Daminozide

"Alar" redirects here. For other uses, see Alar (disambiguation).
Daminozide
Skeletal formula of daminozide
Ball and skill formula of 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
3D model (JSmol)
1863230
ChemSpider
ECHA InfoCard 100.014.988 Edit this at Wikidata
EC Number
  • 216-485-9
KEGG
MeSH daminozide
RTECS number
  • WM9625000
UNII
  • InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11) checkY
    Key: NOQGZXFMHARMLW-UHFFFAOYSA-N checkY
  • CN(C)NC(=O)CCC(O)=O
Properties
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):
  • >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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

  1. ^ EXTOXNET Staff (September 1993). "Pestocide Information Profile: Daminozide". Ithaca, NY: Extension Toxicology Network [EXTOXNET] [CCE. Archived from the original on June 6, 2013. Retrieved 10 September 2013. A Pesticide Information Project of Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. Major support and funding was provided by the USDA/Extension Service/National Agricultural Pesticide Impact Assessment Program.[better source needed]
  2. ^ a b Cite error: The named reference AlarEPA_PFS_840630 was invoked but never defined (see the help page).
  3. ^ "daminozide | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY". www.guidetopharmacology.org. Retrieved 2023-09-24.
  4. ^ a b "Daminozide (Alar) Pesticide Canceled for Food Uses" (Press release). U.S. Environmental Protection Agency. 7 November 1989. Archived from the original on October 3, 2012.
  5. ^ Zeise L, Painter P, Berteau PE, Fan AM, Jackson RJ (1991). "Alar in Fruit: Limited Regulatory Action in the Face of Uncertain Risks". In Garrick BJ, Gekler WC (eds.). The Analysis, Communication, and Perception of Risk. Advances in Risk Analysis. Vol. 9. Boston, MA: Springer. pp. 275–284. doi:10.1007/978-1-4899-2370-7_27. ISBN 978-1-4899-2372-1. Retrieved 10 August 2022.
  6. ^ Office of Prevention, Pesticides and Toxic Substances (September 1993). Daminozide (PDF) (Report). R.E.D.[Reregistration Eligibility Decision] Facts. Washington, DC: U.S. Environmental Protection Agency. EPA-738-F-93-007. Archived from the original (PDF) on 2006-10-06.
  7. ^ Cite error: The named reference EXIM_221108 was invoked but never defined (see the help page).