Cyfluthrin

Description

Cyfluthrin is a broad-spectrum synthetic pyrethroid insecticide with both contact and poison action. It is first registered by EPA in 1987 and found in both restricted use and general-use insecticides. Cyfluthrin is used for a wide array of pests in agriculture, in and around the home, and in food handling establishments. These pests include cutworms, ants, silverfish, cockroaches, termites, grain beetles, weevils, mosquitoes, fleas, flies, corn earworms, tobacco budworm, codling moth, European corn borer, cabbageworm, loopers, armyworms, boll weevil, alfalfa weevil, Colorado potato beetle, and many others. Cyfluthrin is also used in public health situations and for structural pest control. Cyfluthrin is neurotoxic. It could cause organ inflammation in many animal studies and induce skin paresthesia, as well as reproductive problems. Also, Cyfluthrin is highly toxic to fish, aquatic organisms and bees.

References

1. https://www.beyondpesticides.org
2. http://onlinelibrary.wiley.com
3. http://pmep.cce.cornell.edu
4. https://en.wikipedia.org/wiki/Cyfluthrin
5. http://dissemination.echa.europa.eu

Description

Cyfluthrin is a pyrethroid insecticide and a modulator of voltage-gated sodium channels (Na_v). It slowly activates rat recombinant Na_v1.8 channels, delays inactivation by longer than 40 ms, and induces persistent tail currents in channels expressed in X. laevis oocytes. It also decreases the mean burst rate in rat primary neurons (IC₅₀ = 0.99 μM, respectively). Cyfluthrin is toxic to various insects, including A. melinus, G. ashmeadi, E. eremicus, and E. formosa (LC₅₀s = 7, 67, 96, and 63 ng/ml, respectively) and the A. sinensis mosquito (LC₅₀ = 0.446 ppm). It is also toxic to A. mellifera honeybees (LD₅₀ = 0.22 ppm), affecting locomotor activity and wing fanning behavior with an increase in the mean bout duration of time spent upside down, indicating disruption of the righting reflex, and a decrease in wing fanning behavior when administered at a dose of 10 ng/bee. Formulations containing cyfluthrin have been used for the control of insects in agriculture and for non-commercial purposes.

Chemical Properties

In pure form this chemical may be colorless crystalline solid or powder. Commercial is a yellowish paste or viscous, yellowish-brown oil. Aromatic odor.

Uses

Insecticide

Uses

Cyfluthrin is used to control a wide range of insects, especially Lepidoptera, in cereals, fruit, vegetables and cotton. It is also used against migratory locusts and grasshoppers, in stored products, in public health situations and in animal health.

Definition

ChEBI: A carboxylic ester obtained by formal condensation between 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (4-fluoro-3-phenoxyphenyl)(hydroxy)acetonitrile.

General Description

A viscous amber partly crystalline oil. Used as an insecticide.

Reactivity Profile

Cyfluthrin is a pyrethrine derivative. Incompatible with azocyclotin, and perhaps other azo compounds and organometallics.

Agricultural Uses

Insecticide: Cyfluthrin is a non-systemic insecticide used to control a variety of chewing and sucking insects on cotton, hops, cereals, corn, peanuts, fruit, potatoes and other crops and vegetables. It is also used o control structural pests such as termites.

Trade name

AZTEC®; ATTATOX®; BAY FCR 1272®; BAYTHROID®; BAYTHROID® H; BAYTHROID® TECHNICAL; BUG-B-GON®; CONTUR®; CYLATHRIN®; EULAN SP®; FCR 1272®; INTUDER®; INTUDER HPX®; LASER®; RENOUNCE®; RESPONSAR®; SOLFAC®; TEMPO®; TEMPO® H; TEMPO® 20WP

Potential Exposure

Cyfluthrin is a synthetic pyrethroid, nonsystemic insecticide used to control a variety of chew- ing and sucking insects on cotton, hops, cereals, corn, pea- nuts, fruit, potatoes, and other crops and vegetables. It is also used to control structural pests such as termites. Cyfluthrin can be found in both Restricted Use Pesticides (RUP) and General Use Pesticides (GUP) category. It is also a nitrile.

Metabolic pathway

The non-enzymatic hydrolyzed products of 14C- cyfluthrin are isolated and identified by the incubation reaction mixture of a buffer solution. The products are derived from the hydrolysis of the ester linkage of cyfluthrin via cyanhydrin. This results in the corresponding aldehyde which undergoes both oxidation and reduction to give rise to carboxylic acid and benzyl alcohol, respectively.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3349 (pyrethroid pesticide, solid, toxic)/151 Pyrethroid pesticide, solid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material UN3439 Nitriles, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Degradation

Cyfluthrin is a stable compound but it is hydrolysed at high pH. DT₅₀ values in water at 22 °C at pH 4, 7 and 9 were 25-117, 11-20, and 3-7 days, respectively (PM). Under aqueous photolysis conditions (but using UV light and acetonitrile in the solution), its half-life was 12 days. The benzldehyde (3, 3%) (Scheme 1) and the benzoic acid (5, 9%) were detected at 144 hours (PSD).
On a soil surface in light, the initial half-life was 2 days. At day 9, 62% of the radioactivity was recovered as: cyfluthrin (36%)) 3 (2%), 5 (4%) and unidentified components (PSD). The compound was stable on a soil surface in the dark.

Incompatibilities

May react violently with strong oxidi- zers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders, or dust. Incompatible with silver compounds. Mixture with some silver compounds forms explosive salts of silver oxalate. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give car- boxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids .

Waste Disposal

Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.

References

[1] JIN-SUNG CHOI  David M S. Structure–activity relationships for the action of 11 pyrethroid insecticides on rat Nav1.8 sodium channels expressed in Xenopus oocytes[J]. Toxicology and applied pharmacology, 2006, 211 3: Pages 233-244. DOI: 10.1016/j.taap.2005.06.022
[2] MOHANA KRISHNAN BASKAR  Prakhya B M. In vitro evaluation of pyrethroid-mediated changes on neuronal burst parameters using microelectrode arrays[J]. Neurotoxicology, 2016, 57: Pages 270-281. DOI: 10.1016/j.neuro.2016.10.007
[3] KYU-SIK CHANG. Susceptibility and Resistance of Field Populations of Anopheles sinensis (Diptera: Culicidae) Collected from Paju to 13 Insecticides[J]. Osong Public Health and Research Perspectives, 2013, 4 2: Pages 76-80. DOI: 10.1016/j.phrp.2013.02.001
[4] CAITLIN J OLIVER. Pyrethroids and Nectar Toxins Have Subtle Effects on the Motor Function, Grooming and Wing Fanning Behaviour of Honeybees (Apis mellifera).[J]. PLoS ONE, 2015: e0133733. DOI: 10.1371/journal.pone.0133733