDS File:
SDS
Modify Date:
2024/3/27 17:09:02

D-Phenothrin Properties

Boiling point 437.0±45.0 °C(Predicted)
Density 1.120±0.06 g/cm3(Predicted)
vapor pressure 1.9×10-5Pa (21.4 °C)
storage temp. Sealed in dry,2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form Oil
Water Solubility <0.01 mg l-1 (25 °C)
color Colourless to Dark Yellow
CAS DataBase Reference 26046-85-5(CAS DataBase Reference)
EPA Substance Registry System d-Phenothrin (26046-85-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS09
Signal word  Warning
Hazard statements  H410
Precautionary statements  P273-P391-P501
Toxicity LD50 oral in mouse: > 10gm/kg

D-Phenothrin Chemical Properties,Uses,Production

Uses

Phenothrin is used for the control of insects for public health. It is also used to protect stored grain.

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.

D-Phenothrin Preparation Products And Raw materials

Raw materials

Preparation Products

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(1R)-2β-(2-Methyl-1-propenyl)-3,3-dimethylcyclopropane-1α-carboxylic acid m-phenoxybenzyl ester (1R)-3,3-Dimethyl-2β-(2-methyl-1-propenyl)cyclopropane-1α-carboxylic acid 3-phenoxybenzyl ester (1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 3-phenoxybenzyl ester (1R,3R)-2,2-Dimethyl-3α-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester (1R-trans)-2,2-Dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylic acid D-trans-Phenot (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- d-trans-phenothrin (bsi,ido,ban) (1R-trans)-2,2-Dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylic acid, (3-phenoxyphenyl)methyl ester 3-Phenoxybenzyl (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate 3-PHENOXYBENZYL(+)-TRANS-CHRYSANTHEMATE rich-d-t-Phenothrin (1R)-2,2-Dimethyl-3α-(2-methyl-1-propenyl)cyclopropane-1β-carboxylic acid 3-phenoxybenzyl ester m-phenoxybenzyl (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate Pesticide D-Phenothrin (3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)-1-cyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (3-phenoxyphenyl)methyl ester, (1R,3R)- (-)-trans-Phenothrin (1R,3R)-3-Phenoxybenzyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate D-permethrin 26046-85-5