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Also known as: 123-33-1, 3,6-dihydroxypyridazine, 3,6-pyridazinediol, 1,2-dihydropyridazine-3,6-dione, 3,6-pyridazinedione, 1,2-dihydro-, 1,2-dihydro-3,6-pyridazinedione
Molecular Formula
C4H4N2O2
Molecular Weight
112.09  g/mol
InChI Key
BGRDGMRNKXEXQD-UHFFFAOYSA-N
FDA UNII
TQ7L3FCV66

CAS 123-33-1
1,2-Dihydro-3,6-pyridazinedione. A herbicide and plant growth regulator; also used to control suckering of tobacco. Its residue in food and tobacco is highly toxic, causing CNS disturbances and liver damage.
1 2D Structure

CAS 123-33-1

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,2-dihydropyridazine-3,6-dione
2.1.2 InChI
InChI=1S/C4H4N2O2/c7-3-1-2-4(8)6-5-3/h1-2H,(H,5,7)(H,6,8)
2.1.3 InChI Key
BGRDGMRNKXEXQD-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
TQ7L3FCV66
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Maleic Acid Hydrazide

2. Milurit

3. Milurite

2.3.2 Depositor-Supplied Synonyms

1. 123-33-1

2. 3,6-dihydroxypyridazine

3. 3,6-pyridazinediol

4. 1,2-dihydropyridazine-3,6-dione

5. 3,6-pyridazinedione, 1,2-dihydro-

6. 1,2-dihydro-3,6-pyridazinedione

7. Maleic Acid Hydrazide

8. Stuntman

9. Vondalhyde

10. Malzid

11. Retard

12. Sucker-stuff

13. Antergon

14. Antyrost

15. Malazide

16. Regulox

17. Vondrax

18. Regulox 36

19. Maleic Hydrazine

20. Sprout/off

21. De-sprout

22. Sprout-stop

23. Super-de-sprout

24. De-cut

25. Maintain 3

26. Super Sucker-stuff

27. Burtolin

28. Fazor

29. Mazide

30. Super De-sprout

31. N,n-maleoylhydrazine

32. Royal Mh-30

33. 3,6-dioxopyridazine

34. Royal Slo-gro

35. Drexel-super P

36. Regulox W

37. Super Sprout Stop

38. 6-hydroxy-3(2h)-pyridazinone

39. Fair Ps

40. Unriprim

41. Malein 30

42. Fair-2

43. Regulox 50 W

44. Fair Plus

45. Super Sucker-stuff Hc

46. Fair 30

47. Hydrazide Maleique

48. 3(2h)-pyridazinone, 6-hydroxy-

49. Maleinsaeurehydrazid

50. Mh 36 Bayer

51. Maleic Acid Cyclic Hydrazide

52. Mh 30

53. Mh-40

54. 6-hydroxy-2h-pyridazin-3-one

55. Ent 18,870

56. Hydrazid Kyseliny Maleinove

57. 1,2-dihydro-3,6-pyradizinedione

58. Malepin

59. Dtxsid9020792

60. 1,2,3,6-tetrahydro-3,6-dioxopyridazine

61. Tq7l3fcv66

62. Nsc-13892

63. 1,2,3,6-tetrahydropyridazine-3,6-dione

64. Dtxcid10792

65. Hydrazide, Maleic

66. Acid Hydrazide, Maleic

67. Hydrazide, Maleic Acid

68. Refchem:800769

69. 204-619-9

70. 600-121-4

71. Gotax

72. Milurit

73. Pyridazine-3,6-diol

74. 116595-47-2

75. Mg-t

76. Rcra Waste Number U148

77. Mfcd00006665

78. Maleic Acid, Hydrazide

79. Maleic Acid, Cyclic Hydrazide

80. Kmh

81. Mah

82. Chembl1489913

83. Chebi:81771

84. 1,6-pyridazinedione

85. 1,6-dione

86. 3, 1,2-dihydro-

87. Wln: T6vmmvj

88. F1918-0075

89. 6-hydroxy-2h-pyridazin-2-one

90. Caswell No. 352

91. Maleichydrazide

92. 1,3,6-tetrahydro-3,6-dioxopyridazine

93. Cas-123-33-1

94. Maleinsaeurehydrazid [german]

95. Maleic Hydrazide [bsi:iso]

96. Ccris 1879

97. Hsdb 1162

98. Hydrazide Maleique [iso-french]

99. Hydrazid Kyseliny Maleinove [czech]

100. Einecs 204-619-9

101. Nsc 13892

102. Rcra Waste No. U148

103. Unii-tq7l3fcv66

104. Epa Pesticide Chemical Code 051501

105. Maleinhydrazid

106. Sorbatran

107. Yadi

108. Ai3-18870

109. Meleic Hydrazide

110. Fair-plus

111. Pyridazine-3,6(1h,2h)-dione

112. Nsc-8823

113. Mfcd00071686

114. Nsc-48832

115. Maleic Cyclic Hydrazide

116. Maleic Hydrazide (standard)

117. Pyridazine, 3,6-dihydroxy-

118. Schembl55071

119. Maleic Hydrazide [mi]

120. Schembl154932

121. Schembl554403

122. Schembl554404

123. Maleic Hydrazide [iso]

124. Orb1705423

125. Orb3139811

126. Schembl3678851

127. Schembl4138427

128. Schembl7277672

129. Schembl8536307

130. Maleic Hydrazide [hsdb]

131. Maleic Hydrazide [iarc]

132. Schembl29740320

133. Nsc8823

134. Smssf-0044116

135. Albb-020885

136. Msk24017

137. Nsc13892

138. Nsc48832

139. Str03411

140. Tox21_201829

141. Tox21_300662

142. Bdbm50021573

143. Ebc-12511

144. Ebc-44277

145. Hy-59354r

146. Sbb004322

147. Stk357922

148. Akos000121025

149. Akos000275072

150. Akos017269103

151. Fm15520

152. Ks-5282

153. Maleic Hydrazide, Reagentplus(r), 99%

154. Ncgc00091173-01

155. Ncgc00091173-02

156. Ncgc00091173-03

157. Ncgc00091173-04

158. Ncgc00254570-01

159. Ncgc00259378-01

160. Ac-11591

161. Hy-59354

162. Db-028316

163. Cs-0007730

164. M0015

165. Ns00005908

166. St50807893

167. En300-17761

168. C18474

169. Maleic Hydrazide, Vetec(tm) Reagent Grade, 98%

170. Ac-907/30002020

171. Q677933

172. Maleic Hydrazide, Pestanal(r), Analytical Standard

173. Z57032544

174. 1,2-dihydropyridazine-3,6-dione; 6-hydroxy-3-pyridazinone

175. 3,6-pyridazinediol; Maleic Acid Hydrazide; Maleic Hydrazide

176. Inchi=1/c4h4n2o2/c7-3-1-2-4(8)6-5-3/h1-2h,(h,5,7)(h,6,8

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 112.09 g/mol
Molecular Formula C4H4N2O2
XLogP3-0.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area58.2
Heavy Atom Count8
Formal Charge0
Complexity143
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antimetabolites

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)


Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.


Gout Suppressants

Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout.


Herbicides

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.


Plant Growth Regulators

Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.


Free Radical Scavengers

Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY.


4.2 Absorption, Distribution and Excretion

...After oral doses of 100 mg/kg bw, rabbits excreted 43 to 62% maleic hydrazide unchanged in urine within 48 hr.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work).


(14)C Maleic hydrazide was administered orally to rats. After 3 days, very little (14)C activity was detected in tissues or blood and carbon dioxide accounted for only 0.2% of administered dose. Maleic hydrazide was rapidly excreted via urine unchanged (>90%) and as conjugate (6-8%).

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 236


Slowly absorbed over period of 24 hr by quackgrass. Rain within this period will reduce effectiveness. Rate of absorption is function of cell turgidity. Most effective absorption occurs when soil moisture is at field capacity and relative high humidity. Translocates more effectively downward. Once absorbed, maleic hydrazide is freely translocated to active growing points in plant. maleic hydrazide becomes fixed within the plant and is not metabolized.

Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 323


In white ash and black locust seedlings, most of maleic hydrazide was translocated to leaves and stems of black locust seedlings within 1 day after treatment, but for white ash seedlings it remained in the stem tissue. After 30 days, the (14)C was concentrated in the leaves of the black locust seedlings, but only in the stem and at the injection point of white ash seedlings. Chromatography of the extracts showed no detectable metabolite in black locust seedlings, but 2 metabolites were detected in the white ash seedlings.

Mischke CF, Domir SC; Pestic Sci 13 (3): 304-8 (1982)


For more Absorption, Distribution and Excretion (Complete) data for MALEIC HYDRAZIDE (10 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

When applied to tea, Camelia sinensis, MH /(maleic hydrazine)/ was degraded to lactic acid, succinic acid, maleimide and hydrazine. Extracts of treated wheat seedlings... identified... beta-glycoside of MH. ...In presence of oxygen, MH undergoes photolysis to form succinic, maleic and nitric acid; and in absence of oxygen... succinic acid.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 236


When applied to silver maple... and American sycamore... seedlings, maleic hydrazide translocated to all parts of the plant. In the plant tissue, a metabolite was formed. Hydrolysis products of the metabolite indicated a conjugate of maleic hydrazide and glucose. When applied to tobacco plants, (14)C maleic hydrazide was rapidly translocated to growing tissues. Translocation to roots also occurred. A small amount of (14)CO2 evolved. The major metabolite in foliar tissues was identified as the beta-D-glucoside of maleic hydrazide.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 391


In one radio label experiment in rats, 77% of the administered radioactivity was recovered in urine within 6 days. 90% of the activity was found to be unaltered maleic hydrazide. The remainder was present as a conjugate of MH.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-343


In rats, the urine and feces samples /collected following oral administration of 3,6-dione-labelled 14C-maleic hydrazide/ contained two peaks. Poor chromatographic separation and low levels of radiolabel in the fecal samples precluded reliable identification, but the peaks appeared to represent maleic hydrazide and possibly fumaric acid. The major peak in urine, representing 60% of the urinary radiolabel in males and 80% in females, co-chromatographed with maleic hydrazide. The minor urinary peak was initially found to co-chromatograph with maleimide, fumaric acid, or maleic diamide, depending on the solvent system, but subsequent investigation with deconjugation with a beta-glucuronidase containing sulfatase activity and HPLC showed this peak to be a maleic acid conjugate, probably a sulfate.

FAO/WHO Joint Meeting on Pesticide Residues; Maleic hydrazide (Pesticide Residues in Food: 1996 Evaluations). Available from, as of April 15, 2004: https://www.inchem.org/documents/jmpr/jmpmono/v96pr08.htm


For more Metabolism/Metabolites (Complete) data for MALEIC HYDRAZIDE (7 total), please visit the HSDB record page.


4.4 Mechanism of Action

Maleic hydrazide inhibits mitosis in actively growing tissues of treated plants and also has profound effects on rate of respiration. ... Maleic acid ... reacts with -SH compounds ... /and/ competes with receptor sites of ... succinic dehydrogenase. ... Inhibition ... may represent site of action ... in plants.

White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 65


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