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Daminozide

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Products Intro: CAS:1596-84-5
Purity:98% HPLC Package:5G;10G;25G;50G;100G;250G;1KG
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Products Intro: Product Name:Daminozide
CAS:1596-84-5
Purity:99.9%
Company Name: Xiamen AmoyChem Co., Ltd
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Products Intro: Product Name:Daminozide 85%
CAS:1596-84-5
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Products Intro: Product Name:Daminozide
CAS:1596-84-5
Purity:0.99 Package:5KG;1KG

Lastest Price from Daminozide manufacturers

  • Daminozide
  • US $2.00 / kg
  • 2019-07-06
  • CAS:1596-84-5
  • Min. Order: 1kg
  • Purity: 99%
  • Supply Ability: Ask
Daminozide Basic information
Overview Applications Mode of action Application methods Risk and Warning References
Product Name:Daminozide
Synonyms:Daminozide - CAS 1596-84-5 - Calbiochem;1-(2,2-Dimethylhydrazide)butanedioic acid;alar85;alar-85;Aminozid;B 995;b995;B-995
CAS:1596-84-5
MF:C6H12N2O3
MW:160.17
EINECS:216-485-9
Product Categories:Miscellaneous;PLANT GROWTH REGULATOR;Plant Hormones;Pesticide intermediates
Mol File:1596-84-5.mol
Daminozide Structure
Daminozide Chemical Properties
Melting point 162-164 °C(lit.)
Boiling point 286.06°C (rough estimate)
density 1.2751 (rough estimate)
refractive index 1.4500 (estimate)
storage temp. 2-8°C
pka5.59±0.10(Predicted)
form White powder
color White crystalline
Water Solubility 100 g/L
Merck 14,2810
BRN 1863230
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, strong acids, wetting agents, oils, copper-containing compounds.
InChIKeyNOQGZXFMHARMLW-UHFFFAOYSA-N
CAS DataBase Reference1596-84-5(CAS DataBase Reference)
NIST Chemistry ReferenceButanedioic acid, mono(2,2-dimethylhydrazide)(1596-84-5)
EPA Substance Registry SystemDaminozide (1596-84-5)
Safety Information
Hazard Codes Xn
Risk Statements 40
Safety Statements 36/37-24/25
RIDADR UN2811 (toxic solid, organic, n.o.s.)
WGK Germany 2
RTECS WM9625000
HS Code 29280000
Hazardous Substances Data1596-84-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Daminozide English
ACROS English
SigmaAldrich English
Daminozide Usage And Synthesis
OverviewDaminozide is one of the first plant growth retardants[PGRs] registered for use on agricultural crops. It was first registered in 1963 for use on potted chrysanthemums in the US and was later approved for use on food crops[1-2]. Although it is still allowed for used on ornamentals plants, its use on food crops was withdrawn in 1990 by the United States environmental protection agency[USEPA] due to its possible health risks such as cancer inducing risks[1-2]. Two major commercial products available in the United States and Canada that contain daminozide: B-Nine[from OHP] and Dazide[from Fine Americas]. Both come as a water-soluble granule containing 85 percent of the active ingredient[3-4]. Based on research conducted by Jim Barrett at the University of Florida, these products are only effective as a foliar spray; if applied as a drench, the chemical is rapidly broken down by the growing media. A typical application spray volume for daminozide is the same as that for other PGRs: 2 quarts per 100 square feet of growing area. B-Nine and Dazide are water-soluble PGRs that permeate leaf surfaces relatively slowly. Movement into leaf tissue only occurs while the leaf surface is still wet with the PGR solution and therefore, the absorption and activity of daminozide increases under slow-drying conditions. Compared with other PGR products, daminozide has a fairly short residual effect, typically lasting one to two weeks but sometimes up to four weeks depending on crop and rate[3-6].
ApplicationsAs a plant growth retardant, daminozide has various applications as dwarfing agent, fruit-setting agent, rooting agent and preservative agent[7]. After treatment, plants can absorb, transport and distribute to various parts of the plant. The initial effect of B9 is to inhibit the synthesis of auxin, inhibit the transport of auxin in plants and the biosynthesis of gibberellin. It can also delay the senescence of leaf lettuce, inhibit the decay and discoloration of mushrooms, and has less effect on green cauliflower and stone cypress. In addition, daminozide preserves chlorophyll in plants and prolongs the life of some perishable vegetables[7].
Mode of actionDaminozide can retard shoot growth in certain plant species, sharing similar effect with the prohexadione, which is an acylcyclohexanedione. This inhibition has been shown to be a result of competition with the natural co‐substrate, 2-oxoglutarate, at the active site of hydroxylases involved in the later stages of the gibberellin[GA] biosynthesis pathway. Detailed analysis found that daminozide inhibits only the bean 3β‐hydroxylase to a significant degree, whereas prohexadione inhibited both the bean and pumpkin enzymes. However, in general, this two plant growth regulator has the same mode of action as prohexadione in distinct plant species, namely to inhibit the 3β-hydroxylase and, to a lesser extent, the 2β-hydroxylase, further resulting in the suppression of the late stages of gibberellin metabolism[8].
The effects of daminozide on plants include:
  1. Delay plant vegetative growth, make the leaves thick green, small and thick, the plant compact and strong, the root system developed, increasing the dry weight of the roots to reduce the proportion of crown roots, which is conducive to control excessive growth and flower bud differentiation[9].
  2. Increase chlorophyll content of crops, delay the senescence of chloroplasts, slow down the growth rate, and have a high photosynthetic net assimilation rate, which is conducive to increasing dry matter accumulation, improving fruit quality, hardness and fruit set rate, and promoting fruit ripening[9].
  3. Increase the sugar content of plant cells, reduce energy consumption, reduce transpiration, which is beneficial to reduce physiological diseases[10].
  4. Promote the biosynthesis of anthocyanins, which is beneficial to improve the color of the fruit and prevent the fruit from decolorizing during storage. Daminozide can be quickly decomposed by microorganisms in the soil[11].
Application methodsDaminozide has a fairly wide range of efficacy on ornamentals and is commonly used on young plants such as seedling plugs and liners. It cannot be legally applied to herbs or other food crops. Typical spray rates for young plants range from 1,500 to 2,500 ppm, whereas higher rates of up to 5,000 ppm are sometimes used on finish plants[12,13]. Carefully follow the mixing instructions on the product labels to deliver the desired concentration. Applications are best made just as plants begin to rapidly elongate. Spray applications are more effective when made at a high humidity, on a cloudy day, at low temperatures and when the air is calm. A spray made during the heat of the day can dry rapidly, resulting in reduced effectiveness[13-15]. Applications should be made to well-watered plants with dry leaves. Wilted plants can absorb less PGR, and wet leaves can dilute the PGR concentration. Overhead irrigation should not be made soon after an application, as the water can wash off the PGR before it has been allowed to enter leaves. Once daminozide enters leaf tissue however, it quickly moves throughout the plant to inhibit subsequent extension growth of stems and leaves[13-15].
Risk and WarningBased on the investigation of the United States environmental protection agency[USEPA], Daminozide has to potential to induce cancer[16,17]. It is also known that it is a selective inhibitor of human KDM2/7 histone demethylases[18].
References
  1. United States Environmental Protection Agency, "Daminozide[Alar] Pesticide Canceled for Food Uses" Archived October 3, 2012, at the Wayback Machine.[press release], 7 November 1989
  2. United States Environmental Protection Agency, Office of Prevention, Pesticides And Toxic Substances[September 1993]. "R.E.D. Facts: Daminozide"
  3. https://www.extension.purdue.edu/extmedia/ho/ho-248-w.pdf
  4. https://www.purdue.edu/hla/sites/cea/wp-content/uploads/sites/15/2008/10/Comparing-PGR-Final.pdf
  5. https://www.ballpublishing.com/pdf/PGR_GUIDE_2013-LowRez.pdf
  6. https://www.maximumyield.com/definition/3304/daminozide
  7. http://www.lmdchinapgr.com/news/116.html
  8. https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1399-3054.1997.tb01001.x
  9. https://www.degruyter.com/downloadpdf/j/fhort.2017.29.issue-1/fhort-2017-0004/fhort-2017-0004.xml
  10. https://www.ncbi.nlm.nih.gov/pubmed/25342260
  11. https://link.springer.com/article/10.1007/s00344-012-9315-3
  12. https://www.panamseed.com/utility/CultureSheetPDF.aspx?pagename=culture.aspx&txtPHID=046706198039762&type=Ann
  13. https://www.syngentaflowers-us.com/file/4336/download?token=UMCcNgWb
  14. https://www.ballpublishing.com/pdf/PGR_GUIDE_2013-LowRez.pdf
  15. http://journal.ashspublications.org/content/125/2/195.full.pdf
  16. https://www.ncbi.nlm.nih.gov/pubmed/22724510
  17. https://phytotechlab.com/mwdownloads/download/link/id/2216/
  18. 18. Rose, Nathan R., et al. "Plant Growth Regulator Daminozide Is a Selective Inhibitor of Human KDM2/7 Histone Demethylases." Journal of Medicinal Chemistry 55.14(2012]:6639-6643.
Chemical PropertiesDaminozide is a colorless crystalline solid.
Chemical Propertieswhite crystalline powder
UsesPlant cell culture, tested.
UsesPlant growth regulator.
General DescriptionOdorless white crystals or powder.
Air & Water ReactionsSlightly soluble in water.
Reactivity ProfileDaminozide 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 HazardFlash point data for Daminozide are not available; however, Daminozide is probably combustible.
Agricultural UsesPlant 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 nameALAR®; ALAR-85®; AMINOZID®; AMINOZIDE®; B-9®; B-995®; B-NINE®; DAZIDE®; DAZIDE®; ENHANCE®; DIMAS®; KYLAR®; SADH®
Safety ProfileSuspected 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 ExposureDaminozide 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.
Metabolic pathwayDaminozide 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.
ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
IncompatibilitiesDaminozide 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).
Daminozide Preparation Products And Raw materials
Raw materialsSuccinic anhydride-->Succinic acid-->1,1-Dimethylhydrazine
Tag:Daminozide(1596-84-5) Related Product Information
Diphenolic acid Succinic acid Succinic anhydride Formylhydrazine 4-(Diethylamino)salicylaldehyde 1,1-Dimethylhydrazine 1,5-Diphenylcarbazide Adipic dihydrazide 5-Chlorovaleric acid POLY(N-ISOPROPYL ACRYLAMIDE) 4-Dimethylaminobenzaldehyde Ascoric Acid Folic acid Carbohydrazide Tebufenozide N-Methylolacrylamide Butanedihydrazide Dimethylsulfamoyl chloride