United Stttw Offle* of P*tMdm «nd Toxte Subcunon
En»lronnxnul Protection Offie* of P«»Wd« Progrimt (TS-766CI
Agency WMhtngton, OC 20460
&EPA Pesticide
Fact Sheet
Name of Chemical: ALLETHRIN STEREOISOMERS
Reason for Issuance: REGISTRATION STANDARD
Date Issued: March 24 . 1988
Fact"Sheet Number: 158
1. DESCRIPTION OF CHEMICALS
The following chemicals are all synthetic pyrethroid insecticides. That is,
they are synthetic duplicates of a component of pyrethrum which is extracted
from chrysanthemum flowers. Introduced in 1949, Al'le^hrin was the first
synthetic pyrethroid. Bioallethrin and S-bioallethrin were introduced in
1969 and 1972, respectively
A. Connon Name: Allethrin
Generic Name: (2-methyl-l-prcpenyl) - 2-methyl-4-oxo-3-
(2 propenyl)-2-cyclo-penten-l-yl ester or mixture
of cis and trans isomers-
Trade Name: Pynamin
EPA Shaughnessy code: 004001 and 004002 (allethrin coil)
Chemical Abstracts Service (CAS) Number: 584-79-2
Producers: McLaughlin Gormley King
Sumitjorro Chemical Company
Fairfield American
B. Connon Name: d-trans Allethrin, Bioallethrin
Generic Name: d-trans-chrysanthemum monocarboxylic
ester of d l-2-allyl-4-hydroxy-3-
methyl-2-cyclo-penten-l-one
Trade Name: Bioallethrin
EPA Shaughnessy Code: 004003
Chemical Abstracts Service (CAS) Number: 584-79-2
Producers: McLaughlin Gormley King
Roussel Uclaf
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C. Comtr n Name: S-bioallethrifl; Esbiol
Generic Name: d-trans-duysanthenum nonocarbDxylic
acid ester of d-2-allyl—4—hydrOxy-3-
nethyl—2-yclcpenten—1—one
Trade Name: Esbiol
EPA Shaughnessy Code: 004004
Chemical Al tracts Service (CAS) Numbar: 23434-00-6
Producers: t4taughlin Gormley King
Ronssel Uclaf
D. Canton Name: D—cis/trans allethrin; Pynamin Forte
Generic Name: dl-3-allyl-2-rrethyl-4 -c”aD-2-cYC lopenteriyl
d-cis/trans chrysanthenate
Trade Name: Pynaxnin Forte
EPA iaughnessy Code: 004005
Chemical A tracts Service (CAS) Number: 42534—61-2
Producers: SUIfl1tOIfl D Chemical Co., Ltd.
2. USE PM’IERNS AND FOP 4JLATIC 4S
Application Sites: Broad spectrum insecticides ani acaricides registered
for use cx i terrestrial food crops (vegetables,
citrus fruits, ar i orthar crops); terrestrial
ixrifood uses (ornamental plants, turf, recreational
areas, an forest trees); greenhouse food a
naifood crops (ornamentals ar vegetables);
ir oor an i wtdoor dcxtestic d llings; postharvest
use on fruit, vegetables ar grains, ar stored
food; can rcial ar ir ustrial uses (food har llng
establishments).
‘pes of Fornulations: Pressurized liquids, itosquito coils, dusts,
enusifiable concentrates, soluble oxicentrate
liquids, arxi ready-to-use liquids. Almost
always fornulated with a synergist ar 1 one or
more additional active ingredients.
Predctninant uses an
Methods of Application:
Prinarily ir 3.oor ar c*itdoor use aixind the Ixxte
as foggers, plant, carpet ani general pirpose
aerosols, arx mosquito coils to control mon
pests including, bit r ot limited to, ants, bedixigs,
carpet beetles, codcroadtes, fleas, ticks, moths,
wasps and bees. Applied to crops fo]iarly by aerial
or grcund equipment. Postharvest applications nade
as an enulsi”e dip.
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3. SCIE1ICE FINDThXS
SunvBry Science Staten nt
The Agencj has very little acceptable toxicity data for the allethrin
stereoisOflerS. There are r data available to assess the envircnfl ntal
fate diaracteristiCS of these conpounds, including their potential
to cxntarninate ground water. There are ecological effects data
whidt sh i that the stereoison rS are highly toxic to fish and aquatic
invertetrates • and essentially non-toxic to avian species. There
are no acceptable residue data available to assess the adequacy of
the current tolerances for allethrin.
Qiemical tharacteristics of the Tedinical Material
Physical State: Viscous oil; liquid, clear oil
Color: Pale yel] , yellow-orange, slightly brownish
Odor: Mild to slightly ajx i ic
r.blecilar weight and enpirical fornula: 302 - C 1 gH O3
Solubility: Insoluble in water; miscible with petroleum oils,
and soluble in paraffinic and araTatic hydroa rb)flS
Toxicology tharacteristics
Acute toxicity : The acute oral toxicity of bioallethrin and
and s-bioallethrin is low to noderate. Adequate data to discern
other acute effects of these cciipounds are not available.
Subcthronic toxicity : In a 90-day feeding study on bioallethri-n,
rats were a:lniinistered 0, 500, 1500, 5000, and 10,000 ppm bioallethrin
in the diet. A rio observed-effectlevel ( oEL) ‘ s established at
1500 ppm lased upon a decrease in lxdy weight in and increased
levels of serum liver euzynes in fenales and increased liver weights
in x th sews. This study, however, is presently classified as
only supplen ntaxy, txzt nay be upgraded upon sutmission of additional
inforiTation.
thronic toxicity : In a 6-ncnth oral feeding study using beagle dogs,
the arujiuls were administered 0, 200, 1000, and 5000 ppm bioallethrin
in the diet. The NDEL was determined to be 200 ppm tased on
effects on the liver.
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One rodent chronic feeding/CflCOgefliCity study is available for
d—cis/tranS allethrin. tn this study, rats were fed 0, 125, 500,
and 2000 wm of the test su tanCe in the diet for 2 years. No
oncogenic effects were otserved. For systemic toxicity, the L
was determined to be 125 rn based on decL eased body weight- gain
and the presence of liver effect—s.
TeratogenicitY One teratology study conducted with bioallethri.n is
available. In this study, rats were dosed with 50, 125, and 195
nq/kg/day bioallethrin in the diet. The test catipound did not induce
develcprrefltal effects at the dose levels tested.
Mutagenicity : T D iTutagenicity studies (W dannge and reverse nutation)
conducted with bioallethrin are negative for genetic daziage.
EflV]xct msfltal Fate Characteristics
No data on the allethrin stereoiscnerS are available to
assess the envircrurental fate and transport, and the potential
exposure of hunans and ncrLtarget organisms. The potential of
these xitpounds to a.,ntaxninate ground water is unknc,’m. Because
the allethrins are t ught to degrade rapidly in the environment,
envircx tental fate data are beiog reiuired on a “tiered” basis.
This approach will permit the Agency to n ke a preliminary assessment
of the persistence of these cxxiipouzxls. The reiuir nt for additional
testing will be deferred until evaluation of all data sutnitted under
Tier I.
Ecological Characteristics
Avian Acute Oral Toxicity:
Species Stereoisorrer LD 50 or LC p
Mallard Duck Technical allethrin >2000 ng/kg
Mallard Duck D-cis/trans allethrin 5620 m
Bob.fnite Quail Bioallethrin 2030 pm
Bot ite Quail D-cis/trans allethrin 5620 m
These data s1 i that the allethrins are practically nontoxic to
birds on both an acute and subacute exposure basis.
Freshwater Fish Acute Toxicity : Twenty-seven toxicity tests conducted with
co1 ter and warni ter fish species indicate that the allethrins are
highly toxic to fish. LC 5 values ranged fran 2.6 ppb (o.* o sairron —
bioallethrin) t- 80 b (fathead minna ii — S-bioallethrin).
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Toxicity to Pquat ic Invertebrates : Data show that allethrin is
highly toxic to aquatic invertebrates With LC5o values of 5.6 ppb
for st ef lies and 56 ppb for blackf lies.
Toxicity to Non-target InseCts : Although technical a 1 lethrin is node rately
toxic to honey bees, the outdoor app licat-ion rates are so low that
even a direct application to bees is not likely to result in signif i-cant
nortality.
Tolerance Assessn flt
The available data revie ied are insufficient to evaluate the adequacy
of the established tolerances (covering postharvest use) for residues
of allethrin in or on food/feed iten (40 CFR 180.113). Allethrin is
the only stereoiSon r with established tolerances.
Because of insufficient residue chemistry arxl toxicity data for all of the
allethrin stereoisaters, the Agency is unable to calculate an acceptable
daily intake under the Tolerance Assessitent System.
There are no Canadian or Mexican tolerances or Codex Maxinum Residue
Limits for residues of the allethrins in or on any plant ccitucdity.
Therefore, no ccxi atibilitY questions exist.
4. RD JIRE]) UNI JE L BELThK
The Registration Standard for the allethrins contains no unique
labeling requirements. It requires only updated environn ntal
precautionary and disposal statenents and a statenent for outdoor
use products that the product is highly toxic to fish.
5. SU!+ RY OF B X3 JLA IORY POSITIONS AND I ATIONALES
°The Agency is not starting a special review the allethrths.
°Since EPA believes that the allethrins nay degrade rapidly
in the environnent, the Agency is requiring environnental fate
data on a tiered tasis. Additional data nay be required upon
evaluation of the tier I studies.
°The Agency is permitting registrants to use the technical
prxxluct Esbiothrin as a respresentative test naterial for
chronic studies on Bioallethrin and S-bioallethrin since it is
a mixture of the t cxzrpounds , and they are of similar toxicity.
Separate chronic studies are beir required for Allethrth and
D-cis/trans allethrin.
°The Agency is not requiring arty endangered species restrictions
since there is no evidence that the allethrins pose a hazard to
endangered species fran daies tic indoor/outdOOr uses.
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°The Agency is not r uiring arT)’ grciind water advisory labeling, or reentty,
spray drift, or protective clothing restrictions at this tine.
°The Agency is not inposing restricted use classification on the allethrins.
°While the r uired data are under develqnent all currently registered
productS containing the allethrins ney be sold, disi-rituted, fonrulated
and used, provided that they are in ccupliance with all other t.eiiT
specified in the Registration Standard.
6. SU? 1 f OF W JOR DATA GAPS
‘ 1\)xcoloqy
Acute Toxicity :
Acute oral LD toxicity (Allethrin, Pynamin-forte)
Acute denial W 50 toxicity (Allethrin, Pynamin- forte,
S—bioal lethrin, Bioallethrin)
Acute inhalation LC ,j Toxicity (all allethrins)
Eye irritation (all allethrins except Esbiothriri)
Dernal irritation (all allethrins except Esbiothrin)
Dernal serisitiz tiofl (all allethriris)
Subchrcxiic Toxicity -
90-day feeding
Rodent (all allethrins except Pynamin-forte)
Nonrodent (all allethrins except Bioallethrin)
21-day denial (all allethrins)
90-day inhalation (reserved for all allethrins)
thronic Toxicity
Rodent feeding (all allethrins except Pynantin-forte)
Nonrodent feeding (all allethrins except Bioallethrin)
Rat oncx’genicity (all allethrins except Pynaxuiri-forte)
tk se cnCOgerLCLty (all allethrins)
Rat teratogenicity (all allethrins except Bioallethr in)
Rabbit teratogenicity (all allethrins)
Reproduction (all allethrins)
Mutagenicity
Gene niitat .ion (Allethrin, Pynainin-forte, S-bioallet.hrin)
ChrcxnDscval aberration (all allethrins)
Other nedianisne of nutageriicity (all allethrins except
Bioallethrifl)
Special Testing
Metatolism (all allethrins)
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Ecx)logical Effects
Avian r roduction
Field testing - neimals ani birds (reserved periJing
reproiuct.iofl da’a)
Frest ,ater fish LCso (typi l EE’)
FresI ater aquatic invertebrate T I25O ( w al EP)
Acute es+uarlne ani narine LC5O (fish, shrinp, oyster)
Fish early life stage and invertebrate life cycle
(freshiater, estuarine)
Fish life cycle
Field testing (aquatic organisn )
Environnental Fate
TIER I
c x3RADATIa SIUDIES — LAB
Hydrolysis
Photodegradation - water, soil, an5 air
M ABDLISM SIUDIES - LAB
Aerobic netabolism (soil ar aquatic)
Anaerobic netabDLism in soil
MJBILflY SIUDIES
Leaching/aged leaching
Volatility (jab)
- Reserved
— Reserved
— Reserved
- Reserved
— Reserved
— Reserved
— Reserved
irrigated crops - Reserved
fish - Reserved
aquatic nontarget
- Reserved
— Reserved
— Reserved
— Reserved
TIER II
Anaerobic aquatic netabolism
Volatility (field)
Field dissipation (soil)
Field dissipation (aquatic, sedinent)
Field dissipation (soil, long—term)
Acomulation studies on rotational
crops (cxxifined)
Acamulation studies
crops (field)
Acxunulation studies on
Accunulation studies in
Accunulation studies in
organisns
Reentty
Spray drift
Exposure
on rotational
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Product Chemistry
Product Identity and Ccxt x itiori
Analysis and Certification of Product Ingredients
Physical and Chemical Characteristics
Residue Chemistry
Nati e of the Residue (Mei-abDlism) in PLant and
Livestock
Residue Analytical Met ds (nay be r uired if
additional netabolit es of toxicological icern are
identified)
Stability Data
Magnitude of Residue
Crq) field tri;:d
Postharvest treatn nt of fruits and vegetables
Stored oointodities
Processing stu ii es
Meat/miik/pxi ltry/egs
Food handling
7. o ff Cr PE1 0N AT EPA
Phillip 0. Hutton
Product t nager 17
Registration Division (TS-767C)
Office of Pesticide Progran
Envirormental Protection Agency
401 M Street, S. W.
Washington, D. C. 20460
(703) 557—2600
DISCLAIMER: The Infornation presented in this Chemical Infornation Fact
Sheet is for infornational purposes only and nay r t be used
to fulfill data re uir Tents for pesticide registration and
reregistration.
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