Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Cyphenothrin

Cyphenothrin

Cyphenothrin structure

Cyphenothrin 

structure
  • CAS No:

    39515-40-7

  • Formula:

    C24H25NO3

  • Chemical Name:

    Cyphenothrin

  • Synonyms:

    Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-,cyano(3-phenoxyphenyl)methyl ester;Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propenyl)-,cyano(3-phenoxyphenyl)methyl ester;α-Cyano-m-phenoxybenzyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate;SP 2703;Cyphenothrin;S 2703;α-Cyano-3-phenoxybenzyl chrysanthemate;S 2703 forte;Gokilaht;Chifenothrine;Rarappu MC;2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropane carboxylic acid cyano(3-phenoxyphenyl)methyl ester;Cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate;d-trans-Cyphenothrin

  • Categories:

    Agrochemicals  >  Insecticides

Description

Thick, yellow liquid.


Cyphenothrin is a cyclopropanecarboxylate ester. It has a role as a pyrethroid ester insecticide and an agrochemical. It derives from a chrysanthemic acid.

Cyphenothrin Basic Attributes

375.46

375.46

254-484-5

S0IU5Y1R32

DTXSID4032536

Viscous yellow liquid

29269090

Characteristics

59.3

6.59

Faint yellow sticky liquid.

1.2±0.1 g/cm3

<25 °C

154 °C

209.4±18.9 °C

1.594

0.001 mg l -1 (23 °C)

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

1.2×10 -4 pa 20°C

Henry's Law constant = 4.5X10-5 atm-cu m/mol at 25 °C (est)

A mixture of (RS, 1RS)-cis-trans- mixed isomers|Faint characteristic odor (Technical cyphenothrin)|BP: 154 °C at 0.1 mm Hg. VP: 0.4 mPa at 30 °C|Hydroxyl radical reaction rate constant = 1.04X10-10 cu cm/molec-sec at 25 °C (est)

Safety Information

III

6.1

UN 2810

3

22-50/53

60-61

GZ1453500

Xn;N,N,Xn

Stable under recommended storage conditions.

P273-P501

H302-H410

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 156 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|Danger|P260, P264, P270, P271, P284, P301+P312, P304+P340, P310, P320, P330, P403+P233, P405, and P501

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx).

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Normal measures for preventive fire protection.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Toxicity

IDENTIFICATION AND USE: Cyphenothrin is a type II pyrethroid. It is used as fumigant, insecticide, and veterinary medicine. HUMAN STUDIES: The symptoms of poisoning caused by pyrethroids are characterized by ataxia, loss of coordination, hyperexcitation, convulsions, and paralysis. Depending on the type of pyrethroid, repetitive discharges and/or conduction block are observed in various regions of the nervous system. Type II pyrethroids such as cyphenothrin contain a cyano group at the alpha-carbon cause nerve membrane depolarization and block leading to paralysis. The action is ascribed to modification of nerve membrane sodium channels which result in very slow gating kinetics. ANIMAL STUDIES: Tremors and convulsions have been noted in animals at 30 mg/kg and higher. There was no statistically significant increased incidence of neoplasms in oral studies for 104 weeks in mice. In developmental studies in rabbits there were no reproductive or teratogenic effects noted. Cyphenothrin was negative in genotoxicity studies with Salmonella typhimurium strains TA-1535, TA-1537, TA-1538, TA-98 and TA-100 and Escherichia coli WP-2 uvrA in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: The histopathological effects of several doses of cyphenothrin were observed in adult guppies (Lebistes reticulatus) at 34.8, 46.5, 53.5 or 60 ug cyphenothrin/L for 96-hr and their gills were examined. The most common changes at all cyphenothrin doses were the lifting of the epithelial layer from gill lamellae and some necrosis. Degeneration of secondary lamellae due to edema, the shortening of secondary lamellae, and club-shaped lamellae were also observed.

Despite the widespread use of pyrethroid insecticides that led to common exposure in the population, few studies have been conducted to quantitatively assess dose-additive effects of pyrethroids using a funcional measure involved in the common toxic mode of action. The aim of this study was to evaluate the potency and efficacy of 6 Type II pyretroids (alpha-cypermethrin, cyfluthrin, lambda-cyhalothrin, deltamethrin, cyphenothrin and esfenvalerate) to evoke induction of both nitric oxide and lipid peroxides levels measured as malondialdehyde in three in vitro models (SH-SY5Y, HepG2 and Caco-2 human cells) as well as to test the hypothesis of dose additivity for mixtures of these same 6 pyrethroids. Concentration-responses for 6 pyrethroids were determined as well as the response to mixtures of all 6 pyrethroids. Additivity was tested assuming a dose-additive model. The human neuroblastoma SH-SY5Y cell line was the most sensitive in vitro model. The rank order of potency for cell SH-SY5Y viability MTT assay was deltamethrin> cyphenothrin> lamda-cyhalothrin> cyfluthrin> esfenvalerate> alpha-cypermethrin. When 6 pyrethroids were present in the mixture at an equitoxic mixing ratio, the action on nitric oxide (NO) and lipid peroxides measured as malondialdehyde (MDA) production was consistent with a dose-additive model. The results of the present study are consistent with previous reports of additivity of pyrethroids in vivo e in vitro.

/AQUATIC SPECIES/ ...The histopathological effects of several doses of cyphenothrin /were observed/. Adult guppies (Lebistes reticulatus) were placed in water containing 34.8, 46.5, 53.5 or 60 micrograms cyphenothrin/L for 96-hr and their gills examined. The most common changes at all cyphenothrin doses were the lifting of the epithelial layer from gill lamellae and some necrosis. Degeneration of secondary lamellae due to edema, the shortening of secondary lamellae, and club-shaped lamellae were also observed. The 96-hr LC50 for cyphenothrin to Lebistes reticulatus was 48.7 ug/L.

Cyphenothrin's production may result in its release to the environment through various waste streams; its use as an insecticide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8.0X10+4(SRC), determined from a structure estimation method(2), indicates that cyphenothrin is expected to be immobile in soil(SRC). Volatilization of cyphenothrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 9.0X10-8 mm Hg(n), and water solubility, 1.0X10-2 mg/L(m). However, adsorption to soil is expected to attenuate volatilization(SRC). Cyphenothrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2018).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8.0X10+4(SRC), determined from a structure estimation method(2), indicates that cyphenothrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 9.0X10-7 mm Hg(4), and water solubility, 1.0X10-2 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 19 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 15 yrs if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 360(SRC), from its log Kow of 6.29(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data in water were not available(SRC, 2018).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyphenothrin, which has a vapor pressure of 9.0X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyphenothrin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hrs(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase cyphenothrin is degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 38 minutes(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase cyphenothrin may be removed from the air by wet and dry deposition(SRC). Cyphenothrin contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of cyphenothrin with photochemically-produced hydroxyl radicals has been estimated as 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of cyphenothrin with ozone has been estimated as 4.3X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 38 minutes at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). In general, pyrethrins and pyrethroids undergo hydrolysis in the environment at varying rates depending on pH and temperature(3). The compound is stable for at least 2 years under normal storage conditions(4). A base-catalyzed second-order hydrolysis rate constant of 6.1X10-3 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 36 and 4 yrs at pH values of 7 and 8, respectively(1). Cyphenothrin photodegradation in aqueous solution and an O2 atmosphere resulted in the formation of the corresponding ketolactone derivative and the caronic acid(5). Cyphenothrin contains chromophores that absorb at wavelengths >290 nm(6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 360 was calculated in fish for cyphenothrin(SRC), using a log Kow of 6.29(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of cyphenothrin can be estimated to be 8.0X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyphenothrin is expected to be immobile mobility in soil(SRC).

The Henry's Law constant for cyphenothrin is estimated as 4.5X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 9.0X10-7 mm Hg(1), and water solubility, 1.0X10-2 mg/L(1). This Henry's Law constant indicates that cyphenothrin is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 19 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 15 yrs if adsorption is considered(4). Cyphenothrin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Cyphenothrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

No reports of surface water or ground water monitoring studies that included cyphenothrin were found in searches of the United States Geological Survey (USGS) online National Water Quality Assessment Data Warehouse (NAWQA) database, nor the EPA publication, EPA Pesticides in Ground Water, A Compilation of Monitoring Studies 1971-1991 National Summary(1).

Occupational exposure to cyphenothrin may occur through inhalation and dermal contact with this compound at workplaces where cyphenothrin is produced or used. Monitoring data indicate that the general population may be exposed to cyphenothrin via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing cyphenothrin. (SRC)

Drug Information

VET: Efficacy of Frontline Tritak For Dogs (fipronil/(S)-methoprene/cyphenothrin ...) against Ixodes scapularis was evaluated in two separate, but concurrent laboratory studies. One day after topical treatment with placebo or active, dogs (n=24) were infested with 50 unfed adult Ixodes scapularis ticks, with repeat infestations on Days 7, 14, 21 and 28. The number of live ticks was counted at 6 hours post-infestation in the first study (n=12) and at 24 hours post-infestation in the second study (n=2). Observed efficacies in study 1 were 93-99% at 6 hour assessments on Day 1 through Day 28 and in the second study, 98-100% at 24 hour assessments, occurring on Day 2 through Day 29. A single dose of Frontline Tritak For Dogs (fipronil/(S)-methoprene/cyphenothrin) ... prevented the establishment of a new infestation following treatment, as well as the repeated weekly re-infestations with Ixodes scapularis ticks, for 4 weeks.|VET: The objective of this study was to determine the therapeutic and residual efficacy of a topically applied combination of cyphenothrin (40%) and pyriproxyfen (2%) against the tick Haemaphysalis elliptica and the flea Ctenocephalides felis on dogs. Twelve dogs were infested with 50 ticks 2 days before they were treated and with approximately 100 fleas 6 days before treatment and again 2 days before treatment and with 50 ticks and approximately 100 fleas at weekly intervals thereafter. They were ranked according to their flea counts and sex 5 days before treatment and randomly allocated to an untreated control group of 6 dogs and a treated group of 6 dogs. Ticks and fleas were collected from the dogs 48 h after treatment and 48 h after each infestation and live and dead ticks and live fleas were counted. The counts of ticks and fleas were transformed to geometric means, and efficacy was calculated by comparing these means. The product had a therapeutic efficacy of 83.1% against H. elliptica and 97.5% against C. felis 2 days after treatment. The residual period of protection during which efficacy was > or = 90% was 5 weeks for both H. elliptica and C. felis.

(14)C tissue residue levels 7 days after single oral or subcutaneous administration of each of the (14)C-labeled preparations of trans- and cis-cyphenothrin were measured. With the acid- and alcohol-labeled preparations of the trans and cis isomers, the tissue residue levels were generally very low. On the other hand, the CN-labeled preparations showed relatively higher tissue residues than other labeled preparations.|Single oral or subcutaneous administration of (14)C-trans or cis-cyphenothrin labeled in the acid or alcohol moiety to rats at 2-4 mg/kg resulted in almost complete elimination of the (14)C from the animal body. Major excretion routes with the acid- or alcohol- (except for the CN group) labeled preparation were the urine and feces. The total recovery of the (14)C within 7 days after administration of these labeled preparations was more than 93% in urine and feces. On the other hand, the (14)C derived from the CN group was more slowly excreted. In addition, 4-6% of the (14)C was expired as (14)CO2. The total (14)C recovery was 60-80% for the trans and cis isomers. The three labeled preparations of the trans and cis isomers showed more urinary excretion of the (14)C with subcutaneous than with oral administration.

In vivo and in vitro comparative metabolism studies of phenothrin and cyphenothrin showed the following results: (1) The trans isomers of cyphenothrin and phenothrin were hydrolyzed more rapidly in vitro (liver homogenates) and in vivo than the corresponding cis isomers, and cis-cyphenothrin was hydrolyzed to a larger extent than cis-phenothrin. (2) Plasma esterases showed a different substrate specificity form the liver esterases and hydrolyzed the trans and cis isomers of cyphenothrin and phenothrin to nearly the same extents. From the results of the in vivo and in vitro studies, the CN group introduced into the molecule did not affect the biodegradability of trans-cyphenothrin, but rather made cis-cyphenothrin more biodegradable than cis-phenothrin. These in vivo metabolic profiles (ester hydrolysis rate, excretion pattern into urine and feces) make be mainly determined by activity and/or substrate specificity of the liver esterases.|Both the trans and cis isomers underwent the following major metabolic reactions: (1) oxidation at the 2'- and 4'-phenoxy positions of the alcohol moiety; (2) oxidation at the isobutenyl and the gem-dimethyl groups of the acid moiety; (3) cleavage of ester linkage; (4) conversion of the CN ion to SCN ion and CO2; and (5) conjugation of the resulting carboxylic acids and phenols with glucuronic acid, sulfuric acid, and glycine.

The symptoms of poisoning caused by pyrethroids are characterized by ataxia, loss of coordination, hyperexcitation, convulsions, and paralysis. Depending on the type of pyrethroid, repetitive discharges and/or conduction block are observed in various regions of the nervous system. Type I pyrethroids as represented by allethrin and tetramethrin which lack a cyano group cause repetitive discharges in nerve fibers and nerve terminals leading to hyperexcitation of the animal. Type II pyrethroids as represented by cyphenothrin, deltamethrin and fenvalerate which contain a cyano group at the alpha-carbon cause nerve membrane depolarization and block leading to paralysis of the animal. Both types of action are ascribed to modifications of nerve membrane sodium channels which result in very slow gating kinetics. Patch clamp single channel recording experiments have clearly demonstrated that individual sodium channels are modified by tetramethrin in an all-or-none manner to give rise to a prolonged opening without change in conductance. Thus, it is concluded that the site of action of pyrethroids is the sodium channel, and that pyrethroids interact with the channel macromolecules that control the gating mechanism.

Decontaminate the skin promptly with soap and water ... . If irritant or paresthetic effects occur, obtain treatment by a physician. Because volatilization of pyrethroids apparently accounts for paresthesia affecting the face, strenuous measures should be taken (ventilation, protective face mask and hood) to avoid vapor contact with the face and eyes. Vitamin E oil preparations (dL-alpha tocopheryl acetate) are uniquely effective in preventing and stopping the paresthetic reaction. They are safe for application to the skin under field conditions. Corn oil is somewhat effective, but possible side effects with continuing use make it less suitable. Vaseline is less effective than corn oil, and zinc oxide actually worsens the reaction. /Pyrethroids/|Treat eye contamination immediately by prolonged flushing with copious amounts of clean water or saline. Some pyrethroid compounds can be very corrosive to the eyes, so extraordinary measures should be taken to avoid eye contamination. If irritation persists, professional ophthalmologic care should be obtained. /Pyrethroids/|If only small amounts of pyrethroid have been ingested, or if treatment has been delayed, administer activated charcoal and a cathartic orally as this probably represents optimal management. Do not give cathartic if patient has diarrhea or an ileus. Several drugs are effective in relieving the pyrethroid neurotoxic manifestations observed in deliberately poisoned laboratory animals, but non has been tested in human poisonings. Therefore, neither efficacy nor safety under these circumstances is known. Furthermore, moderate neurotoxic symptoms and signs are likely to resolve spontaneously. /Pyrethroids/|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Pyrethrins, pyrethroids, and related compounds/|For more Antidote and Emergency Treatment (Complete) data for Cyphenothrin (6 total), please visit the HSDB record page.

/BIOMONITORING/ An observational biomonitoring study was conducted involving adults and children in households that purchased and applied a cyphenothrin-containing spot-on product for dogs as part of their normal pet care practices. The 3- to 6-yr-old children had greater exposure than the adult applicators in the same house, 3.8 and 0.6 ug/kg body weight, respectively. The mean measured values in children were 13-fold lower than those estimated using the U.S. Environmental Protection Agency (EPA) current standard operating procedures (SOP) for pet products (assuming 5% dermal absorption), although the maximum absorbed dosage of one child on one day was equivalent to the default value derived from the SOPs. With regard to potential human health risks, it can be concluded that despite the inherent conservatism in both the exposure and toxicology data, the margins of exposure (MOE) were consistently greater than 100 for average, 95th percentile, and maximum exposures. More specifically, the results of this study demonstrated that the MOE were consistently greater than 1,000 for mean exposures and exceeded 100 for 95th percentile and maximum measured exposures, which clearly indicates a reasonable certainty of no harm when using the cyphenothrin spot-on products. It is also noteworthy that Sergeant's spot-on products containing cyphenothrin currently sold in the United States have lower weight percentages of active ingredient and lower applied amounts than those used by all but two of the participant households in this study.|/ALTERNATIVE and IN VITRO TESTS/ Despite the widespread use of pyrethroid insecticides that led to common exposure in the population, few studies have been conducted to quantitatively assess dose-additive effects of pyrethroids using a funcional measure involved in the common toxic mode of action. The aim of this study was to evaluate the potency and efficacy of 6 Type II pyretroids (alpha-cypermethrin, cyfluthrin, lambda-cyhalothrin, deltamethrin, cyphenothrin and esfenvalerate) to evoke induction of both nitric oxide and lipid peroxides levels measured as malondialdehyde in three in vitro models (SH-SY5Y, HepG2 and Caco-2 human cells) as well as to test the hypothesis of dose additivity for mixtures of these same 6 pyrethroids. Concentration-responses for 6 pyrethroids were determined as well as the response to mixtures of all 6 pyrethroids. Additivity was tested assuming a dose-additive model. The human neuroblastoma SH-SY5Y cell line was the most sensitive in vitro model. The rank order of potency for cell SH-SY5Y viability MTT assay was deltamethrin> cyphenothrin> lamda-cyhalothrin> cyfluthrin> esfenvalerate> alpha-cypermethrin. When 6 pyrethroids were present in the mixture at an equitoxic mixing ratio, the action on nitric oxide (NO) and lipid peroxides measured as malondialdehyde (MDA) production was consistent with a dose-additive model. The results of the present study are consistent with previous reports of additivity of pyrethroids in vivo e in vitro.

cis-cyphenothrin

Cyphenothrin Use and Manufacturing

Methods of Manufacturing

Preparation: T. Matsuo et al., German patent 2231312; eidem, United States of America patent 3835176 ( 1973, 1974 to Sumitomo).

Uses

Insecticide.

Parastar Plus for Dogs (Elanco US, Inc.): Active ingredient: cyphenothrin 5.2% and fipronil 9.8%.|Multicide Intermediate 2738 (McLaughlin Gormley King Company): Active ingredient: MGK 264 12.77%; prallethrin 1.0%; and cyphenothrin 13.34%.|Multicide Total Release Aerosol 27381 (McLaughlin Gormley King Company): Active ingredient: MGK 264 0.38%; prallethrin 0.03%; and cyphenothrin 0.4%.|MGK F-2926(P) (McLaughlin Gormley King Company): Active ingredient: cyphenothrin 7.2%.|For more Formulations/Preparations (Complete) data for Cyphenothrin (25 total), please visit the HSDB record page.

Registration Notes: USA: Not for edible crop use.|Used indoors in household/domestic dwellings, storage areas, pet living quarters, ships, processing plants, on horses and dogs; and outdoors on external doorways, window cracks and under porches liquid squeeze-on product on dogs and horses; aerosol/fogger for indoor control; spray for crack and crevice spot treatment

Pharmaceuticals

Computed Properties

Molecular Weight:375.5
XLogP3:5.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:375.18344366
Monoisotopic Mass:375.18344366
Topological Polar Surface Area:59.3
Heavy Atom Count:28
Complexity:634
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Cyphenothrin

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.