FORMULATION

IMPROVING INSECTICIDES THROUGH ENCAPSULATION

Bob Perrin from Zeneca Agrochemicals at Jealotts Hill International Research Station discusses the controlled
delivery of insecticides achieved using capsule suspension formulations

Introduction by researching and developing a range of formulations

It has traditionally been herbicides rather than insecticides
whose intrinsic biological activity or selectivity has been
optimised through formulation. The use of adjuvants to
increase the spread of foliar deposits or cuticular uptake are
two typical examples that have met with commercial
success. Most insecticides are produced as emulsifiable
concentrates, suspension concentrates, wettable granules or
wettable powders, depending on the properties of the active
ingredient (a.i.) and the target market, and provide cost-
effective pest control along with convenience of handling
and compatibility with spray equipment. Past attempts to
improve insecticide formulations have usually centred
around greater rainfastness or photostability, rather than
reduced environmental risk or the complex issues related to
uptake of dried deposits of a contact-acting compound from
a plant surface, systemic movement of a stomach-acting
compound or differential exposure to pests and natural
enemies.
In the 1990s, there has been an increasing demand for
insecticide products which are not only more active gram for
gram, but safer to both operators and the environment,
especially aquatic habitats. Registration schemes favour
safer and more selective crop protection products, which can
be achieved either through the intrinsic properties of the
chemical itself, or through ways in which the effect is
delivered. The common use of aromatic solvents is under
scrutiny for several reasons, including the so-called estrogen
mimic effect, and the agrochemical industry has responded
which reduce both operator hazards and risks to natural
habitats. Table 1 lists the range of insecticide formulations
currently available.
Encapsulation technology
Many novel ideas are generated at the formulater’s
laboratory bench (Woods, 1999), some of which are very
exciting biologically, but only those which meet the strict
criteria of official registration agencies and promise
commercial viability appear in the market place. Of recent
developments, capsule suspensions (CS) have particularly
appealing prospects for the future (Scher et al., 1998).
What are microcapsules?
A microcapsule is a 10–3 m to 10–9 m diameter particle,
composed of a core material and an outer wall (Tsuji, 1993).
Several methods of producing these are available, but the
use of a process known as interfacial polymerisation based
on the condensation of isocyanate or aminoplast monomers
or pre-polymers allows the highest pesticide loading and the
most cost-effective manufacture. The outer wall isolates the
core material and protects it from environmental
degradation and interaction with other materials; it should
have the following features:
● not react with pesticides
● not be harmful to the environment

Table 1. Features of the major types of insecticide formulations

TYPE FEATURES

WETTABLE POWDER (WP) bulky, dusty, inconvenient,

more hazardous to manufacture than liquids.
WETTABLE GRANULE (WG) low dust, low solvent, suitable for soluble packs and unit dosing, some dispersion problems. Less
easy to measure than liquids.
EMULSIFIABLE CONCENTRATE (EC) simple, robust, versatile, proven, flammable, high solvent content seen as a pollutant.
SUSPENSION CONCENTRATE (SC) simple, robust, generally water-based, not suited to many a.i.’s, some sedimentation problems.
EMULSION IN WATER(EW) water-based, low solvent, some colloidal instability problems, less toxic than EC’s.
MICROEMULSION expensive, chemical stability problems.
CAPSULE SUSPENSION (CS) water-based, low solvent, robust, cost-effective, less toxic than EC’s.
DRY MICROCAPSULE advantages of a CS, less bulky to store than CS or EC.
TABLET convenient, unit dosing, easy to package, good image, some dispersion problems.
GEL good image, suitable for soluble packs and unit dosing, intermediate properties of liquids and
solids.

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● be stable in storage
● be manufactured and processed easily
● be economical
● have suitable physicochemical properties to provide the
required release behaviour of the core materials
The core materials, e.g. an insecticide, are thus designed to
be released in a controlled fashion. Depending on their
particular design, microcapsule formulations can provide
combinations of the following characteristics :
● improved residual activity
● longer application intervals
● reduction in application dosage
● stabilisation of core ingredients against environmental
degradation (light, air, humidity, microorganisms etc.)
● masking of odour
● reduction in spray drift
● less impact on non-target organisms
● better rainfastness
● improved uptake and systemic movement in plants
● less phytotoxicity
● constant or delayed biological effect
● reduced absorption on porous surfaces
● improved mammalian toxicological profile
● reduced environmental pollution
● reduced volatilisation and leaching
● improved compatibility with packaging materials
● safer storage due to reduced flammability
● seed coating with liquid insecticide without using an
absorbent carrier
Microcapsules are usually formulated as a slurry in which
microcapsules are suspended in water (CS formulations).
Various surfactants and suspending agents are added to
maintain the stability of the formulation. Microcapsules can
also be formulated as dry powders, which can be used for
FORMULATION
Figure 1. DEMAND CS capsules on
cement 10 weeks after application.
Magnification x 1400.
bait, dust or wettable powder
finished products. The rest of this
article refers to the water-based CS
formulations.
Microcapsule release
Release rates are governed by the
capsule particle size, the thickness of
the wall and the permeability of the
wall. Small particles with thin walls
and low cross-linking density allow
the fastest possible release, while
large particles with thick walls and
high cross-linking have the slowest
release. The most practical way to
change release rates over orders of
magnitude is to vary wall perme-
ability through its cross-linking
density and chemical composition.
One product concept is to have variations on these
parameters in the same container, for example, a proportion
that release very rapidly for quick knockdown of pests, and
a proportion that release slowly to provide residual activity.
An active ingredient and a synergist can also be made
compatible through different release rates.
Use of encapsulation technology
With their controlled release of active ingredient to a greater
or lesser degree, microcapsules have potential use in public
health and animal health applications, such as control of
disease vectors through treatment of building surfaces. The
extended residual activity achieved through encapsulation,
however, can also find application in agricultural products.
Modern capsules essentially bring the added potential to
“dial up” the properties of the product which are required
for any particular outlet, all the way from very rapid release
once spray droplets reach their target, through release which
is triggered by a specific environmental cue, such as pH,
temperature or light, to delays of weeks or months governed
by slow biological degradation of the capsule material. Not
only release rate can be engineered to fit the purpose at
hand, but the polymer wall can be used to incorporate other
features into the product, such as ultra-violet protection,
substrate affinity, compatibility of several a.i.’s, colour
coding etc.
Microcapsules in public health
DEMAND CS capsules (Figure 1) have a volume median
diameter (VMD) of approximately 12 microns and consist
of a polyurea wall formed by an in situ interfacial condensa-
tion process (Scher et al., 1998). The capsule wall is strongly
cross-linked with a high ratio of polymethylene-polyphenol-
isocyanate (PMMPI): toluene di-isocyanate (TDI), which
confers a relatively low permeability to the capsule contents,
namely the active ingredient, lambda-cyhalothrin, dissolved
Pe s t i c i d e O u t l o o k – A p r i l 2 0 0 0 69
 FORMULATION
in a small amount of aromatic oil. Release of a.i. is very
limited after spray deposits have dried on a substrate such as
cement or wood, diffusion through the capsule wall being
initiated by pick up of capsules on to the lipophilic legs or
bodies of insects. Intact capsules have been observed by
microscopy on the bodies of cockroaches, flies and ants that
make contact with deposits during walking or resting
(Figure 2) – the so-called ‘trampling effect’. Adult male
Blattella germanica cockroaches exposed for one minute to
an unglazed tile treated with DEMAND CS at a rate of 30
mg a.i. m–2 picked up a mean of 700 capsules, many times
the lethal dose, which may contribute to the observed
improvement in efficacy against resistant strains of
cockroaches using microencapsulated formulations rather
than emulsifiable concentrates (Wege et al., 1999).
In public health markets, there are other advantages to
inhibiting the initial availability of the active ingredient. For
example, the early symptoms of toxicity of pyrethroids can
result in flushing, that is the expulsion of cockroaches from
their harborages before a lethal dose is acquired. CS formu-
lations generally reduce flushing compared to EC and WP
formulations. Similarly, a CS formulation of lambda-
cyhalothrin allows fire ants to be killed before any repellent
effect occurs.
Microcapsules in agriculture
In contrast to the requirements for months of persistence on
inert surfaces when controlling flies, mosquitoes and
cockroaches, agricultural formulations must provide a rapid
knockdown effect, especially if the pest is a transmitter of
plant viruses, as well as residual activity for several days or
weeks depending on crop growth rates and the pest in
question. Fast-release capsules of lambda-cyhalothrin,
marketed under the trade name “Zeon Technology”, are
made by an in-situ interfacial polymerisation where the
70 Pe s t i c i d e O u t l o o k – A p r i l 2 0 0 0
Figure 2. Demand CS capsule on a
cockroach leg. Magnification x 1500.
monomers reside only in the oil phase
and produce a very efficient
asymmetric polyurea wall membrane
(Perrin et al., 1998). Capsules have a
mean diameter (VMD) of 2.5 microns
and an ultra-violet absorber is incor-
porated within the core. Active
ingredient remains within the capsules
in the container, the spray tank and
the spray droplets during atomisation,
offering greater protection to users.
Once capsules lose their water barrier
on a plant surface or insect cuticle,
diffusion begins immediately and is
thought to be complete within a few
hours (Figure 3). Insects pick up the
released contents from the sprayed
surface rather than from intact
capsules. This results in a very similar
biological effect, whether on target or
non-target organisms, to an emulsifiable
concentrate, whilst significantly improving the toxicological
profile with respect to eye and skin irritation.
Zeon Technology has been widely evaluated for pest
control in major crops around the world, and provides the
same, and in some cases better, control than seen previously
with emulsifiable concentrates. It is registered for sale in
several countries, including the UK, and is the first
pyrethroid product to be endorsed by the British Beekeepers
Association. There is potential to produce a wide range of
active ingredient strengths and mean capsule sizes, mixtures
of different active ingredients, and to co-formulate with
synergists or other agents to improve knockdown or residual
activity. Water-based microcapsules also lend themselves to
incorporation in solid carriers for ease of handling or
packaging.
The future for encapsulation
One promising encapsulation technology is triggered (or
stimuli-sensitive) release of capsule contents, where the
trigger to rupture the wall can be something that achieves
high specificity of insecticidal effect, such as the alkaline gut
of lepidopteran larvae like cotton bollworm. This has the
beauty of preventing exposure of chemical to predators and
parasites, important components of IPM programmes, but
limiting the application to pests which eat treated plant
tissue and thus take capsules into their gut. Risks to aquatic
habitats could also be minimised through thick-walled
triggered capsules. The ultimate trigger to release a toxin is
conceivably the presence of the insect or its damage to the
crop. Insect saliva or plant defence chemicals, such as
salicylic and jasmonic acids, released in response to feeding
by pests would be a highly specific trigger that confined
exposure to those times when, and those locations where
crop protection is needed. Another situation that would

benefit from trigger technology is the use of baits for ants
and cockroaches. These insects are usually repelled by trace
amounts of chemicals like pyrethroids, so a system which
locks up the insecticide tightly until bait is ingested, would
improve the administration of lethal doses. Stimuli-sensitive
polymers to achieve on-demand delivery of active
ingredients have already found considerable use in non-agri-
cultural industries, and should play a valuable part in crop
protection in the future (Beestman, 1996).
Insecticidal action is usually required only at certain
vulnerable periods, when a crop is at risk of yield loss or
when disease vectors are active, and beyond this period the
chemical should degrade rapidly before constituting a food
residue or soil leaching hazard. Enzymes or micro-organisms
could conceivably be incorporated in a separate
compartment alongside the active ingredient, and timed to
release when required to eliminate any remaining, unwanted
a.i. (Beestman, 1996; Perrin, 1997).
Delivering some of these more sophisticated effects in a
cost-effective and reliable manner is a considerable
challenge, but the controlled release characteristics of micro-
capsule formulations, coupled with their improved toxico-
logical, ecotoxicological and environmental profiles, should
ensure for them a bright future.
References
Beestman, G. W. (1996) Emerging Technology: The Bases For New
Generations of Pesticide Formulation. In: Pesticide Formulation
Figure 3. Dried deposit of Zeon
Technology capsules on an inert
surface, showing broken and partially
emptied capsules. Magnification x 4500.
and Adjuvant Technology, edited by C. L. Foy and D. W.
Pritchard, pp 43–68, CRC Press, London.
Perrin, R. M. (1997) Crop Protection: taking stock for the new
millennium. Crop Protection 16, 449–456.
Perrin, R. M.; Wege, P. J.; Foster, D. G.; Bartley, M. R.; Browde, J.;
Rehmke, A.; Scher, H. (1998). Fast release capsules : a new
formulation of lambda-cyhalothrin. Proceedings British Crop
Protection Conference – Pests and Diseases 1998 1, 43–48.
Scher, H.; Rodson, M.; Lee, K. S. (1998) Microencapsulation of
pesticides by interfacial polymerisation utilising isocyanate or
aminoplast chemistry. Pesticide Science 54, 394–400.
Tsuji, K. (1993) Microcapsules of insecticides for household use.
Pesticide Outlook 4(3), 36.
Wege, P. J.; Hoppe, M. A.; Bywater, A. F.; Weeks, S. D.; Gallo, T.
S. (1999) A microencapsulated formulation of lambda-
cyhalothrin. Proceedings of the 3rd International Conference
on Urban Pests 1999, 301–310.
Woods, T. S. (1999) The formulator’s toolbox - product forms for
modern agriculture. In : Pesticide Chemistry and Bioscience :
The Food–Environment Challenge, edited by G. T. Brooks and
T. R. Roberts, pp 120–133, Royal Society of Chemistry,
Cambridge.
Bob Perrin has been a senior entomologist with Zeneca Agrochemi-
cals for 22 years and is responsible for the laboratory and field
evaluation of all novel insecticide formulations. In recent years, he
has co-ordinated extensive testing of Zeon Technology and is
currently researching the application of triggered release capsules of
lambda-cyhalothrin.
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