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
- https://www.beyondpesticides.org
- http://onlinelibrary.wiley.com
- http://pmep.cce.cornell.edu
- https://en.wikipedia.org/wiki/Cyfluthrin
- 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 (IC
50 = 0.99 μM, respectively). Cyfluthrin is toxic to various insects, including
A. melinus,
G. ashmeadi,
E. eremicus, and
E. formosa (LC
50s = 7, 67, 96, and 63 ng/ml, respectively) and the
A. sinensis mosquito (LC
50 = 0.446 ppm). It is also toxic to
A. mellifera honeybees (LD
50 = 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
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.
Production Methods
The commercial production of cyfluthrin involves a multi-step chemical synthesis that integrates several key intermediates to form its complex structure. The process begins with the preparation of the cyclopropane carboxylic acid derivative, which is then esterified with a fluorinated phenoxybenzyl alcohol containing a cyano group. This esterification step is crucial for forming the active cyfluthrin molecule.
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
Mechanism of action
Non-systemic with contact and stomach action and rapid knock-down effect. Sodium channel modulator.
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. DT
50
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
Pesticide Type
Insecticide
