Environmental Chemistry, Ecotoxicity,

and Fate of Lambda-Cyhalothrin

Li-Ming He, John Troiano, Albert Wang, and Kean Goh

1 Introduction ......................................................................................................................... 72
2 Chemistry of Lambda-Cyhalothrin ..................................................................................... 72
2.1 Synthesis .................................................................................................................... 73
2.2 Physicochemical Properties ....................................................................................... 74
2.3 Mode of Action .......................................................................................................... 75
3 Breakdown Mechanisms and Products ............................................................................... 75
3.1 Photolysis ................................................................................................................... 75
3.2 Hydrolysis .................................................................................................................. 77
3.3 Microbial Degradation ............................................................................................... 78
4 Environmental Fate of Lambda-Cyhalothrin ...................................................................... 78
4.1 Dissipation in Water .................................................................................................. 78
4.2 Interaction with Soil and Sediment............................................................................ 78
5 Ecotoxicity of Lambda-Cyhalothrin ................................................................................... 81
5.1 Fish and Shellfish ...................................................................................................... 81
5.2 Macrophytes .............................................................................................................. 82
5.3 Invertebrates............................................................................................................... 82
5.4 Sediment Toxicity ...................................................................................................... 83
5.5 Effects on Soil Fauna ................................................................................................. 84
5.6 Bioaccumulation ........................................................................................................ 85
6 Mitigating Runoff of Residues Through Plant Interaction ................................................. 85
6.1 Assimilation by Plants ............................................................................................... 86
6.2 Adsorption and Degradation by Plants ...................................................................... 86
7 Summary ............................................................................................................................. 87
References ............................................................................................................................. 88

L.-M. He (*)
Surface Water Protection Program, Environmental Monitoring Branch, Department of Pesticide
Regulation, California Environmental Protection Agency, 1001 I Street, Sacramento, CA 95814,
USA (e-mail: [email protected])
J. Troiano
Surface Water Protection Program, Environmental Monitoring Branch, Department of Pesticide
Regulation, California Environmental Protection Agency, 1001 I Street, Sacramento, CA 95814, USA
K.S. Goh
Surface Water Protection Program, Environmental Monitoring Branch, Department of Pesticide
Regulation, California Environmental Protection Agency, 1001 I Street, Sacramento, CA 95814, USA
A. Wang
Office of Environmental Health Hazard Assessment, California Environmental Protection Agency,
P.O. Box 4010, Sacramento, CA 95812-4010, USA

D.M. Whitacre (ed.), Reviews of Environmental Contamination and Toxicology. 71

© Springer 2008
72 L.-M. He et al.

1 Introduction

Lambda-cyhalothrin is a pyrethroid insecticide. Pyrethroids are synthetic chemical

analogues of pyrethrins, which are naturally occurring insecticidal compounds pro-
duced in the flowers of chrysanthemums (Chrysanthemum cinerariaefolium).
Insecticidal products containing pyrethroids have been widely used to control insect
pests in agriculture, public health, and homes and gardens (Amweg and Weston 2005;
Oros and Werner 2005). In agriculture, target crops include cotton, cereals, hops,
ornamentals, potatoes, and vegetables, with applications made to control aphid, cole-
opterous, and lepidopterous pests. Pyrethroids are important tools used in public
health management where applications are made to control cockroaches, mosquitoes,
ticks, and flies, which may act as disease vectors. Residential use of pyrethroid prod-
ucts has increased because of the suspension of organophosphate products containing
chlorpyrifos or diazinon (Oros and Werner 2005; Weston et al. 2005).
Lambda-cyhalothrin is the active ingredient (a.i.) in several brand name prod-
ucts: Warrior, Scimitar, Karate, Demand, Icon, and Matador. Annual agricultural
use of lambda-cyhalothrin in California has been consistent at approximately
30,000 lbs a.i. per annum from 2000 to 2003 and increased to ∼40,000 lbs a.i. per
annum between 2004 and 2006 (CDPR 2006). Residues of lambda-cyhalothrin
have been detected in irrigation and storm runoff water and in their associated sedi-
ments. Residues have been detected in runoff resulting from agricultural, public
health, and residential applications. For example, lambda-cyhalothrin was detected
in water at 0.11–0.14 µg/L from agricultural watersheds in Stanislaus County,
California. Lambda-cyhalothrin residues were detected in sediments obtained from
sites sampled in Imperial, Monterey, Stanislaus, and Placer Counties. Residues in
sediment ranged from 0.003 to 0.315 µg/g of dry wt (Starner 2007).
Toxicity tests conducted at levels of lambda-cyhalothrin residues measured in
water or sediment indicate potential for effects on aquatic organisms including fish
and amphipods (Amweg et al. 2005, 2006; Cavas and Ergene-Gozukara 2003; Gu
et al. 2007; Heckmann and Friberg 2005; Lawler et al. 2007; Maund et al. 1998;
Van Wijngaarden et al. 2005; Wang et al. 2007; Weston et al. 2004). Concerns have
therefore been raised about the widespread use of lambda-cyhalothrin in California
and its potential impact on aquatic ecosystems. This review is limited to literature
available from peer-reviewed publications and approved documents and databases
and is not deemed to be exhaustive. Research results from studies using multiple
pyrethroids that included lambda-cyhalothrin were used in this review to augment
data from studies conducted solely with lambda-cyhalothrin.

2 Chemistry of Lambda-Cyhalothrin

Lambda-cyhalothrin is a 1:1 mixture of two stereoisomers, (S)-α-cyano-3-

phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl
cyclopropanecarboxylate (Fig. 1a) and (R)-α-cyano-3-phenoxybenzyl-(Z) -(1S,3S)-
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 73

F3C O (S)-alcohol(Z)-(1R)-cis-acid

C CH C N
C O
CH3
Cl C
H
H H
CH3
O
a

H H
CH3
(R) - alcohol (Z) - (1S) - cis - acid
Cl
C O H
C CH CH3
O C
F3C
N C
O
b

Fig. 1 The chemical structure of two isomers of lambda-cyhalothrin

3-(2-chloro-3, 3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
(Fig. 1b). Lambda-cyhalothrin was first reported by Robson and Crosby (1984) and
was introduced in Central America and the Far East in 1985 by ICI Agrochemicals
(now Syngenta).

2.1 Synthesis

Dried and ground pyrethrum chrysanthemum flowers were noted to be powerful

insecticides in ancient China, but it took until the middle of the 20th century for the
first improved chemical analogues of the natural pyrethrin a.i.s to be commercially
synthesized. Naturally occurring pyrethrins are esters consisting of a so-called
“acid” component, which has a cyclopropane core and an “alcohol” component. At
first, synthetic pyrethroids were developed through alcohol substitutions. This early
generation of synthetic pyrethroids had drawbacks, mostly the result of poor stabil-
ity in sunlight. Photostability was greatly improved by substituting vinylic halo-
gens in the acid component (Spurlock 2006). Additional α-cyano-substitution in
the alcohol component by the National Research Development Corporation in the
UK further improved light stability and insecticidal activity. The commercial prod-
uct KARATE, whose a.i. is lambda-cyhalothrin, was registered for use by the U.S.
Environmental Protection Agency (USEPA) in 1988 (Syngenta 2007).
It is known that some isomers have a greater insecticidal effect than others, and
this has led to the development of techniques to separate the more-active isomers
and to convert the less-active isomers into the more-active ones. Conversion between
74 L.-M. He et al.

isomers is characterized by the base chemical, which promotes the desired epimeriza-
tion through proton removal at the carbon atom bearing the cyano group (Cleugh and
Milner 1994). Gamma-cyhalothrin is a single stereoisomer that has effective insecti-
cidal activity, with a much lower total reported use in California (CDPR 2007).

2.2 Physicochemical Properties

Lambda-cyhalothrin is a colorless solid at room temperature but may appear yel-

lowish in solution. Lambda-cyhalothrin has a low vapor pressure and Henry’s law
constant, which suggests that it is not easily volatilized into the atmosphere. This
insecticide also has a high octanol–water partition coefficient (Kow), so it tends to
partition into lipids (Table 1). Normally, a pesticide with a high Kow would signal a
high potential to bioconcentrate.
The mean water–soil organic carbon partition coefficient (Koc) is high, which
indicates preferential affinity to organic matter and suggests that it is unlikely to
contaminate groundwater because of a low potential to leach as dissolved residues
in percolating water. The tendency to adsorb to suspended particulate materials in

Table 1 Physical, chemical, and environmental properties of lambda-cyhalothrin

CAS number 91465-08-6
US EPA PC Code 128897
CA DPR Chem Code 2297
Molecular formula C23H19ClF3NO3
Molecular weight (g/mol) 449.9
Density (g/mL at 25°C) 1.33
Melting point (°C) 49.2
Boiling point (°C at 0.2 mmHg) 187–190
Vapor pressure (mPa at 20°C) 0.0002
Henry’s law constant (Pa-m3/mole) 0.018
Water solubility (mg/L at 20°C) 0.005
Solubility in other solvents (e.g., acetone) (mg/L) > 500,000
Octanol–water partitioning (log Kow at 20°C) 7.00
Hydrolysis half-life (d)
pH 5 Stable
pH 7 Stable
pH 9 8.66
Photolysis half-life (d)
Water at pH 5 and 25°C 24.5
Soil 53.7
Bioconcentration factor (BCF) (fish) 2,240
Soil adsorption Koc (cm3/g) 247,000–330,000
Soil degradation half-life (d)
Aerobic soil 42.6
Aquatic degradation half-life (d)
aerobic aquatic 21.9
Source: CDPR 2007; Laskowski 2002; PAN 2007; Tomlin 2000; USDA 2007;
USEPA 2007.
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 75

the water column, including clay particles and organic matter, provides the primary
vector for transport through aquatic systems. Thus, the greatest risk to nontarget
aquatic organisms would be through exposure to lambda-cyhalothrin-contaminated
sediments. Adsorbed phases of chemical molecules generally show decreased deg-
radation rates because residues are less accessible to breakdown by sunlight or
microorganisms than when molecules are dissolved in the water column
(Schwarzenbach et al. 1993). Sorption of lambda-cyhalothrin to suspended solids
or bottom sediments may provide a mechanism to mitigate its acute toxicity to
aquatic organisms by reducing its short-term bioavailability in the water column.

2.3 Mode of Action

Pyrethroids are axonic poisons that affect the nerve fiber by binding to a protein that
regulates the voltage-gated sodium channel. Normally, this gate opens to cause stimu-
lation of the nerve and closes to terminate the nerve signal. The channels are path-
ways through which ions are permitted to enter the axon and cause excitation. When
the channels are left open, nerve cells produce repetitive discharges and eventually
cause paralysis (Bradbury and Coats 1989; Shafer and Meyer 2004). Pyrethroids bind
to this gate and prevent it from closing normally, which results in continuous nerve
stimulation and tremors in poisoned insects. Poisoned organisms lose control of their
nervous system and are unable to produce coordinated movement.
There are two groups of pyrethroids with distinctive poisoning symptoms, denoted
as Type I and Type II. Chemically, Type II pyrethroids are distinguished from Type I
pyrethroids by the presence of an α-cyano group in their structure. In comparison to
Type I pyrethroids (e.g., permethrin), which exert their neurotoxicity primarily
through interference with sodium channel function in the central nervous system,
Type II pyrethroids (e.g., lambda-cyhalothrin) can also affect chloride and calcium
channels that are important for proper nerve function (Burr and Ray 2004).
Because of the lipophilic nature of pyrethroids, biological membranes and tissues
readily absorb them. Specifically, lambda-cyhalothrin penetrates the insect cuticle,
disrupting nerve conduction within minutes; this leads to cessation of feeding, loss
of muscular control, paralysis, and eventual death. Additional protection of the
crop is provided by the insecticide’s strong repellent effect toward insects.

3 Breakdown Mechanisms and Products

3.1 Photolysis

As indicated previously, the naturally occurring pyrethrins are unstable in light,

while the photostability of recent synthetic pyrethroids has been improved.
Photochemical studies with lambda-cyhalothrin were conducted under UV and
76 L.-M. He et al.

sunlight irradiation to understand photodegradation kinetics, pathways, and prod-

ucts (Fernandez-Alvarez et al. 2007; Ruzo et al. 1987). Exposure to UV light (18 W,
254 nm) for 20 min resulted in nearly complete degradation with losses greater than
95% of initial amounts applied (Fernandez-Alvarez et al. 2007). Photodegradation
of lambda-cyhalothrin followed first-order kinetic behavior where the apparent
first-order rate constant (kap) and half-life (t1/2) were determined to be 0.163 min−1
and 4.26 min, respectively.
With the recent development of highly efficient extraction methods and high-
resolution detection techniques, it is possible to identify multiple trace photoprod-
ucts and photodegradation pathways for lambda-cyhalothrin. Several pathways
have been proposed for the photodegradation of lambda-cyhalothrin, including
decarboxylation, reductive dehalogenation, and ester or other bond cleavage
(Fernandez-Alvarez et al. 2007) (Fig. 2).
The photoproduct decarboxycyhalothrin (P4) of lambda-cyhalothrin is gener-
ated by the decarboxylation pathway. The ester bond cleavage of lambda-

F 3C O

C CH C OH
CH3
Cl (P1)
H H
CH3

F 3C O

C CH C N
C O
CH3
Cl C
H
H H
CH3
O

HO F3C
CH2 C CH C N
CH3
Cl
C
O (P3)
H H H
CH3
O
NC
CH2 (P4)
H3C

O
O
(P2)
(P5)

Fig. 2 Photodegradation pathways and products for lambda-cyhalothrin

Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 77

cyhalothrin generates 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl

cyclopropanecarboxylic acid (P1) and (3-phenoxyphenyl)acetonitrile (P2).
The photoproduct P2 can also be generated by C–C bond cleavage of photoproduct
P4. Photoproduct P3 ( (3-phenoxyphenyl)methanol) can be generated by the
ester cleavage and subsequent loss of the cyano group of lambda-cyhalothrin.
The photoproduct 1-methyl-3-phenoxybenzene (P5) may be formed by hydroxyl or
cyano group losses from P3 or P2 (Fernandez-Alvarez et al. 2007).

3.2 Hydrolysis

Lambda-cyhalothrin is stable at pH below 8, whereas under alkaline conditions it

hydrolyzes through nucleophilic attack of the hydroxyl ion. A cyanohydrin derivative
is formed, which degrades to yield HCN and the corresponding aldehyde (Fig. 3)
(Gupta et al. 1998).

F3C O

C CH C N
C O
CH3
Cl C
H
H H
CH3
O

KOH

C N
HO F3C O
C
+ C CH
CH3
C OK
H
Cl
O
H H
CH3

HOOC

O + HCN

Fig. 3 Hydrolysis products of lambda-cyhalothrin

78 L.-M. He et al.

3.3 Microbial Degradation

In laboratory studies, the dissipation of lambda-cyhalothrin in soil was mainly

through biodegradation, as indicated by the rapid loss of lambda-cyhalothrin in
non-sterile soil compared to sterile soil (Wang et al. 1997). Only one degradate,
which was (RS)-α-cyano-3-(4-hydroxyphenoxy)benzyl-(Z)-(1RS)-cis-3-(2-chloro-
3, 3, 3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate, was determined
as a major breakdown product comprising 10% of the initial lambda-cyhalothrin
concentration (European-Commission 2001).

4 Environmental Fate of Lambda-Cyhalothrin

4.1 Dissipation in Water

Lambda-cyhalothrin rapidly dissipates from water (Farmer et al. 1995). The fate of
lambda-cyhalothrin was compared in mesotrophic and eutrophic ditch microcosms
where it was applied three times at 1-wk intervals at concentrations of 10, 25, 50,
100, and 250 ng/L. The rate of dissipation of lambda-cyhalothrin in the water
column of the two systems was similar where, after 1 d, only 30% of the amount
applied remained in the water phase (Roessink et al. 2005). Similarly, in an investigation
of the fate of both gamma- and lambda-cyhalothrin in laboratory-simulated rice
paddy water, their concentrations decreased rapidly, with no gamma-cyhalothrin or
lambda-cyhalothrin detected after 3 and 4 d, respectively (Wang et al. 2007). Last,
after simulating a seasonal exposure equivalent to 12 “drift” and 6 “runoff” events,
each delivering a dose equivalent to that expected from a typical event under field
conditions, the lambda-cyhalothrin concentration measured after the final application
was less than 2 ng/L (Hadfield et al. 1993).

4.2 Interaction with Soil and Sediment

4.2.1 Adsorption

Adsorption is one of the key processes controlling the fate of pyrethroids, which, as
indicated by their high Koc values, results in rapid and strong adsorption to soils and
sediments. Ali and Baugh (2003) investigated the adsorption of lambda-cyhalothrin
to silica, which is the major mineral component in soil. They discovered much-
reduced sorption to the mineral component, implying that discharge of pyrethroids
to water bodies is mainly in the sorbed soil organic phase. In another study of sorption
to mineral components of soil, four pyrethroids were used to investigate selective
interactions with corundum, quartz, montmorillonite, and kaolinite. Initial pyrethroid
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 79

concentrations ranged from 1 to 100 µg/L. Sorption to glass centrifuge tubes used
in the batch experiments was significant and accounted for 25%–60% of total sorption
(Oudou and Hansen 2002; Zhou et al. 1995). All corrected adsorption isotherms fit
the Freundlich equation with exponential n values ranging between 0.9 and 1.1.
These n values indicated little curvature in the adsorption isotherm. Bonding affinities
per unit surface area decreased in the order corundum > quartz > montmorillonite
> kaolinite. All minerals showed the same selectivity order with respect to sorption
affinity of the four pyrethroids: lambda-cyhalothrin > deltamethrin > cypermethrin
> fenvalerate (Oudou and Hansen 2002).
Adsorption is a surface phenomenon that for pyrethroids has been shown to
depend on the surface area and the organic carbon content of the adsorption.
Sorption–desorption equilibria of six pyrethroids (permethrin, cyfluthrin, cyper-
methrin, lambda-cyhalothrin, deltamethrin, and fenvalerate) were determined after
24-hr equilibrium in soils with an organic carbon content that ranged from 1.15%
to 2.46%. Again, the Freundlich equation fit the adsorption isotherms well, with the
values of the exponent n around unity. The desorbed amount of lambda-cyhalothrin
after five steps of desorption using deionized water was only 4.68% of the original
amount, indicating that lambda-cyhalothrin adsorption to soil was virtually irre-
versible in water (Ali and Baugh 2003).
The phase distribution of lambda-cyhalothrin was investigated as a function of
contact time in sediment (Bondarenko et al. 2006). For freshwater sediments at 9 d,
the dissolved fraction measured by solid-phase microextraction ranged from 1.7%
to 16.3% of the total pore-water concentration as determined by liquid–liquid
extraction. The dissolved fraction decreased substantially with contact time to less
than 5% at 30 d after sediment dosing. The dissolved fraction was lower in the
marine sediment, ranging from 1.1% to 4.2%. Consequently, the apparent KOC and
dissolved organic carbon partition coefficient (KDOC) values increased significantly
over the contact time, especially in the freshwater sediment, suggesting that phase
distribution was not at equilibrium after 9 d.
In general, the adsorption capacity of all soils with different organic content was
much higher than that of pure mineral particles, suggesting that lambda-cyhalothrin
had partitioned into the organic carbon phase as well as adsorbed onto the particle
surfaces. However, in investigations of the adsorptive capacity of organic coatings
on minerals, Zhou et al. (1995) discovered that adsorption was not constant and that
it decreased with increasing polarity and decreasing aromaticity of organic sorb-
ents. This result implied that the quantity, as well as the quality, of the organic mat-
ter on particle surfaces should be characterized to better predict contaminant
transport in aquatic and soil environments.

4.2.2 Effect of pH on Lambda-Cyhalothrin Adsorption

The effect of pH on sorption was examined by conducting experiments over a range

of four different pH values: 2, 4, 6, or 9 (Ali and Baugh 2003). The results showed
that, over this range, pH did not have a significant impact, although soil-sorbed
80 L.-M. He et al.

lambda-cyhalothrin at pH < 4 was slightly higher than at pH 9. The results support

the assumption that the adsorption of lambda-cyhalothrin is not significantly
affected by changing the surface charge density of soil or organic matter.

4.2.3 Terrestrial Dissipation Studies

The dissipation of lambda-cyhalothrin in laboratory-controlled soils was mainly

through biodegradation, as indicated by the rapid loss of lambda-cyhalothrin in
nonsterile soil when compared to a sterile soil (Wang et al. 1997). However, the
shape of the dissipation curve potentially indicated that processes primarily respon-
sible for degradation differed over time. In the cotton soil, dissipation of lambda-
cyhalothrin was fast in the first few days, which could indicate that degradation was
initially through photolysis and hydrolysis chemical processes. The subsequent
dissipation rate showed a steady slow decline, which could be evidence of micro-
bial degradation. Dissipation curves for a Brazilian Oxisol-Typic Haplustox can be
described by biexponential functions for lambda-cyhalothrin (Laabs et al. 2000).
Soil in pans was treated with lambda-cyhalothrin at 15 g/ha using an indoor track
sprayer, and the pans were dug into adjacent fallow and cropped areas of a field.
Overall, the initial lambda-cyhalothrin residues (32 ppb or 11.8 g/ha) dissipated
with a DT50 of 1.3 wk and a DT90 of 14.5 wk (disappearance time for first 50% and
90% of residue, respectively). Among treatments, residues in the soil pans shaded
by the crop canopy declined faster (DT90 of 12.8 wk) than residues in the fallow
area (DT90 of 16.2 wk). Compared with bare fallow, soil surface temperatures on
warm, summer days were 8°–16°C cooler within the crop canopy. Also, the surface
0–2.5 cm of soil within the canopy took longer to dry out after a rainfall. It was
hypothesized that the more ideal soil temperature and moisture conditions within
the crop canopy increased the microbial degradation of lambda-cyhalothrin. One
year after application, only 3.2% of the initial residues were recovered in the fallow
area (Hill and Inaba 1991).
The influence of temperature and moisture on the degradation and persistence
of lambda-cyhalothrin was investigated using laboratory incubation and lysimeters
on a sandy loam soil (Typic Ustocurepts) in Pakistan (Tariq et al. 2006). Drainage
from the lysimeters was sampled on days 49, 52, 59, 73, 100, 113, and 119 against
the pesticide application on days 37, 63, 82, 108, and 137 after the sowing of cotton.
The dissipation of lambda-cyhalothrin followed second-order kinetics. The results
of incubation studies showed that increasing temperature and moisture content sig-
nificantly reduced the t1/2 values of pesticides in laboratory-controlled soils (Tariq
et al. 2006; Wang et al. 1997).
Hydrosoil (sediment) appeared to act as a sink for lambda-cyhalothrin (Hadfield
et al. 1993). Under the stringent test conditions of the mesocosm study, lambda-
cyhalothrin residues in the hydrosoil (1.1% organic matter) reached 3.2 µg/kg fol-
lowing the seasonal exposure. Residues in the hydrosoil reached a maximum level
of approximately 25 µg/kg in one sampling zone at one interval and thereafter
declined to a level of 9 µg/kg within 4 mon.
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 81

4.2.4 Transport in Soil

In a study to evaluate the leaching potential of eight pesticides in a Brazilian Oxisol,

lambda-cyhalothrin was applied onto a Typic Haplustox that contained ∼50% clay
and 26.3 g/kg organic carbon in the top 10-cm soil layer (Laabs et al. 2000). Mobility
within the soil profile and subsequent leaching were studied for a period of 28 d after
application. The bulk of lambda-cyhalothrin residues were recovered within the top
15 cm of the soil. In lysimeter percolates collected at 35 cm soil depth, less than
0.03% of the applied amount of lambda-cyhalothrin was recovered. The relative
contamination potential of pesticides, according to the lysimeter study results, was
ranked as follows: metolachlor > atrazine = simazine >> monocrotofos > endosulfan
> chlorpyrifos > trifluralin > lambda-cyhalothrin. This same order of contamination
potential was achieved by ranking the pesticides according to their effective
sorption coefficient (Ke), which is the ratio of Koc to field-dissipation half-life.
The potential for pesticide transport in preferential flow in an Oxisol was inves-
tigated in a study where lambda-cyhalothrin was applied on to a Typic Haplustox
(Reichenberger et al. 2002). After application, a tracer solution containing 5 g/L of
the dye Brilliant Blue FCF and 0.015 M KBr was applied at a rate of 40 mm/d in
duplicate experiments over a period of 3 d. The solution was applied using either a
tension infiltrometer (3.3 cm tension) or manual irrigation with a watering can. The
soil monoliths were then opened and the soil layers at 0–5, 5–10, 10–20, 20–30,
and 30–40 cm were quantitatively removed. Although the highest concentrations of
lambda-cyhalothrin were found in the top 0–10 cm layer, detection of lambda-cyha-
lothrin in the deeper 10–30 cm soil layer was determined to result from preferential
flow (Reichenberger et al. 2002; Tariq et al. 2006).

5 Ecotoxicity of Lambda-Cyhalothrin

Lambda-cyhalothrin is slightly to highly toxic to terrestrial and aquatic organisms.

This review focuses on aquatic toxicity because aquatic organisms are most likely
to be exposed to lambda-cyhalothrin residue levels found in water and associated
sediment. It is worth noting that the reported oral LD50 (48 hr) for mallard duck was
> 3950 mg/kg, and that the oral LD50 (48 hr) was 0.038 µg/bee and the contact LD50
(48 h) was 0.909 µg/bee, indicating relatively low toxicity to ducks but high toxicity
to bees (European-Commission 2001).

5.1 Fish and Shellfish

Lambda-cyhalothrin is highly toxic to a number of fish and shellfish. The reported

LC50 (96 hr) is 210 ng/L for bluegill sunfish, 240 ng/L for rainbow trout, 360 ng/L
for Daphnia magna, 4.9 ng/L for mysid shrimp, and 0.8 ng/L for sheepshead min-
82 L.-M. He et al.

now. An EC50, the concentration at which the effect occurs in 50% of the test popu-
lation, for eastern oyster is 0.59 ng/L. A bioconcentration factor (BCF) of 2240 has
been reported in fish (species unspecified), but concentration was confined to
nonedible tissues and rapid depuration was observed (USDA 2007; USEPA 2007).
Because lambda-cyhalothrin is commonly applied to rice fields to control
insects, potential water and sediment contamination may lead to toxicity in aquatic
organisms such as mosquitofish, shrimps, crabs, and clams. Replicated enclosures
in a rice field were sprayed with the lambda-cyhalothrin product Warrior at 5.8 g
a.i./ha. Mosquitofish were added either before the spray or 7 d later. Of those added
before the spray, none survived. Most fish added 7 d later survived (Lawler et al.
2003). Lambda-cyhalothrin showed high toxicity to shrimp (Macrobrachium nip-
poensis de Haan) and zebrafish (Brachydanio rerio H.B). The 96-hr LC50 was 20–
70 ng/L for shrimp and 0.98–7.55 µg/L for zebrafish. In drainage water ponds with
lambda-cyhalothrin concentrations ranging from 0.45 to 0.90 µg/L, the 96-hr mor-
tality was 100% for shrimp, but the drainage water showed no toxicity to shrimp
on the fourth day after application of lambda-cyhalothrin (Gu et al. 2007). The 96-
hr LC50 values for lambda-cyhalothrin and gamma-cyhalothrin were similar for
zebrafish (1.93 µg/L for gamma and 1.94 µg/L for lambda). However, lambda-cyhalothrin
was more toxic (LC50, 0.04 µg/L) than gamma-cyhalothrin (LC50, 0.28 µg/L) to
shrimp, possibly implying that the toxicity to shrimp is likely stereochemistry
dependent (Wang et al. 2007).

5.2 Macrophytes

The structure of an ecosystem determines the final effect of pesticide exposure to

macrophytes (Wendt-Rasch et al. 2004). Using a pesticide mixture containing lambda-
cyhalothrin applied to 10 mesotrophic aquatic ecosystems dominated by submerged
macrophytes (Elodea) and 10 simulated eutrophic ecosystems with a high Lemna
surface coverage, significant increases in the biomass and alterations of species
composition of the periphytic algae were observed in the Elodea-dominated microcosms,
but no effect on Myriophyllum spicatum growth was observed. The opposite was
found in the Lemna-dominated microcosms, in which decreased growth of M. spicatum
was observed but no alterations were observed in the periphytic community.
Furthermore, application of 0.17 and 1.7 g a.i. ha−1 lambda-cyhalothrin to pond mesocosms
failed to produce adverse effects on macrophytes (Farmer et al. 1995).

5.3 Invertebrates

Lambda-cyhalothrin effects on mesotrophic (macrophyte-dominated) and eutrophic

(phytoplankton-dominated) ditch microcosms were studied; applications were
made three times at 1-wk intervals and at concentrations of 10, 25, 50, 100, and
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 83

250 ng/L (Roessink et al. 2005). Initial, direct effects were primarily on arthropod
taxa. The most sensitive species was the phantom midge (Chaoborus obscuripes).
At treatment levels of 25 ng/L and higher, apparent population and community
responses occurred. At treatments of 100 and 250 ng/L, the rate of recovery of the
macroinvertebrate community was lower in the macrophyte-dominated systems,
primarily because of a prolonged decline of the amphipod Gammarus pulex. This
species occurred at high densities only in the macrophyte-dominated enclosures.
Indirect effects (e.g., increase of rotifers and microcrustaceans) were more pro-
nounced in the plankton-dominated test systems, particularly at treatment levels of
25 ng/L and higher.
Simulated aquatic ditch mesocosms were used to understand the toxic effects of
potential spray drift from a typical crop application of pesticides including lambda-
cyhalothrin. Spray application to the water surface was at 0.2%, 1%, and 5% of the
recommended label rates. To interpret the observed effects, treatment concentra-
tions were expressed in toxic units (TU = actual concentration/EC50) (Arts et al.
2006), which describe the relative toxicity of the compounds with common toxicity
test organisms (Daphnia and algae). After treatment, lambda-cyhalothrin disap-
peared from the water phase within 2 d. At the 5% treatment level, exposure con-
centrations exceeded 0.1 TUDaphnia, and this resulted in long-term effects on
zooplankton and macroinvertebrates, some of which did not fully recover by the
end of the study (Arts et al. 2006). Previous studies with pesticides in experimental
ecosystems have demonstrated that effects on primary producers are likely to occur
at TUAlgae > 0.1 and effects on invertebrates are likely to occur at TU > 0.01–0.1
(Van Wijngaarden et al. 2004, 2005).

5.4 Sediment Toxicity

Recent studies have shown that pyrethroids including lambda-cyhalothrin are com-
monly found in aquatic sediments in the heavily agricultural Central Valley of
California, and therefore the toxicity of sediment-associated pyrethroid residues to
aquatic organisms has been actively investigated (Amweg et al. 2005; Weston et al.
2004). Seventy sediment samples were collected from 42 sites over a 10-county
area in the agriculture-dominated Central Valley of California, with most sites
located in irrigation canals and small creeks dominated by agricultural effluent.
Significant mortality was observed with the amphipod Hyalella azteca at 42% of
the locations and for the midge Chironomus tentans at 40% of the sites. Using a
toxicity unit analysis, measured pyrethroid concentrations were sufficiently high to
have contributed to the toxicity in 40% of samples toxic to C. tentans and nearly
70% of samples toxic to H. azteca (Weston et al. 2004).
In a follow-up aquatic toxicity study with six pyrethroids (Amweg et al. 2005),
the average 10-d median lethal concentration LC50 of sediment-associated residues
of lambda-cyhalothrin was 0.45 µg/g OC (organic carbon adjusted), corresponding
to an estimated pore-water concentration of 1.4 ng/L. Lambda-cyhalothrin would
84 L.-M. He et al.

be acutely toxic to H. azteca at the concentration of 5.6 ng/g dry wt of sediment.

Growth was typically inhibited at concentrations below the LC50; animal biomass
on average was 38% below controls when exposed to lambda-cyhalothrin concentrations
roughly one-third to one-half the LC50; i.e., the growth lowest-observable-effect
concentration (LOEC) was 0.19 µg/g OC. Survival data indicate that exposure
occurs primarily via the interstitial water rather than the particulate phase.
If only the dissolved concentration is bioavailable (Gan et al. 2006; Maund et al.
1998), these observations suggest that contact time after sediment dosing may
greatly affect the bioavailability and, hence, the toxicity of pyrethroids. Therefore,
a long contact time (30 d) is recommended for sediment toxicity testing of this class
of compounds. The dependence of bioavailability on contact time also implies that
test conditions must be standardized to allow comparison between laboratory-dosed
samples and field samples (Bondarenko et al. 2006).

5.5 Effects on Soil Fauna

Species sensitivity distributions (SSD) and 5% hazardous concentrations (HC5)

are distribution-based approaches for assessing environmental risks of pollut-
ants, e.g., lambda-cyhalothrin risks to soil invertebrate communities. From a
systematic review of literature, a total of 1950 laboratory toxicity test results
were obtained, representing 250 pesticides including lambda-cyhalothrin and
67 invertebrate taxa. The majority (96%) of pesticides have toxicity data on
fewer than 5 species. Based on a minimum of 5 species, the best available end-
point data (acute mortality median lethal concentration) enabled SSD and HC5
to be calculated for 11 pesticides including lambda-cyhalothrin. Arthropods
and oligochaetes exhibit pronounced differences in their sensitivity to most of
these pesticides. The standard test earthworm species, Eisenia fetida sensu lato,
is least sensitive to insecticides based on acute mortality, whereas the standard
Collembola test species, Folsomia candida, is among the most sensitive species
for a broad range of toxic modes of action (biocide, fungicide, herbicide, and
insecticide) (Frampton et al. 2006). To assess the effects of lambda-cyhalothrin
on soil invertebrates under tropical conditions, ecotoxicological semifield stud-
ies were conducted using intact soil-core terrestrial model ecosystems (TMEs)
(Forster et al. 2006). Earthworms, isopods, and diplopods were added to intact
soil cores and the mortality of soil invertebrates was determined. The results
indicated that lambda-cyhalothrin was toxic to isopods and millipedes, whereas
no effect on arthropods was detected in the field.
To evaluate possible microbial community changes in a sandy loam soil in
response to the addition of lambda-cyhalothrin, the following properties were
determined: active soil microbial biomass, concentrations of ammonium and
nitrate ions, numbers of total cultivable bacteria, fungi, nitrogen-fixing bacteria,
and nitrifying and denitrifying bacteria (Cycon et al. 2006). Substrate-induced
respiration (SIR) increased with time in controls ranging from 13.7 to 23.7 mg O2/
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 85

kg dry soil/hr and in pesticide-treated soil ranging from 12–13 to 23–25 O2/kg dry
soil/hr on days 1 and 28, respectively. The concentrations of nitrate and ammonium
ions, numbers of total cultivable bacteria, denitrifying bacteria, nitrogen-fixing bacteria,
and fungi were either unaffected or even stimulated by the pesticide treatments.

5.5 Bioaccumulation

The interaction of lambda-cyhalothrin with larvae of the aquatic insect

Chironomus riparius was studied in laboratory sediment–water systems (Hamer
et al. 1999). C. riparius, a nonbiting midge, is widely used for investigating
toxicity and bioaccumulation of contaminants in sediment. Ten different sedi-
ments were used. 14C-Labeled lambda-cyhalothrin was applied to sediment
slurries and C. riparius was exposed in the test system for 48 hr. In all the sedi-
ment–water test systems, > 99% of the 14C-labeled lambda-cyhalothrin was
adsorbed onto the sediment. BCFs based on the aqueous-phase concentrations
showed little difference among systems, ranging from 1,300 to 3,400 with a
mean of 2,300 and with a coefficient of variation of 25%. These values were
very similar to a BCF of 2,000 that was determined in water alone after 48 hr.
These BCF values are similar to chlorpyrifos, which is 1,374, but higher than
diazinon, which is 500 (PAN 2007). BCFs based on measured concentrations
of extractable 14C-lambda-cyhalothrin in the sediment phase were always < 1,
ranging from 0.11 to 0.84 with a mean of 0.39 and coefficient of variation of
61%. Sediment BCFs were inversely proportional to the measured sediment Kds,
which ranged from 3,290 to 22,100; that is, the higher the proportion of the
chemical that was adsorbed, the lower the sediment BCF. The results of the
study supported equilibrium partitioning theory. In sediment–water systems,
the lambda-cyhalothrin that was bioavailable is equivalent to the amount that is
measured in the water phase.

6 Mitigating Runoff of Residues Through

Plant Interaction

Because lambda-cyhalothrin residues in water and sediment may exert adverse

impacts on aquatic life, management practices have been investigated and
developed to mitigate such impact. Plants have long been recognized to have
the ability to sequester a variety of contaminants (e.g., organic or inorganic
chemicals) in water, sediment, and soil (Bouldin et al. 2006; Burken and
Schnoor 1997; Henderson et al. 2007; Mertens et al. 2006; Montes-Bayon et al.
2002; Siciliano et al. 1998; Wild et al. 2005). In recent years, the efficacy of
vegetated ditches to reduce pesticide residues in agricultural runoff has been
86 L.-M. He et al.

extensively studied. The results indicate that vegetated ditches are useful for
the reduction of lambda-cyhalothrin in stormwater or agricultural runoff
(Bennett et al. 2005; Bouldin et al. 2005; Leistra et al. 2004; Moore et al. 2001;
Roessink et al. 2005). Pesticide uptake, adsorption, and accelerated degradation
by plants in a vegetated ditch are the principal mechanisms of mitigation by
plants, as described next.

6.1 Assimilation by Plants

Macrophytes (e.g., Juncus effuses and Ludwigia peploides) can take up a significant
portion of lambda-cyhalothrin residues in water. Eight days after application, 98.2%
of lambda-cyhalothrin was found in the roots of L. peploides. Translocation of
lambda-cyhalothrin in J. effusus resulted in 25.4% of pesticide uptake partitioning
into upper plant biomass. These macrophytes showed species- and pesticide-specific
uptake rates, and therefore the selection of high-uptake plants enhances mitigation
capabilities in edge-of-field conveyance structures (Bouldin et al. 2006).

6.2 Adsorption and Degradation by Plants

Plants growing in an agricultural drainage ditch not only slow water flow and
absorb chemicals dissolved in water, but they will also act as surfaces for pesticide
adsorption and catalysts for their degradation. Many studies have been conducted
to investigate the effectiveness of vegetated drainage ditches for reducing pesticide
residue export from agricultural lands to creeks and rivers (Bennett et al. 2005;
Bouldin et al. 2005; Moore et al. 2001). By incorporating vegetated drainage
ditches into a watershed management program, agriculture can continue to decrease
potential non-point source threats to downstream aquatic receiving systems.
Overall results of previous studies illustrate that aquatic macrophytes play an
important role in the retention and distribution of pyrethroids, including lambda-
cyhalothrin, in vegetated agricultural drainage ditches.
The reduction effectiveness of pesticides through a drainage ditch is usually
described by the percentage of reduction of the pesticide:

Reduction% = (conc. at inlet – conc. at outlet) × 100/conc. at inlet

The reduction% is affected by several factors including the length and slope of
ditch, the type and density of vegetation, and the type of soil (Arts et al. 2006;
Bennett et al. 2005; Bouldin et al. 2005; Leistra et al. 2004; Milam et al. 2004;
Moore et al. 2001; Roessink et al. 2005).
Laboratory studies indicated that adsorption to macrophytes was extensive and
essentially irreversible, and that degradation of lambda-cyhalothrin occurred rapidly
by cleavage of the ester bond. In the indoor microcosm, which contained water,
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 87

sediment, and macrophytes, degradation was also rapid, with DT50 and DT90 values
of less than 3 and 19 hr, respectively, for dissipation from the water column and less
than 3 and 56 hr, respectively, for dissipation from the whole system (Hand et al.
2001). The adsorption of lambda-cyhalothrin by Ludwigia peploides (water prim-
rose) and Juncus effusus (soft rush) was significant and reached as high as 86.50 µg/
kg (Bouldin et al. 2005).
In a vegetated drainage ditch study, following initiation of simulated runoff,
mean percentages of lambda-cyhalothrin concentrations in water and sediment in
the ditch were 12% and 1%, respectively. Lambda-cyhalothrin mean percentage
concentrations in plants [Polygonum (water smartweed), Leersia (cutgrass), and
Sporobolus (smutgrass)] were 87%. The concentrations in water decreased to
levels safe for nontarget species 50 m downstream from the point of input (Moore
et al. 2001).
A controlled-release runoff simulation was conducted on a 650-m vegetated
drainage ditch in the Mississippi Delta. Lambda-cyhalothrin was released into the
ditch in a water–sediment slurry (Bennett et al. 2005). Samples of water, sediment,
and plants were collected and analyzed for lambda-cyhalothrin concentrations.
Three hours following runoff initiation, inlet lambda-cyhalothrin water concentra-
tion was 374 µg/L in the inlet and 7.24 µg/L at 200 m downstream. No lambda-
cyhalothrin residues were detected at the 400-m sampling site. A similar trend was
observed throughout the first 7 d of the study where water concentrations were ele-
vated at the front end of the ditch (∼25 m) and greatly reduced downstream at the
400-m sampling site. Regression formulas predicted that lambda-cyhalothrin con-
centrations in ditch water were reduced to 10% of the initial value within 280 m
downstream from point of input. Mass balance calculations determined that ditch
plants constituted the major sink and/or sorption site responsible for the rapid aque-
ous pyrethroid dissipation.
In a ditch study conducted in the Netherlands, concentrations of lambda-cyha-
lothrin decreased rapidly in the water column: 24%–40% of the dose remained in
the water 1 d after application, and it had decreased to 1.8%–6.5% after 3 d (Leistra
et al. 2004). At the highest plant density, lambda-cyhalothrin residues in the plant
compartment reached a maximum of 50% of the dose after 1 d; at intermediate and
low plant densities, this maximum was only 3%–11% of the dose (after 1–2 d). The
percentage of the insecticide in the ditch sediment was 12% or less of the dose and
tended to be lower at higher plant densities. Alkaline hydrolysis in the water near
the surface of macrophytes and phytoplankton is considered to be the main dissipa-
tion process for lambda-cyhalothrin.

7 Summary

Lambda-cyhalothrin is a pyrethroid insecticide used for controlling pest insects in

agriculture, public health, and in construction and households. Lambda-cyhalothrin
is characterized by low vapor pressure and a low Henry’s law constant but by a high
88 L.-M. He et al.

octanol–water partition coefficient (Kow) and high water–solid-organic carbon parti-

tion coefficient (Koc) values. Lambda-cyhalothrin is quite stable in water at pH < 8,
whereas it hydrolyzes to form HCN and aldehyde under alkaline conditions.
Although lambda-cyhalothrin is relatively photostable under natural irradiation,
with a half-life > 3 wk, its photolysis process is fast under UV irradiation, with a
half-life < 10 min. The fate of lambda-cyhalothrin in aquatic ecosystems depends
on the nature of system components such as suspended solids (mineral and organic
particulates) and aquatic organisms (algae, macrophytes, or aquatic animals).
Lambda-cyhalothrin residues dissolved in water decrease rapidly if suspended solids
and/or aquatic organisms are present because lambda-cyhalothrin molecules are
strongly adsorbed by particulates and plants. Adsorbed lambda-cyhalothrin mole-
cules show decreased degradation rates because they are less accessible to break-
down than free molecules in the water column. On the other hand, lambda-cyhalothrin
adsorbed to suspended solids or bottom sediments may provide a mechanism to
mitigate its acute toxicity to aquatic organisms by reducing their short-term bioavail-
ability in the water column. The widespread use of lambda-cyhalothrin has resulted
in residues in sediment, which have been found to be toxic to aquatic organisms
including fish and amphipods. Mitigation measures have been used to reduce the
adverse impact of lambda-cyhalothrin contributed from agricultural or urban runoff.
Mitigation may be achieved by reducing the quantity of runoff and suspended solid
content in runoff through wetlands, detention ponds, or vegetated ditches.

References

Ali MA, Baugh PJ (2003) Sorption-desorption studies of six pyrethroids and mirex on soils using
GC/MS-NICI. Int J Environ Anal Chem 83:923–933.
Amweg EL, Weston DP (2005) Use and toxicity of pyrethroid pesticides in the Central Valley,
California, USA. Environ Toxicol Chem 24:1300–1301.
Amweg EL, Weston DP, Ureda NM (2005) Use and toxicity of pyrethroid pesticides in the Central
Valley, California, USA. Environ Toxicol Chem 24:966–972.
Amweg EL, Weston DP, You J, Lydy MJ (2006) Pyrethroid insecticides and sediment toxicity in
urban creeks from California and Tennessee. Environ Sci Technol 40:1700–1706.
Arts GHP, Guijse-Bogdan LL, Belgers JDM, Van Rhenen-Kersten CH, Van Wijngaarden RPA,
Roessink I, Maund SJ, Van den Brink PJ, Brock TCM (2006) Ecological impact in ditch meso-
cosms of simulated spray drift from a crop protection program for potatoes. Integr Environ
Assess Manag 2:105–125.
Bennett ER, Moore MT, Cooper CM, Smith S, Shields FD, Drouillard KG, Schulz R (2005)
Vegetated agricultural drainage ditches for the mitigation of pyrethroid-associated runoff.
Environ Toxicol Chem 24:2121–2127.
Bondarenko S, Putt A, Kavanaugh S, Poletika N, Gan JY (2006) Time dependence of phase dis-
tribution of pyrethroid insecticides in sediment. Environ Toxicol Chem 25:3148–3154.
Bouldin JL, Farris JL, Moore MT Jr, Stephens WW, Cooper CM (2005) Evaluated fate and effects
of atrazine and lambda-cyhalothrin in vegetated and unvegetated microcosms. Environ Toxicol
20:487–498.
Bouldin JL, Farris JL, Moore MT, Smith JS, Cooper CM (2006) Hydroponic uptake of atrazine
and lambda-cyhalothrin in Juncus effusus and Ludwigia peploides. Chemosphere
65:1049–1057.
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 89

Bradbury SP, Coats JR (1989) Toxicokinetics and toxicodynamics of pyrethroid insecticides in

fish. Environ Toxicol Chem 8:373–380.
Burken JG, Schnoor JL (1997) Uptake and metabolism of atrazine by poplar trees. Environ Sci
Technol 31:1399–1406.
Burr SA, Ray DE (2004) Structure-activity and interaction effects of 14 different pyrethroids on
voltage-gated chloride ion channels. Toxicol Sci 77:341–346.
Cavas T, Ergene-Gozukara S (2003) Evaluation of the genotoxic potential of lambda-cyhalothrin
using nuclear and nucleolar biomarkers on fish cells. Mutat Res/Genet Toxicol Environ
Mutagen 534:93–99.
CDPR (2006) California Department of Pesticide Regulation Pesticide Use Database.
CDPR (2007) Pesticide chemical database.
Cleugh ES, Milner DJ (1994) Isomerization process. http://wwwpatentstormus/patents/5334744-
descriptionhtml.
Cycon M, Piotrowska-Seget Z, Kaczynska A, Kozdroj J (2006) Microbiological characteristics of
a sandy loam soil exposed to tebuconazole and lambda-cyhalothrin under laboratory condi-
tions. Ecotoxicology 15:639–646.
European-Commission (2001) Review report for the active substance lambda-cyhalothrin. 7572/
VI/97-final.25January2001.http://ec.europa.eu/food/plant/protection/evaluation/existactive/list1-24_en.pdf.
Farmer D, Hill IR, Maund SJ (1995) A comparison of the fate and effects of two pyrethroid
insecticides (lambda-cyhalothrin and cypermethrin) in pond mesocosms. Ecotoxicology
4:219–244.
Fernandez-Alvarez M, Sanchez-Prado L, Lores M, Llompart M, Garcia-Jares C, Cela R (2007)
Alternative sample preparation method for photochemical studies based on solid phase micro-
extraction: synthetic pyrethroid photochemistry. J Chromatogr A Adv Sample Prep
1152:156–167.
Forster B, Garcia M, Francimari O, Rombke J (2006) Effects of carbendazim and lambda-cyha-
lothrin on soil invertebrates and leaf litter decomposition in semi-field and field tests under
tropical conditions (Amazonia, Brazil). Eur J Soil Biol 42:S171–S179.
Frampton GK, Jansch S, Scott-Fordsmand JJ, Rombke J, Van den Brink PJ (2006) Effects of pes-
ticides on soil invertebrates in laboratory studies: a review and analysis using species sensitiv-
ity distributions. Environ Toxicol Chem 25:2480–2489.
Gan J, Yang W, Hunter W, Bondarenko S, Spurlock F (2006) Bioavailability of pyrethroids in
surface aquatic systems. http://wwwcdprcagov/docs/sw/presentations/JGan_pyrethroids
101105pdf.
Gu BG, Wang HM, Chen WL, Cai DJ, Shan ZJ (2007) Risk assessment of lambda-cyhalothrin on
aquatic organisms in paddy field in China. Regul Toxicol Pharmacol 48:69–74.
Gupta S, Handa SK, Sharma KK (1998) A new spray reagent for the detection of synthetic pyre-
throids containing a nitrile group on thin-layer plates. Talanta 45:1111–1114.
Hadfield ST, Sadler JK, Bolygo E, Hill S, Hill IR (1993) Pyrethroid residues in sediment and
water samples from mesocosm and farm pond studies of simulated accidental aquatic expo-
sure. Pestic Sci 38:283–294.
Hamer MJ, Goggin UM, Muller K, Maund SJ (1999) Bioavailability of lambda-cyhalothrin to
Chironomus riparius in sediment-water and water-only systems. Aquat Ecosys Health Manag
2:403–412.
Hand LH, Kuet SF, Lane MCG, Maund SJ, Warinton JS, Hill IR (2001) Influences of aquatic
plants on the fate of the pyrethroid insecticide lambda-cyhalothrin in aquatic environments.
Environ Toxicol Chem 20:1740–1745.
Heckmann LH, Friberg N (2005) Macroinvertebrate community response to pulse exposure with
the insecticide lambda-cyhalothrin using in-stream mesocosms. Environ Toxicol Chem
24:582–590.
Henderson KL, Belden JB, Coats JR (2007) Mass balance of metolachlor in a grassed phytoreme-
diation system. Environ Sci Technol 41:4084–4089.
Hill BD, Inaba DJ (1991) Dissipation of lambda-cyhalothrin on fallow vs. cropped soil. J Agric
Food Chem 39:2282–2284.
90 L.-M. He et al.

Laabs V, Amelung W, Pinto A, Altstaedt A, Zech W (2000) Leaching and degradation of corn
and soybean pesticides in an Oxisol of the Brazilian Cerrados. Chemosphere 41:1441–1449.
Laskowski DA (2002) Physical and chemical properties of pyrethroids. Rev Environ Contam
Toxicol 174:49–170.
Lawler SP, Dritz DA, Godfrey LD (2003) Effects of the agricultural insecticide lambda-cyhalothrin
(Warrior (™) ) on mosquitofish (Gambusia affinis). J Am Mosq Control Assoc 19:430–432.
Lawler SP, Dritz DA, Christiansen JA, Cornel AJ (2007) Effects of lambda-cyhalothrin on mos-
quito larvae and predatory aquatic insects. Pest Manag Sci 63:234–240.
Leistra M, Zweers AJ, Warinton JS, Crum SJ, Hand LH, Beltman WH, Maund SJ (2004) Fate of
the insecticide lambda-cyhalothrin in ditch enclosures differing in vegetation density. Pest
Manag Sci 60:75–84.
Maund SJ, Hamer MJ, Warinton JS, Kedwards TJ (1998) Aquatic ecotoxicology of the pyrethroid
insecticide lambda-cyhalothrin: considerations for higher-tier aquatic risk assessment. Pestic
Sci 54:408–417.
Mertens J, Vervaeke P, Meers E, Tack FMG (2006) Seasonal changes of metals in willow (Salix
sp.) stands for phytoremediation on dredged sediment. Environ Sci Technol 40:1962–1968.
Milam CD, Bouldin JL, Farris JL, Schulz R, Moore MT, Bennett ER, Cooper CM, Smith S (2004)
Evaluating acute toxicity of methyl parathion application in constructed wetland mesocosms.
Environ Toxicol 19:471–479.
Montes-Bayon M, Yanes EG, Ponce de Leon C, Jayasimhulu K, Stalcup A, Shann J, Caruso JA
(2002) Initial studies of selenium speciation in Brassica juncea by LC with ICPMS and ES-
MS detection: an approach for phytoremediation studies. Anal Chem 74:107–113.
Moore MT, Bennett ER, Cooper CM, Smith S, Shields FD, Milam CD, Farris JL (2001) Transport
and fate of atrazine and lambda-cyhalothrin in an agricultural drainage ditch in the Mississippi
Delta, USA. Agric Ecosyst Environ 87:309–314.
Oros DR, Werner I (2005) Pyrethroid Insecticides: An Analysis of Use Patterns, Distributions,
Potential Toxicity and Fate in the Sacramento-San Joaquin Delta and Central Valley. White
Paper for the Interagency Ecological Program. SFEI Contribution 415. San Francisco Estuary
Institute, Oakland, CA.
Oudo H, Hansen HC (2002) Sorption of lambda-cyhalothrin, cypermethrin, deltamethrin and fen-
valerate to quartz, corundum, kaolinite and montmorillonite. Chemosphere 49:1285–1294.
PAN (2007) PAN Pesticides Database, Chemicals. http://www.pesticideinfo.org/List_Chemicals.jsp.
Accessed July 20, 2007.
Reichenberger S, Amelung W, Laabs V, Pinto A, Totsche KU, Zech W (2002) Pesticide displace-
ment along preferential flow pathways in a Brazilian Oxisol. Geoderma 110:63–86.
Robson MJ and Crosby J (1984) Insecticidal product and preparation thereof. European Patent
Office. Patent Number EU 106469. UK.
Roessink I, Arts GHP, Belgers JDM, Bransen F, Maund SJ, Brock TCM (2005) Effects of lambda-
cyhalothrin in two ditch microcosm systems of different trophic status. Environ Toxicol Chem
24:1684–1696.
Ruzo LO, Krishnamurthy VV, Casida JE, Gohre K (1987) Pyrethroid photochemistry: influence
of the chloro(trifluoromethyl)vinyl substituent in cyhalothrin. J Agric Food Chem
35:879–883.
Schwarzenbach RP, Gschwend PM, Imboden DM (1993) Environmental Organic Chemistry.
Wiley, New York.
Shafer TJ, Meyer DA (2004) Effects of pyrethroids on voltage-sensitive calcium channels: a criti-
cal evaluation of strengths, weaknesses, data needs, and relationship to assessment of cumula-
tive neurotoxicity. Toxicol Appl Pharmacol 196:303–318.
Siciliano SD, Goldie H, Germida JJ (1998) Enzymatic activity in root exudates of Dahurian wild
rye (Elymus dauricus) that degrades 2-chlorobenzoic acid. J Agric Food Chem 46:5–7.
Spurlock F (2006) Synthetic pyrethroids and California surface water: use patterns, properties,
and unique aspects. http://wwwcdprcagov/docs/sw/swposters/spurlock_acs06pdf.
Starner K (2007) Data queried from the Department of Pesticide Regulation Surface Water
Monitoring Database.
Environmental Chemistry, Ecotoxicity, and Fate of Lambda-Cyhalothrin 91

Syngenta (2007) KARATE. http://wwwsyngentacom/en/products_services/karate_pageaspx.

Tariq MY, Afzal S, Hussain I (2006) Degradation and persistence of cotton pesticides in sandy
loam soils from Punjab, Pakistan. Environ Res 100:184–196.
Tomlin CDS (ed) (2000) The Pesticide Manual, 12th Ed. British Crop Protection Council,
Farnham, UK.
USDA (2007) USDA-ARS Pesticide Properties Database: http://www.ars.usda.gov/Services/docs.
htm?docid=14199. Accessed July 20, 2007.
USEPA (2007) ECOTOX database. http://cfpubepagov/ecotox/quick_queryhtm.
Van Wijngaarden RPA, Cuppen JGM, Arts GHP, Crum SJH, van den Hoorn MW, Van den Brink
PJ, Brock TCM (2004) Aquatic risk assessment of a realistic exposure to pesticides used in
bulb crops: a microcosm study. Environ Toxicol Chem 23:1479–1498.
Van Wijngaarden RPA, Brock TCM, Van den Brink PJ (2005) Threshold levels for effects of
insecticides in freshwater ecosystems: a review. Ecotoxicology 14:355–380.
Wang S, Kimber SWL, Kennedy IR (1997) The dissipation of lambda-cyhalothrin from cotton
production systems. J Environ Sci Health B B32:335–352.
Wang W, Cai DJ, Shan ZJ, Chen WL, Poletika N, Gao XW (2007) Comparison of the acute toxic-
ity for gamma-cyhalothrin and lambda-cyhalothrin to zebra fish and shrimp. Regul Toxicol
Pharmacol 47:184–188.
Wendt-Rasch L, Van den Brink PJ, Crum SJH, Woin P (2004) The effects of a pesticide mixture
on aquatic ecosystems differing in trophic status: responses of the macrophyte Myriophyllum
spicatum and the periphytic algal community. Ecotoxicol Environ Saf 57:383–398.
Weston DP, You JC, Lydy MJ (2004) Distribution and toxicity of sediment-associated pesticides
in agriculture-dominated water bodies of California’s Central Valley. Environ Sci Technol
38:2752–2759.
Weston DP, Holmes RW, You J, Lydy MJ (2005) Aquatic toxicity due to residential use of pyre-
throid insecticides. Environ Sci Technol 39:9778–9784.
Wild E, Dent J, Thomas GO, Jones KC (2005) Direct observation of organic contaminant uptake,
storage, and metabolism within plant roots. Environ Sci Technol 39:3695–3702.
Zhou JL, Rowland S, Mantoura RFC (1995) Partition of synthetic pyrethroid insecticides between
dissolved and particulate phases. Water Res 29:1023–1031.