JPS6140201B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a plant growth regulator containing a compound represented by the following general formula [] or its acid addition compound as a main component. However, in the formula, R represents any one of the substituents represented by the following (1) to (4). (1) Amino. (2) Lower alkylcarbonyl. (3) Alkyl having all of the following characteristics (a) to (c). (a) The number of carbon atoms is 1 to 21. (b) Consisting of a chain or ring. (c) Substituted with one or more of the substituents represented by ~ below, or unsubstituted. However, the alkyl in ~ means only lower alkyl. Phenyl substituted with halogen or unsubstituted. Phenyloxy substituted with one or more of the following substituents or unsubstituted. Halogen, alkyl, hydroxy, alkyloxy, phenylalkyloxy. Hydroxy. Alkyloxy. Alkyloxyalkyl. Hydroxyalkylamino. N-alkylcarbonyl-N-phenylamino. Unsubstituted or N-alkyl substituted carbamoyl. Carboxyl that may form salts with alkali metals. Alkyloxycarbonyl. Hydroxyalkyloxycarbonyl. Unsubstituted or phenyl-substituted merkabuto.

【formula】

[Formula] (4) An alkenyl having all of the characteristics of (a) to (c) below. (a) The number of carbon atoms is 1 to 15. (b) Consisting of a chain or ring. (c) Substituted with one or more of the substituents represented by ~ below, or unsubstituted. However, the alkyl in ~ means only lower alkyl. Phenyl substituted with one or more of the following substituents or unsubstituted. Halogen, alkyl, hydroxy, alkyloxy, alkyloxyalkyloxy, alkyloxyalkyloxyalkyloxy, methylenedioxy, carboxy, alkyloxycarbonyl, cyano,
Carbamoyl, halogenalkyl, phenyloxy, alkylamino.

[Formula] Among the compounds represented by the general formula [], R
We have already filed a patent application for a plant growth regulator whose main component is a compound in which is hydrogen or a lower alkyl group having 1 to 4 carbon atoms. However, as a result of a series of detailed studies on this series of compounds, a compound was discovered that exhibited even more powerful effects than the above-mentioned compounds, and the present invention was completed. In addition,
It has already been shown that [] can be easily produced by the method described in Japanese Patent Application No. 11600/1983. [ ] generally exhibits a plant growth promoting effect at low concentrations, and exhibits a growth inhibiting effect at high concentrations. [ ] also exhibits a rooting promoting effect within an appropriate concentration range. As described above, the compound exhibits pleiotropic actions and is expected to find wide application as a plant growth regulator. Specific examples of the compound represented by the general formula [] used in the present invention are shown in Table 1.

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[Table] Using the compounds shown in Table 1, the plant growth inhibiting and plant growth promoting effects of the compounds used in the present invention will be described in detail below. 1 Plant Growth Inhibitory Effect The growth inhibitory effect of the compounds shown in Table 1 on various plants was investigated. The results are shown in Tables 2 and 3.
It is shown in Table and Table 4.

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[Table] As seen in Table 2, most of the compounds shown in Table 1 significantly inhibited the elongation of primary roots of rice. Also, as shown in Table 3,
[ ] significantly suppressed the elongation of roots and aerial parts of not only rice but also peas, radish, lettuce, carrots, cucumbers, onions, etc.
[ ] also significantly inhibited the proliferation of callus, as seen in Table 3. By utilizing this growth-inhibiting effect of [], it is possible to produce a plant dwarfing agent containing [] as a main component. The dwarfing agent produced in this way can be applied to prevent the lodging of rice and wheat, and to the production of potted plants such as potted mums and boinsettia. Furthermore, many dwarfing agents are also used as cut flower preservatives, and the dwarfing agent of the present invention can also be used as a cut flower preservative. When treated with [ ] at high concentrations, root elongation and growth are completely suppressed. For example, compound 55 at 10 μM
When rice seeds are treated at higher concentrations, no rooting is observed from the seeds. By utilizing these properties of [], it is possible to produce herbicides. The plant growth inhibitory effect of [] is due to the tertiary
As seen in the results in the table, there are significant differences depending on the plant species. That is, the growth inhibitory effect of [] shows plant species selectivity. [ ] can therefore be applied as a selective herbicide. Furthermore, by utilizing the growth inhibiting effect of [], a germination inhibitor can be produced. The germination inhibitor thus produced inhibits the germination of potatoes and onions, allowing them to be stored for long periods of time. 2 Plant Growth Promoting Effect [] exhibits a growth inhibiting effect and, at low concentrations, a growth promoting effect. The growth promoting effect of the compounds shown in Table 1 on plants was investigated. The results are shown in Tables 5 and 6.

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[Table] As seen in Table 5, most of the compounds shown in Table 1 significantly promoted elongation of the second leaf sheath of rice. Also, as shown in Table 6,
[ ] not only shows a growth-promoting effect on the above-ground parts of rice, but also on primary roots of rice, above-ground parts of radish,
It also showed a growth-promoting effect on sections of coleoptile coleoptiles. By utilizing the growth promoting effect of [] on plants, a plant growth promoter containing [] as a main component can be produced. The plant growth promoter thus produced can be applied as a yield increaser for edible crops such as vegetables and rice grains, fruits, mulberry leaves, medicinal plants, and the like. In addition, many plant growth promoters are also used as freshness-preserving agents, fruit set promoters, parthenocarpy inducers, and breakout inducers. It can be applied as a freshness-preserving agent for fresh vegetables and fruits, as a fruit set promoter for fruit trees, as a parthenocarpy inducer for grapes, etc., and as an agent for inducing dormancy break for gladiolus bulbs, etc. 3. Rooting promoting effect [] exhibits a rooting promoting effect as well as a plant growth promoting effect. The rooting promoting effects of the compounds shown in Table 1 on plants were investigated. The results are shown in Tables 7 and 8.

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[Table] As seen in Table 7, most of the compounds shown in Table 1 significantly promoted rooting of adzuki bean epicotyl sections. Furthermore, as shown in Table 8, [ ] not only showed a rooting promoting effect on adzuki bean epicotyl sections, but also showed a rooting promoting effect on germinated rice seeds. By utilizing these properties of [], [] can be used as a rooting promoter for plant "cuttings" and the like. It can also be applied as a rooting promoter for "transplanting" plants, an adhesion promoter for "splicing", etc. Examples relating to the production of the compounds listed in Table 1 are shown below. 1 Synthesis of compound 42 Dissolve 3.2 g of moranoline in 100 ml of DMF, add 7.9 g of cinnamyl bromide and anhydrous potassium carbonate.
Add 8.0g and stir at 70-80℃ for 4 hours. After cooling, dilute with 400 ml of water, acidify with hydrochloric acid, and wash with benzene. The benzene layer is extracted with 1% aqueous hydrochloric acid, and the aqueous layers are combined, made into ammonia alkali, and extracted with n-butanol. The extract is washed with water, dried under reduced pressure, and the remaining crystals are recrystallized from methanol. Yield 2.8
g. Melting point: 167-168°C, [α] ²⁴ _D = -49.0° (methanol). Hydrochloride: Recrystallized from methanol, melting point 216-218
℃. [α] ²⁴ _D = -15.0° (water). 2 Synthesis of compound 62 Dissolve 0.82 g of moranoline in 2 ml of water, dilute with 6 ml of ethanol, and dissolve phenylpropyl bromide.
80-90 by adding 1.3g and 0.38g potassium carbonate
Heat and stir at ° for 6 hours. After cooling, dilute with 100 ml of water, wash with ether, and pass through a column of ion exchange resin Amberlite IR-120B (H). The adsorbed material is eluted with 1% aqueous ammonia, evaporated to dryness under reduced pressure, the residue is dissolved in isopropyl alcohol, 0.24 g of p-toluenesulfonic acid is added, and the precipitated crystals are collected. If this is reconstituted from alcohol, the target product is obtained as p-toluenesulfonate. Yield 0.51g. Melting point: 219-221°C, [α] ²⁴ _D = -3.5° (water). As is clear from the above, the compound used in the present invention has excellent growth-inhibiting, growth-promoting, and rooting-promoting effects, and is highly water-soluble, so it can be made into an aqueous solution by a commonly used method. Accordingly, a plant growth regulator can be easily produced. Examples of the present invention will be described below. From the useful action and water solubility of the compounds used in the present invention, it is clear that the present invention includes herbicides, dwarfing agents, growth promoters, rooting promoters, etc. as plant growth regulators. It is not limited to the examples. Example Compound 129 was used to prepare a 1 mM aqueous solution. When this was removed from the field at the time of planting cucumber seedlings, the growth of weeds was significantly suppressed compared to the untreated plot. On the other hand, there was almost no effect on the growth of cucumber.

Claims (1)

[Scope of Claims] 1. A plant growth regulator comprising a compound represented by the following general formula [] or its acid addition compound as a main component. However, in the formula, R represents any one of the substituents represented by the following (1) to (4). (1) Amino. (2) Lower alkylcarbonyl. (3) Alkyl having all of the following characteristics (a) to (c). (a) The number of carbon atoms is 1 to 21. (b) Consisting of a chain or ring. (c) Substituted with one or more of the substituents represented by ~ below, or unsubstituted. However, the alkyl in ~ means only lower alkyl. Phenyl substituted with halogen or unsubstituted. Phenyloxy substituted with one or more of the following substituents or unsubstituted. Halogen, alkyl, hydroxy, alkyloxy, phenylalkyloxy. Hydroxy. Alkyloxy. Alkyloxyalkyl. Hydroxyalkylamino. N-alkylcarbonyl-N-phenylamino. Unsubstituted or N-alkyl substituted carbamoyl. Carboxyl that may form salts with alkali metals. Alkyloxycarbonyl. Hydroxyalkyloxycarbonyl. Unsubstituted or phenyl substituted mercapto. [Formula] (4) An alkenyl having all of the characteristics of (a) to (c) below. (a) The number of carbon atoms is 1 to 15. (b) Consisting of a chain or ring. (c) Substituted with one or more of the substituents represented by ~ below, or unsubstituted. However, the alkyl in ~ means only lower alkyl. Phenyl substituted with one or more of the following substituents or unsubstituted. Halogen, alkyl, hydroxy, alkyloxy, alkyloxyalkyloxy, alkyloxyalkyloxyalkyloxy, methylenedioxy, carboxy, alkyloxycarbonyl, cyano,
Carbamoyl, halogenoalkyl, phenyloxy, alkylamino. [Formula] 2. The plant growth regulator according to claim 1, wherein the plant growth regulator is a dwarfing agent. 3. The plant growth regulator according to claim 1, wherein the plant growth regulator is a plant growth promoter. 4. The plant growth regulator according to claim 1, wherein the plant growth regulator is a rooting promoter.