Daminozide
Chemical compound / From Wikipedia, the free encyclopedia
Daminozide, also known as aminozide, Alar, Kylar, SADH, B-995, B-nine,[2] and DMASA,[3] is 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. In addition to apples and ornamental plants, they also registered it for use on cherries, peaches, pears, Concord grapes, tomato transplants, and peanut vines. Alar was first approved for use in the U.S. 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]
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Names | |
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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) |
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1863230 | |
ChemSpider |
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ECHA InfoCard | 100.014.988 |
EC Number |
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KEGG |
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MeSH | daminozide |
PubChem CID |
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RTECS number |
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UNII | |
CompTox Dashboard (EPA) |
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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): | |
LD50 (median dose) |
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Related compounds | |
Related alkanoic acids |
Octopine |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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On fruit trees, daminozide affects flow-bud initiation, fruit-set maturity, fruit firmness and coloring, preharvest drop and market quality of fruit at harvest and during storage.[4] When consumed by mammals, daminozide is catabolised into two chemical components, succinic acid (a non-toxic general intermediate in primary metabolism[citation needed]), and 1, 1-dimethylhydrazine (a component with a history of studies associating it with carcinogenic activity in animal models relevant to humans). The scission also occurs when the sprayed chemical residue remains on stored fruit, increasingly with higher temperatures and longer times.[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]