Abstract
In 1949 Schoene and Hoffmann reported that maleic hydrazide (MH) had a pronounced but temporary inhibitory effect on plant growth causing little visible harm to the plant. Although its properties are better represented by the structure 6-hydroxy-3(2H) pyridazinone, MH is usually defined chemically as l,2-dihydro-3,6-pyridazinedione. Proliferation of its use as an herbicide, fungicide, growth inhibitor, and growth regulator followed quickly. Currently it is enjoying very wide use due to its relative safety in spite of some reservations which have been expressed over certain of its side effects.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Andersen, O.: Studies on the absorption and translocation of Amitrol (3-amino-1,2,4-triazole) by nut grass (Cyperus rotundus L.). Weeds 6, 370 (1958).
Andreae, W. A., and S. R. Andreae: Studies on indoleacetic acid metabolism. I. The effect of methyl umbelliferone, maleic hydrazide and 2,4-D on indoleacetic acid oxidation. Can. J. Botan. 31, 426 (1953).
Andreae, W. A., and S. R. Andreae Effect of maleic hydrazide on indoleacetic acid oxidase activity and growth. Congr. Intern. Botan. Rapps. et communi. 8, 151 (1954).
Andreae, W. A., and S. R. Andreae The photoinduced oxidation of manganous ions. Arch. Biochem. Biophys. 55, 584 (1955).
Andreae, W. A., and S. R. Andreae The estimation of maleic hydrazide by paper chromatography. Can. J. Biochem. Physiol. 36, 71 (1958).
Anglin, C., and J. H. Mahon: A modified procedure for determining maleic hydrazide residues in plant material. J. Assoc. Official Agr. Chemists 41, 177 (1958).
Baker, J. E.: A study of the action of maleic hydrazide on processes of tobacco and other plants. Physiol. Plantarum 14, 76 (1961).
Barnes, J. M., P. N. Magee, E. Boyland, A. Haddow, R. D. Passey, W. S. Bullough, C. N. D. Cruickshank, M. H. Salaman, and R. T. Williams: The non-toxicity of maleic hydrazide for mammalian tissues. Nature 180, 62 (1957).
Bertossi, F.: Antagonistes synthétiques de crossance. L’Année Biolog. 31, 231 (1955).
Bertossi, F., and A. Capozzi: Action of maleic hydrazide on hardening of vegetable tissues in vitro. Bull. Soc. Ital. Biol. Sper. 28, 1117 (1952).
Birch, E. C., and L. S. Vickery: TTie effect of maleic hydrazide on certain chemical constituents of flue-cured tobacco. Can. J. Plant Sei. 41, 170 (1961).
Blomquist, V. H.: Report on the determination of maleic hydrazide in plant and animal tissues. J. Assoc. Official Agr. Chemists 42, 562 (1959).
Brian, P. W., and H. G. Hemming: The effect of maleic hydrazide on the growth response of plants to gibberellic acid. Ann. Appl. Biol. 45, 489 (1957).
Brown, M. S., and C. W. Hitz: An interpretation of the influence of maleic hydrazide upon the growth of strawberry runners based upon radioisotope studies. Proc. Amer. Soc. Hort. Sei. 70, 131 (1957).
Butenko, R. G., and Yu. A. Baskakov: On the mechanism of the effect of maleic hydrazide on plants. Plant Physiol. (Fiziol. Rastenii) 7, 323 (1961).
Callaghan, J. J., and P. Grun: Incorporation of C14-labelled maleic hydrazide into the root tips of Allium cernuum, Vicia faba, and Tradescantia paludosa. J. Biophys. Biochem. Cytol. 10, 567 (1961).
Carlson, J. B.: Cytohistological responses of plant meristems to maleic hydrazide. J. Sei. Iowa State College 29, 105 (1954).
Choudhury, B., and S. C. Phatak: Further studies on sex-expression and sex-ratio in cucumber (Cucumis sativus L.) as affected by plant regulator sprays. Ind. J. Hort. 17, 210 (1960).
Coulson, D. A.: Some effects of maleic hydrazide on flue-cured tobacco quality. Tobacco Sei. 3, 69 (1959).
Crafts, A. S.: Further studies on comparative mobility of labelled herbicides. Plant Physiol. 34, 613 (1959).
Crafts, A. S. The chemistry and mode of action of herbicides. Chapter 15. New York—London: Interscience 1961.
Crafts, A. S., and S. Yamaguchi: Comparative tests on the uptake and distribution of labelled herbicides by Zebrina pendula andTradescantia fluminensis. Hilgardia 27, 421 (1958).
Crafts, A. S., and S. Yamaguchi Absorption of herbicides by roots. Amer. J. Botany 47, 248 (1960).
Crafts, A. S., and S. Yamaguchi, and C. L. Foy: The chemical and physical nature of plant surfaces in relation to the use of pesticides and to their residues. Residue Reviews 1, 112 (1962).
Currier, H. B., B. E. Day, and A. S. Crafts: Some effects of maleic hydrazide on plants. Botan. Gaz. 112, 272 (1951).
Curtius, T.., and H. A. Foesterling: Hydrazide und Azide organischer Säuren; 28,Über die Einwirkung von Hydrazinhydrat auf Phtalsäure- und Maleinsäureanhydrid. J. f. prakt. Chemie 51, 371 (1895).
Darlington, C. D., and J. McLeish: Action of maleic hydrazide on the cell. Nature 167, 407 (1951).
Deyson, G., and M. Deyson: Biochemical mechanism of action of mitotic poisons. 1. Does the external application of uracil oppose the mitostatic action exerted by barbital, antipyrine and maleic hydrazide. Bull. Soc. Chem. Biol. 35, 1209
Dormal, S., and H. Hurtig: Principles for the establishment of pesticide residue tolerances. Residue Reviews 1, 140 (1962).
Dugnani, E. M.: Inhibiting effect of antiauxins on some dehydrogenase enzyme systems in the soluble and in the particulate fractions of extracts from plant tissues. Nuovo Giorn. Bot. Ital. 61, 214 (1954).
Ermolayeva, E. A., N. A. Kozlova, P. Batska, M. A. Bhilova, and M. E. Vasilyeva: The effect of maleic hydrazide on the rate of photosynthesis and on the carbohydrate metabolism of plants. Experiment. Botan. Akad. Nauk SSSR. Botan. Inst. im. B. L. Komarova Ser. 4, 120 (1962).
Federal Register: Tolerances for residues of maleic hydrazide. Vol. 25, no. 49, section 120.175 (1960 a).
Federal Register Maleic hydrazide in potato chips. Vol. 25, no. 49, section 121.1006 (1960 b).
Feuer, H., and R. Harmetz: The reactions of maleic hydrazide with formaldehyde and alcohols in acidic medium. J. Org. Chem. 24, 1501 (1959).
Feuer, H., and H. Rubinstein: Preparation of l-(3’,1’H,6’-pyridazinone)-3,6-pyridazine- dione. Attempts to prepare bicyclic dimaleic hydrazide. J. Org. Chem. 24, 811 (1959).
Fischnich, O., Ch. Pätzold, and C. Schiller: Wachstumsregulatoren im Kartoffelbau. European Potato J. 1, 25 (1958).
Fletcher, W. W.: The effect of herbicides on soil micro-organisms. In: Herbicides and the soil, ed. E. K. Woodford and G. R. Sagar. Oxford: Blackwell 1960.
Frans, R. E., E. F. Lind, and W. E. Loomis: Kinetics of growth inhibition by herbicides. Plant Physiol. 32, 301 (1957).
Gaines, J. G.: Influence of maleic hydrazide in relation to other practices on flue-cured tobacco production. Tobacco Sei. 3, 75 (1959).
Galun, E.: Effects of gibberellic acid and naphthaleneacetic acid on sex expression and some morphological characters in the cucumber plant. Phyton 13, 1 (1959).
Gompper, R., and P. Altreuther: Carbonsäurederivative. II. Untersuchungen an Verbindungen mit Amidstruktur (IR- und protonmagnetische Resonanz-Spektren). Zeitschrift f. anal. Chem. 169, 205 (1959).
Grebenschikova, M. P., K. V. Mukhorina, and S. G. Bogomolov: Absorption spectra of the extracts of potatoes, processed with the maleic hydrazide diethanolamine salt. Voprosi Pitaniya 3, 60 (1961).
Greulach, V. A.: A search for antagonists of maleic hydrazide. J. Tenn. Acad. Sei.29,179 (1954).
Greulach, V. A. Pyrimidines as antagonists of maleic hydrazide. J. Elisha Mitchell Sei. Soc. 71, 2 (1955).
Greulach, V. A. Screening tests of hydrazides, pyridazine derivatives and related compounds for possible influence on plant growth and development. J. Elisha Mitchell Sei. Soc. 77, 65 (1961).
Greulach, V. A., and J. G. Haesloop: A paper chromatographic technique for hydrazides and certain metabolites. Anal. Chem. 33, 1446 (1961).
Haber, A. H., and J. D. White: Action of maleic hydrazide on dormancy, cell division and cell expansion. Plant Physiol. 35, 495 (1960).
Harris, J. B., and J. D. Miles: Some effects of urea and maleic hydrazide on flue-cured tobacco. Tobacco Sci. 5, 128 (1961).
Haskins, F. A., and H. W. Chapman: Effects of irradiation, maleic hydrazide, temperature and age on enzyme activity in seedlings of corn, Zea mays L. Physiol. Plantarum 9, 356 (1956).
Hendershott, C. H.: Absorption of maleic hydrazide by citrus. Proc. Amer. Soc. Hort. Sci. 80, 237 (1962 a).
Hendershott, C. H. The influence of maleic hydrazide on citrus trees and fruits. Proc. Amer. Soc. Hort. Sci. 80, 241 (1962 b).
Heslop-Harrison, J.: The experimental modifications of sex expression in flowering plants. Biol. Rev. 32, 38 (1957).
Hillman, W. S., and A. W. Galston: The effect of external factors on auxin content. In: Encyclopedia of plant physiol., Vol. 14, p. 682. Berlin-GottingenHeidelberg: Springer 1961.
Hillyer, I. G.: Effect of growth substances on flowering of cucurbitaceous plants. Ph. D. dissertation. Mich. State Univ., East Lansing 1956.
Hoffman, I.: Spectrophotometric determination of maleic hydrazide in tobaccos. J. Assoc. Official Agr. Chemists 44, 723 (1961).
Hoffman, I., and R. B. Carson: Determination and distribution of maleic hydrazide in vegetables and fruits. J. Assoc. Official Agr. Chemists 45, 788 (1962).
Hoffman, I., E. V. Parups, and R. B. Carson: Analysis for maleic hydrazide. J. Agr. Food Chem. 10, 453 (1962).
Hughes, C., and S. P. Spragg: The inhibition of mitosis by the reaction of maleic hydrazide with sulfhydryl groups. Biochem. J. 70, 205 (1958).
Isenberg, F. M. R.: The effect of maleic hydrazide on plants. Ph. D. dissertation. Penn. State Univ., University Park 1954.
James, B. L.: Absorption and translocation of maleic hydrazide in Taxus media ’Brown’ as determined with a radioisotope. Dissertation Abstr. 20, 1944 (1959).
Kanehisa, T.: Tests of chemical substances and specific genes for their effects on tumor incidence inD. melanogaster. Amer. Naturalist 91, 393 (1957).
Kessler, B., and Z. W. Moscicki: Effect of triiodobenzoic acid and maleic hydrazide upon the transport of foliar applied calcium and iron. Plant Physiol. 33, 70 (1958).
Kulescha, Z.: Action of maleic hydrazide on the auxin content of tissue of Jerusalem artichoke grown in presence of various division substances. Acta Botan. Neerl. 4, 404 (1955).
Lane, J. R., D. K. Gullstrom, and J. E. Newell: Extension of the residue methods for l,2-dihydro-3,6-pyridazinedione (maleic hydrazide) and 7V-l-naphthyl- phthalamic acid (Alanap). J. Agr. Food Chem. 6, 671 (1958).
Leopold, A. C., and W. H. Klein: Maleic hydrazide as an anti-auxin. Science 114, 9 (1951).
Leopold, A. C., and W. H. Klein Maleic hydrazide as an anti-auxin. Physiol. Plantarum 5, 91 (1952).
Levi, E., and A. S. Crafts: Toxicity of maleic hydrazide in California soils. Hilgardia 21, 431 (1952).
Libbert, E.: Das indolessigsaure-bildende Enzymsystem aus Erbsenpflanzen. Zeit- schrift f. Botan. 48, 365 (1960).
Lockhart, J. A.: Kinetic studies of certain anti-gibberellins. Plant Physiol. 37, 759 (1962).
Maheshwari, P., C. Satish and Nirmala: Some aspects of physiology of reproduction. Trans. Bose Research Inst. Calcutta 22, 205 (1958).
Mannell, W. A., and H. C. Grice: A comparative study of the effects of maleic hydrazide and p-dimethylaminoazobenzene on rat liver. Can. J. Biochem. Physiol. 35, 1233 (1957).
McEvoy, E. T., and I. Hoffman: The use of chemicals to suppress sucker growth on cigar tobacco. Can. J. Plant Sci. 39, 350 (1959).
McIlraith, W. J.: The use of maleic hydrazide for the production of male sterility in grain sorghum. Presented at meeting of Amer. Soc. of Plant Physiol., Madison, W.Sconsin 1953
McManus, M. A.: Certain mitotic effects of kinetin, gibberellic acid, maleic hydrazide and indoleacetic acid in onion roots. Proc. Iowa Acad. Sei. 66, 74 (1959).
Merz, T., C. P. Swanson, and N. S. Cohn: Interaction between chromatid breaks produced by X-rays and radiomimetic compounds. Science 133, 703 (1961).
Milad, L., and M. El-Shehat: The volumetric assay of maleic hvdrazide. Pharm. Soc. Egypt. Proc. Sei. Ed. 36, 43 (1954).
Miller, D. M., and W. R. White: The structure of maleic hydrazide as inferred from the ultraviolet spectra of its methyl derivatives. Can. J. Chem. 34, 1510 (1956).
Moore, R. H.: Several effects of maleic hydrazide in plants. Science 112, 52 (1950).
Moseley, J. M.: The effects of maleic hydrazide when used as a sucker control agent upon the quality of flue-cured tobacco. Tobacco Sei. 3, 73 (1959).
Moutschen, J., M. Dahmen, and C. Gillet: Sur les modifications induites par les hydrazides maléique et isonicotinique dans les anthéridies deChara vulgaris L. La Cellule 58, 65 (1956–1957).
Muir, R. M., and C. Hansch: On the mechanism of action of growth regulators. Plant Physiol. 28, 218 (1955).
Mukherjee, R. N.: Effect of chromosome uncoiling on the induction of chromosome breakage by maleic hydrazide in Vicia faba. Nucleus 4, 145 (1961).
Nagai, Y.: Micro-determination of maleic hydrazide by reductive cleavage with zinc in sulphuric acid. J. Agr. Chem. Soc. Japan 32, 851 (1958).
Naylor, A. W.: Investigations in the chemical control of flowering. Rept. of 5th Hybrid Corn Ind. Research Conference, Chicago 1950.
Naylor, A. W., and E. A. Davis: Respiration response of root tips to maleic hydrazide. Bull. Torrey Bot. Club 78, 73 (1951).
Nickell, L. G.: Nutrition of pathological tissues caused by plant viruses. L’Année Biol. 31, 307 (1955).
Parups, E. V.: The effect of 2,3-dichloro-l,4-naphthoquinone on maleic hydrazide treated greenhouse-grown tobacco. Tobacco Sei. 6, 7 (1962).
Parups, E. V., I. Hoffman, and H. V. Morley: Relationships between structure and activity of maleic hydrazide analogues and related compounds. Can. J. Biochem. Physiol. 40, 1159 (1962).
Parups, E. V., and J. Richard: The effect of various quinones on maleic hydrazide treated field grown flue-cured tobacco. Tobacco Sei. 6, 119 (1962).
Parups, E. V., and F. H. White: The effect of maleic hydrazide and 2,3-dichloro-l,4- naphthoquinone on field-grown cigar tobacco. Tobacco Sei. 7, 128 (1963).
Pilet, P. E.: Action of maleic hvdrazide on in vivo auxin destruction. Physiol. Plantarum 10, 791 (1957).
Porter, K. B., and A. F. Wiese: Evaluation of certain chemicals as selective gametocides for wheat. Crop. Sei. 1,381 (1961).
Povolotskaya, K. L.: On the mechanism of the action of maleic hydrazide in plants. Izvest. Akad. Nauk SSSR. Biol. Ser. No. 2, 250 (1961).
Powell, E. N., and R. C. Andreasen: Responses of bench-grown Chrysanthemum morifolium to maleic hydrazide. Proc. Amer. Soc. Hort. Sei. 70, 482 (1957).
Rakitin, Y.. V., and R. A. Svarinskaya: Effect of maleic hydrazide on physiological changes in the potato. Plant. Physiol. (Fiziol. Rastenii) 4, 139 (1957).
Rakitin, Y.. V., and A. V. Krylov: A study of the translocation, distribution and transformation of some physiologically active substances in plants. Proc. 2nd U. N. Internat. Conf. on Peaceful Use Atomic Energy 27, 68 (1958).
v. Ramm, C., G. B. Lucas, and H. V. Marshall, J.: The effect of maleic hydrazide on brown spot incidence of flue-cured tobacco. Tobacco Sei. 7, 100 (1962).
Reichard, T., and J. Schönbrunner: Vorläufiger Bericht über Versuche zur Verhinderung der Getreidelagerung. Bodenkunde 12, 29 (1961).
Robinson, A. G.: Effect of maleic hydrazide and other plant growth regulators on the pea aphid, Acyrthosiphon pisum (Harris), caged on broad bean, Vicia faba L. Can. Entomol. 92, 494 (1960).
Salisbury, F. B.: Growth regulators and flowering. 1. Survey methods. Plant Physiol. 32, 600 (1957).
Samborski, D. J., and M. Shaw: The physiology of host-parasite relations. The effect of maleic hydrazide and indoleacetic acid on the rust resistance of Khapli and Little Club wheat. Can. J. Bot. 35, 449 (1957).
Samborski, D. J., C. Person, and F. R. Forsyth: Differential effects of maleic hydrazide on the growth of leaf and stem rusts of wheat. Can. J. Botan. 38, 1 (1960).
Schoene, D. L., and O. L. Hoffmann: Maleic hydrazide, a unique growth regulant. Science 109, 588 (1949).
Shaw, M., D. J. Samborski, and A. Oaks: Some effects of indoleacetic acid and maleic hydrazide on the respiration and flowering of wheat. Can. J. Botan. 36, 233 (1958).
Shimomura, S.: Determination of maleic hydrazide. III. Conductometric titration method. J. Pharm. Soc. Japan 6, 589 (1958).
Sircar, S. M., and P. D. Ray: Studies on the physiology of rice. XV. Changes in the nitrogen metabolism of seeds during germination and their relation to the application of growth regulators. J. Expt. Botany 13, 61 (1962).
Sitterly, W. R., and J. R. Shay: Physiological factors affecting the onset of susceptibility of apple fruit to rotting by fungus pathogens. Phytopathol. 50, 91 (1960).
Smith, A. E., J. W. Zukel, G. M. Stone, and J. A. Riddell: Factors affecting the performance of maleic hydrazide. J. Agr. Food Chem. 7, 341 (1959).
Stewart, I., and C. D. Leonard: Increased winter hardiness in citrus from maleic hydrazide sprays. Proc. Amer. Soc. Hort. Sci. 75, 253 (1960).
Stoessl, A.: The photo-decomposition of maleic hydrazide. Presented annual meeting Chem. Inst, of Can., Toronto 1963.
Struckmeyer, B. E., and G. F. Beck: The effect of maleic hydrazide on the growth and flowering of Croft Easter lilies. Presented annual meeting Amer. Soc. Hort. Sci., Minneapolis 1951.
Suda, S.: Mode of action of maleic hydrazide on the growth of Escherichia coli and Avena coleoptile sections. Plant Cell Physiol. 1, 247 (1960).
Takeuchi, T., N. Yokouchi, and K. Onoda: Determination of maleic hydrazide. II. Polarographic determination of maleic hydrazide. Japan Analyst 5, 399 (1956).
Iaylorson, R., and L. G. Holm: Maleic hydrazide-auxin interactions in water uptake of potato discs. Plant Physiol. 36, 465 (1961).
Thompson, P. A.: Evidence for a factor which prevents the development of parthenocarpic fruit in the strawberry. J. Expt. Botany 12, 199 (1961).
Thompson, P. A. Reversal of photoperiodic induction of strawberries with maleic hydrazide. Nature 200, 146 (1963).
Towers, G. H. M., A. Hutchinson, and W. A. Andreae: Formation of a glycoside of maleic hydrazide in plants. Nature 181, 1535 (1958).
Tso, T. C., and R. N. Jeffrey: Effects of certain growth regulators on Nicotiana plants. Tobacco Sci. 5, 132 (1961).
United States Department of Agriculture: Research findings on the effects of maleic hydrazide on the suitability of tobacco for cigarette manufacture. Mimeo. 1961.
Vasil, I. K.: Effect of kinetin and gibberellic acid on excised anthers of Allium cepa. Phytomorphol. 7, 138 (1957).
Vickery, L. S.: Some effects of maleic hydrazide on flue-cured tobacco quality. Tobacco Sci. 3, 79 (1959).
Watt, G. W., and J. D. Chrisp: A spectrophotometric method for the determination of hydrazine. Anal. Chem. 24, 2006 (1952).
Waygood, E. R., A. Oaks, and G. A. Maclachlan: The enzymatically catalyzed oxidation of indoleacetic acid. Can. J. Bot. 34, 905 (1956).
Weller, L. E., C. D. Ball, and H. M. Sell: Studies of maleic hydrazide interactions with thiol compounds. Plant Physiol. 32, 146 (1957).
Wittwer, S. H., and I. G. Hillyer: Chemical induction of male sterility in cucurbits. Science 120, 893 (1954).
Wood, P. R.: Determination of maleic hydrazide residues in plant and animal tissue. Anal. Chem. 25, 1879 (1953).
Zukel, J. W.: A literature summary on maleic hydrazide 1949—1957. United States Rubber Company, Naugatuck, C.nn. 1957.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1964 Springer-Verlag Berlin · Göttingen · Heidelberg
About this paper
Cite this paper
Hoffman, I., Parups, E.V. (1964). Mode of action of maleic hydrazide in relation to residues in crops and soils. In: Gunther, F.A. (eds) Residue Reviews/Rückstands-Berichte. Reviews of Environmental Contamination and Toxicology, vol 7. Springer, New York, NY. https://doi.org/10.1007/978-1-4615-8389-9_6
Download citation
DOI: https://doi.org/10.1007/978-1-4615-8389-9_6
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4615-8391-2
Online ISBN: 978-1-4615-8389-9
eBook Packages: Springer Book Archive