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WO2011086988A1 - Inhibiteur de biosynthèse de strigolactone - Google Patents

Inhibiteur de biosynthèse de strigolactone Download PDF

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Publication number
WO2011086988A1
WO2011086988A1 PCT/JP2011/050260 JP2011050260W WO2011086988A1 WO 2011086988 A1 WO2011086988 A1 WO 2011086988A1 JP 2011050260 W JP2011050260 W JP 2011050260W WO 2011086988 A1 WO2011086988 A1 WO 2011086988A1
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WIPO (PCT)
Prior art keywords
group
salt
hydrogen atom
strigolactone
general formula
Prior art date
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Ceased
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PCT/JP2011/050260
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English (en)
Japanese (ja)
Inventor
忠男 浅見
晋作 伊藤
信隆 北畑
昌樹 森
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National Institute of Agrobiological Sciences
University of Tokyo NUC
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National Institute of Agrobiological Sciences
University of Tokyo NUC
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Publication of WO2011086988A1 publication Critical patent/WO2011086988A1/fr
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    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G7/00—Botany in general
    • A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants

Definitions

  • the present invention relates to a biosynthesis inhibitor for strigolactone, which is a plant hormone that controls branching of plants.
  • Strigolactones promote seed germination of root parasitic plants Striga and Orobanche, increase parasitic weed infestation to crops, and hyphae of arbuscular mycorrhizal fungi (AM fungus) It is known as a plant physiologically active substance having an action of inducing branching and promoting absorption of phosphorus and moisture. Recently, it has been suggested that strigolactones and their metabolites are plant hormones that control the branching of plants, and have attracted attention as substances responsible for the control of normal vegetative growth and subsequent reproductive growth. Yes.
  • Strigolactone is biosynthesized by carotenoid oxidative cleavage enzymes (CCD7 and CCD8) and cytochrome P450 monooxygenase, and the F-box protein is known to be involved in its signaling (Nature, 455, pp 189-194, 2008; Nature, 455, pp.195-200, 2008; ⁇ Discovering new hormones that control the branching of plants '', August 11, 2008, RIKEN press release), branching Little is known about the mechanism that regulates. Strigolactones are known as strigol, sorgomol, 5-deoxystrigol, and orbanchol, and GR24 is known as a synthetic strigolactone. (Nature, 455, pp.195-200, 2008).
  • Substances that have biosynthesis inhibitory action on strigolactones include abamine ((N- [3-3,4-dimethoxyphenyl] -2-propenyl) -N- (4-fluorobenzyl) glycine methyl ester ) has been reported to reduce 5-deoxystrigol and solgomol secretion in sorghum and to reduce 5-deoxystrigol secretion in rice (44th Annual Meeting of the Society of Plant Chemistry Regulation, Presentation No. 62, 2009).
  • brassinosteroid biosynthetic enzyme inhibitors and abscisic acid biosynthetic enzyme inhibitors may contain compounds that have strigolactone biosynthesis inhibitory activity. It has been reported that in Japan, the chemical structure has not been revealed, and that it causes a tillering abnormality in rice and that the tillering abnormality can be recovered by co-processing with GR24. , Presentation number 2P0196B).
  • An object of the present invention is to provide a biosynthesis inhibitor for strigolactone, which is a plant hormone that controls plant branching and the like.
  • the present inventors have found that the compound represented by the following general formula (I) has an action of increasing stems (tilling action) on plants. And found that its action is strigolactone biosynthesis inhibitory action.
  • the present invention has been completed based on the above findings.
  • R 1 represents an alkyl group, an alkenyl group, or an aryl group
  • R 2 and R 3 represent a combination of a hydroxyl group and a hydrogen atom, or R 2 and R 3 together represent an oxo group.
  • N represents an integer of 2 to 8;
  • R 4 represents a hydrogen atom, or one or two halogen atoms present at any position on the benzene ring
  • a strigolactone biosynthesis inhibitor comprising a salt is provided.
  • the strigolactone biosynthesis inhibitor described above wherein R 1 is an alkyl group or a phenyl group, and n is an integer of 3 to 7; R 1 is a group having 3 to 5 carbon atoms; a branched-chain alkyl group or a phenyl radical, n is 3 or above strigolactones biosynthesis inhibitor is 4; 1 selected from the group consisting of or R 4 is a hydrogen atom, or a fluorine atom and a chlorine atom There is provided a strigolactone biosynthesis inhibitor as described above which is one or two substituents.
  • a plant branch increasing agent comprising a compound represented by the above general formula (I) or a salt thereof; a grass plant comprising a compound represented by the above general formula (I) or a salt thereof.
  • Tillering promoter flower number increasing agent comprising a compound represented by the above general formula (I) or a salt thereof; prevention of germination of parasitic weeds comprising a compound represented by the above general formula (I) or a salt thereof;
  • An agent is provided.
  • a method for inhibiting the biosynthesis of strigolactone in a plant comprising the step of applying the compound represented by the above general formula (I) or a salt thereof to the plant;
  • a method for increasing branching comprising a step of applying a compound represented by the above general formula (I) or a salt thereof to a plant; a method for promoting tillering in a grass family, A method comprising a step of applying a compound represented by the general formula (I) or a salt thereof to a grass plant; a method for increasing the number of flowers of a flowering plant by branching, wherein the general formula (I)
  • a method comprising a step of applying a compound represented by the formula or a salt thereof to a plant; a method for preventing germination of parasitic weeds, the step of applying the compound represented by the above general formula (I) or a salt thereof to a plant Is provided.
  • R 1 represents an alkyl group, an alkenyl group, or an aryl group
  • R 2 and R 3 represent a combination of a hydroxyl group and a hydrogen atom, or R 2 and R 3 Together represent an oxo group
  • n represents an integer of 2 to 8
  • R 4 represents a hydrogen atom or 1 or 2 halogen atoms present at any position on the benzene ring
  • R 1 represents an alkyl group or an alkenyl group
  • the compound represented by the general formula (I) or a salt thereof has an action of inhibiting strigolactone biosynthesis in plants, for example, increases plant branching and promotes tillering in gramineous plants. By doing so, biomass in plants, particularly rice and sugarcane, can be increased. In addition, in flowering plants, the number of flowers can be increased by increasing branching, which is also useful in the horticulture field. Furthermore, since it has a germination-preventing action against parasitic weeds, it is possible to suppress parasitic plant parasitics on crops and increase crop yield.
  • strigolactone means a plant hormone that is biosynthesized by carotenoid oxidative cleavage enzymes (CCD7 and CCD8) and cytochrome P450 monooxygenase and has an action of controlling branching of plants. The details are described in Nature, 455, pp.189-194, 2008 and Nature, 455, pp.195-200, 2008. Strigolactones that are the targets of the inhibitor of the present invention include naturally occurring strigolactones (for example, strigol, solgomol, 5-deoxystrigol, and orobancol), as well as non-natural strigolactones (for example, GR24 However, it is not limited to these.
  • the alkyl group represented by R 1 may be linear, branched, cyclic, or a combination thereof, but preferably branched alkyl can be used.
  • the number of carbon atoms of the alkyl group is, for example, about 1 to 6, preferably 3 to 6, and more preferably 4 or 5.
  • Preferred examples of the alkyl group include isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl and the like. Of these, a tert-butyl group is particularly preferred.
  • the alkenyl group represented by R 1 may be linear, branched, cyclic, or a combination thereof, but preferably branched alkenyl can be used.
  • the number of carbon atoms of the alkenyl group is, for example, about 2 to 6, preferably 3 to 6, and more preferably 4 or 5.
  • Examples of the aryl group represented by R 1 include a phenyl group and a naphthyl group, and a phenyl group can be preferably used.
  • substituents such as an alkyl group, an alkoxy group, a hydroxyl group, an amino group, and a carboxyl group may be present, It may be an unsubstituted aryl group.
  • R 1 is preferably an alkyl group or an alkenyl group, more preferably R 1 is an alkyl group, and R 1 is branched. More preferably, it is an alkyl group, and R 1 is particularly preferably a branched alkyl group having 4 or 5 carbon atoms.
  • n represents an integer of 2 to 8, preferably 3 to 7, and more preferably 3 or 4.
  • the halogen atom represented by R 4 may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, but is preferably a fluorine atom or a chlorine atom.
  • R 4 represents a halogen atom, it is preferably one or two halogen atoms selected from the group consisting of a fluorine atom and a chlorine atom.
  • the substitution position of the halogen atom is not particularly limited, and can be substituted at any position.
  • R 4 represents two halogen atoms, these halogen atoms may be the same or different.
  • the compound represented by the above formula (I) has at least one asymmetric carbon, and may further have one or more asymmetric carbons depending on the type of the substituent.
  • any mixture of isomers for example, a mixture of two or more diastereoisomers or a racemate is used as the inhibitor of the present invention. You may use as an active ingredient.
  • the compound represented by the above formula (I) can form an acid addition salt, and may form an acid addition salt depending on the type of the substituent.
  • the type of salt is not particularly limited, and salts with mineral acids such as hydrochloric acid and sulfuric acid, salts with organic acids such as p-toluenesulfonic acid, methanesulfonic acid and tartaric acid, metals such as sodium salt, potassium salt and calcium salt Examples thereof include salts with organic amines such as salts, ammonium salts and triethylamine, and salts with amino acids such as glycine.
  • the compound represented by the above formula (I) or a salt thereof may exist as a hydrate or a solvate, these substances may be used as an active ingredient of the inhibitor of the present invention.
  • a preferable compound as an active ingredient of the inhibitor of the present invention for example, 2,2-dimethyl-7-phenoxy-4- (1H-1,2,4-triazol-1-yl) heptan-3-ol (MA40); 2,2-dimethyl-7-phenoxy-4- (1H-1,2,4-triazol-1-yl) heptan-3-one (MA39); 5-phenoxy-1-phenyl-2- (1H-1,2,4-triazol-1-yl) pentan-1-ol (MA32); 7- (4-Fluorophenoxy) -2,2-dimethyl-4- (1H-1,2,4-triazol-1-yl) heptan-3-one (SI-13); 2,2-dimethyl-8-phenoxy-4- (1H-1,2,4-triazol-1-yl) octan-3-one (SI-14); 7- (4-Fluorophenoxy) -2,2-dimethyl-4- (1H-1,2,4-triazol-1-yl)
  • MA-32, MA-39, MA-40, SI-15, SI-18, SI-21, SI-22, SI23, and SI-24 are more preferable, and particularly preferable is MA-39, SI-18, SI-21, SI-23, and SI-24.
  • SI29 or TIS109 is also preferable.
  • the compound represented by the general formula (I) or a salt thereof has an action of inhibiting the biosynthesis of strigolactone in the plant, and can be applied to a plant for the purpose of increasing the branching of the plant, for example.
  • the compound represented by the general formula (I) or a salt thereof can promote tillering in gramineous plants.
  • the term “tiller” means that a side branch develops and grows from a joint of a stem close to the root in a gramineous crop, but this term is interpreted in a limited way in any sense. It must be interpreted in the broadest sense. Therefore, by applying the inhibitor of the present invention to rice or sugarcane, an increase in biomass due to branching can be achieved.
  • the compound represented by the general formula (I) or a salt thereof can increase the number of flowers by increasing branching in flowering plants, and therefore can be applied as a flower number increasing agent for agriculture and horticulture. It is.
  • the flowering plant to be applied is not particularly limited, and can be applied to any flowering plant such as crops such as rice and fruit trees, and garden plants such as tulips and roses.
  • strigolactones promote the seed germination of root parasitic plants, Striga and Orobanche, to increase parasitic weed parasitism on crops, but using compounds represented by the general formula (I) or salts thereof
  • strigolactone By inhibiting the biosynthesis of strigolactone, it is possible to prevent the emergence of parasitic weeds, preferably parasitic weeds such as Striga and Orobanche, and to increase the crop yield by suppressing the parasitic plant infestation.
  • the inhibitor of the present invention can be prepared as an agrochemical composition using, for example, pharmaceutical additives known in the art.
  • the form of the composition for agricultural chemicals is not particularly limited, and any form may be adopted as long as it is a form that can be used in the art.
  • a composition in the form of an emulsion, solution, oil, water solvent, wettable powder, flowable, powder, fine granule, granule, aerosol, fumigant, or paste can be used.
  • a method for producing the composition for agricultural chemicals is not particularly limited, and any method available to those skilled in the art can be appropriately employed.
  • As the active ingredient of the inhibitor of the present invention two or more compounds represented by the above formula (I) or salts thereof may be used in combination.
  • the active ingredient of other agricultural chemicals such as an insecticide, a fungicide, an insecticide fungicide, and a herbicide
  • blend the active ingredient of other agricultural chemicals such as an insecticide, a fungicide, an insecticide fungicide, and a herbicide
  • the application method and application amount of the inhibitor of the present invention can be appropriately selected by those skilled in the art according to the conditions such as the purpose of application, dosage form, and application location. For example, for rice and the like, about 0.1 ⁇ M to 50 ⁇ M, preferably about 0.5 to 20 ⁇ M can be selected, but the application amount is not limited to the above specific range.
  • Example 1 Preparation of 6-phenoxy-1-phenyl-2- (1H-1,2,4-triazol-1-yl) hexan-1-one Acetophenone (6.5 g) was dissolved in diethyl ether (10 mL). Aluminum chloride (catalytic amount) was added. Bromine (5.0 g) was gradually added under ice-cooling while stirring, and the mixture was stirred at room temperature for 30 minutes after the addition. Water was added to stop the reaction, and the mixture was extracted 3 times with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude 2-bromo-1-phenylethanone mixture (9.5 g).
  • Example 2 Strigolactone inhibitory action (A) Method (i) Rice growth method Sterile solution I (2.5% sodium hypochlorite, 0.01% Tween-20) was added to rice seeds (Shiokari) and shaken at room temperature for 15 minutes. The sterilized solution I was discarded, sterilized solution II (2.5% sodium hypochlorite) was added, and the mixture was shaken at room temperature for 15 minutes. The sterilizing solution II was discarded in the clean bench, the seeds were washed 5 times with sterilized water, and allowed to stand at 25 ° C in the dark for 2 days. Two days later, the germinating seeds were transplanted to a rice hydroponic agar medium and allowed to stand for 6 days at 25 ° C.
  • Table 2 shows the strigolactone endogenous growth inhibitory effect when the test compound is treated in rice.
  • the percentage of strigolactone inhibition in the hydroponic solution compared to the untreated plot is shown as a percentage,-is untested.
  • Table 3 shows the strigolactone inhibition rate (%) in the roots when compared with the untreated group.
  • Fig. 1 shows the effect of soil-cultivated rice after 5 weeks of treatment with MA39.
  • Rice cultivated in a pot was soaked in water supplemented with MA39, and the water supplemented with MA39 was exchanged twice a week. You can see how MA39 promotes tillering and branching increases.
  • Fig. 2 shows the increase in the number of tillers over time
  • Fig. 3 shows the biomass after 5 weeks of treatment with MA39
  • Fig. 4 shows the leaf width of the youngest developed leaf.
  • FIG. 5 shows the results of treatment with SI-24 (40 days after water absorption)
  • FIG. 6 shows the results of morphological changes over time at multiple concentrations of SI-24. From these results, it was shown that the strigolactone biosynthesis inhibitor of the present invention has an action of promoting branching on plants, and as a result, increases biomass. It was also shown that the leaf blade width increased at least in MA39.
  • Example 3 Strigolactone inhibitory action
  • TIS109 and TIS110 the inhibitory effect of TIS109 and TIS110 on the endogenous amount of strigolactone during compound treatment in rice was measured. The results are shown in Table 4 below. The amount of strigolactone in the hydroponic liquid when compared with the untreated plot was shown as a relative ratio (%).
  • Example 4 Effect on Arabidopsis thaliana Arabidopsis seeds were surface sterilized with 70% ethanol and sown in 1/2 ⁇ MS medium. After low temperature treatment at 4 ° C for 2 days, it was grown at 23 ° C for 2 weeks. Then, it moved to hydroponics, and the compound-containing hydroponic solution was changed once every 4 days. As is clear from the results shown in FIGS. 7 and 8, an increase in branching was observed in the SI-29 treated group compared to the control group.

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  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Ecology (AREA)
  • Forests & Forestry (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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Abstract

La présente invention concerne le composé représenté par la formule (I), qui est un inhibiteur de biosynthèse pour la strigolactone, une hormone végétale qui contrôle la ramification des plantes, etc. (R1 représente un groupe alkyle, un groupe alcényle, ou un groupe aryle ; R2 et R3 une combinaison d'un groupe hydroxyle et d'atomes d'hydrogène, ou, R2 et R3 forment conjointement un groupe oxo ; n représente un entier compris entre 2 et 6 ; et R4 représente un atome d'hydrogène ou un atome d'halogène).
PCT/JP2011/050260 2010-01-12 2011-01-11 Inhibiteur de biosynthèse de strigolactone Ceased WO2011086988A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104396647A (zh) * 2014-10-31 2015-03-11 湖南农丰种业有限公司 水稻光温敏不育系核心种子生产方法
CN107041358A (zh) * 2017-04-17 2017-08-15 石河子大学 防治寄生性植物列当的方法及其专用制剂和该制剂的用途
CN110663385A (zh) * 2019-10-23 2020-01-10 青岛农业大学 一种新型复合物在提高平邑甜茶抵抗钾离子胁迫中的新应用
JP2020083853A (ja) * 2018-11-30 2020-06-04 学校法人東京農業大学 ストリゴラクトン生合成阻害剤
CN116589419A (zh) * 2023-03-31 2023-08-15 中国农业大学 2-苯氧基-2-（1h-1,2,4-三唑）-苯乙酮类化合物及其制备方法与应用

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JPS63190802A (ja) * 1986-12-18 1988-08-08 インペリアル・ケミカル・インダストリーズ・ピーエルシー 植物の生長調整用成形体
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JPS6011476A (ja) * 1983-06-10 1985-01-21 バスフ　アクチェンゲゼルシャフト トリアゾリルアルコール異性体混合物の製造方法
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104396647A (zh) * 2014-10-31 2015-03-11 湖南农丰种业有限公司 水稻光温敏不育系核心种子生产方法
CN107041358A (zh) * 2017-04-17 2017-08-15 石河子大学 防治寄生性植物列当的方法及其专用制剂和该制剂的用途
JP2020083853A (ja) * 2018-11-30 2020-06-04 学校法人東京農業大学 ストリゴラクトン生合成阻害剤
JP7315912B2 (ja) 2018-11-30 2023-07-27 学校法人東京農業大学 ストリゴラクトン生合成阻害剤
CN110663385A (zh) * 2019-10-23 2020-01-10 青岛农业大学 一种新型复合物在提高平邑甜茶抵抗钾离子胁迫中的新应用
CN116589419A (zh) * 2023-03-31 2023-08-15 中国农业大学 2-苯氧基-2-（1h-1,2,4-三唑）-苯乙酮类化合物及其制备方法与应用

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