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WO2017002898A1 - Régulateur de germination de striga - Google Patents

Régulateur de germination de striga Download PDF

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Publication number
WO2017002898A1
WO2017002898A1 PCT/JP2016/069392 JP2016069392W WO2017002898A1 WO 2017002898 A1 WO2017002898 A1 WO 2017002898A1 JP 2016069392 W JP2016069392 W JP 2016069392W WO 2017002898 A1 WO2017002898 A1 WO 2017002898A1
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WIPO (PCT)
Prior art keywords
group
compound
germination
striga
general formula
Prior art date
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Ceased
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PCT/JP2016/069392
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English (en)
Japanese (ja)
Inventor
雄一朗 土屋
大輔 浦口
ナラヤナン アルムガム ムルガン サティヤ
伸也 萩原
柾彦 吉村
俊則 木下
貴史 大井
健一郎 伊丹
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Nagoya University NUC
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Nagoya University NUC
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Priority claimed from JP2015132413A external-priority patent/JP2017014149A/ja
Priority claimed from JP2015132707A external-priority patent/JP6544768B2/ja
Application filed by Nagoya University NUC filed Critical Nagoya University NUC
Publication of WO2017002898A1 publication Critical patent/WO2017002898A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
    • A01M21/00—Apparatus for the destruction of unwanted vegetation, e.g. weeds
    • A01M21/04—Apparatus for destruction by steam, chemicals, burning, or electricity
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Definitions

  • the present invention relates to a striker germination regulating (induction or suppression) agent and a striker germination regulation method using the same. Furthermore, the present invention relates to a fluorescent probe that can easily and efficiently measure strigolactone receptor activity and a screening method for a striga germination regulator using the same.
  • Striga Plants belonging to the genus Striga (sometimes abbreviated as “Striga” in the present specification) parasitize major crops such as corn, rice, and legumes and cause poor growth.
  • the damage has spread to Africa, Asia, Australia, the United States, etc., and especially in Africa, the amount of damage is said to be 10 billion US dollars per year.
  • Striga seeds can survive in the soil for a long period of time, detect Strigolactone secreted from the roots of the surrounding host crops, germinate, and infest the roots of the host crops. And the seeds produced by the Striga plants that appeared on the ground also contaminate the surrounding soil. For this reason, once the soil is contaminated with the striker seed, if no countermeasures are taken, the striker will continue to be damaged in that soil, and the soil area contaminated with the seed will gradually expand. become.
  • striker germination control agent induction or suppression agent
  • soil contaminated with striker seed For example, if a striker germination inducer is applied in an environment where there is no host plant, the germinated striker will die without being parasitized, thereby purifying the soil. Moreover, if a striker germination inhibitor is applied, a host plant can be cultivated without being parasitized by striker. Therefore, development of a substance that induces or suppresses germination of striga more efficiently has been demanded.
  • Non-Patent Document 1 Striga germination regulators containing strigolactone and its derivatives as active ingredients have been developed (Non-Patent Document 1), but have not been put into practical use from the viewpoint of stability and synthesis cost.
  • An object of the present invention is to provide a striker germination regulator comprising a compound having a different basic skeleton from strigolactone and its derivatives as an active ingredient (problem 1).
  • Another object of the present invention is to provide a striker germination regulator comprising a compound having higher stability and that can be synthesized at a lower cost as an active ingredient.
  • an object of the present invention is to provide a method for screening a Striga germination regulator more simply and more efficiently without using Striga seeds (Problem 2).
  • the compound represented by the general formula (1) has Striga germination regulating activity. These compounds have high stability in an aqueous solution and can be produced at low cost.
  • the present inventors have found that the problem 2 can be solved by using the compound represented by the general formula (2) or (3) as a fluorescent probe. .
  • the present invention has been completed as a result of further research based on these findings. That is, the present invention includes the following aspects.
  • Invention 1 (Items 1 to 10) Item 1.
  • R 1 is an alkyl group; m is an integer from 0 to 3, R 2 represents a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, an optionally substituted alkenyl group, or an optionally substituted alkynyl.
  • a group an amino group which may be substituted with an alkyl group (however, when the number of substitutions is 2, the alkyl groups may be linked together to form a ring with an adjacent nitrogen atom), or a nitro group Yes, n is an integer from 0 to 5,
  • P is the general formula (P1) or (P2):
  • R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are hydrogen atoms or alkyl groups, and R 3 and R 4 Or R 5 and R 6 may be bonded to each other to form a benzene ring with an adjacent carbon atom, and R 8 and R 9 may be bonded to each other to form a benzene ring with an adjacent carbon atom.
  • a divalent group represented by Q is a group derived from an aromatic ring or a heterocyclic ring
  • Y is an oxygen atom or a sulfur atom
  • Z is General formula (Z1): —TU— (wherein T represents —S (O) i — (wherein i represents 1 or 2), —C ( ⁇ O) O—, Or -A (-NO 2 )-(wherein A represents a nitrogen-containing heterocyclic ring), and U is a single bond, -CH 2- , -O-, or -NR 10- (where R 10 Represents a hydrogen atom or an alkyl group.), Or a divalent group represented by general formula (Z2): —V—O—W— (in formula (Z2), V represents a single bond or — CH 2 — and W is a single bond, —C ( ⁇ O) —, or —S (O) k — (wherein k represents 1 or 2). It is a group. ] Striga
  • Item 2 The striker germination regulator according to Item 1, wherein Q is a group derived from benzene.
  • Item 3. The striker germination regulator according to Item 1 or 2, wherein Y is an oxygen atom.
  • Item 4. The striker germination regulator according to any one of Items 1 to 3, wherein m is 0.
  • Item 5 When P is a divalent group represented by the general formula (P1), Z is a divalent group represented by the general formula (Z1), and P is a divalent group represented by the general formula (P2). Item 5.
  • Item 6. The striker germination regulator according to any one of Items 1 to 5, which is a striker germination inducer.
  • Item 8. The striker germination regulator according to any one of Items 1 to 5, which is a striker germination inhibitor.
  • Item 10 A striga germination control method, wherein the striga germination regulator according to any one of items 1 to 9 is applied to soil containing striga seeds.
  • Invention 2 (Items 11 to 17) Item 11.
  • R 11 , R 12 , R 13 and R 14 are the same or different and are a hydrogen atom or an alkyl group, R 11 and R 12 may be bonded to each other to form an optionally substituted benzene ring with an adjacent carbon atom, R 13 and R 14 may be bonded to each other to form a benzene ring that may be substituted with an alkyl group together with the adjacent carbon atom;
  • R 15 is a hydrogen atom or an alkyl group
  • R 16 is an optionally protected hydroxyl group, alkoxy group, halogen atom, carboxyl group, alkoxycarbonyl group, isocyanate group, isothiocyanate group, sulfo group, or active ester group
  • R 17 , R 18 , R 19 and R 20 are the same or different and each is a hydrogen atom, a halogen atom or an alkyl group, p is 0 or an integer of 1 to 3.
  • Item 12. The compound according to Item 11, wherein one of R 11 and R 12 is a hydrogen atom and the other is an alkyl group, and one of R 13 and R 14 is a hydrogen atom and the other is an alkyl group, or a salt thereof, Hydrates or solvates.
  • Item 13 The compound according to Item 11 or 12, or a salt, hydrate or solvate thereof, wherein R 17 , R 18 , R 19 and R 20 are hydrogen atoms.
  • Item 14 The compound according to any one of Items 11 to 13, wherein p is 0, or a salt, hydrate or solvate thereof.
  • Item 15 A fluorescent probe comprising the compound according to any one of Items 11 to 14, or a salt, hydrate or solvate thereof.
  • Item 16 The fluorescent probe according to Item 15, which is used for measuring strigolactone receptor activity.
  • Screening method for Striga germination regulator comprising steps (a) to (c): (A) contacting the strigolactone receptor with the fluorescent probe according to Item 15 or 16 in the presence of a test substance; (B) After step (a), the fluorescence intensity of the decomposition product of the fluorescent probe is measured, and the fluorescence intensity (test fluorescence intensity) is the fluorescence intensity (control fluorescence intensity) when the test substance is not contacted. The step of comparing, (C) A step of selecting a test substance as a striker germination regulator when the test fluorescence intensity and the control fluorescence intensity are significantly different.
  • a striker germination regulator can be provided. Since the striker germination regulator of the present invention has high stability in an aqueous solution of an active ingredient, it can exert its effect stably over a long period of time after application to soil. Moreover, the active ingredient of the striker regulator of the present invention can be synthesized at a very low cost (about 120 yen per gram). Therefore, the striker regulator of the present invention is widely used all over the world, particularly in countries and regions (especially Africa, etc.) where the damage to the striker is serious but the countermeasures have not been sufficiently taken due to economic circumstances. It can be a countermeasure.
  • Invention 2 by using the compound represented by the general formula (2) or (3) as a fluorescent probe, a striga germination regulator can be obtained in a much simpler and more efficient manner than a conventional method for performing a germination test. Can be screened. In addition, since the germination test can be performed only in a licensed experimental space, the screening method of the present invention can be carried out without such restrictions. Furthermore, the obtained Striga germination regulator is improved more rationally through analysis of the interaction with the Strigolactone receptor found for the first time in the present invention, prediction of the optimum compound, etc. It is also possible.
  • the compound represented by the general formula (2) or (3) is hydrolyzed by the strigolactone receptor and exhibits the same physiological activity as strigolactone. And this compound produces
  • Example 3-1 The measurement result of the fluorescence intensity in an in-vitro fluorescence emission test (Example 3-1) is shown.
  • the horizontal axis indicates the time after the start of the reaction, and the vertical axis indicates the relative value of the fluorescence intensity.
  • Black circles show the results when Arabidopsis trigolactone receptor (AtD14) was added to the reaction system, and black triangles show the results when AtD14 was not added.
  • In vitro fluorescence test (Example 3-1) Fluorescence intensity measurements Linewaver-Burk plot was created based on the, and shows the K m value.
  • the result of having analyzed the component in the reaction solution of an in-vitro fluorescence emission test by LC-MS (Example 3-2) is shown.
  • the upper row shows the results when AtD14 was not added to the reaction system, and the lower row shows the results when AtD14 was added to the reaction system.
  • Fluorescein and D-ring (3-methyl-5-hydroxyfuran-2 (5H) -one) indicate degradation products generated by hydrolysis of the ether bond portion of YLG.
  • the number next to each peak indicates Retention time (minutes).
  • the measurement result of fluorescence intensity in a competitive test (Example 3-3) and the IC 50 value are shown.
  • the horizontal axis indicates the concentration of the competitor (GR24, carba-GR24, 5DS, or 4DO) in the reaction solution, and the vertical axis indicates the relative value of the fluorescence intensity.
  • the fluorescence observation image (upper stage) and bright field image (lower stage) in an in-vivo fluorescence emission test (Example 3-4) are shown.
  • the measurement result of the germination rate of a striker germination test (Example 4) is shown.
  • the horizontal axis indicates the concentration of GR24 or YLG in the solution containing seeds, and the vertical axis indicates the germination rate.
  • the bright field image (upper stage) and fluorescence observation image (lower stage) of the seed which germinated by the striker germination test (Example 4) are shown.
  • invention 1 The present invention relates to a general formula (1):
  • R 1 is an alkyl group; m is an integer from 0 to 3, R 2 represents a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, an optionally substituted alkenyl group, or an optionally substituted alkynyl.
  • a group an amino group which may be substituted with an alkyl group (however, when the number of substitutions is 2, the alkyl groups may be linked together to form a ring with an adjacent nitrogen atom), or a nitro group Yes, n is an integer from 0 to 5,
  • P is the general formula (P1) or (P2):
  • R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are hydrogen atoms or alkyl groups, and R 3 and R 4 Or R 5 and R 6 may be bonded to each other to form a benzene ring with an adjacent carbon atom, and R 8 and R 9 may be bonded to each other to form a benzene ring with an adjacent carbon atom.
  • a divalent group represented by Q is a group derived from an aromatic ring or a heterocyclic ring
  • Y is an oxygen atom or a sulfur atom
  • Z is General formula (Z1): —TU— (wherein T represents —S (O) i — (wherein i represents 1 or 2), —C ( ⁇ O) O—, Or -A (-NO 2 )-(wherein A represents a nitrogen-containing heterocyclic ring), and U is a single bond, -CH 2- , -O-, or -NR 10- (where R 10 Represents a hydrogen atom or an alkyl group.),
  • the alkyl group represented by R 1 may be either linear or branched, but is preferably linear.
  • the alkyl group has, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 to 2.
  • Examples of the alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n- Examples include a hexyl group and a 3-methylpentyl group.
  • m is an integer of 0 to 3. m is preferably 0 or 1, more preferably 0.
  • examples of the halogen atom represented by R 2 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • a bromine atom, an iodine atom, etc. are mentioned, More preferably, a bromine atom is mentioned.
  • the optionally substituted alkyl group represented by R 2 is not particularly limited, and may be a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), oxo group, phenyl group.
  • halogen atom fluorine atom, chlorine atom, bromine atom, iodine atom, etc.
  • oxo group phenyl group.
  • examples thereof include a linear or branched alkyl group having 1 to 8, preferably 1 to 6, more preferably 1 to 4 carbon atoms which may be substituted with, for example.
  • the number of substituents is not particularly limited and is, for example, 0 to 6, preferably 0 to 3.
  • Examples of such an optionally substituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, and a perfluoro group.
  • a methyl group, a perfluoroethyl group, etc. are mentioned.
  • the optionally substituted alkoxy group represented by R 2 is not particularly limited, and may be a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), oxo group, phenyl group.
  • halogen atom fluorine atom, chlorine atom, bromine atom, iodine atom, etc.
  • oxo group phenyl group.
  • examples thereof include a linear or branched alkoxy group having 1 to 8, preferably 1 to 6, more preferably 1 to 4 carbon atoms which may be substituted with, for example.
  • the number of substituents is not particularly limited and is, for example, 0 to 6, preferably 0 to 3.
  • Examples of such an optionally substituted alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, a peroxy group, and the like.
  • a fluoromethoxy group, a perfluoroethoxy group, etc. are mentioned.
  • the optionally substituted alkylthio group represented by R 2 is not particularly limited, and may be a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), oxo group, phenyl group.
  • halogen atom fluorine atom, chlorine atom, bromine atom, iodine atom, etc.
  • oxo group phenyl group.
  • examples thereof include a linear or branched alkylthio group having 1 to 8, preferably 1 to 6, and more preferably 1 to 4 carbon atoms which may be substituted with, for example.
  • the number of substituents is not particularly limited and is, for example, 0 to 6, preferably 0 to 3.
  • Examples of such an optionally substituted alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a sec-butylthio group, a t-butylthio group, A perfluoromethylthio group, a perfluoroethylthio group, etc. are mentioned.
  • the optionally substituted alkenyl group represented by R 2 is not particularly limited, and is a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), oxo group, phenyl group. And a straight or branched alkenyl group having 2 to 8, preferably 2 to 6, and more preferably 2 to 4 carbon atoms which may be substituted with an alkyl group.
  • the number of substituents is not particularly limited and is, for example, 0 to 6, preferably 0 to 3.
  • Examples of such an optionally substituted alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, an isopropenyl group, a butenyl group, a pentenyl group, and a hexenyl group.
  • the optionally substituted alkynyl group represented by R 2 is not particularly limited, and may be a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), oxo group, phenyl group. And a linear or branched alkynyl group having 2 to 8, preferably 2 to 6, and more preferably 2 to 4 carbon atoms, which may be substituted with, for example.
  • the number of substituents is not particularly limited and is, for example, 0 to 6, preferably 0 to 3.
  • alkynyl group examples include ethynyl group, propynyl group, butynyl group, pentynyl group, hexynyl group, phenylacetinyl group and the like.
  • the amino group which may be substituted with the alkyl group represented by R 2 is not particularly limited, and has a straight or branched carbon number of 1 to 6, preferably 1 to 4. More preferred is an amino group which may be substituted with 1 to 2 alkyl groups.
  • the number of substitution with an alkyl group is preferably 1 to 2 (when the number of substitution is 2, the alkyl groups may be linked to form a ring with the adjacent nitrogen atom).
  • Examples of such an optionally substituted amino group include an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, and an ethylmethylamino group.
  • n is an integer of 0 to 5.
  • m is preferably 0 to 3, more preferably 1 to 3.
  • P is a divalent group represented by general formula (P1) or (P2).
  • P is preferably a divalent group represented by the general formula (P2) from the viewpoint that higher Striga germination-inducing activity or Striga germination-inhibiting activity can be obtained.
  • n is preferably 0, or n is an integer of 1 to 5 and R 2 is an alkyl group or an alkoxy group which may be substituted with a phenyl group, and still more preferably n is 0, or n is an integer of 1 to 3, and R 2 is an alkyl group which may be substituted with a phenyl group.
  • the alkyl group represented by R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 may be either linear or branched. A linear one is preferred.
  • the alkyl group has, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 to 2.
  • alkyl group examples include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n- Examples include a hexyl group and a 3-methylpentyl group.
  • R 3 and R 4 or R 5 and R 6 may be bonded to each other to form a benzene ring together with adjacent carbon atoms, and R 8 and R 9 may be bonded to each other together with adjacent carbon atoms.
  • a benzene ring may be formed.
  • R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are all hydrogen atoms.
  • the group derived from the aromatic ring or heterocyclic ring represented by Q is not particularly limited as long as it is a group obtained by removing one or more hydrogens from the aromatic ring or heterocyclic ring.
  • Q has a valence that varies depending on the number of n. That is, for example, when n is 0, Q is a monovalent group, and when n is 1, Q is a divalent group.
  • the aromatic ring is not particularly limited, but preferably has 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms.
  • Examples of such an aromatic ring include benzene, indene, naphthalene, anthracene, tetracene, pyrene, perylene, fluorene, phenanthrene, and the like, preferably benzene and naphthalene, and more preferably benzene.
  • the heterocyclic ring is preferably monocyclic, bicyclic, or tricyclic, and more preferably monocyclic (especially a 5- or 6-membered ring) or bicyclic (especially a condensed ring of 5-membered and 6-membered rings). preferable.
  • a nitrogen atom, an oxygen atom, a sulfur atom and the like are preferable, and a nitrogen atom, an oxygen atom and the like are more preferable.
  • pyrrolidine tetrahydrofuran, tetrahydrothiophene, pyrrole, furan, thiophene, piperidine, tetrahydropyran, tetrahydrothiopyran, imidazole, pyridine, pyrazole, oxazole, thiazole, imidazoline, pyrazine, morpholine, thiazine, etc .; these monocyclic A ring formed by condensing two or more heterocycles; and a ring formed by condensing these monocyclic heterocycles and aromatic rings (particularly benzene rings).
  • Y is an oxygen atom or a sulfur atom, preferably an oxygen atom.
  • Z is a divalent group represented by general formula (Z1) or a divalent group represented by general formula (Z2).
  • P is a divalent group represented by the general formula (P1)
  • Z is a divalent group represented by the general formula (Z1)
  • P is a divalent group represented by the general formula (P2).
  • Z is a divalent group represented by the general formula (Z2).
  • T represents —S (O) i — (where i represents 1 or 2, preferably 2), —C ( ⁇ O) O—, or —A (—NO 2 )-(Wherein A represents a nitrogen-containing heterocycle), preferably —S (O) i — or —C ( ⁇ O) O—, more preferably —S (O) i —. is there.
  • A represents a nitrogen-containing heterocycle
  • the nitrogen-containing heterocycle represented by A is the same as the heterocycle from which the group Q is derived except that it is essential to contain nitrogen.
  • U is a single bond, —CH 2 —, —O—, or —NR 10 — (wherein R 10 represents a hydrogen atom or an alkyl group), preferably a single bond, —CH 2 — or —NR 10 —, more preferably a single bond or —CH 2 —.
  • R 10 represents a hydrogen atom or an alkyl group
  • the alkyl group represented by R 10 is the same as the alkyl group represented by R 1 .
  • divalent group represented by the general formula (Z1) include the following groups.
  • V represents a single bond or —CH 2 —, and preferably —CH 2 —.
  • W represents a single bond, —C ( ⁇ O) —, or —S (O) k — (wherein k represents 1 or 2).
  • divalent group represented by the general formula (Z2) include the following groups.
  • Specific examples of the compound represented by the general formula (1) include compounds 1 to 41 described in Examples described later.
  • the compound represented by the general formula (1) is preferably Compound 1, 3 to 6, 8 to 9, 11 to 13, 15, 31 to 34, 36 to 37, 39 from the viewpoint of higher Striga germination inducing activity.
  • 41 to 42, etc. more preferably 3 to 4, 12, 31 to 33, 36 to 37, 39, and 41, and still more preferably compounds 31 and 36. Therefore, they are particularly suitable as an active ingredient of a striker germination inducer.
  • the compounds represented by the general formula (1) are preferably compounds 2, 4 to 14, 16 to 19, 29 to 30, 38, 40, etc., more preferably from the viewpoint of higher striga germination inhibitory activity.
  • Compounds 6, 14, 16, 19, 29, 38, etc. are mentioned, More preferably, compounds 14, 38, etc. are mentioned. Therefore, they are particularly suitable as an active ingredient of a striker germination inhibitor.
  • the compounds represented by the general formula (1) are preferably compounds 5 to 6, 8 to 9, 11 to 13 and the like from the viewpoint of exhibiting relatively high activity in both striga germination inducing activity and striga germination inhibition activity. It is done.
  • the salt of the compound represented by the general formula (1) is not particularly limited, and any of an acid salt and a basic salt can be employed.
  • acid salts include inorganic acid salts such as hydrochloride, hydrobromide, sulfate, nitrate, phosphate, acetate, propionate, tartrate, fumarate, maleate, malic acid
  • basic salts include alkali metal salts such as sodium and potassium, and alkaline earth metals such as calcium salts and magnesium salts. A metal salt etc. are mentioned.
  • the solvate of the compound represented by the general formula (1) is not particularly limited as long as it is a solvate of the compound represented by the general formula (1) or a salt thereof and a solvent.
  • the solvent include ethanol, glycerol, acetic acid and the like.
  • the compound represented by the general formula (1) can be produced according to or according to a known synthesis method. As an example, the synthesis method by the following process 1 or process 2 is mentioned.
  • step 1 compound c included in the compound represented by formula (1) is synthesized by reacting compound a and compound b in the presence of a catalyst.
  • step 2 compound f included in the compound represented by formula (1) is synthesized by reacting compound d and compound e in the presence of a catalyst.
  • the amount of compound b used is usually preferably 0.2 to 2 mol, more preferably 0.5 to 1.5 mol, relative to 1 mol of compound a, from the viewpoints of selectivity and yield.
  • the amount of compound e used is usually preferably 0.2 to 2 mol, more preferably 0.5 to 1.5 mol, relative to 1 mol of compound d, from the viewpoints of selectivity and yield. .
  • the catalyst used in Steps 1 and 2 is not particularly limited, and examples thereof include a base catalyst such as triethylamine from the viewpoints of selectivity, yield, and safety.
  • a catalyst may be used independently and may be used together.
  • the amount of the catalyst used is not particularly limited as long as the target compound is obtained.
  • the amount is usually preferably 0.2 to 3 mol, more preferably 0.5 to 2.0 mol, relative to 1 mol of compound a.
  • Steps 1 and 2 are usually performed in a reaction solvent.
  • the reaction solvent that can be used include dichloromethane, N, N-dimethylformamide, acetonitrile, tetrahydrofuran, acetone, toluene and the like, preferably dichloromethane and the like.
  • a solvent may be used independently and may be used together.
  • reaction solvents organic solvents
  • concentration of compound a or d is 0.005 to 1 mol / L, preferably 0.01 to Adjust to 0.5 mol / L.
  • the reaction temperature in steps 1 and 2 can be carried out under heating, at room temperature, or under cooling, and is usually preferably about 0 to 50 ° C.
  • the reaction may be carried out at normal pressure, and if necessary, may be carried out under reduced pressure or pressurized conditions, but is preferably carried out under normal pressure.
  • the progress of the reaction can be followed by conventional methods such as chromatography. After completion of the reaction, the solvent is distilled off, and the product can be isolated and purified by usual methods such as chromatography and recrystallization.
  • the structure of the product can be identified by elemental analysis, MS (FD-MS) analysis, IR analysis, 1 H-NMR, 13 C-NMR and the like.
  • the compounds c and f synthesized in the steps 1 and 2 can be purified by an ordinary purification method such as activated carbon treatment, recrystallization, column chromatography, or the like, if necessary.
  • the compound represented by the general formula (1) follows a method in which these steps are combined with a known substitution reaction, addition reaction, or the like, or a method described in Examples described later. Alternatively, it can be produced by a similar method or the like.
  • the compound represented by the general formula (1) has a striga germination regulating action. Therefore, the compound represented by the general formula (1), or a salt, hydrate or solvate thereof can be used as an active ingredient of a striker germination regulator.
  • “regulation” of striker germination indicates induction of striker germination or suppression of striker germination.
  • a compound having a striga germination inducing action, or a salt, hydrate or solvate thereof is used as an active ingredient of a striga germination inducer among striga germination regulators.
  • a striga germination inducer among striga germination regulators.
  • the striker germination inducer is applied in an environment where the plant serving as the striker's host is not present in the vicinity, the germinated striker cannot die and die, thereby purifying the soil.
  • a compound having a striga germination inhibitory action or a salt, hydrate or solvate thereof is used as an active ingredient of a striga germination inhibitor among striga germination regulators.
  • the striga germination inhibitor is applied, for example, in the growth environment of the plant that is the striker host, the host plant can be cultivated without being parasitized by the striker.
  • the plant serving as the striker host there are no particular restrictions on the plant serving as the striker host, and examples include corn, millet, sorghum, sugar cane, rice, and beans.
  • the target striker is not particularly limited and may be a known striker.
  • the agent of the present invention may consist only of the active ingredient (the compound represented by the general formula (1), or a salt, hydrate or solvate thereof), but in addition to these, the dosage form and the application mode Various additives may be included depending on the like.
  • the content ratio of the active ingredient in the agent of the present invention is not particularly limited. Specifically, the amount is about 0.0001 to 100% by weight, preferably about 0.01 to 50% by weight.
  • the dosage form of the agent of the present invention is not particularly limited as long as it is an agriculturally acceptable dosage form.
  • liquid agent, solid agent, powder agent, granule, granule, wettable powder, flowable agent, emulsion, paste agent, dispersant and the like can be mentioned.
  • the additive is not particularly limited as long as it is an agriculturally acceptable additive.
  • examples include carriers, surfactants, thickeners, extenders, binders, vitamins, antioxidants, pH adjusters, volatilization inhibitors, and dyes.
  • the application mode of the agent of the present invention is not particularly limited as long as it is a mode in which the active ingredient and the striker seed can come into contact with each other.
  • coating, mixing, etc. of the agent of this invention to the soil containing a striker seed is mentioned.
  • R 11 , R 12 , R 13 and R 14 are the same or different and are a hydrogen atom or an alkyl group, R 11 and R 12 may be bonded to each other to form an optionally substituted benzene ring with an adjacent carbon atom, R 13 and R 14 may be bonded to each other to form a benzene ring that may be substituted with an alkyl group together with the adjacent carbon atom;
  • R 15 is a hydrogen atom or an alkyl group
  • R 16 is an optionally protected hydroxyl group, alkoxy group, halogen atom, carboxyl group, alkoxycarbonyl group, isocyanate group, isothiocyanate group, sulfo group, or active ester group
  • R 17 , R 18 , R 19 and R 20 are the same or different and each is a hydrogen atom, a halogen atom or an alkyl group, p is 0 or an integer of 1 to 3.
  • Or a salt, hydrate or solvate thereof
  • R 11 , R 12 , R 13 and R 14 are the same or different and are a hydrogen atom or an alkyl group, and R 11 and R 12 may be bonded to each other and substituted with an alkyl group together with adjacent carbon atoms.
  • a good benzene ring may be formed, and R 13 and R 14 may be bonded to each other to form a benzene ring which may be substituted with an alkyl group together with an adjacent carbon atom.
  • the alkyl group represented by R 11 , R 12 , R 13 or R 14 may be either linear or branched, but is preferably linear.
  • the alkyl group has, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 to 2.
  • Examples of the alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n- Examples include a hexyl group and a 3-methylpentyl group.
  • the alkyl group that may be substituted on the benzene ring formed by R 11 and R 12 or R 13 and R 14 is the same as the above-mentioned “alkyl group represented by R 11 , R 12 , R 13, or R 14 ”.
  • the number of substitution on the benzene ring is not particularly limited, but is, for example, 0 to 3, preferably 0 to 1.
  • R 11 , R 12 , R 13 and R 14 are preferably R 11 and R 12 from the viewpoint of being closer to the structure of strigolactone (that is, more easily accepted by the strigolactone receptor).
  • R 13 and R 14 do not form an optionally substituted benzene ring, more preferably one of R 11 and R 12 is a hydrogen atom and the other is an alkyl group, and R 13 and One of R 14 is a hydrogen atom and the other is an alkyl group, more preferably R 11 and R 13 are hydrogen atoms, and R 12 and R 14 are alkyl groups.
  • R 15 is a hydrogen atom or an alkyl group.
  • the alkyl group represented by R 15 may be either linear or branched, but is preferably linear.
  • the alkyl group has, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 3 carbon atoms.
  • Examples of the alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n- Examples include a hexyl group and a 3-methylpentyl group.
  • R 15 is preferably an alkyl group from the viewpoint of easier synthesis of the compound of the present invention.
  • R 16 is an optionally protected hydroxyl group, alkoxy group, halogen atom, carboxyl group, alkoxycarbonyl group, isocyanate group, isothiocyanate group, sulfo group, or active ester group.
  • Examples of the protecting group for the optionally protected hydroxyl group represented by R 16 include alkoxyalkyl groups such as methoxymethyl group (MOM), alkanoyl groups such as 2-tetrahydropyranyl (THP) group, and acetyl group (Ac). Groups and the like.
  • alkoxyalkyl groups such as methoxymethyl group (MOM)
  • alkanoyl groups such as 2-tetrahydropyranyl (THP) group
  • Ac acetyl group
  • Examples of the alkoxy group represented by R 16 include linear or branched C1-6 (particularly 1 to 3) alkoxy groups, and specific examples include a methoxy group, an ethoxy group, and an n-propyloxy group. And isopropyloxy group.
  • Examples of the halogen atom represented by R 16 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • alkoxycarbonyl group represented by R 16 examples include linear or branched (C1) such as methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, tert-butyloxycarbonyl group and the like. ⁇ 6 alkoxy group) carbonyl group.
  • the active ester group represented by R 16 is a group in which a carboxyl group (—COOH) is converted into a highly reactive active ester.
  • an active ester group using N-hydroxysuccinimide for example, — C ( ⁇ O) OSu: Su is a succinimide group
  • a group obtained by making a carboxylic acid a mixed acid anhydride for example, —C ( ⁇ O) OC ( ⁇ O) R: R is a C1-C6 alkyl group
  • an imidazolide group using carbonylimidazole (CDI) for example, —C ( ⁇ O) —Im: Im is 1-imidazolyl group.
  • P is not particularly limited, but is, for example, 0 or an integer of 1 to 3, preferably 0 or 1, and more preferably 0.
  • R 17 , R 18 , R 19 and R 20 are the same or different and each represents a hydrogen atom, a halogen atom or an alkyl group.
  • Examples of the halogen atom represented by R 17 , R 18 , R 19 and R 20 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom.
  • the alkyl group represented by R 17 , R 18 , R 19 and R 20 may be either linear or branched, but is preferably linear.
  • the alkyl group has, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 to 2.
  • Examples of the alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, neopentyl group, n- Examples include a hexyl group and a 3-methylpentyl group.
  • R 17 , R 18 , R 19 and R 20 , R 17 and R 19 are preferably the same or different from each other in terms of being more easily accepted by the strigolactone acceptor, and preferably a hydrogen atom, a halogen atom, or an alkyl
  • R 18 and R 20 are hydrogen atoms, and more preferably, R 17 , R 18 , R 19 and R 20 are all hydrogen.
  • the compound of the present invention is preferably a compound represented by the general formula (3) from the viewpoint of stability and the like.
  • the salt of the compound of the present invention is not particularly limited, and either an acidic salt or a basic salt can be employed.
  • acid salts include inorganic acid salts such as hydrochloride, hydrobromide, sulfate, nitrate, phosphate, acetate, propionate, tartrate, fumarate, maleate, malic acid
  • basic salts include alkali metal salts such as sodium and potassium, and alkaline earth metals such as calcium salts and magnesium salts. A metal salt etc. are mentioned.
  • the solvate of the compound of the present invention is not particularly limited as long as it is a solvate of the compound represented by the general formula (2) or (3) or a salt thereof and a solvent.
  • the solvent include ethanol, glycerol, acetic acid and the like.
  • the compound represented by the general formula (2) or (3) can be produced according to or according to a known synthesis method such as Williamson's ether synthesis method or Ullman's ether synthesis method. As an example, it can be synthesized by the following scheme.
  • step (I) compound i (compound represented by formula (2)) is synthesized by a step of reacting compound g and compound h in the presence of a catalyst.
  • step (II) compound k (compound represented by general formula (3)) is synthesized by a step of reacting compound j and compound h in the presence of a catalyst.
  • the amount of compound h used is usually preferably 0.2 to 2 mol, preferably 0.5 to 1.5 mol, relative to 1 mol of compound g, from the viewpoints of selectivity and yield. More preferred.
  • the amount of compound h used is usually preferably 2 to 5 mol, more preferably 2.5 to 4 mol, relative to 1 mol of compound j, from the viewpoints of selectivity and yield.
  • potassium carbonate, silver (I) oxide, a pyridine, copper examples thereof include copper (II) oxide and sodium hydride, preferably a base catalyst, and more preferably potassium carbonate, silver (I) oxide, pyridine and the like. These may be used alone or in combination.
  • potassium carbonate is preferable as the catalyst used in step (I)
  • a combination of silver (I) oxide and pyridine is preferable as the catalyst used in step (II).
  • the amount of the catalyst used is not particularly limited as long as the target compound is obtained, and can be appropriately set according to the step and the type of catalyst.
  • the amount is usually preferably 0.2 to 2 moles relative to 1 mole of compound g, 0.5 to 1. 5 moles is more preferred.
  • silver oxide is used in step (II), from the viewpoint of selectivity and yield, it is usually preferably 2 to 5 mol, preferably 2.5 to 4 mol, relative to 1 mol of compound j. More preferred.
  • Steps (I) and (II) are usually performed in a reaction solvent.
  • the reaction solvent that can be used include N, N-dimethylformamide, acetonitrile, dichloromethane, tetrahydrofuran, acetone, toluene and the like, preferably N, N-dimethylformamide, acetonitrile and the like. These may be used alone or in combination.
  • reaction solvents organic solvents
  • concentration of compound g or j is 0.01 to 1 mol / L, preferably 0.05 to It is preferable to adjust so that it may become 0.5 mol / L.
  • reaction temperature in steps (I) and (II) can be carried out under heating, at room temperature, or under cooling, and is usually preferably about 10 to 50 ° C.
  • the reaction may be carried out at normal pressure, and if necessary, may be carried out under reduced pressure or pressurized conditions, but is preferably carried out under normal pressure.
  • the progress of the reaction can be followed by conventional methods such as chromatography. After completion of the reaction, the solvent is distilled off, and the product can be isolated and purified by usual methods such as chromatography and recrystallization.
  • the structure of the product can be identified by elemental analysis, MS (FD-MS) analysis, IR analysis, 1 H-NMR, 13 C-NMR and the like.
  • the compounds i and k synthesized in the steps (I) and (II) can be purified by an ordinary purification method such as activated carbon treatment, recrystallization, column chromatography or the like, if necessary.
  • the compound g or j has a hydroxyl group other than the hydroxyl group on the xanthene skeleton, the other hydroxyl group is protected with an appropriate protecting group as necessary, and then the step (I) or (II) is performed.
  • the compound i or k can also be synthesized by removing the protecting group after completion of the reaction.
  • Fluorescent probe A fluorescent probe containing the compound of the present invention, or a salt, hydrate or solvate thereof (hereinafter, sometimes referred to as “fluorescent probe of the present invention”) will be described.
  • the compound of the present invention is hydrolyzed by the strigolactone receptor and exhibits the same physiological activity as strigolactone. And the compound of this invention produces
  • the fluorescent probe may be composed only of the compound of the present invention, or a salt, hydrate or solvate thereof, as long as the activity as a fluorescent probe is not impaired, It may contain components.
  • the concentration of the compound of the present invention, or a salt, hydrate or solvate thereof can be appropriately adjusted depending on the purpose of use and is not particularly limited, but may be a case where it acts on a plant. Examples include 1 ⁇ 10 ⁇ 10 mole / L to 1 ⁇ 10 ⁇ 3 mole / L, preferably 1 ⁇ 10 ⁇ 8 mole / L to 1 ⁇ 10 ⁇ 4 mole / L, and accept strigolactone in vitro.
  • the solvent is not particularly limited, and any of a polar solvent and a nonpolar solvent can be used.
  • polar solvents examples include ether compounds (tetrahydrofuran, anisole, 1,4-dioxane, cyclopentyl methyl ether, etc.), alcohols (methanol, ethanol, allyl alcohol, etc.), ester compounds (ethyl acetate, etc.), ketones (acetone, etc.) Halogenated hydrocarbons (dichloromethane, chloroform), dimethyl sulfoxide, amide solvents (N, N-dimethylformamide, dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, N-methylpyrrolidone, etc.) .
  • ether compounds tetrahydrofuran, anisole, 1,4-dioxane, cyclopentyl methyl ether, etc.
  • alcohols methanol, ethanol, allyl alcohol, etc.
  • ester compounds ethyl acetate, etc.
  • ketones acetone, etc.
  • Halogenated hydrocarbons
  • nonpolar solvent examples include aliphatic organic solvents such as pentane, hexane, cyclohexane and heptane; aromatic solvents such as benzene, toluene, xylene and mesitylene.
  • the buffer is not particularly limited, and examples thereof include hepes buffer, tris buffer, tricine-sodium hydroxide buffer, phosphate buffer, and phosphate buffered saline.
  • Striga germination regulator screening method A Striga germination regulator screening method (hereinafter also referred to as “the screening method of the present invention”) comprising the following steps (a) to (c) will be described: (A) contacting the strigolactone receptor with the fluorescent probe according to claim 5 or 6 in the presence of a test substance; (B) After step (a), the fluorescence intensity of the decomposition product of the fluorescent probe is measured, and the fluorescence intensity (test fluorescence intensity) is the fluorescence intensity (control fluorescence intensity) when the test substance is not contacted. The step of comparing, (C) A step of selecting a test substance as a striker germination regulator when the test fluorescence intensity and the control fluorescence intensity are significantly different.
  • the striga germination regulating substance is a substance that acts on the seed of striga and regulates (induces or suppresses) germination of the seed.
  • the germination inducer When the germination inducer is applied in an environment where there is no host plant, the germinated striga cannot die and die (so-called suicide germination), so that the soil can be purified.
  • the host plant can be cultivated without being parasitized by the striker.
  • the test substance is a target substance to be screened for whether or not it is a striga germination regulating substance.
  • the test substance can be widely used regardless of a naturally occurring compound or an artificially produced compound.
  • the composition which mixed not only the refined compound but various compounds, and the extract of animals and plants can also be used.
  • the strigolactone receptor is not particularly limited as long as it is a receptor having an activity of accepting strigolactone and hydrolyzing an ether bond portion thereof.
  • the strigolactone receptor include AtD14 which is a strigolactone receptor of Arabidopsis thaliana, a strigolactone-derived strigolactone receptor, and the like, preferably a strigalactone-derived receptor.
  • Striga-derived strigolactone receptors have been found for the first time in the present invention. For example, SEQ ID NOs: 2 to 11, preferably SEQ ID NOs: 2, 4 to 8, 10, and 10, more preferably 5, 6, And a protein consisting of the amino acid sequence represented by 8 and 8.
  • the mode of contacting the strigolactone receptor and the fluorescent probe of the present invention in the presence of the test substance is not particularly limited as long as these three components can be contacted.
  • mixing these three components in a suitable solvent can be mentioned.
  • the contact time is not particularly limited as long as the compound of the present invention is hydrolyzed by the strigolactone receptor.
  • the contact time is preferably such that a specific fluorescent substance generated by hydrolysis is accumulated to such an extent that fluorescence can be detected, for example, 5 minutes to 3 hours, preferably about 30 to 90 minutes.
  • Fluorescence intensity can be measured according to or according to a known method. From the viewpoint of carrying out more simply and efficiently, a system in which the contact is performed in the well of the microplate and the fluorescence intensity is measured with a fluorescence microplate reader is preferable.
  • test substance is not contacted is the case where the same or equivalent treatment is performed except that the test substance is not contacted in the step (a).
  • the fluorescence intensity in this case can also be measured in the same manner as the fluorescence intensity when brought into contact with the aforementioned test substance.
  • test fluorescence intensity and the control fluorescence intensity are significantly different may be determined based on a certain standard, for example, a statistical standard. Specifically, a method of determining a significant difference when the P value is obtained by measuring a plurality of times and the P value is not more than a certain value, for example, not more than 0.05, may be mentioned.
  • the strigolactone receptor activity is regulated (activated or inhibited) by the test substance, for example, the test substance is a strigolactone receptor agonist or It means functioning as an antagonist. Since striga germination is controlled by strigolactone, in this case, the test substance can be selected as a striga germination regulator.
  • the Striga germination regulator selected in this manner may be used as a candidate substance for a human hematopoietic stem cell proliferation regulator as a test substance for secondary screening.
  • SA formula
  • SB formula
  • RX 4-bromobenzene-1-sulfonyl chloride
  • OTf represents a trifluoromethanesulfonate ion (the same applies to the following schemes).
  • Acetonitrile (5 mL) was added to a mixture of furan-2-yl (piperazin-1-yl) methanone (3) (228 mg, 1.27 mmol) and triflate salt (5r) (551 mg, 1.52 mmol) at room temperature. Stir for hours. The solvent was evaporated, and the crude reaction mixture was purified by silica gel column chromatography (eluent: hexane / ethyl acetate mixed solvent) to obtain the desired product (compound 28) as a sticky solid (152 mg, yield 39%). ).
  • Example 2 Analysis of the effect on striga germination Using compounds 1-42 as test compounds, a striga germination induction test and a striga germination inhibition test were conducted.
  • the striga germination induction test was carried out by measuring the germination rate in the same manner as in Example 1 except that the final concentration of the test compound was 0.1, 1, or 10 ⁇ M.
  • the striga germination inhibition test germination was carried out in the same manner as in Example 1 except that the final concentration of the test compound was 0.1, 1, or 10 ⁇ M, and synthetic strigolactone was added to the final concentration of 0.1 ⁇ M together with the test compound. This was done by measuring the rate. Table 1 shows the average germination rate for some test compounds.
  • the control indicates a case where there is no test compound.
  • Compounds 1, 3-6, 8-9, 11-13, 15, 31-34, 36-37, 39 and 41-42 show relatively high Striga germination-inducing activity, among which compounds 3-4, 12, 31 ⁇ 33, 36-37, 39 and 41 showed higher Striga germination-inducing activity, and compounds 31 and 36 showed particularly high Striga germination-inducing activity.
  • compounds 2, 4-14, 16-19, 29-30, 38 and 40 show a relatively high striga germination inhibitory activity, among which compounds 6, 14, 16, 19, 29 and 38 have a higher striga germination inhibition activity.
  • the compounds 14 and 38 showed particularly high striga germination inhibitory activity.
  • Compounds 5-6, 8-9 and 11-13 showed relatively high activity in both Striga germination-inducing activity and Striga germination-inhibiting activity. It was also confirmed that compounds not shown in Table 1 (compounds 20 to 28) also exhibited Striga germination-inducing activity or Striga germination-inhibiting activity.
  • Ethyl 2- (6-hydroxy-3-oxo-3H-xanthen-9-yl) benzoate (227.0 mg, 0.63 mmol, 1.00 equiv) and K 2 CO 3 (152 mg, 0.69 mmol, 1.10 equiv) were replaced with N, N -Dimethylformamide (DMF) (2.0 mL) was added and stirred at room temperature for 10 minutes.
  • DMF N, N -Dimethylformamide
  • 5-Bromo-3-methylfuran-2 (5H) -one 136.1 mg, 0.63 mmol, 1.00 equiv was added thereto, and the mixture was stirred at room temperature for 30 minutes. Water was added thereto, and the aqueous layer was extracted with ethyl acetate.
  • Example 3 Hydrolysis and fluorescence of strigolactone by Arabidopsis thaligolactone receptor are hydrolyzed by strigolactone receptor in plants such as Arabidopsis thaliana, thereby controlling plant life phenomena (branch inhibition, etc.) It is known. Therefore, it was examined whether the same phenomenon occurred in the compound synthesized in the above synthesis example (test compound).
  • the test compound is designed so that a fluorescent substance (fluorescein derivative) is generated by hydrolysis of the ether bond. Specifically, it was performed as follows.
  • Arabidopsis trigolactone receptor was produced according to a conventional method. Specifically, the receptor cDNA was obtained by RT-PCR and expressed and purified in E. coli. The obtained Arabidopsis trigolactone receptor (recombinant AtD14, 1 ⁇ g) and test compound (YLG, YLG2, YLG3, YLG4, YLG5, YLGW, or YLGW-F) (final concentrations 0.2 ⁇ M, 0.4 ⁇ M, 0.6 ⁇ M, 1 ⁇ M) , 5 ⁇ M, or 10 ⁇ M) was prepared, and 100 ⁇ L of a reaction solution (100 mM HEPES, 150 mM NaCl, pH 7.0, 0.1% DMSO) was prepared and reacted in a 96 black well plate (Greiner).
  • a reaction solution 100 mM HEPES, 150 mM NaCl, pH 7.0, 0.1% DMSO
  • FIG. 1 shows the measurement results of the fluorescence intensity when YLG is used as a test compound at a final concentration of 1 ⁇ M. Furthermore, a Linewaver-Burk plot was created based on the measurement result of the fluorescence intensity after 60 minutes from the start of the reaction, and the K m value was calculated.
  • FIG. 2 shows the plot and K m value when YLG is used as the test compound.
  • fluorescence emission occurred by the YLG treatment in the wild strain, but no fluorescence emission occurred in the strigolactone-insensitive strain. Moreover, the fluorescence emission site
  • the 0.2 mL tube was transferred to a new 15 mL conical tube filled with liquid medium containing YLG (final concentration 5 ⁇ M) or DMSO and cultivated for 2 weeks.
  • the number of branches when the wild-type strain was not treated with YLG was 0.5 ⁇ 0.6
  • the number of branches when the strigolactone biosynthesis mutant was not treated with YLG was 2.8 ⁇ 0.5.
  • the ton biosynthesis mutant was treated with YLG, the number of branches was 1.3 ⁇ 0.6. This suggests that YLG has a function to return to normal branching abnormalities (increase in the number of branches) due to strigolactone biosynthesis mutation, that is, it has the same function as strigolactone in Arabidopsis thaliana. .
  • Example 4 Striga Germination Test Striga seeds are known to germinate along with the detection and degradation of strigolactone secreted from surrounding plants. Therefore, it was examined whether the same phenomenon occurred in the compound synthesized in the above synthesis example (test compound).
  • ⁇ Striga seeds pretreated according to a conventional method were suspended in distilled water and placed in a 96-well plate. Then, a DMSO solution of synthetic strigolactone (GR24) or test compound (YLG or YLGW) is added to the final concentration of synthetic strigolactone or test compound of 0.0001 ⁇ M, 0.001 ⁇ M, 0.01 ⁇ M, 0.1 ⁇ M, 1 ⁇ M, or After adding 10 ⁇ M and DMSO concentration to 0.1% and keeping in the dark at room temperature for 2 days, the number of radicles emerged was counted.
  • FIG. 6 shows the ratio (showing germination rate) obtained by dividing this measured value by the number of seeds when YLG is used as the test compound.
  • FIG. 7 shows bright field images and fluorescence observation images (excitation wavelength: 480 nm, detection wavelength: 520 nm) when YLG is used as the test compound and the final concentration of synthetic strigolactone or test compound is 10 ⁇ M.
  • Embodiment 5 Identification of Strigatrigolactone Receptor and Hydrolysis and Fluorescence Emission by the Receptor ⁇ 5-1. Search for Strigatrigolactone Receptor> The strigolactone receptor in Striga is unclear. Therefore, as a result of searching for the strigolactone receptor in Striga based on the amino acid sequence of the strigolactone receptor of the strigolactone-producing plant, 12 receptor candidates were found. Table 2 shows the names and amino acid sequence numbers.
  • the DNA was incorporated into an E. coli expression vector (p15TV-L for ShHTL2, 3, and 5-11, pDEST17 for ShHTL1 and 4) and introduced into E. coli (BL21-CodonPlus (DE3), Agilent).
  • E. coli was cultured, and the target protein was purified by His tag according to a conventional method. Further, the target protein was purified by gel filtration chromatography using AKTA system (Superdex 200-increase (GE Healthcare), Running buffer composition: 10 mM HEPES, 150 mM NaCl, pH 7.0).
  • the obtained strigolactone receptor candidate proteins (ShHTL1 to 11 and ShD14) were used in Example 5-3 below.
  • YLG K m values for each strigolactone receptor candidate protein are ShHTL2: 3.2 ⁇ 0.6 ⁇ M, ShHTL3: 8.3 ⁇ 2.7 ⁇ M, ShHTL4: 2.8 ⁇ 0.5 ⁇ M, ShHTL5: 1.6 ⁇ 0.2 ⁇ M, ShHTL6: 0.35 ⁇ 0.02 ⁇ M ShHTL7: 3.8 ⁇ 0.7 ⁇ M, ShHTL8: 1.9 ⁇ 1.2 ⁇ M, ShHTL9:> 10 ⁇ M, ShHTL10: 3.0 ⁇ 0.3 ⁇ M, ShHTL11: 6.1 ⁇ 0.7 ⁇ M.
  • the IC 50 values of strigolactone (5DS) for each strigolactone receptor candidate protein are as follows: ShHTL2: 8.9 ⁇ 1.5 ⁇ M, ShHTL3: 9.3 ⁇ 1.7 ⁇ M, ShHTL4: 0.30 ⁇ 0.04 ⁇ M, ShHTL5: 3.6 ⁇ 1.3 ⁇ M, ShHTL6 : 0.19 ⁇ 0.02 ⁇ M, ShHTL7: 0.12 ⁇ 0.01 ⁇ M, ShHTL8: 0.36 ⁇ 0.17 ⁇ M, ShHTL9: 1.2 ⁇ 0.2 ⁇ M, ShHTL10: 0.62 ⁇ 0.04 ⁇ M, ShHTL11: 1.6 ⁇ 0.04 ⁇ M.
  • the IC 50 values of strigolactone (4DO) for each strigolactone receptor candidate protein are as follows: ShHTL2:> 10 ⁇ M, ShHTL3: 5.1 ⁇ 1.2 ⁇ M, ShHTL4: 0.84 ⁇ 0.14 ⁇ M, ShHTL5: 5.6 ⁇ 1.5 ⁇ M, ShHTL6: 0.29 ⁇ 0.08 ⁇ M, ShHTL7: 0.11 ⁇ 0.02 ⁇ M, ShHTL8: 0.17 ⁇ 0.02 ⁇ M, ShHTL9: 1.0 ⁇ 0.2 ⁇ M, ShHTL10: 0.25 ⁇ 0.05 ⁇ M, ShHTL11: 4.3 ⁇ 0.7 ⁇ M.
  • the IC 50 values of strigolactone (ORO) for each strigolactone receptor candidate protein are as follows: ShHTL2:> 10 ⁇ M, ShHTL3:> 10 ⁇ M, ShHTL4:> 10 ⁇ M, ShHTL5:> 10 ⁇ M ⁇ M, ShHTL6: 0.058 ⁇ 0.012 ⁇ M, ShHTL7 : 1.1 ⁇ 1.4 ⁇ M ShHTL8:> 10 ⁇ M, ShHTL9: 1.6 ⁇ 0.3 ⁇ M, ShHTL10: 0.39 ⁇ 0.11 ⁇ M, ShHTL11: 4.8 ⁇ 1.1 ⁇ M.
  • the IC 50 values of strigolactone (STR) for each strigolactone receptor candidate protein are as follows: ShHTL2:> 10 ⁇ M, ShHTL3:> 10 ⁇ M, ShHTL4: 5.8 ⁇ 2.0 ⁇ M, ShHTL5:> 10 ⁇ M ⁇ M, ShHTL6: 0.36 ⁇ 0.09 ⁇ M ShHTL7: 0.12 ⁇ 0.03 ⁇ M ShHTL8: 0.77 ⁇ 0.13 ⁇ M, ShHTL9:> 10 ⁇ M, ShHTL10:> 10 ⁇ M, ShHTL11: 2.0 ⁇ 0.1 ⁇ M. From the above, it was suggested that ShHTLs 2 to 11 function as strigolactone receptors in Striga.

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  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Insects & Arthropods (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un régulateur de germination de Striga, un ingrédient actif à l'intérieur de celui-ci étant un composé ayant un squelette de base différent de celui de strigolactones et des dérivés de ceux-ci. Le régulateur de germination de Striga contient le composé représenté par la formule générale (1) ou un sel, hydrate ou solvate de celui-ci.
PCT/JP2016/069392 2015-07-01 2016-06-30 Régulateur de germination de striga Ceased WO2017002898A1 (fr)

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JP2015132413A JP2017014149A (ja) 2015-07-01 2015-07-01 ストライガ発芽調節剤
JP2015132707A JP6544768B2 (ja) 2015-07-01 2015-07-01 蛍光プローブ、及びそれを用いたストライガ発芽調節物質のスクリーニング方法
JP2015-132413 2015-07-01
JP2015-132707 2015-07-01

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2019069889A1 (fr) 2017-10-03 2019-04-11 国立大学法人名古屋大学 Modificateur de germination de plantes parasites

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WO2008007778A1 (fr) * 2006-07-13 2008-01-17 Nihon Nohyaku Co., Ltd. agent de RÉGULATION de plante parasite et son emploi
WO2008024284A2 (fr) * 2006-08-21 2008-02-28 Merck & Co., Inc. Pipérazines sulfonylées en tant que modulateurs du récepteur de cannabinoïde-1
JP2009161449A (ja) * 2007-12-28 2009-07-23 Lion Corp Ｐｐａｒ活性促進剤並びに美容用飲食品、皮膚外用剤及び医薬
WO2011125714A1 (fr) * 2010-03-31 2011-10-13 国立大学法人神戸大学 Dérivés de carbamates stimulant la germination et leur procédé de synthèse
WO2012043813A1 (fr) * 2010-09-30 2012-04-05 独立行政法人理化学研究所 Nouveau composé ayant une activité du type strigolactone et son utilisation
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

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008007778A1 (fr) * 2006-07-13 2008-01-17 Nihon Nohyaku Co., Ltd. agent de RÉGULATION de plante parasite et son emploi
WO2008024284A2 (fr) * 2006-08-21 2008-02-28 Merck & Co., Inc. Pipérazines sulfonylées en tant que modulateurs du récepteur de cannabinoïde-1
JP2009161449A (ja) * 2007-12-28 2009-07-23 Lion Corp Ｐｐａｒ活性促進剤並びに美容用飲食品、皮膚外用剤及び医薬
WO2011125714A1 (fr) * 2010-03-31 2011-10-13 国立大学法人神戸大学 Dérivés de carbamates stimulant la germination et leur procédé de synthèse
WO2012043813A1 (fr) * 2010-09-30 2012-04-05 独立行政法人理化学研究所 Nouveau composé ayant une activité du type strigolactone et son utilisation
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

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019069889A1 (fr) 2017-10-03 2019-04-11 国立大学法人名古屋大学 Modificateur de germination de plantes parasites
JPWO2019069889A1 (ja) * 2017-10-03 2020-09-10 国立大学法人東海国立大学機構 寄生植物発芽調節剤
EP3693362A4 (fr) * 2017-10-03 2021-06-09 National University Corporation Nagoya University Modificateur de germination de plantes parasites
JP7184367B2 (ja) 2017-10-03 2022-12-06 国立大学法人東海国立大学機構 寄生植物発芽調節剤

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