123-33-1 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 123-33-1 differently. You can refer to the following data:
1. Maleic hydrazide is a colorless crystalline
solid. Odorless.
2. Maleic hydrazide is a crystalline solid
Uses
Different sources of media describe the Uses of 123-33-1 differently. You can refer to the following data:
1. Growth 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.
2. Maleic Hydrazide is used in plant growth regulator formulations.
3. Experimentally in horticulture and agriculture. To control suckering of tobacco. In the synthesis of pyridazine.
Production Methods
Maleic 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 Description
Odorless white solid. Sinks in water.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
3,6-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.
Hazard
Toxic by ingestion. Questionable carcinogen.
Health Hazard
Inhalation 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 Hazard
Special Hazards of Combustion Products: Toxic nitrogen oxides are produced.
Agricultural Uses
Herbicide, 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 name
BH 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 Profile
Moderately 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 Exposure
Maleic 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
Carcinogenicity
Mice 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 Fate
Soil. 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).
Shipping
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous
hazardous material, Technical Name Required
Purification Methods
Crystallise the hydrazide from water. Dry it at ~100o over P2O5. [Beilstein 24 III/IV 1186.]
Incompatibilities
Dust 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 Disposal
Consult 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.
Check Digit Verification of cas no
The CAS Registry Mumber 123-33-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 123-33:
(5*1)+(4*2)+(3*3)+(2*3)+(1*3)=31
31 % 10 = 1
So 123-33-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H2N2O2/c7-3-1-2-4(8)6-5-3/h1-2H
123-33-1Relevant articles and documents
Triethanolamine as an inexpensive and efficient catalyst for the green synthesis of novel 1H-pyrazolo[1,2-a]pyridazine-5,8-diones under ultrasound irradiation in water and their antibacterial activity
Khoraamabadi-Zad, Ahmad,Azadmanesh, Mohammad,Karamian, Roya,Asadbegy, Mostafa,Akbari, Maryam
, p. 47721 - 47725 (2014)
Triethanolamine was found to be an efficient catalyst for the synthesis of new 1H-pyrazolo[1,2-a]pyridazine-5,8-diones by a one-pot reaction of maleic hydrazide, with aromatic aldehydes and malononitrile in H2O under ultrasonic irradiation. The advantages of this method are the use of an inexpensive and readily available catalyst, easy workup, improved yields, and the use of H2O as a green solvent. To assess their antibacterial activity, all the synthesized compounds were dissolved in DMSO and subjected to biological evaluation using the disc diffusion method against 3 Gram positive and 3 Gram negative bacteria. This journal is
UV-induced photoisomerization of maleic hydrazide
Reva, Igor,Almeida, Bruno J. A. N.,Fausto, Rui,Lapinski, Leszek
, p. 74 - 83,10 (2012)
Monomers of maleic hydrazide (3-hydroxypyridazin-6-one) were studied using the experimental matrix-isolation technique as well as DFT and QCISD methods of quantum chemistry. The oxo-hydroxy tautomer was theoretically predicted to be the most stable form o
-
Ohashi et al.
, p. 970,972 (1964)
-
Dramatically enhanced fluorescence of heteroaromatic chromophores upon insertion as spacers into oligo(triacetylene)s
Edelmann, Michael J.,Raimundo, Jean-Manuel,Utesch, Nils F.,Diederich, Francois,Boudon, Corinne,Gisselbrecht, Jean-Paul,Gross, Maurice
, p. 2195 - 2213 (2002)
In continuation of a previous study on the modulation of π-electron conjugation of oligo(triacetylene)s by insertion of central hetero-spacer fragments between two (E)-hex-3-ene-1,5-diyne ((E)-1,2-diethynylethene, DEE) moieties (Fig. 1), a new series of trimeric hybrid oligomers (14-18 and 22-24, Fig. 2) were prepared (Schemes 1-3). Spacers used were both electron-deficient (quinoxaline-based heterocycles, pyridazine) and electron-rich (2,2′-bithiophene, 9,9-dioctyl-9H-fluorene) chromophores. With 19-21 (Scheme 4), a series of transition metal complexes was synthesized as potential precursors for nanoscale scaffolding based on both covalent acetylenic coupling and supramolecular assembly. The UV/VIS spectra (Fig. 3) revealed that the majority of spacers provided heterotrimers featuring extended π-electron delocalization. The new hybrid chromophores show a dramatically enhanced fluorescence compared with the DEE dimer 13 and homo-trimer 12 (Fig. 5). This increase in emission intensity appears as a general feature of these systems: even if the spacer molecule is non-fluorescent, the corresponding hetero-trimer may show a strong emission (Table 2). The redox properties of the new hybrid chromophores were determined by cyclic voltammetry (CV) and rotating-disk voltammetry (RDV) (Table 3 and Fig. 5). In each case, the first one-electron reduction step in the hetero-trimers appeared anodically shifted compared with DEE dimer 13 and homo-trimer 12. With larger spacer chromophore extending into two dimensions (as in 14-18, Fig. 2), the anodic shift (by 240-490 mV, Table 3) seems to originate from inductive effects of the two strongly electron-accepting DEE substituents rather than from extended π-electron conjugation along the oligomeric backbone, as had previously been observed for DEE-substituted porphyrins.
Synthesis and anticonvulsant activity of novel 1-substituted-1,2-dihydro-pyridazine-3,6-diones.
Sivakumar, Ramaiah,Anbalagan, Navaneetharaman,Gunasekaran, Vedachalam,Leonard, Joseph Thomas
, p. 1407 - 1411 (2003)
The synthesis and pharmacological evaluation of novel 1-substituted-1,2-dihydro-pyridazine-3,6-diones (4a--l, 5a--j) as potential anticonvulsant agents are described. The compounds were tested in vivo for the anticonvulsant activity. The compound which have maximum protection against MES induced seizures is 1-[3-(2-aminophenylamino)-2-hydroxypropyl)-1,2-dihydro-pyridazine-3,6-dione 4h (ED(50)=44.7 mg x kg(-1) i.p.) 1-[2-hydroxy-3-piperazin1-yl-propyl)-1,2-dihydro-pyridazine-3,6-dione 4c (ED(50)=72 mg x kg(-1) i.p.) and 1-[2-hydroxy-3-imidazol-1-yl-propyl)-1,2-dihydro-pyridazine-3,6-dione 4d (ED(50)=79 mg x kg(-1) i.p.) were also found to have maximum protection against MES induced seizures. Whereas all these compounds failed to protect the animals from subcutaneous pentylenetetrazole (Metrozol) seizure threshold test (sc-Met).
Liquid Phase Synthesis of 1,2-Dihydropyridazine-3,6-dione in the Presence of Ionite Catalysts
Baeshov, A. B.,Dzhumadullaeva, S. A.
, p. 954 - 957 (2021/06/07)
Abstract: The catalytic activity of synthetic ion-exchange resins was studied in the reaction between cis-butenedioic acid and hydrazine (aqueous medium; temperature, 95°C; 2–4 h) with the formation of heterocyclic hydrazide–1,2-dihydropyridazine-3,6-dione. It is established that the most effective catalysts are KU?2-8 and KRF-10P cation exchangers. A probable mechanism of the process with the formation of adsorption complexes and the participation of fixed polymer-bound sulfonate ions and counterions of the cation exchanger is proposed on the basis of IR spectroscopic studies.
COMPOSITIONS OF DICARBOXYLIC ACID DERIVATIVES
-
Page/Page column 12; 13, (2021/01/22)
The present invention relates to agricultural compositions containing dicarboxylic acid hydrazides and transition metal ions, and the preparation thereof. The compositions are useful in the treatments of plants or seeds as an anti-sprout agent, growth regulator and/or pest control agent. In particular, it relates to maleic hydrazide combined with copper, nickel, manganese, iron or zinc. The transition metal ions improve the storage stability of the dicarboxylic acid hydrazide and prevent generation of free hydrazine.
Natural product-based pesticide discovery: Design, synthesis and bioactivity studies of N-amino-maleimide derivatives
Song, Xiangmin,Liu, Chunjuan,Chen, Peiqi,Zhang, Hao,Sun, Ranfeng
, (2018/07/10)
Natural products are an important source of pesticide discovery. A series of N-amino-maleimide derivatives containing hydrazone group were designed and synthesized based on the structure of linderone and methyllinderone which were isolated from Lindera erythrocarpa Makino. According to the bioassay results, compounds 2 and 3 showed 60% inhibition against mosquito (Culex pipiens pallens) at 0.25 μg·mL?1. Furthermore, the results of antifungal tests indicated that most compounds exhibited much better antifungal activities against fourteen phytopathogenic fungi than linderone and methyllinderone and some compounds exhibited better antifungal activities than commercial fungicides (carbendazim and chlorothalonil) at 50 μg·mL?1. In particular, compound 12 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 11 phytopathogenic fungi) and compounds 12 and 14 displayed 60.6% and 47.9% inhibitory activity against Rhizoctonia cerealis at 12.5 μg·mL?1 respectively. Furthermore, compound 17 was synthesized, which lacks N-substituent at maleimide and its poor antifungal activity against Sclerotinia sclerotiorum and Rhizoctonia cerealis at 50 μg·mL?1 showed that the backbone structure of N-amino-maleimide derivatives containing hydrazone group was important to the antifungal activity.
