PERMETHRIN

1. Exposure Data

1.1 Chemical and physical data

Permethrin is tyically a mixture of ( + ) cis and ( + ) trans esters of the general structure
shown below, in either a 40:60 or 25:75 ratio.

1.1.1 Synonyms, structural and molecular data

Table 1. Chemical Abstract Services Registry numbers, names and synonyms of
permethrin
Name CAS Reg. Chem. Abstr. namesb and synonyms
Nosa

Permethrin 5265-53- 1 3. (2,2- D iehloroethe nyl). 2,2. dimethylcyclopropa neearboxylie

(57608-04- 5; acid, (3.phenoxyphenyl)methyl ester; meta-phenoxybenzyl
6018-94-2; 3-(2, 2-d ichloroviny 1)- 2,2-dim ethy lcyclopropanecarboxyla te;
63364-00- 1; 3-phenoxybenzy 1 (1 RS)-cis ,trans- 3-(2, 2-dichloroviny 1)- 2,2-
75497-64-2; dimethylcyclopropanecarboxylate (IUPAC); 3-phenoxybenzyl
93388-66-0) (1 RS,3 RS; 1 RS,3SR)- 3-(2, 2-dich 10 rovinyl)- 2, 2-d im ethylcyclo-
propanecarboxylate (IUPAC); 3-phenoxybenzyl-2,2-dimethyl-
3-(2,2-dichlorovinyl)cclopropanecarboxylate; FMC 33297; FMC
41655; ICI-PP 557; NRDC 143; OMS 1821; WL 43479
trans- Permethrin 61949-77-7 Irans. 3- (2,2. D ieh loroethe nyl). 2,2- d imethylcyclop ropaneearbox.
ylie acid, (3-phenoxyphenyl)methyl ester; trans-meta-phenoxyben-
zyl 3-(2, 2-dichlorovinyl)- 2, 2-dim ethylcyclopropan eca rboxyla te
cis- Permethrin 61949-76-6 cis. 3. (2,2- Dich loroethenyl). 2,2. d i methyleyelopropaneearboxyl ie
acid, (3-phenoxyphenyl)methyl ester; cis-meta-phenoxybenzyl
3-(2,2-d ichlorovinyl)- 2,2-d im ethy lcycl opropa n ecarboxyla te; cis-
permethrin
(- )-trans- Permethrin 54774-47-9 (1 S.lrans ).3.(2,2. Diehloroethenyl)- 2,2.dimethylcyclopropane-
carboxylie aeid, (3-phenoxyphenyl)methyl ester; lS-trans-per-
methrin
(- )-cis- Permethrin 54774-46-8 (1 S-cis ).3. (2,2. Dichloroethenyl)- 2,2- dimethylcyclopropanecar-
boxylie acid, (3.phenoxyphenyl)methyl ester; 1S-cis-permethrin
( + )-cis-Permethrin 54774-45-7 (1 R.cis )-3. (2,2. Diehloroethenyl)- 2,2-dimethylcyclopropaneear-
boxylie acid, (3.phenoxyphenyl)methyl ester; 1R-cis-permethrin;
NRDC 167
(::)-cis-Permethrin 52341-33-0 cis. (::). 3. (2,2. D ichloroethenyl). 2,2-d imethylcyclopropanecar-
boxylie acid, (3-phenoxyphenyl)methyl ester; (::)-cis-FMC
33297; FMC 35171; NRDC 148; 1RS-cis-permethrin

- 329 -
330 IARC MONOGRAPHS VOLUME 53

Table i (contd)

Name CAS Reg. Chem. Abstr. namesb and synonyms

Nasa

(:f)-trans- Permethrin 52341-32-9 trans. (:f)-3. (2,2. Dichloroethenyl). 2,2.dimethylcyclopropane-

carboxylic acid, (3.phenoxyphenyl)methyl ester; NRDC 146;
1RS-trans-permethrin
( + )-trans-Permethrin 51877-74-8 Biopermethrin; (1R.trans).3.(2,2-dichloroethenyl).2,2.dimethyl.
cydopropanecarboxylic acid, (3.phenoxyphenyl)methyl ester;
NRDC 147; 1R-trans-permethrin; RU 2209

~eplaced CAS Registry number(s) in parentheses

aln bold

\/
CH3 CH3

CI2C = CH- C~ \CH- COO- CH2 -- oJ9

C21H20Cli03 MoL. wt: 391.3

1.1.2 Chemical and physical properties

(a) Description: Colourless to white, odourless crystalline solid (pure); viscous brown
Iiquid or crystalline solid with a sweet odour (technical) (Swaine & Tandy, 1984;
Roussel Bio Corp., undated)
(b) Boilng-point: 220°C at 0.05 mm Hg (6.7 x 10-3 kPa) (Roussel Bio Corp., undated);
(c) Melting-point: 34-39°C (technical), 63-65°C (cis-isomers), 44-47°C (trans-isomers)
(Worthing & Walker, 1987; WHO, 1990)
(d) Solubility: Insoluble in water (0.2 mg/l at 30°C); soluble in or miscible with most
organic solvents (acetone (450 g/l), chloroform, cyclohexanone, ethanol, ether,
hexane (:: 1 kg/kg at 25°C), methanol (258 g/kg at 25°C), dichloromethane, xylene
(:: 1 kg/kg at 25°C) (Swaine & Tandy, 1984; Worthing & Walker, 1987; The Royal
Society of Chemistry, 1989; WHO, 1990; Roussel Bio Corp., undated)
(e) Volatilty: Vapour pressure, 3.4 x 10-7 mm Hg (0.45 x 10-7 kPa) at 25°C (technical)
(FMC Corp., 1984); 15 x 10-9 mm Hg (2.0 x 10-9 kPa) at 20°C (cis-isomer), 7.5 x
10-9 mm Hg (1.0 x 10-9 kPa) at 20°C (trans-isomer) (Swaine & Tandy, 1984)
if Stability: Stable in neutral and weak acidic media, but hydrolysis can occur under
alkaline or strongly acidic conditions (Swaine & Tandy, 1984).
(g) Half-time: 10-25 days at 25°C in soil, depending on soil tye (Roussel Bio Corp.,
undated)
(h) Octanol/water partition coeffcient (P): log P, 6.5 (WHO, 1990)
 PERMETHRIN 331

(i) Conversion factor for airborne concentrationsl: mg/m3 = 16.0 x ppm

1.1.3 Trade names, technical products and impurities
Sorne examples of trade names are: Adion; Ambush; Ambushfog; Anomethrin N;
Antiborer 3768; Atroban; BW-21-Z; Cellutec; Chinetrin; Coopex; Corsair; DiffusiI H;
Dragon; Ecsumin; Ectiban; Efmethrin; Eksmin; Exmin; Imperator; Indothrin; Ipitox; Kafil;
Kavil; Kestrel; LE 79-519; MP 79; NIA 33297; Outflank; Perigen; Permanone; Permasect;
Permit; Perthrine; Picket; Pounce; PP 557; Pramex; Pynosect; Qamlin; S 3151; SBP 1513;
SBP 15131 TEC; Spartan; Stockade; Stomoxin; Talcord; Torpedo
Technical-grade permethrin contains from a minimum of 35% to a maximum of 55%
(:l)-cis isomer and from a minimum of 45% to a maximum of 65% (:l)-trans isomer (Roussel
Bio Corp., 1987; Anon., 1989). ln the common technical-grade products, the cis:trans ratio is
either 2:3 (WHO, 1990) or 1:3 (Worthing & Walker, 1987).
Permethrin is available in the USA as a technical-grade product containing 91.0-95.0%
w/w of the pure chemical and 5.0-9.0% impurities (Fairfield American Corp., 1989; Roussel
Bio Corp., 1989; ICi Americas, 1990).
Several of the minor components have been identified in technical permethrin. These
were principally: ethyl (:l)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-l-car-
boxylate, 3-phenoxyoluene, 4-phenoxybenzyl (:l)-cis ,trans- 3-(2,2-dich lorovinyl)- 2,2-di-
methylcyclopropane-1-carboxylate, and 6-bromo- 3-phenoxybenzyl (:l)-cis ,trans-3-(2,2-di-
chlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate. Other minor components were found
to be xylene (see IARC, 1989), 3-phenoxybenzyl alcohol, N,N-diethyl-3-phenoxybenzyl-
amine, 3-phenoxybenzaIdehyde and 4-(2,2-dichlorovinyl)-5,5-dimethyloxacyclopentane-2-
one (Horiba et al., 1977).
Permethriri is formulated as granules, emulsifiable concentra tes, wettable powders,
dusts, smokes, ultra-Iow-volume sprays, fumigants, aerosols, fogging solutions and
water-dispersible granules. ln one European country, registered permethrin products also
include capsule suspensions and lacquer formulations (Papadopoulou-Mourkidou, 1983;
Swaine & Tandy, 1984; The Royal Society of Chemistry, 1986, 1989; Meister, 1990). ln
Europe, permethrin is also registered in combination with piperonyl butoxide (see IARC,
1983, 1987), tetramethrin, plifenate and other pyrethrins (Royal Society of Chemistry, 1986).
1.1.4 Analysis
Selected methods for the analysis of permethrin in various matrices are given in Table 2.
Permethrin can be determined in pesticide formulations using gas chromatography with
flame ionization detection (Association of OfficiaI Analytical Chemists, 1986; WHO, 1990).
Several other methods for the determination ofpermethrin (and its individual isomers)
in various matrices, including high-performance liquid chromatography and gas chromato-
graphy, have been reviewed (Horiba et al., 1977; Miyamoto et aL., 1981; Baker & Bottomley,
1982; Papadopoulou-Mourkidou, 1983; Nehmer & Dimov, 1984; Swaine & Tandy, 1984).

lCalculated from: mg/m3 = (molecular weight/24.45) x ppm, assuming standard temperature (25°C) and
pressure (760 mm Hg r101.3 kPaD
 332 IARC MONOGRAPHS VOLUME 53

Table 2. Methods for the analysis of permethrin

Sample Sam pIe preparation Assay Limit of Reference
matri procedurea detection
Water Extract with dichloromethane; isolate GC/ECD 0.5 jlg/l US Environmental
extract; dry; concentrate with methyl (for isomers) Protection Agency
tert-butyl ether
(1989a)
Waste- Extract with dichloromethane; dry; GC/ECO 0.2 jlg/l US Environmental
water exchange into hexane (for isomers) Protection Agency
(undated)
Soil Extract with methanol:water (9:1); GC/CCDb 0.05 ppm US Food and Drug
partition into dichloromethane; dean- ( mg/kg) Administration
up on activated Florisil column
(1989)
Crops Extract with hexane; remove oil by gel GC/CCOb 0.05 ppm US Food and Orug
permeation chromatography; dean-up GC/ECOb (mg/kg) Administration
on activated Florisil column
(1989)
Milk, Extract with acetone:hexane (1:1); GC/ECOb 0.01 ppm US Food and Drug
animal partition into dimethylformamide (in (mg/l or mg/ Administration
tissue 1 % aqueous sodium sulfate solution); kg) (1989)
back-extract into hexane; dean-up on
activated Florisil column
Eggs Extract with acetone/hexane (1:1); GC/ECOb 0.02 ppm US Food and Drug
wash with 10% sodium chloride solu- (mg/kg) Administration
tion; partition into dimethylformamide (0.01 ppm (1989)
(in 1 % aqueous sodium sulfate solu- for isomers)
tion); back-extract into hexane; dean-
up on activated Florisil column plus
Merckogel or Fractosil
aAbbreviations: GC/CCD, gas chromatography/Coulson conductivity detection; GC/ECO, gas chromato-
graphy/electron capture detection
bMethod is suitable for determining total permethrin or the individual cis- and trans-permethrin isomers

1.2 Production and use

1.2.1 Production
Permethrin was first synthesized in 1973 (Swaine & Tandy, 1984) and first marketed in
1977 (WHO, 1990).
The starting acid is prepared by a variation of the conventional chrysanthemic acid
synthesis using ethyldiazoacetate in which 1,1-dichloro-4-methyl-1,3-pentadiene is reacted
with ethyldiazoacetate in the presence of a copper catalyst and the resulting ethyl
(:: )-cis ,trans- 2,2-dimethyl - 3-(2,2-di chI orovinyl )cycl opropanecarboxyla te hydro Iysed to the
free acid. The cis- and trans-isomers can be separated from one another by selective
crystallization from n-hexane in which the cis-isomer is more soluble. The starting acid is
then reacted with 3-phenoxybenzyl alcohol to give permethrin (Sittig, 1980).
Permethrin is produced currently in Japan, the United Kingdom and the USA (Meister,
1990).
 PERMETHRIN 333

1.2.2 Use

Permethrin is a synthetic contact pyrethroid insecticide with a high level of activity

against a wide range of insects, incl uding Lepidoptera, H emiptera, Diptera and Coleoptera. It is
used mainly in agriculture, where it is fast acting and effective against aIl growth stages,
particularly larvae. About 60% of the permethrin produced is used on cotton plants. Other
crops to which permethrin is applied are maize, soya beans, coffee, tobacco, rape seed oil,
wheat, barley, alfalfa, vegetables and fruit (WHO, 1990).
Permethrin is also used for control of insects in household and animal facilities and in
forest pest control, as a fog in mushroom houses, and as a wood preservative. Other
applications are in public health, particularly for insect control in buildings and in aircraft,
treatment of mosquito nets and control of human lice (WHO, 1990). It is also used for
termite control as a barrier treatment on building foundations (Anon., 1989).
Approximately 600 tonnes of permethrin are used annually worldwide. The major
countries or regions that were using permethrin in 1980 were (tonnes): the USA (263), Brazil
(38), Mexico (36) and Central America (27) (WHO, 1990). ln Finland, about 3.5 tonnes
(active ingredient) permethrin were used in 1988 (Agrochemical Producers' Association of
Finland, 1989)

1.3 Occurrence

1.3.1 Food
Samples (1954) of fruits, vegetables, grains, meats, dairy products and wine were
analysed as part of the Canadian national surveillance programme in 1984-89. A total of29
samples contained permethrin residues; of these 25 of 118 were in lettuce, 2 of 100 in pears
and 2 of 97 in tomatoes. The residue levels ranged from 0.01 to 1.67 mg/kg (Government of
Canada, 1990).
Cows were fed cis:trans (40:60)-permethrin at rates of 0.2-150 mg/kg diet for 28-31 days.
Residues plateaued in milk, with means of .( 0.01 ¡.g/g and 0.3 ¡.g/g at dietary levels of 0.2
and 150 mg/kg, respectively. Milk Ievels declined to .( 0.01 ¡.g/g within five days after
permethrin administration ceased. Residue levels of .( 0.01-0.04 and 2.8-6.2 ¡.g/g fat were
found in perirenal fat of cows given dietary levels of 0.2 and 150 mg/kg, respectively (as
reported by WHO, 1990). Levels of radioactivity retained in tissues and secreted in milk were
appreciably higher in goats treated with cis-permethrin than with trans-permethrin (Hunt &
Gilbert, 1977). ln goats dosed orally with 40:60 cis:trans permethrin equivalent to 10 mg/kg
in the di et for seven days, residues in milk also plateaud at 0.02-0.03 ¡.g permethrin
equivalents/g after five days (FAO/WHO, 1982).
ln supervsed trials in Spain and the USA with cItrus fruits, permethrin residues in the
edible parts did not exceed 0.01 mg/kg and 0.05 mg/kg, respectively, when applied at the
recommended rates. The residues were found almost exclusively in the peel (FAO/WHO,
1982).
 334 !AC MONOGRAPHS VOLUME 53

1.3.2 Occupational exposure

Four of fIve workers in Sweden who packed conifer seedlings for 6 h in a tunnel that had
been sprayed 1 h earlier with a 2% aqueous solution of permethrin, resulting in atmospheric
concentrations of permethrin of 0.011-0.085 mg/m3 in the breathing zone, did not excrete
detectable amounts of acid pyrethrin metabolites in the urine. One very short person whose
face was close to the plants and who had the highest concentration of permethrin in the
breathing zone excreted 0.26 i.g/ml permethrin acid metabolites in the urine the following
morning; in the afternoon, excretion was below the detection limit of the method. A group of
five workers who planted the treated conifer seedlings were exposed to non-detectable to low
permethrin levels in the breathing zone (mean, 0.002 mg/m3; range, not detected-0.006
mg/m3) and excreted no detectable amount of permethrin metabolites in the urine
(Kolmodin-Hedman et aL., 1982).
1.4 Regulations and guidelines
The FAO/WHO Joint Meeting on Pesticide Residues evaluated permethrin at its
meetings in 1979, 1980, 1981, 1982, 1983, 1984, 1985, 1987, 1988 and 1989 (FAO/WHO,
1980,1981, 1982, 1983, 1985a,b, 1986, 1987, 1988,1990). ln 1987, an acceptable dailyintake
of 0.05 mg/kg bw was established (40% cis:60% trans and 25% cis:75% trans material)
(FAO/WHO, 1987).
Maximum residue levels have been established by the Codex Alimentarius Commission
for permethrin in or on the following agricultural commodities (in mg/kg): coffee beans,
pistachio nuts, potatoes, rape seeds, soya beans and sugar beets, 0.05; almonds, carrots,
crude soya bean oil, dried beans, edible cottonseed oil, eggs, Japanese radishes, kohlrabi,
melons (except watermelon), milks (fat), mushrooms, peanuts, shelled peas and sweet corn,
0.1; cauliflower, citrus fruits, cottonseed, cucumbers, gherkins, horseradish, leeks, spring
onions, summer squash, wheat flour (post-harvest treatment) and winter squash, 0.5;
asparagus, blackberries, Brussels' sprouts, common beans, dewberries (boysenberries and
loganberries), eggplants, olives, peppers, raspberries (red and black), strawberries,
sunflower seeds, sunflower seed oil (crude and edible) and tomatoes, 1; broccoli, celery,
cereal grains (post-harvest treatment), currants (black, red and white), gooseberries, grapes,
head lettuce, kiwifruit, pome fruit, spinach, stone fruit and wholemeal wheat (post-harvest
treatment), 2; cabbage (Chinese, head and savoy) and kale, 5; unprocessed wheat bran
(post-harvest treatment), 10; dry sorghum straw and fodder and tea (green and black), 20;
dried apple pomace, dried hops and soya bean fodder, 50; alfalfa and maize fodder, 100
(Codex Committee on Pesticide Residues, 1990).
Maximum residue levels have been established by the Codex Alimentarius Commission
for permethrin in or on the following animal commodities (in mg/kg): edible offal
(mammalian; accommodates veterinary uses) and poultry meat, 0.1; meat (fat;
accommodates veterinary uses), 1 (Codex Committee on Pesticide Residues, 1990).
National and regional pesticide residue limits for permethrin in foods are presented in
Table 3.
 PERMETHRIN 335

Table 3. National and regional pesticide residue lImits for permethrin in foosa
Country Residue limit Commodities
or region (mg/kg)

Australia 10 Bran
5 Celery, lettuce
2 Brussels' sprouts, cereal grains, kiwifruit, mushrooms
1 Cole crops (except Brussels' sprouts)
0.5 Edible offal of goat, green beans
004 Tomatoes
0.2 Cottonseed, rapeseed, sunfower seeds
0.1 Beans (mung, navy), cattle, goats, pigs, poultry, and sheep (fat of meat),
eggs, linseed, lupins, soya beans, sugar-cane
0.05 Cattle and goat milk (in the fat), milk products (fat basis), potatoes,
sweet corn
Austriab 50 Hops
1.0 Meat, cereals, fruits, vegetables
0.1 Eggs (without shell), milk
Belgiumb 2 Grains, kiwi fruit
1 Other fruit, other vegetables
0.05 Animal fats, meat (poultry, hares, fowl, game), meat products, milk,
milk products, mushrooms, potatoes
o (O.05)C Othcr foostuffs of vegetable origin
o (O.01)C Other foodstuffs of animal origin
B razil 0.5 Cottonseed, rice
0.3 Tomatoes
0.1 Cabbage, caulifower, corn, kale
0.02 Wheat
0.01 Coffee (shelled), soya beans
Canada 2.0 Grapes
1.0 Apples, lettuce, peaches, pears
0.5 Beans, broccoli, Brussels sprouts, cabbage, celery, cucumbcrs, peppers,
plums, tomatoes
N egligible Asparagus, cattle (meat and milk), beetroot, blueberries, cauli-
flower, corn, flax, horseradish, kiwi fruits, onion, potatoes, poultry
(meat and eggs), radishes, rapeseed (canola oil), sugar beets (sugar),
sunflowers, turnips, wheat
Chile 0.05 Carcasses, eggs, milk, poultry
Denmarkb 5 Leafy vegetables
2 Berries, fruit (pome, small, stone, other), other vegetables
0.5 Citrus fruit
0.1 Carrots
Finlandb 2.0 Citrus fruit
0.5 Other foodstuffs (except cereal grains)
Franceb 2.0 Kiwifruit
1.0 Cabbage, fruit, vegetable greens (salad)
0.5 Other vegetables
0.1 Maize
336 IARC MONOGRAPHS VOLUME 53

Table 3 (contd)

Country Residue limit Commodities

or reglOn (mg/kg)

Germany 50 Hops
10 Bran
2 Cereals (except maize), cereal products (except bran), currants, kiwi-
fruit, lettuce
1.0 Other fruit, other leafy and sprout vegetables
0.5 Fruit used as vegetables
0.2 Maize, oilseed
0.1 Root vegetables
0.05 Citrus juices, kiwIfruit (without peel), raw coffee, spices, tea, tea-like
products, other foodstuffs of plant origin
Italy 1.0 Apples, cabbage, carrots, cereals, citrus fruit, cucurbitaceae, drupes,
grapes, leeks, lettuce, mushrooms (cultivated), olives, pears, potatoes,
solanaceae, spinach, sugar beets, tobacco, turnips
Japand 20 Tea
15 Exocarp of summer oranges
5 Fruit (except exocarp of summer oranges)
3 Vegetables
0.5 Sugar beets
0.2 Potatoes, etc.
Netherlandsb 2 KiwIfruit, leafy vegetables
1 Other fruit, other vegetables
O.ose Mushrooms, potatoes, animal products
o (0.051 Other foodstuffs
New Zealand 2.0 KiwIfruit
1.0 Brassica vegetables, fruit (berry, pome)
0.5 Fruiting vegetables, grapes, legumes
South Africab 0.5 Apples, grapes, lucerne, mealies (green), pears, sorghum
0.1 Beans, peas, tomatoes
0.05 Cottonseed, groundnuts, potatoes

Spainb 20 Hops (dried)

10 Alfalfa (dried)
1.0 Fruit, fruit vegetables
0.5 Cottonseed, sunflower seeds
0.05 Beetroot, maize, potatoes, rapeseed, sorghum grains, soya beans
0.01 Other plant products
Swedenb 2.0 Fruit, vegetables
0.05 Potatoes
Switzerland 2.0g KiwIfruit (whole)
0.8 Cabbage
0.5 Other foodstuffs
0.4 Fruit (except grapes and kiwIf ruit), vegetables (except cabbage and
potatoes)
O.lg KiwIfruit (pulp)
0.05 Milk
0.01 Potatoes
 PERMETHRIN 337

Table 3 (contd)

Country Residue limit Commodities

or region (mg/kg)

Taiwan 2.0 Leafy vegetables with large wrapper leaves, leafy vegetables with smaU
leaves
1.0 Fruit vegetables
0.5 Rice
USAh 60 Maize (fodder, forage)
55 Alfalfa (hay)
25 Alfalfa (fresh)
20 Almond huUs, head lettuce, leafy vegetables (except Brassica), spinach,
coUards, turnip greens
15 Range grasses
10 Arichokes
6.25 Milk fat (reflecting 0.25 ppm in whole milk)
6 Cabbage, mushrooms
5 Celery, peaches, watercress
3 Cherries, pears, cucurbit vegetables, fat (catte, goats, hogs, horses,
sheep), meat by-products (hogs)
2 Kiwifruit, tomatoes, meat by-products (catte, goats, horses, sheep)
1.0 Asparagus, avocdos, beU peppers, brocoli, Brussels' sprouts, cauli-
flower, eggplant, eggs, horseradish, papayas (limited to Florida),
turnip roots (regional registration)
0.5 Cottonseed
0.25 Meat (cattle, goats, hogs, horses, poultry, sheep)
0.15 Fat (poultry)
0.1 ions (dry bulb), pistachios, sweet maize (kernel plus cob with
Garlic, on

husks removed)
0.05 Almonds, apples, maize grain (field, pop), filberts, potatoes, soya
beans, walnuts, meat (poultry)
Ilrom Health and Welfare Canada
bSum of isomers
'Te figure in parentheses is the lower limit for determining residues in the corresponding
product according to the standard method of analysis.
dStandard for withholding registration of agricultural chemicals
eA pesticide may be used on an eating or drinking ware or raw material without a demonstrable residue
remaining; the value listed is considered the highest concentration at which this requirement is deemed
to have been met.
fResidues shaU be absent; the value in parentheses is the highest concentration at which this requirement
is stil deemed to have been met.
q'ese upper 'limit values' are maximum concentrations which, if exceeded, mean that the food is judged
unfit for human consumption.
hFrom US Environmental Protection Agency (1989b); includes its metabolites, 3-(2,2-dichloro-
ethenyl)-2,2-dimethylcyclopropane carbxylic acid and (3-phenoxybenzyl)methanol

2. Studies of eancer In Humans

No data were available to the Working Group.

338 lARe MONOGRAPHS VOLUME 53

3. Studies of eancer in Experimental Animais

Oral administration

Mouse: Four groups of 70 male and 70 female Swiss-derived mice, four to five weeks old,
were fed 0, 250, 1000 or 2500 mg/kg of diet permethrin (cis:trans isomer, 40:60; ? 93.9%
pure) for 98 weeks. Survval in control and experimental groups was comparable; more than
75 % of animaIs survved beyond 52 weeks and 20% or more survived until the termination of
experiment. ln male mice, there was a slight increase in the incidence of pulmonaiy
adenomas: 11/70 control, 6/69 low dose, 13/70 mid dose and 17/70 high dose (p = 0.04 test
for trend) (Ishmael & Li tchfield, 1988).
Rat: Four groups of 60 male and 60 female pathogen-free Alpk:AP (Wistar-derived)
rats, aged four to five weeks, were fed 0, 500, 1000 or 2500 mg/kg of diet permethrin (cis:trans
isomer,40:60; ? 93.9% pure) for 104 weeks, at which time the experiment was terminated.
Survval in control and experimental groups was similar; more than 92% survived beyond 52
weeks and 42% or more survived until termination of the experiment. There was no
difference in the incidence of tumours between the control and experimental groups
(Ishmael & Litchfield, 1988).

4. Other relevant data

The toxicity of permethrin has been reviewed (FAO/WHO, 1980, 1982, 1988; WHO,
1990).

4.1 Absorption, distribution, metabolism and excretion

4.1.1 Humans
Ten scabies patients (five men and five women) had about 25 g (range, 21-32 g) of a 5%
permethrin cream applied to the skin of the whole body, with the exception of the head and
neck. Dermal absorption of permethrin was calculated from the quantity of conjugated and
nonconjugated cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic
acid (CVA) metabolites ofpermethrin determined in the urine. ln samples ofurine collected
by seven patients one and two days after application of the permethrin cream, 414 and 439 l1g
mean total CV A were found, respectively. The mean total CV A in the urine of three patients
who collected their urine in the same container for two days was 1435 Ilg. The urinaiy
concentration of trans-CV A varied during the first 48 h from 0.11 to 1.07 Ilg/ml and that of
the cis-isomer from 0.02 to 0.21 l1g/mL. CV A was still detectable in the urine of three patients
after a week and in the urine of one patient, reported to be an alcoholic, after two weeks. The
absorption of permethrin over the first 48 h after application was estimated from the urinaiy
CVA excretion levels to be 6 mg (range, 3-11 mg), i.e., 0.5% of the dose applied (van der
Rhee et al., 1989).
Among approximately 350 people who were individuallydusted against body lice with
30-50 g ofpowders containing 2.5 or 5.0 g/kg permethrin (cis:trans, 25:75), the mean amount
of permethrin absorbed during the first 24 h after treatment was estimated to be 14 Ilg/kg bw
 PERMETHRIN 339

among 19 of the subjects using the powder containing 2.5 g/kg permethrin and 39 J,g/kg bw
among 15 of the subjects using the 5 g/kg powder. No residue was found in samples of urine
taken 30 and 60 days after treatment (N assif et aL., 1980).
4.1.2 Experimental systems
Pyrethroids are absorbed through the skin and the respira tory and digestive tracts,
although absorption from the gastrointestinal tract appears to be incomplete. Pyrethroids
undergo metabolic degradation at numerous sites (Miyamoto, 1976). ln mammals, they are
generally metabolized through ester hydrolysis, oxidation and conjugation (WHO, 1990).
The metabolism of permethrin has been studied in great detail in various species of
mammals using isomers labelled in the aIcohol or acid moiety. The metabolic pathways of
permethrin in mammals are given in Figure 1 (WHO, 1990). It is metabolized and almost
completely eliminated from the body within approximately 12 days in rats, goats and cows
following oral administration; trans-permethrin is eliminated more rapidly than is cis-
permethrin, and trace tissue residue levels of the cis isomer were higher than those of the
t'ans isomer in these species (Elliot et al., 1976, Gaughan et al., i 977, i 978; lvie & Hunt,
1980). Absorption through the skin has been demonstrated in mice (Shah et al., 1981), rats
(Shah et aL., 1987; Sidon et al., 1988) and monkeys (Sidon et aL., 1988). Dermal absorption was
greater in rats than in monkeys (Sidon et aL., 1988). After an intramuscular injection of
14C-labelled permethrin, the urinary half-time values were similar for the cis and trans

isomers in rats and monkeys. Radiocarbon from trans-permethrin was excreted mostly in the
urine, whereas that from the cis-permethrin was eliminated in both urine and faeces (Sidon et
aL., 1988).

4.2 Toxic effects

4.2.1 Humans
Volunteers received applications to an area of 4 cm2 on an ear lobe of 0.05 ml of a
field-strength preparation of technical (94-96% active ingredients) or formulated (32-36%)
permethrin (0.13 mg/cm2) or of the inert ingredients; 0.05 ml of the vehicle (ethanol as the
control for technical permethrin and water as the control for formulated permethrin) was
applied to the other lobe. The intensity of paraesthesia induced by permethrin was four-fold
stronger than that induced bya similar application of fenvalerate, permethrin being the least
active compound for both the technical and formulated preparations. No cutaneous
sensation was elicited by the inert ingredients. Paraesthesia appeared after a latent period of
about 30 min, peaked between 8 and 12 h and disappeared after about 24 h. Further studies
using a range of doses demonstrated that the response was dose-related (Flannigan et al.,
1985).
Workers who handled seedlings treated wÍth permethrin (cis:trans, 25:75 wettable
powder or cis:trans, 40:60) reported irritation on the skin (63% of subjects) and in the upper
respiratory tract (33 %) (Kolmodin- Hedman et aL., 1982).
A group of 435 patients, most of them children, were treated for pediculosis capitis;
approximately half of the group were treated with a single, lü-min application of 25-50 ml of
a permethrin (1 %) and isopropanol (20%) cream rinse after towel dryng ofwashed hair, and
the remainder were treated with a liquid product containing pyrethrins (0.3 %), piperonyl
 V)
o.l

Fig. 1. Metabolic pathways of permethrin in mammalsa

Ci. X COOH',í 0 JS -- HOO ,í 0 JS 1-

HOCH,
~ OH L OHJ
Ci 2' -OH-Per 2' -OH-PBacid
sulfate

glycine

"¡X=".~o~~
Ci 4'-OH,trans-OH-Per glutamic aCi:Urlfate ;onjugate .
-
glucuronide
Ci .. COH,
~tiCI¡X ;§ O,( Ci~ . glucuronide
. ./~COOH
'=~og giirl=.~o~ Ci COOH -- taurine
~
~
taurine . Ci cis-Per 4' -OH-PBacid
trans-Cl2CA conjugate o
oz
trans - Per
. t Ci c/s-CI2CA
conjuga e

. HOH,c HOH,c
"): sulfate ., l
glucuronide Ci +-
;t Ci ,í ,('
COH COH, 0
con

j, t
J§0 ~AeOH
Ci~ J§ oJ§
HOH,C HOH,c
Ci,- V . glucuronide o
~
Ci Ci
trans-OH-cis-CI2CA
--HOH,c
4'-OH-PBalc
Ci COOH,
trans-OH-Per
Ci ~COOH
trans-OH-trans-CI2CA
"'
~
en
glucuronide "Ci~ X CH'O~cl, X CH,OH ;§o,( 6
~ COOH
Ci r COH,
Ci J PBalc
I~
""'~~!~ "~~"' 0 o,l_"~'""" - sulfate
B
~
cis-OH-cis-CI2CA l :- ~ . Ci COOH, J§ O)§ J Ci COOH
tr
CH, HOO
sulfate¥" V glucuronidc.. J§0J§ glucuronide cis-OH-Per cis-OH-trans-CI2CA VI

"¡X,) r'\
V)

\. "rl /'
" l CH"
Ci cis-OH-cis-CI2CA-lactone
glycine glutamic acid
Ci CO
conjugate conjugate cis-OH-trans-CI2CA -Iactone

Dfrom WHO (199); Per, pennethrin; C1iCA, chiysanthemic acid; PBacid, 3-phenoxybenzoic acid; PBalc, 3-phenoxybenzyl alcohol
 PERMETIRIN 341

butoxide (3%), petroleum distillate (1.2%) and benzyl alcohol (2.4%). Cutaneous
side-effects (pruritus, mild transient skin burning, stinging sensations, skin tingling, eryhema
and scalp rash) were reported by 7% of the patients in the first group and by 16% of those in
the second (DiN apoli et aL., 1988). Similar resul ts and side-effects were reported by
Brandenburg et al. (1986).
One of 28 subjects with pediculosis pubis treated with a 1 % permethrin rinse developed
miId scrotal eryhema and irritation 12 h after application (Kalter et al., 1987).
Of 10 scabies patients treated with one application of 25 g (range, 21-32 g) of a 5%
permethrin cream, followed by a thorough washing approximately 8-20 h after treatment, six
had limited, mild-to-moderate not pre-existing eczema on the scabies-affected skin at one or
more examinations (van der Rhee et al., 1989).

4.2.2 Experimental systems

Synthetic pyrethroids act on axons in the peripheral and central nervous system by
interacting with sodium channels in mammals and/or insects. The mechanism of toxicity of
synthetic pyrethroids and their classification into two tyes were reviewed by WHO (1990).
Permethrin does not contain an a:-cyano-group and is a tye 1 pyrethroid.
Oral LDsos in aqueous suspension generally ranged from approximately 3000 to
:; 4000 mg/kg bw, while the use of corn oil as the vehicle generally gave LDso values of about
500 mg/kg bw (WHO, 1990). cis-Permethrin is considerably more toxic th an trans-
permethrin when given oraIly to rats (in WHO, 1990) or intraperitoneally or intravenously to
mice (Glickman et al., 1982). After oral administration of 40:60 cis:trans permethrin to rats,
signs of poisoning became apparent after 2 h and persisted for up to three days; these
included whole-body tremors, sometimes accompanied by salivation. Other signs were
hyperactivity, hyperexcitability, urination, defaecation and ataxia (WHO, 1990).
ln several subacute and subchronic studies by oral administration of permethrin to mice,
rats and dogs, repeated findings were increases in absolute and relative liver weights,
proliferation of smooth endoplasmic reticulum and increased activity of microsomal
oxidative enzyes. ln 90-day studies in rats, increased absolute and relative liver weights
were reported to be evident with doses of 100 mg/kg of diet; in dogs, su ch effects were
reported to be apparent with doses of 50 mg/kg bw and upwards for 90 days. ln sorne but not
aIl studies, high doses of permethrin were reported to damage peripheral nerves in rats
(WHO, 1990). ln rats fed diets of 20, 100 or 500 ppm (mg/kg) permethrin (isomeric
composition unspecified) for two years or in rats from the third generation in a
three-generation study with dietary exposure to 20 or 100 ppm, however, there was no
evidence of morphological damage to nervous tissue when compared to control groups
(Dyck et al., 1984).
Long-term studies with rats and mice fed diets containing up to 2500 ppm (mg/kg)
permethrin (40:60 cis:trans) indicated effects on the central nervous system, such as tremors
and hypersensitivity to noise, in rats only and only during the first two weeks. Liver
hypertrophy, increased microsomal enzye activity and proliferation of smooth
endoplasmic reticulum occurred in both species but was less pronounced in mice (Ishmael &
Litchfield, 1988).
342 IARC MONOGRAPHS VOLUME 53

Permethrin (80:20 cis:trans) (50 mg/kg bw per day orally to rats) increased the levels of
cyochrome P450 in liver after four, eight or 12 days of administration and NADPH
cyochrome c reductase after eight or 12 days. A mixture containing less of the cis form (40:60
cis:trans) increased the levels of the two enzyes only after eight or 12 days of administration
(Carlson & Schoenig, 1980). Treatment of rats with 190 mg/kg bw permethrin (25:75 cis:trans
permethrin) intraperitoneally for three days decreased antipyrine half-time, and )'-glutamyl-
transpeptidase activity in plasma was significantly increased within 21 and 14 days at doses of
95 and 190 mg/kg bw per day, respectively (Anadon et al., 1988).
4.3 Reproductive and developmental effects
4.3.1 Humans
No data were available to the Working Group.
4.3.2 Experimental systems
Following immersion of fertile mallard eggs (30 per dose group) for 30 sec in an aqueous
solution of permethrin, the LCso for embryonic death was :? 40 lb/acre at 100 gal/acre (:? 45
kg/ha at 935 l/ha; more than 100 times the usual field application rate); no malformation was
observed in mallard chicks (Hoffman & Albers, 1984).
Sprague-Dawley rats, weighing 180-200 g, were treated with permethrin in water at
concentrations ranging from 500 to 4000 ppm (mg/l) or with drinking-water (control) on days
6-15 of gestation. At concentrations of 2500 ppm or more, the protein and glycogen content
of the placenta was reduced (actual weight not given). The resorption index was increased at
aIl doses, but there was no change in the number of live fetuses at day 20 of gestation in any
treatment group (Spencer & Berhane, 1982).

4.4 Genetic and related effects (see also Table 5 and Appendices 1 and 2)
4.4.1 Humans
No data were available to the Working Group.
4.4.2 Experimental systems
Several unpublished studies were cited in a recent review (WHO, 1990).
Permethrin did not induce mutation in either bacteria or cultured Chinese hamster V79
cells. It did not induce mutation or aneuploidy in Drosophila melanogaster, nor did it inhibit
gap-junctional intercellular communication in V79 cells.
(The Working Group noted that the studies by Páldy (1981) and by Hoellnger et al.
(1987) on rodent bone marrow in vivo could not be evaluated because of inadequacies in the
experimental design and reporting of the studies.)

5. Summary of Data Reported and Evaluation

5.1 Exposure
Permethrin is a highly active contact insecticide, which was first marketed in 1977. It is
used mainly on cotton and food crops. Other uses are in forestry and for public health
purposes, in public buildings, residences and aircraft.
Table 5. Genetic and related efTects of permethrin
Test system Resulta Doseb Reference
Without With
exogenous exogenous
metabolie metabolie
system system

SAO, Salmonella typhimurium TAloo, reverse mutation 490.~~ Bartseh et al. (1980)
SAO, Salmonella typhimurium TAloo, reverse mutation 2500.~~ Moriya et al. (1983)
SAO, Salmonella typhimurium TAloo, reverse mutation 150.~~ Pluijmen et al. (1984)
SAO, Salmonella typhimurium TAloo, reverse mutation (fluet. test) 10.~~ Pluijmen et al. (1984)
SAO, Salmonella typhimurium TAloo, reverse mutation 2730.~~ Pednekar et al. (1987) "'
Ln
SAO, Salmonella typhimurium TAloo, reverse mutation 300. ~~ Herrera & Laborda (1988) ~
SA4, Salmonella typhimurium TAI04, reverse mutation (spot test) 300. ~~ Herrera & Laborda (1988) ~
SAS, Salmonella typhimurium TA1535, reverse mutation 250.~~ Moriya et al. (1983) t'
SAS, Salmonella typhimurium TA1535, reverse mutation (spot test) 50.~~ Herrera & Laborda (1988) ~
SA7, Salmonella typhimurium TA1537, reverse mutation
SA7, Salmonella typhimurium TA1537, reverse mutation (spot test)
2500.~~
50.~~
Moriya et al. (1983)
Herrera & Laborda (1988)
-Z
~
SA8, Salmonella typhimurium TA1538, reverse mutation 2500.~~ Moriya et al. (1983)
SA8, Salmonella typhimurium TA1538, reverse mutation (spot test) 50.~~ Herrera & Laborda (1988)
SA9~' Salmonella typhimurium TA98, reverse mutation 490.~~ Bartseh et al. (1980)
SA9, Salmonella typhimurium TA98, reverse mutation 2500.~~ Moriya et al. (1983)
SA9, Salmonella typhimurium TA98, reverse mutation 150.~~ Pluijmen et al. (1984),
SA9, Salmonella typhimurium TA98, reverse mutation (fluet. test) 10.~~ Pluijmen et al. (1984)
SA9, Salmonella typhimurium TA98, reverse mutation 2730.~~ Pednekar et al. (1987)
SA9, Salmonella typhimurium TA98, reverse mutation 300. ~~ Herrera & Laborda (1988)
SAS, Salmonella typhimurium TA97a, reverse mutation 2730.~~ Pednekar et al. (1987)
SAS, Salmonella typhimurium TA97, reverse mutation 300. ~~ Herrera & Laborda (1988)
EC2, Escherichia coli WP2 ha, reverse mutation 250.~~ Moriya et al. (1983)

w
.t
w
 w
,t
,t

Table 5 (contd)
; -;i
Test system Resulta Doseb Reference
~
Without With ~
exogenous exogenous o
metabolic metabolic z
o
system system a
DMN, Drosophila melanogaster, chromosome loss o 5.~~ (feeding solution) Wooruff et al. (1983) ~
'"
DMX, Drosophila melanogaster, sex-linked recessive lethal mutation o 1.~~ (feeding solution) Gupta et al (199) :i
G90, Gene mutation, Chinese hamster V79 cells, ouabain resistance - oe 40.~~ Pluijmen et al. (1984) C/
G9H, Gene mutation, Chinese hamster V79 cells, hpn locus oe 40.~~ Pluijmen et al. (1984)
ICR, Inhibition of interceUular communication, V79 ceUs in vitro o 8.~~ Flodström et al. (1988)
d
E
a_, negative; 0, not tested ~
bln-vitro tests, iig/ml; in-vivo tests, mg/kg bw t'
VI
'Data obtained in the presence of an exogenous metabolic system were inadequate for an evaluation w
 PERMETHRIN 345

Permethrin has been formulated as granules, powders, emulsifiable concentrates,

aerosols and other forms.
Exposure can occur during its production and application and, at much lower levels,
from consumption of food containing residues.
5.2 Carcinogenicity data in humans
No data were available to the Working Group.

5.3 Carcinogenicity in experimental animaIs

One preparation of permethrin (cis:trans, 40:60) was tested for carcinogenicity in one
study in mice and in one study in rats by oral administration in the diet. ln mice, a marginal
increase in the incidence of pulmonary adenomas was observed in males. No increased
tumour incidence was observed in treated rats.
5.4 Other relevant data
Permethrin ha~ caused dermal irritation after topical exposure. It induced microsomal
enzyes in rats and mice.
No data were available on the genetic and related effects of permethrin in humans. No
effect was observed in the limited number of short-term tests available.
5.5 Evaluation 1

No data were available from studies in humans.

There is inadequate evidence for the carcinogenicity of permethrin in experimental
animaIs.
Overall evaluation
Permethrin is not classifiable as to its carcinogenicity to humans (Group 3).

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346 IARC MONOGRAPHS VOLUME 53

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 PERMETHRIN 347

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348 IARC MONOGRAPHS VOLUME 53

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