JPS6039258B2 - New phenoxyacetic acid ester - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel wastel useful for agriculture and horticulture, a method for producing the same, and its use as a plant growth regulator and a composition thereof.

The present inventors have discovered that 3-t-butylphenoxyacetic acid propyl ester (hereinafter referred to as compound (1)) represented by the formula has a plant growth regulating effect and can beneficially promote the growth of economically valuable plants. It has been found that it can be used as a plant growth regulator.

That is, when compound (1) is applied to the plant tissue of a growing or dormant plant, it is possible to improve, for example, the quality or yield of a crop, and the grower can conveniently control and control the growth process of the crop. It can also facilitate the handling of the crop, for example during harvest, especially mechanical handling. When compound (1) is applied to plants, plant growth is promoted or conversely suppressed depending on the rate of application and the growth period of the treated plant tissue. For example, when compound (1) is applied to plants, the following excellent plant growth regulating effects can be obtained. [a-
Increasing the yield of fruit from fruiting trees and shortening the growing season until harvest: [i] Fruits from fruiting trees, such as apples, pears, peaches, plums, citrus fruits (such as mandarin oranges, neafles, lemons, etc.), oil palm Increase the yield of etc.

In other words, when compound (1) is sprayed, the growth of the apical part of the trunk is suppressed without killing the growing point of the apical bud, thereby promoting the elongation (grathering) of the lateral branches of one-year-old seedlings, and the growth of the lateral branches and trunk of young trees. The generation of lateral branches in the upper part of the tree is actively promoted from the spraying point of compound (1) (usually sprayed between 20 and 50 cm from the apex of the tree) while maintaining a preferable wide angle between the tree and the tree. , and trees that are 2 to 3 years old after being transplanted to the orchard are exposed to compounds (1
), the generation of secondary side branches is promoted.

As a result, the tree shape is improved to a desirable shape and the yield of fruit is increased. {ii) Regarding the young seedlings that have been treated with the above treatment, in the case of fruit trees such as apples, pears, peach trees, plums, etc., the fruit should be harvested after the seedlings are transplanted to the orchard. The growing period for apple trees, for example, is reduced from the usual two years to one year.

For the purpose of
It is preferable to apply it in the form of a composition such as a fogging agent containing 50 to 1500 ppm.

{b} Improving the tree shape of ornamental plants: Plants for pot tanks [for example, Cornus species (Doo ood), etc.], ornamental trees [for example, Acer species (sycamore maple)] ), etc.], and in the case of trees, the oak shape is improved to a desirable shape by encouraging the elongation of lateral branches.

For this purpose, it is preferred to apply the compound (1) in the form of a composition such as a spray agent containing 750 to 400 pm. (cl. Fruit quality improvement: Flower thinning or fruit thinning is performed by spraying the compound (1) at the time of full bloom of flowers, the time of fruit set, or the intermediate stage of fruit development. This improves the quality of fruits, especially apples and grapes. is improved.

For this purpose, compound (1) is added at 250 to 1500
It is preferable to apply it in the form of a composition such as a spray containing ppm. 'd} Increasing the yield of field crops: Application to increase the yield of field crops such as soybeans, broad beans, other pulses, peanuts, oilseed rape and sunflowers. increase

The preferred application time is the flowering period (for example, the flowering period of cotton). For this purpose, compound (1) is mixed with 0.56 to 2
．． Preferably, it is applied at a rate of 24k9/ha. {e'Chemical fortification of young plants: Cultivated crops that need to be established at a young age, such as tea (
By spraying the compound (1) on young plants of tea, black tea, etc., the growth of lateral branches is promoted, and the effect of chemically energizing the young plants can be obtained.

For this purpose, compound (1) is added at 750 to 3000
Preferably, the application is in the form of a composition such as a spray containing ppm.

0 Promotion of defoliation of young trees: [i) Promotion of young trees such as ornamental shrubs, Japanese trees (e.g., roses, Quercus mbra, etc.), fruit trees (e.g., apples, etc.), hedge trees, etc. Spraying compound (1) at the end of the growing season (season) promotes defoliation, facilitates their transplantation, and also controls diseases.

'ii' By spraying compound (1) on shrubs such as jasmine before flowering, the number of flowers per branch in the following year is increased.

For the purposes of {o'i' and {ii} above, it is preferable to spray compound (1) in the form of a composition such as a spray containing 1000 to 1000 pm.

(g) Increasing the number and weight of underground tubers: increasing the number and harvested weight of tubers of legumes (eg sweet potatoes, potatoes, etc.).

For this purpose, compound (1) is added at 1000 to 300
It is preferable to apply it in the form of a composition such as a mist containing Cape PM. (h) Increasing the yield of hollyhocks, etc.: Instead of the method of pinching off the apical buds of Brussels sprouts, the elongation of the apical buds is suppressed by spraying compound (1) at the time when the apical buds are formed. The yield is improved and there is less wastage of the crop.

For this purpose, compound (1) is added at 4000 to 600
It is preferable to spray it in the form of a composition such as a spray agent containing other PM. (i) Suppression of lateral branch growth: Undesirable lateral branch growth, for example the growth of tomato lateral branches, is suppressed.

For this purpose, it is preferred to apply compound (1) in the form of a composition such as a spray containing 3000 ppm. (i) Increasing the crop yield of monocots: In monocot crops (e.g. wheat, barley, rice, etc.), increasing the number of tillers on their stems and reducing spring flowering and steadfastness. By reducing the number of ineffective Renatsuho stocks, the amount of monkeys harvested is increased.

For this purpose, compound (1) is added at 200 to 2000
It is preferable to apply it in the form of a composition such as a spray containing ppm. 3-t- when applied to developing plant tissue
The excellent growth-regulating effect of phthylphenoxyacetic acid propyl ester is demonstrated by the following representative experiment.

Experimental Example 1 3-t-Butylphenoxyacetic acid propyl ester 85 obtained by diluting the liquid composition described in Example 5 below with water
A spray solution containing Masu pm was sprayed onto fruit trees from a height of 70 skins in early summer.

The effect of producing lateral branches on fruit trees was compared with that of untreated control fruit trees*
Then, an inspection was conducted in early spring of the following year. The results are shown in Table 1.
In addition, the number of side branches in the table is shown as the average value of the seven treated fruit trees.
Table 1 The results show that application of 3-t-butylphenoxyacetic acid propyl ester to apple and pear trees increases the production of side shoots.

Experimental Example 2 A spray solution containing 900 ppm of propylester 3-t-butylphenoxyacetate obtained by diluting the liquid composition described in Example 5 below with water was applied to apple seedlings (Bramley variety) in early summer. It became foggy and dawned again in early summer two years later.

The average number of inflorescences per tree was examined in the spring following the second treatment.

As a control, a tree whose branches had been determined using a conventional method was also examined in the same manner. The results are shown in Table 2. Second
As is clear from the above results, when 3-tert-butylphenoxyacetic acid propyl ester is applied to apple trees that are 2 to 3 years old, the trees are more effective than those that have been determined using conventional methods. The shape of the plant has been improved, and an increase in the number of lateral branches and inflorescences has been observed.

Experimental Example 3 The liquid composition of Example 5 described later was diluted with water,
This was sprayed on cotton for 2 to 4 weeks after full bloom at a ratio of 0.56 x 9, 1.12 k9 and 2.24 k9/hectare of 3-t-butylphenoxyacetic acid propyl ester.

At harvest, the increase in cotton yield per hectare was tested and compared to untreated cotton. The results are shown in Table 3. As is clear from the above results in Table 3, the cotton yield increased by spraying 3-t-butylphenoxyacetic acid propyl ester.

According to the present invention, the compound of formula (1) is represented by the formula: It can be obtained by reacting a compound with propanol.

The reaction between the compound of formula (0) (in the formula, x is a hydroxyl group) and propanol can be carried out in the presence of an acidic catalyst (for example, hydrogen chloride gas, sulfuric acid or p-toluenesulfonic acid), if desired.
It is carried out under substantially anhydrous conditions in the presence of an inert organic solvent (e.g. toluene) or with an excess of propanol as solvent, under heat (e.g. 80-120 qo), preferably at the reflux temperature of the reaction mixture. It will be done.

The reaction of the compound of formula (D) (where x is halogen) with propanol is carried out optionally in the presence of an acid binder (such as triethylamine or pyridine) and optionally in an inert organic solvent (such as carbon tetrachloride, chloroform or toluene). ) at room temperature to heating (e.g. room temperature to 120°C)
), preferably at the reflux temperature of the reaction mixture.

The transesterification reaction between the compound of formula (0) (in the formula, x is alkoxy other than propoxy) and propanol is carried out in the presence of an acidic catalyst (for example, hydrogen chloride gas, sulfuric acid or p-toluenesulfonic acid), optionally with an inert catalyst. It is carried out in an organic solvent or an excess of propanol under substantially anhydrous conditions and under heat (for example from 60 to 120 qO), preferably at the reflux temperature of the reaction mixture. In other states, equation (1)
A compound of the formula: (wherein M means an alkali metal, such as sodium or potassium) is a compound of the formula: YCH2COOR(N) (wherein, Y is a halogen, such as chlorine, and R is a carbon number 1 to 6 alkyl), and then, when the reactant (W) is a compound other than R=propyl, the compound is further subjected to the transesterification reaction described above. Ru.

The reaction between the compound of formula (m) and the compound of formula (W) is
It is carried out in an anhydrous inert organic solvent (eg dimethylformamide or propanol) at 0-100 qC. The compound of formula (0) (wherein X is a hydroxyl group) is produced by applying a known method for producing phenoxyacetic acid.

The compound of formula (0) (in the formula, X is a halogen) is produced using the compound of formula (b) (in the formula, x is a hydroxyl group) by applying a known method for obtaining an acid halide from a carboxylic acid. This compound may be used without purification. The compound of formula (0) (
In the formula, x is alkoxy other than propoxy) is produced by applying a known method for producing a carboxylic acid ester, for example, the method used for producing the compound of formula (1) above.

The compound of formula (m) is produced using a known method for obtaining an alkali metal salt thereof from 3-t-butylphenol.

The compound of formula (N) is produced by applying a known method for producing a monohalogen-substituted acetate.

As used herein, "known methods" refers to methods that are commonly used or described in the chemical literature. Another aspect of the present invention provides a method for regulating the growth of plants as described above, which comprises administering an effective amount of the compound of formula (1) to actively growing or dormant plant textiles. It is done by applying.

For this purpose, the compound may be used alone or in the form of a composition for regulating plant growth as described below (for example, one or two compounds).
(mixed with more than one compatible diluent or carrier). A preferred method of application is to apply in-floor fog (ultra-low volume fog) directly to one-year-old fruit tree seedlings.
esprays] or foamy rumors.

Also spray on the hollyhocks or stems of growing plants. A method of particular interest involves applying a compound of formula (1) to one-year-old fruit tree seedlings, especially apple and pear trees, preferably from 0.075% by weight (750 ppm) to 0.15% by weight (150 ppm). pm
) It is sprayed in the form of a composition such as a spray containing it in a range of 20 to 50 arcs from the tips of growing trees, and in the case of fog other than the Akebono fog method, for example, 50 liters or less / hectare. A method of promoting lateral branching of fruit trees by applying a spray solution with a rainfall of
A compound of formula (1) is applied to a 3-year-old fruit tree, preferably at 0.1
25% by weight (1250ppm) to 0.15% by weight (15% by weight)
This is a method of promoting the generation of secondary branches by spraying in the form of a composition such as a spray containing 0 pm). In another aspect of the present invention, the compound of the formula (1) is used as an active ingredient, and the compound of the formula (1) is used as an active ingredient;
1) of a suitable diluent or adjuvant compatible with the compound of 1).
Provided is a liquid composition for regulating plant growth that is mixed with a seed or two or more seeds.

The liquid composition according to the invention can be in the form of a solution, suspension or emulsion, and preferably contains wetting agents, dispersing agents, emulsifying agents and the like.

These solutions, suspensions and emulsions may contain aqueous or organic diluents such as acetophenone, cyclohexanone, isophorone, toluene, xylene, dimethylformamide, mineral, animal or vegetable oils, or mixtures thereof. They may be further blended with ionic or nonionic wetting agents, dispersants, emulsifiers, or mixtures thereof as described below. Solutions or emulsions containing the compound of formula (1) are optionally obtained by dissolving the active ingredient in an emulsifier or wetting agent or in an emulsifier- or wetting agent-containing solvent compatible with the active ingredient. It may be in the form of a self-emulsifying or self-dissolving concentrated liquid, and a composition that can be easily used can be prepared by simply adding water to this concentrated liquid. The wetting agents, dispersants and emulsifiers used are ionic or non-ionic, for example sulforicinoleates, quaternary ammonium derivatives, ethylene oxide condensates of nonyl- and/or octylphenols, and the addition of free hydroxyl groups with ethylene oxide. Examples include carboxylic acid esters of anhydrosorbitol made soluble by condensation and etherification, or mixtures thereof. The composition of the present invention has the formula (
Compositions capable of producing foam containing the compound of 1) are also included.

The composition of the present invention may contain other auxiliary compounds in addition to the compound of formula (1), and it may be formulated in such a way that the compound of formula (1) and the auxiliary compound are combined together, or It may also be in a form that is mixed in a tank.

Auxiliary compounds used include organic linesters,
For example, parathion (i.e., 0,0-jethyl○-
4-nitrophenyl phosphorothionate), malathion (i.e. S-[1,2-di(ethoxycarbonyl)
Ethyl〇,0-dimethylphosphorothiorothionate)
, vamidothione (i.e., ○,0-dimethyl S-[2
-(1-methylcarbamoylethylthio)ethyl) phosphorothionate), diazunone (i.e. 0,0-diethyl○-[2-isopropyl-6-methylpyrimidin-4-yl]phosphorothionate), monocrotophos (
That is, 0,0-dimethylcis-1-methyl-2-(
N-methylcarbamoyl)pinyl phosphate), dimethytoate (i.e. 0,○-dimethyl S-(N-methylcarbamoylmethyl)phosphorothiolothionate)
, fosualone (i.e., S-(6-chloro-2-oxobenzoxazolin-3-yl)methyl○,0-diethylphosphorothiothiolonate) and bromophosethyl (i.e., -dichlorophenyl)○,0-diethylphosphorothionate): Carbamates, such as carbaryl (i.e., 1-naphthyl N-methyl carbamate) and fortanate (i.e., 3-dimethylaminomethyleneiminophenyl N-methyl carbamate) ); natural or synthetic pyrethrins, such as bioallethrin; chlorinated hydrocarbons, such as DDT (i.e. 1,1,1-trichloro-2,
2-pis(P-chlorophenyl)ethane or its o-
or P'-isomer), BHC (i.e., isomeric mixture of 1,2,3,4,5,6-hexachlorocyclohexane), toxaphene [i.e., camphochlor (with 67-69% chlorine), acaricides, such as chinomethionate (i.e., 6-methyl-2,3
-quinoxaline diyl cyclic S,S-dithiocarbonate), dicofol (i.e., 2,2,2-trichloro-1
, 1-bis(p-chlorophenyl)ethanol) and tetradifone (i.e., 2,4,4,5-tetrachlorodiphenylsulfone), as well as synergistic methylenedioxyphenol derivatives such as pivero Nylptoxide (i.e., 5-[2-butoxyethoxy)ethoxymethyl]6-propyl-1,3-penzooxosol), Sesamex (i.e., 2-(3,4-methylenedioxyphenoxy)-3, 6,9
-trioxaundecane) and ○,0-dimethyl○-
Non-insecticidal compounds such as phenyl phosphorothioate, as well as copper sulfate, dinocap [i.e., 2,6-dinitro-
A mixture of 4-octylphenyl crotonate and 2,4-dinitro-6-octylphenyl crotonate (octyl also represents isomeric groups such as 1-methylheptyl, 1-ethylhexyl, 1-propylbentyl)], chloro xylenol (i.e. 4-chloro-3,5-xylenol), thiophanatomethyl (i.e. 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene), dichlorophene (i.e. bis(5-chloro-2 -hydroxyphenyl)methane) and cyram (i.e., tetramethylthiuram disulfide), Bacillus thuringiensis
thmingiensis agents (toxins and microbial agents)
and insect virus agents. Many auxiliary compounds are known in the art, and any of these known compounds that are compatible with the compound of formula (1) and the other composition components may be used.

The composition of the present invention contains 0.05 to 90% of the compound of formula (1).
(w/v) and, depending on the type of plant to be treated, is applied to the plants in such amount that, at the discretion of the farmer or other skilled worker, the desired effect can be achieved.

Next, a method for producing the compound of the present invention and a method for preparing a composition containing the same will be specifically explained using Examples.

Example 1 10.4 tons of 3-tert-butyl phenoxyacetic acid are heated to reflux in 80 g of propanol for 2 hours while passing a stream of hydrogen chloride gas through.

Excess propanol is distilled off and Zenizasa is purified by Jethy Lutheran 7.
Dissolve in 5'. The ethereal solution is washed successively with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate, filtered and evaporated to dryness. The oily residue is distilled to form a colorless oil with a boiling point of 179 to 180 qo/18 Hg.
-Add 8.5 g of t-butylphenoxyacetic acid propyl ester. Example 2 920 g of tert-butylphenoxyacetic acid is heated to reflux with 920 g of thionyl chloride for 2 hours.

Excess thionyl chloride is distilled off and further traces of thionyl chloride are removed by distillation in the presence of toluene (2 x 500). The 3-t-butylphenoxyacetyl chloride from this preparation is slowly added to 6.5 liters of refluxing propanol. After the addition is complete, the solution is heated to reflux for 2 hours. Excess propanol is removed under reduced pressure. The residue was distilled to form an almost colorless oil with a boiling point of 170°C/12 skin Hg.
68 evenings passed. Example 3 A solution of 12.1 parts of chloroacetic acid propyl ester dissolved in 10 parts of anhydrous dimethylformamide was dissolved in 3-t-butylphenol sodium salt (3-tert-butylphenol sodium salt).
10 parts of 3-t-butylphenol and 1 part of sodium hydride
．． (prepared from 50% of anhydrous dimethylformamide)
Add 10~15o0 to the solution dissolved in water.

The mixture was allowed to stand for 2 hours at room temperature and then evaporated to dryness. Dissolve the residue in a mixture of 100 M chloroform and 100 M water. The organic layer was separated, dried over magnesium sulfate, evaporated and distilled to a boiling point of 176-178q.
10.32% of 3-t-butylphenoxyacetic acid propyl ester is obtained as a colorless oil at 0/2 mercury. Example 43
-t-Butylphenoxyacetic acid methyl ester 27.92
(boiling point 161-1620/20 Yanagi Hg, prepared in the same manner as in Example 2 above using methanol instead of propanol) is dissolved in Propanol 45 skin.

From this solution, the propanol containing hydrogen chloride was distilled off, and the remaining liquid was dissolved in 75% of jetyl ether. The ethereal solution is washed successively with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate, evaporated and evaporated to dryness. The oily residue is distilled to a boiling point of 173~175o0/1
23% of 3-t-butylphenoxyacetic acid propyl ester was obtained as a colorless oil with 5% Hg. Example 5 The following components are mixed to obtain a liquid composition in the form of a concentrated liquid.

% (W/V) 3-T-Butyl phenoxyacetic acid propyl ester 90 Duoteric M old 1
5 Duoterik M old 2
5 Example 6 Below: The ingredients are mixed to obtain a liquid composition in the form of a concentrated liquid.

% (W/V) 3-t-Butyl phenoxyacetic acid propyl ester 60 Alucard (~q female d) Cloth 1 75 5 Ethofat 142/20 5 Aromasol (Mountain omasol) days Total 100 Examples 7 Each ingredient below to obtain a liquid composition in the form of a concentrated liquid.

% (W no V) 3-t-butylphenoxyacetic acid propyl ester 20 Duoterik M Old 1 5 Duoterik MB2 5 Cyclohexanone (3 customers) Xylene (1 customer)
The compositions described in Examples 5 to 7 above were diluted with water to contain 0.05 to 8.0% (w/v) 3-t-butylphenoxyacetic acid propyl ester (1 in 50 to 2000 liters). ~4k9) An emulsion for spraying is obtained.

For example, the liquid composition of Example 5 may be diluted at a rate of 1 part per 1 liter of water and sprayed onto the 20 to 30 arcs of the tips of growing annual fruit tree seedlings (e.g. apples and pears). .

As a result, side branches are actively generated while maintaining a preferable wide angle between the branches and the side branches of the tree. 'b} The liquid composition of Example 6 was diluted with water to give a concentration of 1,000 pm (60 pm as 3-t-butylphenoxyacetic acid propyl ester).
When injected into Brussels sprouts when the first 5 or 6 sprouts are present at a concentration of 0 Cape pm), it acts as an alternative to apical bud plucking by the method and increases the yield of Brussels sprouts. Demonstrates the effect of reducing wear and tear.

'c' The liquid composition of Example 7 was diluted with water to a concentration of 125.
If you make a liquid of snake pm (25 pm as 3-t-butylphenoxyacetic acid propyl ester) and spray it on young apple trees at dawn when the fruit is set, it will reduce the fruit production (
fruit thinning), the final fruit size increases and quality improves.
Example 8 3-tert-butyl phenoxyacetic acid propyl ester is sprayed without dilution using a microfog device at a rate of 1 to 2 k9/ha.

To improve fog coverage, 3-tert-butylphenoxyacetic acid ester is mixed with 1 to 5 liters/ha of non-phytotoxic fogging oil before application. Apply 3-t-butylphenoxyacetate propyl ester two weeks after cotton blooms.
Increases cotton yield when applied at a rate of 9/ha.

Example 9 The following components are mixed to obtain a liquid composition in the form of a concentrated liquid.

% (W/V) Butylphenoxyacetic acid centre.

Lopyle ester 10
Ethylan KEO I
Dimethylformamide Total 100 This composition was diluted with water to give 0.05% (50 pm) to 4.0% propyl ester of 3-t-butylphenoxyacetate.
(w/v) (4000 pm).

When an ant fog solution containing 4000 pm (4000 ppm as propyl ester of 3-t-butylphenoxyacetate) of the composition is sprayed 40 pm after sowing sunflowers, the yield of seeds and the average seed weight increase.

Example 10 When the compositions described in Examples 5-9 above are added to an aqueous solution containing 1% Perlankrol ESD-60, 0.05-1.0% 3-t-butylphenoxyacetic acid propyl ester is added. (w/v), which is dispensed in the form of a foam using a specific foam-generating hydraulic nozzle.

The substances with trade names used in the above examples have the following meanings:

Ethylan KEO: Solubilizer consisting of nonylphenol ethylene oxide condensate (ethylene oxide: 10 mol) Duoteric
s) MBI and M Old 2: Anionic/nonionic mixed emulsifier containing calcium alkylaryl sulfonate and alkylphenol ethylene oxide condensate Perlankrol ESD-60: From the sodium salt of a synthetic primary alcohol ether sulfate Foaming agent Ethofat 14
2/20: Emulsifier Alucard consisting of fatty acid/ethylene oxide condensate (~q skin d) Book-75: Jikoko (coc
o) Emulsifier consisting of dimethylammonium chloride (
Coco means alkyl derived from coconut oil) Aromasol H: Hydrocarbon oil containing 95% (v/v) of aromatic crab content (boiling point 168-200%) The effects of promoting tillering and increasing yield of paddy rice were tested as follows.

1 Test conditions {1} Test plot Paddy field ×4 of each plot 3
[2] Paddy rice variety Aichi Asahi '3- Rice transplant date May 2
5 days ■ Chemical solution 3-t-butylphenoxyacetic acid propyl ester (compound (1)) 90 parts, Atrox (Atrox) 485
An emulsion consisting of a mixture of 5 and ylan CA (3:1) and 1 part.

When spraying, compound (1) is 5000 1000 200,
Dilute with water to a pm of 4. Atl
ox) 4855 is manufactured by Honwell Atlas Co., Ltd.
eywell AtlasLimi has the trade name of d) a mixture of nonionic and anionic surfactants, Ariran (
Arylan) CA is manufactured by Lancro Chemical Company (Lan
This is the trade name of calcium dodecylbenzene sulfonate from kroChemicals Limited.

'51 Spraying timing and amount When there are 2 tillers/stock (June 5th) Sun), 150 evening/sprayed over the entire surface per snake.

'6' At the time of ripening on the survey day (September 15), 6 vermilion plants were cut from the center of each test plot, and the number of panicles and panicle weight per plant were measured.

The results are shown in Table 4.

Table 4

Claims (1)

[Claims] 1 3-t-Butylphenoxyacetic acid propyl ester. 2 Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ 3-t-, which is characterized by reacting a compound represented by ▼ (in the formula, X means a hydroxyl group, halogen, or an alkoxy group other than propoxy) with propanol. Method for producing butylphenoxyacetic acid propyl ester. 3. The method according to item 2 above, wherein the compound in which X is a hydroxyl group is used and subjected to a heating reaction under substantially anhydrous conditions in the presence of an acidic catalyst, optionally in an inert organic solvent or an excess of propanol. 4. The method according to item 2 above, wherein the compound in which X is a halogen is used, and the reaction is carried out in the presence of an acid binder, if desired, in an inert solvent, at room temperature to elevated temperature. 5. The method according to item 2 above, wherein the compound in which X is an alkoxy other than propoxy is heated in the presence of an acidic catalyst, optionally in an inert organic solvent or an excess of propanol, under substantially anhydrous conditions. 6 Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, M means an alkali metal) A compound represented by the formula: YCH_2COOR (in the formula,
Y is a halogen and R is an alkyl group), and then, when R in the above reaction example is an alkyl other than propyl, the obtained alkyl 3-t-butylphenoxyacetic acid ester is reacted with propanol. 1. A method for producing 3-t-butylphenoxyacetic acid propyl ester, which comprises reacting. 7. The method according to item 6 above, wherein the reaction is carried out in an anhydrous inert solvent at 0 to 100°C. 8. A plant growth regulating composition containing 3-t-butylphenoxyacetic acid propyl ester as an active ingredient. 9. The composition according to item 8 above, which contains at least one wetting agent, dispersing agent or emulsifying agent. 10 The wetting agent, quaternary ammonium derivative, nonyl-
and/or a condensation product of octylphenol with ethylene oxide and a carboxylic acid ester of anhidoasolpitol made soluble by condensing and etherifying free hydroxyl groups with ethylene oxide. 11 Insecticides, non-insecticidal compounds, fungicides, Bacillus thuringiensis
11. The composition according to any one of items 8 to 10 above, which contains one or more auxiliary compounds selected from the group consisting of an insect repellent (nsis) agent and an insect repellent agent. 12. The composition according to any one of items 8 to 11 above, wherein 3-t-butylphenoxyacetic acid propyl ester is diluted with water. 13. The composition according to any one of items 8 to 11 above, wherein 3-t-butylphenoxyacetic acid propyl ester is diluted with an organic solvent or a mixture of at least one organic solvent and water. 1
4. The composition according to any one of items 8 to 13 above, containing 0.05 to 90% (W/V) of 3-t-butylphenoxyacetic acid propyl ester. 15. A method for regulating plant growth, comprising applying an effective amount of 3-t-butylphenoxyacetic acid propyl ester to a growing or dormant plant composition. 16. The method of item 15 above, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to a harvest tree to increase its yield. 17. The method of item 16 above, wherein the tree is an apple, pear, peach, plum, tangerine or oil palm tree. 18. The method according to any one of items 15 to 17 above, wherein a composition containing 750 to 1500 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied. 19. The method of item 15 above, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to annual fruit tree seedlings to promote elongation of lateral branches thereof. 20 The first step is to apply a composition containing 750 to 1500 ppm of 3-t-butylphenoxyacetic acid propyl ester to a distance of 20 to 50 cm from the top of a one-year-old fruit tree seedling.
Method of Section 9. 21. The method of item 15, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to fruit trees that are 2 to 3 years old after being transplanted into an orchard to promote the production of secondary lateral branches. 22. The method according to item 21, wherein a composition containing 1250 to 1500 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied to fruit trees. 23. No. 21 above, wherein said fruit tree is an apple or pear tree.
Or the method of Section 22. 24. The method of item 15 above, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to ornamental plants to promote active growth and improve the shape, and in the case of trees, to promote the elongation of lateral branches thereof. . 25. The method according to item 24, wherein a composition containing 750 to 4000 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied. 26. The method according to item 15, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied at the time of flowering of a fruit tree, the time of fruit set of young fruit, or an intermediate time thereof to remove flowers or fruits and improve fruit quality. 27. The method according to item 26, wherein a composition containing 250 to 1500 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied. 28 The second fruit tree is an apple or a grape tree.
Method of Section 6 or Section 27. 29. The method of item 15 above, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to field crops to improve their yield. 29. The method of claim 29, wherein 3-tert-butylphenoxyacetic acid propyl ester is applied to field crops at a rate of 0.56 to 2.24 kg/ha. 31. The method of item 29 or 30 above, wherein the field crop is cotton, soybeans, adzuki beans, other legumes, peanuts, oilseed rape, or sunflowers. 32. The method according to any one of items 29 to 31 above, wherein the composition containing 3-t-butylphenoxyacetic acid propyl ester is applied to field crops at the time of flowering. 33. The method of item 15 above, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to cultivated crops that require pruning at a young stage. 34. The method according to item 33, wherein a composition containing 750 to 3000 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied. 35. The method of paragraph 33 or 34 above, wherein the crop is tea. 36 Said No. 15 in which an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to young trees to promote defoliation.
Section method. 37. The method of item 36 above, wherein a composition containing 1,000 to 10,000 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied to the young trees at the end of their growing season or before flowering. 38. The method of item 15 above, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to potatoes to increase their yield. 39. The method according to item 38, wherein a composition containing 1000 to 3000 ppm of 3-t-butylphenoxypropyl ester is applied. 16. The method of claim 15, wherein an effective amount of 40 3-t-butylphenoxyacetic acid propyl ester is applied to bud sprouts to increase yield and reduce wastage. 41. The method according to item 40, wherein a composition containing 4000 to 6000 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied at the time of bud formation. 42. The method of item 15 above, wherein an effective amount of 3-t-butylphenoxyacetic acid propyl ester is applied to tomatoes to suppress the formation of undesirable side shoots. 43 Said No. 42 applying a composition containing 3000 ppm of 3-t-butylphenoxyacetic acid propyl ester
Section method. 44 Applying an effective amount of 3-t-butylphenoxyacetic acid propyl ester to monocot plants to increase the number of tillers on their stems and to reduce the number of ineffective tillers that do not set flowers or set seeds, thereby increasing crop yields. 16. The method of item 15 above, which increases the amount. 45. The method according to item 44, wherein a composition containing 200 to 2000 ppm of 3-t-butylphenoxyacetic acid propyl ester is applied. 46. The method of paragraph 44 or 45 above, wherein the crop is wheat, barley or rice. 47 Nos. 15 to 4 above, in which the composition containing 3-t-butylphenoxyacetic acid propyl ester is applied by spraying.
Any method in Section 6.