AU2011246088A1

AU2011246088A1 - Cell differentiation promoter and use of same

Info

Publication number: AU2011246088A1
Application number: AU2011246088A
Authority: AU
Inventors: Tadao Asami; Akiyoshi Kawaoka; Kazuya Nanto; Naoki Negishi; Masatoshi Oishi
Original assignee: Nippon Paper Industries Co Ltd; Jujo Paper Co Ltd; University of Tokyo NUC
Current assignee: Nippon Paper Industries Co Ltd; University of Tokyo NUC
Priority date: 2010-04-27
Filing date: 2011-04-27
Publication date: 2012-11-08
Anticipated expiration: 2031-04-27
Also published as: AU2011246088A2; JP5529224B2; WO2011136285A1; JPWO2011136285A1; JP2013039129A; JP2013047225A; AU2011246088B2; JP5529223B2; JP5165154B2; CL2012002971A1

Abstract

Disclosed are compounds which are useful as the active ingredient of a cell differentiation promoter. As an example of said compounds, a compound, which is useful as the active ingredient of an adventitious root formation promoter capable of promoting rooting of a plant and improving the rooting rate thereof, can be cited. Also disclosed are a rooting method and a rooting medium, wherein an adventitious root formation promoter containing the aforesaid compound is used, for improving the productivity of clone seedlings by a cuttage method, a tissue culture method or the like. Specifically disclosed are a cell differentiation promoter which contains a compound represented by any of general formulae (1-1), (1-2), (1-3), (2-1) and (2-2) or a salt of the same, a plant shoot rooting medium which contains said cell differentiation promoter, and a method for producing clone seedlings which comprises using said cell differentiation promoter or said rooting medium.

Description

Docket No. PNPA-12278-PCT DESCRIPTION CELL DIFFERENTIATION ACCELERATOR AND USE THEREOF 5 TECHNICAL FIELD [0001] The present invention relates to a cell differentiation accelerator and use thereof. BACKGROUND ART 10 [0002] Cuttage methods in which roots are taken by placing a scion in a place where a plant's bud is grafted to a grafting bed or a medium and tissue culture methods in which an adventitious bud is collected by culturing a plant tissue and the root is taken therefrom have been utilized 15 as procedures for mass production of a homogenous plant body (clone seedling) having a trait suitable for a purpose in fields of agricultural production, forestation, breeding, and others. An ability of the plant tissue to take root in these methods has a great effect on productivity of the 20 clone seedling. Thus, it is important to enhance the ability to take root. [0003] JP 2001-231355-A (Patent Document 1) describes that the ability to take root is promoted when a mother tree for taking scions selected from plants belonging to 25 genera Eucalyptus and Acacia is treated with paclobutrazol before being removed as a scion. [0004] Meanwhile, JP 2002-47108-A (Patent Document 2) describes that a triazole compound having a particular structure has an inhibitory effect on metabolism of 30 brassinosteroid in plants and is useful for regulating growth and development of the plants. JP 2003-113008-A (Patent Document 3) describes that the growth of the plant is facilitated when the triazole compound described in Docket No. PNPA-12278-PCT 2 above Patent Document 2 together with a plant growth hormone such as benzyladenine is applied to the plant. RELATED ART DOCUMENTS 5 PATENT LITERATURE [0005] Patent Document 1: JP 2001-231355-A Patent Document 2: JP 2002-47108-A Patent Document 3: JP 2003-113008-A 10 DISCLOSURE OF INVENTION TECHNICAL PROBLEM (0006] However in the method described in Patent Document 1, it was difficult to obtain the scion unless several months had passed after the mother tree for taking 15 scions was previously treated with paclobutrazol. Thus, those having an immediate effect on the enhancement of the ability to take root have been required. [0007] Meanwhile, the methods in Patent Documents 2 and 3 are the methods of controlling brassinosteroid for the 20 growth of the plant. Therefore, these are different from the technology such as the cuttage method of facilitating the rooting of the scion, i.e., the technology of facilitating differentiation of a root tissue alone. Generally, a condition for facilitating the rooting of the 25 scion is different from a condition for facilitating the growth of the plant. The rooting of the scion is also often facilitated by a condition for stopping the growth of the plant. [0008] The ability to take root was insufficient for the 30 plant in the method described in Patent Document 1. Among them, it could not be anticipated to improve the ability to take root when this method was applied to plants, such as plants belonging to genus Eucalyptus, whose ability to take Docket No. PNPA-12278-PCT 3 root was originally low. [0009] It is an object of the present invention to provide a compound useful as an active ingredient of a cell differentiation accelerator. Examples of the compound may 5 include compounds capable of becoming the active ingredient of an adventitious root rooting accelerator that facilitates the rooting from the plant and enhances its rooting rate. It is another object of the present invention to provide a rooting method and a medium for 10 rooting for enhancing productivity of a clone seedling by a method such as a cuttage method and a tissue culture method, among them, for enhancing the productivity of a clone seedling belonging to plant species whose ability to take root is low, by utilizing the cell differentiation 15 accelerator containing the compound. It is still another object to provide a novel compound. MEANS FOR SOLVING PROBLEM [0010] The present invention provides following [1] to 20 [21]: [1] A cell differentiation accelerator comprising a compound represented by any of the general formulae (1-1), (1-2), (1-3), (2-1), and (2-2) or a salt thereof: R111 R112 NQ r N 25 wherein Ri represents a hydrogen atom, a hydroxyl group or an Docket No. PNPA-12278-PCT 4 alkyl group, R12 represents an alkyl group or an aromatic hydrocarbon group which may have a substituent,

R

113 represents an aromatic hydrocarbon group which may 5 have a substituent, and a wavy line represents a cis configuration or a trans configuration; R1 24

R

1 21 R1 23 N 0~~ -- . (1-2) R2 N ' N wherein 10 R represents a hydrogen atom, an alkyl group, or an alkoxyalkyl group, R12 represents an aromatic hydrocarbon group which may have a substituent, and

R

123 and R each independently represent a hydrogen 15 atom or an alkyl group;

R

13 1 OH R1 32 N R1(33 NQN wherein

R

131 represents a hydrogen atom, an alkyl group, or an alkenyl group; 20 R132 represents an alkyl group, or an aromatic hydrocarbon group which may have a substituent, and R 133represents an aromatic hydrocarbon group which may Docket No. PNPA-12278-PCT 5 have a substituent; 0 R211 -( 0 H C H2 ) N .. (2-1) 1 N Az~ wherein R represents an aromatic hydrocarbon group which may 5 have a substituent or a heterocyclic group which may have a substituent, m is 1 or 2, n is 0 or 1, and A represents a nitrogen atom or -CH-; and 0 R221 ... (2-2) P 10 wherein R represents a hydrogen atom, an alkyl group, or a halogenated alkyl group, R22 represents a hydrogen atom, an alkyl group, or a 15 halogen atom, and p is an integer of 1 to 5. [2] The cell differentiation accelerator according to [1] above, wherein:

R

1 il represents a hydroxyl group; 20 R12 represents a 4-chlorophenyl group or a t-butyl group; and

R

1 1 3 represents a 4-methylphenyl group or a 4 dimethylaminophenyl group. [3] The cell differentiation accelerator according to 25 [1] above, wherein: R represents an ethyl group, a methyl group, a n- Docket No. PNPA-12278-PCT 6 propyl group or a methoxymethyl group; R12 represents a 4-chlorophenyl group, a 4 methylphenyl group, a 4-n-butoxyphenyl group or a 2,4 dichlorophenyl group; and 5 both R 12 and R1 24 represent a hydrogen atom. [4] The cell differentiation accelerator according to [1] above, wherein: R represents a hydrogen atom, a methyl group or a 3 propenyl group; 10 R12 represents a 4-chlorophenyl group or a phenyl group; and R represents a 4-chlorophenyl group. [5] The cell differentiation accelerator according to [1] above, wherein: 15 R2i represents a naphthyl group; m is 2; and n is 0. [61 The cell differentiation accelerator according to [1] above, wherein: 20 R 211 represents a 4-phenoxyphenyl group; m is 1; n is 1; and A represents a nitrogen atom. [7] The cell differentiation accelerator according to 25 [11 above, wherein: R represents a 3-indole group; m is 1; n is 0; and A represents a nitrogen atom. 30 [8] The cell differentiation accelerator according to [1] above, wherein: R represents a methyl bromide group; R22 represents a fluorine atom; and Docket No. PNPA-12278-PCT 7 p is 2. [9] The cell differentiation accelerator according to any one of (1] to [8] above, wherein the cell is a plant cell. 5 [10] The cell differentiation accelerator according to any one of [1] to [9] above, which is an adventitious root formation accelerator for a plant. [11] A medium for rooting for a shoot of a plant, containing the cell differentiation accelerator according 10 to any one of [1] to [10] above. [12] A method of producing a clone seedling, wherein a shoot of a plant is cultivated in the presence of the cell differentiation accelerator according to any one of [1] to [10] above and a root is taken from the shoot. 15 [13] A method of producing a clone seedling, wherein a shoot of a plant is cultivated in the medium for rooting according to [11] above and a root is taken from the shoot. [14] A method of facilitating cell differentiation using a compound represented by any of the general formulae 20 (1-1), (1-2), (1-3), (2-1), and (2-2) above or a salt thereof. [15] The method of facilitating the cell differentiation according to [14] above, wherein the cell is a plant cell. 25 [16] The method of facilitating the cell differentiation according to [14] or [15] above, wherein the cell differentiation is facilitation of adventitious root formation in a plant. [17] A novel compound represented by the following 30 general formula (2-1) or (2-2) above, or a salt thereof. [18] The compound according to [17] above, wherein:

R

211 represents a naphthyl group; m is 2; and Docket No. PNPA-12278-PCT 8 n is 0. [19] The compound according to [17] above, wherein: R represents a 4-phenoxyphenyl group; m is 1; 5 n is 1; and A represents a nitrogen atom. [20] The compound according to [17] above, wherein: R represents a 3-indole group; m is 1; 10 n is 0; and A represents a nitrogen atom. [21] The compound according to (17] above, wherein: R221 represents a methyl bromide group; R22 represents a fluorine atom; and 15 p is 2. [0011] Aspects of the present invention may include the following [1-1] to [1-8]. [1-1] An adventitious root formation accelerator for plants comprising a compound represented by any of the 20 above formulae (1-1), (1-2), and (1-3) or a salt thereof. [1-2] The adventitious root formation accelerator according to [1-1] above, wherein R 111 represents a hydroxyl group, Ru2 represents a 4-chlorophenyl group or a t-butyl group, and R 113 represents a 4-methylphenyl group or a 4 25 dimethylaminophenyl group. (1-3] The adventitious root formation accelerator according to [1-1] above, wherein R represents an ethyl group, a methyl group, a n-propyl group or a methoxymethyl group, R12 represents a 4-chlorophenyl group, a 4 30 methylphenyl group, a n-butoxyphenyl group or a 2,4 dichlorophenyl group, and both R1 23 and R1 24 represent a hydrogen atom. [1-4) The adventitious root formation accelerator Docket No. PNPA-12278-PCT 9 according to [1-1] above, wherein R 131 represents a hydrogen atom, a methyl group or a 3-propenyl group, R1 32 represents a 4-chlorophenyl group or a phenyl group, and R 133 represents a 4-chlorophenyl group. 5 [1-5] An auxin activity accelerator comprising a compound represented by any of the above formulae (1-1), (1-2), and (1-3) or a salt thereof. [1-6] A medium for rooting in a shoot of a plant containing the adventitious root formation accelerator 10 according to any one of [1-1] to [1-4] above or the auxin activity accelerator according to [1-5] above. [1-7] A method of producing a clone seedling, wherein a shoot of a plant is cultured in the presence of the adventitious root formation accelerator according to any 15 one of [1-1] to [1-4] above or the auxin activity accelerator according to [1-5] above and a root is taken from the shoot. [1-8] A method of producing a clone seedling, wherein a shoot of a plant is cultured in the medium for rooting 20 according to [1-6] above and a root is taken from the shoot. [0012] Other aspects of the present invention may include following [2-1] to [2-13]. [2-1] A novel compound represented by the above formula (2-1) or (2-2) or a salt thereof. 25 [2-2] The compound according to [2-1] above, wherein R represents a naphthyl group, m is 2 and n is 0, respectively, and A represents a nitrogen atom. [2-3] The compound according to [2-1] above, wherein R represents a 4-phenoxyphenyl group, m is 1 and n is 1, 30 respectively, and A represents a nitrogen atom. [2-4] The compound according to [1] above, wherein R 211 represents a 3-indole group, m is 1 and n is 0, respectively.

Docket No. PNPA-12278-PCT 10 [2-5] The compound according to [2-1] above, wherein R represents a methyl bromide group, R22 represents a fluorine atom, and the p is 2. [2-6] A cell differentiation accelerator containing 5 the compound according to any one of [2-1] to [2-5] above. [2-7] The cell differentiation accelerator according to (2-6] above, wherein the cell is a plant cell. [2-8] An adventitious root formation accelerator for plants containing the compound according to any one of [2 10 1] to [2-5] above. [2-9] A plant hormone activity accelerator containing the compound according to any one of [2-1] to [2-5] above. [2-10] The plant hormone activity accelerator according to [2-9] above, wherein the plant hormone is 15 auxin. [2-11] A medium for rooting in a shoot of a plant containing the adventitious root formation accelerator according to [2-8] above or the plant hormone activity accelerator according to [2-9] or [2-10) above. 20 [2-12] A method of producing a clone seedling, wherein a shoot of a plant is cultured in the presence of the adventitious root formation accelerator according to [2-8] above or the plant hormone activity accelerator according to [2-9] or [2-10] above and a root is taken from the shoot. 25 [2-13] A method of producing a clone seedling, wherein a shoot of a plant is cultured in the medium for rooting according to [2-11] above and a root is taken from the shoot. 30 EFFECT OF THE INVENTION [0013] According to the present invention, the differentiation of the cell can be facilitated. The formation of the adventitious root from the plant can be Docket No. PNPA-12278-PCT 11 facilitated and a rooting rate can be enhanced. The formation of the adventitious root is facilitated by, for example, facilitating the activity of the plant hormone such as auxins (hereinafter sometimes referred to as the 5 "auxin" simply). Therefore, according to the present invention, the productivity of the clone seedling can be enhanced. According to the present invention, it is possible to remarkably enhance the productivity of the clone seedling of the plant species whose ability to take 10 root is low. Therefore, the present invention contributes to mass and rapid production of the clone seedling of widely various plant species, among them, enables to massively and rapidly produce the clone seedling even if the plant species has the low ability to take root, and 15 opens the way to its industrial application. BRIEF DESCRIPTION OF DRAWINGS [0014] FIG. 1 is a graph showing a rooting rate of each compound in EXAMPLES 1 to 12 and COMPARATIVE EXAMPLES 2 to 20 5 in Eucalyptus plant; FIG. 2-1 is a view showing an appearance of rooting in a Eucalyptus plant cultivated in a compound free condition in COMPARATIVE EXAMPLE 1; FIG. 2-2 is a view showing an appearance of rooting in a 25 Eucalyptus plant cultivated in the presence of a compound MA65 in EXAMPLE 11; FIG. 3 is a graph showing a rooting rate of MA65 in EXAMPLES 13 in Silver Dollar Gum (Eucalyptus cineria, Argyle Apple, Mealy Stringybark); 30 FIG. 4-1 is a view showing a GUS activity in Arabidopsis thaliana cultivated in the presence of the compound MA65 in EXAMPLE 14; FIG. 4-2 is a view showing a GUS activity in Arabidopsis Docket No. PNPA-12278-PCT 12 thaliana cultivated in the presence of the compound MA65 in EXAMPLE 14; FIG. 4-3 is a view showing a GUS activity in Arabidopsis thaliana cultivated in the compound free condition in 5 COMPARATIVE EXAMPLE 7; FIG. 4-4 is a view showing a GUS activity in Arabidopsis thaliana cultivated in the compound free condition in COMPARATIVE EXAMPLE 7; FIG. 5 is a graph showing a rooting rate of each compound 10 in EXAMPLES 15 to 19 and COMPARATIVE EXAMPLES 8 to 12 in a Eucalyptus plant; and FIG. 6 is a graph showing a rooting rate of KSR221 in Example 20 and COMPARATIVE EXAMPLE 13 in Silver Dollar Gum (Eucalyptus cineria, Argyle Apple, Mealy Stringybark) 15 EMBODIMENTS FOR CARRYING OUT THE INVENTION [0015] The cell differentiation accelerator of the present invention comprises the compound represented by any of the general formulae (1-1), (1-2), (1-3), (2-1), and (2 20 2), or the salt thereof. The adventitious root formation accelerator of the present invention comprises the compound represented by any of the general formulae (1-1), (1-2), (1-3), (2-1), and (2-2), or the salt thereof. Definitions of substituents that may be included in the compound 25 represented by any of the general formulae (1-1), (1-2), (1-3), (2-1), and (2-2) are described first. (0016] In the present invention, examples of the alkyl group may include an alkyl group having one or more and about 6 or less carbon atoms. The alkyl group may be 30 straight or branched. Examples of the alkyl group may include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, and tert-butyl group, and of these, preferable are Docket No. PNPA-12278-PCT 13 methyl group, ethyl group, n-propyl group, and tert-butyl group. [0017] In the present invention, examples of the alkoxyalkyl group may include an alkoxyalkyl group having 5 one or more and about 15 or less carbon atoms. An alkyl chain moiety in the alkoxyalkyl group may be either straight or branched, and a straight chain is preferable. An alkoxy moiety in the alkoxyalkyl group may also be either straight or branched, and a straight chain is 10 preferable. Examples of the alkoxyalkyl group may include methoxymethyl group and methoxyethyl group, and methoxymethyl group is preferable. [0018] In the present invention, examples of the alkenyl group may include an alkenyl group having two or more and 15 about 6 or less carbon atoms. The alkenyl group may be either straight or branched, and a straight chain is preferable. Examples of the alkenyl group may include vinyl group, allyl group, 1-propenyl group, 2-propenyl group, and 2-butenyl group, and 2-propenyl group is 20 preferable. [0019] In the present invention, the alkoxy group may include an alkoxy group having one or more and about 6 or less carbon atoms. The alkoxy group may be either straight or branched, and a straight chain is preferable. Examples 25 of the alkoxy group may include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, and n-butoxy group, and n-butoxy group (1 butoxy group) is preferable. In the present invention, examples of the dialkylamino 30 group may include a dialkylamino group having one or more and about 6 or less carbon atoms. An alkyl chain moiety in the dialkylamino group may be either straight or branched, and a straight chain is preferable. Examples of the Docket No. PNPA-12278-PCT 14 dialkylamino group may include dimethylamino group and diethylamino group, and of these, dimethylamino group is preferable. [0020] In the present invention, examples of the halogen 5 atom may include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Of these, the fluorine atom and the chlorine atom are preferable. [0021] In the present invention, examples of the halogenated alkyl group may include a halogenated alkyl 10 group having one or more and about 6 or less carbon atoms. An alkyl chain moiety in the halogenated alkyl group may be either straight or branched, and a straight chain is preferable. One halogen atom or two or more halogen atoms may be contained in the halogenated alkyl group, and one 15 halogen atom is preferably contained. Examples of the halogenated alkyl group may include halogenated alkyl groups such as an alkyl fluoride group, an alkyl chloride group, an alkyl bromide group, and an alkyl iodide group having the alkyl group listed as the examples of the above 20 alkyl group, and a methyl bromide group is preferable. [0022] In the present invention, an aromatic hydrocarbon group which may have a substituent means the aromatic hydrocarbon group having a substituent (s) and the aromatic hydrocarbon group having no substituent. The aromatic 25 hydrocarbon group means a monovalent substituent of aromatic hydrocarbon. The number of carbon atoms in the aromatic hydrocarbon group is not particularly limited, and is preferably 3 or more and 15 or less and more preferably 6 or more and 10 or less. The aromatic hydrocarbon group 30 may be a group to which one or more aromatic rings such as an aromatic ring having 4 or more and 7 or less carbon atoms are bound (including condensation). Examples of the aromatic hydrocarbon group may include pentanyl group, Docket No. PNPA-12278-PCT 15 phenyl group, heptyl group, naphthyl group, anthracyl group, and phenanthryl group, and of these, preferable are phenyl group and naphthyl group. [0023] A heterocyclic group which may have a substituent 5 means the heterocyclic group having a substituent(s) and the heterocyclic group having no substituent. The heterocyclic group means a cyclic group containing a heteroatom such as an oxygen atom, a nitrogen atom or a sulfur atom. In the case of the heterocyclic group in 10 which two or more rings are bound (including the condensation), the heteroatom may be contained in any one of the rings. The heterocyclic group containing the nitrogen atom is preferable as the heterocyclic group. The number of the carbon atoms contained in the heterocyclic 15 group is not particularly limited, and is preferably 3 or more and 15 or less and more preferably 6 or more and 10 or less. Examples of the heterocyclic group may include 5 membered cyclic groups such as pyrrolyl group, imidazole group, pyrazolyl group, furyl group, oxazolyl group, 20 thiophenyl group, thiazolyl group, and isothiazolyl group; 6-membered cyclic groups such as pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, piperidil group, piperadyl group, morpholyl group, 2H-pyral group, and 4H pyral group; and heteroatom-containing condensed cyclic 25 groups such as pyrrolidyl group, pyrindyl group, phthalimide group, and indole group. Of these, the heteroatom-containing condensed cyclic group is preferable, and the indole group is preferable. [0024] Examples of the substituent capable of being 30 contained in the aromatic hydrocarbon group and the heterocyclic group may include halogen atoms, alkyl group, cycloalkyl group, halogenated alkyl group, alkoxy group, cycloalkyl group such as cyclopropyl group, amino group, Docket No. PNPA-12278-PCT 16 mono- or di-alkylamino group, carboxyl group, alkoxycarbonyl group such as ethoxycarbonyl group, alkanoyl group such as acetyl group, aroyl group such as benzoyl groups, aralkyl group such as benzyl group, aryl group such 5 as phenyl group, aryloxy group such as phenoxy group, heteroaryl group such as pyridyl group, heteroaryloxy group such as pyridyloxy group, heterocyclic group such as pyrrolidinyl group, hydroxyl group, nitro group, and cyano group. Of these, preferable are the alkyl group, the 10 halogen atom, and the alkoxy group. [0025] The number of the substituents may be 0 or more and 5 or less, and is typically 0 or more and 3 or less and preferably 0 or more and 2 or less in the aromatic hydrocarbon group and the heterocyclic group which may have 15 the substituent. When the group has two or more substituents, the substituents may be the same or different. [0026] A portion in a skeleton of each general formula, at which the aromatic hydrocarbon group or the heterocyclic group which may have the substituent is bound is not 20 particularly limited. [0027] A position to be substituted on the aromatic hydrocarbon group and the heterocyclic group having the substituent is not particularly limited. For example, the position to be substituted on the phenyl group is 25 preferably position 2 and/or position 4. [0028] Examples of the aromatic hydrocarbon group which may have the substituent may include 2-chlorophenyl group, 4-chlorophenyl group, 3,4-dichlorophenyl group, 2,4 dichlorophenyl group, 3,4-difluorophenyl group, 2,4 30 difluorophenyl group, 4-bromophenyl group, 4 trifluoromethoxyphenyl group, 4-toluyl group, 4 trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-hydroxyphenyl group, 4-methoxyphenyl group, 2-chloro-4- Docket No. PNPA-12278-PCT 17 trifluoromethylphenyl group, 3-chloro-4 trifluoromethylphenyl group, 4-bromo-2-chlorophenyl group, biphenyl-4-yl group, (4-chlorophenyl)oxy-2-chlorophenyl group, 4-(1-butoxy)phenyl group, 4-phenoxyphenyl group, and 5 1-naphthyl group. Of these, more preferable are 4 chlorophenyl group, 2,4-dichlorophenyl group, 4-(1 butoxy)phenyl group, 4-dimethylaminophenyl group, 4 methylphenyl group, 2,4-difluorophenyl group, 4 phenoxyphenyl group, and 1-naphthyl group. 10 [0029] In the present invention, the 4-chlorophenyl group means a group represented by the following formula (a). CI [0030] In the present invention, the 2,4-dichlorophenyl 15 group means a group represented by the following formula (b). .. (b) CI Cl (00311 In the present invention, the 4-(1-butoxy)phenyl group means a group represented by the following formula 20 (c). I .--- (c) H3C 0 [0032) In the present invention, the 2,4-difluorophenyl group means a group represented by the following formula (d).

Docket No. PNPA-12278-PCT 18 F (d) F [0033] In the present invention, the 4-phenoxyphenyl group means a group represented by the following formula (e). IK ~(e) 5 [0034] In the present invention, the 4-dimethylamino group means a group represented by the following formula (f). 0 ... Wf N-CH

H

3 0 10 [0035] In the present invention, the 1-naphthyl group means a group represented by the following formula (g). CIN N

.

9 [0036] An example of the heterocyclic group which may have the substituent is preferably a 3-indole group 15 represented by the following (h).

Docket No. PNPA-12278-PCT 19 \ """(h) ,' N H [0037] In the present invention, the 4-methylphenyl group means a group represented by the following formula (i). ,/ \... 5

CH

3 [0038] In the above general formula (1-1), Rill represents a hydrogen atom, a hydroxyl group or an alkyl group, R1 2 represents an alkyl group or an aromatic hydrocarbon group which may have a substituent, and Rm 3 10 represents an aromatic hydrocarbon group which may have a substituent. [0039] In the general formula (1-1), Rill represents a hydrogen atom, a hydroxyl group or an alkyl group, and preferably represents the hydroxyl group. 15 [0040] In the general formula (1-1), R112 represents an alkyl group or an aromatic hydrocarbon group which may have a substituent, preferably represents the alkyl group or the aromatic hydrocarbon group having the substituent, and more preferably represents the alkyl group, or phenyl group 20 having the substituent. [0041] The alkyl group represented by R is preferably an alkyl group having one or more and 4 or less carbon atoms, and preferably an alkyl group having a branched chain. 25 [0042] Examples of the substituent which the aromatic Docket No. PNPA-12278-PCT 20 hydrocarbon group represented by R12 may have may include halogen atoms, and a chlorine atom is preferable. A position to be substituted on the aromatic hydrocarbon group represented by Rii2 is preferably position 4. The 5 number of the substituent in the aromatic hydrocarbon group 112 represented by Rn , which may have the substituent is not particularly limited, and is preferably one. [0043] Preferable examples of R 1 may include t-butyl group and 4-chlorophenyl group. 10 [0044] In the general formula (1-1), Ru3 represents an aromatic hydrocarbon group which may have a substituent, preferably represents the aromatic hydrocarbon group having the substituent, and phenyl group having the substituent is preferable. Alkyl groups and dialkylamino groups are 15 preferable as the substituent which the aromatic hydrocarbon group represented by R 113 may have. The alkyl group and the dialkylamino group preferably have one or more and 3 or less carbon atoms and preferably have a straight structure. Preferable examples of the substituent 20 which the aromatic hydrocarbon group represented by R 113 may have may include methyl group and dialkylamino group. A position to be substituted on the aromatic hydrocarbon group represented by R is preferably position 4. The number of the substituent in the aromatic hydrocarbon group 25 represented by R 11 , which may have the substituent is not particularly limited, and is preferably one to two. [0045] Preferable examples of R may include 4 methylphenyl group and 4-dimethylaminophenyl group. [0046] In the general formula (1-2), R 12 1 represents a 30 hydrogen atom, an alkyl group, or an alkoxyalkyl group, R 122 represents a phenyl group which may have a substituent, and R and R14 each independently represent a hydrogen atom or an alkyl group.

Docket No. PNPA-12278-PCT 21 [0047] In the general formula (1-2), R' 2 1 represents a hydrogen atom, an alkyl group, or an alkoxyalkyl group, and preferably represents the alkyl group or the alkoxyalkyl group. The alkyl group represented by R1 2 1 is preferably an 5 alkyl group having one or more and 4 or less carbon atoms, and more preferably an alkyl group having one or more and 3 or less carbon atoms. Preferable examples of the alkyl group represented by R 1 21 may include ethyl group, methyl group, n-propyl group, n-butyl group, and tert-butyl group. 10 The alkoxyalkyl group represented by R 1 2 1 is preferably an alkoxyalkyl group having one or more and 4 or less carbon atoms, and more preferably an alkoxyalkyl group having one or more and 3 or less carbon atoms, and also preferably a straight alkoxyalkyl group. Preferable examples of the 15 alkoxyalkyl group represented by R may include methoxymethyl group. [0048] In the general formula (1-2), R22 represents an aromatic hydrocarbon group which may have a substituent, preferably represents the aromatic hydrocarbon group having 20 a substituent, and a phenyl group having a substituent is preferable. Alkyl groups, halogen atoms, and alkoxy groups are preferable as the substituent which the aromatic hydrocarbon group represented by R12 may have. The alkyl group and the alkoxy group preferably have one or more and 25 4 or less carbon atoms and preferably have a straight structure. Preferable examples of the substituent which the aromatic hydrocarbon group represented by R22 may have may include methyl group, a chlorine atom, and n-butoxy group. A position to be substituted on the aromatic 30 hydrocarbon group represented by R 122 is preferably position 2 and/or position 4. The number of the substituent in the aromatic hydrocarbon group represented by R1 2 2 is not particularly limited, and is preferably one to two.

Docket No. PNPA-12278-PCT 22 [0049] Preferable examples of R122 may include 4 chlorophenyl group, 4-methylphenyl group, 4-butoxyphenyl group (4-n-butoxyphenyl group), and 2,4-dichlorophenyl group. 5 [0050] In the general formula (1-2), R and R14 each independently represent a hydrogen atom or an alkyl group, and preferably both of them represent the hydrogen atom. [0051] In the general formula (1-3), R1 3 1 represents a hydrogen atom, an alkyl group, or an alkenyl group, R12 10 represents an alkyl group, or an aromatic hydrocarbon group which may have a substituent, and R1 represents an aromatic hydrocarbon group which may have a substituent. [0052] In the general formula (1-3), R 131 represents a hydrogen atom, an alkyl group, or an alkenyl group. The 15 alkyl group and the alkenyl group represented by R 121 preferably are an alkyl group having one or more and 3 or less carbon atoms and are preferably straight. The alkyl group as R is preferably methyl group, and the alkenyl group as R 3 1 is preferably 3-propenyl group. 20 [0053] In the general formula (1-3), R 132 represents an alkyl group, or an aromatic hydrocarbon group which may have a substituent, and preferably represents the aromatic hydrocarbon group which may have a substituent. A phenyl group having a substituent and a phenyl group having no 25 substituent are preferable. The substituent which the aromatic hydrocarbon group represented by R 13 2 may have is preferably a halogen atom and preferably a chlorine atom. A position to be substituted on the aromatic hydrocarbon group represented by R1 3 2 is preferably position 4. The 30 number of the substituent in the aromatic hydrocarbon group represented by R 132 is not particularly limited, and is preferably 0 to 1. Preferable examples of R32 may include 4-chlorophenyl group and phenyl group.

Docket No. PNPA-12278-PCT 23 [0054] In the general formula (1-3), R 133 represents an aromatic hydrocarbon group which may have a substituent, and preferably represents an aromatic hydrocarbon group having a substituent. R 133 preferably represents a phenyl 5 group having a substituent is preferable. The substituent which the aromatic hydrocarbon group represented by R 133 may have is preferably a halogen atom and preferably a chlorine atom. A position to be substituted on the aromatic hydrocarbon group represented by R 33 is preferably position 10 4. The number of the substituent in the aromatic hydrocarbon group represented by R 33 is not particularly limited, and is preferably one. Preferable examples of R 133 may include 4-chlorophenyl group. 211 [0055] In the general formula (2-1), R represents an 15 aromatic hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent, m is 1 or 2, n is 0 or 1, and A represents a nitrogen atom or -CH-. [00561 R211 represents an aromatic hydrocarbon group which may have a substituent or a heterocyclic group which 20 may have a substituent. [0057] Examples of the substituent which the aromatic hydrocarbon group and the heterocyclic group represented by R211 may have may include phenyloxy group. The aromatic hydrocarbon group and the heterocyclic group preferably 25 contain two or more aromatic rings (two or more aromatic rings may be condensed one another). The aromatic hydrocarbon group and the heterocyclic group represented by R are preferably phenyl group, naphthyl group, and indole group, and each need not have the substituent. 30 [0058] Preferable example of R may include 4 phenoxyphenyl group, naphthyl group, and indole group. [0059] In the general formula (2-1), m is 1 or 2 and n is 0 or 1. When m is 2, n is preferably 0. When m is 1, n Docket No. PNPA-12278-PCT 24 may be either 0 or 1. [0060] In the general formula (2-1), A represents a nitrogen atom or -CH-. That is, the compound represented by the general formula (1) is a compound having a triazole 5 ring in its structure when A represents the nitrogen atom, and is a compound having an imidazole ring in its structure when A represents -CH 2

-

[00611 In the general formula (2-1), a preferable combination of the substituents may include a combination 10 in which R 21 1 is naphthyl group, m is 2, n is 0, and A is nitrogen atom; a combination in which R 211 is naphthyl group, m is 2, n is 0, and A is -CH-; a combination in which R 211 is 4-phenoxyphenyl group, m is 1, n is 1, and A is desirably nitrogen atom; and a combination in which R 211 is 15 3-indole group, m is 1, n is 0, and A is desirably nitrogen atom. [00621 In the general formula (2-2), R represents a hydrogen atom, an alkyl group, or a halogenated alkyl group, R represents a hydrogen atom, an alkyl group, or a 20 halogen atom, and p is an integer of 1 to 5. [0063] R 221 represents a hydrogen atom, an alkyl group, or a halogenated alkyl group, and preferably represents the halogenated alkyl group. An alkyl moiety in the halogenated alkyl group preferably has one carbon atom. 25 The alkyl moiety in the halogenated alkyl group is preferably straight. The number of the halogen atoms which the halogenated alkyl group has may be one or more. When the halogenated alkyl group has two or more halogen atoms, two or more halogen atoms may contain different halogen 30 atoms or may contain two or more of the same halogen atom, but preferably the halogenated alkyl group has one halogen atom. Preferable examples of R 221 may include a methyl bromide group.

Docket No. PNPA-12278-PCT 25 [00641 In the general formula (2-2), R represents a hydrogen atom, an alkyl group, or a halogen atom, and preferably represents the halogen atom. The number of the substituent R 2 2 2 is represented by p, which is an integer of 5 1 to 5 and preferably 2. When p is 2 or more, two or more R may be different one another or the same, but are preferably the same substituent. Among them, they are preferably fluorine atoms. A position of a skeleton of the general formula (2-2), to which R 22 2 is bound is not 10 particularly limited, and when p is 2, the binding of R 222 is preferably a binding represented by the following general formula (2-20). In the formula (2-20), R22 is defined as above, and two R 222 may be the same or different. R222

-

(2-20) R222 15 [0065] The compound represented by the general formulae (1-1) to (1-3), the general formulae (2-1) and (2-2) has one or two or more asymmetric carbons in some cases. That is, the compound represented by the general formulae (1-1) to (1-3), the general formulae (2-1) and (2-2) may be any 20 pure form of an optical active material, a diastereomer, any mixture of isomers such as a mixture of two or more diastereomers, and a racemic body, based on the asymmetric carbons. [0066] A form of a salt of the compound represented by 25 the general formulae (1-1) to (1-3), the general formulae (2-1) and (2-2) is not particularly limited, and a form depending on a type of a substituent. Examples the form of the salt may include an acid addition salt. The type of the salt is not particularly limited. Examples of the type Docket No. PNPA-12278-PCT 26 of the salt may include salts with an inorganic acid such as hydrochloric acid and sulfuric acid, salts with organic acid such as p-toluenesulfonic acid, methanesulfonic acid, and tartaric acid, metallic salts such as sodium salts, 5 potassium salts, and calcium salts, salts with organic amine such as triethylamine, and salts with an amino acid such as glycine. [0067] Examples of the compound represented by the general formula (1-1) and the salt thereof may include the 10 followings. [0068] 1-Chlorophenyl-3-(4-methylphenyl)-2-(1,2,4 triazoyl)-2-propene-1-ol (hereinafter referred to as MA73 that has a structure represented by a formula (1-11)). O H CI Ng MA73 15 [0069] 1-(2,2-Dimethylethyl)-3-(4-dimethylaminophenyl) 2-(1,2,4-triazoyl)-2-propene-1-ol (hereinafter referred to as MA65 that has a structure represented by a formula (1 12)).

Docket No. PNPA-12278-PCT 27 0OH r N ... (1-_2) N

N

MA65 [0070] Examples of the compound represented by the general formula (1-2) and the salt thereof may include the followings. 5 [0071] 1-[[2-(4-Chlorophenyl)-4-propyl-1,3-dioxolane-2 yl]methyl]-1H-1,2,4-triazole (hereinafter referred to as SEA10 that has a structure represented by a formula (1-21)). SN(1-21) O O N CI1 SEA10 [0072] 1-[[2-(4-Chlorophenyl)-4-ethyl-1,3-dioxolane-2 10 yl]methyl]-lH-1,2,4-triazole (hereinafter referred to as SEA13 that has a structure represented by a formula (1-22)).

Docket No. PNPA-12278-PCT 28 N (1-22) N N SEA1 3 [0073] 1-[[2-(4-Methylphenyl)-4-propyl-1,3-dioxolane-2 yl]methyl]-1H-1,2,4-triazole (hereinafter referred to as SAR33 that has a structure represented by a formula (1-23)). r """ (1-23) N 5 SAR33 [0074] 4RS-1-[[4-methyl-2-(4-(1-butoxy)phenyl)-1,3 dioxolane-2-yl]methyl] -1H-1,2,4-triazole (hereinafter referred to as KSR179 that has a structure represented by a formula (1-24) ).

Docket No. PNPA-12278-PCT 29 0F0 N N ~... (1-24) N KSR179 [0075] 1-[ [4-Methoxymethyl-2-(2,4-dichlorophenyl)-1,3 dioxolane-2-yl]methyl] -lH-1, 2, 4-triazole (hereinafter referred to as KSR90 that has a structure represented by a 5 formula (1-25)). 0 / (1-25) N KSR90 [0076] Examples of the compound represented by the general formula (1-3) and the salt thereof may include the followings. 10 [0077] 3-(4-Chlorophenyl)-l-phenyl-2-(1,2,4-triazoyl) propane-1-ol (hereinafter referred to as MA31 that has a structure represented by a formula (1-31)).

Docket No. PNPA-12278-PCT 30 OH " " (1-31) N NN C1 MA31 [0078] 4-(4-Chlorophenyl)-2-phenyl-3-(1,2,4-triazoyl) butane-2-ol (hereinafter referred to as MA87 that has a structure represented by a formula (1-32)). OH " (1-32) rN N ., / CI MA87 5 [00791 2,4-di(4-Chlorophenyl)-3-(1,2,4-triazoyl)-butane 2-ol (hereinafter referred to as MA8S that has a structure represented by a formula (1-33)).

Docket No. PNPA-12278-PCT 31 OH CI1 -.-. (1-33) N r \ N CI MA88 [0080] 6-(4-Chlorophenyl)-4-phenyl-5-(1,2,4-triazoyl)-1 hexene-4-ol (hereinafter referred to as SEA22 that has a structure represented by a formula (1-34)). OH OO "". (1-34) N / \ CI 5 SEA22 [0081) Examples of the compound represented by the general formula (2-1) and the salt thereof may include the followings. [0082] 1-(1-Naphthyl)-2-(1H-1,2,4-triazole-1-yl)-ethane 10 (hereinafter referred to as KSR236 that has a structure represented by a formula (2-11)).

Docket No. PNPA-12278-PCT 32 N N N - -- (2-11) KS R236 (0083] 1-(1-Naphthyl)-2-(lH-imidazole-1-yl)-ethane (hereinafter referred to as KSR233 that has a structure represented by a formula (2-12)). NN - " (2-12) 5 KS R233 [00841 1-(3-Indolyl)-2-(1H-1,2,4-triazole-1-yl)-ethane (hereinafter referred to as KSR221 that has a structure represented by a formula (2-13)). rN NN -.. (2-13) I N H KSR221 10 [0085] 1-(4-Phenoxyphenyl)-(1H-1,2,4-triazole-1-yl) methyl ketone (hereinafter referred to as KSR122 that has a structure represented by a formula (2-14)).

Docket No. PNPA-12278-PCT 33 N O r X) .(2-14) 0 INN KS R1 22 [0086] Examples of the compound represented by the general formula (2-2) and the salt thereof may include the following. 5 [0087] 2,4-Difluorophenyl-bromomethyl ketone (hereinafter referred to as KSR51 that has a structure represented by a formula (2-21)). F Br

--

(2-21) F KSR51 [0088] An origin of the compound represented by the 10 general formulae (1-1) to (1-3), the general formulae (2-1) and (2-2) or the salt thereof is not particularly limited. For example, those synthesized by a chemical reaction may be used. Examples of the synthesis methods may include methods described in references such as JP 2000-53657-A, JP 15 3762949-A, and Zeitschriftfur Naturforschung, 44c, pp.85-96, 1989. [0089] The cell differentiation accelerator of the present invention contains the compound represented by the general formulae (1-1) to (1-3), the general formulae (2-1) Docket No. PNPA-12278-PCT 34 and (2-2) or the salt thereof. That is, the cell differentiation accelerator contains one alone or two or more selected from the compound represented by the general formula (1-1), the salt of the compound represented by the 5 general formula (1-1), the compound represented by the general formula (1-2), the salt of the compound represented by the general formula (1-2), the compound represented by the general formula (1-3), the salt of the compound represented by the general formula (1-3), the compound 10 represented by the general formula (2-1), the salt of the compound represented by the general formula (2-1), the compound represented by the general formula (2-2), and the salt of the compound represented by the general formula (2 2). 15 [00901 Examples of the cell may include plant cells. The cell differentiation accelerator of the present invention has an effect of remarkably facilitating the differentiation of a plant cell into a root cell. Therefore, the cell differentiation accelerator of the 20 present invention is useful as an adventitious root formation accelerator. [0091] The adventitious root formation accelerator for the plants of the present invention can contain the compound represented by the general formulae (1-1) to (1-3), 25 the general formulae (2-1) and (2-2) or the salt thereof, and may contain other components such as other adventitious root formation accelerator, if necessary as long as the component is not contrary to the object of the present invention. 30 [0092] The adventitious root formation accelerator of the present invention exerts the effect of facilitating the formation of the adventitious root when is present upon cultivating the plant.

Docket No. PNPA-12278-PCT 35 [0093] A type of the plant is not particularly limited. The plants can be classified into woody plants and herbaceous plants, the present invention can be applied to any of them, is preferably applied to the woody plants, and 5 more preferably applied to the woody plants that are inferior in ability to take root to the herbaceous plants. Examples of the woody plants may include the plants belonging to genera Eucalyptus, Pinus, Cryptomeria such as Cryptomeria japonica, Prunus such as Prunus spp., Prunus 10 mume, Prunus tomentosa, Avocado, Mangifera such as Mangifera indica, Acacia, Myrica, Quercus such as Quercus acutissima, Vitis, Malus, Rosa, Camellia such as Camellia sinensis, Jacaranda such as Jacaranda mimosifolia, Persea such as Persea americana, Pyrus such as Pyrus serotina 15 Rehder, Pyrus pyrifolia, Santalum such as Santalum album (sandal wood). When applied to the plants such as Eucalyptus, Pinus, Cryptomeria japonica, cherries, mangoes, avocadoes, acacia, Myrica rubura, Quercus acutissima, grapes, apples, roses, Camellia, Camellia sinensis, Prunus 20 mume, Prunus tomentosa, Jacaranda mimosifolia, the adventitious root formation accelerator can exert the effect of the present invention more effectively. Among them, preferable are the plants belonging to genera Eucalyptus, Pinus, Cryptomeria, Camellia, Mangifera, and 25 Persea, and more preferable are Eucalyptus, Pinus, Cryptomeria, Camellia sinensis, and Avocado known as hardly rooting plants, and still more preferable is Eucalyptus. [0094] As Eucalyptus plants, Eucalyptus known as the hardly rooting plant is preferable, and Eucalyptus globulus 30 and silver Dollar Gum are more preferable. Examples of applicable herbaceous plants in the present invention may include but are not limited to plants belonging to families Cruciferae, Solanaceae, Poaceae, and Docket No. PNPA-12278-PCT 36 Fabaceae . As described above, the present invention can be applied to food productive plants that include grains such as rice and wheat, beans and maize together with vegetables such as Solanaceae plants, and thus is greatly 5 anticipated in terms of food productive technology in future. Among the plants belonging to families Cruciferae, Solanaceae, Poaceae, and Fabaceae, Arabidopsis thaliana, Nicotiana tabacum, Oryza sativa, and Lotus corniculatus var. japonicus are broadly and commonly used as model plants, 10 and thus are greatly anticipated to contribute to progress of research and development. [0095] The plant may be a whole plant body or a part thereof, but is typically the part of the plant body and preferably a shoot in terms of expecting to form the 15 adventitious root. [0096] The shoot refers to a entire tissue having the ability to take root. Examples of the tissues may include tissues such as branches, stems, apical buds, axillary buds, adventitious buds, leaves, cotyledons, hypocotyls, 20 adventitious germs, and shoot primordia, which are parts of organs. An origin of the shoot is not particularly limited, may be obtained from a plant individual grown in a green house or outdoor, may be a cultured tissue obtained by a tissue culture method, or may be a part of tissue from a 25 native plant body. The shoot can be acquired efficiently from a mother plant for the scion or a multiple shoot. Among them, the scion (scion obtained from the mother plant), the multiple shoot obtained by sterilely culturing an organ collected from the mother plant, or stems and 30 leaves obtained by sterilely culturing the above organ are preferable. [0097] The multiple shoot can be induced by cutting off a bud such as an apical bud or an axillary bud from a plant Docket No. PNPA-12278-PCT 37 from which a clone seedling is to be produced by applying the present invention, and culturing this. The multiple shoot may be formed by sterilely culturing the organ collected from the mother plant according to the method and 5 the condition described in JP Hei-8-228621-A. The method and condition are approximately as follows. First, a tissue of a bud such as an apical bud or an axillary bud is collected from a plant that is a material, and the surface of the collected tissue is sterilized by immersing the 10 tissue in a sodium hypochlorite aqueous solution in which an effective amount of chlorine is about 0.5 to 4% or a hydrogen peroxide aqueous solution in which an effective amount of chlorine is about 5 to 15% for about 10 to 20 minutes. Subsequently, this tissue is washed with 15 sterilized water, and put into a solid medium to open a boll of the bud. Then the multiple shoot is formed by sub culturing growing stems and leaves in medium having the same composition. When the tissue such as the axillary bud from genus Eucalyptus or Acacia is used, it is preferable 20 to use Murashige and Skoog (hereinafter abbreviated as MS) medium containing 1 to 5% by weight of sucrose, about 0.02 mg/L or more and about 1 mg/L or less of benzyladenine (hereinafter abbreviated as BA) as a plant hormone, about 0.2% by weight or more and about 0.3% by weight of gellan 25 gum or 0.5% by weight or more and about 1% by weight or less of agar, or modified MS medium in which contents of ammonium nitrate and potassium nitrate are reduced by half as the medium. The shoot actively extends from the multiple shoot thus formed. The multiple shoot itself can 30 be maintained and grown by appropriately dividing and culturing in the same medium as that used for the formation of the multiple shoot. [0098] Meanwhile, the scion may also be used as the Docket No. PNPA-12278-PCT 38 shoot. Typically, the adventitious root formation accelerator exerts its effect when given to the scion. The scion may be at least a part of a plant. Examples of the scion may include branches such as green woods (branches 5 extended in a current year) and hard woods (branches extended before the previous year); buds such as apical buds and axillary buds; leaves, cotyledons; and hypocotyls. In the case of the woody plants, the green branch and the hard branch are typically used for the scion, and in the 10 case of herbaceous plants, the leaf and the bud are typically used for the scion, but the scion is not limited thereto. [0099] A method of cultivating the plant in the presence of the adventitious root formation accelerator of the 15 present invention is not particularly limited, and can be appropriately selected depending on the type, a site, and a condition of the plant. Specifically, Examples of the method include a method of culturing the plant (preferably the shoot) in the medium for rooting containing the 20 adventitious root formation accelerator; and a method of contacting a solution containing the adventitious root formation accelerator with the plant (preferably the shoot). When the cultured tissue obtained by the tissue culture method is used as the shoot, the former is preferable, and 25 when the scion is used as the shoot, both of the former and the latter are preferable. It is of course possible to combine both the methods exemplified above, i.e., to employ a method of contacting the solution containing the adventitious root formation accelerator with the plant as 30 the plant is cultured in the medium for rooting containing the adventitious root formation accelerator. [0100] When the plant is cultured in the medium for rooting containing the adventitious root formation Docket No. PNPA-12278-PCT 39 accelerator, a concentration of the adventitious root formation accelerator in the medium for rooting is preferably about 0.01 jiM or more and about 2000 pM or less, more preferably about 0.01 jiM or more and about 500 iM or 5 less, and particularly preferably about 0.1 iM or more and about 150 pM or less. [0101] When the plant is cultured in the medium for rooting, a support may be used as described later. When a support such as a porous molded article with less 10 adsorption of an active ingredient is used as the support, an amount of the adventitious root formation accelerator to be added to the medium for rooting is preferably about 0.01 pM or more and about 100 iM or less, more preferably about 0.05 jM or more and about 50 jiM or less, and particularly 15 preferably about 0.1 iM or more and about 10 ptM or less. [0102] A method of contacting the solution containing the adventitious root formation accelerator (adventitious root formation accelerator solution) with the plant (preferably the shoot) is not particularly limited, and can 20 be appropriately selected depending on the type, the site, the condition, and a cultivation method of the plant. Examples of such a method may include a method of spraying the adventitious root formation accelerator solution directly to the shoot, and a method of wetting the support 25 with the adventitious root formation accelerator solution. [0103] The adventitious root formation accelerator solution may be prepared by dissolving the adventitious root formation accelerator in an appropriate solvent (e.g., water). Example of the water may include deionized water, 30 distilled water, reverse osmotic water, tap water, and any of them may be used. The concentration of the adventitious root formation accelerator in the adventitious root Docket No. PNPA-12278-PCT 40 formation accelerator solution is preferably about 0.01 ptM or more and about 2000 pLM or less, more preferably about 0.05 p.M or more and about 500 p.M or less, and still more preferably about 0.1 pM or more and about 150 ptM or less. 5 [0104] When the adventitious root formation accelerator solution is sprayed directly to the plant (preferably the shoot), the adventitious root formation accelerator solution may be misted onto a part of or all of the plant using a spray. The amount of the adventitious root 10 formation accelerator solution to be sprayed depends on the concentration of the adventitious root formation accelerator in the adventitious root formation accelerator solution, and can not be defined necessarily, but is preferably about 0.5 mL or more and about 5.0 mL or less 15 and more preferably about 1.0 mL or more and about 3.0 mL or less per one shoot in general. A spray frequency may be once or twice or more, but it is preferable to at least spray upon starting the cultivation. Further depending on a cultivation condition, the solution may be sprayed 20 additionally and appropriately (e.g., every several days (2 to 3 days) during the cultivation period. [0105] Examples of a method of wetting the support with the adventitious root formation accelerator solution may include a method of sprinkling the adventitious root 25 formation accelerator solution from above the support and a method of placing the support on a bottom of a vessel filled with the adventitious root formation accelerator solution, which is then affused from a bottom surface. When the adventitious root formation accelerator solution 30 is sprinkled from above the support, the amount of the adventitious root formation accelerator solution to be sprinkled from the above is preferably about 1.0 mL or more Docket No. PNPA-12278-PCT 41 and about 30 mL or less and more preferably about 5 ml or more and about 10 mL or less per one plant (preferably one shoot). When the adventitious root formation accelerator solution is affused from the bottom surface, the 5 adventitious root formation accelerator solution may substantially evenly wet the support. When the support is wetted with the adventitious root formation accelerator solution, the medium for rooting is separately prepared in addition to the adventitious root formation accelerator 10 solution, and the support may be wetted with the both of them. [0106] In the present invention, the medium for rooting means a medium used for taking root from the plant (preferably the shoot). The medium for rooting preferably 15 contains silver ion and/or an antioxidant, and more preferably contains both the silver ion and the antioxidant. The silver ion may be added as a silver compound (silver ion source) such as silver thiosulfate (STS, AgS 4

O

6 ) and silver nitrate into the medium. Among them, STS is 20 preferable as the silver ion source used in the present invention because when added to the medium to culture the shoot, STS facilitates healthy rooting and extension of the root. It is thought that this is because the silver ion derived from STS takes a form of thiosulfate ion and is 25 negatively charged in the medium. A concentration of the silver ion to be added in the medium for rooting varies depending on the type of the silver ion and the other culture condition, but the concentration as the silver ion source is preferably about 0.5 pM or more and about 6 pM or 30 less and more preferably about 2 p.M or less and about 6 p.M or less. [0107] Meanwhile, publicly known ones such as ascorbic acid and sulfite salts may be used as the antioxidant.

Docket No. PNPA-12278-PCT 42 Among them, the ascorbic acid is preferable as the antioxidant used in the present invention because its residual effect in the medium is low. The concentration of the antioxidant to be added to the medium for rooting is 5 preferably about 5 mg/L or more and about 200 mg/L or less and more preferably about 20 mg/L or more and about 100 mg/L or less. [0108] The medium for rooting used in the present invention may include ingredients such as inorganic 10 ingredients, carbon sources, vitamins, amino acids, and plant hormones in addition to the above ingredients. [0109] Examples of the inorganic ingredient may include Elements such as nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, manganese, zinc, boron, 15 molybdenum, chlorine, iodine, and cobalt, and inorganic salts containing one or more selected from these elements. Examples of the inorganic salts may include inorganic salts such as potassium nitrate, ammonium nitrate, ammonium chloride, sodium nitrate, potassium monohydrogen phosphate, 20 sodium dihydrogen phosphate, potassium chloride, magnesium sulfate, ferrous sulfate, ferric sulfate, manganese sulfate, zinc sulfate, copper sulfate, sodium sulfate, calcium chloride, magnesium chloride, boric acid, molybdenum trioxide, sodium molybdate, potassium iodide, and cobalt 25 chloride, and hydrates of one or more inorganic salts selected from these inorganic salts. One can be selected or two or more can be selected from the above examples to use alone or in combination as the inorganic ingredient(s). [0110] It is preferable to contain nitrogen, phosphorus, 30 and potassium as essential elements in the medium for rooting used in the present invention. Thus, nitrogen, phosphorus, potassium, the inorganic salts containing nitrogen, the inorganic salts containing phosphorus, and Docket No. PNPA-12278-PCT 43 the inorganic salts containing potassium are preferable, and nitrogen, phosphorus, potassium, and the inorganic salts containing nitrogen are more preferable among the examples of the above inorganic ingredients. When one 5 inorganic ingredient is added, its concentration in the medium for rooting is preferably about 0.1 iM or more and about 100 mM or less and more preferably about 1 pM or more and about 100 mM or less. When two or more ingredients in combination are added, the concentration of each ingredient 10 in the medium for rooting is preferably about 0.1 iM or more and about 100 mM or less and more preferably about 1 pM or more and about 100 mM or less. [0111] Carbohydrates such as sucrose and derivatives thereof; organic acids such as fatty acids; primary 15 alcohols such as ethanol may be used as the carbon source. One can be selected from the above examples to use as the carbon source. Two or more can be selected from the above examples to use in combination as the carbon source. The amount of the carbon source to be added into the medium for 20 rooting is preferably about 1 g/L or more and about 100 g/L or less and more preferably about 10 g/L or more and about 100 g/L or less. However, when the plant is cultured with supplying carbon dioxide gas, the medium need not contain the carbon source and it is preferable to contain no carbon 25 source. The organic compound such as succrose capable of being the carbon source is also the carbon source for microorganisms. Thus, when the medium containing the organic compound is used, it is necessary to culture under a sterile environment. However, by using the medium 30 containing no carbon source, it becomes possible to culture under a non-sterile environment. [0112] Examples of vitamins may include biotin, thiamine Docket No. PNPA-12278-PCT 44 (vitamin Bl), pyridoxine (vitamin B4), pyridoxal, pyridoxamine, calcium pantothenate, inositol, nicotinic acid, nicotinate amide, and riboflavin (vitamin B2). One can be selected from the above examples to use alone as the 5 vitamins. Two or more can be selected from the above examples to use in combination as the vitamins. When one vitamin is used, its concentration in the medium for rooting is preferably about 0.01 mg/L or more and about 200 mg/L or less and more preferably about 0.02 mg/L or more 10 and about 100 mg/L or less. When two or more vitamins in combination are used, the concentration of each vitamin in the medium for rooting is preferably about 0.01 mg/L or more and about 150 mg/L or less and more preferably about 0.02 mg/L or more and about 100 mg/L or less. 15 [0113] Examples of amino acids may include glycine, alanine, glutamic acid, cysteine, phenylalanine, and lysine. One can be selected from the above examples to use alone as the amino acid. Two or more can be selected in combination as the amino acid. When one amino acid isused, its 20 concentration in the medium for rooting is preferably about 0.1 mg/L or more and about 1000 mg/L or less. When two or more amino acids in combination are used, the concentration of each amino acid in the medium for rooting is preferably about 0.2 mg/L or more and about 1000 mg/L or less. 25 [0114] Examples of the plant hormones may include auxins and/or cytokinins. Examples of the auxins may include naphthaleneacetic acid (NAA), indoleacetic acid (IAA), p chlorophenoxyacetic acid, 2,4-dichlorophenoxyacetic acid (2, 4D), indolebutyric acid (IBA), and derivatives thereof. 30 One or more or two or more can be selected from them to use in combination. Benzyladenine (BA), kinetin, zeatin, and derivatives thereof are exemplified as cytokinins. One or more or two or more can be selected from them to use in Docket No. PNPA-12278-PCT 45 combination. Auxins alone, cytokinins alone, or the combination of auxin and cytokinin may be used as the plant hormone. When one plant hormone is used, its concentration in the medium for rooting is preferably about 0.01 mg/L or 5 more and about 10 mg/L or less and more preferably about 0.02 mg/L or more and about 10 mg/L or less. When two or more plant hormones are used, the concentration of each plant hormone in the medium for rooting is preferably about 0.01 mg/L or more and about 10 mg/L or less and more 10 preferably about 0.02 mg/L or more and about 10 mg/L or less. [0115] In the present invention, the adventitious root formation accelerator is added as needed, in addition the silver ion and/or the antioxidant may further be added, and 15 further the carbon source and/or the plant hormone may appropriately be added to the known medium as the medium for culturing the plant tissue to use as the medium for rooting. Examples of such a medium for culturing the plant tissue may include MS medium, Linsmeier-Skoog medium, White 20 medium, Gamborg B-5 medium, and Nitsch/Nitsch medium. MS medium and Gamborg B-5 medium are preferable among them. These media are appropriately diluted if necessary for the use. [01161 The above medium for rooting may be a liquid 25 medium or a solid medium, but the liquid medium is more preferable in terms of work efficiency and less scratch of roots upon transplant. The liquid medium may be prepared by mixing a medium composition and directly used. The solid medium may be used by solidifying with a solidifying 30 agent such as agar and gellan gum simultaneously with or after preparing by mixing the medium composition as with the liquid medium. The amount of the solidifying agent to be added to the medium varies depending on the type of the Docket No. PNPA-12278-PCT 46 solidifying agent and the composition of the medium. When the solidifying agent is agar, the amount to be added is preferably 0.5% by weight or more and 1% by weight or less. When the solidifying agent is gellan gum, the amount to be 5 added is preferably 0.2% by weight or more and 0.3% by weight or less. [0117] A method of putting a cuttage of the plant (preferably the shoot) in the medium for rooting can be appropriately selected depending on a culture condition 10 such as the type of the medium. When the medium for rooting is the solid medium, a base of the shoot may be directly put in the medium for rooting and cultured. Meanwhile when the medium for rooting is the liquid medium, the base of the shoot may be put in the support wetted with 15 the medium for rooting as described later to culture the shoot. It is also preferable for enhancing a rooting rate to give a physical stimulation such as a scratch the base of the shoot when the shoot is put in the medium for rooting. The base of the shoot means one end of the shoot, 20 which is a region where the root is formed, that is, a side opposite to an end where the leaf is formed. When the multiple shoot is used as the shoot, the base of the shoot is a region having a cut surface produced when the multiple shoot is divided. A size (largeness, shape, and the like) 25 of a scratch on the base of the shoot is not particularly limited. For example, it is preferable to make a scratch like a cross shape when the base of the multiple shoot as the shoot (aforementioned cut surface) is seen from a front direction. A tool such as a scissors or a knife can be 30 used for making a scratch. [0118] The support in the present invention is the support to support the plant (preferably the shoot). When the solid medium is used as the medium for rooting, no Docket No. PNPA-12278-PCT 47 support is needed, but in the case other than it, the support is typically utilized. [0119] The support in which the shoot may be kept to be put during the period of the cultivation is preferable. 5 When the liquid medium for rooting is used for the cultivation, the liquid medium is typically used by wetting the support with it. Thus, the support capable of being wetted with the liquid is preferable, and among them, the support capable of being substantially evenly wetted with 10 the adventitious root formation accelerator solution or the liquid medium containing the adventitious root formation accelerator is preferable. When the liquid medium is used as the medium for rooting, the liquid medium containing no adventitious root formation accelerator solution and the 15 adventitious root formation accelerator solution may be added separately to the support, or the previously prepared liquid medium containing the adventitious root formation accelerator may be added to the support. The support conventionally and commonly used can be used as the support, 20 which is not particularly limited. Examples of the support may include natural soils such as sands and Akadama soil; artificial soils such as carbonized chaff, coconut fiber, vermiculite, pearlite, peat moss and glass beads; and porous molded articles such as foamed phenol resin and rock 25 wool. Such a support may be placed in a culture vessel and wetted with the adventitious root formation accelerator solution or the liquid medium containing the adventitious root formation accelerator to prepare a rooting bed. When the medium for rooting is the solid medium, the rooting bed 30 may be prepared by directly placing the solid medium in the culture vessel. [0120] In the present invention, the culture vessel for housing the medium for rooting or the support may be used.

Docket No. PNPA-12278-PCT 48 The culture vessel conventionally and commonly used can be used as the culture vessel, which is not particularly limited. Example of the culture vessel may include pots for raising seedlings and plug trays. The culture vessel 5 may be a closed type or an opened type; however, the closed type is preferable. The sprayed adventitious root formation accelerator solution can be retained by using the closed type of the culture vessel. It also becomes easy to keep the humidity in the environment surrounding the shoot 10 and a clone seedling formed therefrom. (01211 When a branch is used as a shoot, it is preferable to use the closed type of the culture vessel as the culture vessel. This makes it easy to place the shoot under the high humidity. Thus, transpiration from leaves 15 on the branch is reduced, and a partial removal of leaves conventionally performed can be omitted. [0122] More preferably the carbon dioxide gas may be supplied into the culture vessel. Example of the vessel may include a vessel having an opening covered with a 20 carbon dioxide-permeable membrane. The humidity in the culture environment can also be controlled easily by the use of the vessel having the opening covered with the carbon dioxide-permeable membrane. A shape of the opening is not particularly limited. A material for the carbon 25 dioxide-permeable membrane is not particularly limited, and examples of the material may include polytetrafluoroethylene. A pore size of the membrane is not particularly limited, and examples of the pore size may include the pore size of about 0.1 .m or more and about 1 30 jim or less. [01231 A cultivation condition when the plant is cultivated is not particularly limited as long as the root can be taken from the plant. The cultivation condition Docket No. PNPA-12278-PCT 49 varies depending on the type, the site, the condition of the plant, the type of the medium for rooting and the like, and is difficult to be defined completely, but for example, the temperature is more preferably about 23*C or higher and 5 about 28*C or lower. A light intensity is represented as a photosynthesis effective photon flux density, and is preferably about 10 imol/m 2 /s or more and about 1000 mol/m 2 /s or less and more preferably about 50 mol/m 2 /s or more and about 500 pLmol/m 2 /s or less. In any case, the 10 rooting from the shoot can be observed in about two weeks or more and within about 5 weeks. [0124] The cultivation is carried out under an irradiation with the light preferably containing a wavelength component of about 650 nm or more and about 670 15 nm or less and a wavelength component of about 450 nm or more and about 470 nm or less at a ratio of 9:1 to 7:3 and more preferably containing these wavelength components at a ratio of 9:1 to 8:2. The rooting from the plant (preferably the shoot) can further be facilitated by the 20 cultivation under the irradiation with the light containing such wavelength components. [0125] Further it is preferable to supply the carbon dioxide gas at typically 300 ppm or more and 2000 ppm or less and preferably 800 ppm or more and 1500 ppm or less 25 into the cultivation environment. The amount of the carbon dioxide gas to be supplied may be controlled by placing the culture vessel having the carbon dioxide-permeable membrane at the opening in an equipment such as an artificial climate chamber in which the concentration of carbon 30 dioxide is regulated within the above range. [0126] The humidity is preferably 80% or more and more preferably 85% or more. The rooting from the plant can be Docket No. PNPA-12278-PCT 50 facilitated by controlling to this humidity. An upper limit thereof is not particularly limited. [0127] On the contrary, when a scion is used as a shoot, it is preferable to shield the light. A light shielding 5 rate is preferably 30% or more and 70% or less and more preferably 40% or more and 60% or less. [0128] As described above, the adventitious root can be taken from the plant using the adventitious root formation accelerator of the present invention. One taking the 10 adventitious root is typically referred to as a clone seedling. The cultivation is continued for a certain period (depending on the condition such as the type, the site, and the state of the plant, and for example, 10 days or more and 90 days or less in the case of Eucalyptus) 15 using the adventitious root formation accelerator of the present invention, the root is grown, and this is transplanted in the vessel or cultivating soil such as nursery and bred to make a seedling capable of being used for the predetermined purpose such as forestation. The 20 conditions such as the cultivating soil, the temperature upon breeding the seedling, and the light intensity may be set appropriately to be suitable for the plant to be rooted. When the root is taken from the shoot derived from the cultured tissue such as adventitious bud or shoot primordia, 25 it is typically necessary to pass a process of acclimation before transplanting to the seedling raising vessel or the cultivating soil such as the nursery. [0129] The cell differentiation accelerator of the present invention is useful as the adventitious root 30 formation accelerator as described above. An acceleratory effect on the adventitious root formation in the present invention is speculated to be based on the effect described below. Thus, the compound represented by any of the Docket No. PNPA-12278-PCT 51 general formulae (1-1), (1-2), (1-3), (2-1), and (2-2) or the salt thereof is also useful as an active ingredient for a plant hormone activity accelerator. The plant hormone activity accelerator can also further be restated as a 5 plant hormone synthesis accelerator, a plant hormone metabolism (degradation) inhibitor, or a plant hormone metabolism (degradation)-related P450 gene expression inhibitor. [0130] The plant hormone which the plant hormone 10 activity accelerator can target is a substance capable of being produced by the plant in plant growth regulatory substances and a substance that can regulate a physiological process of the plant even at low concentration. Examples of the plant hormone may include 15 but are not limited to auxins, gibberellin, cytokinins, abscisic acid, ethylene, and brassinosteroid. For example, the adventitious root formation accelerator of the present invention is predicted to include those that facilitate the activity of the plant hormone involved in the formation of 20 the adventitious root of the plant. Representative examples of such hormones may include auxins. Examples of auxins are as described above. A method of confirming whether a certain compound has or not the acceleratory effect on the plant hormone activity is not particularly 25 limited. For example, when the plant hormone is auxin, the effect of facilitating the activity of auxins can be confirmed by confirming to have a P-glucuronidase (GUS) activity by actually allowing auxin to act upon a gene recombinant plant such as Arabidopsis thaliana in which an 30 auxin inducible reporter gene such as DR5::GUS has been introduced. [0131] [Effect] In the present invention, a root can be taken from a Docket No. PNPA-12278-PCT 52 shoot of a plant by cultivating the shoot in the presence of the adventitious root formation accelerator. A reason for it is speculated as follows. [0132] The compound represented by any of the general 5 formulae (1-1), (1-2), (1-3), (2-1) and (2-2) or the salt thereof is believed to have an inhibitory effect on a P450 gene. Its acceleratory effect of the adventitious root formation is believed to be involved in any form of auxins' actions such as facilitation of activity, synthesis of 10 auxins, and inhibition of metabolism (degradation) of auxins in the plant tissue. Examples of auxins are as described already. Here, the P450 gene is a gene encoding cytochrome P450. Cytochrome P450 is a group of hem proteins broadly distributed in the living world from 15 microorganisms, plants to animals. Reduced cytochrome P450 is bound to carbon monoxide to exhibit a characteristic absorbance spectrum having a maximum absorbance at 450 nm. Substances referred to as cytochrome P450 have an oxygen addition enzyme activity in a monooxygenase mode, but are 20 different in substrate specificity in a reaction to be catalyzed. However, as a result of comparison of primary structures and high-order structures in protein levels, it is believed that they are members in a gene family differentiated and diversified from one common ancestral 25 gene in a biological evolution process. [0133] Extremely many molecular species are known as cytochrome P450. The number of P450 genes reported in higher plants is 273 in Arabidopsis thaliana for which genome project was completed and 458 in Oryza sativa. 30 Compared them with 83 in Caenorhabditis elegans, 89 in Drosophyla melanogaster, and 57 in Homo sapiens, it is found that the number of the P450 gene is extremely many in the higher plants.

Docket No. PNPA-12278-PCT 53 [0134] The P450 gene is involved in many functions such as secondary metabolism, metabolism of chemical herbicides, and control of growth and differentiation, the P450 gene responsible for each function is present, and the P450 gene 5 involved in the metabolism of auxins is also known. [0135] [Compound] The present invention provides the compound represented by the general formula (2-1) and the compound represented by the general formula (2-2). 10 [0136] 0 11 R21n -( C H, C H2 N ... (2-1) I N AQ In the general formula (2-1), R represents an aromatic hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent, m is 1 or 15 2, n is 0 or 1, and A represents a nitrogen atom or -CH-. 0 (R2 2 2 R22 ... (2-2) In the general formula (2-2), R 221 represents a hydrogen atom, an alkyl group or a halogenated alkyl group, Rm represents a hydrogen atom, an alkyl group or a halogen 20 atom, and p is an integer of 1 to 5. [0137] The substituents in each general formula and the compound represented by each general formula are the same as those described for the cell differentiation accelerator. 25 EXAMPLES [0138] The present invention will be described in more Docket No. PNPA-12278-PCT 54 detail with reference to following Examples. [0139] [EXAMPLES 1 to 12] Eucalyptus globulus (hereinafter abbreviated as E. globulus simply) was used as a material for a scion. That 5 is, a graft extending to a length of 5 to 20 cm and having 1 to 3 knots and about 2 to 6 leaves was cut out from a mother tree for taking scions to prepare a scion. [0140] A base of the obtained scion was put into a porous support made from a foamed phenol resin (trade name: 10 Oasis supplied from Smithers-Oasis Co.) wetted with 4 times diluted MS medium (composition: 412.5 mg/L of ammonium nitrate, 475 mg/L of potassium nitrate, 42.52 mg/L of potassium dihydrogen phosphate, 0.21 mg/L of potassium iodide, no carbon source was added in this medium) adding 1 15 p.M MA31 (EXAMPLE 1), MA87 (EXAMPLE 2), MA88 (EXAMPLE 3), KSR90 (EXAMPLE 4), KSR179 (1:cis-isomer) (EXAMPLEExample 5), KSR179 (2:trans-isomer) (EXAMPLE 6), SEA10 (EXAMPLE 7), SEA13 (EXAMPLE 8), SEA22 (EXAMPLE 9), SAR33 (EXAMPLE 10), MA65 (EXAMPLE 11), or MA73 (EXAMPLE 12) (each was 20 synthesized according to the methods described in JP 2000 53657-A, Patent No. 3762949, and Zeitschriftfur Naturforschung, 44c, pp. 85-96, 1989), 5 ptM STS (AgS 4 0 6 ) as a silver ion source, 50 mg/L of ascorbic acid as an antioxidant, and 2 mg/L of IBA as a plant hormone, and 25 cultured at a carbon dioxide concentration of 1000 ppm at temperature of 25*C under irradiation with red light containing a wavelength component of 650 nm to 670 nm and a wavelength component of 450 nm to 470 nm at a ratio of 8.2:1.8 and having a photosynthesis effective photon flux 30 density of 51.3 pLmol/m 2 /s for 2 months. A cubic vessel with slightly convexed middle having a maximal dimension of about 10 to 11.5 cm verticalxl0 to 11.5 cm horizontalx10.0 Docket No. PNPA-12276-PCT 55 cm height was used as a culture vessel. A top surface of this culture vessel was provided with one circular opening covered with a membrane having a pore diameter of 0.45 pm and made from polytetrafluoroethylene (trade name: 5 MilliSeal supplied from Millipore). The concentration of the carbon dioxide gas in the culture vessel was the concentration of the carbon dioxide gas (about 1000 ppm) permeated from the membrane of the opening in the culture vessel because the carbon dioxide gas out of the culture 10 vessel permeated the carbon dioxide gas-permeable membrane of the opening in the culture vessel. The culture vessel was irradiated with the red light using CCFL Light Source Unit (trade name) from Nippon Medical and Chemical Instruments Co., Ltd (manufacturer name) as a light 15 irradiation apparatus. The humidity in the culture vessel was controlled by sealing the culture vessel with Parafilm. [0141] Sixteen scions were put in one culture vessel. A rooting rate was calculated from the number of scion samples and the number of shoots from which the root was 20 taken after the culture for 2 months (number of rooting). Results are shown in TABLE 1-1 and FIG. 1. An appearance of rooting in a sample cultured with MA65 for 2 months is shown in FIG. 2-2. [0142] [COMPARATIVE EXAMPLE 1] 25 The sample was cultured in the same manner as in Example 1, except that the medium containing no adventitious root formation accelerator was used. The result is shown in TABLE 1-1 and FIG. 1. An appearance of rooting in a sample cultured in a compound-free condition 30 for 2 months is shown in FIG. 2-1. [0143] [COMPARATIVE EXAMPLES 2 to 5] The sample was cultured in the same manner as in EXAMPLE 1, except that 1.0 P.M brassinazole (Brz) Docket No. PNPA-12278-PCT 56 (COMPARATIVE EXAMPLE 2), 1.0 p1M paclobutrazol (COMPARATIVE EXAMPLE 3), 0.1 iM paclobutrazol (COMPARATIVE EXAMPLE 4), or 5.0 pM paclobutrazol (COMPARATIVE EXAMPLE 5) in place of the adventitious root formation accelerator of the present 5 invention was added to the medium. The results are shown in TABLE 1-2 and FIG. 1. (0144] TABLE 1-1. RESULTS OF ROOTING TEST Compound Rooting rate (%) COMPARATIVE EXAMPLE 1 Compound free 25.0 EXAMPLE 1 MA31 62.5 EXAMPLE 2 MA87 62.5 EXAMPLE 3 MA88 62.5 EXAMPLE 4 KSR90 43.8 EXAMPLE 5 KSR179(1) 43.8 EXAMPLE 6 KSR179(2) 50.0 EXAMPLE 7 SEA10 56.3 EXAMPLE 8 SEA13 87.5 EXAMPLE 9 SEA22 37.5 EXAMPLE 10 SAR33 43.8 EXAMPLE 11 MA65 93.8 EXAMPLE 12 MA73 62.5 10 [0145] TABLE 1-2. RESULTS OF ROOTING TEST COMPOUND ROOTING RATE (%) COMPARATIVE EXAMPLE 2 BRASSINAZOLE 31.2 COMPARATIVE PACLOBUTRAZOL EXAMPLE 3 (1.0 ,.L) 25.0 COMPARATIVE PACLOBUTRAZOL EXAMPLE 4 (0.1 ,iL) 0 COMPARATIVE PACLOBUTRAZOL EXAMPLE (5.0 iL) 0 [0146] As is evident from TABLES 1-1 and 1-2 and FIG. 1, the rooting rate in Eucalyptus was remarkably increased compared with the compound free case (Fig. 2-1). The 15 increased rooting rates were higher than the rooting rate obtained from the case of using Brz or paclobutrazol Docket No. PNPA-12278-PCT 57 conventionally known as a rooting accelerator. In particular, the rooting rate in the case of using SEA13 or MA65 (FIG. 2-2) was around 90%, and the rooting rate in the case of using MA31, MA87, MA88, KSR179 (trans-isomer), 5 SEA10, or MA73 reached near 50%, indicating the remarkable rooting rate. [01471 [EXAMPLE 13] The sample was cultured in the same manner as in EXAMPLE 11, except that Silver Dollar Gum was used as a 10 material for a scion. The result is shown in TABLE 2 and FIG. 3. [0148] [COMPARATIVE EXAMPLE 6] The sample was cultured in the same manner as in EXAMPLE 13, except that the medium containing no 15 adventitious root formation accelerator was used. The result is shown in TABLE 2 and FIG. 3. [0149] TABLE 2. RESULTS OF ROOTING TEST USING SILVER DOLLAR GUM COMPOUND ROOTING RATE (%) EXAMPLE 13 MA65 44.0 COMPARATIVE EXAMPLE 6 COMPOUND FREE 6.0 20 [01501 As is evident from TABLE 2 and FIG. 3, the rooting rate of the Silver Dollar Gum in the case of using MA65 was remarkably higher than in the compound free case. [0151] [EXAMPLE 14] A recombinant of Arabidopsis thaliana (DR5::GUS) in 25 which an auxin responsive promoter (DR5) and a reporter gene (P-glucuronidase (GUS) gene) had been introduced, which had been produced by Tom Guilfoyle et al., was used as a material (Tom Guilfoyle et al., The Plant Cell 9, pp 1963-1971, 1997). DR5::GUS is generally used for observing 30 an accumulated amount and localization of auxin using a GUS Docket No. PNPA-12278-PCT 58 activity as an indicator. A DR5::GUS seed was immersed in 1% hypochlorous acid for 5 minutes to sterilize it, and washed 5 times with sterilized water. Subsequently, the seed was seeded on 1% agar medium containing 1 pM compound 5 MA62, 0.5 time diluted MS medium and 1.5% sucrose, and sterilely grown in a petri dish for one week. Arabidopsis thaliana tissue was immersed in a reaction solution (50 mM sodium phosphate, pH 7.0, methanol) containing 1.0 mM 5 bromo-4-chloro-3-indolyl-5-glucuronide (XGluc), and after 10 degassing, was reacted at 37'C for 24 hours. Subsequently, the GUS activity was observed under a microscope (supplied from Keyence Corporation). The results are shown in FIGs. 4-1 and 4-2. [0152] [COMPARATIVE EXAMPLE 7] 15 The sample was cultured in the same manner as in EXAMPLE 14, except that the medium containing no compound MA65 was used, and the GUS activity was observed. The results are shown in FIGs. 4-3 and 4-4. [0153] The GUS activity was strongly detected over the 20 entire plant in FIGs. 4-1 and 4-2, while the GUS activity was partial and weak in FIGs. 4-3 and 4-4. Thus, it is found that the amount of intracellular auxin was increased when MA65 was used. [0154] As described above, it was demonstrated that the 25 adventitious root formation accelerator of the present invention exerted an excellent rooting effect. It was also demonstrated that the compound MA65 out of the adventitious root formation accelerators of the present invention was involved in facilitation of the auxin activity by 30 inhibition of auxin metabolism (degradation). [0155) [EXAMPLES 15 to 19] Eucalyptus globulus (hereinafter abbreviated as E. globulus simply) was used as a material for a scion. That Docket No. PNPA-12278-PCT 59 is, a graft extending to a length of 5 to 20 cm and having 1 to 3 knots and about 2 to 6 leaves was cut out from a mother tree for taking scions to prepare a scion. [0156] A base of the obtained scion was put into a 5 porous support made from a foamed phenol resin (trade name: Oasis supplied from Smithers-Oasis Co.) wetted with 4 times diluted MS medium (composition: 412.5 mg/L of ammonium nitrate, 475 mg/L of potassium nitrate, 42.52 mg/L of potassium dihydrogen phosphate, 0.21 mg/L of potassium 10 iodide, no carbon source was added in this medium) adding 1 pM KSR 51 (EXAMPLE 15), KSR122 (EXAMPLE 16), KSR233 (EXAMPLE 17), KSR221 (EXAMPLE 18), or KSR236 (EXAMPLE 19) (each was synthesized according to the methods described in JP 2000-53657-A, Patent No. 3762949, and Zeitschriftfur 15 Naturforschung, 44c, pp. 85-96, 1989), 5 pLM STS (AgS406) as a silver ion source, 50 mg/L of ascorbic acid as an antioxidant, and 2 mg/L of IBA as a plant hormone, and cultured at a carbon dioxide concentration of 1000 ppm at temperature of 250C under irradiation with red light 20 containing a wavelength component of 650 nm to 670 nm and a wavelength component of 450 nm to 470 nm at a ratio of 8.2:1.8 and having a photosynthesis effective photon flux density of 51.3 pmol/m 2 /s for 2 months. A cubic vessel with slightly convexed middle having a maximal dimension of 25 about 10 to 11.5 cm verticalxl0 to 11.5 cm horizontalx10.0 cm height was used as a culture vessel. A top surface of this culture vessel was provided with one circular opening covered with a membrane having a pore diameter of 0.45 pm and made from polytetrafluoroethylene (trade name: 30 MilliSeal supplied from Millipore). The concentration of the carbon dioxide gas in the culture vessel was the concentration of the carbon dioxide gas (about 1000 ppm) Docket No. PNPA-12278-PCT 60 permeated from the membrane of the opening in the culture vessel because the carbon dioxide gas out of the culture vessel permeated the carbon dioxide gas-permeable membrane of the opening in the culture vessel. The culture vessel 5 was irradiated with the red light using CCFL Light Source Unit (trade name) from Nippon Medical and Chemical Instruments Co.,Ltd (manufacturer name) as a light irradiation apparatus. The humidity in the culture vessel was controlled by sealing the culture vessel with Parafilm. 10 [0157] Sixteen scions were put in one culture vessel. A rooting rate was calculated from the number of scion samples and the number of shoots from which the root was taken after the culture for 2 months (number of rooting). Results are shown in TABLE 3-1 and FIG. 5. 15 [01581 [COMPARATIVE EXAMPLE 8] The sample was cultured in the same manner as in EXAMPLE 15, except that the medium containing no adventitious root formation accelerator was used. The result is shown in TABLE 3-1 and FIG. 5. 20 [0159] [COMPARATIVE EXAMPLES 9 to 12] The sample was cultured in the same manner as in Example 15, except that 1.0 ptM brassinazole (Brz) (Comparative Example 9), 1.0 gM paclobutrazol (COMPARATIVE EXAMPLE 10), 0.1 ptM paclobutrazol (COMPARATIVE EXAMPLE 11), 25 or 5.0 iM paclobutrazol (COMPARATIVE EXAMPLE 12) in place of the adventitious root formation accelerator of the present invention was added to the medium. The results are shown in TABLE 3-2 and FIG. 5. [0160] Docket No. PNPA-12278-PCT 61 TABLE 3-1. RESULTS OF ROOTING TEST COMPOUND ROOTING RATE (%) COMPARATIVE EXAMPLE 8 COMPOUND FREE 25.0 EXAMPLE 15 KSR51 62.5 EXAMPLE 16 KSR122 56.3 EXAMPLE 17 KSR233 43.8 EXAMPLE 18 KSR221 56.3 EXAMPLE 19 KSR236 56.3 [0161] TABLE 3-2. RESULTS OF ROOTING TEST COMPOUND ROOTING RATE (%) COMPARATIVE EXAMPLE 9 BRASSINAZOLE 31.2 COMPARATIVE PACLOBUTRAZOL EXAMPLE 10 (1.0 gL) 25.0 COMPARATIVE PACLOBUTRAZOL EXAMPLE 11 (0.1 pL) 0 COMPARATIVE PACLOBUTRAZOL EXAMPLE 12 (5.0 pL) 0 5 [0162] As is evident from TABLES 3-1 and 3-2 and FIG. 5, the rooting rate in Eucalyptus in the case of adding any compound was remarkably increased compared with the compound free case. These rooting rates were higher than 10 those in the case of using Brz or paclobutrazol conventionally known as the rooting accelerator. In particular, the rooting rate when KSR51, KSR122, KSR221, or KSE236 was used exceeded 50%, indicating the remarkable rooting rate. 15 [0163] [EXAMPLE 20] The sample was cultured in the same manner as in Example 18, except that the Silver Dollar Gum was used as a material for a scion. The result is shown in TABLE 4 and FIG. 6. 20 [0164] [COMPARATIVE EXAMPLE 13] Docket No. PNPA-12278-PCT 62 The sample was cultured in the same manner as in Example 20, except that the medium containing no adventitious root formation accelerator was used. The result is shown in TABLE 4 and FIG. 6. 5 [0165] TABLE 4. RESULTS OF ROOTING TEST USING SILVER DOLLER GUM COMPOUND ROOTING RATE (%) EXAMPLE 20 KSR221 12.0 COMPARATIVE EXAMPLE 13 COMPOUND FREE 6.0 [0166] As is evident from TABLE 4 and FIG. 6, the rooting rate in the Silver Dollar Gum was much higher in 10 the case of using KSR221 than in the compound free case. [0167) As described above, it was demonstrated that the compound of the present invention exerted the excellent acceleratory effect on the adventitious root formation. 15

Claims

1. A cell differentiation accelerator comprising a compound represented by any of the general formulae (1-1), (1-2), (1-3), (2-1), and (2-2) or a salt thereof: R 1 1 1 R112 ---- ~ ""(-1) N R1''3 r N 5 N wherein Ri represents a hydrogen atom, a hydroxyl group or an alkyl group, R12 represents an alkyl group, or an aromatic 10 hydrocarbon group which may have a substituent, R13 represents an aromatic hydrocarbon group which may have a substituent, and a wavy line represents a cis configuration or a trans configuration; R124 F121 R122 N- N 15 R22>< N " N wherein R represents a hydrogen atom, an alkyl group, or an alkoxyalkyl group, R12 represents an aromatic hydrocarbon group which may 20 have a substituent, and R and R12 each independently represent a hydrogen atom or an alkyl group; Docket No. PNPA-12278-PCT 64 1 310 H R132 (1-3) N R133 NQN wherein R 131 represents a hydrogen atom, an alkyl group, or an alkenyl group, 5 R represents an alkyl group, or an aromatic hydrocarbon group which may have a substituent, and R represents an aromatic hydrocarbon group which may have a substituent; 0 11 R21-( 6(C2 N ... (2-1) 10 wherein R represents an aromatic hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent, m is 1 or 2, 15 n is 0 or 1, and A represents a nitrogen atom or -CH-; and 0 (R222 R 2 21 . -(2-2) wherein R represents a hydrogen atom, an alkyl group, or a Docket No. PNPA-12278-PCT 65 halogenated alkyl group, R represents a hydrogen atom, an alkyl group, or a halogen atom, and p is an integer of 1 to 5. 5

2. The cell differentiation accelerator according to claim 1, wherein: R 1 il represents a hydroxyl group; R12 represents a 4-chlorophenyl group or a t-butyl 10 group; and R 113 represents a 4-methylphenyl group or a 4 dimethylaminophenyl group.

3. The cell differentiation accelerator according to 15 claim 1, wherein: R121 represents an ethyl group, a methyl group, a n propyl group or a methoxymethyl group; R12 represents a 4-chlorophenyl group, a 4 methylphenyl group, a 4-n-butoxyphenyl group or a 2,4 20 dichlorophenyl group; and both R 123 and R1 2 4 represent a hydrogen atom.

4. The cell differentiation accelerator according to claim 1, wherein: 25 R 131 represents a hydrogen atom, a methyl group or a 3 propenyl group; R12 represents a 4-chlorophenyl group or a phenyl group; and R represents a 4-chlorophenyl group. 30

5. The cell differentiation accelerator according to claim 1, wherein: R represents a naphthyl group; Docket No. PNPA-12276-PCT 66 m is 2; and n is 0.

6. The cell differentiation accelerator according to 5 claim 1, wherein: R 21 represents a 4-phenoxyphenyl group; m is 1; n is 1; and A represents a nitrogen atom. 10

7. The cell differentiation accelerator according to claim 1, wherein: Rm 21 represents a 3-indole group; m is 1; 15 n is 0; and A represents a nitrogen atom.

8. The cell differentiation accelerator according to claim 1, wherein: 20 R221 represents a methyl bromide group; R222 represents a fluorine atom; and p is 2.

9. The cell differentiation accelerator according to any 25 one of claims 1 to 8, wherein the cell is a plant cell.

10. The cell differentiation accelerator according to any one of claims 1 to 9, which is an adventitious root formation accelerator for a plant. 30

11. A medium for rooting for a shoot of a plant, containing the cell differentiation accelerator according to any one of claims 1 to 10. Docket No. PNPA-12278-PCT 67

12. A method of producing a clone seedling, wherein a shoot of a plant is cultivated in the presence of the cell differentiation accelerator according to any one of claims 5 1 to 10 and a root is taken from the shoot.

13. A method of producing a clone seedling, wherein a shoot of a plant is cultivated in the medium for rooting according to claim 11 and a root is taken from the shoot. 10

14. A method of facilitating cell differentiation using a compound represented by any of the general formulae (1-1), (1-2), (1-3), (2-1), and (2-2) or a salt thereof: R111 R112 N R13 / N 15 wherein Ri represents a hydrogen atom, a hydroxyl group or an alkyl group, R 11 2 represents an alkyl group, or an aromatic hydrocarbon group which may have a substituent, and 20 R represents an aromatic hydrocarbon group which may have a substituent, and a wavy line represents a cis configuration or a trans configuration; Docket No. PNPA-12278-PCT 68 R 1 4 R121 R 123 N 0 -- (1-2) R 122 N N wherein R represents a hydrogen atom, an alkyl group, or an alkoxyalkyl group, 5 R122 represents an aromatic hydrocarbon group which may have a substituent, and R 123 and R124 each independently represent a hydrogen atom or an alkyl group; R131 OH R1 3 2 -- (1-3) N R133 NQN 10 wherein R represents a hydrogen atom, an alkyl group, or an alkenyl group, R represents an alkyl group, or an aromatic hydrocarbon group which may have a substituent, and 15 R represents an aromatic hydrocarbon group which may have a substituent; 0 I R2ne -(C r-(nC H2 N 1 N wher ein Docket No. PNPA-12278-PCT 69 R211 represents an aromatic hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent, m is 1 or 2, n is 0 or 1, and 5 A represents a nitrogen atom or -CH-; and 0 wherein R represents a hydrogen atom, an alkyl group, or a halogenated alkyl group, 10 R represents a hydrogen atom, an alkyl group, or a halogen atom, and p is an integer of 1 to 5.

15. The method of facilitating the cell differentiation 15 according to claim 14, wherein the cell is a plant cell.

16. The method of facilitating the cell differentiation according to claim 14 or 15, wherein the cell differentiation is facilitation of adventitious root 20 formation in a plant.

17. A novel compound represented by the following general formula (2-1) or (2-2), or a salt thereof: 0 11 Rrer -C t CaH2 tiNcy ar ... (2-1) 1 N Az/ 25 wherein Rm21 represents an aromatic hydrocarbon group which may Docket No. PNPA-12278-PCT 70 have a substituent or a heterocyclic group which may have a substituent, m is 1 or 2, n is 0 or 1, and 5 A represents a nitrogen atom or -CH-; and 0 wherein R represents a hydrogen atom, an alkyl group, or a halogenated alkyl group, 10 R represents a hydrogen atom, an alkyl group, or a halogen atom, and p is an integer of 1 to 5.

18. The compound according to claim 17, wherein: 15 R represents a naphthyl group; m is 2; and n is 0.

19. The compound according to claim 17, wherein:

20 R represents a 4-phenoxyphenyl group; m is 1; n is 1; and A represents a nitrogen atom. 25 20. The compound according to claim 17, wherein: R represents a 3-indole group; m is 1; n is 0; and A represents a nitrogen atom. Docket No. PNPA-12278-PCT 71

21. The compound according to claim 17, wherein: R221 represents a methyl bromide group; R222 represents a fluorine atom; and 5 p is 2.