Maleic Hydrazide
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Basic Info
Common Name | Maleic 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 ID | F05096 |
CAS Number | 123-33-1 |
PubChem CID | 21954 |
Formula | C4H4N2O2 |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organoheterocyclic compounds |
Class | Diazines |
Subclass | Pyridazines and derivatives |
Intermediate Tree Nodes | Not available |
Direct Parent | Pyridazinones |
Alternative Parents | |
Molecular Framework | Aromatic heteromonocyclic compounds |
Substituents | Pyridazinone - Heteroaromatic compound - Lactam - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound |
Description | This compound belongs to the class of organic compounds known as pyridazinones. These are compounds containing a pyridazine ring which bears a ketone. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 112.088 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 0 |
Complexity | 143 |
Monoisotopic Mass | 112.027 |
Exact Mass | 112.027 |
XLogP | -0.8 |
Formal Charge | 0 |
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 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9924 |
Human Intestinal Absorption | HIA+ | 0.9903 |
Caco-2 Permeability | Caco2- | 0.5074 |
P-glycoprotein Substrate | Non-substrate | 0.8098 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9586 |
Non-inhibitor | 0.9971 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9218 |
Distribution | ||
Subcellular localization | Mitochondria | 0.8575 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8822 |
CYP450 2D6 Substrate | Non-substrate | 0.8304 |
CYP450 3A4 Substrate | Non-substrate | 0.6876 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8959 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9811 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9454 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9796 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9739 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9898 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9669 |
Non-inhibitor | 0.9705 | |
AMES Toxicity | Non AMES toxic | 0.5414 |
Carcinogens | Non-carcinogens | 0.8792 |
Fish Toxicity | Low FHMT | 0.7810 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.5621 |
Honey Bee Toxicity | Low HBT | 0.7997 |
Biodegradation | Not ready biodegradable | 0.9460 |
Acute Oral Toxicity | III | 0.7778 |
Carcinogenicity (Three-class) | Non-required | 0.7062 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -1.0840 | LogS |
Caco-2 Permeability | 1.0301 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.5014 | LD50, mol/kg |
Fish Toxicity | 2.4364 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.3270 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Parsnip | Japan | 30ppm | |||
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.2* | 05/06/2018 | |
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.2* | 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... | 0154010 | European Union | 0.2* | 05/06/2018 | |
Miscellaneous fruits with | 0160000 | European Union | 0.2* | 05/06/2018 | |
Table olives (Chinese black olives, Chinese white olives, Desert dates,) | 0161030 | European Union | 0.2* | 05/06/2018 | |
Onions ('Cipollotto Nocerino PDO', Pearl onions, Rakkyo/Chinese onions, Silverskin onions/pickled onions,) | 0220020 | European Union | 15 | 05/06/2018 | |
FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.2* | 05/06/2018 | |
Citrus fruits | 0110000 | European Union | 0.2* | 05/06/2018 | |
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.2* | 05/06/2018 | |
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.2* | 05/06/2018 | |
Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.2* | 05/06/2018 | |
Others (2) | 0110990 | European Union | 0.2* | 05/06/2018 | |
Tree nuts | 0120000 | European Union | 0.2* | 05/06/2018 | |
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.2* | 05/06/2018 | |
Brazil nuts | 0120020 | European Union | 0.2* | 05/06/2018 | |
Cashew nuts | 0120030 | European Union | 0.2* | 05/06/2018 | |
Chestnuts | 0120040 | European Union | 0.2* | 05/06/2018 | |
Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.2* | 05/06/2018 | |
Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.2* | 05/06/2018 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Brachypodium distachyon - A Useful Model in the Qualification of Mutagen-Induced Micronuclei Using Multicolor FISH. | PLoS One | 2017 Jan 24 | 28118403 |
Determination of Glyphosate, Maleic Hydrazide, Fosetyl Aluminum, and Ethephon in Grapes by Liquid Chromatography/Tandem Mass Spectrometry. | J Agric Food Chem | 2017 Aug 30 | 28759225 |
Multi-residue analysis of pesticides, plant hormones, veterinary drugs and mycotoxins using HILIC chromatography - MS/MS in various food matrices. | Anal Chim Acta | 2016 Oct 26 | 27720116 |
Fast determination of four polar contaminants in soy nutraceutical products byliquid chromatography coupled to tandem mass spectrometry. | Anal Bioanal Chem | 2016 Nov | 27595581 |
The Use of Maleic Hydrazide for Effective Hybridization of Setaria viridis. | PLoS One | 2015 Apr 24 | 25910193 |
Rapid detection of pesticides not amenable to multi-residue methods by flowinjection-tandem mass spectrometry. | Anal Bioanal Chem | 2014 Nov | 24518902 |
Cell division interference in newly fertilized ovules induces stenospermocarpy incross-pollinated citrus fruit. | Plant Sci | 2014 Aug | 25017163 |
Genotoxic assessment and optimization of pressmud with the help of exotic earthworm Eisenia fetida. | Environ Sci Pollut Res Int | 2014 | 24671397 |
Determination of maleic hydrazide residues in garlic bulbs by HPLC. | Talanta | 2012 Jan 30 | 22284504 |
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 Biol | 2010 Nov-Dec | 21146138 |
[Simple analysis of maleic hydrazide in agricultural products by HPLC]. | Shokuhin Eiseigaku Zasshi | 2002 Dec | 12635338 |
Aquatic humic substances inhibit clastogenic events in germinating seeds ofherbaceous plants. | J Agric Food Chem | 2001 Mar | 11312910 |
The carry-through of residues of maleic hydrazide from treated potatoes,following manufacture into potato crisps and 'jacket' potato crisps. | Food Addit Contam | 1998 Jul | 9829033 |
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 A | 1996 Oct 25 | 8938394 |
Effects of pesticides on isolated rat hepatocytes, mitochondria, and microsomes. | Arch Environ Contam Toxicol | 1993 Aug | 8368870 |
Cytotoxic effects of maleic hydrazide. | Mutat Res | 1978 | 368621 |
Anti-tumorigenic effect of maleic hydrazide on mouse skin. | J Agric Food Chem | 1976 May-Jun | 818144 |
Collaborative study of a spectrophotometric method for determining maleic hydrazide residues in tobacco and vegetables. | J Assoc Off Anal Chem | 1975 Nov | 1194188 |
Rapid determination of maleic hydrazide cigarette smoke condensate and particulate matter. | J Agric Food Chem | 1974 Nov-Dec | 4430794 |
A rapid quantitative method for maleic hydrazide. | J Agric Food Chem | 1974 Mar-Apr | 4840583 |