Daminozide

Title: Daminozide
CAS Registry Number: 1596-84-5
CAS Name: Butanedioic acid mono(2,2-dimethylhydrazide)
Additional Names: N-(dimethylamino)succinamic acid; succinic acid 2,2-dimethylhydrazide
Manufacturers' Codes: B-9; B-995
Trademarks: Alar (Uniroyal); B-Nine (Uniroyal); Kylar (Uniroyal)
Molecular Formula: C6H12N2O3
Molecular Weight: 160.17
Percent Composition: C 44.99%, H 7.55%, N 17.49%, O 29.97%
Line Formula: HOOCCH2CH2CONHN(CH3)2
Literature References: Prepn: BE 613799, C.A. 57, 10281d (1962); H. A. Hageman, W. L. Hubbard, US 3257414 (1962, 1966 both to U.S. Rubber). Effect in controlling growth in apples: F. W. Southwick et al., Proc. Am. Soc. Hortic. Sci. 92, 71 (1968); D. W. Greene et al., Fruit Var. J. 40, 41 (1986). In vitro and in vivo mechanism of action studies: K. Ryugo, R. M. Sachs, J. Am. Soc. Hortic. Sci. 94, 529 (1969). Hydrolysis to 1,1-dimethylhydrazine, q.v., and determn in food products: W. H. Newsome, J. Agric. Food Chem. 28, 319 (1980); M. K. Conditt, J. R. Baumgardner, J. Assoc. Off. Anal. Chem. 71, 735 (1988). Discussion of toxicological evaluation: D. Campt, EPA Journal 13, 32 (1987).
Properties: Crystals, mp 154-155°. Soly 10% in water, 2.5% in acetone, 5% in methanol.
Melting point: mp 154-155°
Use: Plant growth regulator.
d-Amyl Bromide Danaparoid Danazol Danofloxacin Dansyl Chloride

Daminozide
Skeletal formula of daminozide
Identifiers
CAS number 1596-84-5 YesY
PubChem 15331
ChemSpider 14593 YesY
UNII F6KF33M5UB YesY
EC number 216-485-9
KEGG C10996 YesY
MeSH daminozide
RTECS number WM9625000
Beilstein Reference 1863230
Jmol-3D images Image 1
Properties
Molecular formula C6H12N2O3
Molar mass 160.17 g mol−1
Appearance White crystals
Melting point 159.24 °C; 318.63 °F; 432.39 K
Hazards
LD50
  • >1,600 mg kg−1 (dermal, rabbit)
  • 8,400 mg kg−1 (oral, rat)
[1]
Related compounds
Related alkanoic acids Octopine
Related compounds
  • 1,2-Dimethylhydrazine
  • Biurea
  • Bis-tris propane
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Daminozide — also known as Alar, Kylar, B-NINE, DMASA, SADH, or B 995 — is a plant growth regulator, a chemical sprayed on fruit to regulate their growth, make their harvest easier, and keep apples from falling off the trees before they are ripe. This makes sure they are red and firm for storage. Alar was first approved for use in the U.S. in 1963, it was primarily used on apples until 1989 when it was voluntarily withdrawn by the manufacturer after the U.S. Environmental Protection Agency proposed banning it based on unacceptably high cancer risks to consumers.[2]

It has been produced in the U.S. by the Uniroyal Chemical Company, Inc, (now integrated into the Chemtura Corporation) which registered daminozide for use on fruits intended for human consumption in 1963. In addition to apples and ornamentals, it was also registered for use on cherries, peaches, pears, Concord grapes, tomato transplants and peanut vines. 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.[2] In 1989, it became illegal to use daminozide on food crops in the US, but it is still allowed for use on non-food crops like ornamentals.[3]