JPS61152604A - Plant growth regulator - Google Patents

Abstract

PURPOSE:The titled regulator to control effectively germination of side buds of tobacco without exerting a bad influence on growth and yield of tobacco, having inhibitory action on buds of woody plants, comprising an N-substituted alanine derivative and an inert carrier. CONSTITUTION:A plane growth regulator comprising an N-substituted alanine derivative shown by the formula I (X is halogen, or trifluoromethyl; R is H, 1-8C alkyl, 2-4C alkenyl, metallic atom, or amine forming residue; n is 0, 1, or 2) and an inert carrier. When it is used, an emulsion form is preferable, for example, preferably the regulator is blended with a solvent such as benzene, etc., and various surface active agents, etc., diluted with water into about 1,000-5,000ppm concentratoin and used. The compound shown by the formula I, for example, is obtained by reacting a compound shown by the formula II with a compound shown by the formula III (Hal is halogen; R<1> is lower alkyl), to give a corresponding compound shown by the formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a plant growth regulator containing an N-substituted alanine derivative as an active ingredient, and more specifically.

General formula (1): (in the formula, or a halogen atom or a trifluoromethyl group, R is a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, an alkyl group having 2 to 4 carbon atoms, an alkali Represents a metal atom or an amine-forming residue, and n represents an integer of 0, 1, or 2.However, when n is 2, X may be the same or different.) The present invention relates to a plant growth regulator containing one or more N-substituted alanine derivatives as an active ingredient.

The N-substituted aranino derivative of the present invention has optical isomers, and these isomers are also included in the present invention.

In the compound of the present invention represented by the above general formula (I),
When X is a halogen atom 1 For example, a fluorine atom, a chlorine atom,
Examples include bromine and iodine atoms.

When R is a lower alkyl group, methyl group, ethyl group e n
-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, etc.; alkali metal atoms include sodium atom, potassium atom, etc.; amine-forming residues include dimethylammonium group; , diethylammonium group, lJ ethylammonium group, and the like.

The compounds of the present invention include new compounds and known compounds, and the known compounds are useful as active ingredients of herbicides (see JP-A-52-15.821).
Although it is known.

It is completely unknown that it is useful as a plant growth regulator, particularly as a tobacco axillary bud inhibitor and a woody plant bud inhibitor.

Most of the compounds of the present invention are substances with strong auxin activity. Conventionally, when plants are treated with substances that have strong auxin activity, they often develop abnormal growth, strong erectile dysfunction, or killing effects. Therefore, it is commonly used as a herbicide to kill weeds.

The present inventors have found that among the 9 substances with strong auxin activity, they have the ability to suppress the sprouting of woody plants, and also have no practical adverse effects on the growth and yield of tobacco, and are effective in suppressing the development of axillary buds in tobacco. The present invention was completed by discovering a substance that can suppress the

Among the compounds of the present invention represented by the general formula (I).

Also, a fluorine atom, a chlorine atom or a trifluoromethyl group is preferable, and R is a methyl group.

:x-thyl group*n-propyl group, isopropyl group.

Butyl group, allyl group, etc. are desirable.

Next, one example of the method for producing the compound of the present invention is shown in the following reaction formula.

(II) (2) (Iv) (v) (V) (■) (In the reaction formula, X and n represent the same meanings as above.

Ha) is a halogen atom, and R1 is a lower alkyl group.

M represents an alkali metal atom; R2 and R5 each represent a lower alkyl group. ) In the reaction of (1), the compound represented by formula (9) and the compound represented by formula (2) are combined in an inert solvent such as acetonitrile in the presence of an acid acceptor such as anhydrous potassium carbonate. By heating under reflux, the compound (IV) of the present invention represented by formula (ff) can be easily obtained.

In reaction (2), the compound of the present invention represented by formula 6 (v) can be easily obtained by heating and hydrolyzing the compound represented by formula 9 (IV) with an aqueous alkali hydroxide solution.

In (3), a compound represented by formula (V) is used.

The compound of the present invention represented by formula 9 (b) can be easily obtained by acid precipitation with a mineral acid such as hydrochloric acid.

In the reaction of (4), to a compound represented by formula (9).

By adding various amines, for example, formula (b)
The compound of the present invention represented by can be easily obtained.

Next, the method for producing the compound of the present invention will be explained by giving a specific synthesis example.

Synthesis Example I Synthesis of N-(3-chloro-4-fluorophenyl)alanine ethyl ester (compound 11) 5-chloro-4-fluoroaniline 14.6f, ethyl α-bromopropionate in 50-acetonitrile Ester 12.1 f and anhydrous potassium carbonate &91 were added and heated under reflux for 24 hours. After the reaction, the title target compound 10. is obtained by filtration, concentration of liquid F under reduced pressure, and distillation. Of
I got it. Boiling point: 97-100° C. 1015 關Go 2 The compound obtained above (Compound 11) was heated and hydrolyzed with an aqueous sodium hydroxide solution to obtain the sodium carboxylate salt of the target compound (Compound 13).

Subsequently, by acid precipitating the sodium salt with hydrochloric acid,
The target compound carboxylic acid (Compound Shop 12) was obtained.

Next, various compounds of the present invention were synthesized in the same manner as in Synthesis Example 1. All six compounds including those synthesized in Synthesis Example 1 are shown in Table 1.

In addition, compound A is referred to in the following formulation examples and test examples.

Table 1 Next 0 When the compound of the present invention is used as a tobacco axillary bud inhibitor or a woody plant bud inhibitor, the formulation form is not particularly limited, but an emulsion form is preferable. . In the form of an emulsion, the compound of the present invention may be mixed with various carriers, such as solvents such as benzene, toluene, xylene, and various surfactants.

When using it, it may be used as is, but it is preferable to dilute it with water to a predetermined concentration.

The fecal concentration of the compound of the present invention is [Purpose of Use].

It varies depending on the type of tobacco or woody plant, the period of use, and other conditions, but generally it is 100-i.
o, o o o ppm is desirable, preferably to
It is appropriate to use it at a concentration of about 0.00 to 0.000 ppm.

Next, examples of formulations are shown below, but the invention is not limited to these. In addition, in the following formulation examples, "parts" mean parts by weight.

Reduced emulsion r Compound A of the present invention 11------°°°----
−°−°−20 parts (mixture of nonionic and anionic surfactants).

Toho Chemical Co., Ltd. (trade name) The above ingredients are mixed uniformly to form an emulsion. When used, it is diluted 20 to 2,000 times with water.

(A mixture of nonionic surfactant and anionic surfactant.

Toho Chemical Co., Ltd. (trade name) The above ingredients are mixed uniformly to form an emulsion. For toilet use, dilute 25 to 2,500 times with water.

The content of the compound of the present invention in the emulsion is not particularly limited, but is preferably 1 to 70 weight (possibly @, but preferably 5 to 50 weight).

Next, a reference example in which the auxin effect on planting conditions of the compounds of the present invention was tested, as well as a test example for suppressing new shoots of woody plants, and a test example for suppressing axillary buds of tobacco will be specifically explained.

Reference Example 1 Auxin Activity Certification Test In a Petri dish with a diameter of 71 mm, 10 rice seeds and 1 chemical solution of each test compound at a predetermined concentration were placed.
I added 0ad. The average plant length was measured after germination and growth for 10 days at 25°C in the dark, and 10
A comparison value was calculated when the value was set to 0. The results are shown in Table 2.

The smaller this contrast value is, the stronger the auxin activity is.
(trade name) and NAA (common name) were also tested as control compounds.

The active ingredient compound name of 2.4-D is 2.4-dichlorophenoxyacetic acid, abbreviated as control compound A in the following reference examples and test examples, and the active ingredient compound name of NAA is α-naphthalene acetic acid, as follows: υ Abbreviated as Control Compound B in Reference Examples and Test Examples.

Table 2 As is clear from Table 2, one of the compounds of the present invention has strong auxin activity.

Reference Example 2 Spraying test on tomato seedlings When tomato seedlings reached the four-leaf stage, a chemical solution of each test compound at a predetermined concentration was uniformly sprayed on the collection, and the degree of malformation was investigated 5 days after the spraying. . The results are shown in Table 3. However, the ◎ mark indicates that the odd shape is large, and the Δ mark indicates that the odd shape is small or none.

Table 5 As is clear from Table 5, the compound of the present invention does not contain 2,4-D (control compound A) or NAA as shown in Reference Example 1.
Although it has a strong auxin activity comparable to (comparison compound B), its potency is much lower.

Next, practical tests were conducted on the nine compounds of the present invention as plant growth regulators (woody plants sprout suppression test and tobacco side bud suppression test).

In woody plants, suppression of new shoots may have important significance1
For example, trees in green areas are pruned once to several times a year to maintain their shape and beauty. In addition, in fruit trees, excessive elongation of new branches may be undesirable, and the compounds of the present invention can effectively suppress the generation of new shoots in such cases.

Furthermore, suppression of tobacco axillary buds is extremely important. In order to maintain good quality of tobacco leaves, core pruning is generally performed at the beginning of flowering. However, if you leave it as it is after removing the core, side buds will develop.

Unable to maintain good quality of tobacco leaves.

It is extremely important to suppress these axillary buds, and the compounds of the present invention can effectively suppress axillary buds in such cases. Next, a specific explanation will be given by giving a test example.

Test Example 1 Sprout Suppressing Power Test on Woody Plants A chemical solution containing a prescribed concentration of each test compound was uniformly sprayed on tangerine trees (about 50 cm in height) planted individually in 5-inch pots before germination in spring. Two months after the spraying, the degree of emergence of new shoots and the degree of chemical damage were investigated, and the results are shown in Table 4.

Table 4 As is clear from Table 4, the compound of the present invention sufficiently inhibits the development of sprouts, and almost no phytotoxicity is observed.

Tobacco axillary bud suppression test Tobacco plants (variety: Hakuenshū) to be tested were pinched at the beginning of flowering, and the compound of the present invention in the form of an emulsion was diluted with water and a chemical solution of a predetermined concentration was uniformly sprayed on the pinched stems.

In the test, 10 plants were used in each treatment area. Two weeks after spraying, the average dry weight of axillary buds per tobacco was measured, and the presence or absence of chemical damage was also investigated.

Incidentally, it is known that 2.4-D and NAA are highly unstable and have no practical use. The results are shown in Table 5.

Table 5 As is clear from Table 5, the compound of the present invention effectively suppresses the amount of axillary buds, and no chemical damage is observed at all. Therefore, the compound of the present invention has sufficient practical utility as a cigarette smoke prevention agent.

Claims (8)

[Claims] (1) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, , represents an alkenyl group having 2 to 4 carbon atoms, an alkali metal atom, or an amine-forming residue, and n represents 0 or an integer of 1 to 2.However, when n is 2, X may be the same, or ) may be different.
- A plant growth regulator comprising a substituted alanine derivative and an inert carrier. (2) The plant growth regulator according to claim 1, wherein R represents a linear or branched alkyl group having 1 to 6 carbon atoms, and n is 2. (3) The plant growth regulator according to claim 1 or 2, which is a sprout inhibitor for woody plants. (4) Claim 1, which is a tobacco axillary bud inhibitor.
The plant growth regulator according to item 1 or 2. (5) The plant growth regulator according to claim 4, wherein the tobacco axillary bud inhibitor is in the form of an emulsion. (6) A method for suppressing side buds by applying an effective amount of the plant growth regulator according to claim 1 to the area around the pinched part of tobacco after the tobacco has been pinched. (7) A method for suppressing side buds by applying a solution of the plant growth regulator according to claim 1 in an active ingredient concentration of 1,000 to 5,000 ppm to the area around the pruned part of the tobacco after the tobacco is pruned. (8) General formula: ▲There are numerical formulas, chemical formulas, tables, etc.▼ (In the formula, R represents a straight chain or branched alkyl group having 1 to 8 carbon atoms.) N-substituted alanine derivative.