JPS58164501A - Plant growth regulator - Google Patents

Abstract

PURPOSE:To provide a plant growth regulator exhibiting remarkable effect to retard the growth of especially gramineous plants such as lawn, rice plant, etc., and harmless to crops, by mixing a novel isonicotinic acid anilide compound with 2,4-D, etc., and using the mixture as an active component. CONSTITUTION:The titled regulator contains an active component obtained by mixing (A) one or more novel isonicotinic acid anilide compounds of formula (R1 is H or lower alkyl; R2 is H or OH; X is halogen or lower alkyl; n is 0-2; Z is H or halogen) having strong growth retarding activity especially to gramineous plants with (B) maleic acid hydrazide choline salt, 2,4-D (2,4-dichloro-phenoxyacetic acid), 2-chloro-4-methylphenoxyacetic acid, etc., which are known plant growth regulators and useful as growth retardant of lawn, lodging preventive for rice plant, dwarfing agent for flowers, etc. The preferable rate of application of the mixture is 100-3,000g/10a.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (I) (wherein 81 represents a hydrogen atom, 1+ represents a lower alkyl group having 1 to 4 carbon atoms, 8 represents a hydrogen atom, and 9 represents a hydroxyl group, X represents a halogen atom or a lower alkyl group having 1 to 2 carbon atoms, n represents an integer from O to 2, 2 represents a hydrogen atom, and 9 represents a halogen atom. 9 is 3 or more types, maleic acid hydrazide choline salt (hereinafter referred to as ro-MHJ), &4-ditharolphenoxyacetic acid (hereinafter referred to as "λ4-D"), 2-chloro-4-methylphenoxyacetic acid 112 (hereinafter referred to as rMOPJ') , S-benzi thiophosphate kQ, Q-diisopropyl (hereinafter referred to as rIBPJ), N
-(dimethylamino)-succinamic acid (hereinafter referred to as “B-
995J), (2-chloroethyl)trimethylammonium talolide (hereinafter referred to as ro00J), methyl-2-
Chlor-9-hydroxy-fluorene-(9)-carboxylate C (rOF-125J), λ4-dichlorobenzyltributylsulfos7onium chloride (hereinafter referred to as "Phos7on DJ") 4L<a2-10 ethylphos7onium chloride (hereinafter This product relates to a plant growth regulator containing a mixture of Ethrel J) as an active ingredient, and has a wide range of applications. The present invention provides a plant growth inhibitor with high practical value.

The innicotinic acid a-ydo compound, represented by the general formula [2], is used as a plant growth inhibitor, for example, for rice, it is used to prevent box-raised seedlings, to prevent elongation of seedlings, to prevent aging, and to prevent lodging of transplanted paddy fields. It is effective against a wide range of grass species, but
and <K exerts a high growth inhibitory effect on plants of the Poaceae family. Effective plants include the rice mentioned above, as well as wheat,
Examples include corn and grasses, but it also has a stable effect on Daito plants.

On the other hand, 0-MH, 2,4-D% MOF, IBP.

B-995,000,0F-125,7 Male 7-on D and Esrel are substances known as plant growth regulators, and have already been used as lawn growth inhibitors, rice lodging prevention agents, and flower FF.
Although it is a useful agent as a defoliant, it is not very effective when used alone, but in high doses it is useful because it causes browning of plants and delays the growth of new leaves. - There is a drawback that it takes some getting used to.

In order to solve these problems, the present inventors conducted various studies and combined the isonicotinic acid anilide compound represented by the above general formula (1) K with the above-mentioned known growth regulator, and treated the plants with the compound. It has been found that this method does not harm useful species at all, and has an excellent effect on regulating the growth of aquatic plants. In other words, the additive effect is 1! : showed a particularly strong growth-inhibiting effect on the grasses of the grass family, turf and rice, and in addition to extending the treatment period, unexpected synergistic effects were observed. In other words, these compounds have a significantly greater ability to inhibit plant growth than when used alone, and Kutoe exhibits a strong growth inhibiting effect even on lawns with a complete thatch layer. As a rice lodging prevention agent, no decrease in yield was observed at any time of treatment before rice production.

As described above, the present invention uses O-MH and 4-D% MOP as the isonicotinic acid anilide compound (1).

IBP, B-995,000, OF-125, 7 male 7
Regarding the dispute regarding plant growth inhibitors and lodging prevention agents that are formulated with plant growth regulators such as OnD or Ethrel, the performance as a plant growth regulator has been significantly improved due to the synergistic effect based on the combination of active ingredients. Each of the above-mentioned plant growth regulators used in the mixture of the present invention is a known plant physiologically active substance as a plant growth regulator or herbicide.
It is novel that a plant growth regulator exhibits a synergistic effect when combined with the compound represented by the formula. In addition, we also investigated the plant growth regulating effect of the mixed use of known plant growth regulators other than those mentioned above and the isonicotinic acid anilide compound used in the present invention.
Effectiveness was observed in most combinations. However, the combination with the above drugs had the highest practical value.

The compound of the present invention represented by general formula [1] is novel,
It can be manufactured by the method shown below.

(1) Innicotine halide represented by the general formula [舊], (in the formula, Y represents a halogen atom) is added to the innicotine halide represented by the general formula (in the formula, R1#
The compound represented by the general formula (1) is produced by reacting with the aniline derivative represented by nz e X *@ and 2 have the same meanings as above. in this case,
The reaction will proceed more smoothly if an appropriate deoxidizing agent is used. 9. Suitable solvents include hyricine, methanol, benzene, toluene, xylene, dichloromethane, dichloroform, tetrahydro7rane, dioquinane, a7ton, dimethylformand, and the like. Examples of deoxidizers include pyridine, triethylamine, caustic soda, potassium carbonate, sodium carbonate, and potassium carbonate.The reaction proceeds even at room temperature, but in some cases it can be carried out by cooling or heating. The reaction time is good, preferably 0 to 60°C. The reaction time depends on the selection of conditions, but it can be completed in 1 to 8 hours.
After completion of the reaction, the target product is obtained by separating and purifying by a conventional method (2) nicotine? ! A compound represented by the general formula CI) can be easily produced by reducing the II conductor with a suitable reducing agent.

Examples of the reducing agent include lithium aluminum hydride and sodium borohydride. In actual practice, it can be easily produced by using a conventional method for each reducing agent.

A manufacturing example will be given and explained below.

Production example 1゜N-methyl-isonicotinic acid-(4-chloro-2-(α
-Hydroxybenzyl))anilide (Compound No. 3) 2-Methylamino-5-chlorobenzhydrol 15t
was dissolved in 3011 L of pyridine, the solution was cooled with ice while stirring, and the solution was dissolved in isonicotinic acid chloride hydrochloride L4.
Add a little at a time to f'. This takes about 30 minutes.

! I! After stirring at room temperature for 3 hours, 20% water was added to the reaction solution.
When 0 dt is added, crystals precipitate out, and when these crystals are collected and recrystallized from a methanol-acetone mixed solvent, N-methyl-
Isonicotinic acid-(4-chloro-2-(α-hydroxybenzyl°))anilide 1.7f is obtained. Melting point 199~
201℃ Elemental analysis value: 0 Tomi・H1yOJIN Snow O! (molecular weight 3
51.81) OHN Calculated dependent country 6&08 486 7.94 Actual value country
67.96 498 7.79 In addition, the solvent was replaced with pyridine and benzene, toluene, xylene, dichloromethane, and chloroform were used.

The desired product was also obtained using tetrahydrofuran, dioxane, acetone, and dimethylformand.

Production Example 2 Isonicotinic acid-(4-10rho-2-(α-human-xybenzyl))anilide (Compound No. 4) Isonicotinic acid-(4-chloro-2-benzoyl)anilide L9ff Solution dissolved in methanol 20il# Add 0.2 f of sodium borohydride little by little while stirring. During this time, about 30 minutes were required, and the mixture was further stirred at room temperature for 2 hours. After the reaction was completed, 200 d of water was added, and crystals were precipitated. This crystal tp was collected and recrystallized from a mixed solvent of dimethylform and methanol to obtain isonicotinic acid (4-
Chloro-2-(α-hydroxybenzyl)ani17)'
llf? obtain. Melting point: 210-11℃ Elemental analysis: 01@H110ANlOj (molecular weight: 33
fL79) OHN Calculated country 67.36 4.46 &27 Actual value (2) 67.18 456 8J9 Note that the solvent was changed to methanol and used as pyridine, benzene, toluene, xylene, and dichloromethane.

Chloroform, tetrahydro7ran, dioxane.

The desired product was also obtained using acetone and dimethylformamide.

Production Example 1 Inonicotinic acid-(4-chloro-2-benzyl)anilide (compound number 1) 4-chloro-2-benzylaniline 1.3 fl pyridine 3011LIK was dissolved, the solution was cooled with ice, and while stirring, Add nicotinic acid loridodate L4 ft little by little. This takes about 30 minutes. The mixture was further stirred in the chamber for 3 hours to complete the reaction. Add 200 g of water to this reaction solution.
When added, crystals precipitated.

When these crystals were collected and reconstituted with ethanol, inonicotinic acid-(4-10-2-benzyl)anilide L6 ft
- get. Melting point 178-179℃ Elemental analysis value: 01@H
1i01N snow 0 (as molecular weight 32179) OHN Calculated value -70,70468&68 Actual value (2) 7α75 4.79 &65 Typical examples of compounds that can be used are shown in Table 1 6 The present invention is limited only to these exemplified compounds. Note that compound numbers are also referred to in the following Examples and Experimental Examples.

The plant growth regulator of the present invention is a mixture of one or more of the compounds represented by the general formula [I] and each of the plant growth regulators.
It is appropriate to use F, preferably at a ratio of 150 to 2000 F, but it goes without saying that the dosage can be adjusted as appropriate depending on the cultivation conditions and growth conditions of the plant 6 For example, when treating foliage 150-200
09 is suitable, and a seedling box (30 css x 60 e
x x 3 tx ) When processing K, use at a rate of 2 to 1509 per 10 ares (20 boxes).

Additionally, when preparing formulations, it can be mixed with various solid and liquid carriers used in the preparation of general anti-cancer drugs to produce wettable powders, emulsions, single powders, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, penetrants, and binders may be added to the drug. It can be used in combination with agents, plant growth regulators, fertilizers, etc.

The carrier referred to here may be either solid or liquid; examples thereof include talc, clay, kaolin, diatomaceous earth, calcium carbonate, wood flour, and # powder.

Gum arabic, water, alcohol, kerosene, naphtha, quidylol, xylene, cyclohexanone.

Methylnaphthalene, benzene, acetone, etc. are used as adjuvants used in drug formulations, such as spreading agents, emulsifiers, dispersants, wetting agents, etc. Nonionic agents (diethylene alkylphenyl ether in polio, ethylene oxide propylene oxide, etc.) copolymer, lignin sulfonate,
sorbitan esters, etc.), anionic products (soaps, sulfated oils, etc.).

Alkyl 6R ester group 2 petroleum sulfone) III
.

dioctyl sulfosuccinate salts, alkylaryl sulfonates, etc.), cationic (aliphatic amine salts,
quaternary ammonium salts, alkylpyridinium salts, etc.) and amphoteric systems (alkylaminoethylglycine, alkyldimethylbetaine).

Examples include surfactants such as polyglycol sulfate esters, alcohol-based sulfone esters, etc.).

However, it goes without saying that the uniformity of implementation of the present invention is not necessarily limited to the above-mentioned dosage forms.

In addition, in formulating the formulation, the mixing ratio is 5 to 45% of the compound represented by the general formula CI) and 1 to 25% of the above plant growth regulator.
! Surfactant G~15% carrier 30-94% is optimal. Note that depending on the dosage form, it is not necessary to add a surfactant.

In addition, in the present invention, various drainage agents and bactericidal agents are used.

Herbicides, plant growth regulators, acaricides, acaricides.

By using it in combination with attractants, repellents, plant nutrients, #P additives, etc., a wider range of effects can be expected.

The chemical of the present invention may be used during, for example, the sowing period, the seedling period, or the growing period, and depending on the target plant, treatments such as spraying on the ground, water and soil, and immersion can be performed.

Next, an experimental example will be shown to explain the effects of the present invention in detail.Experimental Example L A 115,000 are plastic bot was filled with sandy loam, and Kentara Keep Plug grass was sown.

After cultivating nine lawns using a conventional method for three years and cutting the grass to a height of α5mK, isonicotinic acid anilide compounds, O-MH, Ethrel, B-995, 000, Phosphone D and 0F
-125 alone was formulated in the same way, and the concentration of the active ingredient in the composition was kept constant by increasing or decreasing the amount of clay. ) what you got,
The treatment was carried out by diluting KIO (at a rate of 1/10 heat) with water to reach the prescribed dose. From then on, it was maintained in a glass greenhouse until the survey date. To investigate the effect, the plant height of 0κ grass was At the same time as the measurement, the above-ground part was harvested with 0.5aIIt remaining, and its fresh weight was measured.

The results are shown in Table 2.

Experimental example λ Green at a golf course where bentgrass is a concern (grown for 5 years) Section t-1 is divided into 2m x 2m sections, and the above-ground part is 0.5m.
After harvesting to a height of 100 m, the isonicotinic acid anilide compound, B-995,0-MH, Ethrel, 0F-125,
000 and Phosphone D alone were formulated in the same way, and the amount of xylene was increased or decreased to keep the concentration of the active ingredient in the composition constant. ) diluted with water to the specified amount,
Use a small poop container to make sure that it adheres well to the eastern part of the stem.
Sprayed at a rate of 0.01/10 a. The investigation of the effect is
30 days after chemical treatment, the plant height and fresh weight of the aboveground part of the 0K grass (
The height of the plant (cut to a height of 0.51) is kept constant.

The results are shown in Table 3.

No. 38 Experimental example of growth inhibition effect on bent grass 1 FiIIIi seedling rice (variety Ekoshihikari) was mechanically transplanted in a paddy field using a conventional method (May 20, 1980), and ears appeared at 42
One day in advance, the isonicotinic acid anilide compound, 2.4-D, IBP, B-995, MOP, and 000 monomer were divided into 1 section and 1 ON/unit, and made into granules using the exfoliating method shown in Example 3 below. A formulation for use was similarly prepared, and the concentration of the active ingredient in the composition was kept constant by increasing or decreasing the amount of bentonite. ) Sow the specified amount of 90% in the area, then maintain the water depth at 3 to 51 ft. The effect will be investigated on the culm length on August 30th, and the lodging on October 1st. f was investigated.

The results are shown in Table 4.

Next, examples of the present invention will be shown, but the compounds, carriers, and proportions used are not limited to these examples.

Example 1゜Compound N&4 40 parts by weight 0F-12
520# Alkyl sulfuric acid 51 -
35 l Mix these thoroughly until homogeneous and pulverize to obtain an irrigation agent. When using this, add 1 predetermined amount of water.
1 [K diluted and sprayed.

Example 2 Compound m1 20 parts by weight 8 995
5 7F Palm ethylene phenyl ether 7I Calcium alkylbenzene sulfonate 31 Xylene 40 #Cyclohexanone 25 # Mix and dissolve these ingredients thoroughly until homogeneous to obtain an emulsion. When using this, add water to the specified 111
Dilute fK and spray.

Example 1 Compound Ak5 10 parts by weight λ4
-D L5 #Bentonite 53 17479
35.5# These are mixed until uniform, finely pulverized, and granulated by a conventional method to be used as granules.

Source: Chugai Pharmaceutical Co., Ltd. Continuation of page 1 0 shots clear person Hiromi Tomioka 3-41-8 Takada, Toshima-ku, Tokyo Inside Chugai Pharmaceutical Co., Ltd. 0 shots clear person Yoshitaka Iwane 3-41-8 Takada, Toshima-ku, Tokyo Inside Chugai Pharmaceutical Co., Ltd. 0 shots: Yasushi Murakami 3-41-8 Takada, Toshima-ku, Tokyo Inside Chugai Pharmaceutical Co., Ltd.

Claims (1)

[Claims] (In the formula, R1 represents a hydrogen atom, 9 represents a lower alkyl group, and R
, represents a hydrogen atom or a hydroxyl group, X represents a halogen atom or a lower alkyl group, II represents an integer from O to 2, and 2 represents a halogen atom before the hydrogen atom. Motoku has two or more types and maleic acid hydrazide purine salt. &4-dichlorophenoxyacetic acid, 2-chloro-4-methylphenoxyacetic acid, 8-benzyl Q thiophosphate, O-diisopropyl, N-(dimethylato))-xp-sinacetic acid, (!-thalole?#) ) Limethylammonium chloride, methyl-2-chloro-9-hydro-oxy-fluorein-(9)-carboxylate, λ4-dichlorobenzyltributyl 7-osulfonium thalide or 2-chloroethyl 7-osulfonium thalide and os
A plant growth regulator containing t% mold as an active ingredient.