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WO2010137662A1 - Inhibiteur de la ramification des plantes, son procédé de fabrication et composition inhibitrice de la ramification des plantes - Google Patents

Inhibiteur de la ramification des plantes, son procédé de fabrication et composition inhibitrice de la ramification des plantes Download PDF

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Publication number
WO2010137662A1
WO2010137662A1 PCT/JP2010/059027 JP2010059027W WO2010137662A1 WO 2010137662 A1 WO2010137662 A1 WO 2010137662A1 JP 2010059027 W JP2010059027 W JP 2010059027W WO 2010137662 A1 WO2010137662 A1 WO 2010137662A1
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Prior art keywords
plant
branching
inhibitor
compound
plant branching
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Japanese (ja)
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山口信次郎
梅原三貴久
秋山康紀
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Osaka Metropolitan University
RIKEN
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Osaka Prefecture University PUC
RIKEN
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom

Definitions

  • the present invention relates to a plant branch inhibitor, a method for producing the same, and a plant branch inhibitor composition.
  • Plant branching control is important in controlling the production of agricultural and horticultural crops. Therefore, in the agricultural and forestry field, an efficient, safe and inexpensive branching control agent is required.
  • Cytokinin (transzeatin and its derivatives) and auxin (indole acetic acid and its derivatives) are known as important hormones that control the branching pattern of plants. Cytokinin is a hormone that promotes the growth of buds. When buds are released from dormancy and elongated, they are locally and transiently biosynthesized in the stem and supplied to the buds to promote the growth of buds. Is known (Non-Patent Document 1). On the other hand, auxin is a hormone that is biosynthesized at the apical bud and moves through the stem through the auxin transporter protein PIN, thereby suppressing the growth of plant buds (Non-patent Document 2). Thus, auxin can be a plant branching inhibitor.
  • auxin not only suppresses the growth of axillary buds, but also exhibits various effects such as cell division promoting action, growth promoting action, ovary growth promoting action, rooting promoting action, etc., so the hormone was administered externally. In this case, there is a problem that the plant body is deformed. Therefore, it is not suitable as a practical branching inhibitor.
  • Non-patent Document 3 maleic hydrazide, an auxin antagonist, has been used as an agrochemical for suppressing tobacco buds.
  • this pesticide has a problem of carcinogenicity of hydrazide mixed as an impurity, and its use is regulated from the viewpoint of safety.
  • a plant branch inhibitor having high specificity as a branch inhibitory action and high safety to the human body and the environment has not been known yet. Therefore, there has been a strong demand for new plant branching inhibitors having such properties.
  • Non-patent Document 4 Suppressing the branching of the plant based on the presumed function based on the product of the causative gene revealed by molecular genetic analysis in max1 to 4 mutants of Arabidopsis thaliana, analysis of the max multiple mutants, and grafting experiments It was speculated that the factor is a carotenoid-derived hormone-like low-molecular substance that can move from the root to the above-ground part (Non-patent Document 4). However, the substance body has not yet been identified.
  • strigolactone function as the novel branching inhibitory hormones.
  • FIGS. 2 and 3 Non-Patent Document 5
  • strigolactone specifically inhibits bud elongation of plants unlike auxin.
  • the French research team also revealed that the hormone-like substance is strigolactone (Non-patent Document 6).
  • strigolactones and their derivatives are known to have an action of promoting seed germination of root parasitic plants, Striga and Orobanche (Cook) et al., 1972, Journal of the American Chemical Society, 94: 6198-6199). These root parasitic plants do not carry out photosynthesis necessary to acquire energy necessary for self-survival and growth, or have no chlorophyll so that they grow by depriving the root of the host plant. Since the growth of host plants is significantly hindered by infestation of root parasitic plants, these root parasitic plants have caused enormous damage to agricultural production around the world. Therefore, applying strigolactone or a derivative thereof to the field contains a risk of inducing seed germination such as striga and affecting agricultural production itself.
  • strigolactone in order to put strigolactone into practical use as a plant branching inhibitor, it has a plant branching inhibitory activity equivalent to or better than strigolactone, and can be chemically synthesized in a simple process at low cost. Moreover, it was necessary to develop a compound having no or weak seed germination promoting action of Striga or Orobanki.
  • the present inventors conducted extensive research and determined a site essential for plant branching inhibitory activity in the chemical structure of strigolactone.
  • the enol ether structure that connects the C and D rings among the A, B, C, and D rings in the chemical structure of a general natural strigolactone (Fig. 5; shows strigol in this figure) is active. It was found that the carbon atom at the 2 ′ position of the D ring has a high activity and that the D ring is essential for its activity.
  • R 1 and R 2 each independently represent a hydrogen atom (H), a lower alkyl group, a lower alkenyl group, or a lower alkynyl group.
  • a plant branching inhibitor composition comprising the plant branching inhibitor according to (4) or (5), which is an active ingredient, and an agriculturally acceptable carrier.
  • the compound which is a plant branching inhibitor of the present invention has low activity to promote seed germination of Striga or Orobanki, it can be applied to the soil.
  • the plant branching inhibitor of the present invention can be synthesized with an inexpensive material and with fewer steps. This production method makes it possible to provide the plant branching inhibitor of the present invention at low cost.
  • the branching can be specifically controlled by applying to the plant.
  • hyperbranched mutants The conceptual diagram which shows the factor which participates in the cascade from biosynthesis of strigolactone to branch suppression, and each step. It shows the branching inhibitory activity of strigolactone in rice.
  • WT represents wild-type rice
  • d3 , d10 and d17 represent dwarf ( d ) mutants showing increased branching and weak fertility of rice.
  • the d17 mutant and d10 mutant have mutations in the genes encoding CCD7 (carotenoid oxidative cleavage enzyme 7) and CCD8 (carotenoid oxidative cleavage enzyme 8), respectively, enzymes involved in the strigolactone biosynthesis pathway (Fig. 2).
  • the d3 mutant has a mutation in a gene encoding an F-box protein that functions downstream of the action step of strigolactone in the branching suppression pathway (see FIG. 2). It can be seen that in the d17 mutant and d10 mutant, the mutation phenotype was complemented by the addition of strigolactone, and branching was suppressed. In contrast, the mutant phenotype is not complemented in the d3 mutant.
  • Chemical synthesis process of natural strigolactone (5-deoxystrigol). Chemical structure and name of each ring of natural type strigolactone (strigol). The relationship between the four stereoisomers (A) of synthetic strigolactone GR24 and the tillering inhibitory activity (B) of rice.
  • C ring-cleavage GR5 derivative and salt thereof One embodiment of the present invention is a C ring-cleavage GR5 derivative or salt thereof. Each will be described in detail below.
  • C ring cleavage type GR5 derivative One embodiment of the present invention is a compound represented by the following general formula (I).
  • R 1 and R 2 each independently represent a hydrogen atom (H), a lower alkyl group, a lower alkenyl group, or a lower alkynyl group.
  • the compounds represented by the general formula (I) are collectively referred to as “C ring cleavage type GR5 derivative”.
  • the C ring cleavage type GR5 is a compound having a structure in which the C ring of the strigolactone skeleton, that is, the ⁇ -lactone ring is opened in GR5 described later.
  • the double bond portion of the enol ether structure in formula (I) may be either trans type or cis type.
  • the C-ring cleavage type GR5 derivative of the present invention is preferably a compound in which the carbon atom at the 2 ′ position of the methylbutenolide ring corresponding to the D ring in the strigolactone skeleton is in the R configuration. That is, it is a compound represented by the following general formula (VI).
  • the “lower alkyl group” is a linear or branched alkyl group having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms. Specifically, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group is included.
  • the “lower alkenyl group” is a linear or branched alkenyl group having 2 to 5 carbon atoms, preferably 2 to 3 carbon atoms. Specifically, an ethenyl group, a propenyl group, or an isomer thereof is included.
  • the “lower alkynyl group” is a linear or branched alkynyl group having 2 to 5 carbon atoms, preferably 2 to 3 carbon atoms. Specifically, an ethynyl group or a propynyl group is included.
  • R 1 and R 2 are preferably each independently a hydrogen atom (H) or a methyl group.
  • a compound in which both R 1 and R 2 are methyl groups that is, a compound represented by the following formula (II) (2-methyl) having a structure in which the 4-position and 5-position carbons of the ⁇ -lactone ring are opened.
  • -3- (4-Methyl-5-oxo-2,5-dihydrofuran-2-yloxy) acrylate) is preferred.
  • MePrGR5 the compound represented by the formula (II) is hereinafter referred to as “MePrGR5” for convenience.
  • the carbon atom at the D-ring 2′-position is also R in MePrGR5.
  • a compound represented by the following formula (VII) having the configuration is more preferable.
  • MePrGR5 in which the D ring 2 ′ position is in S configuration may be mixed.
  • a compound in which R 1 is a methyl group and R 2 is a hydrogen atom that is, a compound represented by the following formula (III) ((Z) -methyl-3- ( 4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy) and a compound represented by formula (IV) ((E) -methyl-3- (4-methyl-5-oxo-2,5- Dihydrofuran-2-yloxy) is also preferred.
  • the C-ring-cleavable GR5 derivative of the present invention preferably has the R configuration at the carbon atom at the 2′-position of the D-ring, even in trans MeAcGR5 and cis MeAcGR5, A compound represented by the following formula (VIII) or formula (IX) in which the carbon atom is in the R configuration is more preferred.
  • MeAcGR5 is represented by formula (VIII) or formula (IX)
  • MeAcGR5 having the S configuration at the 2′-position of the D ring may be mixed.
  • C-ring Cleaved GR5 Derivative Salt One embodiment of the present invention is a salt of a C-ring cleaved GR5 derivative.
  • the “salt of a C-ring-cleavable GR5 derivative” refers to a basic addition salt formed when R 1 is H (hydrogen atom) in the compound represented by the formula (I).
  • Examples of basic addition salts include alkali metal salts such as sodium salt or potassium salt, alkaline earth metal salts such as calcium salt or magnesium salt, trimethylamine salt, triethylamine salt, dicyclohexylamine salt, ethanolamine salt, diethanolamine.
  • aliphatic amine salt such as triethanolamine salt or brocaine salt
  • aralkylamine salt such as N, N-dibenzylethylenediamine
  • heterocyclic aromatic amine such as pyridine salt, picoline salt, quinoline salt or isoquinoline salt Salt
  • basic amino acid salt such as arginine salt or lysine salt
  • ammonium salt or tetramethylammonium salt tetraethylammonium salt
  • benzyltrimethylammonium salt benzyltriethylammonium salt
  • Le tributylammonium salts include quaternary ammonium salts such as methyl trioctyl ammonium salts or tetrabutylammonium salts.
  • Plant branching inhibitor One aspect of the present invention is a plant selected from the group consisting of the C-ring-cleavage-type GR5 derivative represented by the general formula (I) or a salt thereof and the compound represented by the following formula (V): It is a branching inhibitor.
  • the compound represented by the formula (V) is hereinafter referred to as “GR5” (Mangnus et al. 1992a, supra).
  • the GR5 of the present invention is particularly preferably (+) GR5 in which the 2'-position carbon atom of the D ring represented by the following formula (X), that is, the methylbutenolide ring, is in the R configuration.
  • (+) GR5 in S configuration also has plant branching inhibitory activity although it is weak. Therefore, when (+) GR5 is used as a plant branching inhibitor, ( ⁇ ) GR5 may be mixed.
  • Plant branching suppression refers to suppression of plant branching during the plant growth process.
  • the term “branch” means that side buds or side buds that become new tips from stems, trunks, and branches are generated and elongated.
  • the “branch” in which new side buds are generated from the roots typified by monocotyledonous plants and is elongated is also included in the branches in this specification.
  • Plant branching inhibitor refers to a drug having a plant branching inhibitory action.
  • the C-ring cleavage type GR5 derivative for example, MePrGR5 and MeAcGR5
  • GR5 is an active ingredient of the branching inhibitor.
  • the plant branching inhibitor of the present invention it becomes possible to control the branching of plants.
  • it is useful when it is desired to suppress branching to reduce the number of branches and relatively promote apical bud elongation.
  • it can be applied to tobacco to suppress side buds, or applied to horticultural plants such as chrysanthemum to save the effort of plucking.
  • the plant branching inhibitor of the present invention has a plant branching inhibitory activity that is 10 to 100 times higher than that of conventional strigolactone, as shown in Examples described later.
  • it has the advantage that there is no problem even if it is applied in the soil, because the germination-inducing activity for the seeds of the root parasitic plants of the genus Striga or Orobanchi is low.
  • the plant branching inhibitor of the present invention is decomposed relatively quickly in nature, it does not remain in soil, water or plants for a long period of time even when used as an agricultural chemical. There is an advantage that the effect on animals including the animal is low.
  • the plant branching inhibitor of the present invention has a relatively simple structure as compared with strigolactone and its derivatives having a known structure, so that it is inexpensive and easy as described in detail in the next section. It can be chemically synthesized. As a result, there is an advantage that mass production is possible and practical application is easy.
  • a further aspect of the present invention relates to MePrGR5 that constitutes a plant branching inhibitor, that is, a C-ring-cleavable GR5 derivative represented by formula (II) and MeAcGR5, that is, formula (III) or (IV Is a method for producing a C-ring-cleavage type GR5 derivative.
  • a plant branching inhibitor that is, a C-ring-cleavable GR5 derivative represented by formula (II) and MeAcGR5
  • formula (III) or (IV Is a method for producing a C-ring-cleavage type GR5 derivative a plant branching inhibitor
  • the production method of each compound will be described with specific examples.
  • the drug, the dose of the drug, the operation and / or the procedure described herein are based on the common general knowledge of those skilled in the art. Changes and modifications can be made as appropriate without departing from the scope.
  • a base is gradually added to a solution containing methyl propionate and alkyl formate as raw materials to react them.
  • Alkyl formate may be added slowly into a solution containing methyl propionate and base, or methyl propionate may be added slowly into a solution containing alkyl formate and base.
  • methyl formate or ethyl formate can be used as alkyl formate.
  • the molar ratio of alkyl formate to methyl propionate in the solvent is usually 3-8, preferably 4-7, more preferably 5.
  • the base is not limited, and for example, potassium tert-butoxide or sodium hydride can be used.
  • the solvent is not particularly limited as long as it can dissolve methyl propionate and alkyl formate.
  • tetrahydrofuran, dimethylformamide (DMF), etc. are mentioned.
  • the base it is carried out at a temperature below room temperature. It is preferable to carry out stirring under ice cooling. After completion of the reaction, the solution is further heated at room temperature under a chemically inert gas atmosphere, that is, 5 to 40 ° C., preferably 10 to 35 ° C., more preferably 15 to 30 ° C., more preferably 15 to 25 ° C.
  • the stirring can be performed for 2 to 12 hours, preferably 4 to 10 hours, more preferably 5 to 8 hours.
  • Bromomethylbutenolide is preferably added to the solution after the reaction so that the molar ratio to methyl propionate is 0.5 to 2.0, preferably 1 to 1.5, more preferably 1.1 to 1.3, and still more preferably 1.2. .
  • Bromomethylbutenolide may be synthesized according to the method described in Macalpine et al., 1976, Journal of Chemistry, Society-Perkin Transactions, 1: 410-416.
  • the bromomethylbutenolide reaction is carried out under a chemically inert gas atmosphere at room temperature, ie 5-40 ° C., preferably 10-35 ° C., more preferably 15-30 ° C., more preferably 15-25 ° C. For 10 to 24 hours, preferably 13 to 22 hours, more preferably 15 to 20 hours, and even more preferably about 17 hours.
  • the target MePrGR5 is obtained by the above process.
  • the presence of MePrGR5 can be confirmed by measurement techniques known in the art such as mass spectrometry such as NMR or Mass® Spectrum (eg, EIMS).
  • the MePrGR5 optical isomer (R configuration type) may also be separated by a measurement technique known in the art such as an HPLC method using a column for optical isomer separation.
  • MeAcGR5 Production method of MeAcGR5
  • a base is gradually added to a solution containing methyl acetate as a raw material, and they are reacted.
  • Alkyl formate may be added slowly into a solution containing methyl acetate and base, or methyl acetate may be added gradually into a solution containing alkyl formate and base.
  • methyl formate or ethyl formate can be used as alkyl formate.
  • the molar ratio of alkyl formate to methyl acetate in the solvent is usually 3 to 8, preferably 4 to 7, and more preferably 5.
  • the base is not limited, and for example, potassium tert-butoxide or sodium hydride can be used.
  • the solvent is not particularly limited as long as it can dissolve methyl acetate and alkyl formate.
  • tetrahydrofuran, dimethylformamide (DMF), etc. are mentioned.
  • the base it is carried out at a temperature below room temperature. It is preferable to carry out stirring under ice cooling. After completion of the reaction, the solution is further heated at room temperature under a chemically inert gas atmosphere, that is, 5 to 40 ° C., preferably 10 to 35 ° C., more preferably 15 to 30 ° C., more preferably 15 to 25 ° C.
  • the stirring can be performed for 2 to 12 hours, preferably 4 to 10 hours, more preferably 5 to 8 hours.
  • Bromomethylbutenolide is preferably added to the solution after the reaction so that the molar ratio to methyl acetate is 0.5 to 2.0, preferably 1 to 1.5, more preferably 1.1 to 1.3, and still more preferably 1.2.
  • Bromomethylbutenolide may be synthesized according to the method described in Macalpine et al., 1976, Journal of Chemistry, Society-Perkin Transactions, 1: 410-416.
  • the bromomethylbutenolide reaction is carried out under a chemically inert gas atmosphere at room temperature, ie 5-40 ° C., preferably 10-35 ° C., more preferably 15-30 ° C., more preferably 15-25 ° C. For 10 to 24 hours, preferably 13 to 22 hours, more preferably 15 to 20 hours, and even more preferably about 17 hours.
  • each geometric isomer can be separated by preparative HPLC after being roughly separated by, for example, hexane-acetone system stepwise elution using a column such as a silica gel open column as necessary. 3-3.
  • GR5 Bromomethylbutenolide is synthesized according to the method described in Macalpine et al., 1976, Journal of the Chemical Society-Perkin Transactions 1: 410-416. Thereafter, GR5 can be synthesized using known techniques (Mangnus et al., 1992a, supra) for C ring and D ring.
  • Plant Branch Inhibiting Composition Another aspect of the present invention is a plant branch inhibiting composition.
  • the plant molecule inhibitor composition of the present invention comprises at least one plant branch inhibitor of the present invention as an active ingredient and an agriculturally acceptable carrier.
  • the plant branching inhibitor acts as an active ingredient for plant branching suppression in the plant branching suppression composition of the present invention.
  • the plant branching inhibitor contains at least one plant branching inhibitor selected from the group consisting of the C-ring cleavage GR5 derivative of the present invention, preferably MePrGR5, MeAcGR5 and GR5.
  • the amount of the plant branch inhibitor in the plant branch inhibitor composition of the present invention includes the type of plant branch inhibitor contained, the type of carrier contained, the type of plant to be applied, the purpose of application, the application method, and the case of containing. Depends on various conditions such as the type of drug having other pharmacological effects. In consideration of various conditions so that the plant branching inhibitor contained in the plant branching inhibitory composition in the range of technical common sense in the field is a desired amount for the target plant after application, The content of branch inhibitor can be determined.
  • Agriculturally acceptable carrier is a substance that facilitates the application of a plant branching inhibitor, inhibits or suppresses its degradation, and / or controls its rate of action, and is used for plants including outdoors and indoors. Even if it is applied to cultivation, it means that there is no or little harmful effect on the environment such as soil and water quality, or no or little harm to animals, especially humans. For example, solvents and adjuvants.
  • Suitable solvents include water, aromatic solvent (eg benzene, toluene, xylene, tetrahydronaphthalene, alkylated naphthalene or derivatives thereof), paraffins (eg mineral oil fraction), chloroform, carbon tetrachloride, ketones. (For example, acetone, cyclohexanone), pyrrolidones (for example, NMP or NOP), acetate (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids, fatty acid esters, or a mixed solvent thereof.
  • aromatic solvent eg benzene, toluene, xylene, tetrahydronaphthalene, alkylated naphthalene or derivatives thereof
  • paraffins eg mineral oil fraction
  • chloroform carbon tetrachloride
  • ketones for example, acetone, cyclohexanone
  • pyrrolidones for example
  • Suitable adjuvants include pulverized natural minerals, pulverized synthetic minerals, emulsifiers, dispersants and surfactants.
  • Examples of pulverized natural minerals include kaolin, clay, talc and chalk.
  • Examples of the pulverized synthetic mineral include highly dispersed silica and silicate.
  • Examples of the emulsifier include nonionic emulsifiers and anionic emulsifiers (for example, polyoxyethylene fatty alcohol ethers, alkyl sulfonates, and aryl sulfonates).
  • dispersant examples include lignosulfite waste liquor and methylcellulose.
  • surfactant examples include lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid alkali metal salt, alkaline earth metal salt and ammonium salt, alkylaryl sulfonate, alkyl sulfate, alkyl sulfonate, fat Alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, sulfonated naphthalene and naphthalene derivatives and formaldehyde condensates, naphthalene or naphthalenesulfonic acid and phenol and formaldehyde condensates, polyoxyethylene octylphenyl ether, ethoxylated isoforms Octylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol
  • the plant branching suppression composition of the present invention can include one or more of the agriculturally acceptable carriers.
  • other branch inhibitors and active ingredients having other pharmacological actions that is, insecticides, insecticides, herbicides, as long as they do not affect the effects of the branch inhibitor of the present invention.
  • Fungicides, and fertilizers eg, urea, ammonium nitrate, superphosphate.
  • Plant branching suppression method Another aspect of the present invention is to apply the plant branching inhibitor or the plant branching suppression composition of the present invention (hereinafter referred to as the plant branching inhibitor of the present invention) to a plant, This is a method for suppressing branching of plants.
  • the application form of the plant branching inhibitor and the like of the present invention is a conventional preparation form, for example, a solution, oil dispersion, emulsion, suspension preparation, powder, powder, which can be directly sprayed, applied and / or immersed. , Pastes, pellets, tablets and granules.
  • the method of applying the plant branching inhibitor of the present invention is not particularly limited as long as the branching inhibitory effect can be imparted to the target plant. What is necessary is just to apply by a well-known method in the said field
  • the plant branching inhibitor of the present invention can be easily and uniformly applied.
  • the applied plant branching inhibitor or the like of the present invention is absorbed from the root and spreads over the entire plant body, and the effects of the present invention can be exhibited.
  • the plant branching inhibitor of the present invention can be applied directly or indirectly into the soil. This is a convenient method when applied over a wide area such as a farm. Of course, it can also be used in indoor soil cultivation.
  • the plant branching inhibitor that is an active ingredient of the present invention is relatively easily decomposed in the soil by the action of microorganisms and the like. Therefore, when the plant branching inhibitor of the present invention is allowed to act transiently and a short-term effect is desired, it may be applied directly to the soil. Further, when it is desired to apply the plant branching inhibitor of the present invention over a long period of time, for example, when it is applied to a tobacco field to suppress the branching, it is effective in hydroponics considering decomposition by microorganisms.
  • the concentration may be 10 to 100 times the lowest concentration observed. Even if the plant branching inhibitor of the present invention is excessively administered as a result, the decomposition action by microorganisms is weaker than expected, and as shown in Example 4 described later, strigolactone and Unlike the auxin, the derivative of the present invention is advantageous in that the derivative does not cause malformation in the plant even by overdosing.
  • the plant branching inhibitor of the present invention can be indirectly applied by enclosing it in a sustained-release inclusion body. Also in this case, the applied plant branching inhibitor and the like of the present invention are absorbed from the root part and spread throughout the entire plant body, and the effects of the present invention can be exhibited.
  • coat etc. should just go to desired locations, such as a stem part and a petiole base, and is not limited. This method is effective when it is desired to suppress the branching action locally at a specific site in the plant body.
  • the application rate of the plant branching inhibitor or the plant branching suppression composition of the present invention has higher branching inhibitory activity than any of the strigolactone derivatives conventionally known as described above, A large effect can be achieved with a small amount of application.
  • the specific application amount varies depending on the plant branching inhibitor to be used and the type of target plant to be applied, the purpose of application and / or the application method. For example, even when it is desired to suppress branching of the same target plant, when the purpose of application is to completely suppress branching, a larger amount than when it is desired to suppress some branching. Need to be applied.
  • the decomposition rate of the plant branching inhibitor of the present invention is generally faster than that in hydroponic liquid due to the decomposition action of microorganisms in the soil.
  • the concentration of the plant branching inhibitor of the present invention is 1 to 50 nM, preferably 5 to 20 nM, in the final concentration.
  • it may be added to the hydroponic solution so as to be 8 to 12 nM.
  • a sufficient suppression effect can be expected at about 10 nM.
  • Non-Patent Document 5 an experimental system for verifying the plant branching inhibitory effect of strigolactone by hydroponics was developed.
  • cultivar Shiokari to be wild-type
  • a tiller mutant d3 , d10
  • These mutants like the d17 mutant shown in FIG. 1, show an abnormal increase in the number of tillers and a fertile phenotype compared to the wild type.
  • the d10 mutant is a mutant lacking the function of carotenoid cleavage enzyme 8 (CCD8) involved in the strigolactone biosynthetic pathway shown in Fig. 2, and the d3 mutant is a branching suppression signal by strigolactone. It is a mutant lacking the function of the F-box protein involved in the transmission pathway (Non-patent Document 5).
  • the splitting of the d10 and d17 mutants is suppressed, but the splitting of the d3 mutant having a mutation in a protein that functions downstream of strigolactone is not suppressed (FIG. 3). Further, even when strigolactone is treated with wild type, almost no morphological abnormality is observed (FIG. 3). That is, when various derivatives of strigolactone etc. are applied to each d mutant, if the derivative has the same branching suppression activity as strigolactone, the d10 and d17 mutants will have the phenotype Are complementary, but the wild type and d3 mutants have no change in their phenotype. Therefore, in this experimental system using d3 and d10 mutants, the following tillering suppression experiment was conducted by hydroponics of rice.
  • GR24 there are four optical isomers ((+) GR24, (-) GR24, (+)-2'-epiGR24, (-)-2'-epiGR24) shown in FIG. 6A. These were added at 0.01 ⁇ M, 0.1 ⁇ M, and 1 ⁇ M to the hydroponic solution of the (1) tillering suppression experimental system by hydroponic cultivation of rice, and each tillering inhibitory activity was examined.
  • Figure 6B shows the results.
  • a, b, c and d on the horizontal axis are (+) GR24, ( ⁇ ) GR24, (+)-2′-epiGR24 and ( ⁇ )-2′-epiGR24, and Cont. Is GR24.
  • the numerical value of the hydroponic solution not added indicates the amount ( ⁇ M) of each GR24 added to the hydroponic solution.
  • FIG. 7B The result is shown in FIG. 7B.
  • a, b, c and d on the horizontal axis are CompI, EntI, CompII and EntII, -Cont. Is untreated hydroponics, and + Cont. Is hydroponics with (+) GR24 added.
  • the numerical value indicates the amount ( ⁇ M) of each saturated GR24 added to the hydroponic solution.
  • FIG. 8B The result is shown in FIG. 8B.
  • a and b on the horizontal axis are ABC ring part and HB, respectively, and a + b is an ABC ring part and HB mixed in equal amounts and added at 1 ⁇ M.
  • -Cont. Indicates an untreated hydroponic solution
  • + Cont. Indicates a hydroponic solution to which (+) GR24 is added. All of the ABC ring part, HB, and ABC ring part + HB lost their tillering inhibitory activity. From this result and the result of Example 2, it was revealed that the enol ether structure is essential in the striation-control activity of strigolactone.
  • strigolactone derivative GR24 Effect of wild-type rice by application of strigolactone derivative High concentration strigolactone derivative GR24 was applied to wild-type rice, and the effects other than the inhibition of tillering were examined.
  • GR24 was added to the hydroponic solution at a usual 10-fold concentration of 10 ⁇ M, and compared with the case where GR24 was not treated.
  • cultivation was continued in a brown bottle containing 65 ml of a hydroponic solution containing GR24 at the same concentration after 14 days, not at the growth stage on the 14th day after sowing, and tillers and forms on the 28th day. Investigated about.
  • GR5 is the least known strigolactone derivative with chemical synthesis branching inhibitory activity, from GR7 consisting of B, C, D rings (Mangnus et al., 1992, Journal of Agricultural and Food Chemistry 40: 697-700)
  • branching inhibitory activity of GR5 from which the B ring was further removed the compound was chemically synthesized by the following method.
  • Fig. 10 shows the synthesis process of GR5.
  • ⁇ -butyrolactone Aldrich
  • Wako tetrahydrofuran
  • Aldrich methyl formate
  • bromomethylbutenolide was synthesized according to the method described in MacAlpine et al. (1976). The reaction was stopped by adding 1N HCL, and the resulting GR5 was extracted with ethyl acetate. The extract was washed once with water, dried over anhydrous sodium sulfate, concentrated, and purified with Wakogel® C-300® (Wako).
  • the product was analyzed by mass spectrometry and NMR using EIMS (electron impact mass spectrum) method.
  • EIMS electron impact mass spectrum
  • Verification of the effect of inhibiting rice tillering by GR5 GR5 synthesized in Example 5 has two optical isomers of (+) GR5 in the R configuration and ( ⁇ ) GR5 in the S configuration. Then, these branching inhibitory activities were verified using the rice tillering suppression experiment system in hydroponics as in Example 1.
  • the basic method was in accordance with Example 1.
  • (+) GR5 and (-) GR5 are (+) GR5 and (-) GR5, respectively, and Cont. Indicates a hydroponic solution to which GR5 or the like is not added.
  • (+) GR5 concentration-dependent tillering inhibitory activity was observed. This result is consistent with the result of Example 1.
  • (-) GR5 also showed concentration-dependent tillering inhibitory activity, but was much weaker than (+) GR5. It should be noted that (+) GR5 showed very strong branching inhibitory activity even at a concentration of only 0.01 ⁇ M, and 0.1 ⁇ M could completely suppress the occurrence of branching. That is, this result and the result of Example 1 indicate that (+) GR5 has a higher branching inhibitory activity than (+) GR24.
  • strigolactone derivatives were added to hydroponic solutions at various concentrations, The inhibitory effect of tillering in the d10 mutant was verified.
  • the varieties Shiokari were used in the same manner as the hydroponics in Example 1.
  • rice seeds were water-absorbed in the dark at 28 ° C. for 2 days, and the germinated seeds were precultured in the hydroponic medium of Example 1 and then transplanted to soil (JA Kumiai Synthetic Soil No. 3). After cultivation at 25 ° C., the tillering and morphology on the seventh day were examined.
  • the addition of GR5 was performed by adding 1 ⁇ M GR5 solution into the completely dried soil.
  • MePrGR5 Since the branching inhibitory activity of GR5 was observed, in order to search for a compound with a simpler structure having a branching inhibitory activity, the carbon between the 4- and 5-positions of the C ring in GR5 was opened. MePrGR5, one of the C-ring cleavage GR5 derivatives having a ring structure, was chemically synthesized by the following method.
  • FIG. 15 shows the synthesis process of MePrGR5.
  • 2 mmol methyl propionate and 2.8 mmol sodium hydride were added to 1 ml DMF.
  • 9.8 mmol of methyl formate was added dropwise and stirred at room temperature. Bubbles were generated within a few minutes, the reaction liquid became viscous and eventually solidified. Therefore, 2 ml of DMF was added and redissolved to obtain a transparent second mixed solution.
  • This mixed solution was reacted by stirring at room temperature in the presence of nitrogen gas for 17.5 hours to obtain a pale yellow transparent solution.
  • a solution of 2.2 mmol of bromomethylbutenolide dissolved in 1 ml of DMF was added to the light yellow transparent solution under ice cooling.
  • MeAcGR5 Chemical synthesis of MeAcGR5
  • one of the C-ring-cleavable GR5 derivatives was chemically synthesized by the following method.
  • FIG. 19 shows the MeAcGR5 synthesis process.
  • 2 mmol methyl acetate and 2.8 mmol sodium hydride were added to 1 ml DMF.
  • 9.8 mmol of methyl formate was added dropwise and stirred at room temperature. Bubbles were generated within a few minutes, the reaction liquid became viscous and eventually solidified. Therefore, 2 ml of DMF was added and redissolved to obtain a transparent mixed solution.
  • This mixed solution was reacted by stirring at room temperature in the presence of nitrogen gas for 17.5 hours to obtain a pale yellow transparent solution.
  • a solution of 2.2 mmol of bromomethylbutenolide dissolved in 1 ml of DMF was added to the pale yellow transparent solution under ice cooling.
  • the two geometric isomers were roughly separated by using a silica gel open column and stepwise elution with 12-21% acetone in hexane-acetone system, followed by preparative HPLC (Inertsil SIL100A, 40 ° C., 15% The peak was separated with ethanol-n-hexane (3.8 ml / min) and separated. Under these conditions, the trans isomer eluted after 10.3 minutes and the cis isomer eluted after 13.1 minutes.

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Abstract

L'invention concerne un composé qui a une activité inhibitrice de la ramification des plantes égale ou supérieure à celle d'une striglolactone, qui peut être synthétisé chimiquement à bon marché par un procédé simple, et qui a un effet promoteur faible ou nul sur la germination des semences de plantes du genre Striga. L'invention porte sur un inhibiteur de la ramification des plantes comprenant un composé représenté par la formule générale (1) ou un sel de celui-ci et une composition inhibitrice de la ramification des plantes comprenant l'inhibiteur de la ramification des plantes. Dans la formule générale (1), R1 et R2 représentent chacun indépendamment un atome d'hydrogène (H), un groupe alkyle inférieur, un groupe alcényle inférieur ou un groupe alcényle inférieur.
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WO2013140946A1 (fr) * 2012-03-19 2013-09-26 国立大学法人 神戸大学 Inhibiteur de germination de plantes parasites des racines, et procédé de lutte contre les plantes parasites des racines l'employant
WO2013174925A1 (fr) 2012-05-23 2013-11-28 Institut National De La Recherche Agronomique Nouveaux analogues de strigolactone et leur utilisation pour le traitement des plantes
JP2014501231A (ja) * 2010-12-14 2014-01-20 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト ストリゴラクタム誘導体および植物成長調節剤としてのこれらの使用
CN103864733A (zh) * 2013-10-15 2014-06-18 云南大学 一种丁烯酸内酯类代谢产物及其应用
CN104856988A (zh) * 2015-04-23 2015-08-26 暨南大学 一种独脚金内酯类似物在制备抗炎药物中的应用
WO2016193287A1 (fr) * 2015-06-04 2016-12-08 Syngenta Participations Ag Composés régulateurs de la croissance des plantes
WO2019003089A1 (fr) * 2017-06-26 2019-01-03 King Abdullah University Of Science And Technology Promoteur de croissance végétale ayant des activités de régulation des strigolactones
US20200354316A1 (en) * 2017-11-17 2020-11-12 Koch Biological Solutions, Llc Strigolactone derivatives
US11136292B2 (en) 2016-09-13 2021-10-05 Syngenta Participations Ag Plant growth regulator compounds
US11903386B2 (en) 2016-09-27 2024-02-20 King Abdullah University Of Science And Technology Strigolactone analogs and their usage in plant control

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MANGNUS, E. M. ET AL.: "Synthesis, structural characterization, and biological evaluation of all four enantiomers of strigol analog GR7", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 40, no. 4, 1992, pages 697 - 700 *
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JP2014501231A (ja) * 2010-12-14 2014-01-20 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト ストリゴラクタム誘導体および植物成長調節剤としてのこれらの使用
KR101825043B1 (ko) 2010-12-14 2018-02-02 신젠타 파티서페이션즈 아게 스트리고락탐 유도체 및 식물 생장 조절제로서 이의 용도
WO2013140946A1 (fr) * 2012-03-19 2013-09-26 国立大学法人 神戸大学 Inhibiteur de germination de plantes parasites des racines, et procédé de lutte contre les plantes parasites des racines l'employant
US9532569B2 (en) 2012-05-23 2017-01-03 Institut National De La Recherche Agronomique Strigolactone analogues and the use thereof for the treatment of plants
WO2013174925A1 (fr) 2012-05-23 2013-11-28 Institut National De La Recherche Agronomique Nouveaux analogues de strigolactone et leur utilisation pour le traitement des plantes
FR2990945A1 (fr) * 2012-05-23 2013-11-29 Agronomique Inst Nat Rech Nouveaux analogues de strigolactone et leur utilisation pour le traitement des plantes
US20150141255A1 (en) * 2012-05-23 2015-05-21 Institut National De La Recherche Agronomique New strigolactone analogues and the use thereof for the treatment of plants
CN103864733A (zh) * 2013-10-15 2014-06-18 云南大学 一种丁烯酸内酯类代谢产物及其应用
CN104856988A (zh) * 2015-04-23 2015-08-26 暨南大学 一种独脚金内酯类似物在制备抗炎药物中的应用
WO2016193287A1 (fr) * 2015-06-04 2016-12-08 Syngenta Participations Ag Composés régulateurs de la croissance des plantes
US11136292B2 (en) 2016-09-13 2021-10-05 Syngenta Participations Ag Plant growth regulator compounds
US11903386B2 (en) 2016-09-27 2024-02-20 King Abdullah University Of Science And Technology Strigolactone analogs and their usage in plant control
WO2019003089A1 (fr) * 2017-06-26 2019-01-03 King Abdullah University Of Science And Technology Promoteur de croissance végétale ayant des activités de régulation des strigolactones
US11399538B2 (en) 2017-06-26 2022-08-02 King Abdullah University Of Science And Technology Plant growth promoter with strigolactones regulation activities
US11839210B1 (en) 2017-06-26 2023-12-12 King Abdullah University Of Science And Technology Plant growth promoter with strigolactones regulation activities
US20200354316A1 (en) * 2017-11-17 2020-11-12 Koch Biological Solutions, Llc Strigolactone derivatives
US11787763B2 (en) 2017-11-17 2023-10-17 Plant Response, Inc. Strigolactone derivauves

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