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WO1999045774A1 - Agent regulant la croissance de vegetaux - Google Patents

Agent regulant la croissance de vegetaux Download PDF

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Publication number
WO1999045774A1
WO1999045774A1 PCT/JP1999/001181 JP9901181W WO9945774A1 WO 1999045774 A1 WO1999045774 A1 WO 1999045774A1 JP 9901181 W JP9901181 W JP 9901181W WO 9945774 A1 WO9945774 A1 WO 9945774A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
ethylene
phenyl
methoxy
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1999/001181
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English (en)
Japanese (ja)
Inventor
Hiroshi Kousaka
Kou Ishii
Takamitsu Eshima
Yoshiharu Hayashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Snow Brand Seed Co Ltd
Asahi Chemical Industry Co Ltd
Original Assignee
Snow Brand Seed Co Ltd
Asahi Chemical Industry Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Snow Brand Seed Co Ltd, Asahi Chemical Industry Co Ltd filed Critical Snow Brand Seed Co Ltd
Priority to AU27475/99A priority Critical patent/AU2747599A/en
Publication of WO1999045774A1 publication Critical patent/WO1999045774A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Definitions

  • the present invention relates to a plant growth regulator having a high rooting promoting activity of a plant and useful as an agricultural chemical or a fertilizer additive.
  • plant roots absorb various water and nutrients necessary for growth, support the above-ground parts to prevent lodging, and supply plant hormones essential for healthy plant growth to the above-ground parts. It is known to have important functions. [Wai s e 1 et al., Ed., Plan Root s—The Hidden Ha 1 f— (1991)]. Also, especially in transplantation cultivation, it is important to grow seedlings that have a large root mass during the seedling raising stage and quickly root after planting. From these facts, the importance of sufficiently developing the roots of plants in the field of agriculture has been pointed out for a long time [B 00 te et al., Physiology and
  • auxin-based compounds such as indolebutyric acid, naphthylacetic acid, and naphthyl acetoamide, which have been put into practical use as rooting promoters, depend on the type and condition of the plant and the concentration to be applied. This may have undesired effects such as epinasal growth of leaves, twisting and cracking of stems, and even death. For this reason, during general seedling raising, the method of use and amount used are limited, and the effect of promoting root development has not been sufficiently satisfactory.
  • the present inventors have conducted intensive studies to solve such problems, and as a result, surprisingly, the compound represented by the following general formula (1) substantially shows almost no side effects such as leaf upgrowth. And found that the plant has high root-promoting activity, and based on this finding, completed the present invention.
  • Ar represents a phenyl group which may have a substituent
  • A represents a linear or branched lower alkylene group
  • B represents a linear or branched lower alkylene group or lower.
  • R 1 is a hydroxyl group, an amino group or a lower alcohol.
  • a plant growth regulator comprising a compound represented by the formula or a salt thereof as an active ingredient.
  • the present invention also provides a composition for regulating plant growth comprising the compound represented by the general formula (1) or a salt thereof, and a carrier for agricultural chemicals or a carrier for fertilizer.
  • the present invention still further provides use of the compound represented by the general formula (1) or a salt thereof for producing a plant growth regulator.
  • plant growth regulator The active ingredient (hereinafter referred to as “plant growth regulator”) of the plant growth regulator of the present invention is a compound represented by the above general formula (1) or a salt thereof.
  • the phenyl group which may have a substituent represented by Ar includes, for example, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group and a lower alkoxyl group on the benzene ring.
  • a fuunyl group which may be substituted by 1 to 5 groups selected from The group represented by Ar is represented by the general formula (2).
  • R 2 , R 3 , R 4 , R 5 and R 6 are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group, or a lower alkoxyl group.
  • the lower alkyl group is a methyl group, an ethyl group, an n-propyl group, an n- Alkyl groups having 1 to 6 carbon atoms such as butyl, n-pentyl, n-hexyl, i-propyl, i-butyl, i-pentyl and i-hexyl Of these, a methyl group is particularly preferred.
  • the lower alkoxyl group includes methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, i-propoxy, i-butoxy, and i-pentyloxy.
  • an alkoxyl group having 1 to 6 carbon atoms such as an i-hexyl group or a methoxy group.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • substitution position may be in the 2 to 6 position or may be shifted, but is preferably in the 2 position, 3 position and Z or 4 position.
  • More preferred Ar is a phenyl group which may be substituted with a group selected from a halogen atom, a hydroxyl group, a nitro group, a methyl group and a methoxy group at the 2-, 3- and Z- or 4-positions. .
  • A is a linear or branched lower alkylene group, for example, an alkylene group having 1 to 6 carbon atoms such as a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a pentamethylene group and a hexamethylene group.
  • a linear alkylene group having 1 to 4 carbon atoms is preferable.
  • B is a linear or branched lower alkylene group or a lower alkylene group, and examples of the lower alkylene group are the same as those described above.
  • the lower alkenylene group examples include an alkenylene group having 2 to 6 carbon atoms such as a vinylene group, a probenylene group, a butenylene group, a pentenylene group and a hexenylene group.
  • the lower alkylene group is preferably a linear one having 1 to 4 carbon atoms.
  • the lower alkylene group is preferably a straight chain having 2 to 4 carbon atoms.
  • R 1 is a hydroxyl group, an amino group or a lower alkoxyl group, and examples of the lower alkoxyl group are the same as those described above.
  • R 1 is preferably a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoquine group, or an amino group.
  • the salt of the compound represented by the general formula (1) include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt, inorganic base salts such as ammonium salt, and triethylamine. Salt, pyridine salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt,
  • Ar is phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-hydroxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl , 4 monophenyl, 2-chlorophenyl, 3-chlorophenyl or 3,4-dichlorophenyl,
  • A is a linear alkylene group having 1 to 4 carbon atoms
  • B is 1 to 4 carbon atoms.
  • a linear alkylene group of 4 or a linear alkylene group having 2 to 4 carbon atoms and may be a hydroxyl group, an amino group, a methoxy group, an ethoxy group, an n-propoxy group or an i-propoxy group. preferable.
  • Ar is a phenyl group, a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-fluorophenyl group, a 4-chlorophenyl group, a 4-bromophenyl group, a 4-iodophenyl group, a 2-chlorophenyl group, or a 3-chlorophenyl group.
  • A is a linear alkylene group having 1 to 4 carbon atoms
  • B is a linear alkylene group having 1 to 4 carbon atoms or It is a straight-chain alkylene group
  • R 1 is a hydroxyl group, a methoxy group, an ethoxy group, an n-propoxy group or an i-propoxy group.
  • Ar, A, B and R 1 force, 4-methylphenyl group, ethylene group, ethylene group and hydroxyl group; 4-methoxyphenyl group, ethylene group, ethylene group and hydroxyl group; 4-chlorophenyl group , Ethylene group, ethylene group and hydrid Methyl xyl group; phenyl group, methylene group, ethylene group and hydroxy group; phenyl group, trimethylene group, ethylene group and hydroxy group; phenyl group, ethylene group, methylene group and hydroxy group; phenyl group, ethylene Phenyl, ethylene, cis-vinylene and hydroxy groups; phenyl, ethylene, trans-vinylene and ethoxyquin groups; phenyl, ethylene, ethylene and hydroxy groups Groups; phenyl, ethylene, ethylene and methoxy; phenyl, trimethylene, ethylene and methoxy; phenyl, tetramethylene, ethylene and
  • plant growth regulator examples include the following. 4 Oxo— 4 [[2- (4-Tolyl) ethyl] amino] Monobutyric acid
  • B-The plant growth regulator used in the present invention can be produced, for example, by the following method.
  • R 1 — 1 is a protecting group for a hydroxyl group, an amino group or a carboxyl group.
  • X represents a hydroxyl group, and together with CO—, an acid halide, . an active ester, can be coupled to form a reactive derivative of the force Rupon acids such SanRyo disilazide X 'is chlorine, R 1 represents a halogen atom such as bromine - shows the 2 lower alk kill group).
  • Compound (a) is a salt with an inorganic acid such as hydrochloride, hydrobromide, hydrobromide, sulfate, perchlorate, phosphate, nitrate or carbonate, acetate, It may be a salt with an organic acid such as oxalate, maleate, fumarate, succinate, methanesulfonate, ethanesulfonate, and toluenesulfonate.
  • an inorganic acid such as hydrochloride, hydrobromide, hydrobromide, sulfate, perchlorate, phosphate, nitrate or carbonate, acetate
  • organic acid such as oxalate, maleate, fumarate, succinate, methanesulfonate, ethanesulfonate, and toluenesulfonate.
  • the compound (c-11) may be a salt with the above-mentioned acid or base.
  • compound (a) and compound (b) are converted into an inert medium, for example, a ketone solvent such as acetone or methyl ethyl ketone, or an ether such as getyl ether, 1,4-dioxane, or tetrahydrofuran.
  • Organic solvents organic solvents such as chloroform, methylene chloride, ethylene chloride, etc .; non-protonic polar solvents such as N, N-dimethylacetamide, dimethylsulfoxide, N, N-dimethylformamide
  • the compound (c-11) can be synthesized by reacting in an aromatic solvent such as benzene, toluene or the like.
  • the molar ratio of the compound (a) to the compound (b) is preferably, for example, 0.5 to 5: 1.5 to 0.5, and the concentration is not particularly limited as long as it is a concentration that can react. However, for example, the concentration is preferably 1 to 30% (W / V), particularly preferably the compound concentration is 5 to 20% (W / V). Under such conditions, for example, the reaction may be stirred at 0 to 60 ° C. for 5 minutes to 24 hours.
  • the compound (a) is a salt
  • the compound (a) may be desalted in advance with an acid binder described below.
  • compound (d) is an active ester, for example, cyano methyl ester, phenyl thioester, p-ditrophenyl thioester, methanes phonate, benzenesulfonate, toluenesulfonate, p-diester Trophenyl ester, 2,4-dinitrophenyl ester, 2,4,5-trichlorophenyl ester, 2,4,6-trichlorophenyl ester, pen phenyl ester, N-hydroxysuccinate Acid imidoester, Examples include N-hydroxyphthalic acid imido ester, 1H-1-hydroxybenzotriazole ester, 8-hydroxyquinoline ester, N-hydroxypiperidine ester, and the like.
  • active ester for example, cyano methyl ester, phenyl thioester, p-ditrophenyl thioester, methanes phonate, benzenesulfonate,
  • Protecting group R 1 - 1 is not particularly limited as long as it forms a carboxyl group with solution hydrolysis min in dilute Al force Li or acidic solution, for example, main butoxy group, an ethoxy group, a propoxy group, isopropoxy And a lower alkoxy group such as a butoxy group, an Ibutoxy group, a pentyloxy group, and a hexyloxy group, and an aralkyloxy group such as a benzhydryl group. These protecting groups may be R.
  • a known acid azide method may be used.
  • the compound (c-12) can be synthesized by reacting with a dehydrating condensing agent such as minopropyl) amide.
  • a dehydrating condensing agent such as minopropyl
  • the compound (a) may be desalted in advance with an acid binder described below.
  • the compound (c-12) can be synthesized by reacting the compound (d) with the compound (a) in the presence of an acid binder described below.
  • Solvents used in this method include, for example, organic chlorinated solvents such as methylene chloride and chloroform, ether solvents such as dimethyl ether and tetrahydrofuran, aromatic solvents such as benzene and toluene, and heterocyclic rings such as pyridine. And aprotic polar solvents such as N, N-dimethylformamide, NN-diethylacetamide, and dimethylsulfoxide. Of these, pyridine is the most preferred. When a solvent other than pyridine is used, organic bases such as triethylamine, triptylamine, dimethylamine, and pyridine are used as acid binders, calcium carbonate, sodium carbonate, and sodium hydroxide. An inorganic base such as lime can be used.
  • organic chlorinated solvents such as methylene chloride and chloroform
  • ether solvents such as dimethyl ether and tetrahydrofuran
  • aromatic solvents such as benzene and toluen
  • the compound (d) may be, for example, The reaction may be carried out using 1.5 times the molar amount of a dehydrating condensing agent. After completion of the reaction, if R is the above-mentioned protecting group, hydrolysis treatment is preferably performed at room temperature or under heating for 30 minutes to 8 hours under alkaline conditions using, for example, 1 to 10 N NaOH or KOH. Then, it may be neutralized with concentrated hydrochloric acid.
  • the reaction solution obtained in Production Method 1 or 2 is cooled appropriately to precipitate and recover the target substance, and further, water or a solubilized organic solvent such as acetone, methanol, ethanol, dimethyl sulfoxide, N
  • a solubilized organic solvent such as acetone, methanol, ethanol, dimethyl sulfoxide, N
  • the desired product can be obtained by recrystallization from a single or mixed solvent such as N, N-dimethylformamide, chloroform, methylene chloride, ethylene chloride, benzene, and toluene.
  • the reaction solution is extracted by adding a product-soluble organic solvent which is not mixed with water and further water, and then the organic solvent layer is extracted with a dilute acidic aqueous solution such as 1 After washing with a 5N aqueous hydrochloric acid solution and then with water, further washing with an alkaline aqueous solution, for example, a saturated aqueous solution of sodium carbonate, finally washing with water sequentially, drying and evaporating the solvent, if necessary, It can be obtained by recrystallization from a single or mixed solvent or purification by silica gel gel chromatography using a single or mixed solvent.
  • the compound (c— 3) can be obtained.
  • the initial concentration of the compound (c-11) is not particularly limited, but is preferably, for example, 1 to 20% by weight, particularly preferably 5 to 10% by weight.
  • the compound (c-13) may be a salt with the above-mentioned acid or base.
  • the reaction solvent is distilled off, the product-soluble organic solvent immiscible with water and water are added, and the organic solvent layer is collected, and then an aqueous alkaline solution, for example, saturated After washing with an aqueous solution of sodium carbonate, followed by washing with water and drying, the organic solvent is distilled off, and then, if necessary, recrystallization from a single solvent or a mixed solvent.
  • the compound (c-11) is used as a raw material and, for example, an equimolar amount or more of thionyl chloride is used for a reaction at room temperature for 5 to 30 minutes with stirring. After the reaction, the thionyl chloride is distilled off to obtain a compound (e). . Then, the reaction mixture is added to aqueous ammonia in an organic solvent such as an inert organic solvent such as acetone, dimethyl sulfoxide, N, N-dimethylformamide, chloroform, methylene chloride, ethylene chloride, benzene, and toluene.
  • an organic solvent such as an inert organic solvent such as acetone, dimethyl sulfoxide, N, N-dimethylformamide, chloroform, methylene chloride, ethylene chloride, benzene, and toluene.
  • the initial concentration of the compound (c-11) is not particularly limited, but is preferably, for example, 1 to 20% (W / V), particularly preferably 5 to 10% (W / V).
  • the initial concentration of the compound (e) in aqueous ammonia is not particularly limited, but is preferably, for example, 1 to 25% by weight, particularly preferably 4 to 15% by weight.
  • the compound (c-14) may be a salt with the above-mentioned acid or base.
  • the plant growth regulator and the composition for regulating plant growth of the present invention may contain one or more of the above-mentioned plant growth regulators or salts thereof.
  • the plant growth regulator and the composition for regulating plant growth of the present invention may be the above-described plant growth regulator itself, or a carrier acceptable as a carrier for agricultural chemicals or fertilizers such as wettable powders, emulsions, granules, and powders. May be blended.
  • solid carriers include mineral powders (such as kaolin, bentonite, clay, montmorillonite, talc, clay, mica, vermiculite, Secco, calcium carbonate, phosphorous lime, etc.) and vegetable powders (soybean Flour, wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc., high molecular compounds (petroleum resin, polychlorinated vinyl, ketone resin, etc.), and alumina, waxes, etc. can be used.
  • mineral powders such as kaolin, bentonite, clay, montmorillonite, talc, clay, mica, vermiculite, Secco, calcium carbonate, phosphorous lime, etc.
  • vegetable powders such as kaolin, bentonite, clay, montmorillonite, talc, clay, mica, vermiculite, Secco, calcium carbonate, phosphorous lime, etc.
  • vegetable powders such as kaolin, bentonite, clay, montmorillonite
  • liquid carrier examples include alcohols (such as methanol, ethanol, butanol, ethylene glycol, and benzyl alcohol), aromatic hydrocarbons (such as benzene, benzene, and xylene), and chlorine. Hydrocarbons (chloroform, carbon tetrachloride, monochlorobenzene, etc.), ethers (dioxane, tetrahydrofuran) ), Ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, etc.), acid amides (N, N-dimethylacetamide, etc.), ether alcohols ( For example, ethylene glycol monoethyl ether) or water can be used.
  • alcohols such as methanol, ethanol, butanol, ethylene glycol, and benzyl alcohol
  • aromatic hydrocarbons such as benzene, benzene, and
  • any of nonionic, anionic, cationic and zwitterionic can be used.
  • surfactants that can be used in the present invention include: polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene rubitane fatty acid ester, Oxyethylene polymer, oxypropylene polymer, polyoxyethylene alkyl phosphate, fatty acid salt, alkyl sulfate ester, alkyl sulfonate, alkyl aryl sulfonate, alkyl phosphate ester salt, polyoxy Ethylene alkyl sulfate, quaternary ammonium salt, oxyalkylamine, lecithin, saponin and the like.
  • the plant growth regulator and the composition for regulating plant growth of the present invention can be produced by mixing and stirring the above-mentioned plant growth regulator and other components according to a conventional method.
  • the plant growth regulator and the composition for controlling plant growth of the present invention have an effect of increasing root mass, an effect of suppressing stem elongation, and the like, and are particularly preferably used as a rooting promoter.
  • the plant of the present invention may be used directly as it is, or may be used after being diluted or suspended to a predetermined concentration with water.
  • Growth regulators and compositions for regulating plant growth include plants, seeds, tissue cultures, etc. It is particularly useful as a pesticide and fertilizer.
  • hydroponics When applied to plants, it can be used as a soil treatment agent, a foliage treatment agent, a seed treatment agent before sowing, a plant treatment agent before transplantation, and the like.
  • hydroponics it may be used by mixing with hydroponic solution, and in tissue culture, it may be used by suspending or dissolving in a medium.
  • the concentration used is 0.01 to 100 ppm, preferably 1 to 500 ppm, particularly preferably. Can be used in the range of 5 to 100 ppm.
  • a spreading agent may be used in combination, and the type and amount of the spreading agent used are not particularly limited.
  • a liquid carrier such as water, alcohols, and ketones to a concentration of 0.01 to 100 ppm, and spray or dry the dried seeds. It can be immersed in a diluent and absorbed by seeds. In this case, the liquid carrier may be evaporated after the absorption.
  • a formulation prepared using a solid carrier of mineral powder such as clay can be used by adhering it to the seed surface.
  • the concentration in the culture medium is usually 0.01 to 100,000 in the commonly used plant tissue culture medium (MS medium, White medium, Gamborg B5 medium, etc.). It can be used by dissolving or suspending in the range of ppm, preferably in the range of 0.1 to 1000 ppm.
  • saccharides saccharides (sucrose, glucose, etc.) as carbon sources and cytokins as various plant hormones are used.
  • 'Adenine, etc. force Inechin) and gibberellins (GA 3, GA 4), O Kishin (indoleacetic acid, naphthoquinone evening etc. Ren acetate), it may be obtained as appropriate pressurizing the Apushijin acid.
  • the root or the whole of the plant When directly absorbed into the plant before transplantation, the root or the whole of the plant can be used by immersing it in a solution diluted or suspended at a working concentration of 0.1 to 100 ppm. If the cuttings are used, the base or the whole can be used after being crushed. In this case, the crushing time is preferably 10 seconds to 1 week, particularly 1 hour to 3 days.
  • a formulation prepared using a solid carrier of a mineral powder may be attached to the root or, in the case of spikelets, to the stem base.
  • the administration time of the plant growth regulator or the composition for regulating plant growth of the present invention can be used at any time during the growing period, but particularly before and after sowing when applied as a rooting promoter. It is especially effective when raising seedlings, before and after work involving cultivated rooting such as transplanting, or when root damage occurs due to weather factors.
  • the root mass and root density increase through an increase in the number of lateral roots, the number of adventitious roots, etc. Improving and raising healthy seedlings, promoting growth, improving water absorption, improving fertilizer absorption, improving fertilizer component utilization, maintaining green color, improving photosynthetic capacity, improving water stress tolerance, preventing lodging, improving yield, etc. The effect is obtained.
  • the plant to which the plant growth regulator and the composition for controlling plant growth of the present invention are applied is not particularly limited.
  • eggplants such as tomato, pepper, tomato, eggplant, cucumber, pumpkin, melon, and watermelon
  • other vegetables such as cabbage, broccoli, Chinese cabbage, celery, and so on.
  • Fresh vegetables such as spices, lettuce, spices, leeks, evening onions, garlic, etc., soybeans, peanuts, green beans, endu, azuki, etc., other fruits and vegetables such as strawberries, radish, turnips, carrots, Direct roots such as burdock, potatoes such as taro, cassava, raisho, sweet potato, nagaimo, etc., asparagus, spinach, soft vegetables such as koku, eustoma, strike Flowers, such as rice, corn, etc., grasses, such as bentgrass and red rice, oil crops, such as rapeseed and peanut, sugar crops, such as sugar cane, sugar beet, and ivy , Ficus crops such as ixa, forage crops such as clover, sorghum, and dent corn, linco ", deciduous fruit trees such as pear, grape, peach, etc. And woody species such as cedar.
  • the present invention can be used in combination with other plant growth regulators, and in some cases, a synergistic effect can be expected.
  • a synergistic effect can be expected.
  • it when raising seedlings under conditions that are extremely prone to growth, such as high planting density, high humidity, and lack of sunshine, it has a strong stem elongation inhibitory effect for the purpose of growing good-quality seedlings with a low aboveground and underground weight ratio.
  • anti- gibberellins eg, butorazole, nicotinazole P, ancimidol, etc.
  • growth inhibitors eg, daminozide
  • ethylene generators eg, ethephon
  • auxin-based compounds indoleacetic acid, indolebutyric acid, naphthylacetoamide, naphthamide, etc.
  • auxin-based compounds that originally have a rooting-promoting effect are used to enhance the rooting-promoting effect.
  • Acetic acid Further, at the time of seed treatment before sowing, a gibberellin agent having a germination promoting effect may be used in combination.
  • plant growth regulators that can be used in combination with the plant growth regulator or the plant growth regulating composition of the present invention are not limited thereto.
  • the plant growth regulator and the composition for regulating plant growth of the present invention can be used in combination with various insecticides, fungicides, microbial pesticides, fertilizers and the like.
  • combination use with a fungicide, such as hydroxyisoxazole, metas focalp, or metalaxyl which has been reported to promote rooting in addition to the bactericidal effect, is effective.
  • Preparation Example 1 is the same as Preparation Example 1 except that 5.4 g of succinic anhydride was used and 7.6 g of 2- (p-methoxyphenyl) ethylamine was used instead of 2- (p-tolyl) ethylamine. In the same manner as in the above, 9.7 g (yield 77%) of compound 02 was obtained.
  • Production Example 1 was repeated except that succinic anhydride was changed to 5.4 g and 2- (4-tolyl) ethylamine was replaced by 7.8 g of 2- (4-chlorophenyl) ethylamine. In the same manner as in Example 1, 6.4 g (yield 50%) of compound 03 was obtained. Production Example 4
  • Production Example H Same as Production Example 1 except that 5.4 g of succinic anhydride was used, and 6.8 g of 3-phenylpropylamine was used instead of 2- (p-tolyl) ethylamine. Thus, 4.0 g (yield 34%) of a compound 07 was obtained.
  • Production Example 1 is the same as Production Example 1 except that 2.5 g of maleic anhydride was used instead of succinic anhydride and 3.1 g of phenethylamine was used instead of 2- (p-tolyl) ethylamine.
  • Preparation Example 11 yielded 3.6 g (yield 66%) of compound 10
  • Production Example 21 was repeated in the same manner as in Production Example 21 except that isopropanol 10 OmL was used instead of n-propanol. Then, the obtained crystals were purified by a silica gel column and dried under reduced pressure to obtain 6.1 g (yield 51%) of compound 22.
  • Production Example 33 Production Example 3 was repeated except that succinic anhydride was changed to 8.4 g, and 1-1.0 g of 2- (4-fluorophenyl) ethylamine was used instead of 2- (2-chlorophenyl) ethylamine. As in Example 33, 2.3 g (yield 12%) of compound 35 was obtained.
  • Table 1 Table 2, Table 3, Table 4, and Table 5 show the physical properties of ⁇ 39.
  • Azuki seeds (variety name: Erimoshozu, sold by Snow Brand Seed Co., Ltd.) are sown in a commonly used nursery box (35cm x 25cm x 5cm depth) filled with vermiculite (Kushiro Coal Drying Co., Ltd.). The plants were cultivated for 12 days under fluorescent light (2200 looks, 20 ° C). The fully developed primary leaves were cut off at a height of 3 cm, and the shoots at the shoot apex were also excised to prepare test materials.
  • Compounds 1, 14, 15, and 16 to 30 were directly diluted with distilled water, and the others were sodium hydroxide.
  • the solution was diluted with distilled water while neutralizing with an aqueous solution to prepare an aqueous solution having a concentration of 7 ppm and 70 ppm.
  • the cuts of the above-mentioned azuki test material were immersed in these aqueous solutions for 72 hours.
  • the base was washed with water, and the base was immersed in distilled water for 4 days and cultured, and the number of adventitious roots generated was measured.
  • those treated with distilled water were cultured, and the number of adventitious roots was similarly measured.
  • Table 6 Table 7 and Table 8, a higher rooting promoting effect was observed as compared with the number of rooting in the control group.
  • a hard plastic cell tray with a size of 4.5 cm x 4.5 cm and 98 holes per well, it is filled with a dedicated culture soil (Scotts, Scotts-Sierra Horticultural Products) containing peat as a main component.
  • Tomato seeds (cultivar name: Ochiyobo, sold by Snow Brand Seed Co., Ltd.) were cultivated in a glass house with additional fertilization.
  • IBA indolebutyric acid
  • MCPB 2-methyl-4 'Ethyl butyrate
  • compound 14 was directly diluted with deionized water, and compound 13 and indolebutyric acid were diluted with deionized water while neutralizing with an aqueous sodium hydroxide solution.
  • the 2-methyl 4-chlorophenethyl butyrate (MCPB) was prepared by diluting commercially available Madec emulsion (manufactured by Agro-Kanesha Co., Ltd., containing 20% of MCPB). Deionized water was used as a control.
  • Root dry weight On the 29th day after sowing, the root dry weight, the total dry weight, the plant height, and the length of the first cotyledon of the cotyledon were measured in 15 x 2 replicates of 15 individuals. The results are shown in Table 10. The values in parentheses in the table indicate the relative values in terms of% when the control group is 100 (the same applies hereinafter). Root dry weight increased by 7% or more in the treatments with all concentrations of compound 13 and compound 14, indicating that the root-promoting effect was also high in actual tomato seedlings.
  • Example 3 Using a hard plastic cell tray with a size of 4 cm x 4 cm and a size of 128 holes, the same method as in Example 3 was used for prococcoli one seed (variety name: Midorine, Sakata seed sales) ). On the 14th and 21st days after seeding, 500 mL of an aqueous solution of compound 13, compound 14, indolebutyric acid and 2-methyl 4-chlorophenyloxyacetic acid ethyl ester prepared in the same manner as in Example 3 was used for each tray. Sprayed. On the 29th day after the seeding, each item was measured in the same manner as in Example 3 with 16 individuals ⁇ 2 repetitions. The results are shown in Table 11.
  • Root dry matter increased in the treated groups at 100 ppm and 100 ppm of Compound 13 and at all concentrations of Compound 14. From this, it was confirmed that the root-promoting effect was high even in the actual prococcy growing seedlings. The total dry weight increased in the 1 O ppm and 100 ppm treatments of Compound 13 and Compound 14, and a growth promoting effect was also observed.
  • the dry weight of the roots was increased by the treatment of Compounds 13 and 14, and it was recognized that the rooting promoting effect was high even in the actual lettuce seedlings.
  • the total dry weight also increased, and a growth promoting effect was also observed. Since these effects are desirable at the time of raising seedlings and no phytotoxicity was observed, the usefulness of compound 13 and compound 14 was confirmed.
  • phytotoxicity was caused by 2-methyl-4-monochlorophenyloxybutyrate, and the effect of indolebutyric acid, which was not toxic, was lower than that of Compounds 13 and 14.
  • Example 3 Using a plastic plastic tray with a size of 4.5 cm x 4.5 cm and 98 holes, the same method as in Example 3 is used for pepper seeds (variety name: Ace, Yuki Seed and Seed Co., Ltd.) Was sown. On the 12th day and 21st day after the seeding, 500 mL of an aqueous solution of Compound 13 and Compound 14 prepared in the same manner as in Example 3 was sprayed per tray. On the 32nd day after sowing, the root dry weight, leaf area, total dry weight and aboveground underground weight ratio were measured in 15 individuals ⁇ 2 replicates. The results are shown in Table 13. Regarding the root dry weight, Compound 13 showed an increase of 75% or more in all concentrations, and Compound 14 showed an increase of more than 60% in the O ppm and 100 ppm treatments.
  • Tomato seedlings were grown in the same manner as in Example 3 using a hard plastic cell tray having a size of 4.5 cm ⁇ 4.5 cm and 98 holes.
  • An aqueous solution of compound 13 and compound 14 prepared in the same manner as in Example 3 was sprayed on the seedlings 30 days later at 50 OmL per tray.
  • the day after spraying the plants were transplanted to a 12 cm diameter x 1 Ocm deep vinyl pot filled with 55 Om of Sankyo Horticultural Soils (Hokkaido Sankyo Co., Ltd.).
  • Compounds 13 and 14 increased the dry weight of the roots by 8% or more in the treatments of all concentrations, and it was confirmed that the treatment immediately before transplantation also exerted rooting promoting effect after transplantation. The total dry weight and the number of leaves increased in all treatments, and the growth promotion effect after transplantation was also observed.
  • the cuttings were cut and sprouted on a nursery bed filled with a culture soil in which perlite and peat were mixed at a ratio of 7: 3 to a plastic cell tray, and cultivated in a glass house. After cutting and buds, 34 to 4 days later, the ratio of rooting individuals was measured by 5 X3 repetitions, and the root dry weight was also measured. The results are shown in Table 15. At all treatment concentrations, root dry matter increased by more than 450% in California and Cotylion, and increased by more than 32% in California Elves, and the proportion of rooting individuals increased by more than 20% in Elves . From these results, it was confirmed that the rooting promoting effect was high also in the cut and raised seedlings of carnation.
  • the plant growth regulator and the composition for regulating plant growth of the present invention have a high activity of promoting rooting of plants and have extremely weak side effects such as an action of promoting upgrowth on leaves. It can be used over the entire growing period and is particularly useful as a rooting promoting agent or a composition for promoting rooting at the time of seedling-transplanting. Also, plant tissue It can also be used by adding it to a medium for the purpose of culturing and differentiating roots.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des agents régulant la croissance de végétaux et comprenant en tant que composants actifs les composés représentés par la formule générale ou leurs sels. L'invention concerne aussi des compositions régulant la croissance de végétaux et contenant les composés ou les sels susmentionnés ainsi que des supports de pesticides ou d'engrais. L'invention se rapporte en outre à l'utilisation des composés susmentionnés ou de leurs sels dans la fabrication d'agents régulant la croissance de végétaux. Les agents régulant la croissance de végétaux et similaires manifestent une intense activité de stimulation du racinement et produisent très peu d'effets secondaires tels que l'épinastie des feuilles. Ces propriétés les rendent particulièrement utiles dans la culture de semis et la production de graines et de semis de produits agricoles, dans la fixation de plantes de gazon et similaires et dans la culture de tissus. Dans cette formule, Ar représente un phényle substitué en option, A représente un alkylène inférieur; B représente un alkylène inférieur ou similaire et; R1 représente hydroxy ou similaire.
PCT/JP1999/001181 1998-03-11 1999-03-11 Agent regulant la croissance de vegetaux Ceased WO1999045774A1 (fr)

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AU27475/99A AU2747599A (en) 1998-03-11 1999-03-11 Plant growth regulating agents

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JP10/59523 1998-03-11
JP05952398A JP4087942B2 (ja) 1998-03-11 1998-03-11 植物成長調整剤

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WO1999045774A1 true WO1999045774A1 (fr) 1999-09-16

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JP (1) JP4087942B2 (fr)
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WO2001072753A1 (fr) * 2000-03-26 2001-10-04 Shiseido Company, Ltd. Derives d'acide gras cetol et agents regulant la croissance de plantes
WO2010079763A1 (fr) * 2009-01-09 2010-07-15 雪印種苗株式会社 Procédé de production d'un composé amide d'acide indolalkylsuccinique
US20100267556A1 (en) * 2009-04-20 2010-10-21 Franklin Paul Silverman Plant Growth Enhancement with Combinations of PESA and Herbicides
WO2010123849A1 (fr) 2009-04-20 2010-10-28 Valent Biosciences Corporation Composition fongicide
JP2011500812A (ja) * 2007-10-25 2011-01-06 バレント・バイオサイエンシーズ・コーポレイション 植物成長促進剤
WO2012046821A1 (fr) * 2010-10-04 2012-04-12 Sumitomo Chemical Company, Limited Procédé pour réduire le stress hydrique dans des plantes
US20120100993A1 (en) * 2010-10-20 2012-04-26 Franklin Paul Silverman Plant Growth Enhancement with Combinations of PESA and Herbicides
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WO2013015394A1 (fr) * 2011-07-22 2013-01-31 Sumitomo Chemical Company, Limited Composition et procédé permettant de lutter contre les arthropodes nuisibles
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JP2011500812A (ja) * 2007-10-25 2011-01-06 バレント・バイオサイエンシーズ・コーポレイション 植物成長促進剤
WO2010079763A1 (fr) * 2009-01-09 2010-07-15 雪印種苗株式会社 Procédé de production d'un composé amide d'acide indolalkylsuccinique
JP5395811B2 (ja) * 2009-01-09 2014-01-22 雪印種苗株式会社 インドリルアルキルコハク酸アミド化合物の製造法
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AU2747599A (en) 1999-09-27
JPH11255607A (ja) 1999-09-21

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