Phenylpyrazole insecticides are a class of chemically-related broad-spectrum

insecticides Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...

. The chemical structures of these insecticides are characterized by a central

pyrazole Pyrazole is an organic compound with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent ...

ring with a

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

group attached to one of the nitrogen atoms of the pyrazole.

History

Phenylpyrazole insecticides were developed in response to increasing

pesticide resistance Pesticide resistance describes the decreased susceptibility of a pest population to a pesticide that was previously effective at controlling the pest. Pest species evolve pesticide resistance via natural selection: the most resistant specimens su ...

to other chemicals. Now, along with

neonicotinoid Neonicotinoids (sometimes shortened to neonics ) are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s. The neonicotinoid family includes acetamiprid, clothianidin, dinote ...

s, they are some of the most widely-used pesticides.

Mode of Action

Phenylpyrazole insecticides function by blocking glutamate-activated

chloride channel Chloride channels are a superfamily of poorly understood ion channels specific for chloride. These channels may conduct many different ions, but are named for chloride because its concentration ''in vivo'' is much higher than other anions. Severa ...

s in insects. Mammals do not have this type of chloride channel, making them much less susceptible to its effects. However, they do have the capacity to disrupt

epithelial cells Epithelium or epithelial tissue is one of the four basic types of animal tissue, along with connective tissue, muscle tissue and nervous tissue. It is a thin, continuous, protective layer of compactly packed cells with a little intercellula ...

in the human intestine and adversely impact human health.

Examples

Examples include: * acetoprole * ethiprole *

fipronil Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl ...

* flufiprole * pyraclofos * pyrafluprole * pyriprole * pyrolan * vaniliprole

References

External links

* {{commons category inline, Phenylpyrazole insecticides, lcfirst=yes Pyrazoles Insecticides Synthetic insecticides