| Chemical |
Permethrin |
| CAS-number : |
52645-53-1 |
| |
| Synonyms : |
| 3-Phenoxybenzyl-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate |
| Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2- dimethyl-, (3-phenoxyphenyl)methyl ester |
| Permetriini |
| |
| Sumformula of the chemical : |
| C21H20Cl2O3 |
| EINECS-number : |
| 2580679 |
| |
| Uses : |
Active ingredient in insecticides.
|
| |
| Molecular weight : |
391.31 |
| |
| Vapor pressure, mmHg : |
| 0.0000001 |
exact 0.000000018 mmHg, KEMI 1990 |
| |
| Water solubility, mg/l : |
| 0.04 |
room temperature |
| |
-- |
| 0.2 |
at 20°C, KEMI 1990 |
| |
| Melting point, °C : |
| 63 |
63 - 65 °C |
| 65 |
KEMI 1990 |
| |
| Log octanol/water coefficient, log Pow : |
| 6.5 |
at 25°C, KEMI 1990 |
| |
| Mobility : |
Permethrin is bound very tightly to soil and it can be kept
almost immobile.
Trans-isomer and some of degradationproducts
are bound lighter than cis-isomer.
Koc: 14000 for permethrin
and Koc: 70 - 350 for degradationproducts (KEMI 1990).
|
| |
| Photochemical degradation in air : |
Permethrin is degraded for instance from surfaces of leaves
very slowly because of slow photolysis (KEMI 1990).
|
| |
| Hydrolysis in water : |
About 90% of permethrin has been hydrolyzed at pH 7 during 30 -
40 days.
At higher pH it will hydrolyzed quicklier.
Cis-isomer
is more stabile against photolysis and hydrolysis than
trans-isomer (KEMI 1990).
|
| |
| Degradation and transformation products : |
cis/trans-3-(2,2-diclorovinyl)-2,2-dimethylcyclopropane-
carboxylate; 3-phenoxybenzylalcohol; 3-phenoxybenzoate
(KEMI 1990).
|
| |
| Other information of degradation : |
Permethrin degrades in soil and water by influence of
microorganisms.
The half-life for primary degradation in soil
is 5 - 12 days at 25°C and 14 - 55 days at 10°C.
Degradation is
prevented in soil, if it contains high amount organic material.
In natural water degradation is prevented, because permethrin
is bounded to particles and sediment (KEMI 1990).
|
| |
| Bioconcentration factor, fishes : |
| 55 |
Salmo salax, Verschueren 1983 |
| |
-- |
| 290 |
290-620, embryo, Cyprinodon variegatus, |
| 620 |
AQUIRE 1994 |
| |
| Other information of bioaccumulation : |
Bioconcentration factor (crustaceans):
800 - 2400, blue-green algae (KEMI 1990). |
| |
| LD50 values to mammals in oral exposure, mg/kg : |
| 410 |
orl-rat, Lewis & Sweet 1984 |
| |
-- |
| 500 |
500 - 4000, orl-rat, orl-mus, orl-gpg, |
| 4000 |
orl-rbt, KEMI 1990 |
| |
| LD50 values to mammals in non-oral exposure , mg/kg : |
| 4000 |
>4000, idr-rat, idr-rbt, KEMI 1990 |
| |
| LC50 values to mammals in inhalation exposure, mg/m3 : |
| 23500 |
>23.5 mg/l, ihl-rat, KEMI 1990 |
| |
| LD50 values to birds in oral exposure, mg/kg : |
| 3500 |
>3500 mg/kg, body weight, KEMI 1990 |
| |
| Subacute LC50 values to birds in feeding ex posure, mg/kg : |
| 10000 |
>10000 mg/kg, 8d, feed, KEMI 1990 |
| |
| Effects on amphibia : |
LD50, 0.14 - 7.5 mg/kg, Rana pipiens (KEMI 1990).
|
| |
| Effects on invertebrates : |
LC50, 2 d:
0.0074 mg/l, Ophiogomphus sp.;
0.0032 mg/l, Pycnopsyche sp.;
0.0045 mg/l, Simulium venustum
(Poirier & Surgeoner 1987).
Invertebrates, 8.8 g/ha, 1 d, change in species diversity
(Kreutzweiser & Kingsbury 1987).
|
| |
| Effects on bees : |
LD50, 24hr, 0.19 - 0.28 ug/bee (KEMI 1990).
|
| |
| Effects on anthropods : |
Aedes aegypti, LC50, 3 d, 0.00152 mg/l (Helson et al. 1986).
Insecta: 8.8 g/ha, 0.5 d, changes in number of larval aquatic
insects to travel a given distance in a stream.
(Kreutzweiser & Kingsbury 1987).
|
| |
| EC50 values to algae, mg/l : |
| 1.6 |
1.6 - 5 mg permethrin/l, Anabaena |
| 5 |
inaequalis, KEMI 1990 |
| |
| LC50 values to crustaceans, mg/l : |
| 0.0002 |
0.0002 - 0.0006, 48 hr, Daphnia magna |
| 0.0006 |
Stratton & Corke 1981 |
| |
-- |
| 0.00014 |
96 hr, Crangon sepstemspiosa, |
| 0.00073 |
96 hr, Homarus americanus |
| |
McLeese et al. 1980 |
| |
-- |
| 0.00025 |
0.00025 - 0.00037, 2d |
| 0.00037 |
Gammarus pseudolimnaeus |
| |
Helson et al. 1986 |
| 0,006 |
96 hr, 21 °C, Nitocra spinipes,
Ambush* (permethrin 250 g/l), Linden et al. 1979 |
| |
| EC50 values to crustaceans, mg/l : |
| 0.0001 |
0.0001 - 0.0002, 48hr, Daphnia magna |
| 0.0002 |
KEMI 1990 |
| |
| NOEC values to crustaceans, mg/l : |
| 0.1 |
23d, rpd, Daphnia magna, KEMI 1990 |
| |
| LC50 values to fishes, mg/l : |
| 0.0025 |
96 hr, Salmo gairdneri, Nikunen et al. |
| |
1986 |
| |
-- |
| 0.006 |
48hr, Salmo gairdneri |
| |
Mulla et al. 1978 |
| |
-- |
| 0.009 |
48hr, Salmo salar,Zitko et al.1977 |
| |
-- |
| 0.016 |
96hr, Pimephales promelas |
| 0.007 |
96hr, Salmo gairdneri |
| |
Holcombe et al. 1982 |
| |
-- |
| 0.0011 |
96hr, Ictalurus punctatus |
| 0.015 |
96hr, Gambusia affinis |
| |
Jolly et al. 1978 |
| |
-- |
| 0.0012 |
96hr, Salmo salar,McLeese et al.1980 |
| |
-- |
| 0.009 |
96hr, Salmo gairdneri |
| |
Pesticide Manual 1983 |
0.004-0.008 |
--
96 hr, 10 °C, Alburnus alburnus,
Ambush* (permethrin 250 g/l), Linden et al. 1979 |
| |
| LOEC values to fishes, mg/l : |
| 0.0014 |
srv, schr, Pimephales promelas |
| |
Spehar et al. 1983 |
| |
| NOEC values to fishes, mg/l : |
| 0.007 |
srv, schr, Pimephales promelas |
| |
Spehar et al. 1983 |
| |
| Effects on physiology of water organisms : |
Salmo gairdneri, 0.00065 mg/l, 42 d, measurable change in
length and/or weight (Kumaraguru & Beamish 1986).
|
| |
| Other information of water organisms : |
LC50 (6hr), 0.0006 - 0.0021 mg/l, Hexagenia rigida
(Friesen et al. 1983).
Permethrin has in general low acute toxicity to green algae and
blue-green algae, expect the blue-green algae Anabaena
inaequalis.
Degradationproducts 3-phenoxybenzaldehyde and
3-phenoxybenzylalcohol have little higher toxicity for algae
than permethrin (KEMI 1990).
|
References |
| 70 | Anon. 1983c.
Pesticide Manual.
Worthing, C.R.
(toim.)
A world compedium.
The British Crop Biotection Council.
London. 7 th edition. |
| 3107 | AQUIRE 1993 -.
Aquatic Toxity Information Retrieval Database.
U.S.Environmental Protection Agency, Office of Pesticides and
Toxic Substances, Washington, D.C.
|
| 452 | Friesen, M.K. et al. 1983.
Toxicity of the insecticide
permethrin in water and sediment to nymphs of the
burrowing mayfly Hexagenia rigida (Ephemeroptera: Ephemeridae).
Can.
Entomol. 115: 1007. |
| 2053 | Helson, B.V. et al. 1986.
The use of bioassays to assess
aquatic arthropod mortality from permethrin drift deposits.
Aquat.
Toxicol. 9: 253. |
| 593 | Holcombe, G.W., Phipps, G.L. & Fiandt, J.T. 1982.
Effects
of phenol, 2,4-dimethylphenol, 2,4-dichlorophenol and
pentachlorophenol on embryo, larval and early-juvenile
fathead minnows.
Arch.
Environ.
Contam.
Toxicol. 11: 73 - 78. |
| 592 | Holcombe, G.W. et al. 1982.
The acute toxicity of Kelthane,
Dursban, Disulfoton, Pydrin, and Permethrin to fathead
minnows Pimephales promelas and rainbow trout Salmo
gairdneri.
Environ.
Pollut., 29A: 167. |
| 673 | Jolly, A.L. et. al. 1978b.
Acute toxicity of permethrin to
several aquatic animals.
Trans.
Amer.
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| 672 | Jolly, A.L. et al. 1978a.
Effects of a new insecticide
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| 3101 | KEMI 1990 - 1991.
Kemikalieinspektionens ämnesblad.
Faktablad
för verksamma ämnen i bekämpningsmedel avsedda för jordbruk och
trädgårdsnäring mm. |
| 2054 | Kreutzweiser, D.P. & Kingsbury, P.D. 1987.
Permethrin
treatments in Canadian forests.
Part 2: Impact on stream
invertebrates.
Pestic Sci. 19: 49. |
| 2055 | Kumaraguru, A.K. & Beamish, F.W.H. 1986.
Effect of permethrin
(NRDC-143) on the bioenergetics of rainbow trout, Salmo
gairdneri.
Aquat.
Toxicol. 9: 47. |
| 1589 | Lewis, R.J. & Sweet, D.V. 1984.
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chemical substances.
National Institute for Occupational Safety
and Health.
No. 83-107-4. |
| 831 | Linden, E., Bengtsson, B-E., Svanberg, O. & Sundström, G.
1979.
The acute toxicity of 78 chemicals and pesticide
formulations against two brackish water organisms, the
bleak (Alburnus alburnus) and the harpacticoid Nitocra
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Chemosphere 11/12: 843 - 851. |
| 943 | McLeese, D.W. et al. 1980.
Lethality of aminocarb and the
components of the aminocarb formulation to juvenile atlantic
salmon, marine invertebrates, and freshwater clam.
Chemosphere,
9: 79. |
| 999 | Mulla, M.S. et al. 1978.
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pyrethroids to four species of freshwater fishes Environm.
Entomol. 7: 428. |
| 1047 | Nikunen, E., Miettinen, V. & Tulonen, T. 1986.
Kemikaalien
myrkyllisyys vesieliöille. -
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60(6): 994 - 1065. |
| 1900 | Poirier, D.G. & Surgeoner, G.A. 1987.
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| 1348 | Spehar, R.L., Tanner, D.K. & Nordling, B.R. 1983.
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synthetic pyrethroids, permethrin and AC 222, 705 and
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and snails.
Aquat.
Toxicol. 3: 171 - 182. |
| 1381 | Stratton, G.W. & Corke, C.T. 1981.
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permethrin with Daphnia magna in the presence and absence of
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Environ.
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| 1468 | Verschueren, K. 1983.
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organic chemicals.
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| 1586 | Zitko, V. et al. 1977.
Seasonal and developmental
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J.
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| 1587 | Zitko, V. et al. 1977.
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