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Malathion Organophosphate Insecticide in Chemistry

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What is Malathion Structure Formula Preparation Uses and Toxicity

Malathion is a broad-spectrum organophosphate acaricide and insecticide also known as mercaptothion, maldison, and carbophos (that is used to kill mites and ticks). Considerably less toxic to humans compared to parathion, malathion can be suited for the control of garden and household insects and is essential in the control of boll weevils, mosquitoes, lice, and fruit flies.


Properties

Malathion is given as a colourless yellow-brown liquid having a characteristic unpleasant odour. Malathion iupac id is 4004. Generally, it can be prepared by combining O and O-dimethyl phosphorothioate with diethyl maleate. It is also soluble in most of the organic solvents except paraffin hydrocarbons. Practically, it insoluble in water and is readily decomposed by alkalies. The malathion chemical acts by binding to the enzyme acetylcholinesterase (AChE) at nerve endings, causing the neurotransmitter acetylcholine (ACh) to be disrupted, eventually leading to death.


Mechanism of Action

Malathion is a compound that inhibits acetylcholinesterase, which is a large family of chemicals. When this is injected into the target organism, it binds irreversibly to the serine residue in the cholinesterase enzyme's active catalytic site. The phosphoester group is then tightly bound to the cholinesterase and irreversibly deactivates the enzyme, resulting in a rapid build-up of acetylcholine at the synapse.


Production Method

Malathion can be produced by the addition of dimethyl dithiophosphoric acid to either diethyl fumarate or diethyl maleate. The compound is chiral but can be used as a racemate.


Mix Ratio for 55% Malathion for Killing Bedbugs

Generally, while malathion is considered as an exterior pesticide, there are a few formulations, which are labelled interior use, with certain label restrictions. In the U.S.A., the product is not labelled at all for the treatment of bedbugs. The other issue with malathion is the fact that, generally, it can be sold as a malathion oil emulsion and holds a nasty odour. Malathion, that being said, is still considered as an effective treatment of malathion insecticide against bedbugs that have developed a tolerance to the pyrethrin and pyrethroid in a few areas.


In the United States, the last labelled use for bedbug control happened in 1965, a time when lindane, chlordane, D.D.T., and other insecticides were in wide use. At that time, the label suggested a concentration ranging from 0.5% to 1.0%, which would be achieved by mixing a single ounce ranging from 55% with 50–100 ounces of water (also, kerosene was a listed vehicle for malathion, but certainly it should not be used inside the home).


There are many other malathion insecticides, which are considered more appropriate for bedbug control, and they should be readily available for purchases either at hardware or home supply stores. The other suggested treatment is using the ethanol diluted in water is as a topical treatment, but it kills only bedbugs which are sprayed directly with it, and after it dries, it does not have a residual effect.


Most of the websites that cover the bedbug's information recommend hiring a professional pest control company to treat the premises for bedbugs since the local populations tend to develop some resistance to chemical treatment quickly and fairly.


Malathion Uses

Let us see some of the malathion insecticide uses.


Malathion Pesticide Use

Malathion is given as a pesticide, which may be used widely in residential landscaping, agriculture, in public health pest control programs such as mosquito eradication, and also in the public recreation areas. And, in the U.S., it is known to be the most commonly used organophosphate insecticide.


In the 1980s, a malathion mixture containing corn syrup was used to battle the Mediterranean fruit fly in California and Australia. Whereas, in the United States and Canada, starting in the early 2000s, malathion was sprayed in several cities to combat the West Nile virus.


Malathion was also used over the last two decades regularly during the summer to kill mosquitoes. However, homeowners were allowed to exempt their properties in the case if they chose. Today, Winnipeg is the only major city in Canada with a program of ongoing malathion adult-mosquito-control.


Medical Use

In low doses (0.5% preparations), malathion can be used as a treatment for:

  • Body lice and head lice. Malathion is also approved by the United States Food and Drug Administration for the treatment of pediculosis. It is effectively claimed to kill both the adult lice and eggs, but in fact, it has been shown in the United Kingdom, studies to be only 36 percent effective on the head lice and less so on their eggs. This specific low efficiency was observed when malathion was applied to lice found on schoolchildren in the Bristol region of the United Kingdom, and it is believed by some to be caused by the lice developing resistance to malathion.

  • Scabies

Some of the preparations of malathion include Prioderm, Derbac-M, Quellada-M, and Ovide.


Toxicity

Malathion is more highly toxic to the bees and other aquatic invertebrates, beneficial insects, and a few species of fish, notably largemouth and bluegill bass. Also, it is of moderate toxicity to the birds.

FAQs on Malathion Organophosphate Insecticide in Chemistry

1. What is malathion in chemistry?

Malathion is an organophosphate insecticide with the molecular formula C10H19O6PS2. It is a phosphorus-containing organic compound used to control insects in agriculture and public health programs. Chemically, malathion is a diethyl ester of phosphorodithioic acid and contains:

  • A central phosphorus (P) atom
  • Two ethoxy groups (–OCH2CH3)
  • Two sulfur (S) atoms bonded to phosphorus
It belongs to the broader class of organophosphates that act as cholinesterase inhibitors.

2. What is the chemical formula and molar mass of malathion?

The chemical formula of malathion is C10H19O6PS2 and its molar mass is approximately 330.36 g·mol-1. The molar mass is calculated by summing the atomic masses:

  • C (10 × 12.01) = 120.10 g·mol-1
  • H (19 × 1.008) = 19.15 g·mol-1
  • O (6 × 16.00) = 96.00 g·mol-1
  • P (1 × 30.97) = 30.97 g·mol-1
  • S (2 × 32.06) = 64.12 g·mol-1
Total ≈ 330.36 g·mol-1.

3. How does malathion work as an insecticide?

Malathion works by inhibiting the enzyme acetylcholinesterase, which disrupts nerve signal transmission in insects. Specifically:

  • Malathion is metabolized to malaoxon, a more toxic compound.
  • Malaoxon binds to the active site of acetylcholinesterase.
  • This prevents the breakdown of acetylcholine.
  • Excess acetylcholine causes continuous nerve stimulation, paralysis, and death of the insect.
This mechanism is typical of organophosphate insecticides.

4. What functional groups are present in malathion?

Malathion contains ester groups, a phosphorodithioate group, and sulfur-containing bonds. Its key functional groups include:

  • Two carboxylic ester (–COOR) groups
  • A P=S (thiophosphoryl) bond
  • P–S–C linkages
These functional groups classify malathion as an organophosphate ester and determine its chemical reactivity and biological activity.

5. Is malathion soluble in water?

Malathion is slightly soluble in water but highly soluble in most organic solvents. Its limited water solubility is due to:

  • A relatively large nonpolar hydrocarbon structure
  • Presence of sulfur-containing groups
However, it dissolves well in solvents such as alcohols, acetone, and aromatic hydrocarbons, which is important for pesticide formulation chemistry.

6. What type of chemical reaction breaks down malathion?

Malathion is mainly broken down by hydrolysis of its ester bonds, especially under alkaline conditions. In basic hydrolysis:

  • Water or hydroxide ions attack the ester linkage.
  • The ester bond cleaves to form alcohol and carboxylate products.
This reaction reduces its insecticidal activity and is an important process in environmental degradation.

7. What is the difference between malathion and malaoxon?

The main difference is that malathion contains a P=S bond, while malaoxon contains a more reactive P=O bond. During oxidation:

  • Malathion (P=S) → Malaoxon (P=O)
  • The sulfur atom is replaced by oxygen.
Malaoxon is significantly more toxic because the P=O bond makes it a stronger inhibitor of acetylcholinesterase.

8. What elements are present in malathion?

Malathion contains five elements: carbon (C), hydrogen (H), oxygen (O), phosphorus (P), and sulfur (S). From its formula C10H19O6PS2:

  • Carbon and hydrogen form the organic backbone.
  • Oxygen is present in ester groups.
  • Phosphorus is the central atom of the organophosphate group.
  • Sulfur forms part of the thiophosphate structure.
This composition classifies it as a phosphorus-containing organic compound.

9. Why is malathion considered an organophosphate?

Malathion is considered an organophosphate because it contains a phosphorus atom bonded to organic groups through oxygen and sulfur atoms. Organophosphates generally have:

  • A central phosphorus (P) atom
  • P–O–C or P–S–C linkages
  • Biological activity as cholinesterase inhibitors
Malathion fits this structural definition due to its phosphorodithioate core bonded to carbon-containing groups.

10. What are the main uses of malathion in chemistry and industry?

Malathion is mainly used as an agricultural and public health insecticide. Its key applications include:

  • Control of crop pests on fruits and vegetables
  • Mosquito control programs
  • Treatment for head lice in pharmaceutical formulations
In industrial chemistry, it is formulated into sprays, dusts, and emulsifiable concentrates based on its solubility and stability properties.