Daminozide

Description

Alar is a systemic growth regulator approved in the United States for use on ornamental plants such as chrysanthemums, poinsettias, and bedding plants located in enclosed structures such as greenhouses. Alar reduces internode elongation; induces heat, drought, and frost resistance; and produces darker foliage and stronger stems as well as earlier and multiple flowers and fruits. A spray is often applied at the rate of 1500–10 000 ppm.

Chemical properties

Daminozide is a colorless crystalline solid.

Chemical properties

white crystalline powder

The Uses of Daminozide

Plant cell culture, tested.

The Uses of Daminozide

Plant growth regulator.

The Uses of Daminozide

Alar is a systemic agent (i.e., taken up by the fruit) and cannot be removed by washing or peeling.

The Uses of Daminozide

Daminozide is a plant growth regulator used to improve crop quality and maximize yield.Used as a standard for Pesticide detection. Useful in cannabis testing kits as a component of pesticide mixes (P698240).

Definition

ChEBI: Daminozide is a straight-chain fatty acid.

What are the applications of Application

Daminozide is a KDM (LSD1) histone demethylase inhibitor

General Description

Odorless white crystals or powder.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Daminozide may be heat sensitive. Incompatible with strong oxidizing agents, strong acids, and bases. Also incompatible with wetting agents, alkaline materials, oils and copper-containing compounds. May corrode metals . May generate toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. May generate flammable gases with alkali metals. Explosive reactions can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Fire Hazard

Flash point data for Daminozide are not available; however, Daminozide is probably combustible.

Agricultural Uses

Plant growth regulator: Daminozide is a systemic growth regulator registered for use on ornamentals, including potted chrysanthemums and poinsettias, and bedding plants in enclosed structures. U.S. sales for food and feed crops were halted in 1989 because of health considerations, i. e., the Alar scare on apples.

Trade name

ALAR®; ALAR-85®; AMINOZID®; AMINOZIDE®; B-9®; B-995®; B-NINE®; DAZIDE®; DAZIDE®; ENHANCE®; DIMAS®; KYLAR®; SADH®

Safety Profile

Suspected carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx

Potential Exposure

Daminozide is a herbicide/plant growth regulator used on certain fruit (especially apples) to improve the balance between growth and fruit production and to improve fruit quality and synchronize maturity. A RUP. United States sales were suspended in 1989 due to health considerations.

First aid

Skin Contact: Flood all areas of body that havecontacted the substance with water. Do not wait to removecontaminated clothing; do it under the water stream. Use soapto help assure removal. Isolate contaminated clothing whenremoved to prevent contact by others. Eye Contact: Removeany contact lenses at once. Flush eyes well with copious quantities of water or normal saline for at least 2030 min. Seekmedical attention. Inhalation: Leave contaminated area immediately; breathe fresh air. Proper respiratory protection must besupplied to any rescuers. If coughing, difficult breathing, orany other symptoms develop, seek medical attention at once,even if symptoms develop many hours after exposure.Ingestion: If convulsions are not present, give a glass or two ofwater or milk to dilute the substance. Assure that the person’sairway is unobstructed and contact a hospital or poison centerimmediately for advice on whether or not to induce vomiting.

Metabolic pathway

Daminozide is oxidized by photochemically generated singlet oxygen, with rose bengal as a sensitizing agent in methanol-d4 to yield equimolar amounts of N,N- dimethylnitrosamine (DMN) and succinic anhydride as the only products detected by 1H and 13C NMR. The reaction is efficiently inhibited by 2,5-dimethylfuran as a competitor for, or sodium azide as a quencher of, singlet oxygen. Humic acid, similar to that found in natural and waste waters, and a red pigment isolated from apple peel also sensitize the photodegradation of daminozide to produce DMN and succinic anhydride.

storage

Room temperature

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Toxicity evaluation

Alar does not degrade following contact with water but degrades rapidly in soil resulting in volatile compounds (including formaldehyde) and bound residues; therefore mobility is not considered a concern. In greenhouse studies, alar persistence ranged from 3 to 4 days in different soils. Since alar is registered for greenhouse use only, agricultural runoff into groundwater is not expected to be a concern.

Incompatibilities

Daminozide may be heat sensitive. Incompatible with strong oxidizing agents, strong acids, and bases. Also incompatible with wetting agents, alkaline materials, oils and copper-containing compounds. May corrode metals (NTP, 1992). May generate toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and reducing agents. May generate flammable gases with alkali metals. Explosive reactions can occur with strong oxidizing agents, metal salts, peroxides, and sulfides . Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithio- nites (releasing hydrogen sulfate and oxides of sulfur).

References

1) Rose et al. (2012), Plant growth regulator daminozide is a selective inhibitor of human KDM2/7 histone methylases; J. Med. Chem., 55 6639 2) Chen et al. (2016),?Lysine demethylase 2A promotes stemness and angiogenesis of breast cancer by upregulating Jagged1; Oncotarget, 7 27689