BRIEF REVIEW OF PYRETHROID INSECTICIDE: CHEMICAL STRUCTURE AND

MODE OF ACTION
Godfred BEMPAH
bempahgodfred@yahoo.com

ABSTRACT
The chemical composition of natural product have inspired several studies, although few have

focused on natural insecticides in recent times. Pyrethroid insecticide as a special natural product,

possesses beneficial characteristics for Integrated Pest Management (IPM). The chemistry

of pyrethroid insecticide emphasizes it to be madeup of an acid moiety, a central ester bond, and

an alcohol moiety. Most pyrethroids basically occur in the form of stereoisomeric substance (trans

and cis). Two main types, type I and type II cyano groups, of pyrethroids are revealed based on

toxicity level and alcohol substituent in the molecule. The neurotoxicity actions of pyrethroids is

by attacking the central nervous system of an insect, where the voltage-gated sodium channels

occur. Pyrethroids tends to be effective at low temperatures than high temperatures and easily

broken down by acidic substances. The review establishes Pyrethroid insecticides to contain

chemical compounds that makes it potent at controlling insects.

INTRODUCTION
A natural product from a bigger perspective refers to chemical compounds obtained from living

organism existing in nature (https://www.nature.com/articles/nchembio0707-351). It also covers

substances linked to commercial production of natural sources. In the scientific study of organic

chemistry, natural products can also be referred to as products manufactured by application of

primary and secondary metabolism pathways to extract organic products from organisms that have

life (Hanson, 2003). Natural products most a times have wide range of benefit (Li & Vederas,

2009). For example, natural insecticides aims at killing, repelling, and/or interfering with the

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activities of insect pests that have damaging behaviour. One of such natural commercially

produced substances is pyrethroids. Although natural products have inspired several previous

studies, few have focused on pyrethroids with scattered information. Need for progressive review

of literature to provide current information to abridge specific knowledge gap relating the

chemistry and actions of insecticides as well as its effect on physiological processes in the host is

valued.

The focus of this review is on the chemistry, mode of action and types of Pyrethroid insecticides.

The chemical structures of the various components is highlighted, significantly is the illustration

of structure-toxicity linkage of the commercial molecules. Pyrethroid insecticides is discussed

because it possesses beneficial characteristics for Integrated Pest Management (IPM). The

discussion considers mode of action of this insecticide limiting the spotlight on interactions with

specific targets, culminating in toxicity expressed in insects.

Pyrethroids are insecticidal substances widely used, accounting for 25% of the insecticide business

globally (Shafer, Meyer and Crofton, 2005). They are natural pyrethrin derived from the flowers

and seed of Chrysanthemum cinerariaefolium, and produced in commercial quantities (Sorgob and

Vilanova, 2002; Shafer, Meyer and Crofton, 2005). Several synthetic pyrethroids that have been

manufactured include but not limited to bifenthrin, cyfluthrin, cypermethrin, deltamethrin,

esfenvalerate, lambda-cyhalothrin, imiprothrin, permethrin, prallethrin, resmethrin, tefluthrin,

tetramethrin. They have high fat solubility and also degrade in sunlight more easily.

The chemistry of pyrethroid insecticide emphasizes it to be composed of acid moiety, central ester

bond, and alcohol moiety. Fundamentally, two chiral carbons form the acid moiety,

hence pyrethroids basically occur in the form of stereoisomeric substance (transisomers-

“trans” and cisisomers-“cis”). Moreover, the alcohol moiety of other identified pyrethroids

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contain a chiral carbon, resulting in a number of eight distinct stereoenantiomers (Fig 1).

According to Casida et al., 1983, the cisisomers are typically high in toxicity compared with

the transisomers, making impacts of pyrethroids on sodium channels more stereospecific.

Two main types, type I and type II groups, of pyrethroids are revealed based on toxicity level and

alcohol substituent in the molecule. A classical factor that differentiates type I from type II groups

is existence of a cyano group in Type II at α carbon structure of the alcohol moiety (Fig. 1). The

chemical structure of type 1 group is more extensive containing descyano-3-phenoxybenzyl or

other alcohols, especially the influx of halogenated alcohols such as tefluthrin have improved

stability of chemical constituents of pyrethroids. Whereas the characteristics of Type II are more

barely defined, explicitly consisting of an a-cyano-3-phenoxybenzyl alcohol (Fig. 1),

Figure 1: Chemical structure of Pyrethroids; Type I and Type II groups

Source: Bloomquist, 2009

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Thus, Type I groups contain esters that are of both primary and secondary alcohols, whiles Type

II contains only secondary alcohol. According to Mani, Gokulakrishnan, and Sadiq, 2017, Type II

groups are more effective than Type I groups.

The initial effect of Pyrethroids results from its intoxication on the sodium channel of cells

(Ramaekers et al., 2014). Neurons in the central and peripheral nervous systems have a

membranous voltage not exceeding -60 mV on the internally (Fig. 2). The cells get excited with

the opening and closing of Na+ channels through the actions pyrethroids (Conley and Brammar,

2009). This action is sustained down the axon until it gets to the nerve terminal, where it triggers

the discharge of chemical transmitters. The duration of this action is much longer for type

II pyrethroids than for type I due to differences in the degree of physiological effect (Fig 2).

The neurotoxicity actions of Pyrethroids is by attacking the central nervous system of an insect,

where the voltage-gated sodium channels are affected thereby paralyzing the muscle and as a result

the insects die (Fig. 2). Toxicity is more pronounced in insects than in mammals because acid

concentration in mammals can easily break down Pyrethroids. Additionally, Pyrethroids

effectively attracts heavily with sodium channel at low temperatures (insect’s temperature at 25°C)

than at high temperatures (mammal’s temperature at 37°C)

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Figure 2: The Nerve impulse, Neuro-muscular transmission and the action of insecticides.
Source: Bloomquist, 2009

CONCLUSION
Pyrethroid insecticide as a special natural product, possesses beneficial characteristics for

Integrated Pest Management (IPM). They are extracted from natural sources and produced in

commercial quantities. The chemistry of pyrethroid insecticide emphasizes it to be composed of

acid moiety, central ester bond, and alcohol moiety. Fundamentally, two chiral carbons form the

acid moiety, hence pyrethroids basically occur in the form of stereoisomeric substance

(transisomers- “trans” and cisisomers-“cis”). Two main types, type I and type II groups, of

pyrethroids are revealed based on toxicity level and alcohol substituent in the molecule. A classical

factor that differentiates type I from type II groups is existence of a cyano group in Type II at α

carbon structure of the alcohol moiety. The neurotoxicity actions of Pyrethroids is by attacking the

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central nervous system of an insect, where the voltage-gated sodium channels are affected thereby

paralyzing the muscle and as a result the insects die. Toxicity is more pronounced in insects than

in mammals because acid concentration in mammals can easily break down pyrethroids.

Additionally, pyrethroids effectively attracts heavily with sodium channel at low temperatures

(insect’s temperature at 25°C). The review establishes Pyrethroid insecticides to contain chemical

compounds that makes it potent at controlling insects.

REFERENCE

Bloomquist, J. R. (2009) Insecticides: Chemistries and Characteristics. From Radcliffe’s IPM

World Textbook, University of Minnesota, Minneapolis.

http://ipmworld.umn.edu/chapters/bloomq.htm

Casida, J. E., Gammon, D. W., Glickman, A.H., & Lawrence, L.J. (1983). Mechanisms of selective

action of pyrethroid insecticides. Annual Review, Pharmacology and Toxicology, 23:413-

438.

Conley, E. C. & Brammar, W. J. (2009). Diversity and Structures of Ion Channels. In: Leuchtag

H.R. (eds) Voltage-Sensitive Ion Channels. Springer, Dordrecht

From Radcliffe’s IPM World Textbook, University of Minnesota, Minneapolis.

Hanson, J. R. (2003). Natural Products: the Secondary Metabolite. Cambridge: Royal Society of

Chemistry. ISBN 0-85404-490-6.

Li, J. W. & Vederas, J. C (2009). "Drug discovery and natural products: end of an era or an endless

frontier. Science, 325 (5937): 161–5.

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Mani, V. M., Gokulakrishnan, A., & Sadiq, A. M. M. (2017). Molecular Mechanism of

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https://www.nature.com/articles/nchembio0707-351 accessed on 23/12/19