Propoxur

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China

Propoxur

Common name: propoxur
IUPAC name: 2-isopropoxyphenyl methylcarbamate
Chemical Abstracts name: 2-( 1-methylethoxy) phenyl methylcarbamate
CAS RN: [ 114-26-1]

PHYSICAL CHEMISTRY
Mol. wt.: 209.2; M.f.: C11H15NO3; Form: Colourless crystals; ( tech., white to cream-coloured crystals) . M.p.: 90 º C ( crystal form I) , 87.5 º C ( crystal form II, unstable) . B.p.: Decomposes on distillation. V.p.: 1.3 mPa ( 20 º C) ; 2.8 mPa ( 25 º C) . KOW: logP = 1.56; Henry: 1.5x10-4 Pa m3 mol-1 ( 20 ° C) . S.g./ density: 1.18 ( 20 º C) . Solubility: In water 1.9 g/ l ( 20 º C) . Soluble in most organic solvents, e.g. isopropanol > 200, toluene 50-100, hexane 1-2 ( all in g/ l, 20 º C) . Stability: Stable in water at pH 7. Hydrolysed by strong alkali; DT50 ( 22 º C) 1 y ( pH 4) , 93 d ( pH 7) , 30 h ( pH 9) ; DT50 ( 20 º C) 40 min ( pH 10) . Direct photodegradation is not a major contributor to the overall elimination of propoxur from the environment ( DT50 5-10 d) ; indirect photodecomposition ( addition of humic acid) is more rapid ( DT50 88 h) .

APPLICATIONS
Biochemistry: Cholinesterase inhibitor.
Mode of action: Non-systemic insecticide with contact and stomach action. Gives rapid knockdown, and has long residual activity.
Uses: Control of cockroaches, flies, fleas, mosquitoes, bugs, ants, millipedes and other insect pests in food storage areas, houses, animal houses, etc. Control of sucking and chewing insects ( including aphids) in fruit, vegetables, ornamentals, vines, maize, alfalfa, soya beans, cotton, sugar cane, rice, cocoa, forestry, etc.; also against migratory locusts and grasshoppers.
Phytotoxicity: Chrysanthemums, carnations, and hydrangeas may be injured at higher dose rates. Blossom thinning may occur on fruit trees.
Formulation types: AE; DP; EC; FU; GR; RB; SL; UL; WP; Oilspray.
Compatibility: Mixtures with alkaline substances are not stable.

MAMMALIAN TOXICOLOGY
Oral: Acute oral LD50 for male and female rats c. 50 mg/ kg.
Skin and eye: Acute percutaneous LD50 ( 24 h) for male and female rats > 5000 mg/ kg. Non-irritating to skin; slightly irritating to eyes ( rabbits) .
Inhalation: LC50 for rats ( 4 h) > 0.5 mg/ l ( aerosol) ; 0.654 mg/ l air ( dust) .
NOEL: ( 2 y) for rats 200, mice 500 mg/ kg diet; ( 12 mo) for dogs 200 mg/ kg diet.
ADI: 0.02 mg/ kg b.w.
Toxicity class: WHO ( a.i.) II; EPA ( formulation) II
EC hazard: T; R25| N; R50, R53

ECOTOXICOLOGY
Birds: Dietary LC50 ( 5 d) for bobwhite quail 2828, mallard ducks > 5000 mg/ kg diet.
Fish: LC50 ( 96 h) for bluegill sunfish 6.2-6.6, rainbow trout 3.7-13.6, golden orfe 12.4 mg/ l.
Daphnia: LC50 ( 48 h) 0.15 mg/ l.
Bees: Highly toxic to bees.

ENVIRONMENTAL FATE
Animals: In rats, the principal metabolites are 2-hydroxyphenyl-N-methylcarbamate and 2-isopropoxyphenol; minor metabolites include 5-hydroxy propoxur and N-hydroxymethyl propoxur. Elimination is very rapid, 96% excreted in the urine. Metabolism of carbamate insecticides is reviewed.
Plants: The primary metabolite is demethyl propoxur ( max. amount 2.7-3.6% ) .
Soil/ Environment: The mobility of propoxur in the soil is relatively high. The compound rapidly degrades in different soils.

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