Maleic hydrazide

Iupac Name：1,2-dihydropyridazine-3,6-dione

Molecular Weight：112.09

Modify Date.: 2023-02-22 23:46

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Maleic hydrazide
1.2 Synonyms: 1,2,3,6-Tetrahydro-3,6-dioxopyridazine 1,2-dihydro 3,6-pyridazinedione 1,2-Dihydro-3,6-pyridazinedione 1,2-Dihydro-3,6-pyridazinedione,3,6-Dihydroxypyridazine,3,6-Pyridazinediol 1,2-dihydropyridazine-3,6-dione 3(2H)-Pyridazinone, 6-hydroxy- 3(2H)-Pyridazinone, tetrahydro-6-hydroxy- 3,6-Dihydroxypyridazine 3,6-dioxo-1,2,3,6-tetrahydropyridazine 3,6-Pyridazinediol 3,6-Pyridazinedione, 1,2-dihydro- 6-hydroxy-2H-pyridazin-3-one 6-Hydroxytetrahydro-3(2H)-pyridazinone Bos MH cis-Butenedioic acid hydrazide EINECS 204-619-9 Fazor gotax Hydrazide maleique KMH mAh Maleic acid cyclic hydrazide Maleic Acid Hydrazide Maleic hydrazine MFCD00006665 MG-T mH MH-30 MH-40 pyridazine-3,6-diol T6NMVJ FQ T6NNJ CQ FQ T6VMMVJ Vondalhyd Yadi Yake

1.3 CAS No.: 123-33-1

1.4 CID: 21954

1.5 EINECS(EC#): 204-619-9

1.6 Molecular Formula: C4H4N2O2 (isomer)

1.7 Inchi: InChI=1S/C4H4N2O2/c7-3-1-2-4(8)6-5-3/h1-2H,(H,5,7)(H,6,8)

1.8 InChkey: BGRDGMRNKXEXQD-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=O)NNC1=O

1.10 Isomers Smiles: C1=CC(=O)NNC1=O

2. Properties

2.1 Density: 1,6 g/cm3

2.1 Melting point: 299-301 °C (dec.)(lit.)

2.1 Boiling point: 209.98°C (rough estimate)

2.1 Refractive index: 1.4610 (estimate)

2.1 Flash Point: 300°C

2.1 Precise Quality: 112.02700

2.1 PSA: 65.72000

2.1 logP: -0.93680

2.1 Solubility: 4510mg/l

2.2 AnalyticLaboratory Methods: Reduce and hydrolyze to give hydrazine; which is distilled off and estimated colorimetrically using p-dimethylaminobenzaldehyde;.

2.3 Appearance: white cystals

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: Maleic hydrazide is a colorless crystallinesolid. Odorless.

2.6 Color/Form: Crystals from water
COLORLESS CRYSTALLINE SOLID

2.7 Corrosivity: Liquid formulated products are corrosive to brass nozzles if sprayed undiluted.

2.8 Decomposition: When heated to decomposition it emits highly toxic fumes of /nitrogen oxides/.

2.9 Heat of Combustion: -8,200 BTU/LB= -4,500 CAL/G= -190X10+5 J/KG (EST)

2.10 Odor: Odorless

2.11 Physical: MALEIC HYDRAZIDE; is an odorless white solid. Sinks in water;. (USCG, 1999)

2.12 pKa: 9.01±0.20(Predicted)

2.13 Water Solubility: 6 g/L

2.14 Spectral Properties: MAX ABSORPTION (WATER, PH 8): 215 NM (LOG EPSILON= 4.2), 340 NM (LOG EPSILON= 3.4)
IR: 543 (Sadtler Spectral Library)
UV: 2047 (Sadtler Spectral Library)
Raman: 526 (Sadtler Spectral Library)
NMR: 2800 (Sadtler Spectral Library)
MASS: 52382 (NIST/EPA/MSDC Mass Spectral database, 1990 version)

2.15 Stability: Stable under normal temperatures and pressures.

2.16 StorageTemp: 0-6°C

3. Use and Manufacturing

3.1 Agricultural Uses: Herbicide, Plant growth regulator, Fungicide: Banned for use in EU countries. Actively registeredfor use in the U.S. Maleic hydrazide is a plant growthregulator (sprout inhibitor) and herbicide that is registeredfor use on tobacco, potatoes, onions, non-bearing citrus,turf, utility and highway rights-of-way, airports, industrialland, lawns, recreational areas, ornamental/shade trees andornamental plants. Most of the use of maleic hydrazide inthe U.S. is on tobacco.

3.2 General Description: Odorless white solid. Sinks in water.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 50 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 24 of 50 companies. For more detailed information, please visit ECHA C&L website

Of the 3 notification(s) provided by 26 of 50 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (96.15%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H341 (96.15%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.4 Methods of Manufacturing: ... By treating maleic anhydride; with hydrazine hydrate; in alcohol; from maleic acid; and a hydrazine; salt of a strong inorganic acid; alternate preparation from hydrazine sulfate; and maleic anhydride; in aqueous sodium hydroxide;; alternate preparation from hydrazine hydrate; and maleic anhydride; in glacial acetic acid;.

3.5 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 useof maleic hydrazide in the United States is on tobacco.Banned for use in EU countries. Actively registered for usein the United States

3.6 Produe Method: Maleic hydrazide is slightly acidic. It is made by treatingmaleic anhydride with hydrazine hydrate in alcohol.

3.7 Purification Methods: Crystallise the hydrazide from water. Dry it at ~100o over P2O5. [Beilstein 24 III/IV 1186.]

3.8 Shipping: UN3082 Environmentally hazardous substances,liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneoushazardous material, Technical Name Required

3.9 Usage: 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.

4. Safety and Handling

4.1 Symbol: GHS07;GHS08;

4.1 Hazard Codes: Xi,Xn

4.1 Signal Word: Warning

4.1 Risk Statements: 36/37/38-40-R40-R36/37/38-68

4.1 Safety Statements: 26-36-45-36/37/39-S45-S36/37/39-S26

4.1 Octanol/Water Partition Coefficient: log Kow= -0.68 pH = 5; -1.96 at pH = 7; -2.41 at pH = 9

4.2 Fire Hazard: Special Hazards of Combustion Products: Toxic nitrogen oxides are produced.

4.3 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Recommended method of cleaning glassware and spray equipment: Formulation completely water soluble, wash and rinse equipment with water.
Personal safety precautions: Remove contaminated clothing and shoes.
Smoking, eating, drinking, /and using toilet facilities/ before washing should be absolutely prohibited when any pesticide of moderate or higher toxicity is being handled or used. /Pesticides/

4.4 Hazard Declaration: H315; H319; H335; H341

4.4 Cleanup Methods: Ventilate area of spill or leak. Collect for reclamation, or absorb in vermiculite, dry sand, earth, or a similar material.
Spillages of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: these should be removed by vacuum cleaning or by dissolving them in water or other solvent in the factory environment. In the field they may be washed away with water into a suitable soak-hole. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with a impermeable flexible membrane liner./ /Pesticides/

4.5 DisposalMethods: Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U148, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Maleic hydrazide is a potential candidate for rotary kiln incineration with a temperature range of 820 to 1600 deg C and residence times of seconds for liquids and gases, hours for solids. Also, a potential candidate for fluidized bed incineration range of 450 to 980 deg C with residence times of seconds for liquids and gases, longer for solids.
This product is relatively stable to hydrolysis but decomposes in presence of strong acids and oxidizing agents.

4.6 RIDADR: UN 3077 9/PG 3

4.6 Fire Fighting Procedures: Extinguish with water, dry chemicals, foam or carbon dioxide.

4.7 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.

4.8 Caution Statement: P261-P281-P305 + P351 + P338

4.8 Formulations/Preparations: Maleic hydrazide is available as technical grade material containing 97% min a.i. and less than 1% anionic wetting agent. It is also offered for sale as EC or WP for agricultural uses in form of its potassium salt or its diethanolamine salt. Products can contain small amount of hydrazine as impurity.
MH-30: diethanolamine salt contains 3.5 lb maleic hydrazide/imp gal. Used at 9.5-0.25% maleic hydrazide as herbicide; 0.1-0.5% as growth inhibitor and 0.025% to prevent pollen germination as 4-6 lb/acre for chemical grass mowing.
Combinations: BH 43 (with 2,4-D)
Water-soluble liquids
Royal 'MH-30', Royal 'Slo-Gro', soluble concentrate (aqueous) (160 g sodium salt/l), other liquids include: 'burtolin', 'Fazor', 'Regulox'; 'Mazide', 'Super Sucker-Stuff', soluble concentrate (1.8 kg ae potassium salt/l); 'Royal MH-30 SG', water soluble granules (600 g maleic hydrazide/kg as potassium salt). Mixtures include: 'BH 43' soluble concentrate, 'Mazide Selective' (maleic hydrazide + 2,4-D).
Burtolin
DE-CUT
FAIR PLUS
KMH
Maintain 3
Regulox 50W
Stunt-Man
SUPER DE-SPROUT
Royal MH-30
Vondalhyd
De-Sprout
Regulox
Royal Slo-Gro
Slo-Gro
Super Sprout Stop
Super Sucker-Stuff
Vondrax

4.9 Incompatibilities: Dust may form explosive mixture withair. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keepaway from alkaline materials, strong bases, strong acids,oxoacids, epoxides. Slightly corrosive to iron and zinc.Maleic hydrazide forms water-soluble alkali-metal andamine salts. It is slightly acidic and may be titrated as amonobasic acid. Mild oxidation produces a compoundwhich reacts instantly with dienes at 277C/ 2 107F toform crystalline derivatives. It is incompatible with pesticides that are highly alkaline in reaction. This chemical isslightly corrosive to iron and zinc. In the presence of heavymetal and iron, zinc, calcium, and magnesium ions,sparingly soluble salts are formed.

4.10 WGK Germany: 2

4.10 RTECS: UR5950000

4.10 Protective Equipment and Clothing: Goggles or face shield; NIOSH-certified respirator.
...Vinyl coated hand protection, natural or reclaimed rubber protection, rubber aprons, and plastic eye and face protection... used when working with small quantities. Where possibility of gross splashing exists, full protective clothing made of rubber, neoprene or vinyl-coated materials should be worn. For respiratory protection in situations where recommended tolerance limits... exceeded, respiratory protective equipment... must be used. /Hydrazine and derivatives/

4.11 Reactivities and Incompatibilities: If in presence of strong acid, maleic hydrazide acid may precipitate. Do not use concentrate through brass nozzles as the amine content may cause erosion.
Incompatible with pesticides which are highly alkaline in reaction.
Stable to hydrolysis but decomposed by concentrated oxidizing acids with the evolution of nitrogen.
In the presence of heavy-metal and iron, zinc, calcium and magnesium ions, sparingly-soluble salts are formed.

4.12 Skin, Eye, and Respiratory Irritations: Dust from or contact with the material is irritating to eyes, nose, throat, and skin.

4.13 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UR5950000

CHEMICAL NAME :: 3,6-Pyridazinedione, 1,2-dihydro-

CAS REGISTRY NUMBER :: 123-33-1

LAST UPDATED :: 199701

DATA ITEMS CITED :: 38

MOLECULAR FORMULA :: C4-H4-N2-O2

MOLECULAR WEIGHT :: 112.10

WISWESSER LINE NOTATION :: T6VMMVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >20 gm/m3

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - duck

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2 gm/kg/4W-I

TOXIC EFFECTS :: Endocrine - changes in thymus weight Immunological Including Allergic - increase in humoral immune response

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2600 mg/kg/65W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Tumorigenic - tumors at site of application

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 100 ug/L

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 7,1,1985 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 4,173,1974 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 4,173,1974 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84780 No. of Facilities: 21 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 124 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84780 No. of Facilities: 4 (estimated) No. of Industries: 1 No. of Occupations: 16 No. of Employees: 1440 (estimated)

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

ESR : TI(III) COMPLEX, IN TOLUENE/BENZENE, 77K

13C NMR : in DMSO-d6

1H NMR : 400 MHz in DMSO-d6

1H NMR : 90 MHz in DMSO-d6

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

123-33-1Total: 5 Synthesis Route

108-31-6 100 Suppliers

123-33-1 210 Suppliers

Literatures:
Edelmann, Michael J.; Raimundo, Jean-Manuel; Utesch, Nils F.; Diederich, Francois; Boudon, Corinne; Gisselbrecht, Jean-Paul; Gross, Maurice Helvetica Chimica Acta, 2002 , vol. 85, # 7 p. 2195 - 2213
Yield: ~92%

110-16-7 327 Suppliers

123-33-1 210 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 80, p. 3790
Yield: null

5343-00-0 1 Suppliers

123-33-1 210 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 80, p. 3790
Yield: null

View all

8. Precursor and Product

precursor:

5343-00-0

18259-51-3

110-16-7

64-19-7

108-31-6

product :

928-01-8

15456-83-4

669767-60-6

502-95-4

42413-70-7

16705-12-7

118923-84-5

5436-01-1

5836-40-8

37770-94-8

1945-76-2

51355-94-3

19064-67-6

141-30-0

17973-86-3

16771-17-8

2797-52-6

View all

9. Other Information

9.0 Usage: Maleic hydrazide is a synthetic plant growth regulator that is widely used for controlling growth and to induce dormancy in some crops.

10. Computational chemical data

Molecular Weight: 112.09g/mol
Molecular Formula: C₄H₄N₂O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 112.027277375
Monoisotopic Mass: 112.027277375
Complexity: 143
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 58.2
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBjMAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAHgAYAAAACACBgAAAAABiAACIACFSEACAAAAAAAIaKAAAAEAAAAAAAAAAAAAAEAAAAYAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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