JPS6146443B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a plant growth regulator containing a novel 1,2,4-triazole derivative as an active ingredient. The inventors have determined that the following formula: (wherein R ₁ has a lower alkenyl group, a benzyl group, or a halogen, trifluoromethyl, nitrile, lower alkyl, or lower alkoxy group as a substituent on a ring carbon atom and/or as a substituent on an α carbon atom) is a benzyl group having a lower alkyl group; R ₂ is a lower alkyl group; R ₃ is hydrogen or a methyl group) and 1,2,4-triazole derivatives that are acid addition salts or copper complex salts thereof. The present invention was established by newly synthesizing these 1,2,4-triazole derivatives and confirming that they have plant growth regulating activity. Therefore, the present invention provides a compound represented by the above formula () or an acid addition salt or copper complex salt thereof.
The present invention provides a plant growth regulator containing a 2,4-triazole derivative as an active ingredient. The plant growth regulating action of the active compounds of the invention includes, for example, a stunting or dwarfing action on the growth of woody and herbaceous monocots and dicots.
dwarfing effect). Such growth inhibition or dwarfing effects are useful, for example, in cereals and soybeans, where reduced stem growth may reduce the risk of lodging. Compounds that induce growth inhibition or dwarfing are also useful in limiting the growth of sugar cane, thereby increasing the sugar concentration in the cane at the time of harvest. Growth suppression in peanuts can enhance yield. Dwarfing turfgrass growth helps maintain it. Examples of suitable turfgrasses are Stenotaphrum secundatum;
Cynosurus (Cynosurus)
cristatus), Lolium multiflorum (Lolium
multiflorum), Lolium perenii (Lolium
perenne), Agrostis tenuis, Cynodon dactylon; Bermuda grass
grass)], Dactylis glomerata (Dactylis glomerata)
glomerata), Festuca spp., such as Festuca rubra, and Poa spp., such as Poa pratense. At least some of the active compounds of the invention suppress the growth of turfgrass without causing significant phytotoxicity and without adversely affecting the appearance (particularly the color) of the grass, so that such compounds are suitable for use in ornamental lawns and flower beds. Attractive for use on edges. Furthermore, the active compounds according to the invention may inhibit the growth of weeds present in turfgrass. Such weed species include, for example, Cyperus spp.
and dicotyledonous weeds. The growth of non-crop plants (such as weeds or cover plants) is inhibited, which may assist in the maintenance of farm and field crops. Plant growth regulating effects can be manifested in increased crop yield. Other plant growth regulating effects elicited by the active compounds of the invention include alteration of leaf angle and promotion of tillering in monocots. The former effect is useful, for example, in changing the orientation of potatoes' leaves, thereby allowing more light to fall on the crop and increasing photosynthesis and tuber weight. By promoting tillering of monocot crops (eg rice), the number of flowering shoots per unit area can be increased, thereby increasing the overall yield of such crops. Also, treatment of plants with the active compounds of the invention may result in leaves that take on a darker green color. Furthermore, the active compounds according to the invention can also inhibit sugar beet flowering and increase sugar yields. The active compounds according to the invention also make it possible to reduce the size of sugar beet without significantly reducing the sugar yield, thereby increasing the planting density. When the active compounds according to the invention are used for regulating the growth of plants, the application rate will depend on various factors, such as the particular compound selected and the type of plant whose growth is to be controlled, but will generally range from 0.1 to 15%; Preferably an application rate of 0.1 to 5 Kg/ha is used. However, for some plants, application rates within this range may have undesirable phytotoxic effects. Therefore, routine testing may be required to determine the best application rate of a particular compound for a particular purpose. The active compounds of the invention have also been found to have fungicidal, algicidal, antibacterial and antiviral activity as well as herbicidal activity. Although the active compounds of the present invention can be used alone for regulating plant growth, it is generally more convenient to formulate them into compositions. Therefore, the plant growth regulator of the present invention is usually provided in the form of a composition containing the compound of formula () or its acid addition salt or copper complex salt as an active ingredient together with a carrier or diluent. The active compounds of the invention of the formula (), their acid addition salts and copper complex salts can be applied in various ways, for example by applying them in unformulated or preferably formulated form to plants, seeds or their surroundings. By applying it locally, the purpose of regulating plant growth can be achieved either directly or by systemic action. The active compounds according to the invention or the compositions containing them can therefore be applied, for example, directly to the leaves of plants and also to shrubs and trees, seeds or the soil medium in which the plants, shrubs or trees are growing or to be planted. Alternatively, it can be applied by spraying or dusting or as a cream or paste preparation or in the form of steam. Application can be made to any part of the plant, shrub or tree, such as leaves, stems, branches, seeds, roots or the soil around the roots. As used herein, the term "plant" includes seedlings, shrubs and trees. The type of composition preferred as a plant growth regulator of the present invention will vary depending on the particular purpose intended. The composition comprises the active ingredient in a solid diluent or carrier such as kaolin, bentonite, diatomaceous earth, dolomite, calcium carbonate, talc, powdered magnesia,
It can be in the form of a repellent powder or granules mixed with Fuller's earth, gypsum, Hewitt's earth, diatomaceous earth and china clay.
Compositions for seed dressings may, for example, contain agents that promote adhesion of the composition to the seeds, such as mineral oil. The composition may also be in the form of a dispersible powder or granules containing a wetting agent to facilitate dispersion of the powder or granules in a liquid, such powders or granules further comprising fillers and suspending agents. may contain. Aqueous dispersions or emulsions are prepared by dissolving the active ingredient in an organic solvent which may contain wetting agents, dispersing agents or emulsifying agents and then adding the resulting mixture to water which may also contain wetting agents, dispersing agents or emulsifying agents. It can be prepared by Suitable organic solvents include ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, xylene, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol and glycol ethers such as 2-ethoxyethanol and −
butoxyethanol). Spray compositions can also be in the form of an aerosol, in which the formulation is held under pressure in a container in the presence of a propellant, such as fluorotrichloromethane or diglordifluoromethane. The compound can also be mixed in dry form with a pyrotechnic mixture to form a composition suitable for generating smoke containing the compound in a closed space. Alternatively, the compounds can be used in the form of microcapsules. suitable additives, e.g. spreading on the surface to be treated;
By incorporating additives to improve adhesion and rain resistance, various compositions can be better adapted to the various intended uses. The active compounds according to the invention can also be used in mixtures with fertilizers (eg nitrogen- or phosphorus-containing fertilizers). Preference is given to compositions consisting solely of fertilizer granules into which the compound has been incorporated, for example by coating. Such granules suitably contain up to 25% by weight of active compound. Furthermore, the compositions of the invention can be used as dipping or spray solutions, which are usually aqueous dispersions or emulsions containing the active ingredient in the presence of one or more wetting agents, dispersing agents, emulsifying or suspending agents. It can also be in the form of a liquid preparation. Such agents may be cationic, anionic or nonionic active agents. Suitable cationic activators are quaternary ammonium compounds such as cetyltrimethylammonium bromide. Suitable anionic active agents are soaps, salts of aliphatic monoesters of sulfuric acid, such as sodium lauryl sulfate, salts of sulfonated aromatic compounds, such as sodium, calcium or ammonium lignosulfonate, butylnaphthalene sulfonate and diisopropyl- and diisopropylene sulfonate. A mixture of the sodium salts of isopropyl-naphthalene sulfonic acid. Suitable nonionic surfactants are condensation products of ethylene oxide with aliphatic alcohols such as oleyl alcohol or cetyl alcohol or alkylphenols such as octylphenol, nonylphenol or octylcresol. Other nonionic surfactants are partial esters derived from long chain fatty acids and hexitol anhydride, condensation products of the partial esters with ethylene oxide, and lecithin. Suitable suspending agents are, for example, hydrophilic colloids (eg polyvinylpyrrolidone and sodium carboxymethylcellulose) and vegetable gums (eg acacia and tragacanth). Compositions used in the form of aqueous dispersions or emulsions are usually supplied in the form of concentrates containing a high proportion of the active ingredient and are diluted with water before use. Such concentrates often need to be capable of withstanding long-term storage and, when diluted with water after such long-term storage, to form an aqueous formulation that remains homogeneous long enough to be applied with conventional spray equipment. It is. Such concentrates conveniently contain up to 95% by weight, preferably 10% by weight or less.
It may contain up to 85% by weight of active ingredient, such as 25-60%. When diluted for the preparation of aqueous formulations, such formulations may contain varying amounts of active ingredient depending on their intended use, but generally 0.0005 (usually
Aqueous formulations containing from 0.01) to 10% by weight of active ingredient can be used. The compositions of the invention may further contain other biologically active compounds, such as gibberellins (e.g. GA ₃ ,
GA ₄ or GA ₇ ), auxins (e.g. indoleacetic acid or indolebutyric acid) and cytokinins (e.g. kinetin, diphenylurea, benzimidazole or benzyladenine) and other compounds with complementary fungicidal or insecticidal activity as well as stable agents such as epoxides such as epichlorohydrin. Other fungicidally active compounds are Septoria, Gibberella, Helminthosporium and sooty
grain complex (e.g. wheat)
It may be something that can control diseases on the panicles. Examples of such compounds are benomyl, carbendazole (BCM) and captafol.
It is. Other fungicidally active compounds may also be capable of controlling diseases growing on seeds and soil; examples of such compounds are Maneb and Captan. Although the active compounds of the invention of formula () have asymmetric centers and are generally obtained in racemic form, such ceramic forms and other mixtures can be isolated by methods known in the art, e.g. chromatography. Can be separated into isomers. In many cases, compounds can be prepared stereospecifically in single diastereomeric forms. The lower alkyl group in the definition of formula () above can be straight-chain or branched, preferred examples thereof being methyl, ethyl, propyl (n- or iso-propyl), butyl (n-, iso- or t
-butyl). Preferred lower alkenyl groups (which may also be straight or branched) are alkyl groups. As mentioned above, the benzyl group has its OH ₂ unit and/or
or may be substituted on the phenyl unit. Examples of suitable substituents on phenyl units include chloro, dichloro, trichloro, pentachloro, fluoro, difluoro, bromo, dibromo, methyl, dimethyl, nitro, trifluoromethyl, methoxy groups. A preferred substituent on the CH ₂ unit is a methyl group. Particularly preferred compounds of formula () include _allyl , benzyl, α-methyl-p-chlorobenzyl, α-methyl-2,4-dichlorobenzyl, α
-Methyl-p-fluorobenzyl, o-, m- or p-chlorobenzyl, 2,4-, 3,4- or 2,6-dichlorobenzyl, 2,4,5- or 2,3,6-trichloro Benzyl, pentachlorobenzyl, m- or p-bromobenzyl, 2.4
-dibromobenzyl, o-, m- or p-fluorobenzyl, 2,4-difluorobenzyl, o-
or p-methylbenzyl, 2,5-dimethylbenzyl, p-nitrobenzyl, m-(trifluoromethyl)benzyl, o- or p-methoxybenzyl, 3-nitro-4-chlorobenzyl, 2-chloro-4- Fluorobenzyl, 2-fluoro-4-
Bromobenzyl or 2-methoxy-5-bromobenzyl, R ₂ is isopropyl or t-
A compound which is butyl and R ₃ is hydrogen or methyl. Suitable acid addition salts of compounds of formula () are salts with inorganic or organic acids, such as hydrochloric acid, nitric acid, sulfuric acid, toluenesulfonic acid, acetic acid or oxalic acid. Copper complex salts have the following general formula: In the formula, R ₁ , R ₂ and R ₃ have the above meanings, and A
represents an anion (eg chlorine, bromine, iodine, nitrate, sulfate or phosphate anion), n is 2 or 4 and y is 0 or an integer from 1 to 12. Specific examples of active compounds of the invention are shown in the table.

【table】

【table】

[Table] +This compound has the following structural formula: It is in the form of a copper complex salt that is thought to have . °Nuclear magnetic resonance spectroscopy reveals compound 21,
23, 24 and 32 are each in the form of a mixture containing two stereoisomers in the following weight ratios. Compound Weight ratio 21 9:1 23 7:1 24 4:1 32 1.5:1 The acetate ester of compound 1 (compound 43) has a melting point
Produced in impure form with a temperature of 125-128°C. In addition, 2-methylbutyric acid ester of compound 1 (melting point 129-
131℃) was also produced. This compound has the structure of the following formula. A compound or a salt thereof in which R ₃ is hydrogen in formula () has the following formula: (In the formula, R ₁ and R ₂ have the above-mentioned meanings) or a salt thereof, preferably at 0 to 100°C for 1 to 12
It can be produced by time reduction. Suitable reducing agents are sodium borohydride, lithium aluminum hydride or aluminum isopropoxide. If desired, reduction can also be achieved by catalytic hydrogenation using a suitable metal catalyst. If the compound of formula () is a sterically hindered ketone, a Grignard reagent such as butylmagnesium halide (eg bromide or iodide) can be used as reducing agent. When using reagents such as butylmagnesium halide, single diastereomers are often produced. Reduction can be carried out by dissolving the reactants in a solvent such as diethyl ether or tetrahydrofuran (for example, in the case of lithium aluminum hydride reduction) or a hydroxyl-based solvent (for example, in the case of sodium borohydride reduction). The reaction temperature depends on the reactants and solvent used, but
Generally the reaction mixture is heated under reflux. The post-reaction product can be isolated by acidification with a dilute inorganic acid followed by extraction with a convenient solvent. After removal of the solvent in vacuo, the product can be crystallized from a suitable solvent. For a compound or a salt thereof in which R ₃ is a methyl group in formula (), a compound of formula () or a salt thereof and a suitable Grignard reagent, such as methylmagnesium halide such as methylmagnesium bromide or iodide, are preferably used in a reaction mixture of 15 to 80 ℃6
It can be produced by reacting for ~12 hours. This reaction can be carried out by methods known per se. The starting material of formula () is 1,2,4-triazole or its salt, which is represented by the following formula: α of (wherein X is halogen, preferably bromine or chlorine, and R ₁ and R ₂ have the meanings given above)
-Can be produced by reaction with haloketones. Although this process can be carried out by simply heating the reactants in the absence of a solvent or diluent, the presence of a solvent is preferred. Suitable solvents are non-hydroxyl solvents such as acetonitrile, dimethylformamide, dimethylsulfoxide, sulfolane and tetrahydrofuran. Hydroxylating solvents such as methanol and ethanol can also be used if the presence of hydroxyl groups does not prevent the reaction from proceeding. The process can also be carried out in the presence of a base such as sodium hydride, sodium ethoxide, excess 1,2,4-triazole or an alkali metal carbonate (e.g. potassium carbonate). The reaction temperature depends on the choice of reactants, solvent and base, but generally the reaction mixture is heated under reflux. Generally, this method involves dissolving the reactants in a solvent;
This can be carried out by allowing the reaction to occur and then isolating the product by vacuum distillation of the solvent. Unreacted triazole is extracted with a suitable solvent and then removed by washing with water. Crystallization or other purification measures (eg chromatography) can then be carried out if desired. The α-halogen raw material can be produced by any known method described in the literature. The compound of formula () or its salt is the following formula: It can also be produced by alkenylating or benzylating a compound (wherein R ₂ has the above-mentioned meaning). Details of this reaction are described in German Offenlegungsschrift No. 2610022. Acid addition salts, copper complex salts, ethers and esters of the compound of formula () can be produced from the compound of formula () by known methods. For example, copper complex salts can be prepared by reacting an uncomplexed compound with a copper salt in a suitable solvent. Next, production examples of the active compounds of the present invention will be shown. Production example 1 1-t-butyl-2-(1,2,4-triazol-1-yl)-2-p-chlorobenzylethanol (compound 1) Step 1,2,4-triazole (33.4 g) and sodium Ethoxide (prepared from 11.6 g of sodium and 250 ml of ethanol) was refluxed for 1 hour.
Bromopina cologne (87 g) was added to this solution at reflux temperature.
was added and heating continued for an additional 2 hours. The mixture was then cooled to room temperature, the precipitated sodium bromide was removed by filtration, and the solvent was distilled off in vacuo. The residue was extracted with chloroform (100ml) and the extract was washed with water (7 x 15ml), dried over sodium sulfate and filtered. Then petroleum ether (boiling point 60-80
°C) and concentrate the solution to obtain α-1, 2, 4-
Triazol-4-yl-pinacolone (melting point 176
°C) was obtained. The solution was further concentrated to obtain α-1,2,4-triazol-1-yl-pinacolon having a melting point of 63-65°C. Step α-1 in dimethylformamide (20 ml)
2,4-triazol-1-yl-pinacolone (3.3 g) was dissolved in sodium hydride (0.48 g; 100%).
was added dropwise with stirring at room temperature to a suspension of p-chlorobenzyl chloride (3.2 g) in dimethylformamide (2-3 ml) dropwise after stirring for 2 hours. The reaction mixture was kept at 5-10°C for 2 hours. The solvent was then removed in vacuo and water was added to the residue. This aqueous solution was extracted with dimethylene chloride, and the organic layer was washed with water, dried over magnesium sulfate, and the solvent was removed. The crystallization of the resulting yellow solid yields α-p with a melting point of 122-123°C.
-Chlorobenzyl-α-1,2,4-triazol-1-yl-pinacolone was obtained as a white crystalline solid. Process Step product (2.0g) methanol (20
ml) solution in small portions with sodium borohydride (0.26 ml).
g). The reaction mixture was then refluxed for 1 hour, the solvent was distilled off in vacuo, and 1N hydrochloric acid (40ml) was added to the residue.
was added. The white precipitate formed was separated, washed with water, dried and crystallized from aqueous ethanol to give the title compound as a white crystalline solid with a melting point of 162-164°C. The starting materials for the process can also be obtained by the following alternative methods. Process 4-chlorobenzaldehyde (140.5 g) and napicolone (100 g) in industrial grade methylated spirits (IMS; 200 ml) were mixed with water (70 ml) and IMS (150 ml).
The solution was added dropwise over 25 minutes to sodium hydride (40 g) in 25 mL of water while keeping the temperature below 25° C. by external cooling with ice water. The resulting creamy suspension was heated to 18°C.
The mixture was stirred for an additional 3 hours and then filtered. The residue was washed with aqueous IMS and dried to give 4-chlorobenzalpina cologne with a melting point of 83-84°C. The liquid was concentrated under reduced pressure and allowed to stand for 2 days to further obtain the chalcone product with a melting point of 83-84°C. Process: Add the above chalcone (22.25g) to ethyl acetate (125g).
After washing with ethyl acetate (4 x 15 ml) Raney nickel (6 g) was added. The apparatus was evacuated with a water pump and hydrogen gas was introduced until atmospheric pressure was reached. The mixture was then shaken vigorously at room temperature and the hydrogenation was stopped after 14.5 hours. At this time, the amount of hydrogen gas absorbed was 2303 ml. The catalyst was then carefully separated to avoid drying the residue, and the liquid was concentrated in vacuo to yield crude 4-chlorobenzylpinacolone. Process 4-Chlorobenzylpinacolone (11.2 g) in carbon tetrachloride (80 ml) was cooled to approximately 5°C and bromine (8 g) in carbon tetrachloride (20 ml) was added dropwise at this temperature over a period of 2 hours. Care was taken to keep free bromine in the reaction mixture to a minimum to avoid the formation of by-products. The solution was then washed with saturated aqueous sodium bicarbonate, water, dried over magnesium sulfate, and concentrated in vacuo to give the crude 1-(4'-chlorophenyl)-2-bromo-4,4'-dimethylpentane- 3-one was obtained as a white crystalline solid with a melting point of 48-50°C. Step The product of step (0.69 g) and 1,2,4-triazole (0.17 g) were mixed with potassium carbonate (0.52 g) in acetone (10 ml) and the mixture was refluxed for 2 hours. After cooling to room temperature, the inorganic substances were separated and the liquid was concentrated in vacuo to obtain the crude α-p-
Chlorobenzyl-α-1,2,4-triazol-1-yl-pinacolone was obtained. Production Example 2 1-t-Butyl-2-(1,2,4-triazol-1-yl)-2-benzylethanol (Compound 2) Step Pinacolone (10 g) in dry diethyl ether (30 ml) was dissolved in dry diethyl ether. was added slowly to a suspension of soda amide (41 g) in (15 ml).
The resulting mixture was stirred at room temperature overnight and then refluxed with stirring for 16 hours. (At this point the mixture turned orange). Benzyl chloride (13.2 g) was then added dropwise and the mixture was refluxed for 24 hours. Water (100ml) was added, and the ether layer was separated, washed with water, diluted hydrochloric acid, then water, and dried with sodium sulfate. The ether was distilled off under reduced pressure, and the residue was distilled to a boiling point of 78-80℃/
α-Benzylpinacolon of 0.06 mmHg was obtained. Process Bromine (1.4 ml) was added dropwise to α-benzylpinacolone (5.2 g) in diethyl ether (80 ml) at about 10°C. The solution was stirred at room temperature for 1 hour and the ether was removed in vacuo to give a red liquid. This was bulb distilled to obtain α-bromo-α-benzylpinacolone as a slightly colored liquid with a boiling point of 100°C/0.1 mmHg. Step 1, 2, 4 in dimethylformamide (5 ml)
- triazole (0.28 g) in dimethylformamide (2 ml) with sodium hydride (100%; 0.1
g) was added dropwise to the suspension. The reaction mixture was stirred for 2 hours and then treated with dimethylformamide (5 ml).
α-Bromo-α-benzylpinacolon (1.0
g) was added. The reaction mixture was stirred at room temperature overnight and then water (75 ml) was added to give a melting point of 69-71 °C.
α-(1,2,4-triazol-1-yl)-
α-Benzylpinacolon was obtained as a white crystalline solid. Process α-(1,2,4-triazol-1-yl)-α-benzylpinacolone (2.0 g) in methanol (20 ml) was treated with sodium borohydride (0.26 g) in small portions, resulting in a mixture was refluxed for 1 hour. The mixture was then distilled off in vacuo and the residue was diluted with 1N
Hydrochloric acid (40ml) was added. The white precipitate formed was separated, washed with water and dried to give the title compound as a white crystalline solid which was crystallized from aqueous ethanol. Production example 3 1-(1,2,4-triazol-1-yl)-
1-p-fluorobenzyl-2-t-butyl-
Propan-2-ol (Compound 4) An ethereal solution of methylmagnesium iodide prepared by reacting methyl iodide (6.2 g) with magnesium (1.1 g) in dry diethyl ether was dissolved in α in dry diethyl ether (30 ml). -1・
Treated portionwise with 2,4-triazol-1-yl-α-p-fluorobenzyl-pinacolone (4.0 g). The resulting mixture was refluxed for 1 hour, then cooled and treated with 10% sulfuric acid (20ml). The insoluble material was separated off, washed with dilute hydrochloric acid and then with water, and dried to give the title compound after crystallization from aqueous ethanol. Production Example 4 1-t-Butyl-2-(1,2,4-triazol-1-yl)-2-p-chlorobenzylethanol (Compound 5) Butyl bromide (5.63 g) and magnesium (1.0
g) in dry diethyl ether, a solution of butylmagnesium bromide prepared by reacting with
It was treated portionwise with triazol-1-yl-α-p-chlorobenzyl chloride (4.0 g) and the resulting mixture was refluxed for 1 hour. The reaction mixture was then treated with dilute sulfuric acid (20ml) and the ether layer was separated, washed with water and dried over sodium sulfate. The white solid obtained by evaporation of the solvent in vacuo was crystallized from diethyl ether/petroleum (boiling point 60-80°C) to give the title compound. Production Example 5 Copper complex salt of the compound of Production Example 1 (Compound 20) Cupric chloride (0.9 g; dissolved in water (4 ml))
0.005 mol) of compound 1 in ethanol (60 ml)
(2.9 g; 0.01 mol) and the resulting green solution was stirred for 30 minutes. Then reduce the volume of solvent to approx.
It was reduced by 30ml and water (30ml) was added and a green oil separated. The aqueous layer was removed by decantation and the organic layer was stirred with isopropanol (50ml) for 30 minutes. The resulting green solid was separated, dried and crystallized from ethanol/water to give the title compound (1.6g).
I got it. All the compounds shown in the table above are from Production Example 1.
It was manufactured according to the method described in 5 to 5. Next, various compositions according to the present invention will be explained by giving Examples. Example 1 Wettable powder compound 1 50w/w% Aerosol OT 2 Polyfon H 5 Porcelain 43 Example 2 Emulsifying concentrate compound 1 100g/Amine dodecylbenzenesulfonate 400g/2-n-butoxy ethanol Example 3 Aqueous suspension compound 1 250 g/Polyphon H 25 Bentonite 15 Polysaccharide 0.75 Water Example 4 Powder compound 1 5w/w% china clay 98 Example 5 Granule compound 1 5w/w% powder 5 china clay 90 Example 6 Organic solution compound 1 200g/dimethylformamide Up to 1 Next, the plant growth regulating activity of the active compound of the present invention will be explained with reference to test examples. Test Example The test compound is prepared in the form of a 5000 ppm solution in diluted water and the solution is then applied to seedlings of wheat, barley, corn, rice, Lolium ryegrass, soybean, cotton, lettuce, Mung beans and kidney beans. It was applied to the leaves of. The test was repeated twice and evaluated for plant growth regulating effects and signs of phytotoxicity 21 days after treatment. The table shows the inhibitory effects of test compounds on plant growth using the following grades: 0 = Inhibition rate 20% or less 1 = 〃 21-40% 2 = 〃 41-60% 3 = 〃 61- 80% In the table, blank areas indicate that the compound was substantially inactive as a growth inhibitor. The associated plant growth regulating effects are indicated by the following symbols: G = darker green color of leaves A = tip growth action T = tillering action In the table, the symbol "-" indicates that no test was conducted. The asterisk (*) indicates that the test compound was applied at 4000 ppm.

【table】

【table】

Claims (1)

[Claims] 1. As an active ingredient, the following formula: (wherein R ₁ has a lower alkenyl group, a benzyl group, or a halogen, trifluoromethyl, nitro, lower alkyl, or lower alkoxy group as a substituent on a ring carbon atom and/or as a substituent on an α carbon atom) is a benzyl group having a lower alkyl group; R ₂ is a lower alkyl group; R ₃ is hydrogen or a methyl group), or a 1,2,4-triazole derivative that is an acid addition salt or copper complex salt thereof. Contains plant growth regulators. 2 In formula (), R ₁ is a benzyl group having up to 3 halogens as ring substituents, and R ₂
The plant growth regulator according to claim 1, wherein is a t-butyl group, and _R3 is hydrogen or a methyl group. 3 In formula (), R ₁ is allyl, benzyl,
α-Methylbenzyl, α-methylchlorobenzyl, α-methyldichlorobenzyl, α-methylfluorobenzyl, chlorobenzyl, dichlorobenzyl, trichlorobenzyl, pentachlorobenzyl, bromobenzyl, dibromobenzyl, fluorobenzyl, difluorobenzyl, methylbenzyl The plant growth regulator according to claim 1, which is dimethylbenzyl, nitrobenzyl, trifluoromethylbenzyl, methoxybenzyl, chloronitrobenzyl, chlorofluorobenzyl, fluorobromobenzyl, or methoxybromobenzyl. 4 In formula (), R ₁ is allyl, benzyl,
α-methyl-p-chlorobenzyl, α-methyl-
2,4-dichlorobenzyl, α-methyl-p-fluorobenzyl, o-, m- or p-chlorobenzyl, 2,4-, 3,4- or 2,6-dichlorobenzyl, 2,4,5- or 2,3,6-trichlorobenzyl, pentachlorobenzyl, m- or p-bromobenzyl, 2,4-dibromobenzyl, o-, m- or p-fluorobenzyl, 2.
4-difluorobenzyl, o- or p-methylbenzyl, 2,5-dimethylbenzyl, p-nitrobenzyl, m-(trifluoromethyl)benzyl, o- or p-methoxybenzyl, 3-nitro-4-chlorobenzyl , 2-chloro-4-fluorobenzyl, 2-fluoro-4-bromobenzyl, or 2-methoxy-5-bromobenzyl. 5 The active ingredient is 1-(R・S)-t-butyl-2-
(R.S)-(1.2.4-triazol-1-yl)-2-p-chlorobenzylethanol, 1-
(S・R)-t-butyl-2-(R・S)-(1・
2,4-triazol-1-yl)-2-p-chloro-benzylethanol, 1-(R·S)-t-
Copper complex salt of butyl-2-(R・S)-(1.2.4-triazol-1-yl)-2-p-chlorobenzylethanol, 1-t-butyl-2-(1.
2,4-triazol-1-yl)-2-benzylethanol, 1-t-butyl-2-(1,2,
4-triazol-1-yl)-2-p-fluorobenzylethanol, 1-t-butyl-2-
(1,2,4-triazol-1-yl)-2-
(2',4'-dichlorobenzyl)ethanol, 1-
t-Butyl-2-(1,2,4-triazole-
1-yl)-2-p-bromobenzylethanol, 1-t-butyl-2-(1,2,4-triazol-1-yl)-2-(2'-chloro-4'-fluorobenzyl)ethanol , 1-t-butyl-2
-(1,2,4-triazol-1-yl)-2-
o-methoxybenzylethanol, 1-t-butyl-2-(1,2,4-triazol-1-yl)-2-o-methylbenzylethanol or 1
The plant growth regulator according to claim 1, which is -t-butyl-2-(1,2,4-triazol-1-yl)-2-p-methylbenzylethanol. 6. The plant growth regulator according to any one of claims 1 to 5, which is in the form of granules.