Dibenzoylhydrazine

Dibenzoylhydrazine

Names
Preferred IUPAC name N′-Benzoylbenzohydrazide
Other names 1,2-Dibenzoylhydrazine
Identifiers
CAS Number	787-84-8
3D model (JSmol)	Interactive image
Beilstein Reference	523810
ChEBI	CHEBI:38453
ChEMBL	ChEMBL115405
ChemSpider	12540
ECHA InfoCard	100.011.209
EC Number	212-329-9
Gmelin Reference	281733
PubChem CID	13085
UNII	N3XBA6QS95 Y
CompTox Dashboard (EPA)	DTXSID7061142
InChI InChI=1S/C14H12N2O2/c17-13(11-7-3-1-4-8-11)15-16-14(18)12-9-5-2-6-10-12/h1-10H,(H,15,17)(H,16,18) Key: GRRIYLZJLGTQJX-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C(=O)NNC(=O)C2=CC=CC=C2
Properties
Chemical formula	C14H12N2O2
Molar mass	240.262 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dibenzoylhydrazine (DBH) is a synthetic chemical compound with the chemical formulation C₁₄H₁₂N₂O₂.

Insecticidal Derivatives

Appropriately substituted dibenzoyl hydrazines show insecticidal activity. This class, usually known as bisacylhydrazines (BAHs), does 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 regulators.

The insecticidal activity of RH-5849 was discovered serendipitously in 1984 at Rohm and Haas, who later commercialised tebufenozide 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, with some applications against coleopteran and dipteran pests. Many plants produce chemicals (phytoecdysteroids) which use this mode of action to kill insects.

BAHs act by agonising the ecdysone receptor. Crystal structures of BAHs bound to the ecdysone receptor were obtained.

BAHs show low mamalian and environmental 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.

Tebufenozide, methoxyfenozide and halofenozide are classed as commercial DBHs.

In 2013, a compound of the substance was tested with promising results against larvae of Anopheles gambiae, the major vector for human malaria.