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Cypermethrin
Cypermethrin
Cypermethrin
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Cypermethrin
Names
IUPAC name
[Cyano-(3-phenoxyphenyl)methyl]3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.052.567 Edit this at Wikidata
KEGG
MeSH Cypermethrin
UNII
  • InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3 checkY
    Key: KAATUXNTWXVJKI-UHFFFAOYSA-N checkY
  • InChI=1/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3
    Key: KAATUXNTWXVJKI-UHFFFAOYAW
  • Cl/C(Cl)=C/C3C(C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C
Properties
C22H19Cl2NO3
Molar mass 416.30 g·mol−1
Pharmacology
P03BA02 (WHO) QP53AC08 (WHO)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H302, H332, H335, H373, H410
P260, P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P319, P330, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cypermethrin (CP) is a synthetic pyrethroid used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. It behaves as a fast-acting neurotoxin in insects. It is easily degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. It is a non-systemic and non-volatile insecticide that acts by contact and ingestion, used in agriculture and in pest control products. Exposure to sunlight, water and oxygen will accelerate its decomposition. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticide Information Center (NPIC) (previously National Pesticides Telecommunication Network) in the USA.[1] It is found in many household ant and cockroach killers, including Raid, Ortho, Combat, ant chalk, and some variants of Baygon in Southeast Asia.

Uses

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Cypermethrin is used in agriculture to control ectoparasites which infest cattle, sheep, and poultry.[2]

Human exposure

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Cypermethrin is moderately toxic through skin contact or ingestion. It may cause irritation to the skin and eyes. Symptoms of dermal exposure include numbness, tingling, itching, burning sensation, loss of bladder control, incoordination, seizures and possible death. Excessive exposure can cause nausea, headache, muscle weakness, salivation, shortness of breath and seizures.[citation needed]

Pyrethroids may adversely affect the central nervous system. Human volunteers given dermal doses of 130 μg/cm2 on the earlobe experienced local tingling and burning sensations. One man died after eating a meal cooked in a 10% cypermethrin/oil mix that was mistakenly used for cooking oil.[3] Shortly after the meal, the victim experienced nausea, prolonged vomiting, stomach pains, and diarrhea which progressed to convulsions, unconsciousness and coma. Other family members exhibited milder symptoms and survived after hospital treatment.

It may cause allergic skin reactions in humans.[4]

In humans, cypermethrin is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, which are eliminated in the urine. Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdosage may be confirmed by quantitation of cypermethrin in blood or plasma.[5]

Study in animals

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Cypermethrin is very toxic to cats which cannot tolerate the therapeutic doses for dogs.[6] This is associated with UGT1A6 deficiency in cats, the enzyme responsible for metabolizing cypermethrin. As a consequence, cypermethrin remains much longer in the cat's organs than in dogs or other mammals and can be fatal in large doses.

In male rats cypermethrin has been shown to exhibit a toxic effect on the reproductive system by Elbetieha et al. 2001.[7] In another result, after 15 days of continual dosing, both androgen receptor levels and serum testosterone levels were significantly reduced. These data suggested that cypermethrin can induce impairments of the structure of seminiferous tubules and spermatogenesis in male rats at high doses.[8]

Long-term exposure to cypermethrin during adulthood is found to induce dopaminergic neurodegeneration in rats, and postnatal exposure enhances the susceptibility of animals to dopaminergic neurodegeneration if rechallenged during adulthood.[9]

If exposed to cypermethrin during pregnancy, rats give birth to offspring with developmental delays. In male rats exposed to cypermethrin, the proportion of abnormal sperm increases. It causes genetic damage: chromosomal abnormalities increased in bone marrow and spleen cells when mice were exposed to cypermethrin.[10] Cypermethrin is classified as a possible human carcinogen, because it causes an increase in the frequency of lung tumors in female mice. Cypermethrin has been linked to an increase in bone marrow micronuclei in both mice and humans.[11]

One study showed that cypermethrin inhibits “gap junctional intercellular communication”, which plays an important role in cell growth and is inhibited by carcinogenic agents.[12] Studies have shown that residue from cypermethrin can last for 84 days in the air, on walls, the floor and on furniture.[13]

Environmental effects

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Cypermethrin is a broad-spectrum insecticide, which means it kills beneficial insects as well as the targeted insects.[14] Fish are particularly susceptible to cypermethrin,[15][16] but when used as directed, application around residential sites poses little risk to aquatic life.[17] Resistance to cypermethrin has developed quickly in insects exposed frequently and can render it ineffective.[18]

References

[edit]
[edit]
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Cypermethrin

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Cypermethrin is a synthetic with the molecular formula C₂₂H₁₉Cl₂NO₃ and a molecular weight of 416.3 g/mol, appearing as a to brown viscous liquid or semisolid. Developed in 1972 by Michael Elliott at the Rothamsted Experimental Station in the , it functions as a broad-spectrum that disrupts insect nervous systems by prolonging opening, causing hyperexcitation, , and death upon contact or ingestion. This non-systemic compound is valued for its photostability and low volatility, making it effective in diverse formulations such as emulsifiable concentrates, wettable powders, and long-lasting insecticidal nets. Cypermethrin is widely applied in agriculture to protect crops like , , and cereals from pests including , bollworms, and beetles, as well as in for in nets and indoor residual spraying, and in veterinary products for ectoparasite treatment on . Its commercial development involved collaboration with , leading to approvals for use in and integration into WHO-recommended long-lasting insecticidal nets for prevention since the early 2000s. The compound exists as a of eight stereoisomers, with alpha-cypermethrin (containing the most active isomers) often used for enhanced potency in formulations. While of low to moderate acute toxicity to mammals— with oral LD₅₀ values in rats ranging from 250–4,123 mg/kg and dermal LD₅₀ exceeding 2,000 mg/kg—cypermethrin can cause , , , and convulsions in s at high exposures, and is classified as a possible (EPA Group C) based on an increased incidence of benign adenomas and carcinomas in female mice. Environmentally, it exhibits high persistence in soil ( 30–100 days) and extreme toxicity to aquatic organisms (LC₅₀ for <0.1 µg/L) and bees (LD₅₀ 0.044 µg/bee), necessitating buffer zones and restrictions near water bodies to mitigate runoff impacts. The U.S. EPA has established tolerances up to 1.0 ppm in commodities like cattle fat and reregistered cypermethrin in 2008 with risk mitigation measures, while the WHO sets specifications for public health uses, including an acceptable daily intake of 0–0.02 mg/kg body weight.

Chemical Properties

Structure and Formula

Cypermethrin is a synthetic pyrethroid insecticide with the chemical formula \ceC22H19Cl2NO3\ce{C22H19Cl2NO3}. Its molar mass is 416.3 g/mol. The molecule consists of an ester linkage between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and α-cyano-3-phenoxybenzyl alcohol, more precisely described by its IUPAC name as [cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate. The core structure features a cyclopropane ring substituted with two methyl groups at position 2 and a dichlorovinyl side chain at position 3, connected via a carboxylate ester to a benzyl alcohol moiety bearing a phenoxy substituent at the meta position and a cyano group at the α-carbon. This arrangement is depicted textually as:
  • Cyclopropane ring: Central three-membered ring with geminal dimethyl at C2.
  • Dichlorovinyl group: -CH=CCl₂ attached to C3 of the ring.
  • Ester bridge: -C(O)O- linking C1 of the ring to the chiral α-carbon.
  • Phenoxybenzyl moiety: -CH(CN)-O- connected to a phenyl ring with -O-C₆H₅ at the 3-position.
Cypermethrin possesses three chiral centers—one at the α-cyano carbon and two in the cyclopropane ring (at C1 and C3)—resulting in eight possible stereoisomers, typically present as a racemic mixture in technical formulations. As a synthetic analog of natural pyrethrins derived from Chrysanthemum flowers, its structure mimics the ester-based framework of these natural insecticides while incorporating modifications for enhanced stability.

Physical and Chemical Characteristics

Cypermethrin appears as a yellow to brown viscous liquid or semi-solid at room temperature, with a characteristic odor, while its pure isomers form colorless crystals. The technical grade material has a melting point ranging from 60 to 80 °C, and it exhibits a density of approximately 1.25 g/cm³ at 20 °C. Cypermethrin is practically insoluble in water, with a solubility of less than 0.01 mg/L (specifically 0.004 mg/L at 20 °C), but it is highly soluble in organic solvents such as acetone (>450 g/L), (103 g/L), and (>450 g/L) at 20 °C. This low water solubility stems from its structural features, including the hydrophobic carboxylate and phenoxybenzyl moieties. Its (log Kow) is 6.0 to 6.5 (reported values of 6.3 or 6.60), indicating high and a propensity for in fatty tissues. The compound demonstrates good photostability in field conditions compared to natural pyrethrins, which degrade more rapidly under , allowing for extended residual activity in applications. It remains stable in neutral or weakly acidic media (optimal at 4) and is thermally stable up to 220 °C, but it hydrolyzes under alkaline conditions, with a of 1.8 to 2.5 days at 9. Cypermethrin has low volatility, characterized by a of approximately 2 × 10^{-8} mmHg at 25 °C (1.7 × 10^{-9} mmHg at 20 °C), which minimizes airborne dispersal during handling.

History and Development

Discovery

The discovery of cypermethrin emerged from intensive research in the 1970s aimed at developing synthetic pyrethroids that could serve as photostable alternatives to the natural pyrethrins extracted from flowers, which degraded rapidly under sunlight and limited their agricultural utility. This effort built upon foundational work from the , particularly the synthesis of allethrin by Milton S. Schechter, Frank B. LaForge, and colleagues at the U.S. Department of Agriculture, marking the first major step toward mimicking the insecticidal esters of pyrethrins using carboxylic acids. In 1972, cypermethrin was invented by Michael Elliott and his team, including Norman F. Janes and David A. Pulman, at the Rothamsted Experimental Station in the , under the auspices of the National Research Development Corporation (NRDC), prompted by Elliott's awareness of a for a related α-cyano-3-phenoxybenzyl . The compound, chemically known as (RS)-α-cyano-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, represented a targeted structural evolution from earlier pyrethroids like , incorporating an α-cyano substituent on the alcohol moiety to boost potency while retaining the core acid framework. Initial laboratory assays demonstrated cypermethrin's exceptional potency, with low concentrations achieving rapid knockdown and mortality against a range of insect pests, including aphids and beetles, outperforming natural pyrethrins and many contemporary insecticides in contact and residual activity tests. This high efficacy stemmed from its enhanced binding to insect sodium channels, prolonging nerve depolarization. A key milestone in pyrethroid innovation, cypermethrin was among the first to feature the dichlorovinyl substituent on the cyclopropane ring, which significantly improved photostability and field persistence compared to prior non-halogenated analogs, enabling broader practical applications while maintaining low mammalian toxicity.

Commercialization

Cypermethrin was introduced to the market in 1977 by (ICI, now part of ) in collaboration with the National Research Development Corporation (NRDC), marking the transition of this synthetic from laboratory synthesis to commercial insecticide. It was marketed under trade names such as Cyperkill, Ammo, Cymbush, and Ripcord, targeting broad-spectrum . The NRDC, which developed cypermethrin through synthesis in 1972 by Elliott et al., held key patents (e.g., NRDC 149) filed around 1974-1975, providing exclusive rights that expired in the and paved the way for generic production. Licensing agreements were central to its global rollout; NRDC granted production and sales rights to ICI for international markets and to Sumitomo Chemical Co., Ltd. in 1977 specifically for , enabling localized manufacturing and distribution. Early adoption was rapid, particularly in for in the late 1970s, with field applications demonstrated in regions like d'Ivoire (1978-1979) and . By 1980, over 92.5% of global production (approximately 380 tonnes) was used on , primarily in countries such as (47 tonnes), (44 tonnes), and (25 tonnes), reflecting its quick uptake for foliage pests like cutworms and expansion to over 50 countries by the . Initial formulations focused on emulsifiable concentrates (e.g., 100 g/ and 250 g/) to facilitate broad-spectrum application on crops and , supporting its efficacy as a contact insecticide.

Synthesis and Production

Manufacturing Process

The industrial manufacturing of cypermethrin involves a multi-step that produces technical-grade material with greater than 90% purity, primarily through esterification of a modified cyclopropanecarboxylic acid derivative with a alcohol. The process begins with the preparation of precursors: the cyclopropanecarboxylic acid component, specifically 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid, is derived from analogs of chrysanthemic acid via chlorination and reactions to introduce the dichlorovinyl group. Separately, the alcohol precursor, 2-hydroxy-3-(3-phenoxyphenyl)acetonitrile (also known as m-phenoxybenzaldehyde ), is synthesized by reacting m-phenoxybenzaldehyde with in an aqueous medium, often facilitated by phase-transfer to enhance reaction efficiency. The key esterification step couples the cyclopropanecarboxylic acid chloride—formed by chlorination of the acid—with the under controlled conditions, typically in an organic solvent like n-hexane, to yield cypermethrin. This reaction proceeds via nucleophilic acyl substitution, with the mixture subsequently washed using soda ash solution and water to remove impurities, followed by solvent stripping to isolate the product. Overall process yields for technical-grade cypermethrin range from 80% to 90%, depending on optimization of individual steps such as the cyanohydrin formation (often exceeding 95% in catalyzed variants). Phase-transfer is commonly employed in the cyanohydrin synthesis and sometimes in the ester linkage to improve yields and reduce solvent use by enabling reactions between immiscible phases. Production occurs on a large industrial scale, with batches typically yielding around 1 of cypermethrin per cycle and facilities capable of hundreds of metric tons per month, as operated by major manufacturers including and . Waste management focuses on organic solvents like n-hexane through , while aqueous effluents containing trace are detoxified with to below 0.2 ppm before treatment in effluent treatment plants (ETPs); chlorinated byproducts from earlier chlorination steps are similarly recovered to minimize environmental release.

Isomers and Formulations

Cypermethrin exhibits stereoisomerism due to three chiral centers: two on the cyclopropane ring and one on the α-cyano carbon of the alcohol moiety, resulting in eight possible stereoisomers comprising four cis and four trans diastereomers. The technical grade product is a racemic mixture of all eight isomers, typically containing 40–45% cis isomers and 55–60% trans isomers, though ratios can vary from 40:60 to 80:20 depending on the manufacturing process. The cis isomers generally exhibit greater biological activity than the trans isomers, contributing disproportionately to the overall insecticidal potency of the mixture. Commercial variants of cypermethrin are enriched in specific stereoisomers to enhance potency. Alpha-cypermethrin consists primarily of the two most active cis diastereomers (1R-cis-αS and 1S-cis-αR), comprising at least 90% of the mixture and demonstrating 2–3 times greater and insecticidal compared to technical cypermethrin. Beta-cypermethrin is a blend enriched in the two trans diastereomers (1R-trans-αS and 1S-trans-αR), offering improved over the standard mixture. Zeta-cypermethrin represents a further purified form, containing a specific blend of four active stereoisomers (primarily 1R-trans-αS, 1S-cis-αR, and minor amounts of 1R-cis-αS and 1S-trans-αR), which optimizes insecticidal performance while reducing the proportion of less active components. Isolation of these active isomers from the technical mixture involves epimerization under alkaline conditions to achieve stereochemical equilibrium, followed by selective to separate the desired diastereomers. This refinement process increases the overall efficacy of the product by 2–4 times compared to the unseparated , as it concentrates the more potent stereoisomers. For practical application, cypermethrin is formulated in various types to suit different delivery methods, including emulsifiable concentrates (EC), which form stable oil-in-water emulsions upon dilution; wettable powders (WP), dry powders that disperse in water; and granules (GR), pre-coated particles for soil or foliar release. Typical formulations contain 10–25% active ingredient by weight, balancing efficacy, stability, and ease of handling. Technical grade cypermethrin must meet purity standards of at least 90% (900 g/kg) active substance, as specified by FAO and WHO guidelines, ensuring minimal impurities and consistent performance in end-use products.

Mode in Insects

Cypermethrin primarily targets voltage-gated sodium channels (VGSCs) in the axons of insects, where it binds preferentially to the open state of the channel, requiring repeated depolarizations for effective modification. As a type II , cypermethrin contains an α-cyano-3-phenoxybenzyl moiety that enhances its binding affinity, prolonging the open state and slowing both inactivation and deactivation of the channels. This leads to extended sodium influx during action potentials, causing repetitive firing and disruption of normal impulse transmission. The resulting neurophysiological effects include hyperexcitation of the nervous system, characterized by uncontrolled tremors and loss of coordination, progressing to and death. Cypermethrin operates through contact with the or during feeding, and it functions as a non-systemic , exerting localized effects without translocation within the target organism. This mechanism renders it highly effective against diverse pests, including chewing like caterpillars and sucking pests such as and mosquitoes. Cypermethrin's selectivity for insects stems from structural differences in their VGSCs, such as the Vssc1/TipE channels, and their relatively slower processes, which allow the compound to persist longer in insect tissues. It produces a rapid knockdown effect, immobilizing within minutes of exposure, followed by lethality over several hours as the persistent sodium channel modification overwhelms the . Insect resistance to cypermethrin often arises from target-site mutations in VGSCs, notably the L1014F substitution, which diminishes channel sensitivity and enables survival despite exposure, leading to knockdown resistance.

Metabolism

Cypermethrin undergoes primary metabolism through ester catalyzed by carboxylesterases, yielding 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic and α-cyano-3-phenoxybenzyl alcohol, which are less toxic than the parent compound. This represents the initial step in biological systems, with the reaction simplified as: Cypermethrin+H2O→3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid+α-cyano-3-phenoxybenzyl alcohol\text{Cypermethrin} + \text{H}_2\text{O} \rightarrow 3\text{-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid} + \alpha\text{-cyano-3-phenoxybenzyl alcohol} Further degradation involves oxidation by cytochrome P450 enzymes, producing hydroxylated metabolites primarily at the phenoxybenzyl alcohol moiety and the cyclopropane ring, followed by conjugation with glucuronic acid or other agents to facilitate urinary and fecal excretion. In mammals, is rapid, with plasma half-lives on the order of hours due to efficient carboxylesterase and activity, leading to quick elimination primarily via and ; for instance, in rats, over 90% of an oral dose is excreted within 48 hours. In contrast, exhibit slower because of less efficient systems, allowing cypermethrin accumulation and prolonged disruption. Species-specific variations occur in conjugation; rats favor conjugates of phenoxybenzoic acid, while mice produce conjugates. Environmental microbes degrade cypermethrin via analogous pathways, initiated by esterase-like enzymes, though at rates influenced by and conditions, contributing to overall environmental breakdown without significant accumulation in non-target organisms.

Uses

Agricultural Applications

Cypermethrin is widely employed in for protecting a variety of from pests, particularly through foliar applications that target chewing and sucking insects. It is commonly used on to control bollworms (Helicoverpa spp.), on such as tomatoes and to manage () and caterpillars ( and ), on fruits including apples and to suppress similar pests, and on grains like and to combat stem borers and leaf folders. These applications help safeguard yields by disrupting pest populations that can cause significant damage during critical growth stages. Application rates for cypermethrin typically range from 50 to 200 g per , varying by (such as emulsifiable concentrates at 10-25% ai), target pest, and type; lower rates around 25-50 g/ha are often sufficient for early-season control, while higher rates up to 200 g/ha may be needed for severe infestations. Foliar sprays are the primary method, applied at intervals of 7-14 days with full canopy coverage to ensure contact efficacy, though seed treatments are occasionally used for initial protection against soil-dwelling pests in grains and . As a broad-spectrum , cypermethrin exhibits high efficacy against orders such as (e.g., bollworms and caterpillars) and Coleoptera (e.g., beetles), achieving rapid knockdown and mortality rates exceeding 90% in field trials on treated crops. Its residual activity persists for 2-4 weeks post-application, providing extended protection against reinfestation while degrading gradually under environmental conditions. In (IPM) programs, cypermethrin is rotated with other classes to delay resistance development, as practiced in major cotton-producing regions of and the , where it complements biological controls like predatory and cultural practices such as ; however, resistance in bollworms and other pests has been reported in these areas. Economically, cypermethrin helps mitigate bollworm-induced yield losses of up to 20-30% in cotton. Its cost-effectiveness and versatility support its use in large-scale agriculture.

Public Health and Veterinary

Cypermethrin, particularly its alpha-isomer, is widely employed in vector control programs to combat mosquito-borne diseases such as malaria and dengue, though efficacy can be reduced by resistance in mosquito populations. The World Health Organization (WHO) has prequalified long-lasting insecticidal nets (LLINs) treated with alpha-cypermethrin for malaria prevention, typically at a target concentration of 200 mg/m², which provides effective protection against Anopheles mosquitoes by inducing rapid knockdown and mortality. Indoor residual spraying (IRS) with alpha-cypermethrin, applied at 25 mg active ingredient per m², is also utilized in some regions for malaria vector control, targeting resting mosquitoes on indoor surfaces, and has demonstrated reduced mosquito densities in community trials. For dengue prevention, cypermethrin-based IRS contributes to Aedes aegypti control by disrupting vector populations in endemic areas, though its efficacy is influenced by application methods and local resistance patterns. In , cypermethrin serves as an ectoparasiticide for and companion animals, effectively targeting ticks, lice, fleas, mites, and flies. It is commonly applied to , sheep, , pigs, and via pour-on formulations along the animal's backline, providing residual protection against single-host ticks and nuisance flies for several weeks. For pets such as dogs and cats, cypermethrin is incorporated into shampoos, spot-on treatments, and sprays to control fleas and ticks, though it requires caution in felines due to their sensitivity. Trade names for veterinary products include Ectomin, Flectron, and , often formulated as ready-to-use solutions for direct application. Public health programs leverage cypermethrin for urban pest management, particularly against and houseflies that serve as mechanical vectors for pathogens. and residual spray formulations are deployed in residential and communal settings, providing rapid knockdown, though efficacy against cockroaches varies due to resistance in many populations. In fly control efforts, cypermethrin treatments on breeding sites and resting surfaces have shown 80-90% mortality rates in susceptible populations, supporting prevention in densely populated areas. Common formulations for these applications include aerosols for space spraying, dips for immersion of , and pour-ons for topical delivery, enabling targeted and efficient use. Cypermethrin's low mammalian profile, evidenced by its EPA "CAUTION" signal word indicating minimal acute risk at recommended doses, facilitates safe application in and health contexts, with rapid in mammals reducing . Globally, cypermethrin deployment is prominent in tropical and subtropical regions for control, with an estimated annual use of approximately 26 tons (26,000 kg) of the active ingredient dedicated to interventions against and dengue from 2010-2019. Alpha-cypermethrin adds another 34 tons annually, primarily in LLINs and spraying operations across , , and the , underscoring its role in preventing millions of vector-borne cases each year.

Toxicology

Human Exposure and Effects

Humans are primarily exposed to cypermethrin through dermal contact, , and , with dermal exposure being the most common route among occupational users such as agricultural applicators and pest control operators. Skin absorption occurs at rates of 0.3–1.8% of the applied dose, often leading to detectable urinary metabolites within hours of exposure. Inhalation exposure takes place during application processes like spraying, where airborne concentrations can range from 0.005 to 24 μg/m³. Ingestion may result from accidental consumption of contaminated food or water, or through hand-to-mouth transfer in residential or occupational settings. Acute effects of cypermethrin exposure in humans typically manifest as localized irritation, characterized by tingling or burning sensations, and eye redness, particularly following dermal contact. These symptoms, often reported by workers handling the , peak 3–6 hours after exposure and usually resolve within 12–24 hours. Ingestion of cypermethrin can cause systemic effects including , , , and in severe cases, tremors or convulsions, though such incidents are rare with prompt medical intervention. Chronic exposure to cypermethrin studies show limited epidemiological . The U.S. Environmental Protection Agency classifies cypermethrin as a possible (as of 2023), based on evidence of tumors in animal studies, with no clear human carcinogenicity available. The (ADI) for cypermethrin is established at 0.01 mg/kg body weight by the EPA, aligning with the reference dose (RfD) of 0.01 mg/kg/day to protect against chronic neurotoxic effects. Case studies of poisoning, including reports from involving 573 acute cases (1983–1988), document symptoms such as , , and mild neurological disturbances that generally resolve within 24–48 hours with supportive care. No widespread epidemics of cypermethrin poisoning have been recorded, reflecting its relatively low in humans when used as directed.

Animal Studies

Laboratory studies on cypermethrin in rats have demonstrated moderate , with oral LD50 values ranging from 247 mg/kg in males to 309 mg/kg in females, and dermal LD50 exceeding 4920 mg/kg, classifying it as Toxicity Category II for oral and Category III for dermal exposure. In subchronic 90-day feeding studies, the (NOAEL) was established at 7.5 mg/kg/day, while chronic 2-year studies identified a NOAEL of 1–7.5 mg/kg/day, with effects such as decreased body weight observed at higher doses. Reproductive and developmental toxicity assessments in rats showed no evidence of teratogenicity across multiple generations, though high doses around 50 mg/kg/day led to reduced in males, manifested as decreased counts and impregnation rates. Regarding carcinogenicity, chronic exposure resulted in increased incidences of benign lung adenomas in female mice, contributing to the U.S. EPA's of cypermethrin as a possible (Group C). Genotoxicity evaluations, including the Ames bacterial reverse mutation test and micronucleus assays in rats, were negative, indicating that cypermethrin is non-mutagenic under standard testing conditions.

Environmental Impact

Fate in Environment

Cypermethrin exhibits moderate in , with laboratory DT50 values ranging from 25 to 100 days under aerobic conditions, and field dissipation times from 14 to 112 days, depending on type, microbial activity, and environmental factors. It adsorbs strongly to and clay, characterized by Koc values exceeding 80,000 mL/g, which renders it highly immobile and minimizes the risk of leaching into . In aquatic environments, cypermethrin degrades rapidly upon exposure to , with photolysis half-lives of 0.6 to 1 day in natural river or , primarily through cleavage of its bond. In water-sediment systems, it hydrolyzes under anaerobic conditions, achieving total system DT50 values of 2.8 to 13.2 days, though the compound partitions quickly to where it remains bioavailable to benthic organisms despite adsorption. This partitioning reduces dissolved concentrations in the but sustains exposure risks in sediments. Cypermethrin has negligible volatility in air, with a of approximately 6 × 10⁻⁷ Pa at 25°C, limiting its transport as a gas phase and resulting in short atmospheric residence times, often on the order of hours due to rapid or deposition. The compound shows potential for based on its log Kow of 5.2 to 6.3, but experimental bioconcentration factors (BCF) in fish range from 100 to 1000 L/kg (e.g., 299 L/kg growth-corrected), constrained by rapid metabolism that prevents substantial buildup in tissues. Primary degradation products include 3-phenoxybenzoic acid and 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane , formed via ester hydrolysis, both of which exhibit similar or lower compared to the parent compound in aquatic systems.

Effects on Ecosystems

Cypermethrin exhibits high to aquatic organisms, primarily due to its rapid absorption through , which allows the compound to enter the bloodstream even at trace concentrations. Studies report 96-hour LC50 values for various ranging from 0.006 to 9.8 µg/L, with some sensitive showing values as low as 0.022 µg/L. For invertebrates like , toxicity is similarly severe, with LC50 values between 0.15 and 1.04 µg/L, rendering cypermethrin highly disruptive to freshwater ecosystems where runoff introduces it into bodies. In terrestrial environments, cypermethrin poses significant risks to pollinators and soil-dwelling organisms essential for . It is highly toxic to honey bees, with an acute contact LD50 of approximately 0.035 µg/bee, leading to substantial mortality in foraging populations and potential declines in services. Earthworms, critical for soil and , experience at soil concentrations around 20 mg/kg, where LC50 values indicate adverse effects on growth, reproduction, and burrowing activity, thereby compromising and fertility. While cypermethrin shows low to birds and mammals, with oral LD50 values exceeding 4640 mg/kg in species like ducks, indirect effects through the can amplify its ecological impact. in prey items may lead to sublethal physiological disruptions in higher trophic levels, such as impaired or altered in avian predators. Its moderate persistence in sediments and soils prolongs exposure risks, contributing to chronic in aquatic and terrestrial food webs. Secondary ecological effects of cypermethrin include pest resurgence and reductions in natural enemy populations, which exacerbate in agricultural landscapes. In , repeated applications have been linked to outbreaks of secondary pests like and due to the suppression of predatory and parasitoids, resulting in up to 40-50% greater reliance on chemical controls and associated declines in overall diversity. Case studies from intensive production areas demonstrate losses, including reduced populations of beneficial and wild plants near treated fields, which diminish habitat quality for non-target species. Recent studies as of 2025 have highlighted elevated toxicity risks from cypermethrin in pesticide mixtures to non-target aquatic and terrestrial species, as well as potential for bioremediation using biochar and bacteria like Bacillus cereus to reduce soil contamination. Mitigation strategies such as establishing vegetated buffer zones adjacent to watercourses can reduce spray drift and runoff, limiting cypermethrin's entry into aquatic habitats by up to 90% in some applications. Integrated Pest Management (IPM) approaches, incorporating selective application timing and biological controls, further minimize impacts on non-target species by preserving natural enemy populations and reducing overall pesticide loads in ecosystems.

Regulations and Safety

Global Regulations

Cypermethrin is regulated internationally as a synthetic , with approvals and restrictions varying by jurisdiction based on its toxicity profile, particularly to aquatic organisms and non-target species. In the United States, the Environmental Protection Agency (EPA) first registered cypermethrin in 1984 for use in agricultural and non-agricultural settings. The EPA has established tolerances for cypermethrin residues in food commodities, ranging from 0.05 ppm for items like pecans to 14 ppm for leafy greens (Crop Subgroup 5B), ensuring residues do not exceed safe levels under the Federal Food, Drug, and Cosmetic Act. In July 2025, the EPA established a tolerance of 1.0 ppm for residues on to facilitate imports, following a and confirming no harm to human health. In the , cypermethrin remains approved under Regulation (EC) No 1107/2009 as a candidate for substitution, with its current authorization extended until 2029, subject to ongoing risk mitigation measures due to concerns over environmental impacts. The (EFSA) reviewed maximum residue levels (MRLs) for cypermethrins in 2023, recommending adjustments to align with standards while lowering some MRLs for alpha-cypermethrin, which is no longer approved at the EU level since 2021. Several EU member states impose additional national restrictions on cypermethrin applications near aquatic environments to protect sensitive ecosystems, reflecting its classification as highly toxic to non-target aquatic life. In June 2025, the of the Court of Justice of the EU critiqued the Commission's re-approval process for cypermethrin, arguing that inadequate assessment of formulation-specific risks undermined the renewal decision, though no immediate full ban resulted. The (WHO) classifies cypermethrin (technical grade) as a Class Ib (highly hazardous) , emphasizing safe handling in its guidelines for applications, such as indoor residual spraying against vectors. WHO recommends its use in integrated vector management programs where resistance monitoring and environmental safeguards are in place to minimize exposure risks. In other regions, cypermethrin is widely produced in countries like and , which account for significant global supply and adhere to export tolerances aligned with importing nations' standards, such as Codex MRLs. However, it is prohibited in systems worldwide, including under the EU's organic regulation and the U.S. National Organic Program, due to its synthetic nature and potential for residue contamination. While no global bans exist, phase-out measures in sensitive areas, such as buffer zones near water bodies, have been implemented in various countries to address ecological concerns, with ongoing reviews focusing on alternatives for high-risk uses.

Risk Assessments

Risk assessments for cypermethrin evaluate potential hazards to human health and the environment through quantitative methods that integrate exposure estimates with data. The U.S. Environmental Protection Agency (EPA) employs margins of exposure (MOE) greater than 100 as a threshold indicating low concern for occupational uses, based on dermal and exposure scenarios where protective equipment further reduces risks. For dietary exposure, cumulative assessments of pyrethroids, including cypermethrin, demonstrate low risk, with chronic exposures occupying less than 1% of the population adjusted dose for vulnerable groups like children. Environmental risk assessments highlight elevated concerns in aquatic environments, where risk quotients (RQ) for cypermethrin often exceed 1, indicating potential adverse effects on sensitive and from runoff. strategies, such as product labels requiring spray drift reduction and vegetative buffer zones near water bodies, are implemented to lower these risks during application. The EPA utilizes a non-linear reference dose (RfD) approach for assessing cypermethrin's carcinogenicity, classified as a possible (), relying on no-observed-adverse-effect levels from acute studies rather than linear . Probabilistic modeling is applied to refine exposure estimates, incorporating variability in application rates, environmental fate, and ecological endpoints to better characterize aquatic risks. In 2025, the EPA conducted a human health risk assessment supporting new tolerances for cypermethrin residues on durian, concluding no additional risks from acute or chronic dietary exposures. The European Food Safety Authority (EFSA) has conducted peer reviews confirming low long-term toxicity risks, with an acceptable daily intake (ADI) of 0.02 mg/kg body weight per day, based on a no-observed-adverse-effect level of 2 mg/kg body weight per day from a 2-year rat study for systemic effects (increased liver weights). Post-registration monitoring includes surveillance for resistance in target pests and residue levels in and water, alongside of applicators to track urinary metabolites and ensure exposure remains below safety thresholds.

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