JP5747382B2 - Plant resistance inducer - Google Patents

Description

  The present invention relates to a drug that induces plant resistance.

  Plants have acquired physical and chemical resistance mechanisms in the course of evolution against attack by external pathogens. The physical resistance mechanism is, for example, a coating such as a wax layer or a cuticle layer, or a cell wall, and serves as a pathogen barrier. On the other hand, the chemical resistance mechanism is a system that inhibits the growth of pathogenic bacteria, and includes, for example, resistance factors that are congenitally accumulated in plants and resistance factors that are inductively biosynthesized and accumulated. It is done.

  In recent years, in order to protect plants from disease stress, attempts have been made to improve the tolerance of plants by administering chemicals from the outside to activate chemical resistance mechanisms. Such drugs can be called resistance inducers, and various inducers have been studied so far. For example, it has been clarified that treatment of tobacco with salicylic acid or acetylsalicylic acid induces resistance to tobacco mosaic virus (TMV) (see Non-Patent Document 1). On the other hand, in 1974, 3-allyloxy-1,2-beisoisothiazole-1,1-dioxide was first registered in the world as an agrochemical as an inducer. The inducers reported so far are all monocyclic or bicyclic heterocyclic compounds except salicylic acid and derivatives thereof, and most of them are nitrogen atoms and sulfur as heteroatoms in the heterocyclic skeleton. It contains atoms (see Non-Patent Document 2).

R. F. White, Virology, 99, 410 (1979) Yoshihiro Narusaka, Kazuyuki Hiratsuka, Yoshiteru Noto, “Activation of plant immunity by plant activator and application to chemical genetics”, Chemistry and Biology, Vol. 48, no. 10, 2010

The growth of plants that are resistant to disease stress can be an effective solution to various problems that are likely to become serious in the future, such as food shortages, environmental destruction, and biodiversity destruction. Development of is strongly desired.
This invention is made | formed in view of the said situation, and makes it a subject to provide the resistance inducer for plants of a novel chemical structure.

To solve the above problem,
The present invention provides a plant resistance inducer comprising a compound represented by the following general formula (1) as an active ingredient.

（式中、Ｘ^１は下記一般式（１ａ）又は（１ｂ）で表される基であり；Ｘ^２及びＸ^３はそれぞれ独立にカルボニル基又は下記一般式（１ｃ）で表される基であり；Ｚは水素原子以外の一価の基であり；Ｒ^１は水素原子又は置換基を有していてもよい炭化水素基であり；ｍは０〜４の整数であり、ｍが２〜４である場合、複数のＺは互いに同一でも異なっていてもよい。）

Wherein X ¹ is a group represented by the following general formula (1a) or (1b); X ² and X ³ are each independently a carbonyl group or a group represented by the following general formula (1c) Z is a monovalent group other than a hydrogen atom; R ¹ is a hydrogen atom or a hydrocarbon group which may have a substituent; m is an integer of 0 to 4, and m is 2 to 4 And the plurality of Z may be the same or different from each other.)

（式中、Ｒ^２は置換基を有していてもよい炭化水素基であり；Ｙ^１は芳香族基である。）

(In the formula, R ² is a hydrocarbon group which may have a substituent; Y ¹ is an aromatic group.)

  In the plant resistance inducer of the present invention, the compound represented by the general formula (1) is preferably represented by the following general formula (1) -1A or (1) -2A.

（式中、Ｒ^２ａは置換基を有していてもよいアリール基又は環状のアルキル基であり；Ｒ^１０は炭素数１〜１５のアルキル基又は炭素数６〜１５のアリール基であり；Ｇはハロゲン原子であり；ｎ_１は１〜５の整数であり；ｎ_２は０〜５の整数であり、ｎ_２が２〜５である場合、複数のＧは互いに同一でも異なっていてもよい。）

(In the formula, R ^2a is an ^optionally substituted aryl group or a cyclic alkyl group; R ¹⁰ is an alkyl group having 1 to 15 carbon atoms or an aryl group having 6 to 15 carbon atoms; G Is a halogen atom; n ₁ is an integer of ₁ to 5; n ₂ is an integer of 0 to 5, and when n ₂ is ₂ to 5, a plurality of G may be the same or different from each other .)

  According to the present invention, it is possible to provide a plant resistance inducer having a novel chemical structure.

It is a graph which shows the measurement result of the emitted light intensity in Examples 1-3, the reference example 1, and the comparative example 1. FIG.

Hereinafter, the present invention will be described in detail. In the present specification, the unit “M” refers to “mol / L”.
The plant resistance inducer of the present invention (hereinafter abbreviated as “inducing agent”) is a compound represented by the following general formula (1) (hereinafter abbreviated as “compound (1)”) as an active ingredient. To do.

（式中、Ｘ^１は下記一般式（１ａ）又は（１ｂ）で表される基であり；Ｘ^２及びＸ^３はそれぞれ独立にカルボニル基又は下記一般式（１ｃ）で表される基であり；Ｚは水素原子以外の一価の基であり；Ｒ^１は水素原子又は置換基を有していてもよい炭化水素基であり；ｍは０〜４の整数であり、ｍが２〜４である場合、複数のＺは互いに同一でも異なっていてもよい。）

Wherein X ¹ is a group represented by the following general formula (1a) or (1b); X ² and X ³ are each independently a carbonyl group or a group represented by the following general formula (1c) Z is a monovalent group other than a hydrogen atom; R ¹ is a hydrogen atom or a hydrocarbon group which may have a substituent; m is an integer of 0 to 4, and m is 2 to 4 And the plurality of Z may be the same or different from each other.)

（式中、Ｒ^２は置換基を有していてもよい炭化水素基であり；Ｙ^１は芳香族基である。）

(In the formula, R ² is a hydrocarbon group which may have a substituent; Y ¹ is an aromatic group.)

In General Formula (1), X ¹ is a group represented by General Formula (1a) or (1b). Two bond coupling destination in the general formula (1a) and (1b) is not identified, corresponding to two of the bonds extending from X ¹ of the general formula (1).
In General Formulas (1a) and (1b), R ² is a hydrocarbon group that may have a substituent.
The hydrocarbon group for R ² may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.

The saturated aliphatic hydrocarbon group (alkyl group) for R ² may be linear, branched or cyclic. And it is preferable that it is C1-C30, and it is more preferable that it is 1-15.
Examples of the linear or branched alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, and n-pentyl group. , Isopentyl group, neopentyl group, tert-pentyl group, 1-methylbutyl group, n-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, n-heptyl group, 2-methylhexyl group, 3-methylhexyl group, 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3-dimethylpentyl group, 3 -Ethylpentyl group, 2,2,3-trimethylbutyl group, n-octyl group, isooctyl group, nonyl group, decyl group, undecyl group, dodecyl group Tridecyl group, tetradecyl group, a pentadecyl group can be exemplified.
The cyclic alkyl group may be monocyclic or polycyclic, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, norbornyl group, isobornyl group, Examples thereof include an adamantyl group and a tricyclodecyl group.

In the unsaturated aliphatic hydrocarbon group of R ² , one or more single bonds (C—C) between carbon atoms in the alkyl group are double bonds (C═C) and / or triple bonds (C≡ The group substituted by C) can be illustrated, and the number and position of these unsaturated bonds (double bonds and triple bonds) are not particularly limited. Examples of those having one unsaturated bond include alkenyl groups such as ethenyl group (vinyl group) and 2-propenyl group (allyl group); alkynyl groups such as ethynyl group and 2-propynyl group (propargyl group).

The aromatic hydrocarbon group (aryl group) for R ² may be monocyclic or polycyclic, and preferably has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms. Of these, preferable examples include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
When the hydrocarbon group in R ² is cyclic, for example, one hydrogen atom from a structure in which a cyclic aliphatic hydrocarbon (cycloalkane, cycloalkene, etc.) and an aromatic hydrocarbon (arene) are condensed. It may be a monovalent group from which is removed.

The hydrocarbon group for R ² may have a substituent. Here, "R ² has a substituent", one or more hydrogen atoms constituting R ² is either substituted with a group other than a hydrogen atom, or one or more carbon atoms constituting R ² Is substituted with a group other than a carbon atom. And both the hydrogen atom and the carbon atom may be substituted with a substituent.

Examples of substituents for substituting hydrogen atoms include alkyl groups, alkoxy groups, alkylcarbonyl groups, alkyloxycarbonyl groups, alkylcarbonyloxy groups, alkenyl groups, alkenyloxy groups, aryl groups, aryloxy groups, alkylaryl groups, arylalkyls. Group, alkylaryloxy group, arylalkyloxy group, alkynyl group, hydroxyl group (—OH), carboxy group (—COOH), amino group (—NH ₂ ), nitro group (—NO ₂ ), cyano group (—CN) And a halogen atom.

The alkyl group substituting for a hydrogen atom is the same as the above alkyl group.
Examples of the alkoxy group that substitutes a hydrogen atom include monovalent groups in which the alkyl group is bonded to an oxygen atom, such as a methoxy group and a cyclopropoxy group.
Examples of the alkylcarbonyl group replacing a hydrogen atom include monovalent groups in which the alkyl group is bonded to a carbonyl group (—C (═O) —) such as a methylcarbonyl group or a cyclopropylcarbonyl group.
Examples of the alkyloxycarbonyl group that substitutes a hydrogen atom include monovalent groups in which the alkyl group is bonded to an oxycarbonyl group (—O—C (═O) —), such as a methoxycarbonyl group or a cyclopropoxycarbonyl group. .
Examples of the alkylcarbonyloxy group for substituting a hydrogen atom include a monovalent group in which the alkyl group is bonded to a carbonyloxy group (—C (═O) —O—) such as a methylcarbonyloxy group or a cyclopropylcarbonyloxy group. It can be illustrated.

The alkenyl group for substituting a hydrogen atom is the same as the alkenyl group.
Examples of the alkenyloxy group that substitutes a hydrogen atom include monovalent groups in which the alkenyl group is bonded to an oxygen atom, such as an ethenyloxy group and a 2-propenyloxy group.

The aryl group that substitutes a hydrogen atom is the same as the aryl group.
Examples of the aryloxy group that substitutes a hydrogen atom include monovalent groups in which the aryl group is bonded to an oxygen atom, such as a phenoxy group, a 1-naphthoxy group, and a 2-naphthoxy group.
Examples of the alkylaryl group that substitutes a hydrogen atom include a monovalent group in which one hydrogen atom bonded to a carbon atom constituting an aromatic ring in the aryl group is substituted with the alkyl group.
Examples of the arylalkyl group that substitutes a hydrogen atom include monovalent groups in which one hydrogen atom is substituted with the aryl group in the alkyl group.
As the alkylaryloxy group for substituting a hydrogen atom, the alkyl group and the oxygen atom are bonded to the arylene group obtained by removing one hydrogen atom bonded to the carbon atom constituting the aromatic ring from the aryl group. Examples of such monovalent groups.
Examples of the arylalkyloxy group for substituting a hydrogen atom include a monovalent group in which the aryl group and an oxygen atom are bonded to an alkylene group obtained by removing one hydrogen atom from the alkyl group.

The alkynyl group for substituting a hydrogen atom is the same as the alkynyl group.
Examples of the halogen atom that replaces the hydrogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The number of substituents replacing the hydrogen atom is not particularly limited, and may be one or two or more. When there are two or more, these substituents may all be the same, may all be different, or may be partially different. All hydrogen atoms may be substituted with a substituent.
The position of the hydrogen atom substituted with the substituent is not particularly limited.

As the substituent for substituting a carbon atom, a carbonyl group (—C (═O) —), a carbonyloxy group (—C (═O) —O—), an amide group (—NH—C (═O) —) And heteroatoms. When the substituent for substituting a carbon atom has an asymmetric structure, the direction at the substitution site is not particularly limited.
Examples of the hetero atom that substitutes a carbon atom include an oxygen atom, a nitrogen atom, a sulfur atom, and a boron atom.

The number of substituents substituting for carbon atoms is not particularly limited as long as it is less than the number of carbon atoms before substitution, and may be one or two or more. When there are two or more, these substituents may all be the same, may all be different, or may be partially different.
The position of the carbon atom substituted with the substituent is not particularly limited.

R ² preferably has an alkylene group as a bonding site to the nitrogen atom to which it is bonded, and the alkylene group preferably has 1 to 5 carbon atoms.
Preferable R ² is exemplified by a group represented by the following general formula (1d).

（式中、Ｒ^２ａは置換基を有していてもよいアリール基又は環状のアルキル基であり；ｎ_１は１〜５の整数である。）

(In the formula, R ^2a is an aryl group or a cyclic alkyl group which may have a substituent; n ₁ is an integer of ₁ to 5)

In general formula (1d), R ^2a is an aryl group or a cyclic alkyl group which may have a substituent. One bond whose general bond destination is not specified in the general formula (1d) corresponds to one bond extending from R ² in the general formulas (1a) and (1b).
The aryl group for R ^{2a is the same as} the aryl group for R ² , preferably having 6 to 15 carbon atoms, and more preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group.
The cyclic alkyl group for R ^{2a is the same as} the cyclic alkyl group for R ² , and preferably has 5 to 15 carbon atoms.

The aryl group and cyclic alkyl group of R ^2a may have a substituent. Here, "R ^2a has a substituent", one or more hydrogen atoms constituting R ^2a is either substituted with a group other than a hydrogen atom, or one or more carbon atoms constituting R ^2a Is substituted with a group other than a carbon atom. And both the hydrogen atom and the carbon atom may be substituted with a substituent.

The substituent which the aryl group of R ^2a and the cyclic alkyl group have is the same as the substituent which the hydrocarbon group of R ² has.
The number of substituents that replace the hydrogen atom of R ^2a is not particularly limited, and may be one or two or more. When there are two or more, these substituents may all be the same, may all be different, or may be partially different. All hydrogen atoms may be substituted with a substituent.
The position of the hydrogen atom substituted with the substituent is not particularly limited.
The number of substituents substituting the carbon atom of R ^2a is not particularly limited as long as it is less than the number of carbon atoms before substitution, and may be one or two or more. When there are two or more, these substituents may all be the same, may all be different, or may be partially different.
The position of the carbon atom substituted with the substituent is not particularly limited.

Preferred as the aryl group having a substituent of R ^2a are those in which one or more hydrogen atoms bonded to the carbon atom constituting the aromatic ring are substituted with an alkoxy group, Examples thereof include those in which one or more constituent carbon atoms are substituted with nitrogen atoms.
The alkoxy group that replaces the hydrogen atom of R ^{2a is the same as} the alkoxy group that replaces the hydrogen atom of R ² , and preferably has 1 to 5 carbon atoms. Furthermore, when there are a plurality of the alkoxy groups, the plurality of alkoxy groups may be bonded to each other to form a ring together with atoms that are bonded to each other and constitute an aromatic ring.

Preferred examples of the cyclic alkyl group having a substituent for R ^2a include those in which one or more carbon atoms constituting the ring are substituted with an oxygen atom. The number of substitution with oxygen atoms is preferably 1 to 3.

n ₁ (number of methylene groups) is an integer of 1 to 5, and preferably 1 to 3.

In General Formula (1), X ² and X ³ are each independently a carbonyl group (—C (═O) —) or a group represented by General Formula (1c). That is, X ² and X ³ may be the same as or different from each other. Two bonds whose general bond destination is not specified in the general formula (1c) correspond to two bonds extending from X ² or X ³ in the general formula (1).
In General Formula (1c), Y ¹ is an aromatic group, and examples thereof may include an aromatic hydrocarbon group and an aromatic heterocyclic group which may have a substituent.

The aromatic hydrocarbon group (aryl group) for Y ¹ is the same as the aryl group for R ² .

The aromatic heterocyclic group (heteroaryl group) of Y ¹ is one obtained by removing one hydrogen atom bonded to a constituent atom of an aromatic heterocyclic ring from an aromatic heterocyclic compound (heteroarene). A valent group can be exemplified. Here, the hetero atom in the aromatic heterocycle is the same as the hetero atom for substituting the carbon atom of R ² .
The aromatic heterocyclic compound may be monocyclic or polycyclic, and when it is polycyclic, for example, an aromatic hydrocarbon (arene) and an aromatic heterocyclic compound (heteroarene) are condensed. It may be a compound having a structure.

Specific examples of the aromatic heterocyclic compound include monocyclic five-membered ring compounds such as pyrrole, imidazole, pyrazole, furan, thiophene, oxazole, isoxazole, thiazole, isothiazole, and phosphole; pyridine, pyridazine, pyrimidine, and pyrazine. Monocyclic six-membered compounds such as triazine, benzofuran, isobenzofuran, indole, isoindole, benzothiophene, benzo (c) thiophene, benzimidazole, benzoxazole, benzisoxazole, purine, indazole, benzothiazole, quinoline, isoquinoline And polycyclic compounds such as quinoxaline, quinazoline, cinnoline and acridine.
Further, examples of the heteroaryl group include those in which one or more carbon atoms constituting the aromatic ring of the aryl group in R ² are substituted with a heteroatom other than those exemplified above.

“The aromatic hydrocarbon group and the aromatic heterocyclic group have a substituent” means that one or more hydrogen atoms constituting these groups are substituted with a group other than a hydrogen atom. The substituent for substituting the hydrogen atom is the same as the above-mentioned substituent in which the hydrogen atom is substituted in the hydrocarbon group of R ² , preferably a halogen atom, and more preferably a chlorine atom.
The number and position of the substituents in the aromatic hydrocarbon group and aromatic heterocyclic group of Y ¹ are not particularly limited.

Y ¹ is preferably an aryl group which may have a substituent, and more preferably an aryl group having 6 to 15 carbon atoms which may have a substituent.

In general formula (1), Z is a monovalent group other than a hydrogen atom, and m (the number of bonds of Z to the benzene ring skeleton) is an integer of 0 to 4. That is, in the tetracyclic skeleton in the compound (1), in the benzene ring skeleton, one or more hydrogen atoms may be substituted with a substituent.
Z is the same as the substituent for substituting the hydrogen atom of R ² , and is an alkyl group, alkoxy group, alkylcarbonyl group, alkyloxycarbonyl group, alkylcarbonyloxy group, alkenyl group, alkenyloxy group, aryl group, aryl Oxy group, alkylaryl group, arylalkyl group, alkylaryloxy group, arylalkyloxy group, alkynyl group, hydroxyl group (—OH), carboxy group (—COOH), amino group (—NH ₂ ), nitro group (—NO ₂ ), a cyano group (-CN), and a halogen atom.

When m is 2-4, several Z may mutually be same or different. That is, all Zs may be the same, all may be different, or only some may be different.
When m is 1 to 4, the bonding position of Z in the benzene ring skeleton is not particularly limited.
m is preferably from 0 to 3, and more preferably from 0 to 2.

In general formula (1), R ¹ is a hydrogen atom or a hydrocarbon group which may have a substituent.
The hydrocarbon group which may have a substituent for R ^{1 is the same as} the hydrocarbon group which may have a substituent for R ² .
R ¹ is preferably a hydrocarbon group which may have a substituent, more preferably a hydrocarbon group having 1 to 15 carbon atoms, and an alkyl group having 1 to 15 carbon atoms or 6 carbon atoms. Particularly preferred is an aryl group of ˜15.

  Compound (1) is represented by the following general formula (1) -1A or (1) -2A (hereinafter abbreviated as “compound (1) -1A” or “compound (1) -2A”, respectively)) Is preferred.

（式中、Ｒ^２ａは置換基を有していてもよいアリール基又は環状のアルキル基であり；Ｒ^１０は炭素数１〜１５のアルキル基又は炭素数６〜１５のアリール基であり；Ｇはハロゲン原子であり；ｎ_１は１〜５の整数であり；ｎ_２は０〜５の整数であり、ｎ_２が２〜５である場合、複数のＧは互いに同一でも異なっていてもよい。）

(In the formula, R ^2a is an ^optionally substituted aryl group or a cyclic alkyl group; R ¹⁰ is an alkyl group having 1 to 15 carbon atoms or an aryl group having 6 to 15 carbon atoms; G Is a halogen atom; n ₁ is an integer of ₁ to 5; n ₂ is an integer of 0 to 5, and when n ₂ is ₂ to 5, a plurality of G may be the same or different from each other .)

In the general formula (1) -1A and (1) ^{-2A, R 2a} is the same as ^{R 2a} in the formula (1d).
In General Formula (1) -1A, G is a halogen atom, which is the same as the halogen atom that substitutes the hydrogen atom of R ² , and is preferably a chlorine atom.
In General Formulas (1) -1A and (1) -2A, R ¹⁰ is an alkyl group having 1 to 15 carbon atoms or an aryl group having 6 to 15 carbon atoms, and an alkyl group having 1 to 15 carbon atoms in R ¹ or This is the same as the aryl group having 6 to 15 carbon atoms.

Formula (1) -1A and (1) -2A, _{n 1} is the same as _{n 1} in the general formula (1d).

In General Formula (1) -1A, n ₂ (the number of bonds of G to the benzene ring skeleton) is an integer of 0 to 5.
If n ₂ is 2 to 5, a plurality of G may be the same or different from each other. That is, all G may be the same, all may be different, or only a part may be different.
If n ₂ is 1-4, the bonding position of G on the benzene ring skeleton is not particularly limited.
n ₂ is preferably 0 to 3, and more preferably 0 to 2.

  Compound (1) is a tetracyclic compound containing a 7-azabicyclo [2,2,1] heptane skeleton or a 7-aza-8-oxabicyclo [2,2,2] octane skeleton. That is, according to the difference in the skeleton, the compound (1) has a 7-azabicyclo [2,2,1] heptane skeleton and is represented by the following general formula (1) -1 (hereinafter referred to as “compound (1)”. -1 ”) and a compound represented by the following general formula (1) -2 having a 7-aza-8-oxabicyclo [2,2,2] octane skeleton (hereinafter referred to as“ compound (1) ”) -2 ").

（式中、Ｒ^１、Ｒ^２、Ｘ^２、Ｘ^３、Ｚ及びｍは前記と同様である。）

(Wherein R ¹ , R ² , X ² , X ³ , Z and m are the same as above).

Conventional derivatives are all monocyclic or bicyclic heterocyclic compounds except salicylic acid and derivatives thereof, and most of them contain a nitrogen atom and a sulfur atom as heteroatoms in the heterocyclic skeleton.
On the other hand, the compound (1) is a tetracyclic compound as described above, and the hetero atom constituting the ring structure contains a nitrogen atom or a nitrogen atom and an oxygen atom. Have a novel skeleton that is quite different. In particular, it has a tricyclic skeleton in which a 7-azabicyclo [2,2,1] heptane skeleton or 7-aza-8-oxabicyclo [2,2,2] octane skeleton and a benzene ring skeleton are condensed. It is presumed that this is an advantageous element for the expression of activity.

Compound (1) can be produced, for example, by the following method.
Among the compounds (1), the compound (1) -1 is an isoindole represented by the following general formula (1) -1-1 (hereinafter abbreviated as “compound (1) -1-1”); And a nitrogen-containing unsaturated cyclic compound represented by the following general formula (1) -1-2 (hereinafter abbreviated as “compound (1) -1-2”). . Compound (1) -1-1 and compound (1) -1-2 may be reacted under the same conditions as in a normal Diels-Alder reaction. For example, a method of reacting in a halogenated hydrocarbon solvent such as methylene chloride, preferably at −10 to 10 ° C., preferably for 1 to 120 minutes, is not limited thereto. It is preferable that the usage-amount of "compound (1) -1-2" is 1-5 mol with respect to 1 mol of "compound (1) -1-1".

（式中、Ｒ^１、Ｒ^２、Ｘ^２、Ｘ^３、Ｚ及びｍは前記と同様である。）

(Wherein R ¹ , R ² , X ² , X ³ , Z and m are the same as above).

In compound (1) -1, when at least one of X ² and X ³ is a carbonyl group, a reduction reaction is performed to convert the carbonyl group (—C (═O) —) to the formula “—CH (—OH)”. A carboxylic acid represented by the general formula “Y ¹ —C (═O) —OH (wherein Y ¹ is as defined above)” or a halide thereof. The carbonyl group can be converted to the group represented by the general formula (1c) by performing a condensation reaction by reacting or reacting an ester of the carboxylic acid to perform an ester exchange reaction.

The reduction reaction of the carbonyl group may be performed by a known method. For example, a method in which a reducing agent such as sodium borohydride (NaBH ₄ ) is allowed to act in an alcohol solvent such as ethanol and the reaction is preferably performed at 10 to 40 ° C., preferably 5 to 60 hours, is limited thereto. Not. The amount of the reducing agent used may be appropriately adjusted according to the number of carbonyl groups to be reduced. When one carbonyl group in one molecule is reduced, 1 mol of “Compound (1) -1” is used. It is preferable that it is 1-6 mol.
Further, the reaction for converting the hydroxyl group generated by the reduction reaction to the group represented by the general formula (1c) may be performed under normal conditions. For example, in the case of carrying out the condensation reaction using the carboxylic acid halide, preferably in the presence of a weak base such as pyridine in a halogenated hydrocarbon solvent such as methylene chloride, preferably at −10 to 40 ° C. Although the method of making it react for 5 to 24 hours is mentioned, It is not limited to this. The amount of the carboxylic acid halide used may be appropriately adjusted according to the number of hydroxyl groups to be converted, but when one hydroxyl group in one molecule is converted to the group represented by the general formula (1c), It is preferable that it is 1-4 mol with respect to 1 mol of compounds which have a hydroxyl group.
When both X ² and X ³ are carbonyl groups, whether to convert either one of X ² and X ³ or both into the group represented by the general formula (1c) is: For example, it can be adjusted as appropriate by adjusting the reducing conditions such as the amount of the reducing agent used, the temperature of the reduction reaction, and the time of the reduction reaction.

On the other hand, compound (1) -2 is obtained by the manufacturing method which has the process of oxidizing compound (1) -1 among compounds (1).
The oxidation reaction of compound (1) -1 may be performed by a known method. For example, a peroxide such as m-chloroperbenzoic acid (mCPBA) is used as an oxidizing agent in a halogenated hydrocarbon solvent such as methylene chloride, preferably at −10 to 40 ° C., preferably 5 to 48. Although the method of making it react for time is mentioned, It is not limited to this. Although the usage-amount of an oxidizing agent is based also on the kind, it is preferable that it is 1-3 mol with respect to 1 mol of "compound (1) -1".
After the nitrogen in the 7-azabicyclo [2,2,1] heptane skeleton forms an N-oxide (N → O) by an oxidation reaction, a rearrangement reaction occurs, so that 7-aza-8-oxabicyclo [2 , 2, 2] octane skeleton is considered to be formed.

（式中、Ｒ^１、Ｒ^２、Ｘ^２、Ｘ^３、Ｚ及びｍは前記と同様である。）

(Wherein R ¹ , R ² , X ² , X ³ , Z and m are the same as above).

In the compound (1) -2, when at least one of X ² and X ³ is a carbonyl group, the carbonyl group is represented by the general formula (1c) in the same manner as in the compound (1) -1. Can be converted to the group represented.
In compound (1) -1, wherein at least one of X ² and X ³ is a carbonyl group, the carbonyl group is converted to a group represented by the general formula (1c) by the above method, and then an oxidation reaction is performed. Even when a 7-aza-8-oxabicyclo [2,2,2] octane skeleton is formed, the same compound (1) -2 is obtained.

Depending on the structure, compound (1) may be produced by appropriately performing other steps such as functional group protection and deprotection in the production method as necessary.
When the compound (1) is produced, after completion of the reaction in each step, post-treatment may be performed as necessary according to a conventional method, and the product may be taken out. That is, as needed, post-treatment operations such as filtration, washing, extraction, pH adjustment, dehydration, and concentration are performed alone or in combination of two or more to concentrate, crystallize, reprecipitate, column chromatography. For example, the product may be taken out. In addition, the extracted product may be further subjected to crystallization, reprecipitation, column chromatography, extraction, stirring and washing of the crystals with a solvent, etc., if necessary, or one or more times in combination of two or more. It may be purified by performing.
The structure of the compound (1) can be confirmed by a known method such as nuclear magnetic resonance (NMR), infrared spectroscopy (IR), mass spectrometry (MS) and the like.

  The inducer of the present invention may comprise compound (1) as an active ingredient and consist only of compound (1), or may contain other components in addition to compound (1). Other components are not particularly limited as long as they do not interfere with the effects of the present invention, and preferred examples thereof include a solvent described later.

The inducer of the present invention can induce resistance by contacting the plant to be applied.
The method of bringing the inducer into contact with the plant may be the same as in the case of a known inducer. For example, the method of spraying the inducer on the soil where the plant is growing, the solution of the inducer in which the inducer is dissolved is applied to the plant. Examples thereof include a method of applying or spraying and a method of growing plants in the inducer solution.

  The solvent for dissolving the inducer may be appropriately selected according to the type of the inducer and the plant, but sulfoxides such as dimethyl sulfoxide (DMSO); N, N-dimethylformamide (DMF), N, N-dimethylacetamide Hydrophilic solvents such as amides such as (DMAc) and N-methylpyrrolidone (NMP) are preferred.

  The usage-amount of the inducer of this invention may be the same as the usage-amount of a well-known inducer, and can be suitably adjusted according to the kind of inducer or a plant. For example, when the inducer is sprayed on the soil, the amount used per time is 1 to 1.3 kg / 10a, and can be used once and multiple times as necessary. Moreover, when apply | coating or spraying the said inducer solution to a plant, the usage-amount of the inducer solution with a density | concentration of 10-500 micromol shall be 1-1000 microliters per leaf, and once as needed. Can be used multiple times. When a plant is grown in the inducer solution, an inducer solution having a concentration of 1 to 50 μM can be used.

  The compound (1) in the inducer may be one kind or two or more kinds. In the case of two or more kinds, the combination and ratio may be appropriately adjusted according to the purpose.

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

<Production of Compound (1) -1>
[Production Example 1]
(Production of Compound (1) -101)

Piperonylamine (0.93 g, 6.2 mmol) is dissolved in acetonitrile (5 ml), and a solution of 2-chloromethylbenzaldehyde (0.46 g, 3 mmol) in acetonitrile (10 ml) is added dropwise at room temperature to the solution. And stirred at room temperature for 1 hour. Then, the reaction mixture was diluted with methylene chloride (10 ml) and then washed twice with water (10 ml) and once with saturated brine. The organic layer was dried over magnesium sulfate, and the solvent was distilled off with an evaporator to obtain crude piperonylisoindole.
Next, N-methylmaleimide (0.41 g, 3.6 mmol) was dissolved in methylene chloride (10 ml), and the crude piperonylisoindole obtained above was dissolved in methylene chloride (10 ml). The solution was added dropwise at 0 ° C. and stirred at 0 ° C. for 5 minutes. The solvent was distilled off with an evaporator, and the residue was purified by silica gel column chromatography (mobile phase: hexane / ethyl acetate (1/1, volume ratio)) to obtain white crystals of compound (1) -101 (yield) 0.83 g, yield 77%). By spectral analysis, it was confirmed that Compound (1) -101 was an endo isomer. Identification data for the compound (1) -101 are as follows.
mp: 155-158 ° C
IR (KBr): 3436, 3010, 2821, 2293, 1763, 1436, 1288, 1132, 768, 749cm ^-1
1 H NMR (270 MHz, CDCl ₃ ): δ 7.35-7.18 (m, 9H), 4.58 (d, J = 1.6 Hz, 1H), 4.57 (d, J = 1.6 Hz, 1H), 3.69 (d, J = 1.6 Hz, 1H), 3.68 (d, J = 1.6 Hz, 1H), 3.38 (s, 2H), 2.26 (s, 3H)

[Production Example 2]
(Production of Compound (1) -102)

Compound (1) -101 (1.082 g, 3.0 mmol) obtained above was dissolved in ethanol (20 ml), and sodium borohydride (NaBH ₄ ) (0.459 g, 12 mmol) was dissolved in the solution. A solution dissolved in ethanol (20 ml) was added dropwise at room temperature, and the mixture was stirred at room temperature for 40 hours. Next, the reaction mixture is adjusted to pH 5-6 using dilute hydrochloric acid aqueous solution (1N), diluted with methylene chloride (20 ml), washed with water (20 ml) and saturated aqueous sodium hydrogen carbonate solution, and the organic layer is washed with magnesium sulfate. And dried. Subsequently, the solvent was distilled off with an evaporator, and one carbonyl group of compound (1) -101 was reduced (“—C (═O) —” was converted to “—CH (—OH) —”). Compound (1) -102-1 was obtained as a crude product (yield 1.085 g, yield 98%). Identification data of the compound (1) -102-1 are as follows.
mp: 156-159 ° C
IR (KBr): 3400-3174, 2901, 1650, 1489, 1252, 1071, 1035, 760 cm ^-1
1 H NMR (300 MHz, CDCl ₃ ): δ 7.31-7.18 (m, 4H), 6.75 (s, 2H), 6.72 (d, J = 7.8 Hz, 1H), 6.59 (d, J = 7.8 Hz, 1H) , 5.94 (s, 2H), 4.45 (d, J = 5.4 Hz, 1H), 4.35 (d, J = 5.4 Hz, 1H), 4.13 (s, 1H), 3.54 (dd, J = 5.1 Hz, 8.9 Hz , 1H), 3.25 (dd, J = 12.7, 16.7 Hz, 1H), 3.00 (dd, J = 5.1, 8.9 Hz, 1H), 2.15 (s, 3H), 1.26 (s, 1H)

Next, pyridine (0.8 ml) was added to a solution of the obtained compound (1) -102-1 (0.364 g, 1 mmol) in methylene chloride (10 ml), and the mixture was stirred at 0 ° C. 4-Chlorobenzoyl chloride (0.35 g, 2 mmol) was added dropwise to the solution, and the mixture was warmed to room temperature and stirred for 10 hours. After completion of the reaction, the reaction mixture was diluted with methylene chloride (15 ml), washed with water (30 ml), and the organic layer was dried over magnesium sulfate. Subsequently, the solvent was distilled off with an evaporator, and the residue was purified by silica gel column chromatography (mobile phase: hexane / ethyl acetate = 2/3 (volume ratio)) to obtain crystals of compound (1) -102 ( 0.24 g, yield 38%). Identification data of the compound (1) -102 are as follows.
mp: 134-136 ° C
IR (KBr): 2983, 1681, 1592, 1425,1322, 1263, 1091, 927, 852, 761cm ^-1
1 H NMR (300 MHz, CDCl ₃ ): δ 7.91 (d, J = 6.6 Hz, 2H), 7.44 -7.25 (m, 6H), 6.72 (d, J = 8.1 Hz, 1H), 6.70 (s, 1H) , 6.59 (d, J = 8.1 Hz, 1H), 5.94 (s, 2H), 5.41 (s, 1H), 4.55 (d, J = 5.4 Hz, 1H), 4.50 (d, J = 5.4 Hz, 1H) , 3.68 (dd, J = 5.1 Hz, 9.0 Hz, 1H), 3.28 (dd, J = 12.6 Hz, 39.6 Hz, 2H), 3.17 (dd, J = 5.4 Hz, 9.0 Hz, 1H), 2.18 (s, 3H)

[Production Example 3]
(Production of Compound (1) -103)

Benzylamine (0.66 g, 6.2 mmol) was dissolved in acetonitrile (5 ml), and a solution of 2-chloromethylbenzaldehyde (0.46 g, 3 mmol) in acetonitrile (10 ml) was dissolved in the solution at room temperature. The solution was added dropwise and stirred at room temperature for 1 hour. Then, the reaction mixture was diluted with methylene chloride (10 ml) and then washed twice with water (10 ml) and once with saturated brine. The organic layer was dried over magnesium sulfate, and the solvent was distilled off with an evaporator to obtain crude benzylisoindole.
Next, N-methylmaleimide (0.41 g, 3.6 mmol) was dissolved in methylene chloride (10 ml), and the resulting solution of the crude benzylisoindole obtained above was dissolved in methylene chloride (10 ml). Was added dropwise at 0 ° C. and stirred at 0 ° C. for 5 minutes. The solvent was removed by an evaporator, and the residue was purified by silica gel column chromatography (mobile phase: hexane / ethyl acetate (1/1, volume ratio)) to obtain crystals of compound (1) -103 (yield 0). .85 g, 85% yield). By spectral analysis, it was confirmed that Compound (1) -103 was an endo isomer. Identification data of the compound (1) -103 are as follows.
mp: 155-158 ° C
IR (KBr): 3436, 3010, 2821, 2293, 1763, 1436, 1288, 1132, 768, 749cm ^-1
1 H NMR (270 MHz, CDCl ₃ ): δ 7.35-7.18 (m, 9H), 4.58 (d, J = 1.6 Hz, 1H), 4.57 (d, J = 1.6 Hz, 1H), 3.69 (d, J = 1.6 Hz, 1H), 3.68 (d, J = 1.6 Hz, 1H), 3.38 (s, 2H), 2.26 (s, 3H)

[Production Example 4]
(Production of Compound (1) -104)

Compound (1) -103 (0.75 mmol) obtained above was dissolved in ethanol (12 ml), and sodium borohydride (NaBH ₄ ) (0.117 g, 3 mmol) was dissolved in ethanol (12 ml) in the solution. The solution dissolved in was dropped at room temperature and stirred at room temperature for 40 hours. Next, the reaction mixture is adjusted to pH 5-6 using dilute hydrochloric acid aqueous solution (1N), diluted with methylene chloride (20 ml), washed with water (20 ml) and saturated aqueous sodium hydrogen carbonate solution, and the organic layer is washed with magnesium sulfate. And dried. Subsequently, the solvent was distilled off with an evaporator, and one carbonyl group of compound (1) -103 was reduced (“—C (═O) —” was converted to “—CH (—OH) —”). Compound (1) -104-1 was obtained as a crude product (yield 74%).

Next, pyridine (1.0 ml) was added to a solution of the obtained compound (1) -104-1 (0.32 g, 1 mmol) in methylene chloride (10 ml), and the mixture was stirred at 0 ° C. 4-Chlorobenzoyl chloride (0.35 g, 2 mmol) was added dropwise to the solution, and the mixture was warmed to room temperature and stirred for 10 hours. After completion of the reaction, the reaction mixture was diluted with methylene chloride (15 ml), washed with water (30 ml), and the organic layer was dried over magnesium sulfate. Subsequently, the solvent was distilled off with an evaporator, and the residue was purified by silica gel column chromatography (mobile phase: hexane / ethyl acetate = 2/3 (volume ratio)) to obtain crystals of compound (1) -104 ( 0.24 g, 53% yield). Identification data of the compound (1) -104 are as follows.
IR (KBr): 3416, 2980, 1704, 1593, 1399,1263, 1092, 1014, 852, 761cm ^-1
1 H NMR (300 MHz, CDCl ₃ ): δ 7.90 (d, J = 6.0 Hz, 2H), 7.48 -7.17 (m, 11H), 5.42 (s, 1H), 4.57 (d, J = 5.4 Hz, 1H) , 4.52 (d, J = 5.4 Hz, 1H), 3.68 (dd, J = 5.4 Hz, 9.0 Hz, 1H), 3.49 (dd, J = 12.6 Hz, 35.7 Hz, 2H), 3.18 (dd, J = 5.4 Hz, 9.0 Hz, 1H), 2.19 (s, 3H)

[Production Example 5]
(Production of Compound (1) -105)

Furfurylamine (3.40 g, 33.6 mmol) was dissolved in acetonitrile (30 ml), and a solution of 2-chloromethylbenzaldehyde (2.60 g, 16.8 mmol) in acetonitrile (30 ml) was dissolved in the solution. The solution was added dropwise at room temperature and stirred at room temperature for 15 minutes. The reaction mixture was then diluted with methylene chloride (20 ml), and then washed twice with water (50 ml) and once with saturated brine. The organic layer was dried over magnesium sulfate, and the solvent was distilled off with an evaporator to obtain crude furfuryl isoindole.
Next, N-methylmaleimide (2.00 g, 18.5 mmol) was dissolved in methylene chloride (20 ml), and the crude furfurylisoindole obtained above was dissolved in methylene chloride (20 ml). The solution was added dropwise at 0 ° C. and stirred at 0 ° C. for 15 minutes. The solvent was distilled off with an evaporator, and the residue was purified by recrystallization to obtain crystals of compound (1) -105 (yield: 2.71 g, yield: 52%). It was confirmed by spectral analysis that compound (1) -105 was an endo isomer. Identification data of the compound (1) -105 are as follows.
mp: 114-116 ° C. (cyclohexane: diisopropyl ether = 1: 1)
IR (KBr): 3440, 3040, 2871, 1762,1693, 1432, 1379, 1292, 1132,842, 753 cm ^-1
1 H NMR (270 MHz, CDCl ₃ ): δ7.27-7.25 (m, 4H), 4.78 (d, J = 3.0 Hz, 1H), 4.73 (d, J = 3.2 Hz, 1H), 4.78-3.71 ( m, 5H), 2.329 (d, J = 2.4 Hz, 2H), 2.25 (s, 3H), 1.92-1.79 (m, 3H), 1.43-1.39 (m, 1H)

<Production of Compound (1) -2>
[Production Example 6]
(Production of Compound (1) -201)

m-Chloroperbenzoic acid (mCPBA) (0.13 g, 0.75 mmol) was dissolved in methylene chloride (10 ml), and the compound (1) -103 (0.187 g, 0.59 mmol) was dissolved in the solution. A solution dissolved in methylene chloride (10 ml) was added dropwise at 0 ° C. and stirred for 5 minutes. Then, a solution of 1,4-diazabicyclo [2.2.2] octane (DABCO) (0.083 g, 0.75 mmol) dissolved in methylene chloride (5 ml) was added dropwise at room temperature and stirred for 10 hours. The obtained reaction mixture was diluted with methylene chloride (20 ml), washed with water (30 ml), and the organic layer was dried over magnesium sulfate. Subsequently, the solvent was distilled off with an evaporator, and the residue was purified by silica gel column chromatography (mobile phase: hexane / ethyl acetate = 4/1 (volume ratio)) to obtain Compound (1) -201 as white crystals. (Yield 0.174 g, Yield 89%). Identification data of the compound (1) -201 are as follows.
mp: 148-172 ℃
IR (KBr): 3028, 2977, 2955, 2888, 1697, 1436cm ^-1
1 H NMR (300 MHz, CDCl ₃ ): δ 7.48-7.23 (m, 9H), 5.39 (d, J = 4.5Hz 1H), 4.53 (d, J = 3.9Hz, 1H), 3.64 (dd, J = 4.5 Hz 1H), 3.64 (m, 2 H), 3.14 (d, J = 12.4Hz, 1H), 2.49 (s, 3H)

[Production Example 7]
(Production of Compound (1) -202)

m-Chloroperbenzoic acid (mCPBA) (0.311 g, 1.8 mmol) was dissolved in methylene chloride (15 ml), and the compound (1) -101 (0.541 g, 1.5 mmol) was dissolved in the solution. A solution dissolved in methylene chloride (6 ml) was added dropwise at 0 ° C. and stirred for 5 minutes. Next, a solution of 1,4-diazabicyclo [2.2.2] octane (DABCO) (0.202 g, 1.8 mmol) dissolved in methylene chloride (5 ml) was added dropwise at room temperature and stirred for 10 hours. The obtained reaction mixture was diluted with methylene chloride (20 ml), washed with water (50 ml), and the organic layer was dried over magnesium sulfate. Subsequently, the solvent was distilled off with an evaporator, and the residue was purified by silica gel column chromatography (mobile phase: hexane / ethyl acetate = 4/1 (volume ratio)) to obtain Compound (1) -202 as white crystals. (Yield 0.509 g, 90% yield). Identification data for the compound (1) -202 are as follows.
mp.186-194 ℃
IR: 3212, 2930, 2901, 1652, 1501, 1251, 1092, 1040cm ^-1
1 H NMR (300 MHz, CDCl ₃ ): δ 7.47-7.19 (m, 4H), 6.79-6.61 (m, 3H), 5.96 (s, 2H), 5.35 (d, J = 4.7 Hz 1H), 4.51 (d , J = 3.9Hz 1H), 3.66 (d, J = 3.9Hz, 2H), 3.59 (dd, J = 3.9Hz 2H), 3.48 (d, J = 12.4 Hz 1H), 3.03 (d, J = 12.4Hz , 1H), 2.49 (s, 3H)

[Production Example 8]
(Production of Compound (1) -203)

m-Chloroperbenzoic acid (mCPBA) (0.219 g, 1.6 mmol) was dissolved in methylene chloride (5 ml), and the compound (1) -105 (0.316 g, 1.0 mmol) was dissolved in the solution. A solution dissolved in methylene chloride (9 ml) was added dropwise at 0 ° C. and stirred for 5 minutes. Next, a saturated aqueous sodium carbonate solution was added and stirred for 10 hours. The resulting reaction mixture was diluted with methylene chloride (20 ml), washed with water (50 ml), and the organic layer was dried over magnesium sulfate. Subsequently, the solvent was distilled off with an evaporator, and the residue was purified by silica gel column chromatography (mobile phase: ethyl acetate) to obtain Compound (1) -203 as white crystals (yield 0.24 g, yield 73%). ). Identification data of the compound (1) -203 are as follows.
mp.175-177 ℃
IR: 3456, 2954,, 2880, 1697, 1438, 1291, 1112, 1046cm ^-1
1 H NMR (300 MHz, CDCl ₃ ): δ 7.38-7.36 (m, 2H), 7.28-7.25 (m, 2H), 5.31 (d, J = 4.7 Hz 1H), 4.74 (d, J = 4.1Hz 1H) , 4.02-3.96 (m, 1H), 3.85-3.74 (m, 3H), 3.66 (dd, J = 4.7Hz 1H), 2.50 (s, 3H), 2.34-2.16 (m, 2H), 1.90-1.75 ( m, 3H), 1.28-1.25 (m, sH)

[Examples 1 to 3]
Using the compounds (1) -102, (1) -201, and (1) -203 obtained above, plant resistance was induced.
The resistance-inducing activity of each compound (1) was evaluated by the following procedure. That is, a reporter gene (PR-1a-LUC) in which a firefly luciferase gene (LUC) was linked to a defense response-related gene promoter (PR-1a) was constructed, and this was introduced into Arabidopsis thaliana for transformation. The transformed Arabidopsis seeds were then sown in a 96-well multiwell plate and germinated in a 1 mM luciferin aqueous solution. Next, a dimethyl sulfoxide (DMSO) solution of each of the above compounds was prepared, and this solution was added to each well so that the concentration of these compounds was 30 μM, thereby treating the seedlings of transformed Arabidopsis thaliana.
Next, by using a photo counting device (ARGUS system, manufactured by Hamamatsu Photonics) and software (AQUACOSMOS, manufactured by Hamamatsu Photonics), the luminescence intensity in each well is measured, and the expression level of the reporter gene is measured, The resistance-inducing effects of Compound (1) -102 (Example 1), Compound (1) -201 (Example 2), and Compound (1) -203 (Example 3) were evaluated.

[Reference Example 1]
Instead of each of the above compounds (1), acylbenzolar S-methyl (S-methylbenzo [1,2,3] thiadiazole-7-carbothioate) is used, and the acylbenzoal S-methyl concentration is adjusted to 50 μM. The resistance-inducing activity of acibenzolar S methyl was evaluated in the same manner as in Examples 1 to 3 except that a DMSO solution of benzoral S methyl was added. Acibenzoral S-methyl is a known inducer.

[Comparative Example 1]
The luminescence intensity in each well was measured in the same manner as in Examples 1 to 3, except that only DMSO was added instead of the DMSO solution of each compound (1).

The measurement results of the luminescence intensity in Examples 1 to 3, Reference Example 1 and Comparative Example 1 are shown in FIG. The vertical axis in the graph of FIG. 1 represents the luminescence intensity (number of photons / min / μm ² ), and the horizontal axis represents the time after the compound (1) or the benzobenzoal S-methyl DMSO solution or DMSO was added to each well ( 0 hours to 10 days).
As is apparent from FIG. 1, all of the compounds (1) -102, (1) -201, and (1) -203 had sufficient resistance-inducing activity. Thus, it has been confirmed that the compound (1) having a novel skeleton completely different from the conventional inducer has resistance-inducing activity.

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

Claims (2)

A plant resistance inducer comprising a compound represented by the following general formula (1) as an active ingredient.

Wherein X ¹ is a group represented by the following general formula (1a) or (1b); X ² and X ³ are each independently a carbonyl group or a group represented by the following general formula (1c) Z is a monovalent group other than a hydrogen atom; R ¹ is a hydrogen atom or a hydrocarbon group which may have a substituent; m is an integer of 0 to 4, and m is 2 to 4 And the plurality of Z may be the same or different from each other.)

(In the formula, R ² is a hydrocarbon group which may have a substituent; Y ¹ is an aromatic group.) The plant resistance inducer according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (1) -1A or (1) -2A.

(In the formula, R ^2a is an ^optionally substituted aryl group or a cyclic alkyl group; R ¹⁰ is an alkyl group having 1 to 15 carbon atoms or an aryl group having 6 to 15 carbon atoms; G Is a halogen atom; n ₁ is an integer of ₁ to 5; n ₂ is an integer of 0 to 5, and when n ₂ is ₂ to 5, a plurality of G may be the same or different from each other .)

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