Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1987-09-03
1989-02-21
Springer, David B.
Chemistry: fertilizers
Processes and products
Forms or conditioning
548494, A01N 4338, C07D20918
Patent
active
048061433
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to indoleacetic acid derivatives and application thereof as plant growth regulators.
BACKGROUND ART
Conventional indole-3-acetic acid (IAA) and derivatives thereof (methyl indole-3-acetate, indole-3-acetamide, etc.) are disadvantageous in that the carbon atoms at the 2- and 3-positions of indole ring are highly reactive, so that in living plants, these compounds are oxidized, are liable to be decomposed, and disappear in the living plants before they can exhibit their plant-growing action sufficiently.
In addition, 4,7-dichloroindole-3-acetic acid, 5,7-dichloroindole-3-acetic acid, etc. are known in Planta 140, 89 (1978). Therein, it is described that dichloroindole-3-acetic acid above has anti-auxin action, but there is given no description of its ability to promote plant growth.
DISCLOSURE OF THE INVENTION
The present inventor has found that compounds represented by the formula: ##STR2## (wherein each of X.sub.1, X.sub.2 and X.sub.3 is a hydrogen or chlorine atom; X.sub.2 is a chlorine atom and X.sub.3 a hydrogen atom in the case where X.sub.1 is a hydrogen atom; X.sub.2 is a hydrogen atom and X.sub.3 a chlorine atom or a hydrogen atom in the case where X.sub.1 is a chlorine atom; and R.sub.1 is a hydrogen atom, an alkali metal atom, or a lower alkyl group) are stable in living plants and excellent in plant growth regulating actions, for example, fruiting, fruit-thinning effects and sugar-increasing action, rooting, crop increasing action, wound-healing tissue promoting action in grafted trees, etc.
It cannot be expected at all from the above-mentioned known analogous compounds that although 4,7-dichloroindole-3-acetic acid and 5,7-dichloroindole-3-acetic acid in Planta 140, 89 (1978) above have anti-auxin action on plants, the dichloroindole-3-acetic acid derivatives and trichloroindole-3-acetic acid derivatives represented by the formula (1) of this invention have inverse physiological activities such as rooting effect.
BEST MODE FOR CONDUCTING THE INVENTION
The indoleacetic acid derivative of the formula (1) can be produced, for example, in the following manner.
First, a compound represented by the formula: ##STR3## (wherein X.sub.1, X.sub.2 and X.sub.3 have the same meanings as defined above) and a compound represented by the formula: ##STR4## (wherein Y is a cyano group, a carboxyl group or a ##STR5## group, R.sub.3 is a lower alkyl group, and R.sub.2 is a methyl group or an ethyl group) are subjected to condensation and ring closure in the presence of a condensation catalyst to obtain a compound represented by the formula: ##STR6## (wherein each of X.sub.1, X.sub.2 X.sub.3, Y and R.sub.2 have the same meanings as defined above).
Here, the condensation catalyst includes zinc chloride, hydrochloric acid gas-acetic acid, BF.sub.3 -acetic acid, sulfuric acid-acetic acid, hydrochloric acid-acetic acid, etc., though zinc chloride is preferred. As to the temperature at condensation and ring closure reaction, the reaction is carried out generally at 80.degree. to 200.degree. C., preferably at 100.degree. to 160.degree. C. Although in the above reaction, the compound of the formula (3) can be used as a solvent for reaction, it is also possible to use inert solvents such as hexane, octane and the like which do not react directly with the compound of the formula (3).
In carrying out the above reaction, the compound of the formula (3) and the condensation catalyst are used preferably in amounts in the ranges from 1.1 to 2 moles and 0.5 to 2 moles, respectively, per mole of the compound of the formula (2).
In this invention, the compounds of the formula (2) and the formula (3) are first reacted with each other in the above molar ratio preferably in the presence of an acid catalyst (e.g., camphorsulfonic acid, P-toluene-sulfonic acid, etc.) in a mixed solvent of an inert sovlent (e.g., benzene, toluene, xylene, hexane, etc.) and water (preferably, water: inert solvent=1:3 to 1:5 by volume), whereby there is isolated a hydrazone compound of the formula: ##STR7## (w
REFERENCES:
patent: 2701251 (1955-02-01), Fox et al.
Chemical Abstracts, vol. 75, No. 34996, p. 428, 1970.
Chemical Abstracts, vol. 103, No. 157620v, p. 437, 1985.
Zazimalova et al., Biologia Plantarum, vol. 27, pp. 114-118, 1985, "Auxin-Binding Site in Wheat Shoots: Interactions Between Indol-3-ylacetic Acid and Its Halogenated Derivatives".
Bruce J. Baldi, Janet Pernise Slovin and Jerry D. Cohen, "Synthesis of .sup.14 C-Labeled Halogen Substituted Indole-3-Acetic Acids", J. of Labeled Compounds and Radiopharmaceutical, vol. XXII, No. 3, pp. 279-285.
Hoffman, et al., "Auxin-Like Activity of Systematically Substituted Indoleacetic Acid", Journal Paper No. J-2035 of the Iowa Agricultural Experiment Station, Project 1110, and Project 1139, pp. 437-441.
Bottger, et al. "Growth of Avena coleoptiles and pH Drop of Protoplast Suspensions Induced by Chlorinated Indoleacetic Acids", Planta 140, pp. 89-92 (1978).
Futatsuya Fumio
Katayama Masato
Marumo Shingo
Saito Mikio
Nippon Kayaku Kabushiki Kaisha
Springer David B.
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