Relationships Between Structure and Activity of Maleic Hydrazide Analogues and Related Compounds

Parups, E. V.; Hoffman, I.; Morley, H. V.

doi:10.1139/y62-130

Cited by 2 publications

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“…Maleic hydrazide [MH;-pyridazinone] has enjoyed extensive use as a commercial plant growth inhibitor since its introduction in 1949 (Schoene and Hoffmann, 1949). Dilution of as low as 1 ppm (Leopold and Klein, 1951) inhibits the growth of a vast multiplicity of plants, but a few derivatives of MH do not exhibit any inhibitory activity at all (Greulach, 1953;Baskokov and Melnikov, 1954; Parups et al, 1962; Greulach and Plylar, 1966). Kalinin and Troyan (1973) have confirmed and clarified earlier studies by showing that the MH-triethanolamine salt inhibited the incorporation of purine and pyrimidine bases and their nucleotides into nucleic acids, thereby inhibiting RNA and DNA synthesis (Ito and Yoshinaka, 1964;Evans and Scott, 1964;Dubinina and Dubinin, 1967;Kihlman and Hartley, 1967;Lobov, 1971Lobov, ,1973 and thus interfering with amino acid incorporation into polypeptide chains, causing the accumulation of free amino acids (Biswas et al, 1966) and decreasing the protein content of the cells (Ito and Yoshinaka, 1964;Kato, 1970;Lobov, 1971Lobov, , 1973.…”

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Incorporation of maleic hydrazide into ribonucleic acid of Saccharomyces cerevisiae

Appleton¹,

Haab²,

Eisenstadt³

et al. 1981

J. Agric. Food Chem.

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Food Chem. 1981, 29, 986-989 Johnson, A. W.; Rosebery, G.; Parker. C. Weed Res. 1976. 16. Cassady, J. M.; Howie, G. A. J. Chem. SOC., Chem. Commun. 1974, Cook, C. E.; Whichard, L. P.; Turner, B.; Wall, M. E. Science (Washington, D.C.) 1966, 154, 1189-1190. Cook, C. E.; Whichard, L. P.; Wall, M. E.; Egley, G. H.; Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Am. Chem. SOC. 1972,94, 6198-6199.Maleic hydrazide [MH; 6-hydroxy-3(2H)-pyridazinone] was incubated with Saccharomyces cerevisiae and was found to be incorporated into the RNA of the cells where it substituted for cytosine rather than for uracil, its structural isomer. Incorporation was found to take place in the undifferentiated RNA fraction, as well as in tRNA, and may explain the mode of action of MH with regard to its ability to interfere with protein biosynthesis and cell growth.

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