Daminozide

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Daminozide

Names
Preferred IUPAC name 4-(2,2-Dimethylhydrazin-1-yl)-4-oxobutanoic acid
Other names N-(Dimethylamino)succinamic acid; Butanedioic acid mono (2,2-dimethyl hydrazine); Succinic acid 2,2-dimethyl hydrazide
Identifiers
CAS Number	1596-84-5 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1863230
ChemSpider	14593 Y
ECHA InfoCard	100.014.988
EC Number	216-485-9
KEGG	C10996 Y
MeSH	daminozide
PubChem CID	15331
RTECS number	WM9625000
UNII	F6KF33M5UB Y
CompTox Dashboard (EPA)	DTXSID9020370
InChI InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11) Y Key: NOQGZXFMHARMLW-UHFFFAOYSA-N Y
SMILES CN(C)NC(=O)CCC(O)=O
Properties
Chemical formula	C6H12N2O3
Molar mass	160.173 g·mol−1
Appearance	White crystals
Melting point	159.24 °C; 318.63 °F; 432.39 K
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	>1,600 mg kg−1 (dermal, rabbit) 8,400 mg kg−1 (oral, rat) [1][needs update]
Related compounds
Related alkanoic acids	Octopine
Related compounds	1,2-Dimethylhydrazine Biurea Bis-tris propane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Daminozide, also known as aminozide, Alar, Kylar, SADH, B-995, B-nine,^[2] and DMASA,^[3] is an organic compound which acts as a plant growth regulator.^[2] It was produced in the U.S. by the Uniroyal Chemical Company, Inc., (now integrated into the Chemtura Corporation^{[not verified in body]}), which registered daminozide for use on fruits intended for human consumption in 1963. It was primarily used on apples until 1989, when the manufacturer voluntarily withdrew it after the U.S. Environmental Protection Agency proposed banning it based on concerns about cancer risks to consumers.^[4] In addition to apples and ornamental plants, Uniroyal also registered daminozide for use on cherries, peaches, pears, Concord grapes, tomato transplants, and peanut vines.

When used on fruit trees, daminozide affects flower bud initiation, fruit maturity, fruit firmness and coloring, preharvest drop and market quality of fruit at time of harvest and during storage.^[4] When consumed by mammals, daminozide is catabolised into succinic acid (a non-toxic general intermediate in primary metabolism^{[citation needed]}) and 1,1-dimethylhydrazine (a compound with a history of studies associating it with carcinogenic activity in animal models relevant to humans). Breakdown into these two compounds also occurs when the sprayed chemical residue remains on stored fruit, especially with higher temperatures and over longer time periods.^[5]

In 1989, the EPA outlawed daminozide on U.S. food crops, but still allowed it for non-food crops like ornamental plants.^[6] As of August 2022, daminozide appeared as severely restricted in its exports on the list of pesticides whose shipments were ineligible for export credit insurance under the Export–Import Bank of the United States.^[7]