JPH0285251A - Plant growth regulator - Google Patents

Abstract

PURPOSE:To obtain a plant-growth regulator effective in promoting the sprouting and initial growth of plant by using one or more kinds of indole derivatives (some of which are novel) as active components. CONSTITUTION:The objective plant growth regulator contains, as active components, one or more kinds of indole derivatives (e.g., 2-chloroindole-3- carboxyaldehyde) including novel indole derivatives of formula I (X is -CHO; Y is H, halogen, lower alkyl, phenyl, pyridyl, 3-hydroxy-3-methyl-1-buten-1-yl or 2-methoxycarbonylethen-1-yl; Z is H; R is 3-methyl-2-buten-1-yl) [e.g., 2- bromo-1-(3-methyl-2-buten-1-yl)indole-3-carboxyaldehyde of formula II]. The agent is applicable to rice, wheat, cucumber, tomato, flowers, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a plant growth regulator containing a specific indole derivative as an active ingredient and a novel compound not described in any literature.

[Conventional technology and problems]

Conventionally 1, various studies have been conducted on indole derivatives,
It is known that certain indole derivatives are useful as plant growth regulators.

For example, Japanese Patent Application Laid-Open No. 61-8760, which the present applicant previously applied for,
No. 4 discloses that certain indole derivatives are useful as plant growth regulators, particularly as grape fruit drop preventive agents.

However, there is also a demand for the development of drugs that are excellent in promoting the growth of useful plants, particularly in promoting early growth.

That is, useful plants with excellent initial growth promotion are expected to ultimately contribute to increased yield and improved quality.

Means for Solving Problem G] As a result of further various studies on indole derivatives, the present inventors found that when a specific indole derivative was treated with useful plants, their growth promotion, especially early growth promotion, was excellent. He has discovered that it is true and has completed his true mission.

The specific indole derivatives of the present invention are mostly known compounds, but also include new compounds not described in literature.

That is, the present invention provides - Monana [■]: [In the above formula, X
represents -CIIO,l, a lower alkyl group substituted with a nitro atom or a lower alkenyl group substituted with a nitro atom, and Y is a hydrogen atom, a halogen atom, a lower alkyl group, a phenyl group, a pyridyl group, 3- represents a hydroxy-3-methyl-1-buten-lyl group or a 2-methoxylponylethen-1-yl group, Z represents a hydrogen atom or a halogen atom, and R represents a hydrogen atom or a 3-methyl-2-butene Represents a -1-yl group.

However, the case where X is a -CIIO group and Y, Z and R are all hydrogen atoms is excluded. ] This relates to a plant growth regulator characterized by containing as an active ingredient one or more of the indole derivatives represented by [X represents a 0110 group, and Y is a hydrogen atom, a halogen atom, a lower alkyl group, a phenyl group,
Pyridyl group, 3-hydroxy-3-methyl-1-buten-1-yl group or 2-methoxylponylethene-1
-yl group, Z represents a hydrogen atom, and R represents a 3-methyl-2-buten-1-yl group. ] Examples include indole derivatives represented by the following.

Useful plants to which the plant growth regulator of the present invention is applied are not particularly limited, but include, for example, cereals (rice, wheat, etc.)
, vegetables (cucumbers, tomatoes, etc.) and flower petals.

Treatment methods for plants that are useful for the plant growth regulator of the present invention include, for example, seed soaking treatment, seed dressing treatment, bed soil mixing treatment, and foliage spraying treatment.These treatments promote germination and early growth of plants. It is possible to promote

Promoting germination and early growth of plants is expected to ultimately increase yields, especially in direct sowing cultivation of cereals (e.g., paddy rice), and also helps produce good seedlings during the seedling process of vegetables and flower petals. This contributes to improving its quality, and therefore promoting germination and early growth of plants is extremely important.

Table 1 specifically lists examples of active ingredient compounds of the plant growth regulator of the present invention.

However, the active ingredient compounds are not limited to these.

(Hereafter, margin) Table 1 next, Regarding the method for producing the compound of the present invention, reaction formula General formula [I ] To give a concrete example, It is as follows.

/11 In the compound represented by Compound no.

(Compound Nα1) (Compound No. 2) (Compound No. 2) The pH in Table 1 is phenyl group, teeth, Piriji group, teeth, Represents a pyridyl group.

H3 (Compound No. 3) (Compound No. 3) (Force (Compound No. 2) C11°f (Compound No. 4) (Compound No. 7) (Compound No. 4) lh (Compound No. 5) ( Compound No. 2) (Compound Nα2) (Compound No. 6) (Compound No. 9) aO) (Compound Nα2) (Compound No. IO) (II) (Compound No. 2) (Compound No. l l) ■■ (Compound No. 12) In the above compound group, compound No. 6 is a new compound that has not been published in any literature.

Other compounds include heterocycles (IIETERO
-CYCLES) Vol. 27, No. 7 (1988).

Next, specific examples of synthesis of the compounds of the present invention will be described. However, it is not limited to these only.

Kinwei Kaito Synthesis of 2-chloroindole-3-carboxaldehyde (compound Nα1) A Vilsmeier reagent was prepared by adding 2.0 mff1 of phosphorus oxychloride to 2.0 mff1 of anhydrous N,N-dimethylformamide under water-cooling and stirring. A solution of 830.3 ml of oxindole dissolved in 8.0 mf of anhydrous chloroform was added to this liquid, and the mixture was stirred at room temperature for 7 hours and then stirred under reflux for an additional 15 hours. The reaction solution was poured into ice water and extracted with chloroform. The aqueous layer was neutralized with sodium hydrogen carbonate and extracted with a methylene chloride-methanol (9:1, v/v) mixed solvent. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: methylene chloride) to obtain 544.1 ml (48.6%) of the desired product.

Colorless prism product (methanol) mp 229-230°C (literature value mp 232-2
35°C) IR (KBr): 3082.1637.1
432 c+n-'' II-NMR (CDIOD)
δ: 6.87-7.36 (311, m), 7.85
~8.17 (111, m), 9.85 (III, s)
.

MS m/z: 181,179 (M”) Kim Seo I
2-bromoindole-3-carboxaldehyde (
Synthesis of Compound No. 2) Add 0% phosphorus oxybromide to 2.0++ l of anhydrous N,N-dimethylformamide under ice-cooling and stirring.
．． A Vilsmeier reagent was prepared by adding 8mff1.

To this solution, add 408.1 cm of oxindole and 8.1 cm of anhydrous chloroform. On/! A solution dissolved in was added thereto, and the mixture was stirred under reflux for 20 hours.

The reaction solution was poured into ice water and extracted with chloroform.

The aqueous layer was neutralized with sodium hydrogen carbonate, and methylene chloride
Extraction was performed with a methanol (9:1.v/v) mixed solvent.

The extract was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: methylene chloride) to obtain 329.9 mg (48%) of the desired product.

Colorless prism product (methanol) mp 208-210'C IR (KBr): 3100. 1645. 1430
cm-''II-NMR (DMSO-d6) δ:
6.96-7.54 (311, m), 7.888.1
4 (III, m), 9.82 (ltl, s).

MS rn/z: 225,223 (M”) Kananari■
Synthesis of (E)-(3-hydroxy-3-methyl-1-buten-1-yl)indole-3-carboxaldehyde (compound No. 3) 2-bromoindole-3-carboxaldehyde 1.
6098g and E-(3-hydroxy-3-methyl-■-
Buten 1-yl) trilobed chirutin 3.9743
Add N, N dimethylformamide palladium acetate 156.3 cm, and heat at 93-110°C.
The mixture was heated and stirred for 2 hours. Methanol-ethyl acetate (1:9.v/v) mixed refrigerant was added to the reaction solution (
50mj2) Remove insoluble matter! I left. The filtrate was washed with saturated brine, and the organic layer and aqueous layer were separated. The aqueous layer was further extracted using the mixed medium described above. After extraction, the organic layers were combined, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained crude crystals were recrystallized from methanol to obtain 941.8+ng of the target product. Mother; night silica gel column chromatography (? volume 't8 medium: ffl[
Ethyl ester-n-hexane-1=1, v/v) was used to further obtain 465.7 mg of the desired product. Total yield: 1.4075g (85.5%).

Colorless prism product (methanol) mp 194-195'C IR (KBr): 3165.1614.1583.1
459.1372 cm+I-NMR (CD30D)
δ: 1.47((ill,s) 6.75(II
I, d, J=1611z), 7.02-7.48 (3
1! , mL 7.20 (LtLd, J=1611z)
7.99-8.23 (III, m), 10.18 (
III, s) MS m/z: 229 (M') Elemental analysis value: C+4111sNO2 as CII
N Calculated value? 3.34 6.59 6.11 Actual value 73
．． 17 6.64 6.05 can-1jj-(U,E)
-(3-hydroxy-3-methyl-1-butene-1
Synthesis of (E)-(3-hydroxy-3-methyl-1-butene-)-2-nitrovinylindole (compound Nα4)
yl)indole-3-carboxaldehyde 704
゜9 mg dissolved in 35 nl of nitromethane was mixed with 1.3701 g of ammonium acetate, which had been thoroughly dried in advance.
g, and the mixture was heated and stirred at 80 to 100°C for 1.5 hours.

The generated red crystals were collected by filtration and washed with water to obtain 746.
Obtained 9 tng. The filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (elution solvent: acetic acid ethyl ester-〇-hexane-1:I, v/■).
An additional 20.4 mg of the target product was obtained. Total number 1767
．． 3 mg (91,6%).

Red needle crystals (methanol) mp 256-257°C IR (KBr): 3250,1613. 1578
．． 1215 cm-''II-NMR (pyridine-
d,) δ: 1.47 (611, s), 6.83 (Ll
l.

d, J=15.611z), 7.02 ~ 7.47
(311, m), 7.35 (IIId, J=15.
611z), 7.71 ~ 7.95 (III, m)
, 8.09 (IIId, J=13.211z),
8.66 (III, d, J=13.211z) phylum S
m/z: 272 (M') Elemental analysis Ueji C1
51116N203・l/4 CI as II□0
I N Calculated value 65.09 5.97 10.20 Actual value 6
5.33 5.92 10.02
)-(3-Hyl: Roxy-3-methyl-1-butene-1
Synthesis of (E,E)-(3-hydroxy-3-methyl-1-buten-l-yl)-2-nitrovinylindole 752.3
mgmethanol 150mI! To the solution dissolved in , 636.6 mg of sodium borohydride was added under IR pressure at room temperature, and the mixture was further stirred for 20 minutes. Methylene chloride and saturated brine were added to the residue obtained by distilling off the medium (under σ pressure), and 0.1N hydrochloric acid was added dropwise with thorough stirring to bring the aqueous layer to pH 117. The organic layer was separated, and the aqueous layer was mixed with methylene chloride-methanol (95:5゜v/
v) Extracted with a mixed solvent. The organic layer and the extract were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: ethyl acetate and hexane 2:3.v/v),
711.8 mg (93.4%) of the target product was obtained.

Colorless prism product (Hensen) mp 93-95'C IR (KBr): 3560.3270.1548 1
375 cm-+1-NMR (CDCffi 1) δ:
1.48 (6tl, s), 3.49 (211,t,
J=7.511z), 4.55(211,t, J=7
．． 511z), 6.12(ill, d, J.

1611z), 6.68(Ill, d, J=16!I
z), 6.94-7.54 (411゜), 8.2
0 (Ill, brs, NiN11) m/z: 27
4(M') Elemental analysis value: C+sl+eNzO: CII as +
N Calculated value 65.67 6.61 10.21 Actual value 6
5.89 6.58 10.23 Synthesis of 2-bromo-1-(3-methyl-2-buten-1-yl)indole-3 carboxaldehyde (compound No. 6) 2-bromoindole- 3-Carboxaldehyde 1.
0176 g of tetrahydrofuran was dissolved in 60 ml of tetrahydrofuran, and 300.0 g of tetra-n-butylammonium bromide was added to the solution.
8■, 3.5656 g of anhydrous potassium carbonate was added, and a solution of 1.0605 g of prenylbromide dissolved in tetrahydrofuran 1011 IP was added, and the mixture was stirred at room temperature for 6 hours. Saturated brine was added to the reaction solution, and extracted with a methylene chloride-methanol (95:5.v/v) mixed solvent. After drying the extract over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent solvent: methylene chloride).
．． 2235g (92.3%) of the desired product was obtained.

Colorless needle crystals (n-hexane) mp 78.5 ~ 79°C IR (KBr): 1648, 137B, 1037.
748cm-''If-NMR (CDCf:l)δ:
1.74 (311,brs), 1.9H311
brs), 4.84 (211,brd, J=6.5
11z), 5.18 (III, brt.

J=6.511z), 7.12~7.37(311
, m), 8.16-8.42 (III, m),
10.00 (III, s) MS m/z: 29
3. 291 (M”) Elemental analysis value: Cztlz
CII N as BrNO Calculated value 57.55 4.83 4.79 Actual value 5
7.58 4.84 4.80 cure” (Example j-2-(2
-methoxylponylethenl-yl)indole-3
-Synthesis of carboxaldehyde (compound No. 7) 2-bromoindole-3-carboxaldehyde 102.2■
in 1 ml of N,N-dimethylformamide was added 248.6 mg of tetraeuphytylammonium chloride, (E)-)-n-butyl (2
Methoxyluponylethen-1-yl)tin 254.2
mg to ml of N,N-dimethylformamide? The mixed solution and 12.1 mg of palladium acetate were added, and the mixture was stirred at 110 to 115°C for 3 hours. The solvent was distilled off under reduced pressure, saturated brine was added to the resulting residue, and the mixture was extracted with a mixed solvent of ethyl acetate-methanol (95:5.v/v). Wash the extract with saturated salt water and anhydrous sulfuric acid)
After drying, the solvent was distilled off under pressure, and the resulting crude crystals were recrystallized from methanol to obtain 58.1 mg of the desired product. The mother liquor was further subjected to silica gel column chromatography (
Elution solvent: methylene chloride-methanol = 99:1.
v/v) to obtain 12.1 cm of the desired product. Total number M
70.2 mg (67°2%).

Pale yellow needle crystals (methanol) mp 261-262°C [R (KBr): 3200.1?10.1640.1
589 cvn-'+I-NMR (pyridine-dS) δ
: 3.72 (311, s), 6.95 (III, d
, J=1611z), 7.25-7.49 (311,
m), 8.50 (Ill, d, J=1611z),
8.59 8.77 (III, m), 10.71 (I
II, s) MS m/z: 229 (Mth) Elemental analysis value: C+ ill+ CII as 1NO3
N Calculated value 68.11 4.84 6.11 Actual value 6
7.89 4.76 6.04 Combined Example E 2-Methylindole-3-carboxaldehyde (8 for compound)
Synthesis of 2-bromoindole-3-carboxaldehyde 46
To a solution of 7.8 ■ and 562.2 + ng of tetramethyltin dissolved in 20 III of IJ,N dimethylformamide, 1.3443 g of tetra-nibutylammonium chloride and 42.7 mg of palladium acetate were added.
Stirred at 110-120°C for 16.5 hours. The solvent was distilled off under reduced pressure, and saturated brine was added to the resulting residue, followed by extraction with a mixed solvent of ethyl acetate-methanol (9:l, v/v). The extract was washed with saturated saline, and anhydrous sulfuric acid was added.
After drying, the solvent was distilled off under reduced pressure, and the resulting residue was separated by silica gel column chromatography (elution solvent: ethyl acetate - hexane = 1:l, v/v). A combined fraction of indole-3-carboxylic acid and indole-3-carboxylic aldehyde was collected. When this is recrystallized from methanol, the target product is 93.9
Obtained as mg pure crystal. Jan was further purified by silica gel preparative thin layer chromatography (developing solvent: methylene chloride) to obtain 54.2 mg of the target product and indole-3.
A mixture containing only carboxaldehyde was obtained. The ratio of both compounds is 'II-NMI? Therefore, the ratio was 2:1. Therefore, the yield of the target product was 130 mg (39.2%).

Colorless needle crystals (methanol) mp 204-205°C 11l (KBr): 3240.1632.1462.
1378 cu+-'II-NMR (CD, OD)
δ: 2.63 (311, s), 6.89-7.39
(311, m), 7.79-8.12 (III, m)
, 9.82 (III, s) MS m/z: 159
(M”) Elemental analysis value: C1゜II 9, CHN as 'IO Calculated value ?5.45 5.70 8.80 Actual value 7
5.50 5.62 8.82 t4LL Synthesis of 2-phenylindole-3-carboxaldehyde (compound No. 9) 2-bromoindole-3-carboxaldehyde 41.1 mg and tetraphenyltine 117.4 N.

N-dimethylformamide , tetra-n-butylammonium chloride 97.

Add 7 mg, palladium acetate 4.3■, 105~1
The mixture was stirred at 13°C for 3 hours. The solvent was distilled off under reduced pressure, and saturated brine was added to the resulting residue, which was extracted with a mixed solvent of ethyl acetate and methanol (95:5, v/v). The extract was washed with saturated saline, dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent: methylene chloride) and silica gel preparative thin layer chromatography (developing solvent). : methylene chloride-n-hexane) was repeated to obtain 27.7 mg (68.3%) of the desired product.

Colorless prismatic crystal (methanol) mp 260.5-263'C IR (Br): 162B, 1580, 1455
．． 1372 cm-'II-NMR (pyridine-dS
) δ: 7.18~7.90 (811.m) 8,53~
8.9H111,m), 10.25(III,s)
MS m/z: 221 (M”) Elemental analysis value: C, 51+, , No. C II
N Calculated value 81.43 5.01 6.33 Actual value 81.51 4.92 6.35 Synthesis example 10
Synthesis of 2-(2-pyridyl)indole-3-carboxaldehyde (Compound No. 10) 2-furo-indole-3-carboxaldehyde 110
0.5 mg and trimethyl(2-pyridyl)tin 1
, 0730 g of N,N-dimethylborumamide 7
246.1 ml of tetra-n-butylammonium chloride and 10 ml of palladium acetate were dissolved in the solution. 9 m
g and stirred at 111-113°C for 3 hours. The solvent was distilled off under reduced pressure, and the resulting residue was made alkaline (p
H9) and then acetic acid ethyl ester-methanol (9
Extracted with a 5:5, v/v) mixed solvent. The extract was washed with saturated brine, dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. V) and silica gel preparative thin layer chromatography (developing solvent: methylene chloride) are repeated to separate the target product. 0 mg (5.0
%) obtained. In addition, raw material recovery was 24.3n+g (2
4. 2%).

Colorless needle crystals (methanol-water) mp 225.5 - 226.5°C IR (KBr): 3070, 1618. 1575
．． 1440 cm+I-NMR (pyridine-aS) δ
: 7.12-7.70 (411, m).

7, 75 (III, dd, J=7.5 and 2
11z), 8'. 07 (III, dt.

J=8 and lllz), 8.65 8.7
8 (III m) 8.78-8, 98 (111, m
), 11.04 (III, s) MS m/z: 2
22 (M') elemental analysis value: CI4111ON20
As C II N Calculated value 75.65 4.54 12.61 Actual value 75.42 4.38 12.83 Kinweien■2- (
3-pyridyl) indole-3 carboxaldehyde (
Synthesis of compound No. 11) 2-bromoindole-3-carboxaldehyde 10
3.1■ in 3 ml of N,N-dimethylformamide, add 261% of tetra-butylammonium.
．． Added 3 ■. Furthermore, 221.0 mg of 3-pyridyl (trimethyl)tin was added to N, N ~ dimethylformamide 2
11! and 9.7 μm of palladium acetate were added thereto, and the mixture was stirred at 110-113°C for 3 hours.

The solvent was distilled off under reduced pressure, saturated brine was added to the resulting residue, and saturated sodium bicarbonate was added to make it alkaline (pH 8.5), followed by acetic acid ethyl ester-methanol (95: 5.v/v). ) Extracted with a mixed solvent. The extract was washed with water, dried with anhydrous sodium sulfate, and then the solvent was distilled off. The crude crystals obtained were mixed with ethyl acetate and hexane (3:
1. Recrystallization from (v/v) yielded the desired product of 15.3 cm.

This product was then subjected to preparative thin layer chromatography on silica gel (developing solvent: methylene chloride-methanol-95:5
．． v/v) to obtain 12.0 mg of pure product. Meanwhile, the recrystallized mother liquor was subjected to silica gel column chromatography (
Capacity: Ethyl acetate-n-hexane-3
:1. v/v), 16.4 mg of a 1=2 mixture of indole-3-carboxaldehyde and 2-methyl-3-indolecarboxaldehyde (determined from 'II-NMR) [2-methyl compound 10.9 m
g (14.9%) and indole-3-carboxaldehyde 5.5■ (8.1%)], the desired product was 27.
1 mg was obtained. Total yield 39.1 mg (38.3%).

Colorless needle crystals (methanol) rnp 246-246.5°C IR (KBr): 3130.162B, 1580
．． 1453 cm-'+I-NMR (pyridine-dS
) δ: 7.28-7.70 (411, m).

8.14 (III, ddd, J=8.2. and 1
．． 61lz), 8.75-8.96 (2H, m),
9.27 (Ill, dd, J=2.2 and O, 8
11z).

10.41 (III, s) MS m/z: 222 (M”) Elemental analysis value: C+411+oNzO and C11N Calculated value ?5.65 4.54 12.61 Actual value 7
5.48 4.47 12.50 AdI type 6-iodo-3-indolecarboxaldehyde (compound N1
1l 2) synthesis of anhydrous N,? J-dimethylformamide 2.5 mj2, phosphorus oxychloride 1.8 On/! Add while stirring on ice.

A Vilsmeier reagent was prepared by stirring at room temperature for 15 minutes.

To this, 1.3007 g of 6-iodoindole was added to anhydrous N
, N-dimethylformamide in 3 ml was added thereto under stirring while cooling with water, and the mixture was stirred under cooling with water for 2 hours and at room temperature for 10 hours. Water was added to the reaction mixture on water cooling, and the mixture was made alkaline (pl+10) by adding 33% aqueous sodium hydroxide solution, and then extracted with methylene chloride-methanol (4:I, v/v). The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained crude crystals were recrystallized from methanol to obtain 1.0061 g of the desired product. The mother liquor was further concentrated to obtain 253.1 mg of the target product. Total yield 1.259 g (86.8%).

Colorless needle crystals (methanol) mp216°C IR (KBr): 3173.1639.1522.
1436.1415.1384cm-'' II-NM
R (CD30D) δ: 7.52 (III, dd,
J=8.5 and 1.511z), 7.85(I
II, dd, J=1.5 and 0.711z),
7.95 (III, d, J=8.511z), 8.
05 (III, s), 9.89 (Ill, s) MS
m/z: 27HM”) Elemental analysis value: CII as C911blNO
N Calculated value 39.8B 2.23 5.17 Actual value
39.97 1.90 4.77 (hereinafter, blank) Next, when the compound of the present invention is used as an active ingredient of a plant growth regulator, the formulation form is not particularly limited, but it is usually an emulsion, an aqueous formulation, etc. Forms such as Japanese preparations and powders are desirable.

The concentration of the compound of the present invention used varies depending on the type of compound, the purpose of use, the type of target plant, the time of use, and other conditions (although -C is 0.01 to 100%
00 ppm, but preferably 0.1 to 1
It is appropriate to use it at about 000 ppm.

Specific formulation examples are shown below, but the invention is not limited to these.

In addition, in the following formulation examples, "parts" mean parts by weight. Tsurupol 26t30 is a product name of Toho Chemical Co., Ltd. and is a mixture of a nonionic surfactant and an anionic surfactant, and Tsurupol 5039 is an anionic surfactant.

Zeeklite PPP is a trade name of Zeeklite Industries Co., Ltd., and is a mixture of kaolinite and sericite.

Example 1 - Emulsion Invention Compound No. 12 ------- 1
0 parts Xylene --- 70 parts Tsurupol 2680 --- 1 --- 20 parts The above components are mixed uniformly to form an emulsion.

Before use, dilute with water to a predetermined concentration.

Manufacturing process 1 Wettable powder Compound No. 2 of the present invention -------
10 parts Sieglite PFP - 85 parts Tsurupol 5039 5 parts The above ingredients are mixed and ground to make a wettable powder.

When using it, either dilute it with water to the specified concentration or treat it.
Or mix it directly into the soil.

Manufactured by M±U Powder Compound No. 3 of the present invention 1 part Sieglite PFP - 99 parts The above components are mixed and ground to form a powder.

When using, treat as is without diluting with water.

Next, the effect of the compound of the present invention as a plant growth regulator will be specifically explained with reference to test examples, but the present invention is not limited to these.

A petri dish with a diameter of 7.5 cm+ was lined with filter paper, and 10 ml of a chemical solution of a predetermined concentration was poured into it.

After placing 10 rice germinated seeds (variety: Nipponbare) in the petri dish, they were grown in a bright room (25°C) with fluorescent lights on for 6 days.After this, the plant height and seed root length were measured. The results are shown in Table 2, and the results of seed root length are shown in Table 3.The values in Tables 2 and 3 are based on the plant height (26
, 7 mm) and seed root length in the untreated plot (46, 8 mm)
The relative value is shown when the value is set to 100. This test example 1
The comparative compound used in the following Test Example 2 is the following compound described in JP-A-61-87604.

■ Table 2 (Results of plant height) 67° Table 3 (Results of seed root length) Test 1 u forceps % A petri dish with a diameter of 7.5 cm was lined with filter paper, and 10 ml of a chemical solution of a predetermined concentration was added.

After placing 7 cucumber seeds (variety: Wasumi Hanshiro) in the Petri dish, they were grown in a bright room (25'C) with a fluorescent light on for 6 days. After this, plant height and seed root length were measured. The results for plant height are shown in Table 4, and the results for seed root length are shown in Table 5.

The values in Tables 4 and 5 are based on the plant height (
13,5 mIm) and seed root length in the untreated plot (12,1
The relative value is shown when 1III+) is set to 100.

(Hereafter, margin) Table 4 (Results of plant height) Table 5 (Seed root length results) O0

Claims (2)

[Claims] (1) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] [In the above formula, X is a -CHO group, a lower alkyl group substituted with a nitro atom, or a lower alkyl group substituted with a nitro atom. Represents a lower alkenyl group, and Y is a hydrogen atom, a halogen atom, a lower alkyl group, a phenyl group, a pyridyl group, a 3-hydroxy-3-methyl-1-buten-1-yl group, or a 2-methoxycarbonylethene-1- Z represents a hydrogen atom or a halogen atom, and R represents a hydrogen atom or a 3-methyl-2-buten-1-yl group. However, the case where X is a -CHO group and Y, Z and R are hydrogen atoms at the same time is excluded. ] A plant growth regulator comprising one or more indole derivatives represented by the following as an active ingredient. (2) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, in the above formula, X represents a -CHO group, and Y represents a hydrogen atom, a halogen atom, a lower alkyl group, a phenyl group,
Pyridyl group, 3-hydroxy-3-methyl-1-buten-1-yl group or 2-methoxycarbonylethene-1
-yl group, Z represents a hydrogen atom, and R represents a 3-methyl-2-buten-1-yl group. ] An indole derivative represented by