Basic Info

Common NameMaleic Hydrazide(F05096)
2D Structure
Description

Maleic hydrazide (MH) was introduced into agriculture in the 1950s as a major commercial herbicide and a depressant of plant growth. It is a plant growth regulator (sprout inhibitor) and herbicide, that acts by inhibiting cell division in plants. It is used to control sprouting of potatoes and onions, suckers in tobacco, and growth of weeds, grasses and trees in/along lawns, turf, ornamental plants, non-bearing citrus, utility and highway rights-of-way, airports and industrial land. Most of the maleic hydrazide used in the U.S. is applied to tobacco (86-88%), followed by potatoes (10%), It is used to control sucker growth on tobacco plants, retardation of flowering and prolongation of dormancy period.

FRCD IDF05096
CAS Number123-33-1
PubChem CID21954
FormulaC4H4N2O2
IUPAC Name

1,2-dihydropyridazine-3,6-dione

InChI Key

BGRDGMRNKXEXQD-UHFFFAOYSA-N

InChI

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

Canonical SMILES

C1=CC(=O)NNC1=O

Isomeric SMILES

C1=CC(=O)NNC1=O

Synonyms
        
            Pyridazine-3,6-diol
        
            MALEIC HYDRAZIDE
        
            123-33-1
        
            3,6-Dihydroxypyridazine
        
            3,6-Pyridazinediol
        
            1,2-Dihydropyridazine-3,6-dione
        
            Maleic acid hydrazide
        
            Stuntman
        
            Vondalhyde
        
            3,6-Pyridazinedione, 1,2-dihydro-
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDiazines
SubclassPyridazines and derivatives
Intermediate Tree NodesNot available
Direct ParentPyridazinones
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPyridazinone - Heteroaromatic compound - Lactam - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyridazinones. These are compounds containing a pyridazine ring which bears a ketone.

Properties

Property NameProperty Value
Molecular Weight112.088
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Complexity143
Monoisotopic Mass112.027
Exact Mass112.027
XLogP-0.8
Formal Charge0
Heavy Atom Count8
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9924
Human Intestinal AbsorptionHIA+0.9903
Caco-2 PermeabilityCaco2-0.5074
P-glycoprotein SubstrateNon-substrate0.8098
P-glycoprotein InhibitorNon-inhibitor0.9586
Non-inhibitor0.9971
Renal Organic Cation TransporterNon-inhibitor0.9218
Distribution
Subcellular localizationMitochondria0.8575
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8822
CYP450 2D6 SubstrateNon-substrate0.8304
CYP450 3A4 SubstrateNon-substrate0.6876
CYP450 1A2 InhibitorNon-inhibitor0.8959
CYP450 2C9 InhibitorNon-inhibitor0.9811
CYP450 2D6 InhibitorNon-inhibitor0.9454
CYP450 2C19 InhibitorNon-inhibitor0.9796
CYP450 3A4 InhibitorNon-inhibitor0.9739
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9898
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9669
Non-inhibitor0.9705
AMES ToxicityNon AMES toxic0.5414
CarcinogensNon-carcinogens0.8792
Fish ToxicityLow FHMT0.7810
Tetrahymena Pyriformis ToxicityHigh TPT0.5621
Honey Bee ToxicityLow HBT0.7997
BiodegradationNot ready biodegradable0.9460
Acute Oral ToxicityIII0.7778
Carcinogenicity (Three-class)Non-required0.7062

Model Value Unit
Absorption
Aqueous solubility-1.0840LogS
Caco-2 Permeability1.0301LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5014LD50, mol/kg
Fish Toxicity2.4364pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.3270pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
ParsnipJapan30ppm
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.2*05/06/2018
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.2*05/06/2018
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.2*05/06/2018
Miscellaneous fruits with0160000European Union0.2*05/06/2018
Table olives (Chinese black olives, Chinese white olives, Desert dates,)0161030European Union0.2*05/06/2018
Onions ('Cipollotto Nocerino PDO', Pearl onions, Rakkyo/Chinese onions, Silverskin onions/pickled onions,)0220020European Union1505/06/2018
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.2*05/06/2018
Citrus fruits0110000European Union0.2*05/06/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.2*05/06/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.2*05/06/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.2*05/06/2018
Others (2)0110990European Union0.2*05/06/2018
Tree nuts0120000European Union0.2*05/06/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.2*05/06/2018
Brazil nuts0120020European Union0.2*05/06/2018
Cashew nuts0120030European Union0.2*05/06/2018
Chestnuts0120040European Union0.2*05/06/2018
Coconuts (Areca nuts/betel nuts,)0120050European Union0.2*05/06/2018
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.2*05/06/2018

References

TitleJournalDatePubmed ID
Brachypodium distachyon - A Useful Model in the Qualification of Mutagen-Induced Micronuclei Using Multicolor FISH.PLoS One2017 Jan 2428118403
Determination of Glyphosate, Maleic Hydrazide, Fosetyl Aluminum, and Ethephon in Grapes by Liquid Chromatography/Tandem Mass Spectrometry.J Agric Food Chem2017 Aug 3028759225
Multi-residue analysis of pesticides, plant hormones, veterinary drugs and mycotoxins using HILIC chromatography - MS/MS in various food matrices.Anal Chim Acta2016 Oct 2627720116
Fast determination of four polar contaminants in soy nutraceutical products byliquid chromatography coupled to tandem mass spectrometry.Anal Bioanal Chem2016 Nov27595581
The Use of Maleic Hydrazide for Effective Hybridization of Setaria viridis.PLoS One2015 Apr 2425910193
Rapid detection of pesticides not amenable to multi-residue methods by flowinjection-tandem mass spectrometry.Anal Bioanal Chem2014 Nov24518902
Cell division interference in newly fertilized ovules induces stenospermocarpy incross-pollinated citrus fruit.Plant Sci2014 Aug25017163
Genotoxic assessment and optimization of pressmud with the help of exotic earthworm Eisenia fetida.Environ Sci Pollut Res Int201424671397
Determination of maleic hydrazide residues in garlic bulbs by HPLC.Talanta2012 Jan 3022284504
Enzymatic adaptations to arsenic-induced oxidative stress in Zea mays andgenotoxic effect of arsenic in root tips of Vicia faba and Zea mays.C R Biol2010 Nov-Dec21146138
[Simple analysis of maleic hydrazide in agricultural products by HPLC].Shokuhin Eiseigaku Zasshi2002 Dec12635338
Aquatic humic substances inhibit clastogenic events in germinating seeds ofherbaceous plants.J Agric Food Chem2001 Mar11312910
The carry-through of residues of maleic hydrazide from treated potatoes,following manufacture into potato crisps and 'jacket' potato crisps.Food Addit Contam1998 Jul9829033
Extraction of maleic hydrazide residues from potato crisps and theirdetermination using high-performance liquid chromatography with UV andatmospheric pressure chemical ionisation mass spectrometric detection.J Chromatogr A1996 Oct 258938394
Effects of pesticides on isolated rat hepatocytes, mitochondria, and microsomes.Arch Environ Contam Toxicol1993 Aug8368870
Cytotoxic effects of maleic hydrazide.Mutat Res1978368621
Anti-tumorigenic effect of maleic hydrazide on mouse skin.J Agric Food Chem1976 May-Jun818144
Collaborative study of a spectrophotometric method for determining maleic hydrazide residues in tobacco and vegetables.J Assoc Off Anal Chem1975 Nov1194188
Rapid determination of maleic hydrazide cigarette smoke condensate and particulate matter.J Agric Food Chem1974 Nov-Dec4430794
A rapid quantitative method for maleic hydrazide.J Agric Food Chem1974 Mar-Apr4840583