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Maleic hydrazide

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Maleic hydrazide Basic information
Maleic hydrazide Chemical Properties
  • Melting point:299-301 °C (dec.)(lit.)
  • Boiling point:209.98°C (rough estimate)
  • Density 1,6 g/cm3
  • refractive index 1.4610 (estimate)
  • Flash point:300°C
  • storage temp.  0-6°C
  • solubility 4510mg/l
  • form neat
  • pka9.01±0.20(Predicted)
  • color White crystalline
  • OdorOdorless
  • Water Solubility 6 g/L
  • Merck 14,5705
  • BRN 112223
  • InChIKeyBGRDGMRNKXEXQD-UHFFFAOYSA-N
  • CAS DataBase Reference123-33-1(CAS DataBase Reference)
  • IARC3 (Vol. 4, Sup 7) 1987
  • NIST Chemistry ReferenceMaleic hydrazide(123-33-1)
  • EPA Substance Registry SystemMaleic hydrazide (123-33-1)
Safety Information
MSDS
Maleic hydrazide Usage And Synthesis
  • Chemical PropertiesMaleic hydrazide is a colorless crystalline solid. Odorless.
  • Chemical PropertiesMaleic hydrazide is a crystalline solid
  • UsesGrowth regulator used to control the sprouting of potatoes and onions and to prevent sucker development on tobacco, fruits, ornamentals, vines, field crops and in forestry. Also used to control insects in warehouses, storerooms, empty sacks and in animal and poultry houses.
  • UsesMaleic Hydrazide is used in plant growth regulator formulations.
  • UsesExperimentally in horticulture and agriculture. To control suckering of tobacco. In the synthesis of pyridazine.
  • Production MethodsMaleic hydrazide is slightly acidic. It is made by treating maleic anhydride with hydrazine hydrate in alcohol.
  • Synthesis Reference(s)Journal of the American Chemical Society, 73, p. 1873, 1951 DOI: 10.1021/ja01148a537
  • General DescriptionOdorless white solid. Sinks in water.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity Profile3,6-Dihydroxypyridazine can be decomposed by oxidizing agents. 3,6-Dihydroxypyridazine can also be decomposed by strong acids. 3,6-Dihydroxypyridazine forms water-soluble alkali-metal and amine salts. 3,6-Dihydroxypyridazine is slightly acidic and may be titrated as a monobasic acid. Mild oxidation produces a compound which reacts instantly with dienes at -107° F to form crystalline derivatives. 3,6-Dihydroxypyridazine is slightly corrosive to iron and zinc. 3,6-Dihydroxypyridazine is incompatible with pesticides that are highly alkaline in reaction. In the presence of heavy metal and iron, zinc, calcium and magnesium ions, sparingly-soluble salts are formed.
  • HazardToxic by ingestion. Questionable carcinogen.
  • Health HazardInhalation of dust causes irritation of nose and throat. Contact with eyes or skin causes irritation. Ingestion has been observed to cause tremors and muscle spasms in test animals.
  • Fire HazardSpecial Hazards of Combustion Products: Toxic nitrogen oxides are produced.
  • Agricultural UsesHerbicide, Plant growth regulator, Fungicide: Banned for use in EU countries. Actively registered for use in the U.S. Maleic hydrazide is a plant growth regulator (sprout inhibitor) and herbicide that is registered for use on tobacco, potatoes, onions, non-bearing citrus, turf, utility and highway rights-of-way, airports, industrial land, lawns, recreational areas, ornamental/shade trees and ornamental plants. Most of the use of maleic hydrazide in the U.S. is on tobacco.
  • Trade nameBH DOCK KILLER®; BOS MH®; BURTOLIN®; CHEMFORM®; DE-CUT®; DESPROUT D REXEL-SUPER P®; EC 300®; FAIR 30®; FAIR PLUS®; FAIR PS®; MAINTAIN 3®; MALEIN 30®; MALAZIDE®; MH 30®; MH 40®; MH 36 BAYER®; PO-SAN® (with 9H-Fluorene-9-carboxylic acid, 2-chloro-9-hydroxy-, methyl ester)®; REGULOX®; REGULOX W®; REGULOX 50 W®; RETARD®; ROYAL MH 30®; ROYAL SLO-GRO®; SLO-GRO®; SPROUT-STOP®; STUNTMAN®; SUCKER-STUFF®; SUPER DE-SPROUT®; SUPER SPROUT STOP®; VONDALDHYDE®; VONDRAX®
  • Safety ProfileModerately toxic by ingestion. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Can cause chronic liver damage and acute central nervous system effects. When heated to decomposition it emits hghly toxic fumes of NOx See also HYDRAZINE.
  • Potential ExposureMaleic hydrazide is a pyridazine/ pyridazinone herbicide, plant growth regulator, and fungicide that is registered for use on tobacco, potatoes, onions, nonbearing citrus, turf, utility and highway rights-of-way, airports, industrial land, lawns, recreational areas, ornamental/ shade trees and ornamental plants. Most of the use of maleic hydrazide in the United States is on tobacco. Banned for use in EU countries. Actively registered for use in the United States
  • CarcinogenicityMice fed up to 3 mg/kg for 320 ‘days showed no carcinogenic effect when sacrificed at 2 years of age. Mice fed 0, 1000, 3200, and 10,000 ppm in the diet in 23 months showed no oncogenic effect. Rats were fed diets providing doses of 0, 25, 500, or 1000 mg/kg. Occasional increases in tumor incidences were seen, but as these were not consistent between the two sexes and did not achieve statistical significance, they are considered not attributable to maleic hydrazide.
    Application of maleic hydrazide to the skin three times a week up to a cumulative dose of 300mg was not carcinogenic . Oral treatment of dogs and rats for 17–28 months resulted in no excess cancer in any tissue or organs. Subcutaneous injections of maleic hydrazide in newborn mice produced a very slight increase in liver tumors, although this finding is generally considered negative. A study in which maleic hydrazide was given subcutaneously to mice (55 mg total over 49 weeks) showed no evidence of a carcinogenic response was seen.
  • Environmental FateSoil. The half-life in soil was reported to be 2–8 weeks (Hartley and Kidd, 1987). When maleic hydrazide was applied to muck, sand and clay at concentrations of 0.7 and 2.7, 1.0 and 3.75 and 0.85 and 3.4 ppm, 86 and 100, 87 and 100 and 47 and 67% degradation yields were obtained, respectively (Hoffman et al., 1962).
    Plant. Major plant metabolites include fumaric, succinic and maleic acids (Hartley and Kidd, 1987).
    Photolytic. In water, maleic hydrazide showed an absorption maximum at 300 nm indicating direct photolysis should occur (Gore et al., 1971).
    Chemical/Physical. Reacts with alkalies and amines forming water-soluble salts (Hartley and Kidd, 1987). Decomposed by oxidizing acids releasing nitrogen (Worthing and Hance, 1991). Decomposes at 260°C (Windholz et al., 1983) releasing toxic fumes of nitrogen oxides (Sax and Lewis, 1987).
  • ShippingUN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
  • Purification MethodsCrystallise the hydrazide from water. Dry it at ~100o over P2O5. [Beilstein 24 III/IV 1186.]
  • IncompatibilitiesDust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Slightly corrosive to iron and zinc. Maleic hydrazide forms water-soluble alkali-metal and amine salts. It is slightly acidic and may be titrated as a monobasic acid. Mild oxidation produces a compound which reacts instantly with dienes at 277C/ 2 107F to form crystalline derivatives. It is incompatible with pesticides that are highly alkaline in reaction. This chemical is slightly corrosive to iron and zinc. In the presence of heavy metal and iron, zinc, calcium, and magnesium ions, sparingly soluble salts are formed.
  • Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Maleic hydrazide Preparation Products And Raw materials
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