The diacylhydrazines, also known as bisacylhydrazines (BAHs) or dibenzoylhydrazines are appropriately substituted derivatives of dibenzoyl hydrazine. They do not immediately kill the insect, but produces premature unsuccessful moulting, which then causes the death of the insect. BAHs thus belong to the class of

insect growth regulator An insect growth regulator (IGR) is a chemical insecticide that kills insects indirectly by disrupting their life cycles. The term was initially proposed to describe the effects of juvenile hormone analogs. Although the term "insect growth disrupto ...

s. The insecticidal activity of RH-5849 was discovered serendipitously in 1984 at Rohm and Haas, who later commercialised

tebufenozide Tebufenozide is an insecticide that acts as a molting hormone. It is an agonist of the ecdysone receptor that causes premature molting in larvae. It is primarily used against caterpillar pests. It belongs to the class of diacylhydrazines. Bec ...

methoxyfenozide, and halofenozide. Later other companies commercialised chromafenozide and fufenozide. The EPA removed halofenozide from the market in 2012 on the request of the manufacturer. BAHs were estimated to account for ca 1% of the 18.4-billion-dollar 2018 global pesticide market. BAHs are used against

lepidoptera Lepidoptera ( ) or lepidopterans is an order (biology), order of winged insects which includes butterflies and moths. About 180,000 species of the Lepidoptera have been described, representing 10% of the total described species of living organ ...

, with some applications against

coleopteran Beetles are insects that form the order Coleoptera (), in the superorder Holometabola. Their front pair of wings are hardened into wing-cases, elytra, distinguishing them from most other insects. The Coleoptera, with about 400,000 described ...

and

dipteran Flies are insects of the order Diptera, the name being derived from the Greek δι- ''di-'' "two", and πτερόν ''pteron'' "wing". Insects of this order use only a single pair of wings to fly, the hindwings having evolved into advanced ...

pests. Many plants produce chemicals ( phytoecdysteroids) which use this

mode of action In pharmacology and biochemistry, mode of action (MoA) describes a functional or anatomical change, resulting from the exposure of a living organism to a substance. In comparison, a mechanism of action (MOA) describes such changes at the molecul ...

to kill insects. BAHs act by agonising the

ecdysone receptor The ecdysone receptor is a nuclear receptor found in arthropods, where it controls development and contributes to other processes such as reproduction. The receptor is a non-covalent heterodimer of two proteins, the EcR protein and ultraspiracle ...

. Crystal structures of BAHs bound to the ecdysone receptor were obtained. BAHs show low

mammalian A mammal () is a vertebrate animal of the Class (biology), class Mammalia (). Mammals are characterised by the presence of milk-producing mammary glands for feeding their young, a broad neocortex region of the brain, fur or hair, and three ...

and

environmental Environment most often refers to: __NOTOC__ * Natural environment, referring respectively to all living and non-living things occurring naturally and the physical and biological factors along with their chemical interactions that affect an organism ...

toxicity. Methoxyfenozide was given a presidential green chemistry award in 1998. Both tebufenozide and methoxyfenozide were registered by the EPA under its Reduced Risk Pesticide Program.

References

{{reflist Insecticides Hydrazides