WO2016006351A1

WO2016006351A1 - Plant resistance inducing control agent, plant resistance inducing control method, plant disease prevention method, insect prevention method, plant growth promoter, microbial infection efficiency promoter, and transgene expression efficiency promoter

Info

Publication number: WO2016006351A1
Application number: PCT/JP2015/065242
Authority: WO
Inventors: 和之平塚; 里江子小倉; 晴登石川
Original assignee: 国立大学法人横浜国立大学
Priority date: 2014-07-09
Filing date: 2015-05-27
Publication date: 2016-01-14
Also published as: JP6652763B2; JPWO2016006351A1

Abstract

A plant resistance inducing control agent containing a compound represented by formula (1) or a salt thereof as an active ingredient. X^1-10: CH, N (however, N is 0-1 in X^1-5 and X^6-10). R¹: C_1-4 straight-chain or branched haloalkyl, halogen, NO₂, CN. R²: C_1-4 straight-chain or branched alkyl, C_2-4 straight-chain or branched alkenyl. R³: H, C_1-4 straight-chain or branched alkyl, C_2-4 straight-chain or branched alkenyl. R⁴: C_1-4 straight-chain or branched alkyl, C_2-4 straight-chain or branched alkenyl, halogen. n: 0-1. m: 0-5. p: 0-5.

Description

Plant resistance induction control agent, plant resistance induction control method, plant disease control method, pest control method, plant growth promoter, microbial infection efficiency promoter, and transgene expression efficiency promoter

The present invention relates to a plant resistance induction control agent, a plant resistance induction control method, a plant disease control method, a pest control method, a plant growth promoter, a microbial infection efficiency promoter, and a transgene expression efficiency promoter.
This application claims priority on July 9, 2014 based on Japanese Patent Application No. 2014-141466 for which it applied to Japan, and uses the content here.

Plants are invaded and attacked by various pathogenic microorganisms such as filamentous fungi, bacteria and viruses. Plants have developed defense mechanisms to combat them. There are various stages in the defense mechanism. First, in the stage before the pathogen invades, the pathogenic invasion is blocked by the physical barrier by the cell wall and the opening and closing of the stoma of the leaves. Plant cells recognize the pathogen invasion even after the pathogen has invaded, and have a mechanism that inhibits the progression of infection by accumulating polysaccharides at the intrusion site (see Ton and Mauch-Mani, 2009). Furthermore, plants have a mechanism that enhances resistance not only at the site of pathogenic infection but also at a non-infected site by transmitting a signal from the infected site to the whole body. This mechanism involves the expression of plant hormones and numerous genes.

As a mechanism for inducing resistance throughout the body, there is systemic acquired resistance (SAR) in which salicylic acid (SA), a plant hormone, is involved in signal transduction, and research has been progressing in recent years. It has been shown that the defense response by SAR can combat a wide range of pathogens to enhance the disease resistance of the plant itself.
SA is mainly known to induce resistance to “active parasitic pathogens”, pathogens that nourish from living cells. In many cases, the parasitic parasite pathogens absorb nutrients from plant cells and coexist with plants. There is a rice blast fungus as an active parasitic fungus.
Compounds that have the activity to induce SAR have been put into practical use as resistance inducers or plant activators, and are mainly used as effective materials for disease control in rice in Japan. In the example of probenazole (trade name oryzate) Even though more than 30 years have passed since the development, there are sales of about 10 billion yen per year. In addition to propenazole, there are a plurality of resistance inducers or plant activators having an activity to induce SAR, and known are paridamycin A (VMA), benzothiadiazole (BTH), thiazinyl (TDL), and isothianyl. ing.

On the other hand, a mechanism for developing disease resistance that works by a different mechanism of action from SAR is also known. Induced Systemic Resistance (ISR) is not dependent on SA, unlike SAR, and is induced by the pathogenesis of disease resistance depending on the plant hormone jasmonic acid (JA). (See FIG. 4). In ISR, it has been found that the defense response gene to be induced and the type of pathogen effective as a resistance target are also different from SAR.
JA mainly induces a resistance response to “septic pathogens”, which are pathogens that nourish from dead cells, and a protective response to “injuries” such as insect damage caused by pests. A representative fungal pathogen is gray mold. Gray mold fungus infects almost all plants, and drug resistant bacteria are very likely to occur. However, a compound having an activity to induce SAR has a poor control effect against rot-causing pathogens, and existing plant activators such as probenazole are ineffective against rot-causing pathogens such as gray mold.
Therefore, if there is a compound having an activity to induce the ISR system, there is a possibility that it can be used as a new pest control material that is effective even for diseases that cannot be dealt with by the existing SAR resistance inducers. However, previous studies have not found low molecular weight compounds having such activity to the extent that they are commercially available. Bestatin (Bestain) is reported to be a compound that specifically activates the JA signal (Non-patent Document 1). So far, hexanoic acid, arachidonic acid, N-acylamide (alkamide) and the like are known as defense activation-inducing compounds by JA / ET signal transduction system (Non-Patent Documents 2 to 4). It has been shown using Arabidopsis that both of these induce the expression of JA responsive genes including PDF1.2 and VSP2 and are effective in suppressing the formation of lesions of gray mold. In addition, in the treatment of hexanoic acid and arachidonic acid, suppression of lesion formation has been observed in tomato as well (Non-patent Document 5). This indicates that JA resistance inducers are effective in controlling gray mold. However, the effectiveness of these drugs also has problems such as the need for high concentration treatment, and they have not been put into practical use as JA-based resistance inducers.

As described above, a plurality of compounds that activate the JA signal have been reported (Non-Patent Documents 1 to 5), but the resistance induction is not so high and has not been put into practical use. From such circumstances, the discovery of a novel compound having activity to induce the ISR system and its application to pest control are expected. In addition, it is known that the SAR system is suppressed by activating the JA signal system, and the SAR system defense response expression is controlled by a highly effective JA signal activator, resulting in the growth and growth of plants. The improvement of foreign gene expression efficiency using pathogens can also be expected.
This invention is made | formed in view of the said situation, and makes it a subject to provide the plant resistance induction control agent which is excellent in plant resistance induction control activity.

In order to solve the above-mentioned problems, the present invention provides a plant resistance induction control agent, a plant resistance induction control method, a plant disease control method, a pest control method, a plant growth promoter, a microorganism infection efficiency promotion having the following characteristics: An agent and a transgene expression efficiency promoting agent are provided.

[1] A plant resistance induction controlling agent comprising a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ each independently represent CH or N (provided that X ¹ , X ² , Any two or more of X ³ , X ⁴ and X ⁵ are not N, and any two or more of X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ are not N).
R ¹ represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R ² represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R ³ represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R ⁴ represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R ¹ and is 0 or 1. m represents the number of R ² and is an integer of 0 to 5, and when m is 2 or more, R ² may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R ⁴ and is an integer of 0 to 5, and when p is 2 or more, R ⁴ may be the same or different from each other. ]
[2] The plant resistance induction controlling agent according to [1], wherein the general formula (1) is a compound represented by the following general formula (1-2).

[In the formula (1-2), X ¹ , X ⁷ , R ¹ , R ² , R ³ , R ⁴ , n, m and p have the same meaning as described above. ]
[3] The plant resistance induction controlling agent according to [1] or [2], wherein the general formula (1) is a compound represented by the following general formula (3-2-2).

[In the formula (3-2-2), R ¹ , R ² , R ³ , R ⁴ , n, m and p have the same meaning as described above. ]
[4] A plant resistance induction control method comprising bringing a plant resistance induction control agent according to any one of [1] to [3] into contact with a plant.
[5] A plant disease control method comprising using the plant resistance induction control method according to [4].
[6] A pest control method comprising using the plant resistance induction control method according to [4].
[7] A plant growth promoter containing a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ each independently represent CH or N (provided that X ¹ , X ² , Any two or more of X ³ , X ⁴ and X ⁵ are not N, and any two or more of X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ are not N).
R ¹ represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R ² represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R ³ represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R ⁴ represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R ¹ and is 0 or 1. m represents the number of R ² and is an integer of 0 to 5, and when m is 2 or more, R ² may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R ⁴ and is an integer of 0 to 5, and when p is 2 or more, R ⁴ may be the same or different from each other. ]
[8] A microorganism infection efficiency promoter containing a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ each independently represent CH or N (provided that X ¹ , X ² , Any two or more of X ³ , X ⁴ and X ⁵ are not N, and any two or more of X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ are not N).
R ¹ represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R ² represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R ³ represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R ⁴ represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R ¹ and is 0 or 1. m represents the number of R ² and is an integer of 0 to 5, and when m is 2 or more, R ² may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R ⁴ and is an integer of 0 to 5, and when p is 2 or more, R ⁴ may be the same or different from each other. ]
[9] A transgene expression efficiency promoter containing a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ each independently represent CH or N (provided that X ¹ , X ² , Any two or more of X ³ , X ⁴ and X ⁵ are not N, and any two or more of X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ are not N).
R ¹ represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R ² represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R ³ represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R ⁴ represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R ¹ and is 0 or 1. m represents the number of R ² and is an integer of 0 to 5, and when m is 2 or more, R ² may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R ⁴ and is an integer of 0 to 5, and when p is 2 or more, R ⁴ may be the same or different from each other. ]

According to the plant resistance induction control agent of the present invention, plant diseases can be reduced. Moreover, according to the plant resistance induction | guidance | derivation control method of this invention, a plant disease can be reduced by the simple method of exposing a plant resistance induction | guidance | derivation control agent to the plant used as object. In addition, this method can control (also referred to as prevention or treatment) that a target plant is infected with a pathogenic bacterium, and exhibits excellent control effects against pests.
Moreover, a plant resistance induction | guidance | derivation control agent can be used as a plant growth promoter, and can promote the growth of a plant by this.
In addition, the plant resistance induction control agent can be used as a microbial infection efficiency promoter, thereby suppressing the expression of SAR defense response and improving the artificial microbial infection efficiency to the plant body. When a gene is introduced, the expression efficiency of the introduced gene can be improved.

It is the result of having evaluated the control effect of the compound X with respect to a gray mold fungus in an Arabidopsis thaliana individual. It is the result of having evaluated the control effect of the compound X with respect to a gray mold fungus in a tomato mature individual. It is the result of having evaluated the control effect of the compound X with respect to a gray mold fungus in a cucumber mature individual. It is a figure explaining the signal transduction pathway in connection with disease resistance. It is a measurement result of SA responsive gene expression by the compound X process with respect to Arabidopsis thaliana which has PR-1a :: Fluc. It is a photograph which shows the observation result of the growth promotion effect by the compound X process with respect to a cabbage. This is a result of evaluating the effect of improving compound infection efficiency and transgene expression efficiency by compound X treatment on tobacco.

Hereinafter, preferred examples of the present invention will be described, but the present invention is not limited to these examples. Additions, omissions, substitutions, and other modifications can be made without departing from the spirit of the present invention. Hereinafter, the present invention will be described in more detail.

≪Plant resistance induction control agent≫
The plant resistance induction controlling agent of the present invention contains a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

R ¹ and R ² are each independently substituted for any hydrogen atom (H) of X ¹ , X ² , X ³ , X ⁴ and X ⁵ which is CH.
R ⁴ each independently substitutes a hydrogen atom (H) of any one of X ⁶ , X ⁷ , X ⁸ , X ⁹ and X ¹⁰ that is CH.
The halogen atom of R ¹ is an element belonging to Group 17 in the periodic table such as F, Cl, Br, and I.
The linear or branched haloalkyl group having 1 to 4 carbon atoms of R ¹ is an alkyl group in which at least one hydrogen atom is substituted with a halogen atom independently selected. The halogen atom is the same as the above halogen atom. Examples of the linear or branched alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group. Group, sec-butyl group and tert-butyl group. Examples of the haloalkyl group having 1 to 4 carbon atoms include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a chloroethyl group, and a trifluoromethyl group is preferable.

The linear or branched alkyl group having 1 to 4 carbon atoms of R ^{2 is the same as} the linear or branched alkyl group having 1 to 4 carbon atoms described for the haloalkyl group of R ^1. is there. The linear or branched alkyl group having 1 to 4 carbon atoms of R ² preferably has 1 to 3 carbon atoms, and more preferably 1 or 2 carbon atoms.
The linear or branched alkenyl group having 1 to 4 carbon atoms of R ² preferably has 2 to 3 carbon atoms. Examples of the alkenyl group include ethenyl group (vinyl group) and 2-propenyl group (allyl group).

The linear or branched alkyl group having 1 to 4 carbon atoms for R ³ and R ⁴ is the same as the alkyl group described for the haloalkyl group for R ¹ .
The linear or branched alkenyl group having 2 to 4 carbon atoms in R ³ and R ⁴ is the same as the alkenyl group in R ² .
The halogen atom of R ⁴ is an element belonging to Group 17 in the periodic table such as F, Cl, Br, I, etc., and F is preferable.

In the formula (1), as a preferable combination of R ¹ , R ² , R ³ , R ⁴ ,
a combination in which n is 1, R ¹ is a haloalkyl group, m is 0, R ³ is a hydrogen atom, and p is 0,
a combination in which n is 1, R ¹ is a haloalkyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a halogen atom,
a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, and p is 0,
a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a halogen atom,
Examples include a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a fluorine atom.

The compound represented by the general formula (1) may be a salt, and the salt is preferably an agriculturally acceptable salt. For example, when any one of X ¹ to X ⁵ is N and the remaining is CH, the compound represented by the general formula (1) is a compound having a pyridine ring. In that case, examples of the salt include those in which the pyridine reacts with an acid to form a salt. The salt is preferably water-soluble.

In the compound represented by the general formula (1), when X ² to X ⁵ are CH, a compound represented by the following general formula (1-1) is exemplified.

[Wherein, X ¹ , X ⁶ , X ⁷ , X ⁸ , X ⁹ , X ¹⁰ , R ¹ , R ² , R ³ , R ⁴ , n, m and p are the same as those in the general formula (1)] The same. ]

In the compound represented by the general formula (1), when X ² to X ⁶ and X ⁸ to X ¹⁰ are CH, a compound represented by the following general formula (1-2) is exemplified.

[Wherein, X ¹ , X ⁷ , R ¹ , R ² , R ³ , R ⁴ , n, m and p are the same as those in the general formula (1). ]

The compound represented by the general formula (1) includes compounds represented by the following general formulas (2-1) to (2-3).

[Wherein, X ¹ , X ⁷ , R ¹ , R ² , R ³ , R ⁴ , m and p are the same as those in the general formula (1). ]

When X ¹ and X ⁷ are CH, examples of the compound represented by the general formula (1-2) include compounds represented by the following general formula (3-1).
When X ¹ is N and X ⁷ is CH, examples of the compound represented by the general formula (1-2) include compounds represented by the following general formula (3-2).
When X ¹ is CH and X ⁷ is N, examples of the compound represented by the general formula (1-2) include compounds represented by the following general formula (3-3).
When X ¹ and X ⁷ are N, examples of the compound represented by the general formula (1-2) include compounds represented by the following general formula (3-4).

[Wherein R ¹ , R ² , R ³ , R ⁴ , n, m and p are the same as those in the general formula (1). ]

In the compound represented by the general formula (3-2), as a preferable combination of R ¹ , R ² , R ³ and R ⁴ ,
a combination in which n is 1, R ¹ is a haloalkyl group, m is 0, R ³ is a hydrogen atom, and p is 0,
a combination in which n is 1, R ¹ is a haloalkyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a halogen atom,
a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, and p is 0,
a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a halogen atom,
Examples include a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a fluorine atom.

Examples of the compound represented by the general formula (3-2) include compounds represented by the following general formulas (3-2-1) to (3-2-3).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , m and p are the same as those in the general formula (1). ]

In the compound represented by the general formula (3-4), as a preferable combination of R ¹ , R ² , R ³ , and R ⁴ ,
a combination in which n is 1, R ¹ is a haloalkyl group, m is 0, R ³ is a hydrogen atom, and p is 0,
a combination in which n is 1, R ¹ is a haloalkyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a halogen atom,
a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, and p is 0,
a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a halogen atom,
Examples include a combination in which n is 1, R ¹ is a trifluoromethyl group, m is 0, R ³ is a hydrogen atom, p is 1 and R ⁴ is a fluorine atom.

Examples of the compound represented by the general formula (3-4) include compounds represented by the following general formulas (3-4-1) to (3-4-3).

Specific examples of the compound represented by the general formula (1) or a salt thereof include the following compounds or salts thereof. Their chemical structures are shown below. In addition, the compound represented by the said General formula (1) is not limited to the following examples.

N- (pyridin-2-yl) benzenesulfonamide (compound of formula 1-1-1),
N- (pyridin-2-yl) -4-methylpyridine-2-sulfonamide (compound of formula 1-1-2),
N- (5-isopropylpyridin-2-yl) -4-chlorobenzenesulfonamide (compound of formula 1-1-3),
N- (5-chloropyridin-2-yl) pyridine-3-sulfonamide (compound of formula 1-1-4),
N- (2-chloro-3-methylpyridin-6-yl) benzenesulfonamide (compound of formula 1-1-5),
N- (4-chloropyridin-2-yl) benzenesulfonamide (compound of formula 1-1-6),
N- (5-trifluoromethylpyridin-2-yl) benzenesulfonamide (compound of formula 1-1-7),
N-methyl-N- (5-trifluoromethylpyridin-2-yl) -4-methylbenzenesulfonamide (compound of formula 1-1-8),
N- (6-trifluoromethylpyridin-2-yl) pyridine-3-sulfonamide (compound of formula 1-1-9),
N- (6-trifluoromethylpyridin-2-yl) -2-fluorobenzenesulfonamide (compound of formula 1-1-10),
N- (6-cyanopyridin-2-yl) benzenesulfonamide (compound of formula 1-1-11),
N- (3-cyano-2-isopropylpyridin-6-yl) benzenesulfonamide (compound of formula 1-1-12),
N- (4-cyanopyridin-2-yl) pyridine-4-sulfonamide (compound of formula 1-1-13),
N- (6-nitropyridin-2-yl) -3-methylbenzenesulfonamide (compound of formula 1-1-14),
N- (5-nitropyridin-2-yl) pyridine-3-sulfonamide (compound of formula 1-1-15), and
N- (4-nitropyridin-2-yl) -N-vinylbenzenesulfonamide (compound of formula 1-1-16).

Specific examples of the compound represented by the general formula (1) or a salt thereof listed above include, in particular, N- (5-trifluoromethylpyridin-2-yl) benzenesulfonamide (formula 1-1 7), N- (6-trifluoromethylpyridin-2-yl) pyridine-3-sulfonamide (compound of formula 1-1-9), or N- (6-trifluoromethylpyridin-2-yl) ) -2-Fluorobenzenesulfonamide (compound of formula 1-1-10) or a salt thereof is preferred.
One embodiment of the present invention is selected from the group consisting of the compounds represented by the general formulas (1-1-7), (1-1-9), and (1-1-10) and salts thereof A plant resistance induction controlling agent containing any one or more as an active ingredient can be mentioned.
As one aspect of the present invention, a plant resistance induction regulator comprising as an active ingredient any one or more selected from the group consisting of the compound represented by the general formula (1-1-7) and salts thereof Is mentioned.
As one aspect of the present invention, a plant resistance induction regulator comprising as an active ingredient any one or more selected from the group consisting of the compound represented by the general formula (1-1-9) and salts thereof Is mentioned.
As one aspect of the present invention, a plant resistance induction regulator comprising as an active ingredient any one or more selected from the group consisting of the compound represented by the general formula (1-1-10) and salts thereof Is mentioned.

The compound represented by the general formula (1) may have a tautomer or a geometric isomer depending on the type of substituent. In the present specification, the compound represented by the general formula (1) may be described in only one form of an isomer, but the active ingredient of the present invention includes other isomers, and isomers. Or a mixture thereof.
In addition, the compound represented by the general formula (1) may have an asymmetric carbon atom or axial asymmetry, and an optical isomer based on this may exist. The active ingredient of the present invention includes those obtained by separating optical isomers of the compound represented by the general formula (1) or a mixture thereof.

The salt of the compound of the general formula (1) is preferably an agriculturally acceptable salt of the compound of the general formula (1), and forms an acid addition salt or a salt with a base depending on the type of substituent. There is a case. Specifically, inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid Acid addition with organic acids such as lactic acid, malic acid, mandelic acid, tartaric acid, dibenzoyltartaric acid, ditoluoyltartaric acid, citric acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, aspartic acid, glutamic acid Salts, salts with inorganic bases such as sodium, potassium, magnesium, calcium and aluminum, salts with organic bases such as methylamine, ethylamine, ethanolamine, lysine and ornithine, salts of various amino acids and amino acid derivatives such as acetylleucine, ammonium salts, etc. Hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, etc. Inorganic acids, formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, lactic acid, malic acid, mandelic acid, tartaric acid, dibenzoyltartaric acid, ditoluoyltartaric acid, citric acid, methanesulfonic acid, ethane Acid addition salts with organic acids such as sulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, aspartic acid and glutamic acid are preferred.

Furthermore, the active ingredient of the present invention includes various hydrates and solvates of the compound of the above general formula (1) and salts thereof, and crystalline polymorphic substances. The active ingredient of the present invention also includes compounds labeled with various radioactive or non-radioactive isotopes.

In the present invention, commercially available compounds and salts thereof can be used as the compound of the general formula (1) and salts thereof. Moreover, the compound of the said General formula (1) and its salt can be manufactured by applying the various well-known synthesis methods using the characteristics based on the basic structure or the kind of substituent. At that time, depending on the type of the functional group, it may be effective in terms of production technology to replace the functional group with an appropriate protecting group well known to those skilled in the art at the stage from the raw material to the intermediate.
Hereinafter, although the typical manufacturing method of the compound of the said General formula (1) is demonstrated, the manufacturing method of the active ingredient of this invention is not limited to the example shown below.
The compound of the general formula (1) can be produced as a free compound, a salt thereof, a hydrate, a solvate, or a crystalline polymorphic substance. The salt of the compound of the general formula (1) can also be produced by subjecting it to a salt formation reaction well known to those skilled in the art. Isolation and purification of the compound of the general formula (1) are performed by applying ordinary chemical operations such as extraction, fractional crystallization, various fractional chromatography and the like.

(First manufacturing method)

(The symbol in the formula represents the same meaning as described above. X in the formula (A1) represents a halogen atom, preferably chloro or bromo, more preferably chloro.)

This production method is a method for producing the compound represented by the general formula (1) by sulfonylamidation of the sulfonyl halide compound (A1) and the amine compound (A2).
For the sulfonylamidation, a method well known to those skilled in the art can be used. For example, the compound (A1) and the compound (A2) are used in an equivalent amount or in an excess amount, and a mixture of these is used in the presence of a condensing agent or a base. The reaction is carried out in a solvent inert to the reaction under cooling to heating, preferably at −20 ° C. to 60 ° C., usually for 0.1 hour to 5 days with stirring. Examples of the solvent used here are not particularly limited, but include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane and chloroform, diethyl ether and tetrahydrofuran. Ethers such as dioxane and dimethoxyethane, aprotic polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone, esters such as ethyl acetate and butyl acetate, acetonitrile, propionitrile and the like Nitriles or water, and mixtures thereof. Examples of the condensing agent include, but are not limited to, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide, dicyclohexylcarbodiimide, 1,1′-carbonyldiimidazole, diphenylphosphoric acid amide, phosphorus oxychloride and the like. It is not something. Use of an additive (for example, 1-hydroxybenzotriazole) may be effective for smoothly proceeding the reaction. Examples of the base include organic bases such as triethylamine, N, N-diisopropylethylamine, N-methylmorpholine and pyridine, or inorganic bases such as potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, potassium t-butoxide and sodium ethoxide. Although a base can be used, it is not limited to these.

(Second manufacturing method)

(The symbols in the formula represent the same meaning as described above. Lv represents a leaving group, preferably halogen, alkylsulfonyloxy, arylsulfonyloxy, more preferably fluoro, chloro, bromo, methane. Sulfonyloxy, ethanesulfonyloxy, benzenesulfonyloxy, trifluorobenzenesulfonyloxy.)

This production method is a method for producing the compound represented by the general formula (1) from the sulfonamide compound (B1) and the aryl compound (B2).
Preferably, the compound represented by the general formula (1) is produced by subjecting to an ipso substitution reaction. For the ipso substitution reaction, a method well known to those skilled in the art can be used. For example, the compound (B1) and the compound (B2) are used in an equivalent amount or in excess, and a mixture of these is used as an inert solvent for the reaction. The reaction is performed in the middle or without a solvent, under cooling to heating, preferably at 0 ° C. to 80 ° C., usually for 0.1 hour to 5 days. Examples of the solvent used here are not particularly limited, but include aromatic hydrocarbons, halogenated hydrocarbons, ethers, aprotic polar solvents, esters, nitriles, and mixtures thereof. It is done. Performing the reaction in the presence of an organic base or an inorganic base may be effective for smoothly progressing the reaction.

Moreover, it can replace with an ipso substitution reaction and can also manufacture the compound represented by the said General formula (1) by the coupling reaction using a transition metal. The coupling reaction can be performed by a method well known to those skilled in the art. Examples of the transition metal include tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium, palladium chloride-1-1'-bis (diphenylphosphine). A palladium catalyst such as fino) ferrocene is preferably used. At this time, an inorganic base is preferably used together.

(Raw material synthesis)
The sulfonyl halide compound (A1) can be produced by subjecting the corresponding sulfonic acid compound to a method well known to those skilled in the art, for example, a halogenation reaction. The sulfonic acid compound can be produced by subjecting the corresponding amino compound to a method well known to those skilled in the art, for example, a Sandmeyer reaction. The amino compound can be produced by subjecting the corresponding nitro compound to a method well known to those skilled in the art, for example, a reduction reaction.
For the sulfonamide compound (B1) in which R3 is not a hydrogen atom, the sulfonamide compound (B1) in which R3 is a hydrogen atom is subjected to methods well known to those skilled in the art, such as N-alkylation and N-alkenylation reactions. Can be manufactured. The sulfonamide compound (B1) in which R3 is a hydrogen atom is obtained by subjecting the halogenated sulfonyl compound (A1) to a method well known to those skilled in the art, for example, a sulfonamidation reaction with ammonia or a protected amine. Can be manufactured. When it is produced by a sulfonamidation reaction with a protected amine, a protecting group is eliminated as necessary.
The sulfonamide compound (B1) in which R3 is not a hydrogen atom is produced by a sulfonamidation reaction between a halogenated sulfonyl compound (A1) and a primary amine having an R3 group or a secondary amine having an R3 group and a protecting group. You can also When it is produced by a sulfonamidation reaction between the R3 group and a secondary amine having a protective group, the protective group is removed as necessary.

The compound of the general formula (1) is described in the literature (H. Nakayama et al., “Synthesis of N- (Trifluoromethyl-2-pyridinyl) arenesulfonamides as an Inhibitor of Secretory Phospholipase A ₂ ” Chemical and Pharmaceutical Bulletin (2011) Vol. 59 No. 6, p783-786.) And literature (T. Gelbrich et al., “Structural systematics of 4,4'-disubstituted benzenesulfonamidobenzenes. 1. Overview and dimer-based isostructures” Acta Crystallographica Section B (2007). Vol. 63, Part 4, p621-632.).

The plant resistance induction control in the present invention and the present specification includes inducing, enhancing, promoting, and maintaining plant disease resistance or pest resistance.
Since the plant resistance induction control agent of the present invention controls the induction of disease resistance, it can also be provided as a plant disease control agent.
Since the plant resistance induction control agent of the present invention controls the induction of pest resistance, it can also be provided as a pest control agent.

Inducing, strengthening and promoting plant disease resistance or insect pest resistance is a comparison between a plant treated with the plant resistance induction control agent of the present invention and an untreated plant. This means that in the plant treated with the plant resistance induction controlling agent of the invention, the expression of plant resistance or pest resistance is significantly improved.
Maintaining disease resistance or pest resistance of a plant means that a plant treated with the plant resistance induction control agent of the present invention is compared with an untreated plant, and the plant resistance induction control agent of the present invention is compared. It means that the expression of plant resistance or pest resistance is significantly prolonged for a long time in the treated plant.

The expression of disease resistance in plants can be determined by, for example, the following indicators, as shown in Examples described later.
[1] Using the expression of a gene specifically induced in the JA response pathway as an index, the plant treated with the plant resistance induction regulator of the present invention is compared with the untreated plant. In the plant treated with the plant resistance induction control agent, the expression of the disease resistance can be judged when the expression of the gene is significantly improved.
[2] Using the degree of the state of plant disease as an index, a plant treated with the plant resistance induction control agent of the present invention is compared with an untreated plant. In the treated plant, when the disease state of the plant disease is significantly improved, the expression of disease resistance can be determined.

The expression of insect pest resistance in a plant can be determined by, for example, the following index, as shown in Examples described later.
[3] Using the expression of a gene specifically induced in the JA response pathway as an index, the plant treated with the plant resistance induction regulator of the present invention is compared with the untreated plant. In the plant treated with the plant resistance induction regulator, the expression of pest resistance can be determined when the expression of the gene is significantly improved.
“4” The plant resistance of the present invention is compared by comparing the plant treated with the plant resistance induction control agent of the present invention with an untreated plant using the degree of feeding damage of the plant as an index. In the plant treated with the induction control agent, when the state of feeding damage of the plant body is improved, the expression of pest resistance can be determined.
"5" Using a plant habitat state of a pest or the like in an area treated with a plant resistance induction control agent as an index, comparing a plant treated with the plant resistance induction control agent of the present invention with an untreated plant In the plant treated with the plant resistance induction control agent of the present invention, the expression of pest resistance can be determined when the number of living organisms such as pests in the treatment area of the plant resistance induction control agent is low.

The control of plant diseases in the present invention and the specification of the present application refers to the inactivation effect on the fungus causing plant disease, the effect of preventing the infection of fungus causing plant disease, and the growth of the fungus causing plant disease. Includes suppression or prevention effects.
The pest control in the present invention and the specification of the present application includes an effect of depleting pests, an effect of killing pests, and an effect of repelling pests.

The type of plant to be used for the plant resistance induction control agent of the present invention is not particularly limited as long as it is a plant that can acquire resistance by inducing the ISR system, and even a land plant is an aquatic plant It may be. As land plants, angiosperms and gymnosperms are suitable, and they may be herbs or woods. As angiosperms, Rosaceae, Citrus, Grapeaceae, Orchidaceae, Orchidaceae, Lilyaceae, Leguminosae, Rubiaceae, Euphorbiaceae, Cyperaceae, Ceramaceae, Perillaceae, Cucurbitaceae, Eggplant, And Brassicaceae are more preferred, and solanaceae, Cucurbitaceae and Brassicaceae are more preferred.

An example of the lily family plant is onion. An example of the leguminous plant is soybean. An example of the celery family plant is carrot. Examples of the grass family include rice, corn, wheat and wheat. Examples of the cucurbitaceae plant include melon, watermelon, winter melon, cucumber, and pumpkin. Examples of the solanaceous plant include tobacco, tomato, potato, eggplant and bell pepper. Examples of the Brassicaceae plants include, for example, Nazuna, Brassica, Cabbage, Kale, Chinese cabbage, turnip, Japanese radish, Wasabi and mustard.
Preferable plants to be used for the plant resistance induction controlling agent of the present invention include tomato, tobacco, cucumber, tuna and rape.

The plant resistance induction controlling agent of the present invention may be provided in the form of a powder, tablet, granule, fine granule or the like by mixing with an agriculturally acceptable carrier, a bulking agent or the like, if necessary. Alternatively, it can be mixed with agriculturally acceptable solvents, surfactants, emulsifiers, dispersants and the like to form dosage forms such as emulsions, solutions, suspensions, wettable powders, water solvents, oils and the like.

The solvent for dissolving the plant resistance induction control agent may be appropriately selected according to the plant resistance induction control agent or the kind of the plant, but a sulfoxide compound such as dimethyl sulfoxide (DMSO); N, N-dimethylformamide (DMF) ), Amide compounds such as N, N-dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), and the like, and preferred are hydrophilic solvents.

The plant resistance induction control agent of the present invention may be provided in a dosage form that is used in combination with other agricultural and horticultural agents.
For example, the plant resistance induction control agent of the present invention and other JA type resistance induction control agents such as bestatin, hexanoic acid, arachidonic acid, N-acylamide and the like are provided in a dosage form such as a combination or a combination preparation. May be.
Moreover, for example, the plant resistance induction control agent of the present invention and a known SAR resistance induction control agent may be provided in a dosage form such as a combination or a combined preparation.

The pathogen to be protected by the use of the plant resistance induction regulator of the present invention is not particularly limited, but is preferably a pathogen that causes induction of the ISR system or can be protected by induction of the ISR system. Alternatively, a pathogen that causes induction of the ISR system and can be protected by induction of the ISR system is preferable. From such a viewpoint, it is more preferable that the pathogen to be protected by the plant resistance induction controlling agent of the present invention is a rot-causing pathogen. As rot-causing pathogens, gray mold fungus (Botrytis cinerea), potato anthracnose fungus (Colletotrichum atramentarium), cucumber anthracnose fungus (Colletotrichum lagenarium), tomato blight fungus (Phytophthora infestans), wheat rot fungus (Gaeumannomyces graminis) Soft rot fungus (Erwinia carotovora), black spot fungus (Diplocarpon rosae), rot fungus (Valsa ceratosperma), blight fungus (Cryphonectria parasitica), ergot fungus (Claviceps purpurea), pear black spot fungus (Alternaria alternata), brown rot fungus ella (Mycos pinodes), rice sesame leaf blight fungus (Cochliobolus miyabeanus), spot blight fungus (Stemphylium lycopersici), mycorrhizal fungus (Sclerotinia sclerotiorum), monilinia fungus (Monilinia sp.), leaf fungus fungus (Passalora fulva) Fusarium oxysporum f. Sp. Cucumerinum), Fusarium oxysporum, Raffaelea quercivora, green mold Penicillium digitatum), blue mold fungus (Penicillium italicum), citrus canker (Xanthomonas campestris pv. Citri), can be exemplified pathogens such as Ralstonia solanacearum (Ralstonia solanacearum). Among them, Alternaria alternata bacterium belonging to the genus Alternaria and Botrytis cinerea bacterium belonging to the genus Botrytis can be exemplified as typical humic pathogens.
Among them, as pathogens to be protected by the use of the plant resistance induction regulator of the present invention, fungi of the genus Alternaria which are rot pathogens, Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa, Botrytis allii, etc. Examples of the genus Botrytis are: Among them, Alternaria alternata belonging to the genus Alternaria, Botrytis cinerea bacteria belonging to the Botrytis genus can be exemplified as suitable use targets, and tomato gray mold fungus (Botrytis cinerea) or cucumber gray mold fungus (Botrytis cinerea) can be exemplified as particularly suitable use targets. .
The humic pathogenic bacteria include humic pathogenic bacteria that become conditionally humic depending on the surrounding environment.

Organisms such as pests to be controlled by the use of the plant resistance induction control agent of the present invention are not particularly limited. As described above, the ISR system induces a defense response against “injuries” such as food damage by pests. Therefore, the plant resistance induction control agent of the present invention can be applied to a wide variety of organisms such as insects and mites that feed on plants as a control agent.
Examples of organisms such as pests to be controlled by the use of the plant resistance induction regulator of the present invention include Coleoptera pests such as Azuki beetle (Callosobruchus chinensis), scales such as Plutella xylostella and Pieris rapae Pests of the eye, Musca domestica, Dacus cucurbitae, etc., Nezara antennata, Hemiptera, Frankliniella occidentalis, etc. ), Etc., cockroach insects such as Blattella germanica, various insect pests such as nematodes such as Dermatophagoides farinae, nematodes such as sweet potato nematode (Meloidogyne incognita). Forest pests include Coleoptera, Ptertypus quercivorus and other pests, Tomicus piniperda, and other species, Mochamus alternatus (Mochamus alternatus) Examples thereof include pests of the genus Mochamus to which M. saltuaris and the like belong.
In Examples to be described later, the plant resistance induction control agent according to the present invention was found to have a controlling effect against the blue pear (Plutella xylostella) and the peach aphid (Myzus persicae). Is preferably applied to pests belonging to the order Lepidoptera typified by goldfish, and more preferably applied to pests of the family Plutellidae. Further, in the examples described later, since the plant resistance induction control agent according to the present invention was found to have a controlling effect against the peach aphid (Myzus persicae), It is preferably applied to pests belonging to the hemiptera represented by aphids, and more preferably applied to pests of the aphid superfamily (Aphidoidea).

The present invention provides a plant resistance induction control method in which the compound represented by the general formula (1) or a salt thereof is brought into contact with a plant to be applied.
In one embodiment, the present invention provides a compound represented by the above general formula (1) or a salt thereof for controlling plant resistance induction.
In one embodiment, the present invention provides use of a compound represented by the above general formula (1) or a salt thereof for controlling plant resistance induction.
In one embodiment, the present invention provides use of a compound represented by the above general formula (1) or a salt thereof for producing a plant resistance induction controlling agent.

The plant resistance induction control agent can induce resistance by bringing an effective amount into contact with a plant to be applied.
The method of bringing the effective amount of the plant resistance induction controlling agent into contact with the plant may be the same as in the case of the known induction agent, and the treatment method applied to the plant, the soil where the plant is cultivated, or the hydroponic solution where the plant is cultivated. Can be mentioned. Treatment methods include, for example, a method in which a plant resistance induction control agent is sprayed on soil in which plants are grown, a method of mixing with soil, a method of soil irrigation, and a plant resistance induction in which a plant resistance induction control agent is dissolved. Examples thereof include a method of applying or spraying a control agent solution to a plant, a method of growing a plant in the plant resistance induction control agent solution, and a method of mixing a plant resistance induction control agent into a hydroponic solution.

In the plant resistance induction control method of the present invention, the site of the plant body to be treated or administered with the plant resistance induction control agent is not particularly limited. For example, all the leaves, stems, and roots of the plant body may be sprayed, or only some leaves, some stems, and some roots may be sprayed. Even when the whole plant body is not sprayed, the secondary metabolite produced in the sprayed site reaches the necessary site of the plant body, and resistance to pests can be obtained even in the site where the plant body is not sprayed. Resistance to pests can also be obtained by infiltrating the plant body from the root system by soil treatment, immersion treatment, or the like.

The usage-amount of a plant resistance induction | guidance | derivation control agent can be suitably adjusted according to an induction control agent and the kind of plant. In the case of treating the soil with a method of spraying, mixing or irrigating the induction control agent, for example, the amount of the active ingredient used per time is 1 to 20 kg / 10a, 1 to 10 kg / 10a, 1 to 1.3 kg / 10a, and can be used once a year or multiple times as needed during the period from the time the plants germinate until they are harvested. When used multiple times, it is preferable to use it 2 to 6 times a year and 1 to 3 times a month.
Moreover, when processing with the method of apply | coating or spraying the said induction control agent solution to the foliage of a plant, the density | concentration of the compound or its salt represented by the said General formula (1) contained in an induction control agent solution is 0.1. ˜500 μM, 1 to 500 μM, 1 to 300 μM, 1 to 100 μM are preferable, and 10 to 50 μM are more preferable. For example, the use amount of the induction control agent solution having a concentration of 0.1 to 500 μM or 1 to 500 μM per time is set to 1 to 1000 μL per leaf, and during the period from the germination of the plant to the harvest, Can be used once or multiple times as needed. When used multiple times, it is preferable to use it 2 to 6 times a year and 1 to 3 times a month.
The concentration of the compound represented by the general formula (1) or a salt thereof contained in the induction control agent solution in the case of treating with a method of growing a plant in the induction control agent solution such as hydroponics is 0.1. -500 μM are preferred, 1-500 μM are preferred, 1-300 μM are more preferred, 1-100 μM are more preferred, and 10-50 μM are particularly preferred. For example, the amount of the induction control agent solution having a concentration of 0.1 to 500 μM or 1 to 500 μM used per time is 1 to 1000 μL per plant body, and during the period from when the plant germinates until it is harvested, Can be used once a year or multiple times as needed. When used multiple times, it is preferable to use it 2 to 6 times a year and 1 to 3 times a month.

The timing of use of the resistance induction control agent of the present invention can be used at any time of planting, sowing, transplanting, or planting. Moreover, it can be applied at any stage of growth of seeds, seedlings, juveniles, and mature individuals.
In the case of tomato, for example, it is applied 1 to 3 times after 20 days after germination to 14 days before harvest.
In the case of cucumber, for example, it is applied 1 to 3 times after 20 days after germination to 14 days before harvest.
In the case of cabbage, for example, it is applied 1 to 3 times from 20 days after germination to 14 days before harvest.

The plant resistance induction controlling agent of the present invention may be used in combination with other agricultural and horticultural agents. The plant resistance induction controlling agent and other agricultural and horticultural agents may be used simultaneously or separately.
For example, the plant resistance induction control agent of the present invention may be used in combination with other JA resistance induction control agents such as bestatin, hexanoic acid, arachidonic acid, N-acylamide and the like.
Further, for example, the plant resistance induction control agent of the present invention and a known SAR resistance induction control agent may be used in combination.

The plant resistance induction control agent may be brought into contact with the plant body after the occurrence of pests or the onset of plant diseases. Further, the plant resistance induction controlling agent may be used prophylactically, and the plant resistance induction controlling agent may be brought into contact with the plant body before occurrence of pests or plant diseases.

The resistance induction control agent of the present invention can induce good resistance by treating the active ingredient at a low concentration as compared with the conventional JA resistance induction control agent.

≪Plant growth promoter≫
The plant resistance induction control agent of the present invention can also be used as a plant growth promoter.
It is known that SAR response and plant hatching are closely related, and that biomass is reduced under SAR response induction. As will be shown in Examples described later, the plant growth promoter according to the present invention has inhibitory control activity on the expression of SAR defense response gene. Therefore, according to the plant growth promoting agent of the present invention, a plant growth promoting effect can be obtained. Examples of the plant growth promoter include those similar to those described in the plant resistance induction control agent, and thus the description thereof is omitted.

The plant growth promoter of the present invention may be provided in a dosage form that is used in combination with other agricultural and horticultural agents.
For example, it may be provided in a dosage form such as a mixture or a combination preparation of the plant growth promoter of the present invention and other known compounds having a plant growth promoting effect.

The plant growth promoter of the present invention may be used in combination with other agricultural and horticultural agents. The plant growth promoter and other agricultural and horticultural agents may be used simultaneously or separately.
For example, you may use together the plant growth promoter of this invention, and the compound which has another well-known plant growth promotion effect.

The plant growth promoter of the present invention has a plant growth promoting effect. The expression of the plant growth promoting effect in the plant can be determined by, for example, the following index as shown in the examples described later.
[1] In a plant treated with the plant growth promoter of the present invention, the plant growth promoter of the present invention is compared with a plant treated with the plant growth promoter of the present invention using the growth rate of the plant as an index. When the growth rate of the plant body is significantly increased, the expression of the plant growth promoting effect can be determined.
“2” The plant growth promoter of the present invention is treated by comparing the plant treated with the plant growth promoter of the present invention with the untreated plant using the biomass of the plant at a specific time as an index. In the case of the plant, when the biomass of the plant body at a specific time is significantly increased, the expression of the plant growth promoting effect can be determined.

In one embodiment, the present invention provides a method for promoting plant growth comprising contacting a plant growth promoter with a plant. Since the method which can illustrate the method similar to what was demonstrated in the method of contacting a plant resistance induction | guidance | derivation control agent with a plant can be illustrated, description is abbreviate | omitted.

In one embodiment, the present invention provides a compound represented by the above general formula (1) or a salt thereof for promoting plant growth.
In one embodiment, the present invention provides use of a compound represented by the above general formula (1) or a salt thereof for promoting plant growth.
In one embodiment, the present invention provides use of a compound represented by the above general formula (1) or a salt thereof for producing a plant growth promoter.

<Microbial infection efficiency promoter / transgene expression efficiency promoter>
The plant resistance induction regulator of the present invention can also be used as a microbial infection efficiency promoter or a transgene expression efficiency promoter.
The plant resistance induction controlling agent of the present invention suppresses the expression of SAR defense response and promotes artificial microbial infection efficiency to plants. As shown in the Examples described later, the microbial infection efficiency promoting agent according to the present invention has an effect of promoting gene transfer expression by the agroinfiltration method. Therefore, according to the microbial infection efficiency promoter of the present invention, the effect of promoting microbial infection efficiency to plants can be obtained. According to the microbial infection efficiency promoter of the present invention, for example, promotion of plant transformation efficiency by Agrobacterium and promotion of gene expression after transformation are achieved. In this case, the plant resistance induction regulator of the present invention can also be used as a transformation promoter, a gene transfer promoter, and a transgene expression efficiency promoter.
Examples of the microbial infection efficiency promoter include those similar to those described in the plant resistance induction control agent, and thus the description thereof is omitted. Examples of the transgene expression efficiency promoter include those similar to those described in the plant resistance induction control agent, and thus the description thereof is omitted. Examples of the target microorganism include Agrobacterium and various plant viruses that infect plants. The gene to be introduced is not particularly limited as long as it can be introduced by the microorganism.

The microorganism infection efficiency promoter of the present invention may be provided in a dosage form that is used in combination with other agricultural and horticultural agents.
For example, it may be provided in a dosage form such as a mixture or a combination preparation of the microbial infection efficiency promoter of the present invention and other known compounds having an effect of promoting microbial infection efficiency.
For example, the transgene expression efficiency promoter of the present invention and other known transgene expression efficiency promoting effects may be provided in a dosage form such as a combination or a combined preparation.

The microbial infection efficiency promoter of the present invention may be used in combination with an agricultural and horticultural agent. The microbial infection efficiency promoter and other agricultural and horticultural agents may be used simultaneously or separately.
For example, the plant growth promoter of the present invention may be used in combination with other known compounds having an effect of promoting the efficiency of microbial infection.
For example, the transgene expression efficiency promoting agent of the present invention may be used in combination with other known compounds having a transgene expression efficiency promoting effect.

The microbial infection efficiency promoter of the present invention has an effect of promoting microbial infection efficiency. The expression of the effect of promoting microbial infection efficiency in plants can be determined by, for example, the following indicators, as shown in the examples described later.
“1” A plant having been treated with the microorganism infection efficiency promoter of the present invention using the expression level of a gene introduced into the plant by the microorganism as an index by infecting the plant body with a microorganism having transformation ability, When the expression level of the gene is significantly increased in the plant treated with the microbial infection efficiency promoting agent of the present invention, compared with a non-plant, the expression of the microbial infection efficiency promoting effect can be determined.

The transgene expression efficiency promoter of the present invention has an effect of promoting transgene expression efficiency. The expression of the effect of promoting transgene expression efficiency in plants can be determined by, for example, the following indicators, as shown in the Examples described later.
“1” A plant having been treated with the microorganism infection efficiency promoter of the present invention using the expression level of a gene introduced into the plant by the microorganism as an index by infecting the plant body with a microorganism having transformation ability, When the expression level of the gene is significantly increased in the plant treated with the microbial infection efficiency promoting agent of the present invention, compared with a non-plant, the expression of the microbial infection efficiency promoting effect can be determined.

In one embodiment, the present invention provides a method for promoting microbial infection comprising contacting a plant with a microbial infection efficiency promoter. Since the method which can illustrate the method similar to what was demonstrated in the method of contacting a plant resistance induction | guidance | derivation control agent with a plant can be illustrated, description is abbreviate | omitted.

In one embodiment, the present invention provides a compound represented by the above general formula (1) or a salt thereof for promoting microbial infection efficiency.
In one embodiment, the present invention provides use of a compound represented by the above general formula (1) or a salt thereof for promoting microbial infection efficiency.
In one embodiment, the present invention provides the use of a compound represented by the above general formula (1) or a salt thereof for producing a microbial infection efficiency promoter.

In one embodiment, the present invention provides a method for promoting transgene expression efficiency, which comprises contacting a plant with a transgene expression efficiency promoter.
As one embodiment of the method for promoting the efficiency of transgene expression according to the present invention, the method for promoting the efficiency of transgene expression comprising introducing a gene into a plant by a microorganism and bringing the plant resistance induction regulator of the present invention into contact with the plant Is mentioned.
As one embodiment of the method for promoting transgene expression efficiency according to the present invention, the method comprises introducing a gene into a plant by a microorganism, bringing the plant resistance induction regulator of the present invention into contact with the plant, and expressing the gene. Examples include a method for promoting transgene expression efficiency.
The introduction of a gene into a plant by a microorganism may be performed after the transgene expression efficiency promoter of the present invention is brought into contact with the plant, or may be performed simultaneously.
Since the method of bringing the transgene expression efficiency promoter of the present invention into contact with a plant can be exemplified by the same method as described in the method of bringing a plant resistance induction regulator into contact with a plant, description thereof is omitted. A method for introducing a gene into a plant by a microorganism can be performed by a known method such as an agroinfiltration method. The target plant into which the gene is introduced is used to include plant cells, tissues, cell masses, callus, and plant individuals.

In one embodiment, the present invention provides a compound represented by the above general formula (1) or a salt thereof for promoting transgene expression efficiency.
In one embodiment, the present invention provides use of a compound represented by the above general formula (1) or a salt thereof for promoting transgene expression efficiency.
In one embodiment, the present invention provides the use of a compound represented by the above general formula (1) or a salt thereof for producing a transgene expression efficiency promoter.

Next, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples.

<Selection of compounds that induce VSP1 gene expression>
First, according to the results shown in the literature (Utsugi et al. (1998) Plant Mol Biol 38: 565-576; Guerineau et al. (2003) J Exp Bot 54: 1153-1162), by PCR, Arabidopsis thaliana ( The promoter sequence of VSP1 gene was amplified from genomic DNA of Arabidopsis thaliana ecotype Columbia. The promoter sequence of the VSP1 gene was ligated upstream of Fluc of a plasmid (pBI221-Fluc) having a gene sequence of a reporter gene (firefly luciferase gene (FLuc)) to obtain a pBI121-VSP1 :: Fluc plasmid. The plasmid was introduced into Arabidopsis thaliana through Agrobacterium tumefaciens LBA4404 to obtain transformed Arabidopsis VSP1 :: Fluc having VSP1 :: Fluc. The transformed Arabidopsis seeds were sown in a multiwell plate and germinated in a luciferin aqueous solution.
Prepare a dimethyl sulfoxide (DMSO) solution of each compound in a commercially available compound library, and add this solution to each well so that the concentration of the compound is 30 μM to treat the seedlings of transformed Arabidopsis thaliana did. Growth was performed under photoperiod conditions of 22 ° C., 12 hours dark period / 12 hours light period (70 μmolm ⁻² S ⁻¹ ).

By using a photocounting device (ARGUS system, manufactured by Hamamatsu Photonics) and software (AQUACOSMOS, manufactured by Hamamatsu Photonics), measuring the luminescence intensity in each well and measuring the expression level of the reporter Fluc, The VSP1 gene expression inducing activity of each compound was evaluated.

As a result, treatment of the compound represented by the formula (1-1-7), treatment of the compound represented by (1-1-9), and treatment of the compound represented by (1-1-10) Thus, it was revealed that expression of Fluc protein was induced in the transformed Arabidopsis VSP1 :: Fluc. The compound represented by the formula (1-1-7) is hereinafter referred to as “Compound X”.

In transformed Arabidopsis VSP1 :: Fluc, it was confirmed that the luminescence intensity of the Fluc protein started to increase after several hours of treatment with Compound X. Thereafter, after 144 hours of treatment with Compound X, the luminescence intensity of Fluc protein in transformed Arabidopsis VSP1 :: Fluc reached about 90 (number of photons / min / μm ² ). When Compound X was not treated, no luminescence of Fluc protein was detected in transformed Arabidopsis VSP1 :: Fluc. From this, it was suggested that Compound X has VSP1 gene expression inducing activity in Arabidopsis seedlings.

<Evaluation of the effect of Compound X on Fluc gene expression>
Next, the effect of compound X on Fluc gene expression inducing activity was confirmed using transformed Arabidopsis thaliana having 35S :: Fluc (n = 16). Arabidopsis thaliana 35S :: Fluc was performed in the same manner as the production of VSP1 :: Fluc.

The luminescence intensity of Fluc protein was measured by treatment with Compound X on Arabidopsis thaliana 35S :: Fluc (compound X group). As a control, a group treated with DMSO alone instead of the DMSO solution of each compound X (DMSO group), and a group treated with a DMSO solution of MeJA instead of the DMSO solution of each compound X (MeJA group) But the luminescence intensity of Fluc protein was measured. As a result of the measurement, the luminescence intensity values of the Fluc protein in the compound X group, DMSO group, and MeJA group were almost the same value (the luminescence intensity was about 3000 (number of photons / minute / μm ² ) after 120 hours of treatment). It was. From this, it was confirmed that Compound X does not affect Fluc gene expression activity. From these results, it was confirmed that compound X exhibits a clear VSP1 gene expression inducing activity by acting on the VSP1 gene promoter.
Furthermore, RNA was extracted from 5-week-old wild-type Arabidopsis thaliana induced as described above, and endogenous VSP1 gene expression was quantified using the RT-PCR method. As clearly as with Fluc. Induction of endogenous VSP1 gene expression by compound X treatment was confirmed.

From the above results, it was shown that Compound X induces the expression of VSP1 gene. The expression of VSP1 gene is specifically induced in the JA response pathway. Therefore, it was confirmed that the resistance was induced by the ISR system that is known to be induced through JA by treating the compound X with plants.

<Evaluation of the effect of Compound X in 3 weeks old Arabidopsis thaliana>
In the selection experiment, the resistance induction of Arabidopsis seedlings was evaluated. A similar experiment was performed on an Arabidopsis thaliana 3-week-old individual (n = 24).
A DMSO solution of Compound X was prepared, and this solution was added to each well so that the concentration of Compound X was 30 μM, and the transformed Arabidopsis thaliana was treated (Compound X group). Instead, the group treated with DMSO alone (DMSO group) was evaluated. Furthermore, in addition to the compound X group and the DMSO group, the group treated with the DMSO solution of MeJA instead of the DMSO solution of the compound X (MeJA group) was also evaluated.

In the transformed Arabidopsis VSP1 :: Fluc of the compound X group and the MeJA group, it was confirmed that the luminescence intensity of the Fluc protein started to increase immediately after each compound treatment. 72 hours after the treatment, the value of the luminescence intensity of the Fluc protein in the transformed Arabidopsis VSP1 :: Fluc of the compound X group and the MeJA group was about 250 (number of photons / min / μm ² )). On the other hand, in Arabidopsis VSP1 :: Fluc in the DMSO group, no luminescence of Fluc protein was detected. From this, it was suggested that Compound X has VSP1 gene expression-inducing activity even in Arabidopsis thaliana 3-week-old individuals.
Further, when the resistance induction mode was compared between Compound X and MeJA, it was found that the resistance induction effect of Compound X was exhibited from the same early point as MeJA. And the resistance inducing action of Compound X lasted longer than that of MeJA. From this, it can be seen that Compound X has a very excellent resistance-inducing action having both immediate effect and sustainability.

<Inhibitory effect of compound X on SAR defense response gene expression>
The effect of Compound X on the SAR system was evaluated using transformed Arabidopsis PR-1a :: Fluc. PR-1a is a gene specifically induced in the SA response pathway (Tanaka T, Ono S, Watakabe Y, Hiratsuka K (2006), Bioluminescence reporter assay system to monitor Arabidopsis MPK3 gene expression in response to infection by Botrytis cinerea. J. Gen. Plant Pathol. 72, 1-5).
Evaluation was performed on the seedlings of Arabidopsis PR-1a :: Fluc (n = 8). A DMSO solution was added to each well so that the concentration of Compound X, SA or MeJA was 30 μM, and the transition of luminescence activity was observed (FIG. 5). In contrast to DMSO, clear expression induction was observed with SA alone, but with MeJA or Compound X treatment, suppression of expression induction by SA was observed, and the suppression activity was more effective with compound X being sustained. It was suggested that This shows that Compound X has an inhibitory control activity on the expression of SAR defense response gene.

<Evaluation of antibacterial activity of Compound X>
In order to confirm the antibacterial activity of Compound X itself, evaluation by the inhibition circle method was performed. Here we investigated the antibacterial activity against anthrax and gray mold. Anthracnose fungi are representative of active parasitic fungi, and gray mold fungus is representative of saprophytic fungi.
100 μl (1.0 × 10 ⁵ spores / ml) of anthrax anthracnose (C. higginsianum) was applied to PDA medium, and further treated with 10 μl (100 mM) of Compound X solution. Hygromycin 10 μl (100 mM) was used as a positive control, and DMSO was used as a negative control. This was cultured in the dark at 24 ° C. for 10 days.
100 μl (3.0 × 10 ⁵ spores / ml) of B. cinerea spores were applied to the PSA medium, and further treated with 10 μl of Compound X solution (100 mM). Hygromycin 10 μl (100 mM) was used for positive subjects and DMSO was used for negative subjects. This was cultured at 24 ° C. for 5 days.
As a result of the test, it was clarified that Compound X does not exhibit antibacterial activity against anthrax and gray mold even at a high concentration treatment of 100 mM. Compounds that do not have antibacterial activity are less likely to produce drug-resistant bacteria. Therefore, the compound X according to the plant resistance induction controlling agent of the present invention is excellent in that it is difficult to produce drug-resistant bacteria and can be used for a long time.

≪Evaluation of plant resistance induction of compound X≫
<Test 1>
[Comparative Example 1]
To mature Arabidopsis thaliana (Col-0) (Fig. 1 (a)) 37 days after sowing, add DMSO aqueous solution (approximately 0.03%) to the soil and let the DMSO aqueous solution absorb from the roots. Gave. 72 hours later, mature Arabidopsis thaliana individuals were inoculated by spray with sterile water containing gray mold prepared at a spore concentration of 5 × 10 ⁴ spores / ml, 22 ° C., 12 hours dark period / 12 hours light period ( 70 μmolm ⁻² S ⁻¹ ). FIG. 1 (b) is a photograph of the plant 3 days after inoculation. As shown in FIG.1 (b), many lesions were seen on the leaf of the plant body.
[Example 1]
Instead of DMSO aqueous solution (approx. 0.03%), the compound X aqueous solution prepared using DMSO aqueous solution (approx. Were tested in the same manner as in Comparative Example 1. (FIG. 1 (c)) is a mature Arabidopsis thaliana plant (Col-0) 37 days after sowing. FIG. 1 (d) is a photograph of the plant 3 days after inoculation. Compared with the plant body of Comparative Example 1 (FIG. 1B), it can be seen that the occurrence of lesions is suppressed in the plant body of Example 1 (FIG. 1D).
From the above results, it is clear that in Arabidopsis matured individuals, Compound X exhibits an infiltration inhibitory effect on gray mold and a high control effect on gray mold.

<Test 2>
[Comparative Example 2]
A mature tomato individual 46 days after germination was immersed in a 150 mL DMSO aqueous solution (about 0.03%) per strain. 72 hours later, mature tomato individuals were spot-inoculated with 5 μL of gray mold fungus prepared at a spore concentration of 1 × 10 ⁵ spores / ml and grown at 22 ° C. Light 16h. FIG. 2 (a) is a photograph of leaves obtained from a plant 5 days after inoculation. It can be seen that lesions are found on the leaves and the growth of the leaves is poor.
[Example 2]
Compared with DMSO aqueous solution (about 3%), soaked compound X aqueous solution prepared using DMSO aqueous solution (about 3%) to contain compound X instead of DMSO aqueous solution (about 0.03%). Tested as in Example 2. FIG. 2 (b) is a photograph of the plant 5 days after inoculation. Compared with the plant body of Comparative Example 2 (FIG. 2 (a)), the plant body of Example 2 (FIG. 2 (b)) has a reduced area of lesions and good leaf growth. I understand.

The graph of FIG. 2 (c) quantifies the results obtained in <Test 2>. The vertical axis of the graph is the value of the result of measuring the maximum lesion diameter in each inoculated leaf at 5 days after seeding of gray mold.
As is clear from the graph of FIG. 2 (c), it can be seen that the area of the lesion was reduced in the individual given Compound X. From this, it was confirmed that Compound X has a high control effect against gray mold fungus in mature tomato plants.

<Test 3>
[Comparative Example 3]
A cucumber mature individual 46 days after germination was immersed in a 150 mL DMSO aqueous solution (about 0.03%) per strain. 72 hours later, 5 μL of gray mold fungus prepared to a spore concentration of 1 × 10 ⁵ spores / ml was spot-inoculated to mature cucumber individuals and grown at 22 ° C. in Light 16h. FIG. 3 (a) is a photograph of leaves obtained from a plant 5 days after inoculation. It can be seen that lesions are found on the leaves and the growth of the leaves is poor.
[Example 3]
Compared with DMSO aqueous solution (about 3%) prepared by using DMSO aqueous solution (about 3%) so that it contains Compound X at 30 μM instead of DMSO aqueous solution (about 0.03%) Tested as in Example 3. FIG. 3 (b) is a photograph of the plant 5 days after inoculation. Compared with the plant body of Comparative Example 3 (FIG. 3A), the plant body of Example 3 (FIG. 3B) has a small lesion area and good leaf growth. I understand.

The graph of FIG.3 (c) quantifies the result obtained by <Test 3>. The vertical axis of the graph is a measurement of the maximum diameter of lesions occurring on the plant body at 5 days after seeding of the gray mold fungus.
As is apparent from the graph of FIG. 3C, it can be seen that the lesion area was suppressed to be small in the individual given Compound X. From this, it was confirmed that Compound X has a high control effect against gray mold fungus in mature cucumber individuals.

<Test 4>
[Comparative Example 4] Untreated group The peach aphid (Myzus persicae) was released to the mature cabbage individuals after 85 days after sowing. The number of peach aphids was counted 2 days, 6 days, 9 days, 15 days, and 22 days after Compound X spraying.
[Example 4]
The surface of the plant body is sprayed on a compound X aqueous solution prepared by diluting 30 mM DMSO solvent 1000 times with well water and adding the spreading agent mylino to 5000 times so that compound X is contained at 30 μM. The test was conducted in the same manner as in Comparative Example 4 except that a sufficient amount was sprayed so as to be sufficiently wet and given to mature cabbage individuals. The investigation in <Test 4> was commissioned to the Japan Plant Protection Association.

The results of Test 4 are shown in Table 1. The numerical value of Example 4 in Table 1 is expressed as a corrected density index based on the value obtained in Comparative Example 4. From the results shown in Table 1, it was clarified that in this test, Compound X exhibits a controlling effect against peach aphid until 9 days after the application of Compound X.

<Test 5>
[Comparative Example 5]
In Comparative Example 4, the test was conducted in the same manner as in Comparative Example 4 except that the test was started after inoculating 100 eggs per strain 2 days after spraying Compound X instead of Peachella xylostella instead of the peach aphid. went. The total number of young moth larvae of young larvae, middle larvae and old larvae 9 days, 15 days and 22 days after release was counted.
[Example 5]
Instead of DMSO aqueous solution (about 3%), Compound X aqueous solution prepared using DMSO aqueous solution (about 3%) so as to contain Compound X at 30 μM is sprayed on the whole plant by spraying to give mature cabbage individuals. The test was performed in the same manner as in Comparative Example 5 except that. The investigation of <Test 5> was commissioned to the Japan Plant Protection Association.

The results of Test 5 are shown in Table 2. From the results shown in Table 2, it was clarified that in this test, Compound X exerts a remarkable and long-lasting control effect on the diamondback moth.

<Evaluation of growth promotion effect by compound X treatment>
It is known that SAR response and plant hatching are closely related, and that biomass is reduced under SAR response induction. Then, the influence on the growth of the plant body by the process of the compound X which shows SAR inhibitory activity was evaluated.
The evaluation was performed on cabbage (variety: gold type 201). The cabbage growth conditions were as follows: sowing: 128-well cell tray, cabbage seedling raising period: 1 ward, 64 strains not connected (2 block survey), planting: 29 days after sowing, after planting: 1 ward, 14 strains, 2 continuity.
Compound X powder was dissolved in DMSO to 15 mM and diluted 1000 times the predetermined concentration using well water (spraying concentration was 15 μM). Further, a spreading agent Mylino was added so as to be 5000 times to prepare a compound X diluted drug solution for spraying.
As the first chemical spraying, the compound X diluted chemical was sprayed on cabbage (three cabbage leaves) 21 days after sowing. As a second chemical spray, compound X diluted chemical was sprayed on cabbage (34 cabbage leaves) 28 days after sowing. As a third chemical spray, compound X diluted chemical was sprayed on cabbage (45 cabbage leaves) 35 days after sowing. A sufficient amount of the diluted chemical solution was sprayed using a back sprayer so that the front and back of the leaves were wet. Thereafter, observation (photographing) was performed 57 days after sowing.

The observation results are shown in FIG. When the growth status of the plant body was compared between the group treated with compound X (compound X-treated group) and the group not treated with compound X (compound X-untreated group), A clear growth promoting effect was observed compared to the X untreated section.

<Microbial infection efficiency improvement effect by compound X treatment>
A DMSO solution of Compound X containing Compound X at final concentrations of 1 μM, 5 μM, and 10 μM was prepared. In addition, a DMJA solution of MeJA was prepared instead of the DMSO solution of Compound X. Tobacco (Nicotiana tabacum SR1 strain) was seeded in the well, and each adjusted liquid was added to each well, and tobacco was germinated and grown under continuous light at 22 ° C. (N = 24 (each concentration group)). Agrobacterium LBA4404 strain having an intron-inserted luciferase gene (inserted between CaMV35S promoter and HSP terminator) was treated and infected by an ordinary method on seedlings 11 days after sowing. The luciferase activity was continuously monitored up to 144 hours after Agrobacterium infection by luminescence observation with a high sensitivity camera. The results of monitoring are shown in FIG. The vertical axis of the graph shown in FIG. 7 is an average value of relative activities 48 to 120 hours after infection. A clear increase in gene expression was confirmed in all treatment groups of Compound X at final concentrations of 1 μM, 5 μM, and 10 μM. In particular, a clear increase in expression was observed even when treated with a relatively low concentration (1 μM) of Compound X.

The present invention can be used in the entire field of plant cultivation.

Claims

A plant resistance induction controlling agent comprising a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 each independently represent CH or N (provided that X 1 , X 2 , Any two or more of X 3 , X 4 and X 5 are not N, and any two or more of X 6 , X 7 , X 8 , X 9 and X 10 are not N).
R 1 represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R 2 represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R 3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R 4 represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R 1 and is 0 or 1. m represents the number of R 2 and is an integer of 0 to 5, and when m is 2 or more, R 2 may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R 4 and is an integer of 0 to 5, and when p is 2 or more, R 4 may be the same or different from each other. ]
The plant resistance induction controlling agent according to claim 1, wherein the general formula (1) is a compound represented by the following general formula (1-2).

[In the formula (1-2), X 1 , X 7 , R 1 , R 2 , R 3 , R 4 , n, m and p have the same meaning as described above. ]
The plant resistance induction controlling agent according to claim 2, wherein the general formula (1) is a compound represented by the following general formula (3-2-2).

[In the formula (3-2-2), R 1 , R 2 , R 3 , R 4 , n, m and p have the same meaning as described above. ]
A plant resistance induction control method comprising bringing a plant resistance induction control agent according to any one of claims 1 to 3 into contact with a plant.
A plant disease control method comprising using the plant resistance induction control method according to claim 4.
A method for controlling pests comprising using the plant resistance induction control method according to claim 4.
A plant growth promoter comprising a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 each independently represent CH or N (provided that X 1 , X 2 , Any two or more of X 3 , X 4 and X 5 are not N, and any two or more of X 6 , X 7 , X 8 , X 9 and X 10 are not N).
R 1 represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R 2 represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R 3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R 4 represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R 1 and is 0 or 1. m represents the number of R 2 and is an integer of 0 to 5, and when m is 2 or more, R 2 may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R 4 and is an integer of 0 to 5, and when p is 2 or more, R 4 may be the same or different from each other. ]
A microorganism infection efficiency promoter containing a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 each independently represent CH or N (provided that X 1 , X 2 , Any two or more of X 3 , X 4 and X 5 are not N, and any two or more of X 6 , X 7 , X 8 , X 9 and X 10 are not N).
R 1 represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R 2 represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R 3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R 4 represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R 1 and is 0 or 1. m represents the number of R 2 and is an integer of 0 to 5, and when m is 2 or more, R 2 may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R 4 and is an integer of 0 to 5, and when p is 2 or more, R 4 may be the same or different from each other. ]
A transgene expression efficiency promoter containing a compound represented by the following general formula (1) or a salt thereof as an active ingredient.

[In Formula (1),
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 each independently represent CH or N (provided that X 1 , X 2 , Any two or more of X 3 , X 4 and X 5 are not N, and any two or more of X 6 , X 7 , X 8 , X 9 and X 10 are not N).
R 1 represents a linear or branched haloalkyl group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group,
R 2 represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched alkenyl group having 2 to 4 carbon atoms.
R 3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkenyl group having 2 to 4 carbon atoms,
R 4 represents a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkenyl group having 2 to 4 carbon atoms, or a halogen atom.
n represents the number of R 1 and is 0 or 1. m represents the number of R 2 and is an integer of 0 to 5, and when m is 2 or more, R 2 may be the same or different from each other. However, n + m is an integer of 5 or less. p represents the number of R 4 and is an integer of 0 to 5, and when p is 2 or more, R 4 may be the same or different from each other. ]