IPCS INTERNATIONAL PROGRAMME ON CHEMICAL SAFETY
Health and Safety Guide No. 25
RESMETHRINS
HEALTH AND SAFETY GUIDE
Resmethrin Bioresmethrin Cismethrin
UNITED NATIONS ENVIRONMENT PROGRAMME
INTERNATIONAL LABOUR ORGANISATION
WORLD HEALTH ORGANIZATION
WORLD HEALTH ORGANIZATION, GENEVA
This is a companion volume to Environmental Health Criteria 92:
Resmethrins
Published by the World Health Organization for the International
Programme on Chemical Safety (a collaborative programme of the United
Nations Environment Programme, the International Labour Organisation,
and the World Health Organization)
This report contains the collective views of an international group of
experts and does not necessarily represent the decisions or the stated
policy of the United Nations Environment Programme, the International
Labour Organisation, or the World Health Organization.
ISBN 92 4 154346 9
ISSN 0259 - 7268
(c) World Health Organization 1989
Publications of the World Health Organization enjoy copyright
protection in accordance with the provisions of Protocol 2 of the
Universal Copyright Convention. For rights of reproduction or
translation of WHO publications, in part or in toto, application
should be made to the Office of Publications, World Health
Organization, Geneva, Switzerland. The World Health Organization
welcomes such applications.
The designations employed and the presentation of the material in this
publication do not imply the expression of any opinion whatsoever on
the part of the Secretariat of the World Health Organization
concerning the legal status of any country, territory, city or area or
of its authorities, or concerning the delimitation of its frontiers or
boundaries.
The mention of specific companies or of certain manufacturers'
products does not imply that they are endorsed or recommended by the
World Health Organization in preference to others of a similar nature
that are not mentioned. Errors and omissions excepted, the names of
proprietary products are distinguished by initial capital letters.
CONTENTS
INTRODUCTION
1. PRODUCT IDENTITY AND USES
1.1. Identity
1.2. Physical and chemical properties
1.3. Analytical methods
1.4. Production and uses
2. SUMMARY AND EVALUATION
2.1. Human exposure to resmethrins
2.2. Uptake, metabolism, and excretion
2.3. Evaluation of effects on the environment
2.4. Effects on experimental animals and in vitro test systems
2.5. Effects on human beings
3. CONCLUSIONS AND RECOMMENDATIONS
3.1. Conclusions
3.2. Recommendations
4. HUMAN HEALTH HAZARDS, PREVENTION AND PROTECTION, EMERGENCY ACTION
4.1. Main human health hazards, prevention and protection,
first aid
4.1.1. Advice to physicians
4.1.2. Health surveillance advice
4.2. Explosion and fire hazards
4.3. Storage
4.4. Transport
4.5. Spillage and disposal
4.5.1. Spillage
4.5.2. Disposal
5. HAZARDS FOR THE ENVIRONMENT AND THEIR PREVENTION
6. INTERNATIONAL CHEMICAL SAFETY CARD
7. CURRENT REGULATIONS, GUIDELINES, AND STANDARDS
7.1. Previous evaluations by international bodies
7.2. Exposure limit values
7.3. Specific restrictions
7.4. Labelling, packaging, and transport
7.5. Waste disposal
BIBLIOGRAPHY
INTRODUCTION
The Environmental Health Criteria (EHC) documents produced by the
International Programme on Chemical Safety include an assessment of
the effects on the environment and on human health of exposure to a
chemical or combination of chemicals, or physical or biological
agents. They also provide guidelines for setting exposure limits.
The purpose of a Health and Safety Guide is to facilitate the
application of these guidelines in national chemical safety
programmes. The first three sections of a Health and Safety Guide
highlight the relevant technical information in the corresponding EHC.
Section 4 includes advice on preventive and protective measures and
emergency action; health workers should be thoroughly familiar with
the medical information to ensure that they can act efficiently in an
emergency. Within the Guide is an International Chemical Safety Card
which should be readily available, and should be clearly explained, to
all who could come into contact with the chemical. The section on
regulatory information has been extracted from the legal file of the
International Register of Potentially Toxic Chemicals (IRPTC) and from
other United Nations sources.
The target readership includes occupational health services, those in
ministries, governmental agencies, industry, and trade unions who are
involved in the safe use of chemicals and the avoidance of
environmental health hazards, and those wanting more information on
this topic. An attempt has been made to use only terms that will be
familiar to the intended user. However, sections 1 and 2 inevitably
contain some technical terms. A bibliography has been included for
readers who require further background information.
Revision of the information in this Guide will take place in due
course, and the eventual aim is to use standardized terminology.
Comments on any difficulties encountered in using the Guide would be
very helpful and should be addressed to:
The Manager
International Programme on Chemical Safety
Division of Environmental Health
World Health Organization
1211 Geneva 27
Switzerland
THE INFORMATION IN THIS GUIDE SHOULD BE CONSIDERED AS A STARTING POINT
TO A COMPREHENSIVE HEALTH AND SAFETY PROGRAMME
1. PRODUCT IDENTITY AND USES
1.1 Identity
Resmethrin is an ester of chrysanthemic acid and
5-benzyl-3-furylmethyl alcohol. It is a racemic mixture of 4 optical
isomers: [1R, trans]-, [1R, cis]-, [1S, trans]-, and [1S, cis]-isomer.
In technical products the ratio of these isomers is roughly 4:1:4:1.
The [1R, trans]-isomer is called bioresmethrin and the [1R, cis]-
isomer, cismethrin. Among the isomers, the [1R, trans]-isomer has the
highest insecticidal activity, followed by the [1R, cis]-isomer.
Molecular formula: C22H26O3
Chemical formula:
1.2 Physical and Chemical Properties
The physical and chemical properties of resmethrin and its selected
isomers are given in the International Chemical Safety Card on pages
20-23.
1.3 Analytical Methods
The determination of residues and of environmental samples can be
carried out using high performance liquid chromatography with a UV
detector (206 nm) at levels as low as 0.05 mg/kg. Gas chromatography
with a flame-ionization detector is used for the analysis of technical
products.
1.4 Production and Uses
It is estimated that 20-30 tonnes of resmethrin are produced and used
each year. It is mainly used for the control of insects that are of
importance in public health and in the home, but it is also used on
stored grain and for the control of whitefly in greenhouses.
It is formulated as an aerosol, an oil formulation, or an emulsifiable
concentrate, sometimes in combination with other insecticides and/or
synergists.
2. SUMMARY AND EVALUATION
2.1 Human Exposure to Resmethrins
Human exposure to the resmethrins is mainly via inhalation when the
formulations are sprayed in the form of a mist. Air levels following
conventional household aerosol spraying are not expected to exceed
0.5mg/m3.
The only significant potential dietary exposure is following the use
of resmethrin on stored grain. Residues of up to 4 mg/kg might be
present in grain, but this would be reduced to zero in white bread.
However, reduced residues may be present in wholemeal bread. A food
additive tolerance has been established by the US Environmental
Protection Agency (US EPA) permitting resmethrin residues of up to
3 mg/kg in or on food commodities resulting from the use of the compound
in food handling areas. An ADI of 0.1250 mg/kg body weight per day
was established by the US EPA on the basis of the
no-observed-adverse-effect levels observed in long-term toxicity
studies on experimental animals. No data are available on
occupational exposure to the resmethrins.
2.2 Uptake, Metabolism, and Excretion
When 14C-(alcohollabelled)-[1RS, trans]-resmethrin was administered
orally to rats at a rate of 500 mg/kg body weight, the radiocarbon was
eliminated slowly in the urine (36%) and faeces (64%) within 3 weeks.
More than 50% of the 14C was secreted into bile during 72 h and
circulated enterohepatically. The major metabolic reactions were
ester cleavage, oxidation at the trans-methyl of the isobutenyl
group to alcohol, aldehyde, and carboxylic acid, oxidation at the 4'-,
alpha, and 4-positions of 5-benzyl-3-furylmethyl alcohol (BFA), and
conjugation.
Rats fed 14C-(acid or alcohol labelled) bioresmethrin or cismethrin
at a rate of 1 mg/kg excreted 5-benzyl-3-furancarboxylic acid (BFCA),
4'-hydroxy-BFCA, and alpha-hydroxy-BFCA together with
2- trans-hydroxymethyl- and 2-carboxyl derivatives of chrysanthemic
acid (CA). Derivatives of cis/trans-isomerized CA were also found.
The residual metabolites in the body were derived from the alcohol
moiety of bioresmethrin.
2.3 Evaluation of Effects on the Environment
Resmethrin is rapidly photodegraded. In sunlight, aqueous solutions
have a half-life of 47 min (pure water) and 20 min (sea water). A
range of photoproducts are formed from ester cleavage and oxidation
reactions.
Resmethrin is also very rapidly degraded in soil so that less than 2%
of the applied parent compound remains after 16 days. Complete
mineralization to carbon dioxide is a very important degradation
process (38% after 16 days). Under outdoor conditions, rapid
photodegradation and microbial degradation in the soil ensure that
residues will not persist to any extent in the environment.
In laboratory studies, resmethrins are very toxic for fish (96-h
LC50 values: 0.3-5.5 µg/litre) but less toxic for Daphnia and
aquatic insect larvae. However, under field conditions, the effects
are considerably less than might be predicted from the laboratory
studies because of the low water solubility of the resmethrins and
their ready degradation.
The toxicity of the resmethrins for birds is low (LD50 >
5000 mg/kg) and they do not produce any effects on avian reproduction.
2.4 Effects on Experimental Animals and In Vitro Test Systems
The acute toxicities of resmethrin and bioresmethrin in experimental
animals, by various routes of exposure, were low - oral LD50s of
resmethrin ranging from 690 mg/kg in the mouse to >5000 mg/kg in the
rat. Acute oral LD50s of bioresmethrin were 225 mg/kg in the
rabbit, and 10000mg/kg in the mouse. Cismethrin was moderately toxic
in the mouse, oral LD50s ranging from 152 to 160 mg/kg. The acute
toxicities of resmethrin metabolites were in the same range in the
rat, but somewhat higher in the mouse. The symptoms of poisoning were
characterized by tremors, hyperactivity, and convulsions (T-syndrome).
Resmethrin belongs to the Type I pyrethroid group.
While technical grade resmethrin is a slight skin irritant, it is not
a sensitizer.
In a 90-day rat study, a no-observed-adverse-effect level of 66 mg/kg
diet per day was established for resmethrin, whereas in another 2-year
rat study the lowest effect level appeared to be 500 mg/kg of diet,
corresponding to 25 mg/kg body weight per day. In a 6-month feeding
study on dogs, the no-observed-adverse-effect level was 10 mg/kg body
weight per day.
In a 90-day rat inhalation study, a no-observed-adverse-effect level
of 0.1g resmethrin/m3 was established.
The no-observed-adverse-effect levels for bioresmethrin were 400 mg/kg
in a 91-day dietary study in rats, corresponding to 33 mg/kg body
weight per day, and 80 mg/kg body weight per day in a 90-day study in
dogs.
The no-observed-adverse-effect level for (1R),-( trans. cis)-resmethrin
in a 24-week dietary study on the rat was 1500 mg/kg diet,
corresponding to 78mg/kg body weight per day.
Resmethrins are not mutagenic in a variety of test systems, including
gene mutations, DNA damage, DNA repair, and chromosomal effects.
Resmethrin was not carcinogenic in the mouse or the rat when fed at
dietary levels of up to 1000 mg/kg for 85 weeks and 5000 mg/kg for 112
weeks, respectively.
Resmethrin was not teratogenic in the rat, mouse, or rabbit at dose
levels up to 100 mg/kg body weight.
A dose of 40 mg resmethrin/kg body weight appeared to be the
no-observed-adverse-effect level for fetotoxicity in the rat.
In a 3-generation reproduction study on rats, a decrease in pup
weights and a slight increase in the number of dead pups were observed
at the 500 mg resmethrin/kg level.
2.5 Effects on Human Beings
Although the resmethrins have been used for many years, no data have
been reported on human toxicity. Thus, extrapolation data from
experimental animal and in vitro studies must be used to determine the
potential toxicity for human beings.
3. CONCLUSIONS AND RECOMMENDATIONS
3.1 Conclusions
(a) General population
Under recommended conditions of household and other public health use,
exposure of the general population to resmethrins is negligible and is
unlikely to present a hazard. Under conditions recommended for use in
food-handling and storage areas, as well as for post-harvest
treatment, the exposure of the general population to resmethrins in
the diet is unlikely to exceed the ADI established by the US EPA.
(b) Occupational exposure
With reasonable work practices, hygiene measures, and safety
precautions, the use of resmethrins is unlikely to present a hazard
for those occupationally exposed to it.
(c) Environment
At recommended application rates, it is unlikely that resmethrins or
the degradation products will reach levels of environmental
significance. In spite of its high toxicity for fish, a problem is
likely to occur only in the case of spillage or overspraying.
3.2 Recommendations
The label for the household use of resmethrins should include adequate
instructions for use and storage and, where appropriate, a warning of
flammability.
4. HUMAN HEALTH HAZARDS, PREVENTION AND PROTECTION, EMERGENCY ACTION
4.1 Main Human Health Hazards, Prevention and Protection, First Aid
Resmethrin is a synthetic pyrethroid insecticide. No cases of
poisoning have been reported in the general population or through
occupational exposure. The results of experimental animal studies
suggest that, following massive overexposure or accidental ingestion,
neurological symptoms, such as tremors and convulsions, could occur.
The human health hazards associated with certain types of exposure to
resmethrin, together with preventive and protective measures and first
aid recommendations are listed on the International Chemical Safety
Card on pages 20-23.
4.1.1 Advice to physicians
No specific antidote is known. Treat symptomatically. The main
hazard with liquid formulations is aspiration of the solvent into the
lungs, resulting in chemical pneumonitis.
4.1.2 Health surveillance advice
Pre-exposure and annual general medical examinations should be carried
out on workers regularly exposed to resmethrins.
4.2 Explosion and Fire Hazards
Some solvents in pyrethroid formulations are highly flammable. Use
dry powder, carbon dioxide, alcohol-resistant foam, sand. or earth for
dealing with fires. DO NOT use water. Cool nearby drums with water
spray.
If pyrethroid products are involved in a major fire, or in a fire
involving other products, advise the fire service that protective
clothing and breathing apparatus should be worn. Also, warn the
authorities that pyrethroids are highly toxic for fish, and that the
use of water should be confined to the cooling of unaffected stock,
thus avoiding the accumulation of polluted run-off from the site.
4.3 Storage
Store technical material and formulations away from heat, under lock
and key, and out of reach of children, animals, and unauthorized
personnel. Store in an area designated for insecticide storage,
preferably without drains.
Store away from foodstuffs and animal feed.
4.4 Transport
Pyrethroids are classified as "harmful" or "low hazard" for transport
purposes. Formulations based on flammable solvents may be subject to
local transport controls. Before dispatch, ensure that containers are
sound and that labels are securely fixed and undamaged. Comply with
local transport regulations.
Do not load together with foodstuffs or feed.
Accident procedures
- Avoid exposure, if possible by the use of appropriate protective
clothing and masks. Keep spectators away from the leaking or
spilled product and prevent smoking or the use of naked flames in
the immediate vicinity.
- Extinguish fires with dry powder, carbon dioxide,
alcohol-resistant foam, sand, or earth.
- Prevent liquid from spreading to other cargo, vegetation, or
waterways by containing it with a barrier made of the most
readily available material, e.g., earth or sand.
- Absorb spilled liquid and cover contaminated areas with earth,
lime, sand, or other absorbent material and place in a secure
container for subsequent safe disposal.
4.5 Spillage and Disposal
4.5.1 Spillage
Avoid exposure, if possible by the use of appropriate protective
clothing and masks.
Empty any product remaining in damaged or leaking containers into a
clean empty drum, and label.
Absorb spillage with lime, damp sawdust, sand, or earth and dispose of
safely (see below). If spillage is large, contain it by building a
barrier of earth or sandbags.
Decontaminate empty, damaged, or leaking containers with a 10% sodium
carbonate solution added at the rate of at least 1 litre per 20-litre
drum. Puncture containers to prevent re-use.
4.5.2 Disposal
Waste containing resmethrin should be burnt in a proper
high-temperature incinerator with effluent scrubbing. Where no
incinerator is available, contaminated absorbents or surplus products
should be decomposed by hydrolysis at pH 12 or above. Contact with a
suitable hydrolysing agent is required to ensure degradation of the
active ingredient to a safe level.
For emulsifiable material: 5% sodium hydroxide (caustic soda)
solution or saturated (7-10%) sodium carbonate (washing soda) solution
can be used.
For non-emulsifiable material: use a 1:1 mixture (by volume) of
either of the above solutions and a water/oil soluble solvent, such as
denatured alcohol, monoethylene glycol, hexylene glycol, or
isopropanol.
Cover the material with the hydrolysing agent and put aside to stand
for 7 days. Before disposal of the resultant waste, the material must
be analysed to ensure that the active ingredient has been degraded to
a safe level.
Never pour untreated waste or surplus products into public sewers or
anywhere where there is any danger of run-off or seepage into streams,
watercourses, open waterways, ditches, fields with drainage systems,
or the catchment areas of boreholes, wells, springs, or ponds.
5. HAZARDS FOR THE ENVIRONMENT AND THEIR PREVENTION
With recommended techniques and rates of application, it is unlikely
that resmethrin and its degradation products will reach levels of
environmental significance. Resmethrin is very toxic for fish and
honeybees, but, because of the the very low exposure levels that
normally occur, this is likely to cause a problem only in the case of
spillage.
Avoid spraying over bodies of water. Do not contaminate ponds,
waterways, or ditches with the product or used containers.
6. INTERNATIONAL CHEMICAL SAFETY CARD
This card should be easily available to all health workers concerned
with, and users of, resmethrins. It should be displayed at, or near,
entrances to areas where there is potential exposure to quintozene,
and on processing equipment and containers. The card should be
translated into the appropriate language(s). All persons potentially
exposed to the chemical should also have the instructions on the
chemical safety card clearly explained.
Space is available on the card for insertion of the National
Occupational Exposure Limit, the address and telephone number of the
National Poison Control Centre, and for local trade names.
RESMETHRIN
CAS chemical name: [5-(phenylmethyl)-3-furanyl]methyl-2,2-dimethyl-
3-(2-methyl-1-propenyl)-cyclopropanecarboxylate
Chemical formula: C22H26O3
CAS registry no.: 10453-86-8: RTECS registry no.: GZ1310000
PHYSICAL PROPERTIES OTHER CHARACTERISTICS
Resmethrin Bioresmethrin Cismethrin
Physical state waxy solid viscous oil - Resmethrin is a mixture of 4 stereo-isomers;
bioresmethrin is the [1R,trans]-isomer
Colour colourless practically - and cismethrin is the [1R-cis]-isomer;
colourless resmethrin is decomposed rapidly
on exposure to air or light and in
Odour chrysanthemate - - alkaline media; it is a synthetic pyrethroid
mainly used for household purposes and
Relative molecular mass 338.48 338.48 338.48 in stables
Melting point (°C) 43-48 30-35 -
Boiling point (°C) 180 180 -
(0.01 mmHg) (0.01 mmHg)
Water solubility (30°C) 1 mg/litre <0.3 mg/litre -
Solubility in organic solublea soluble soluble
solvents
Density (20°C) 1.050 1.050 -
Vapour pressure (mmHg) 1.1 × 10-8 1.4 × 10-4 -
(30°C) (25°C)
n-Octanol/water 2.9 × 103 6.2 × 104 -
partition coefficient
a Methanol (81 g/kg), hexane (220g/kg), xylene (1 kg/kg), kerosene (10%), isopropanol, methylene chloride.
HAZARDS/SYMPTOMS PREVENTION AND PROTECTION FIRST AID
SKIN: irritating to skin Proper application technique, Remove contaminated clothing; wash skin
proper skin protectionwith water and soap
EYES: irritating to eyes Face shield; goggles Flush immediately with clean water for at
least 15 minutes
INHALATION: irritant to Avoid inhalation of fine dust and Fresh air
respiratory system mist
INGESTION: unlikely occupational Do not eat, drink, or smoke during -
hazard working hours; wash hands before
eating, drinking, or smoking
Accidental or deliberate ingestion - Obtain medical attention immediately; if
could lead to neurological symptoms, breathing has stopped, apply artificial
such as tremors and convulsions; respiration; do not induce vomiting
main hazard of ingested liquid
formulations is aspiration into the
lung
ENVIRONMENT: very toxic for fish Do not contaminate ponds, -
and honeybees waterways, or ditches with product
or used containers
SPILLAGE STORAGE FIRE AND EXPLOSION
Absorb spillage with lime, damp Store in locked, well ventilated Some liquid formulations may be highly
sawdust, sand, or earth; sweep up, storeroom, away from feed flammable; DO NOT use water - use
place in closed container, and and foodstuffs, children and dry powder, carbon dioxide, or alcohol-
dispose of safely; avoid unauthorized personnel resistant foam; cool nearby drums with
contamination of personnel, ponds, water spray
and waterways
WASTE DISPOSAL
Burn in high temperature incinerator National Occupational
with effluent scrubbing; alternatively, Exposure Limit:
treat with 5% caustic soda as a
hydrolysing agent; comply with local
regulations National Poison Control Centre:
Local trade names:
7. CURRENT REGULATIONS, GUIDELINES, AND STANDARDS
The information given in this section has been extracted from the
International Register of Potentially Toxic Chemicals (IRPTC) legal
file and other United Nations sources. The intention is to give the
reader a representative but not exhaustive overview of current
regulations, guidelines, and standards.
The reader should be aware that regulatory decisions about chemicals
taken in a certain country can only be fully understood in the
framework of the legislation of that country.a
7.1 Previous Evaluations by International Bodies
The FAO/WHO Joint Meeting on Pesticide Residues (JMPR) discussed and
evaluated bioresmethrin at its meetings in 1975 and 1976. However, an
acceptable daily intake (ADI) was not established.
WHO has classified bioresmethrin as a technical product unlikely to
present an acute hazard in normal use and resmethrin and cismethrin as
slightly hazardous (WHO, 1986). A Data Sheet (No. 34) on
bioresmethrin has been issued (WHO/FAO, 1978).
7.2 Exposure Limit Values
In the USA, the maximum residue limit in or on food items resulting
from use of resmethrin in food-handling and storage areas is 3 mg/kg
(1983).
7.3 Specific Restrictions
No information available.
a The regulations and guidelines of all countries are subject to
change and should always be verified with the appropriate
regulatory authorities before application.
7.4 Labelling, Packaging, and Transport
The United Nations Committee of Experts on the Transportation of
Dangerous Goods classifies pyrethroids in:
Hazard Class 6.1: poisonous substance
Packing Group III: a substance presenting a relatively low
risk of poisoning in transport.
The label should be as follows:
The bottom half of the label should bear the inscription:
Harmful, stow away from foodstuffs.
The FAO specifications for bioresmethrin plant protection products
(technical product and formulations) advises on methods for checking
the composition and purity of bioresmethrin. The bioresmethrin
content shall be declared (g/litre or g/kg at 20°C) and may not
deviate by more than 5% from this.
Containers should be lined, where necessary, with a suitable material
or the interior surfaces treated to prevent corrosion and/or
deterioration of the contents. They should comply with pertinent
national and international transport and safety regulations.
The legislation of the European Community requires that resmethrins be
labelled as dangerous substances, using the symbol:
The label must read:
Harmful by inhalation, in contact with skin, and if swallowed;
keep out of reach of children; keep away from food, drink, and
animal feeding stuff.
7.5 Waste Disposal
In the USA, permits are required for discharge of pyrethroids from any
point source into national waters; detailed instructions are provided.
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