JP2014118404A - Auxin biosynthesis inhibitor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel auxin biosynthesis inhibitor having excellent properties compared to known auxin biosynthesis inhibitors.SOLUTION: The invention relates to a compound represented by the formula (I) or a salt thereof.

Description

  The present invention relates to a novel auxin biosynthesis inhibitor. The present invention also relates to a method of using the inhibitor.

  Auxin is a plant hormone known to be involved in plant development, growth, differentiation and various environmental responses. As natural auxin, indole-3-acetic acid (IAA) is known to be the most universally distributed. Other natural auxins such as indole-3-butyric acid (IBA) and 4-chloroindole-3-acetic acid (4-Cl-IAA) are also known.

  The primary natural auxin, IAA, is very chemically unstable. In plants, there is an IAA metabolic pathway that degrades IAA. For this reason, synthetic auxins are widely used as agricultural chemicals or phytochemical regulators in the fields of agriculture and phytochemistry. As synthetic auxins, 2,4-dichlorophenoxyacetic acid (2,4-D), 1-naphthaleneacetic acid (NAA), 2-methyl-4-chlorophenoxybutyric acid (MCPB), and the like are known. For example, 2,4-D is used as a herbicide and plant tissue culture reagent. MCPB has been used as a selective herbicide for paddy broadleaf weeds.

  Auxin is known to be biosynthesized by multiple pathways. However, the overall picture of the auxin or IAA biosynthetic pathway has not yet been established. To date, it has been confirmed that there are two routes: a route that passes through L-tryptophan and a route that does not pass (non-tryptophan route). The route through L-tryptophan is further branched into four or more routes, each of which is catalyzed by a different biosynthetic enzyme.

  As mentioned above, the auxin biosynthetic pathway is very complex. In addition, L-tryptophan, which is an aromatic amino acid, is used as a main biosynthetic precursor. For example, glyphosate, a known herbicide, inhibits 5-enolpyruvyl-3-phosphoshikimate synthase (EPSPS), an enzyme involved in the biosynthesis of aromatic amino acids. For this reason, glyphosate expresses herbicidal activity by broadly affecting the biosynthesis of aromatic amino acids and / or other secondary metabolites located downstream of EPSPS. However, in the case of an inhibitor of an enzyme that affects biosynthesis of a wide range of metabolites as described above, it may adversely affect biosynthesis of metabolites other than the target compound. For this reason, a compound that specifically inhibits a specific pathway in the biosynthesis pathway of auxin has been developed. For example, Patent Document 1 discloses L-α- (2-aminoethoxyvinyl) glycine (AVG), L-aminooxyphenylpropionic acid (L-AOPP), aminooxyacetic acid (AOA), and 2-aminooxyisobutyric acid ( Auxin biosynthesis inhibitors such as AOIBA) are described. Patent Document 2 describes a novel auxin biosynthesis inhibitor in which the phenyl group, carboxyl group and aminooxy group of L-AOPP are modified.

International Publication 2008/150031 Pamphlet International publication 2012/118216 pamphlet

  Several problems existed with the auxin biosynthesis inhibitors as described above. For example, L-AOPP has low stability, and when added to a plant medium, it is difficult to continuously exhibit a plant growth inhibitory effect. L-AOPP is a compound used as an inhibitor of phenylalanine ammonia lyase (PAL), which is known as the main biosynthetic enzyme of phenylpropanoids. For this reason, L-AOPP may inhibit not only auxin biosynthesis but also the biosynthesis of phenylpropanoid secondary metabolites such as anthocyanins, flavonoids and lignin, and the plant hormone salicylic acid.

  In view of the above problems, the present inventors have developed a novel auxin biosynthesis inhibitor with improved substrate specificity, permeability and stability and reduced side effects compared to known auxin biosynthesis inhibitors. (Patent Document 2). However, these novel auxin biosynthesis inhibitors have room for further improvement.

  Therefore, an object of the present invention is to provide a novel auxin biosynthesis inhibitor having superior properties as compared with known auxin biosynthesis inhibitors.

  As a result of various studies on means for solving the above problems, the present inventor has obtained an auxin biosynthesis inhibitory activity by substituting an aminooxy group contained in the skeleton of L-AOPP with a group not containing a nitrogen atom. The inventors have found that it can be further improved and completed the present invention.

［式中、n、Ar、A、B、R¹、R²、R³、R⁴及びR⁵は、以下の［a］〜［f］のいずれかを満たす：
［a］
nは、1であり、
Arは、非置換若しくは2個以上のハロゲンで置換されたビフェニル、フェニルで置換されたチエニル、又は非置換若しくはC₁〜C₅アルコキシで置換されたナフチルであり、
A及びBは、単結合であり、
R¹及びR²は、水素であり、
Arが、非置換若しくは2個以上のハロゲンで置換されたビフェニル又はフェニルで置換されたチエニルのとき、
R³は、ヒドロキシルであり、
R⁴は、水素又は置換若しくは非置換のC₁〜C₅アルキルであり、
R⁵は、カルボン酸又は置換若しくは非置換のC₁〜C₅アルキルとのカルボン酸エステルであり、
Arが、非置換のナフチルのとき、
R³は、ヒドロキシルであり、
R⁴は、置換若しくは非置換のC₁〜C₅アルキルであり、
R⁵は、カルボン酸であり、
Arが、C₁〜C₅アルコキシで置換されたナフチルのとき、
R³は、ヒドロキシルであり、
R⁴は、水素であり、
R⁵は、カルボン酸である。
［b］
nは、1であり、
Arは、ナフタレン-1-イルであり、
Aは、-O-CH₂-又は-O-であり、
R¹及びR³は、水素であり、
R²及びR⁴は、それらが結合する炭素原子と一緒になってビニレンを形成し、
R⁵は、置換若しくは非置換のC₁〜C₅アルキルとのカルボン酸エステルであり、
Aが、-O-CH₂-のとき、
Bは、単結合又は-CH₂-であり、
Aが、-O-のとき、
Bは、-CH₂-である。
［c］
nは、1であり、
Arは、5-フェニルチエン-2-イル、又は非置換若しくはC₁〜C₅アルコキシで置換されたナフチルであり、
Arが、5-フェニルチエン-2-イルのとき、
A及びBは、単結合であり、
R¹及びR³は、水素であり、
R²及びR⁴は、それらが結合する炭素原子と一緒になってエポキシを形成し、
R⁵は、カルボン酸又は置換若しくは非置換のC₁〜C₅アルキルとのカルボン酸エステルであり、
Arが、非置換若しくはC₁〜C₅アルコキシで置換されたナフチルのとき、
Aは、ビニレンであり、
Bは、単結合であり、
R¹及びR³は、水素であり、
R²及びR⁴は、それらが結合する炭素原子と一緒になってエポキシを形成し、
R⁵は、カルボン酸又は置換若しくは非置換のC₁〜C₅アルキルとのカルボン酸エステルである。
［d］
nは、1であり、
Arは、非置換のナフチル又は非置換のインドリルであり、
A及びBは、単結合であり、
R³及びR⁴は、水素であるか、又はそれらが結合する炭素原子と一緒になってビニリデンを形成し、
Arが、非置換のナフチルのとき、
R¹及びR²は、それらが結合する炭素原子と一緒になってカルボニルを形成し、
R⁵は、ホスホン酸であり、
Arが、非置換のインドリルのとき、
R¹及びR²は、水素であるか、又はそれらが結合する炭素原子と一緒になってカルボニルを形成し、
R⁵は、置換若しくは非置換のC₁〜C₅アルキルとのカルボン酸エステルである。
［e］
nは、1であり、
Arは、非置換のナフチルであり、
Aは、-O-CH₂-であり、
Bは、単結合であり、
R¹は、水素であり、
R²及びR⁴は、それらが結合する炭素原子と一緒になってビニレンを形成し、
R³は、置換若しくは非置換のC₁〜C₅アシルアミノであり、
R⁵は、カルボン酸又は置換若しくは非置換のC₁〜C₅アルキルとのエステルである。
［f］
nは、0であり、
Arは、非置換のナフチルであり、
A及びBは、単結合であり、
R¹及びR²は、水素であり、
R⁵は、N-ヒドロキシフタル酸イミドとのカルボン酸エステルである。］
で表される化合物又はその塩。 That is, the gist of the present invention is as follows.
(1) Formula (I):

[Wherein, n, Ar, A, B, R ¹ , R ² , R ³ , R ⁴ and R ⁵ satisfy any of the following [a] to [f]:
[A]
n is 1,
Ar is unsubstituted or biphenyl substituted with two or more halogen, thienyl substituted with phenyl, or naphthyl substituted by unsubstituted or C ₁ -C ₅ alkoxy,
A and B are single bonds,
R ¹ and R ² are hydrogen,
When Ar is biphenyl unsubstituted or substituted with two or more halogens or thienyl substituted with phenyl,
R ³ is hydroxyl
R ⁴ is hydrogen or substituted or unsubstituted C ₁ -C ₅ alkyl,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When Ar is unsubstituted naphthyl,
R ³ is hydroxyl
R ⁴ is a substituted or unsubstituted C ₁ -C ₅ alkyl;
R ⁵ is a carboxylic acid,
Ar is when naphthyl substituted by C ₁ -C ₅ alkoxy,
R ³ is hydroxyl
R ⁴ is hydrogen,
R ⁵ is a carboxylic acid.
[B]
n is 1,
Ar is naphthalen-1-yl,
A is —O—CH ₂ — or —O—,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form vinylene,
R ⁵ is a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When A is -O-CH _2-
B is a single bond or —CH ₂ —;
When A is -O-
B is —CH ₂ —.
[C]
n is 1,
Ar is a naphthyl substituted with 5-phenyl-thien-2-yl, or unsubstituted or C ₁ -C ₅ alkoxy,
When Ar is 5-phenylthien-2-yl,
A and B are single bonds,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form an epoxy,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When Ar is a naphthyl substituted by unsubstituted or C ₁ -C ₅ alkoxy,
A is vinylene,
B is a single bond,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form an epoxy,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[D]
n is 1,
Ar is unsubstituted naphthyl or unsubstituted indolyl;
A and B are single bonds,
R ³ and R ⁴ are hydrogen or together with the carbon atom to which they are attached form vinylidene;
When Ar is unsubstituted naphthyl,
R ¹ and R ² together with the carbon atom to which they are attached form a carbonyl,
R ⁵ is phosphonic acid,
When Ar is an unsubstituted indol,
R ¹ and R ² are hydrogen or together with the carbon atom to which they are attached form a carbonyl,
R ⁵ is a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[E]
n is 1,
Ar is unsubstituted naphthyl,
A is -O-CH _2-
B is a single bond,
R ¹ is hydrogen;
R ² and R ⁴ together with the carbon atom to which they are attached form vinylene,
R ³ is a substituted or unsubstituted C ₁ -C ₅ acylamino;
R ⁵ is a carboxylic acid or an ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[F]
n is 0,
Ar is unsubstituted naphthyl,
A and B are single bonds,
R ¹ and R ² are hydrogen,
R ⁵ is a carboxylic acid ester with N-hydroxyphthalimide. ]
Or a salt thereof.

［式中、n’、Ar’、A’、B’、R^1’、R^2’、R^3’、R^4’及びR^5’は、以下の［a’］〜［g’］のいずれかを満たす：
［a’］
n’は、1であり、
Ar’は、置換若しくは非置換のアリール、又は置換若しくは非置換のヘテロアリールであり、
A’及びB’は、単結合であり、
R^1’及びR^2’は、水素であり、
R^3’は、ヒドロキシルであり、
R^4’は、水素又は置換若しくは非置換アルキルであり、
R^5’は、カルボン酸又は置換若しくは非置換アルキルとのカルボン酸エステルである。
［b’］
n’は、1であり、
Ar’は、置換若しくは非置換のアリール、又は置換若しくは非置換のヘテロアリールであり、
A’は、-O-CH₂-又は-O-であり、
B’は、単結合又は-CH₂-であり、
R^1’及びR^3’は、水素であり、
R^2’及びR^4’は、それらが結合する炭素原子と一緒になってビニレンを形成し、
R^5’は、カルボン酸又は置換若しくは非置換アルキルとのカルボン酸エステルである。
［c’］
n’は、1であり、
Ar’は、置換若しくは非置換のアリール、又は置換若しくは非置換のヘテロアリールであり、
A’は、単結合、ビニレン又はカルボニルであり、
B’は、単結合であり、
R^1’及びR^3’は、水素であり、
R^2’及びR^4’は、それらが結合する炭素原子と一緒になってエポキシ又はビニレンを形成し、
R^5’は、カルボン酸又は置換若しくは非置換アルキルとのカルボン酸エステルである。
［d’］
n’は、1であり、
Ar’は、置換若しくは非置換のアリール、又は置換若しくは非置換のヘテロアリールであり、
A’は、単結合又は-O-CH₂-であり、
B’は、単結合であり、
R^1’及びR^2’は、水素であるか、又はそれらが結合する炭素原子と一緒になってカルボニルを形成し、
R^3’及びR^4’は、水素であるか、又はそれらが結合する炭素原子と一緒になってビニリデンを形成し、
R^5’は、カルボン酸若しくはホスホン酸、又は置換若しくは非置換アルキルとのカルボン酸若しくはホスホン酸エステルである。
［e’］
n’は、1であり、
Ar’は、置換若しくは非置換のアリール、又は置換若しくは非置換のヘテロアリールであり、
A’は、単結合又は-O-CH₂-であり、
B’は、単結合であり、
R^1’は、水素であり、
R^2’及びR^4’は、それらが結合する炭素原子と一緒になってビニレンを形成し、
R^3’は、アシルアミノであり、
R^5’は、カルボン酸又は置換若しくは非置換アルキルとのカルボン酸エステルであるか、或いは
R^3’及びR^5’は、それらが結合する炭素原子と一緒になってオキサゾール-5(4H)-オン環を形成する。
［f’］
n’は、0であり、
Ar’は、置換若しくは非置換のアリール、又は置換若しくは非置換のヘテロアリールであり、
A’は、単結合又は-O-であり、
B’は、単結合であり、
R^1’及びR^2’は、水素であり、
R^5’は、カルボン酸、N-ヒドロキシフタル酸イミドとのカルボン酸エステル又はカルボン酸ヒドラジドである。
［g’］
n’は、1であり、
Ar’は、置換若しくは非置換のアリール、又は置換若しくは非置換のヘテロアリールであり、
A’は、単結合であり、
B’は、単結合又はメチレンであり、
R^1’及びR^2’は、水素であり、
R^3’は、水素又はヒドロキシルであり、
R^4’は、水素であり、
R^5’は、ヒドロキシルである。］
で表される化合物又はその塩を有効成分として含むオーキシン生合成阻害剤。 (2) Formula (I '):

[Wherein, n ′, Ar ′, A ′, B ′, R ^{1 ′} , R ^{2 ′} , R ^{3 ′} , R ^{4 ′} and R ^{5 ′} are any of the following [a ′] to [g ′]. Satisfy:
[A ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ and B ′ are single bonds,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{3 ′} is hydroxyl,
R ^{4 ′} is hydrogen or substituted or unsubstituted alkyl;
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[B ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is —O—CH ₂ — or —O—,
B ′ is a single bond or —CH ₂ —;
R ^{1 ′} and R ^{3 ′} are hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form vinylene,
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[C ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond, vinylene or carbonyl,
B ′ is a single bond,
R ^{1 ′} and R ^{3 ′} are hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form an epoxy or vinylene;
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[D ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—CH ₂ —,
B ′ is a single bond,
R ^{1 ′} and R ^{2 ′} are hydrogen or together with the carbon atom to which they are attached form a carbonyl,
R ^{3 ′} and R ^{4 ′} are hydrogen or together with the carbon atom to which they are attached form vinylidene;
R ^{5 ′} is a carboxylic acid or phosphonic acid, or a carboxylic acid or phosphonic acid ester with a substituted or unsubstituted alkyl.
[E ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—CH ₂ —,
B ′ is a single bond,
R ^{1 ′} is hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form vinylene,
R ^{3 ′} is acylamino,
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl, or
R ^{3 ′} and R ^{5 ′} together with the carbon atom to which they are attached form an oxazol-5 (4H) -one ring.
[F ']
n 'is 0,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—,
B ′ is a single bond,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{5 ′} is a carboxylic acid, a carboxylic acid ester with N-hydroxyphthalimide, or a carboxylic acid hydrazide.
[G ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond,
B ′ is a single bond or methylene,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{3 ′} is hydrogen or hydroxyl;
R ^{4 ′} is hydrogen,
R ^{5 ′} is hydroxyl. ]
An auxin biosynthesis inhibitor comprising a compound represented by the formula:

(3) The auxin biosynthesis inhibitor according to (2), which is used for controlling undesirable plants.
(4) A method for inhibiting auxin biosynthesis in the plant, comprising treating the plant with the auxin biosynthesis inhibitor according to (2).

(5) A method for regulating growth of a plant, comprising treating the plant with the auxin biosynthesis inhibitor according to (2).
(6) A method for weeding an undesirable plant, comprising treating the undesirable plant with the auxin biosynthesis inhibitor according to (2).

  According to the present invention, it is possible to provide a novel auxin biosynthesis inhibitor having superior properties as compared with known auxin biosynthesis inhibitors.

FIG. 1 is a graph showing the quantitative results of the amount of endogenous IAA in Arabidopsis thaliana. The vertical axis represents the relative value based on the amount of endogenous IAA in the control plantlets. FIG. 2-1 is a diagram showing the forms of a control group and each test group in an Arabidopsis thaliana growth test. FIG. 2-2 is a diagram showing the form of each test plot in an Arabidopsis thaliana growth test. FIG. 2-3 is a diagram showing the form of each test plot in the growth test of Arabidopsis thaliana. FIG. 2-4 is a diagram showing the form of each test plot in the growth test of Arabidopsis thaliana. FIG. 2-5 is a diagram showing the form of each test plot in an Arabidopsis thaliana growth test. FIG. 2-6 is a diagram showing the form of each test plot in the growth test of Arabidopsis thaliana. FIG. 2-7 is a diagram showing the form of each test plot in an Arabidopsis thaliana growth test. FIG. 2-8 is a diagram showing the form of each test plot in the growth test of Arabidopsis thaliana. FIG. 2-9 is a diagram showing the form of each test plot in the growth test of Arabidopsis thaliana. FIG. 3-1 is a diagram showing the forms of a control group and each test group in a rice growth test. FIG. 3-2 is a diagram showing the form of each test plot in the rice growth test. Fig. 3-3 is a diagram showing the form of each test plot in the rice growth test. FIG. 3-4 is a diagram showing the form of each test plot in the rice growth test. FIG. 3-5 is a diagram showing the form of each test plot in the rice growth test. FIG. 3-6 is a diagram showing the form of each test plot in the rice growth test. FIG. 3-7 is a diagram showing the form of each test plot in the rice growth test. FIG. 3-8 is a diagram showing the form of each test plot in the rice growth test. FIG. 4 is a graph showing the results of Arabidopsis thaliana growth tests for the compounds of Examples and Reference Example 1.

で表される化合物又はその塩若しくは溶媒和物に関する。 <1. New compound>
The present invention is directed to formula (I):

Or a salt or solvate thereof.

As used herein, “alkyl” means a straight or branched chain aliphatic hydrocarbon group containing the specified number of carbon atoms. For example, “C ₁ -C ₅ alkyl” means a straight or branched hydrocarbon chain containing at least 1 and at most 5 carbon atoms. Suitable alkyls include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and n-pentyl.

  In the present specification, “alkenyl” means a group in which one or more C—C single bonds of the alkyl are substituted with double bonds. Suitable alkenyls include, but are not limited to, vinyl, 1-propenyl, allyl, 1-methylethenyl (isopropenyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2 -Methyl-2-propenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-pentenyl and the like can be mentioned.

  In the present specification, “alkynyl” means a group in which one or more C—C single bonds of the alkyl are substituted with triple bonds. Suitable alkynyls include, but are not limited to, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, and the like. Can do.

As used herein, “cycloalkyl” means an alicyclic alkyl containing the specified number of carbon atoms. For example, “C ₃ -C ₆ cycloalkyl” means a cyclic hydrocarbon group containing at least 3 and at most 6 carbon atoms. Suitable cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

  In the present specification, “cycloalkenyl” means a group in which one or more C—C single bonds of the cycloalkyl are substituted with double bonds. Suitable cycloalkenyl includes, but is not limited to, cyclobutenyl, cyclopentenyl, cyclohexenyl and the like.

  In the present specification, “cycloalkynyl” means a group in which one or more C—C single bonds of the cycloalkyl are substituted with triple bonds. Suitable cycloalkynyl includes, but is not limited to, cyclobutynyl, cyclopentynyl, cyclohexynyl, and the like.

  In the present specification, “heterocyclyl” means that one or more carbon atoms of the cycloalkyl, cycloalkenyl or cycloalkynyl are each independently selected from nitrogen (N), sulfur (S) and oxygen (O). This means a group substituted with a heteroatom. In this case, substitution with N or S includes substitution with N-oxide or S oxide or dioxide, respectively. Suitable heterocyclyls include, but are not limited to, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl, tetrahydrothienyl, tetrahydropyranyl, dihydropyranyl, tetrahydrothiopyranyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl. it can.

  In the present specification, “aryl” means an aromatic ring group having 6 to 15 carbon atoms. Suitable aryls include, but are not limited to, phenyl, biphenyl, naphthyl, anthryl (anthracenyl), and the like.

  In the present specification, “arylalkyl” means a group in which one of hydrogen atoms of the alkyl is substituted with the aryl. Suitable arylalkyls include, but are not limited to, benzyl, 1-phenethyl, 2-phenethyl, and the like.

  In the present specification, “arylalkenyl” means a group in which one of the hydrogen atoms of the alkenyl is substituted with the aryl. Suitable arylalkenyls include, but are not limited to, styryl and the like.

  In the present specification, “heteroaryl” means that one or more carbon atoms of the aryl are each independently substituted with a heteroatom selected from nitrogen (N), sulfur (S) and oxygen (O). Means group. In this case, substitution with N or S includes substitution with N-oxide or S oxide or dioxide, respectively. Suitable heteroaryl include, but are not limited to, for example, furanyl, thienyl (thiophenyl), pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, isothiazolyl, pyridyl, pyridazinyl, pyrazinyl, Examples include pyrimidinyl, quinolinyl, isoquinolinyl and indolyl.

  In the present specification, “heteroarylalkyl” means a group in which one of the hydrogen atoms of the alkyl is substituted with the heteroaryl.

  In the present specification, “acyl” means a group in which a monovalent group selected from the groups described above and carbonyl are linked. Suitable acyls include, but are not limited to, acetyl, propionyl, benzoyl, and the like.

The groups described above are each independently unsubstituted or one or more halogen, OH, NH ₂ , NO ₂ , C (O) Z (where Z is hydrogen, hydroxyl, NH ₂ or Or a monovalent group selected from the groups described above can be further substituted.

  In the present specification, “halogen” or “halo” means fluorine, chlorine, bromine or iodine.

  The present inventors searched for a compound having an auxin biosynthesis inhibitory activity. As a result, the compound represented by the formula (I) or the formula (I ′) was found as a compound having a high auxin biosynthesis inhibitory activity. Among these, the compound represented by the formula (I) is a novel compound found by the present inventors.

In the compound represented by the formula (I), n, Ar, A, B, R ¹ , R ² , R ³ , R ⁴ and R ⁵ satisfy any of the following [a] to [f]. is necessary.
[A]
n is 1,
Ar is unsubstituted or biphenyl substituted with two or more halogen, thienyl substituted with phenyl, or naphthyl substituted by unsubstituted or C ₁ -C ₅ alkoxy,
A and B are single bonds,
R ¹ and R ² are hydrogen,
When Ar is biphenyl unsubstituted or substituted with two or more halogens or thienyl substituted with phenyl,
R ³ is hydroxyl
R ⁴ is hydrogen or substituted or unsubstituted C ₁ -C ₅ alkyl,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When Ar is unsubstituted naphthyl,
R ³ is hydroxyl
R ⁴ is a substituted or unsubstituted C ₁ -C ₅ alkyl;
R ⁵ is a carboxylic acid,
Ar is when naphthyl substituted by C ₁ -C ₅ alkoxy,
R ³ is hydroxyl
R ⁴ is hydrogen,
R ⁵ is a carboxylic acid.
[B]
n is 1,
Ar is naphthalen-1-yl,
A is —O—CH ₂ — or —O—,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form vinylene,
R ⁵ is a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When A is -O-CH _2-
B is a single bond or —CH ₂ —;
When A is -O-
B is —CH ₂ —.
[C]
n is 1,
Ar is a naphthyl substituted with 5-phenyl-thien-2-yl, or unsubstituted or C ₁ -C ₅ alkoxy,
When Ar is 5-phenylthien-2-yl,
A and B are single bonds,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form an epoxy,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When Ar is a naphthyl substituted by unsubstituted or C ₁ -C ₅ alkoxy,
A is vinylene,
B is a single bond,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form an epoxy,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[D]
n is 1,
Ar is unsubstituted naphthyl or unsubstituted indolyl;
A and B are single bonds,
R ³ and R ⁴ are hydrogen or together with the carbon atom to which they are attached form vinylidene;
When Ar is unsubstituted naphthyl,
R ¹ and R ² together with the carbon atom to which they are attached form a carbonyl,
R ⁵ is phosphonic acid,
When Ar is an unsubstituted indol,
R ¹ and R ² are hydrogen or together with the carbon atom to which they are attached form a carbonyl,
R ⁵ is a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[E]
n is 1,
Ar is unsubstituted naphthyl,
A is -O-CH _2-
B is a single bond,
R ¹ is hydrogen;
R ² and R ⁴ together with the carbon atom to which they are attached form vinylene,
R ³ is a substituted or unsubstituted C ₁ -C ₅ acylamino;
R ⁵ is a carboxylic acid or an ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[F]
n is 0,
Ar is unsubstituted naphthyl,
A and B are single bonds,
R ¹ and R ² are hydrogen,
R ⁵ is a carboxylic acid ester with N-hydroxyphthalimide.

In the formula (I), when A is —O—CH ₂ —, A is preferably bonded to Ar via O.
When the compound represented by formula (I) satisfies the above [a], Ar is biphenyl substituted with two halogens, thienyl substituted with phenyl, or naphthyl unsubstituted or substituted with methoxy It is preferable.

In the above case, when Ar is biphenyl substituted with 2 halogens or thienyl substituted with phenyl, R ⁴ is preferably hydrogen. R ⁵ is more preferably a carboxylic acid or a methyl ester of carboxylic acid.

In the above case, when Ar is unsubstituted naphthyl, R ⁴ is preferably methyl. R ⁵ is preferably a carboxylic acid.

In the above case, when Ar is naphthyl substituted with methoxy, R ⁴ is preferably hydrogen. R ⁵ is preferably a carboxylic acid.

When the compound represented by the formula (I) satisfies the above [b], R ⁵ is preferably a methyl ester of carboxylic acid.

When the compound represented by the formula (I) satisfies the above [c], Ar is preferably 5-phenylthien-2-yl, or unsubstituted or substituted with methoxy. R ⁵ is preferably a carboxylic acid or a methyl ester of a carboxylic acid.

When the compound represented by formula (I) satisfies the above [d], when Ar is unsubstituted naphthyl, R ³ and R ⁴ are preferably hydrogen.

In the above case, when Ar is an unsubstituted indolyl, R ¹ and R ² are preferably hydrogen. R ³ and R ⁴ are preferably taken together with the carbon atom to which they are attached to form vinylidene. R ⁵ is preferably a methyl ester of carboxylic acid.

When the compound represented by the formula (I) satisfies the above [e], R ³ is preferably acetylamino. R ⁵ is preferably a carboxylic acid or a methyl ester of a carboxylic acid.

  Particularly preferred compounds represented by formula (I) are selected from the group consisting of the following compounds.

  In the present specification, among the compounds represented by the formula (I) or (I ′) described below, a compound group satisfying the above [a] or the following [a ′] is referred to as “lactic acid type compound”, The compound group satisfying [b] or the following [b ′] is “vinyl ether type compound”, the compound group satisfying the above [c] or the following [c ′] is “acrylic acid type compound”, and the above [d] to [f]. Alternatively, a group of compounds satisfying the following [d ′] to [g ′] may be collectively referred to as “other types of compounds”.

  The compound represented by the formula (I) and the compound represented by the formula (I ′) described below includes not only the compound itself but also a salt thereof. The counter ion of the salt of the compound of the present invention is not limited, for example, a cation such as sodium ion, potassium ion, calcium ion or magnesium ion, or chloride ion, bromide ion, formate ion, acetate ion , Maleate ion, fumarate ion, benzoate ion, ascorbate ion, pamoate ion, succinate ion, bismethylenesalicylate ion, methanesulfonate ion, ethanedisulfonate ion, propionate ion, tartrate ion, salicylate ion, Citrate ion, gluconate ion, aspartate ion, stearate ion, palmitate ion, itaconic acid ion, glycolate ion, p-aminobenzoate ion, glutamate ion, benzenesulfonate ion, cyclohexane Silsulfamate ion, methanesulfonate ion, ethanesulfonate ion, isethionate ion, benzenesulfonate ion, p-toluenesulfonate ion, naphthalenesulfonate ion, phosphate ion, nitrate ion, sulfate ion, carbonate ion, carbonate Anions such as hydrogen ions or perchlorate ions are preferred. When the compound of the present invention is in the form of a salt with the counter ion, the compound can be used without substantially reducing the auxin biosynthesis inhibitory activity.

  The compound represented by the formula (I) of the present invention and the compound represented by the formula (I ′) described below include not only the above or the following compounds themselves, but also solvates thereof. Solvents that can form solvates with the compounds of the present invention are not limited and include, for example, methanol, ethanol, 2-propanol (isopropyl alcohol), dimethyl sulfoxide (DMSO), acetic acid, ethanolamine, or ethyl acetate. An organic solvent such as or water is preferred. When the compound of the present invention is in the form of a solvate with the above-mentioned solvent, the compound can be used without substantially reducing the auxin biosynthesis inhibitory activity.

  When the compound of the present invention has one or more stereocenters (chiral centers), the compound represented by the formula (I) of the present invention and the compound represented by the formula (I ′) described below are Also included are the individual enantiomers and diastereomers of the compounds, and mixtures thereof such as racemates.

  By having the above characteristics, the compound represented by the formula (I) can express high auxin biosynthesis inhibitory activity.

で表される化合物又はその塩を有効成分として含むオーキシン生合成阻害剤に関する。 <2. Auxin biosynthesis inhibitor>
The present invention also provides (I ′):

The auxin biosynthesis inhibitor which contains the compound or its salt represented by these as an active ingredient.

In the compound represented by the formula (I ′), n ′, Ar ′, A ′, B ′, R ^{1 ′} , R ^{2 ′} , R ^{3 ′} , R ^{4 ′} and R ^{5 ′} are the following [a ′ ] To [g ′] must be satisfied.
[A ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ and B ′ are single bonds,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{3 ′} is hydroxyl,
R ^{4 ′} is hydrogen or substituted or unsubstituted alkyl;
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[B ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is —O—CH ₂ — or —O—,
B ′ is a single bond or —CH ₂ —;
R ^{1 ′} and R ^{3 ′} are hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form vinylene,
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[C ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond, vinylene or carbonyl,
B ′ is a single bond,
R ^{1 ′} and R ^{3 ′} are hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form an epoxy or vinylene;
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[D ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—CH ₂ —,
B ′ is a single bond,
R ^{1 ′} and R ^{2 ′} are hydrogen or together with the carbon atom to which they are attached form a carbonyl,
R ^{3 ′} and R ^{4 ′} are hydrogen or together with the carbon atom to which they are attached form vinylidene;
R ^{5 ′} is a carboxylic acid or phosphonic acid, or a carboxylic acid or phosphonic acid ester with a substituted or unsubstituted alkyl.
[E ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—CH ₂ —,
B ′ is a single bond,
R ^{1 ′} is hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form vinylene,
R ^{3 ′} is acylamino,
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl, or
R ^{3 ′} and R ^{5 ′} together with the carbon atom to which they are attached form an oxazol-5 (4H) -one ring.
[F ']
n 'is 0,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—,
B ′ is a single bond,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{5 ′} is a carboxylic acid, a carboxylic acid ester with N-hydroxyphthalimide, or a carboxylic acid hydrazide.
[G ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond,
B ′ is a single bond or methylene,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{3 ′} is hydrogen or hydroxyl;
R ^{4 ′} is hydrogen,
R ^{5 ′} is hydroxyl.

In Formula (I ′), when A ′ is —O—CH ₂ —, A ′ is preferably bonded to Ar ′ via O.

In the formula (I ′), Ar ′ is preferably an aryl or heteroaryl which is unsubstituted or substituted by halogen, substituted or unsubstituted alkyl, alkoxy or aryl, and is unsubstituted or halogen, substituted or unsubstituted C ₁ -C ₅ alkyl, more preferably C ₁ -C ₅ alkoxy or aryl or heteroaryl substituted with aryl, one or more halogens, phenyl substituted with methoxy or phenyl, biphenyl, thienyl or naphthyl It is particularly preferred.

When the compound represented by the formula (I ′) satisfies the above [a ′], Ar ′ is preferably selected from the above groups. R ^{4 ′} is preferably hydrogen or substituted or unsubstituted C ₁ -C ₅ alkyl, more preferably hydrogen or methyl. R ^{5 ′} is preferably a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C _{1 to} C ₅ alkyl, and more preferably a carboxylic acid or a methyl ester of a carboxylic acid.

When the compound represented by the formula (I ′) satisfies the above [b ′] or [c ′], Ar ′ is preferably selected from the above groups. R ^{5 ′} is preferably a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C _{1 to} C ₅ alkyl, and more preferably a carboxylic acid or a methyl ester of a carboxylic acid.

When the compound represented by the formula (I ′) satisfies the above [d ′], Ar ′ is preferably selected from the above groups. R ^{5 ′} is preferably a carboxylic acid or phosphonic acid, or a carboxylic acid or phosphonic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl, of carboxylic acid or phosphonic acid, or of carboxylic acid or phosphonic acid. More preferred is methyl or ethyl ester.

When the compound represented by the formula (I ′) satisfies the above [e ′], Ar ′ is preferably selected from the above groups. R ^{3 ′} is preferably a substituted or unsubstituted C ₁ -C ₅ acylamino, more preferably acetylamino. When R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl, the carboxylic acid ester is preferably a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl, A methyl ester of carboxylic acid is more preferable.

When the compound represented by the formula (I ′) satisfies the above [f ′], Ar ′ is preferably selected from the above groups. When A ′ is a single bond, R ^{5 ′} is preferably a carboxylic acid ester or carboxylic acid hydrazide with N-hydroxyphthalimide. When A ′ is —O—, R ^{5 ′} is preferably a carboxylic acid.

Particularly preferred compounds represented by the formula (I ′) are selected from the group consisting of the following compounds.

  The compound represented by the formula (I) or the formula (I ′) of the present invention reduces the amount of endogenous IAA in the plant body and / or grows the plant body (for example, main root or seed root elongation of the young plant body). Can be inhibited. In particular, when the compound represented by the formula (I) or the formula (I ′) is any one of a lactic acid type compound, a vinyl ether type and an acrylic acid type compound, the plant is compared with the auxin biosynthesis inhibitor of the prior art. Not only can the amount of endogenous IAA in the body be significantly reduced, but also the growth of the plant can be markedly inhibited.

  By having the above characteristics, the compound represented by the formula (I ′) can express high auxin biosynthesis inhibitory activity.

  The auxin biosynthesis inhibitor of the present invention contains an agriculturally acceptable carrier and optionally one or more agriculturally acceptable adjuvants in addition to the compound represented by the formula (I ′) as an active ingredient. But you can. In this case, the auxin biosynthesis inhibitor of the present invention is an agricultural product comprising an active ingredient compound represented by formula (I ′), an agriculturally acceptable carrier and one or more agriculturally acceptable adjuvants. Provided as a chemical composition.

  Agriculturally acceptable carriers include water, mineral oil fractions such as kerosene or diesel oil, oils derived from plants or animals, cyclic or aromatic hydrocarbons (eg paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof) Or alkylated benzenes or their derivatives), alcohols (eg methanol, ethanol, propanol, butanol or cyclohexanol), ketones (eg cyclohexanone), amines (eg N-methylpyrrolidone), or mixtures thereof A top acceptable liquid carrier is preferred.

  Agriculturally acceptable adjuvants include, for example, solid carriers, inert adjuvants, surfactants (e.g., dispersants, protective colloids, emulsifiers and wetting agents), organic or inorganic thickeners, fungicides, Antifreeze agents, antifoaming agents or colorants are preferred.

  Auxin is known to exist universally in plants. Therefore, the auxin biosynthesis inhibitor of the present invention can be applied to various plants including angiosperms and gymnosperms. Plants to which the auxin biosynthesis inhibitor of the present invention can be applied include, but are not limited to, for example, cruciferous plants such as Arabidopsis thaliana and rape, gramineous plants such as rice, corn, wheat and barley, soybean Desirable plants (eg, crop plants) such as legumes such as grapes, vines such as grapes, solanaceous plants such as tomatoes, and roses such as peaches and apples. Alternatively, as described below, when the auxin biosynthesis inhibitor of the present invention is used for controlling undesired plants, the plant to which the auxin biosynthesis inhibitor can be applied is not limited, for example, Mention may be made of undesired plants (eg weeds) such as grasses such as Inobie and Tainubie, broad-leaved weeds such as koi and willow, and cyprinaceae weeds such as scorpion and crickets. By applying the auxin biosynthesis inhibitor of the present invention to the plant as described above, it becomes possible to inhibit auxin biosynthesis in the plant body.

  The compound represented by the formula (I) or the formula (I ′) of the present invention has high auxin biosynthesis inhibitory activity. Therefore, the present invention also relates to a method of inhibiting auxin biosynthesis in a plant comprising treating the plant with an auxin biosynthesis inhibitor of the present invention. In the method of the present invention, the plant to be treated with the auxin biosynthesis inhibitor is preferably the above-mentioned desirable plant and / or undesirable plant.

  As used herein, “inhibition of auxin biosynthesis” and “inhibition activity of auxin biosynthesis” mean to inhibit at least one of the enzymatic reactions involved in auxin biosynthesis in plants, or such activity. To do. As already explained, the biosynthetic pathway of indole 3-acetic acid (IAA), the main compound of endogenous auxin in plants, includes a route through L-tryptophan and a route through it (non-tryptophan route). There are two paths. L-AOPP, a known auxin biosynthesis inhibitor, inhibits phenylalanine ammonia lyase (PAL), which is known as the main biosynthesis enzyme of phenylpropanoids. For this reason, L-AOPP can also inhibit the biosynthesis of phenylpropanoid secondary metabolites located downstream of PAL. In contrast, the compounds of the present invention are believed to inhibit enzymatic reactions that catalyze any of the IAA biosynthetic pathways via L-tryptophan. Therefore, the compound of the present invention can specifically reduce the amount of endogenous IAA in a plant without substantially affecting the production of other secondary metabolites.

  The amount of endogenous IAA in the plant can be measured by referring to Soeno et al. (Plant Cell Physiol., 2010, Vol. 51, p. 524-536).

  Auxin is known to be involved in plant development, growth, differentiation and various environmental responses. In addition, it is known that auxin regulates various physiological actions in a plant body in association with other plant hormones such as ethylene, gibberellin, abscisic acid and cytokinin (crosstalk). Therefore, the present invention also relates to a method of regulating the growth of a plant comprising treating the plant with an auxin biosynthesis inhibitor of the present invention. As used herein, “regulate plant growth” means to have some effect on plant growth. Here, the influence given to the growth of a plant includes both the promoting effect and the inhibitory effect on the growth of the plant. The action for regulating the growth of the plant is preferably, for example, a desirable action for promoting the growth of a plant (for example, promoting the growth of root length). Or it is preferable that the effect | action which regulates the growth of the said plant is an effect | action (For example, suppression of leaf fall or fruit fall, aging suppression of a flower bud, or fruit ripening suppression) based on the cross talk of auxin and ethylene. More preferably, the effect of regulating the growth of the plant is to maintain the freshness of the plant, such as suppression of flower senescence or suppression of fruit ripening. In the above case, the plant to be treated with the auxin biosynthesis inhibitor of the present invention is preferably the plant described above, and more preferably the desired plant described above. By treating the desired plant with the auxin biosynthesis inhibitor of the present invention, the growth of the plant can be promoted and / or the freshness of the plant can be maintained.

  The auxin biosynthesis inhibitor of the present invention can inhibit the growth of an undesired plant by inhibiting auxin biosynthesis (eg, inhibition of root elongation, herbicide, death or germination). Therefore, the present invention also relates to a method for herbicidal undesired plants comprising treating the undesired plants with an auxin biosynthesis inhibitor of the present invention. In this case, the auxin biosynthesis inhibitor of the present invention is used to control unwanted plants. In the above case, the plant treated with the auxin biosynthesis inhibitor of the present invention is preferably the undesired plant described above. By treating the undesired plant with the auxin biosynthesis inhibitor of the present invention, it is possible to control the plant by inhibiting the growth of the plant.

  When a plant is treated with the auxin biosynthesis inhibitor of the present invention, the dosage forms and application methods of agricultural chemicals usually used in the art can be used. Suitable dosage forms include, for example, emulsions, wettable powders, liquids, aqueous solvents, powders, powders, pastes and granules. Suitable application methods include, for example, spraying, dusting, spraying, dipping and coating.

  As described above, the auxin biosynthesis inhibitor of the present invention can specifically inhibit auxin biosynthesis in a plant body. Therefore, by treating the plant with the auxin biosynthesis inhibitor of the present invention, it becomes possible to regulate the growth of the plant.

  Hereinafter, the present invention will be described more specifically with reference to examples. However, the technical scope of the present invention is not limited to these examples.

<I: Synthesis of compound>
[I-1: Synthesis of KOK3017]

Methyl 2-hydroxy-3- (6-methoxynaphthalen-2-yl) propanoate (100 mg, 0.384 mmol) was dissolved in methanol (2 ml). To the resulting solution was added 2N aqueous sodium hydroxide solution (1 ml) and the mixture was stirred at room temperature for 4 hours. 2N hydrochloric acid was added to the reaction solution to adjust to pH 1, and the reaction solution was concentrated under reduced pressure. The obtained solid was suspended in water and collected by filtration. The residue collected by filtration was dried under reduced pressure to obtain the title compound (white crystals 87 mg, 92%).
¹ H-NMR (DMSO, 270 MHz) δppm: 2.89 (1H, dd, J = 13.8, 8.2 Hz), 3.10 (1H, dd, J = 13.8, 4.5 Hz), 3.85 (3H, s), 4.19 (1H , dd, J = 8.2, 4.5 Hz), 7.09-7.38 (3H, m), 7.64 (1H, s), 7.72 (1H, d, J = 7.7 Hz), 7.74 (1H, d, J = 8.6 Hz) .

[I-2: Synthesis of KOK3016]

Methyl 2-hydroxy-2-methyl-3- (naphthalen-2-yl) propionate (100 mg, 0.409 mmol) was dissolved in methanol. To the resulting solution was added 2N aqueous sodium hydroxide solution (1 ml) and the mixture was stirred at room temperature for 4 hours. The reaction was concentrated under reduced pressure and adjusted to pH 1 with 2N hydrochloric acid. The precipitated solid was collected by filtration. The residue collected by filtration was dried under reduced pressure to obtain the title compound (white crystals 68 mg, 72%).
¹ H-NMR (DMSO, 270 MHz) δppm: 1.28 (3H, s), 3.00 (1H, d, J = 13.4 Hz), 3.10 (1H, d, J = 13.4 Hz) 7.40-7.50 (3H, m) , 7.70 (1H, s), 7.77-7.87 (3H, m).

[I-3: Synthesis of KOK3096]

  Methyl 3- (4-bromophenyl) -2-hydroxypropionate (500 mg, 1.93 mmol), 3,5-dichlorophenylboronic acid (442 mg, 2.32 mmol), [1,1'-bis (diphenylphosphino) Ferrocene] dichloropalladium (II), dichloromethane adduct (79 mg), potassium carbonate (400 mg, 2.90 mmol) and dioxane (10 ml) were stirred at 150 ° C. for 3 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure and purified directly by silica gel chromatography (hexane: ethyl acetate = 4: 1). This gave the title compound (441 mg, 70% yellow oil).

¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 2.76 (1H, d, J = 5.8 Hz), 3.01 (1H, dd, J = 14.0, 6.9 Hz), 3.19 (1H, dd, J = 14.0, 4.3 Hz), 3.80 (3H, s), 4.45-4.53 (1H, m), 7.27-7.34 (3H, m), 7.43-7.50 (4H, m).

[I-4: Synthesis of KOK3098]

  Tetrahydrofuran (5 ml) was added to sodium hydride (60%) (255 mg, 6.38 mmol) and stirred. To the resulting mixture, a mixture of 5-phenylthiophene-2-carbaldehyde (1.00 g, 5.31 mmol), methyl chloroacetate (692 mg, 6.38 mmol) and tetrahydrofuran (10 ml) was added dropwise, and overnight at room temperature. Stir. The reaction solution was ice-cooled, neutralized with 1 M sulfuric acid, and extracted three times with dichloromethane. A dichloromethane solution of the obtained extract was dried over anhydrous sodium sulfate. The solution was filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane: ethyl acetate = 5: 1) to give the title compound (brown crystals 462 mg, 33%).

¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 3.91 (3H, s), 6.38 (1H, d, J = 1.7 Hz), 6.81 (1H, d, J = 1.7 Hz), 7.22-7.31 (3H, m), 7.33-7.42 (2H, m), 7.60-7.66 (2H, m).

[I-5: Synthesis of KOK3099]

  The title compound was synthesized according to the method described in the literature (Organic Letters, 2003, Vol. 5, No. 24, p. 4665-4668).

KOK3098 (434 mg, 1.67 mmol) and Pd ⁰ -EnCat (registered trademark) (0.4 mmol / g) (208 mg) obtained in the above reaction were dissolved in ethyl acetate (10 ml). Triethylamine (0.92 ml, 6.67 mmol) and formic acid (0.25 ml, 6.67 mmol) were added to the resulting solution. The resulting reaction solution was stirred overnight at room temperature under an argon atmosphere, and then the reaction solution was filtered. The resulting filtrate was concentrated under reduced pressure. Then, the residue was purified by silica gel chromatography (hexane: ethyl acetate = 3: 1) to obtain the title compound (yellow crystals 178 mg, 41%).
¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 3.05-3.35 (3H, m), 3.76 (3H, s), 4.45 (1H, dd, J = 5.8, 4.3 Hz), 6.81 (1H, dt, J = 3.5, 0.8 Hz), 7.11 (1H, d, J = 3.5 Hz), 7.18-7.26 (1H, m), 7.28-7.37 (2H, m), 7.50-7.56 (2H, m).

[I-6: Synthesis of KOK3083]

To a solution of sodium hydride (60%) (105 mg, 2.63 mmol) and THF (6 ml) was added 3- (naphthalen-2-yl) acrylaldehyde (400 mg, 2.120 mmol), methyl chloroacetate (286 mg, A solution of 2.63 mmol) and THF (4 ml) was added dropwise. The resulting solution was stirred at room temperature for 1 day. Water was added to the resulting solution, and the mixture was extracted 3 times with ethyl acetate. The obtained organic phase was washed 3 times with water and then once with saturated brine, and the organic phase was dried over anhydrous sodium sulfate. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain the title compound (yellow crystals 190 mg, 46%).
¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 3.54 (1H, d, J = 1.8 Hz), 3.82 (4H, m), 5.98 (1H, dd, J = 16.0, 8.0 Hz), 6.99 (1H, d, J = 16.0 Hz), 7.42-7.55 (4H, m), 7.72-7.84 (3H, m).

[I-7: Synthesis of KOK2174]

  Potassium carbonate (959 mg, 6.94 mmol) and 1-naphthol (1.00 g, 6.94 mmol) were suspended in acetone (20 ml). The resulting suspension was stirred at 0 ° C. for 15 minutes. While the suspension was stirred at 0 ° C., methyl 4-bromocrotonate (85%) (1.46 g, 6.94 mmol) dissolved in acetone (20 ml) was added dropwise to the suspension and stirred for 2 hours. did. Thereafter, the suspension was returned to room temperature and stirred for 4 hours. The resulting reaction solution was filtered, and the filtrate was concentrated under reduced pressure. Thereafter, diethyl ether was added to the residue, washed with 2N aqueous sodium hydroxide solution and water, and the organic phase was dried over anhydrous sodium sulfate. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. Thereafter, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 4: 1) to obtain the title compound (yellow oily substance 1.257 g, 75%).

¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 3.76 (3H, s), 4.83 (2H, dd, J = 4.0, 2.1 Hz), 6.33 (1H, dt, J = 15.7, 2.1 Hz), 6.74 ( 1H, d, J = 7.6 Hz), 7.18 (1H, dt, J = 15.8, 4.0 Hz), 7.33 (1H, t, J = 7.6 Hz), 7.47-7.50 (3H, m), 7.77-7.81 (1H , m), 8.28-8.31 (1H, m).

[I-8: Synthesis of KOK3024]

Acetone (20 ml) was added to KOK2174 (900 mg, 3.72 mmol) and potassium carbonate (1.027 g, 7.43 mmol). The resulting mixture was refluxed for 8 hours. The reaction was concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 4: 1) to obtain the title compound (cis: colorless oil 274 mg, 30%, trans: yellow oil 27 mg, 3%). .
¹ H-NMR (CDCl ₃ , 270 MHz) δppm (cis): 3.43 (2H, dd, J = 7.1, 1.7 Hz), 3.73 (3H, s), 5.16 (1H, dt, J = 7.1, 6.1 Hz) , 6.69 (1H, dt, J = 6.1, 1.7 Hz), 6.97 (1H, d, J = 7.6 Hz), 7.37 (1H, t, J = 7.6 Hz), 7.48-7.56 (3H, m), 7.79- 7.85 (1H, m), 8.21-8.25 (1H, m).
¹ H-NMR (CDCl ₃ , 270 MHz) δppm (trans): 3.11 (2H, dd, J = 7.8, 1.2 Hz), 3.72 (3H, s), 5.58 (1H, dt, J = 12.2, 7.8 Hz) , 6.69 (1H, dt, J = 12.2, 1.2 Hz), 6.97 (1H, d, J = 7.8 Hz), 7.37 (1H, t, J = 7.8 Hz), 7.45-7.58 (3H, m), 7.76- 7.85 (1H, m), 8.18-8.26 (1H, m).

[I-9: Synthesis of KOK2098]

Under a nitrogen atmosphere, dimethyl (2- (naphthalen-2-yl) -2-oxoethyl) phosphonate (163 mg, 0.586 mmol) was added to dichloromethane (6 ml). Bromotrimethylsilane (0.61 ml, 4.69 mmol) was added dropwise to the resulting mixture. The mixture was then stirred at room temperature for 21 hours. The reaction solution was concentrated by blowing nitrogen gas to the obtained reaction solution. Water and dichloromethane were added to the concentrate. Crystals precipitated by the treatment were collected by filtration. The crystals collected by filtration were dissolved in ethanol. Insoluble matters contained in the obtained solution were filtered, and the filtrate was concentrated under reduced pressure. This gave the title compound (white crystals 97 mg, 66%).
¹ H-NMR (DMSO, 270 MHz) δppm: 3.62 (1H, s), 3.70 (1H, s), 7.59-7.71 (2H, m), 7.98-8.12 (4H, m), 8.71 (1H, s) .

[I-10: Synthesis of KOK2068]

2-Naphthalene acetic acid (300 mg, 1.61 mmol) and N-hydroxyphthalimide (263 mg, 1.61 mmol) were stirred in dioxane (10 ml). WSCI (309 mg, 1.61 mmol) suspended in dioxane (10 ml) was added dropwise to the resulting mixture. The mixture was then stirred for 2 hours. The reaction was concentrated under reduced pressure. Ethyl acetate was added to the resulting residue, washed with water and saturated brine, and the organic phase was dried over anhydrous sodium sulfate. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1) to give the title compound (white crystals 173 mg, 32%).
¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 4.14 (2H, s), 7.43-7.50 (3H, m), 7.68-7.80 (2H, m), 7.82-7.87 (6H, m).

[I-11: Synthesis of KOK3007]

Indole (400 mg, 3.41 mmol) and potassium hydroxide (211 mg, 3.76 mmol) were stirred in dimethyl sulfoxide (5 ml) under ice cooling. To the obtained mixture, methyl 2- (bromomethyl) acrylate (672 mg, 3.76 mmol) was added dropwise. After the dropwise addition, the mixture was returned to room temperature and stirred for 4 days. Ethyl acetate was added to the resulting reaction solution, washed with water and saturated brine, and the organic phase was dried over anhydrous sodium sulfate. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain the title compound (colorless oil, 20%).
¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 3.80 (3H, s), 4.98 (2H, s), 5.15 (1H, s), 6.23 (1H, s), 6.54 (1H, d, J = 3.1 Hz), 7.08-7.27 (4H, m), 7.63 (1H, d, J = 7.5 Hz).

[I-12: Synthesis of KOK1128]

  Under a nitrogen atmosphere, dichloromethane (10 ml) was added to potassium tert-butoxide (345 mg, 3.07 mmol). While stirring the resulting mixture at -70 ° C, a solution of methyl 2- (acetylamino) -dimethylphosphonoacetate (735 mg, 3.07 mmol) in dichloromethane (10 ml) was added dropwise to the mixture. Thereafter, the mixture was stirred at -70 ° C for 45 minutes. To the obtained mixture, a solution of 2- (naphthalen-1-yloxy) acetaldehyde (345 mg, 3.07 mmol) in dichloromethane (10 ml) was added dropwise. Thereafter, the mixture was stirred at −70 ° C. for 2 hours, returned to room temperature, and further stirred for 5 days. Water was added to the obtained reaction solution, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate solution of the extract was dried over anhydrous sodium sulfate. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained crystals were washed while suspended in dichloromethane. Thereafter, the washed crystals were collected by filtration to obtain the title compound (white crystals, 673 mg, 73%).

¹ H-NMR (CDCl ₃ , 270 MHz) δppm: 2.19 (3H, s), 4.83 (3H, s), 4.87 (2H, d, J = 5.6 Hz), 6.80 (1H, d, J = 7.6 Hz) , 6.92 (1H, t, J = 5.6 Hz), 7.20-7.53 (4H, m), 7.75-7.83 (1H, m), 8.22-8.31 (1H, m).

<II: Usage example>
[II-1: Test compound]
In the following use examples, the following test compounds were used.
(1) Lactic acid type compounds: Compounds KOK3017, KOK3016, KOK3096, KOK3099, KOK2052BP, KOK2099, KOK2166, KOK3026, KOK3035, KOK3045 and KOK3033;
(2) Vinyl ether type compounds: Compounds KOK2174, KOK3024cis and KOK3024trans;
(3) Acrylic acid type compounds: Compounds KOK3083, KOK3098, KOK2052BP2, KOK2103, KOK2169BP, KOK2073, KOK3009, KOK3012, KOK3019 and KOK3025;
(4) Other types of compounds: compounds KOK2098, KOK3007, KOK1128, KOK2068, KOK2071, KOK2074, KOK2194, KOK2195, KOK3041, KOK2202, KOK2097, KOK3028 and KOK2140.

[II-2: Quantitative examination of endogenous IAA content]
Arabidopsis thaliana L., Col-0 seeds were sown on a solid medium (1/2 MS medium solidified with 0.8% agar, containing 1.0% sucrose) prepared in a culture plate. The culture plate was left flat and Arabidopsis was cultivated at 22 ° C. for 6 days under continuous white light. The obtained seedlings were cultured with shaking in a liquid medium (1/2 MS medium containing 1.0% sucrose) prepared in a centrifuge tube at 22 ° C. for 24 hours under continuous white light. Next, test compounds (30 μM each) were added to the liquid medium and cultured with shaking at 22 ° C. for 3 hours under continuous white light. Thereafter, seedlings were collected, and the amount of endogenous IAA in the seedlings was quantified. The amount of endogenous IAA was determined using LC-MS / MS according to the method described in Soeno et al. (Plant Cell Physiol., 2010, Vol. 51, p. 524-536). The results are shown in Figure 1.

  As shown in FIG. 1, among the compounds of the present invention, all of the lactic acid type compounds reduced the amount of endogenous IAA in Arabidopsis thaliana. A similar tendency was confirmed with vinyl ether type compounds. On the other hand, some of the acrylic acid type and other types of compounds did not affect the amount of endogenous IAA in Arabidopsis thaliana.

[II-3: Arabidopsis growth test]
Seeds of Arabidopsis thaliana L., Col-0 are sown on a solid medium (containing 1/2 MS medium solidified with 0.8% agar, 1.5% sucrose and 30 μM of each test compound) in a culture plate did. The culture plate was left standing vertically, and Arabidopsis was cultivated at 22 ° C. for 8 days under continuous white light. Thereafter, the morphology of Arabidopsis thaliana was visually observed. In the control group, the same amount of dimethyl sulfoxide (DMSO) was added instead of the test compound. Table 1 shows compounds in which growth inhibition was observed in comparison with the morphology of Arabidopsis seedlings in the control group. In the table, “◎” indicates the test group in which the elongation of the main root was inhibited by 80% or more, and “○” indicates that the elongation of the main root was inhibited by 50% to 80%, compared to the Arabidopsis seedlings in the control group. “△” indicates a test plot where the inhibition of main root elongation was 50% or less, and “*” indicates a test plot where an auxin excess-like form was observed. The forms of the control group and each test group are shown in Figs. 2-1 to 2-9.

  As shown in Table 1, the compound of the present invention showed a remarkable growth inhibitory effect such as suppression of main root elongation and / or cotyledon growth on Arabidopsis seedlings. In addition, the compounds KOK3033, KOK3009, KOK3012, KOK3019, KOK3025, KOK2068, KOK2071, KOK2074, KOK2202 and KOK2140 showed an auxin-excessive growth inhibitory effect such as remarkable elongation suppression of the main root and promotion of lateral root formation.

[II-4: Rice growth test]
Rice (Oryza sativa L., cultivar: Nihonbare) on a solid medium (containing 1/2 MS medium solidified with 0.3% Gelrite, 1.5% sucrose and 100 μM of each test compound) prepared in a culture plate Sowing. The culture plate was left standing vertically, and rice was cultivated at 30 ° C. for 6 days under continuous white light. Thereafter, the morphology of rice was visually observed. In the control group, the same amount of dimethyl sulfoxide (DMSO) was added instead of the test compound. Table 2 shows compounds in which growth inhibition was observed as compared to the morphology of the rice seedlings in the control group. In the table, “◎” indicates the test plot in which seed root elongation was inhibited by 80% or more compared to the control rice seedling, and “◯” indicates seed root elongation inhibited by 50% to 80%. “Δ” indicates a test group in which inhibition of seed root elongation was 50% or less. Moreover, the forms of the control group and each test group are shown in FIGS.

  As shown in Table 2, the compounds of the present invention exhibited a remarkable growth inhibitory effect such as suppression of seed root and / or cotyledon elongation on rice seedlings.

[II-5: Comparison of Auxin Biosynthesis Inhibitory Activity between Compounds of the Present Invention and Prior Art Compounds]
Using the growth test of Arabidopsis thaliana described in the usage example of II-3, the auxin biosynthesis inhibitory activity of the compound of the example of the present invention and the compound of the prior art (Reference Example 1) was compared. The example compounds used were lactic acid type compound KOK3099 and acrylic acid type compound KOK3098, and the compound of Reference Example 1 was compound KOK1169 having an aminooxy group described in Patent Document 2. The structure of compound KOK1169 is shown below.

FIG. 4 shows the results of Arabidopsis thaliana growth tests for the Example compound and the compound of Reference Example 1.
As shown in FIG. 4, in the case of the compound of Reference Example 1, even in the 100 μM treated group, inhibition of main root elongation was about 42% compared to the Arabidopsis seedlings in the control group (compound concentration: 0 μM). On the other hand, in the case of compound KOK3099, which is a lactic acid type example compound, the inhibition of main root elongation reached about 87% in the 10 μM treated group. In the case of compound KOK3098, which is an example compound of the acrylic acid type, the inhibition of main root elongation reached about 64% in the 30 μM treated group. From the above results, it can be seen that the compound of the present invention has higher auxin biosynthesis inhibitory activity than the auxin biosynthesis inhibitors of the prior art such as the compound having an aminooxy group described in Patent Document 2. It is suggested.

Claims (6)

Formula (I):

[Wherein, n, Ar, A, B, R ¹ , R ² , R ³ , R ⁴ and R ⁵ satisfy any of the following [a] to [f]:
[A]
n is 1,
Ar is unsubstituted or biphenyl substituted with two or more halogen, thienyl substituted with phenyl, or naphthyl substituted by unsubstituted or C ₁ -C ₅ alkoxy,
A and B are single bonds,
R ¹ and R ² are hydrogen,
When Ar is biphenyl unsubstituted or substituted with two or more halogens or thienyl substituted with phenyl,
R ³ is hydroxyl
R ⁴ is hydrogen or substituted or unsubstituted C ₁ -C ₅ alkyl,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When Ar is unsubstituted naphthyl,
R ³ is hydroxyl
R ⁴ is a substituted or unsubstituted C ₁ -C ₅ alkyl;
R ⁵ is a carboxylic acid,
Ar is when naphthyl substituted by C ₁ -C ₅ alkoxy,
R ³ is hydroxyl
R ⁴ is hydrogen,
R ⁵ is a carboxylic acid.
[B]
n is 1,
Ar is naphthalen-1-yl,
A is —O—CH ₂ — or —O—,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form vinylene,
R ⁵ is a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When A is -O-CH _2-
B is a single bond or —CH ₂ —;
When A is -O-
B is —CH ₂ —.
[C]
n is 1,
Ar is a naphthyl substituted with 5-phenyl-thien-2-yl, or unsubstituted or C ₁ -C ₅ alkoxy,
When Ar is 5-phenylthien-2-yl,
A and B are single bonds,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form an epoxy,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl,
When Ar is a naphthyl substituted by unsubstituted or C ₁ -C ₅ alkoxy,
A is vinylene,
B is a single bond,
R ¹ and R ³ are hydrogen,
R ² and R ⁴ together with the carbon atom to which they are attached form an epoxy,
R ⁵ is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[D]
n is 1,
Ar is unsubstituted naphthyl or unsubstituted indolyl;
A and B are single bonds,
R ³ and R ⁴ are hydrogen or together with the carbon atom to which they are attached form vinylidene;
When Ar is unsubstituted naphthyl,
R ¹ and R ² together with the carbon atom to which they are attached form a carbonyl,
R ⁵ is phosphonic acid,
When Ar is an unsubstituted indol,
R ¹ and R ² are hydrogen or together with the carbon atom to which they are attached form a carbonyl,
R ⁵ is a carboxylic acid ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[E]
n is 1,
Ar is unsubstituted naphthyl,
A is -O-CH _2-
B is a single bond,
R ¹ is hydrogen;
R ² and R ⁴ together with the carbon atom to which they are attached form vinylene,
R ³ is a substituted or unsubstituted C ₁ -C ₅ acylamino;
R ⁵ is a carboxylic acid or an ester with a substituted or unsubstituted C ₁ -C ₅ alkyl.
[F]
n is 0,
Ar is unsubstituted naphthyl,
A and B are single bonds,
R ¹ and R ² are hydrogen,
R ⁵ is a carboxylic acid ester with N-hydroxyphthalimide. ]
Or a salt thereof. Formula (I '):

[Wherein, n ′, Ar ′, A ′, B ′, R ^{1 ′} , R ^{2 ′} , R ^{3 ′} , R ^{4 ′} and R ^{5 ′} are any of the following [a ′] to [g ′]. Satisfy:
[A ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ and B ′ are single bonds,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{3 ′} is hydroxyl,
R ^{4 ′} is hydrogen or substituted or unsubstituted alkyl;
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[B ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is —O—CH ₂ — or —O—,
B ′ is a single bond or —CH ₂ —;
R ^{1 ′} and R ^{3 ′} are hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form vinylene,
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[C ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond, vinylene or carbonyl,
B ′ is a single bond,
R ^{1 ′} and R ^{3 ′} are hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form an epoxy or vinylene;
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl.
[D ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—CH ₂ —,
B ′ is a single bond,
R ^{1 ′} and R ^{2 ′} are hydrogen or together with the carbon atom to which they are attached form a carbonyl,
R ^{3 ′} and R ^{4 ′} are hydrogen or together with the carbon atom to which they are attached form vinylidene;
R ^{5 ′} is a carboxylic acid or phosphonic acid, or a carboxylic acid or phosphonic acid ester with a substituted or unsubstituted alkyl.
[E ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—CH ₂ —,
B ′ is a single bond,
R ^{1 ′} is hydrogen,
R ^{2 ′} and R ^{4 ′} together with the carbon atom to which they are attached form vinylene,
R ^{3 ′} is acylamino,
R ^{5 ′} is a carboxylic acid or a carboxylic acid ester with a substituted or unsubstituted alkyl, or
R ^{3 ′} and R ^{5 ′} together with the carbon atom to which they are attached form an oxazol-5 (4H) -one ring.
[F ']
n 'is 0,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond or —O—,
B ′ is a single bond,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{5 ′} is a carboxylic acid, a carboxylic acid ester with N-hydroxyphthalimide, or a carboxylic acid hydrazide.
[G ']
n ′ is 1,
Ar ′ is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
A ′ is a single bond,
B ′ is a single bond or methylene,
R ^{1 ′} and R ^{2 ′} are hydrogen,
R ^{3 ′} is hydrogen or hydroxyl;
R ^{4 ′} is hydrogen,
R ^{5 ′} is hydroxyl. ]
An auxin biosynthesis inhibitor comprising a compound represented by the formula:   The auxin biosynthesis inhibitor according to claim 2, which is used for controlling undesired plants.   A method for inhibiting auxin biosynthesis in a plant, comprising treating the plant with the auxin biosynthesis inhibitor according to claim 2.   A method of regulating the growth of a plant comprising treating the plant with an auxin biosynthesis inhibitor according to claim 2.   A method of weeding an undesirable plant comprising treating the undesirable plant with the auxin biosynthesis inhibitor according to claim 2.

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