JP2008115084A - Phenethylamide compound and plant blight controlling agent containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having a plant blight controlling effect and a plant blight controlling agent containing the compound. <P>SOLUTION: The invention provides a phenethylamide compound expressed by formula (I) and a plant blight controlling agent containing the compound as an active component. In the formula; A is an aromatic cyclic group which may contain a hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom, wherein the aromatic cyclic group may be substituted with R<SP>1</SP>at a site adjacent to the site bonding to the carbonyl group of formula (I) and further may be substituted with a 1-4C alkyl group which may be substituted with a halogen atom, and/or with a halogen atom; and R<SP>1</SP>is a 1-4C alkyl group which may be substituted with a halogen atom, or a halogen atom. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a phenethylamide compound and a plant disease control agent containing the same.

Conventionally, search for compounds for controlling plant diseases has been widely promoted, and some compounds having plant disease control efficacy have been put to practical use.
Moreover, a certain kind of phenethylamide derivative (refer patent document 1) is known.

Japanese Patent Laid-Open No. 9-165374

  An object of the present invention is to provide a compound having an excellent plant disease control effect.

〔式中、Ａは酸素原子、窒素原子及び硫黄原子からなる群より選ばれるヘテロ原子を有していてもよい芳香族環式基を表し、該芳香族環式基は式(I)におけるカルボニル基と結合する位置に隣接する位置がＲ¹で置換され、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基及び／又はハロゲン原子で更に置換されていてもよい。Ｒ¹はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基又はハロゲン原子を表す。〕
で示されるフェネチルアミド化合物（以下、本発明化合物と記す。）及びそれを有効成分として含有する農園芸用殺菌剤を提供する。 As a result of intensive studies, the present inventors have found that the phenethylamide compound represented by the formula (I) has an excellent plant disease control effect, and have reached the present invention. That is, the present invention provides a compound of formula (I)

[In the formula, A represents an aromatic cyclic group which may have a hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom, and the aromatic cyclic group is a carbonyl group in the formula (I). The position adjacent to the position bonded to the group is substituted with R ¹ and may be further substituted with a C1-C4 alkyl group which may be substituted with a halogen atom and / or a halogen atom. R ¹ represents a C1-C4 alkyl group which may be substituted with a halogen atom or a halogen atom. ]
And a fungicide for agricultural and horticultural use containing it as an active ingredient.

  Since the compound of the present invention has an excellent plant disease control effect, it is useful as an active ingredient of a plant disease control agent.

〔Ｒ¹は前記と同じ意味を表し、Ｒ²はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基を表し、Ｒ³はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、ハロゲン原子又は水素原子を表し、Ｒ⁴はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、ハロゲン原子又は水素原子を表す。〕
で示される基が挙げられる。
Ａ１〜Ａ７における、
Ｒ¹で示されるハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基としては、メチル基、ジフルオロメチル基、トリフルオロメチル基などが挙げられ、
Ｒ¹で示されるハロゲン原子は、フッ素原子、塩素原子、臭素原子又はヨウ素原子であり、
Ｒ²で示されるハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基としては、メチル基などが挙げられ、
Ｒ³で示されるハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基としては、メチル基、ジフルオロメチル基、トリフルオロメチル基などが挙げられ、
Ｒ³で示されるハロゲン原子は、フッ素原子、塩素原子、臭素原子又はヨウ素原子であり、
Ｒ⁴で示されるハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基としては、メチル基、ジフルオロメチル基、トリフルオロメチル基などが挙げられ、
Ｒ⁴で示されるハロゲン原子は、フッ素原子、塩素原子、臭素原子又はヨウ素原子である。
本発明において、Ａとして好ましくは、Ａ１、Ａ２、Ａ３又はＡ４で示されるいずれかの基であり、
Ｒ¹として好ましくは、塩素原子、メチル基又はトリフルオロメチル基であり、
Ｒ²として好ましくは、メチル基であり、
Ｒ³として好ましくは、水素原子、塩素原子又はメチル基であり、
Ｒ⁴として好ましくは、水素原子又はメチル基である。 In the present invention, the aromatic cyclic group optionally having a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom represented by A is at a position bonded to the carbonyl group in the formula (I). The adjacent position may be further substituted with a C1-C4 alkyl group and / or a halogen atom which may be substituted with R ¹ and optionally substituted with a halogen atom. Examples of such aromatic cyclic groups include a phenyl group substituted with R ¹ at the 2-position, a pyridyl-3-yl group substituted with R ¹ at the 2-position, and a pyrazol substituted with R ¹ at the 3-position. --4-yl group, 2-position is substituted by R ¹ is 3-furanyl, 2-position is substituted with R ¹ 3-thienyl group, 5-position has been oxazol-4-yl substituted by R ¹ A thiazol-4-yl group substituted with R ¹ at the 5-position (provided that the aromatic cyclic group is further substituted with a halogen atom or a C1-C4 alkyl group optionally substituted with a halogen atom) Or a 5- or 6-membered monocyclic aromatic cyclic group.
More specifically, the aromatic cyclic group represented by A is A1 to A7.

[R ¹ represents the same meaning as described above, R ² represents a C1-C4 alkyl group optionally substituted with a halogen atom, R ³ represents a C1-C4 alkyl group optionally substituted with a halogen atom, halogen Represents an atom or a hydrogen atom, and R ⁴ represents a C1-C4 alkyl group, a halogen atom or a hydrogen atom which may be substituted with a halogen atom. ]
The group shown by these is mentioned.
In A1 to A7,
Examples of the C1-C4 alkyl group optionally substituted with a halogen atom represented by R ¹ include a methyl group, a difluoromethyl group, a trifluoromethyl group, and the like.
The halogen atom represented by R ¹ is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,
Examples of the C1-C4 alkyl group which may be substituted with a halogen atom represented by R ² include a methyl group.
Examples of the C1-C4 alkyl group optionally substituted with a halogen atom represented by R ³ include a methyl group, a difluoromethyl group, a trifluoromethyl group, and the like.
The halogen atom represented by R ³ is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,
Examples of the C1-C4 alkyl group optionally substituted with a halogen atom represented by R ⁴ include a methyl group, a difluoromethyl group, a trifluoromethyl group, and the like.
The halogen atom represented by R ⁴ is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
In the present invention, A is preferably any group represented by A1, A2, A3 or A4,
R ¹ is preferably a chlorine atom, a methyl group or a trifluoromethyl group,
R ² is preferably a methyl group,
R ³ is preferably a hydrogen atom, a chlorine atom or a methyl group,
R ⁴ is preferably a hydrogen atom or a methyl group.

Examples of the compound of the present invention include the following compounds.
In the formula (I), A is an aromatic cyclic group which may have a hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom, and the aromatic cyclic group is represented by the formula (I) The position adjacent to the position bonded to the carbonyl group in is substituted with a trifluoromethyl group or a chlorine atom, and may be further substituted with a C1-C4 alkyl group and / or a halogen atom which may be substituted with a halogen atom. Phenethylamide compound.
A phenethylamide compound wherein A is a group represented by A1 in the formula (I).
A phenethylamide compound wherein A is a group represented by A2 in formula (I).
A phenethylamide compound wherein A is a group represented by A3 in formula (I).
A phenethylamide compound wherein A is a group represented by A4 in the formula (I).
A phenethylamide compound wherein A is a group represented by A5 in the formula (I).
A phenethylamide compound wherein A is a group represented by A6 in the formula (I).
A phenethylamide compound wherein A is a group represented by A7 in the formula (I).
A phenethyl amide compound represented by the formula (I), wherein A is a group represented by A1, and R ¹ is a trifluoromethyl group or a chlorine atom.
A phenethylamide compound represented by formula (I), wherein A is a group represented by A2, and R ¹ is a trifluoromethyl group or a chlorine atom.
A phenethyl amide compound represented by the formula (I), wherein A is a group represented by A3, and R ¹ is a trifluoromethyl group or a chlorine atom.
A phenethyl amide compound represented by the formula (I), wherein A is a group represented by A4, and R ¹ is a trifluoromethyl group or a chlorine atom.
A phenethyl amide compound represented by the formula (I), wherein A is a group represented by A5, and R ¹ is a trifluoromethyl group or a chlorine atom.
A phenethyl amide compound represented by the formula (I), wherein A is a group represented by A6, and R ¹ is a trifluoromethyl group or a chlorine atom.
A phenethylamide compound represented by the formula (I), wherein A is a group represented by A7, and R ¹ is a trifluoromethyl group or a chlorine atom.
In the formula (I), A represents 2-trifluoromethylphenyl group, 1-methyl-3-trifluoromethylpyrazol-4-yl group, 5-methyl-2-trifluoromethylfuran-3-yl group, 2- A phenethylamide compound which is a chloropyridin-3-yl group or a 3-chloro-1,5-dimethylpyrazol-4-yl group.

  The compound of the present invention can be produced, for example, according to the following [Production Method A] or [Production Method B]. In these production methods, a protecting group can be used as necessary to protect the functional group from the reaction.

〔式中、Ａは前記と同じ意味を表し、Ｌ¹は塩素原子等の脱離基を表す。〕
反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常０．２〜２４時間の範囲である。
式（II）で示される化合物１モルに対して、式（III）で示される化合物は通常０．２〜５モル、塩基は通常１〜１０モルの量比で使用される。使用される塩基としては、例えば水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム炭酸カルシウム、水素化ナトリウム等の無機塩基、カリウムｔ−ブトキシド、ナトリウムメトキド、ナトリウムエトキシド等のアルカリ金属アルコキシド類、ピリジン、トリエチルアミン、エチルジイソプロピルアミン、アニリン等の有機塩基、あるいは、これらの混合物があげられる。
該反応は通常、溶媒中にて行われる。溶媒としては、例えば、テトラヒドロフラン、エチレングリコ−ルジメチルエ−テル、ｔ−ブチルメチルエ−テル等のエ−テル溶媒、ｎ−ヘキサン、ｎ−ヘプタン等の脂肪族炭化水素溶媒、トルエン等の芳香族炭化水素溶媒、モノクロロベンゼン等のハロゲン化炭化水素溶媒、ピリジン、トリエチルアミン、Ｎ，Ｎ−ジメチルアニリン等の有機塩基溶媒、酢酸ブチル、酢酸エチル等のエステル溶媒、アセトニトリル等のニトリル溶媒、水、あるいはそれらの混合物があげられる。
反応終了後、反応混合物を水に注加し、有機溶媒抽出、濃縮等の通常の後処理を行い、目的化合物を得ることができる。必要に応じて再結晶、蒸留、クロマトグラフィ−等により、目的化合物を精製することができる。 [Production method A]
A process for producing a compound of the present invention, in which a compound represented by the formula (II) and a compound represented by the formula (III) are reacted in the presence of a base.

[Wherein, A represents the same meaning as described above, and L ¹ represents a leaving group such as a chlorine atom. ]
The reaction temperature is usually in the range of −20 to 100 ° C., and the reaction time is usually in the range of 0.2 to 24 hours.
The compound represented by the formula (III) is usually used in an amount of 0.2 to 5 mol and the base is usually used in an amount of 1 to 10 mol with respect to 1 mol of the compound represented by the formula (II). Examples of the base used include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate calcium carbonate and sodium hydride, and alkali metal alkoxides such as potassium t-butoxide, sodium methoxide and sodium ethoxide. , Organic bases such as pyridine, triethylamine, ethyldiisopropylamine, aniline, or a mixture thereof.
The reaction is usually performed in a solvent. Examples of the solvent include ether solvents such as tetrahydrofuran, ethylene glycol dimethyl ether, and t-butyl methyl ether, aliphatic hydrocarbon solvents such as n-hexane and n-heptane, and aromatic hydrocarbon solvents such as toluene. Halogenated hydrocarbon solvents such as monochlorobenzene, organic base solvents such as pyridine, triethylamine and N, N-dimethylaniline, ester solvents such as butyl acetate and ethyl acetate, nitrile solvents such as acetonitrile, water, or a mixture thereof. can give.
After completion of the reaction, the reaction mixture is poured into water and subjected to usual post-treatments such as organic solvent extraction and concentration, whereby the target compound can be obtained. If necessary, the target compound can be purified by recrystallization, distillation, chromatography or the like.

〔式中、Ａは前記と同じ意味を表す。〕
反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常０．２〜２４時間の範囲である。
式（IV）で示される化合物１モルに対して、式（III）で示される化合物は通常０．２〜５モル、縮合剤は通常１〜１０モルの量比で使用される。使用される縮合剤としては、ジカルボキシイミド、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド等が挙げられる。
該反応は通常、溶媒中にて行われる。溶媒としては、例えば、テトラヒドロフラン、エチレングリコ−ルジメチルエ−テル、ｔ−ブチルメチルエ−テル等のエ−テル溶媒、ｎ−ヘキサン、ｎ−ヘプタン等の脂肪族炭化水素溶媒、トルエン等の芳香族炭化水素溶媒、モノクロロベンゼン等のハロゲン化炭化水素溶媒、ピリジン、トリエチルアミン、Ｎ，Ｎ−ジメチルアニリン等の有機塩基溶媒、酢酸ブチル、酢酸エチル等のエステル溶媒、アセトニトリル等のニトリル溶媒、あるいはそれらの混合物があげられる。
反応終了後、反応混合物を水に注加し、有機溶媒抽出、濃縮等の通常の後処理を行い、目的化合物を得ることができる。必要に応じて再結晶、蒸留、クロマトグラフィ−等により、目的化合物を精製することができる。 [Production method B]
A process for producing a compound of the present invention, in which a compound represented by formula (IV) and a compound represented by formula (III) are reacted in the presence of a condensing agent.

[Wherein, A represents the same meaning as described above. ]
The reaction temperature is usually in the range of −20 to 100 ° C., and the reaction time is usually in the range of 0.2 to 24 hours.
The compound represented by the formula (III) is usually used in an amount of 0.2 to 5 mol and the condensing agent is usually used in an amount of 1 to 10 mol based on 1 mol of the compound represented by the formula (IV). Examples of the condensing agent used include dicarboximide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.
The reaction is usually performed in a solvent. Examples of the solvent include ether solvents such as tetrahydrofuran, ethylene glycol dimethyl ether, and t-butyl methyl ether, aliphatic hydrocarbon solvents such as n-hexane and n-heptane, and aromatic hydrocarbon solvents such as toluene. , Halogenated hydrocarbon solvents such as monochlorobenzene, organic base solvents such as pyridine, triethylamine, N, N-dimethylaniline, ester solvents such as butyl acetate and ethyl acetate, nitrile solvents such as acetonitrile, or mixtures thereof. .
After completion of the reaction, the reaction mixture is poured into water and subjected to usual post-treatments such as organic solvent extraction and concentration, whereby the target compound can be obtained. If necessary, the target compound can be purified by recrystallization, distillation, chromatography or the like.

  The compound represented by the formula (II) and the compound represented by the formula (IV) are commercially available or known methods, for example, the method described in International Patent Application Publication No. WO93 / 11117, European Patent Application Publication Specification Those produced by the method described in EP-A-0545099 or the method described in EP-A-0589301 can be used.

〔式中のＲ¹は表１に記載の置換基である。〕
で示される化合物；
式（ii）

〔式中のＲ¹は表１に記載の置換基である。〕；
で示される化合物； Hereinafter, although the specific example of this invention compound is shown, this invention compound is not limited to these examples. (Hereinafter, Me in the table represents a methyl group.)
Formula (i)

[R ¹ in the formula is a substituent described in Table 1. ]
A compound represented by:
Formula (ii)

[R ¹ in the formula is a substituent described in Table 1. ];
A compound represented by:

〔式中のＲ¹、Ｒ²及びＲ³は表２に記載の置換基である。〕
で示される化合物； Formula (iii)

[R ¹ , R ² and R ³ in the formula are the substituents described in Table 2. ]
A compound represented by:

〔式中のＲ¹、Ｒ³及びＲ⁴は表３に記載の置換基である。〕
で示される化合物；
式（v）

〔式中のＲ¹、Ｒ³及びＲ⁴は表３に記載の置換基である。〕
で示される化合物； Formula (iv)

[R ¹ , R ³ and R ⁴ in the formula are the substituents described in Table 3. ]
A compound represented by:
Formula (v)

[R ¹ , R ³ and R ⁴ in the formula are the substituents described in Table 3. ]
A compound represented by:

〔式中のＲ¹及びＲ⁴は表４に記載の置換基である。〕
で示される化合物；
式（vii）

〔式中のＲ¹及びＲ⁴は表４に記載の置換基である。〕
で示される化合物。 Formula (vi)

[R ¹ and R ⁴ in the formula are the substituents described in Table 4. ]
A compound represented by:
Formula (vii)

[R ¹ and R ⁴ in the formula are the substituents described in Table 4. ]
A compound represented by

  The plant disease control agent of the present invention may be the compound of the present invention itself, but usually mixed with a solid carrier, a liquid carrier, a surfactant, and other adjuvants for formulation, emulsion, wettable powder, granule Used in wettable powders, emulsion preparations, flowable preparations, powders, granules and the like. These preparations usually contain 0.1 to 90% by weight of the compound of the present invention as an active ingredient.

  Examples of solid carriers used in the formulation include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite and other minerals, corn cob flour, walnut Examples include natural organic substances such as shell powder, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and fine powders or granular materials such as synthetic inorganic substances such as synthetic silicon hydroxide. Examples of liquid carriers include xylene, Aromatic hydrocarbons such as alkylbenzene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, propylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, petroleum aliphatic hydrocarbons , Esters, di Sulfoxide, acetonitrile, water and the like.

  Surfactants include, for example, alkyl sulfates, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphates, lignin sulfonates, naphthalene sulfonate formalin condensates, and the like. Nonionic surfactants such as ionic surfactants, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like can be mentioned.

  Other formulation adjuvants include, for example, water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and its salts, polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum, aluminum magnesium silicate, alumina sol and the like. Examples include inorganic substances, preservatives, colorants, PAP (isopropyl acid phosphate), and stabilizers such as BHT.

  The plant disease control agent of the present invention is used, for example, to protect the plant from plant diseases by treating the plant body with foliage, and from the plant diseases, the plant growing in the soil by treating the soil. Used to protect.

When the plant disease control agent of the present invention is used by treating the plant body with foliage treatment or by treating it with soil, the treatment amount depends on the type of crop, the type of disease to be controlled, and the control type. Although it can be changed depending on the degree of occurrence of the target disease, preparation form, treatment time, weather conditions, etc., it is usually 1 to 5000 g, preferably 5 to 1000 g as the compound of the present invention per 10,000 m ² .

  Emulsions, wettable powders and flowables are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is usually 0.0001 to 3% by weight, preferably 0.0005 to 1% by weight. Powders, granules, etc. are usually processed without dilution.

  Moreover, the plant disease control agent of this invention can also be used by processing methods, such as seed disinfection. Examples of the method for seed disinfection include a method of immersing a plant seed in a plant disease control agent of the present invention prepared so that the concentration of the compound of the present invention is 1 to 1000 ppm, and the concentration of the compound of the present invention in a plant seed. Examples thereof include a method of spraying or smearing the plant disease control agent of the present invention in an amount of 1 to 1000 ppm and a method of dressing the plant disease control agent of the present invention formulated into a powder on plant seeds.

  In the plant disease control method of the present invention, the effective amount of the plant disease control agent of the present invention is usually treated on the plant where the occurrence of the disease is predicted or the soil where the plant grows, and / or the occurrence of the disease is confirmed. It is carried out by treating the applied plant or the soil on which the plant grows.

The compound of the present invention can be used as a plant disease control agent for fields, paddy fields, orchards, tea gardens, pastures, lawns, etc., and is used in combination with other agricultural and horticultural fungicides to enhance the control effect. Can be expected. Examples of other agricultural and horticultural fungicides that can be mixed include:
Propiconazole, triazimenol, prochloraz, penconazole, tebuconazole, flusilazole, dinicoazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, microbutanyl, fenbuconazole, Azole fungicides such as hexaconazole, fluquinconazole, triticonazole, viteltanol, imazalyl and flutriahol,
Cyclic amine fungicidal compounds such as fenpropimorph, tridemorph and fenpropidin,
Benzimidazole fungicides such as carbendazim, benomyl, thiabendazole, thiophanate methyl,
Procymidone, cyprodinyl, pyrimethanil, dietofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, captan, mepanipyrim, fenpiclonyl, fludioxonil, diclofluanid, phorpetre, cresoxime methyl, azoxystrobin, trifloxystrobin, trixoxystrobin Robin, dimoxystrobin, spiroxamine, quinoxyphene, fenhexamide, famoxadone, fenamidone, iprovaricarb and the like.

  The compound of the present invention can be mixed or used in combination with agricultural and horticultural insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers and the like.

Examples of plant diseases that can be controlled with the compounds of the present invention include the following diseases.
Rice blast (Piculararia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani);
Wheat powdery mildew (Erysiphe graminis), red mold disease (Gibberella zeae), rust disease (Puccinia striformis, P. graminis, P. recondita, P. hordei), snow rot (Typ.n. Bare scab (Ustilago tritici, U. nuda), Tuna scab (Tilletia caries), eye spot disease (Pseudocercosporella herpotrichoides), cloud symptom (Rhynchosporitium leaf disease) ;
Citrus black spot (Diaporthe citri), scab (Elsinoe fawceti), fruit rot (Penicillium digitatum, P. italicum);
Apple Moniria disease (Sclerotinia mali), rot (Valsa mali), powdery mildew (Podosphaera leukotricha), spotted leaf disease (Alternaria maria), scab (Venturia inaequalis)
Pear black spot (Venturia nashicola, V. pirina), black spot (Alternaria kikuchiana), red spot (Gymnosporium haraeanum);
Peach blight (Sclerotinia cinerea), black scab (Cladosporium carpophilum), Phomopsis spoilage (Phomopsis sp.);
Grapes' black rot (Elsinoe ampelina), late rot (Glomerella singulata), powdery mildew (Uncinula nelopetor), rust (Phakopsora amplopidis), black lot's disease (Guignardia pendillosis)
Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae);
Colletotrichum lagenarium, powdery mildew (Sphaerotheca furiginea), vine blight (Mycosphaerella meloniis), tsuba disease (Fusium oxysporum), pori (pse disease) Seedling blight (Pythium sp.);
Tomato ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
Eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoacearum);
Brassicaceae vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae);
Leek rust (Puccinia allii);
Soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), sunspot (Diaporthe phaseolum var. Sojae);
Colletotrichum lindemthianum;
Peanut black astringency (Cercospora personata), brown spot (Cercospora arachidicola);
Pea powdery mildew (Erysiphe pisi);
Potato summer blight (Alternaria solani), Phytophthora infestans;
Strawberry powdery mildew (Sphaerotheca humuli);
Chamochi rice blast (Exobasidium reticulatum), white scab (Elsinoe leucospila);
Tobacco red streak (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophathorophora)
Sugar beet brown spot (Cercospora beticola);
Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
Chrysanthemum brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);
Various crops of gray mold (Botrytis cinerea), sclerotia (Sclerotinia sclerotiorum);
Lawn grass spot disease (Sclerotinia homoeocarpa), Brown patch disease (Rhizotonia solani).

The compound of the present invention can be used as a plant disease control agent in agricultural land or the like where the following crops are cultivated.
"produce":
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Bridegroom,
Foliage plant,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees; tea, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, fir tree, Tsuga, rat, pine, Spruce, yew) etc.

The above “crop” has resistance to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, herbicides such as bromoxynil, This includes crops granted by classical breeding methods or genetic engineering techniques.
Examples of crops to which tolerance has been imparted by a classic breeding method include imidazolinone-based herbicide-resistant Clearfield (registered trademark) canola, sulfonylurea-type ALS-inhibiting herbicide-resistant STS soybeans such as imazetapil Etc.
Examples of crops to which tolerance has been imparted by genetic recombination techniques include glyphosate and glufosinate-resistant maize varieties that have already been sold under trade names such as Roundup Ready (registered trademark) and LibertyLink (registered trademark). Yes.

The above “crop” includes, for example, crops that can synthesize selective toxins known in the genus Bacillus using genetic recombination techniques.
Toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popirie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Insecticidal proteins such as δ-endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; toxins produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin; Plant lectin; agglutinin; trypsin inhibitor, serine protease inhibitor, protease inhibitor such as patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, briodin, etc. Zome inactivating protein (RIP); steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
Further, as toxins expressed in such genetically modified crops, hybrids of insecticidal proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, and the like, delta-endotoxin proteins such as VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073 and the like. Has been.
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.

  Also, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available. Examples of these transgenic plants include YieldGard® (a corn variety that expresses Cry1Ab toxin), YieldGard Rootworm® (a corn variety that expresses Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1) Corn varieties expressing toxin), Herculex I® (corn varieties expressing phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B® (Cotton variety expressing Cry1Ac toxin), Bollgard I (registered trademark) (cotton variety expressing Cry1Ac toxin), Bollgard II (registered trademark) (Cry1Ac and C cotton varieties expressing y2Ab toxin), VIPCOT® (cotton varieties expressing VIP toxin), NewLeaf® (potato varieties expressing Cry3A toxin), NatureGard® Agrisure® Examples include GT Advantage (GA21 glyphosate resistant trait), Agurisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

The above “crop” includes those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
As examples of anti-pathogenic substances, PR proteins and the like are known (PRPs, EP-A-0392225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.
Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.). Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (referred to as plant disease resistance gene, WO 03/000906)) and the like, and the like, and the like, which are produced by microorganisms.

  Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, and a test example, this invention is not limited only to these examples.

About manufacture of this invention compound, it shows in a manufacture example. Unless otherwise specified, the reaction was performed in a nitrogen atmosphere, and the measurement of ¹ H-NMR was performed using tetramethylsilane (TMS) as an internal standard (0 [ppm]).
First, the manufacture example of this invention compound is shown below.

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ（ｐｐｍ）：３．０６（２Ｈ，ｔ），３．７２（２Ｈ，ｑ），５．８２（１Ｈ，ｂｒ ｓ），７．１９−７．２４（２Ｈ，ｍ），７．３９（１Ｈ，ｄ），７．４６−７．６０（３Ｈ，ｍ），７．７０（１Ｈ，ｄ）． Production Example 1
A mixture of 0.20 g of 2- (2,4-dichlorophenyl) ethylamine, 0.12 g of triethylamine and 5 ml of tetrahydrofuran was stirred under ice-cooling, and a mixture of 0.21 g of 2-trifluoromethylbenzoic acid chloride and 1 ml of tetrahydrofuran was added. It was dripped. After 15 minutes, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained crystals were washed with hexane to obtain 0.30 g of N- {2- (2,4-dichlorophenyl) ethyl} -2-trifluoromethylbenzamide (present compound 1).

¹ H-NMR (CDCl ₃ ) δ (ppm): 3.06 (2H, t), 3.72 (2H, q), 5.82 (1H, br s), 7.19-7.24 (2H M), 7.39 (1H, d), 7.46-7.60 (3H, m), 7.70 (1H, d).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ（ｐｐｍ）：３．０９（２Ｈ，ｔ，Ｊ＝７．０Ｈｚ），３．７６（２Ｈ，ｑ，Ｊ＝６．７Ｈｚ），６．５４（１Ｈ，ｂｒ ｓ），７．１９−７．２６（２Ｈ，ｍ），７．３４（１Ｈ，ｄｄ，Ｊ＝７．７Ｈｚ，４．８Ｈｚ），７．４０（１Ｈ，ｄ，Ｊ＝１．７Ｈｚ），８．０８（１Ｈ，ｄｄ，Ｊ＝７．６Ｈｚ，２．０Ｈｚ），８．４６（１Ｈ，ｄｄ，Ｊ＝４．８Ｈｚ，２．１Ｈｚ）． The following compound was obtained according to the method described in Production Example 1 using 2-chloronicotinic acid chloride instead of 2-trifluoromethylbenzoic acid chloride.
N- {2- (2,4-dichlorophenyl) ethyl} -2-chloronicotinamide (present compound 2)

¹ H-NMR (CDCl ₃ ) δ (ppm): 3.09 (2H, t, J = 7.0 Hz), 3.76 (2H, q, J = 6.7 Hz), 6.54 (1H, br s), 7.19-7.26 (2H, m), 7.34 (1H, dd, J = 7.7 Hz, 4.8 Hz), 7.40 (1H, d, J = 1.7 Hz), 8.08 (1H, dd, J = 7.6 Hz, 2.0 Hz), 8.46 (1H, dd, J = 4.8 Hz, 2.1 Hz).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ（ｐｐｍ）：２．４４（３Ｈ，ｓ），３．０４（２Ｈ，ｔ，Ｊ＝６．９Ｈｚ），３．６８（２Ｈ，ｑ，Ｊ＝６．９Ｈｚ），３．７９（３Ｈ，ｓ），６．１１（１Ｈ，ｂｒ ｓ），７．１９−７．２１（２Ｈ，ｍ），７．３９−７．４０（１Ｈ，ｍ）． The following compound was obtained according to the method described in Production Example 1 using 3-chloro-1,5-dimethyl-4-pyrazolecarboxylic acid chloride instead of 2-trifluoromethylbenzoic acid chloride.
N- {2- (2,4-dichlorophenyl) ethyl} -3-chloro-1,5-dimethyl-4-pyrazolecarboxamide (present compound 3)

¹ H-NMR (CDCl ₃ ) δ (ppm): 2.44 (3H, s), 3.04 (2H, t, J = 6.9 Hz), 3.68 (2H, q, J = 6.9 Hz) ), 3.79 (3H, s), 6.11 (1H, br s), 7.19-7.21 (2H, m), 7.39-7.40 (1H, m).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ（ｐｐｍ）：３．０２（２Ｈ，ｔ），３．６７（２Ｈ，ｑ），３．９５（３Ｈ，ｓ），６．０４（１Ｈ，ｂｒ ），７．１８−７．１９（２Ｈ，ｍ），７．３９（１Ｈ，ｓ），７．９０（１Ｈ，ｓ）． Production Example 2
A mixture of 2- (2,4-dichlorophenyl) ethylamine 0.38 g, 1-methyl-3-trifluoromethyl-4-pyrazolecarboxylic acid (0.39 g) and pyridine (5 ml) was stirred at room temperature, -3- (3-Dimethylaminopropyl) carbodiimide hydrochloride (0.42 g) was added at room temperature. After 2 hours, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with 5% aqueous hydrochloric acid, water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with hexane to obtain 0.64 g of N- {2- (2,4-dichlorophenyl) ethyl} -1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide (present compound 4). It was.

¹ H-NMR (CDCl ₃ ) δ (ppm): 3.02 (2H, t), 3.67 (2H, q), 3.95 (3H, s), 6.04 (1H, br), 7 .18-7.19 (2H, m), 7.39 (1H, s), 7.90 (1H, s).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ（ｐｐｍ）：２．３６（３Ｈ，ｓ），３．０１（２Ｈ，ｔ），３．６５（２Ｈ，ｑ），５．９６（１Ｈ，ｂｒ ｓ），７．２６（１Ｈ，ｓ），７．１６−７．１９（２Ｈ，ｍ），７．３９（１Ｈ，ｓ）． Production Example 3
A mixture of 0.30 g of 2- (2,4-dichlorophenyl) ethylamine, 4 ml of toluene, 4 ml of water and 0.15 g of sodium hydroxide was stirred, and at room temperature, 5-methyl-2-trifluoromethyl-3-furancarboxylic acid After a mixture of chloride (0.2 g) and toluene (1 ml) was added, 15 minutes later, water was added to the reaction mixture and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, subjected to silica gel column chromatography (elution solvent was a mixed solvent of hexane and ethyl acetate), and N- {2- (2,4-dichlorophenyl) ethyl} -5- 0.30 g of methyl-2-trifluoromethyl-3-furancarboxamide (the present compound 5) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 2.36 (3H, s), 3.01 (2H, t), 3.65 (2H, q), 5.96 (1H, br s), 7.26 (1H, s), 7.16-7.19 (2H, m), 7.39 (1H, s).

Next, formulation examples are shown. In addition, a part represents a weight part.
Formulation Example 1
50 parts of each of the compounds 1-5 of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain each wettable powder.

Formulation Example 2
20 parts of each of the compounds 1 to 5 of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely pulverized by a wet pulverization method. Add 40 parts of an aqueous solution containing 0.05 part and 0.1 part of aluminum magnesium silicate, add 10 parts of propylene glycol, and stir and mix to obtain each flowable preparation.

Formulation Example 3
2 parts of each of the present compounds 1 to 5, 88 parts of kaolin clay and 10 parts of talc are pulverized and mixed well to obtain each powder.

Formulation Example 4
5 parts of each of the present compounds 1 to 5, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene are mixed well to obtain each emulsion.

Formulation Example 5
2 parts of each of the present compounds 1 to 5, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, and after further mixing with water, Granulate and dry to obtain each granule.

Formulation Example 6
10 parts of each of the compounds 1 to 5, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain each flowable preparation.

Formulation Example 7
10 parts of each of the present compounds 1 to 5 and 5 parts of Sorpol 1200 (a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co., Ltd.) were mixed and dissolved in 47 parts of dimethyl sulfoxide and 38 parts of xylene. To obtain an emulsion.

  Next, test examples show that the compounds of the present invention are useful as plant disease control agents. The control effect of the compound of the present invention is obtained by visually observing the area of the lesion on the test plant at the time of investigation, and comparing the area of the lesion in the untreated group with the area of the lesion in the compound-treated group. evaluated.

Test Example 1: Cucumber gray mold control effect test (prevention effect)
A plastic pot was filled with sand loam, sown with cucumber (Sagamihanjiro), and grown in a greenhouse for 12 days. Each of the flowable formulations of the present compounds 1 to 5 obtained according to Formulation Example 6 was diluted with water to a predetermined concentration (500 ppm), and then sprayed on the foliage so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a PDA medium containing mycelium of cucumber gray mold was placed on the cucumber leaf surface. After inoculation at 10 ° C. under high humidity for 4 days, the control effect was investigated. As a result, the lesion area on the plant of the above-mentioned compound-treated group was 10% or less of the lesion area of the untreated group.

Test Example 2: Radish Black Soot Disease Control Effect Test Plastic pots were filled with sand loam, seeded with radish (40 days early), and grown in a greenhouse for 5 days. The flowable formulations of the present compounds 1 to 5 obtained according to Formulation Example 6 were each diluted with water to a predetermined concentration (500 ppm), and sprayed so as to sufficiently adhere to the radish stems and leaves. After spraying, the plants were air-dried and spray-inoculated with a radish black soot spore suspension. After inoculation, it was placed under a high humidity of 20 ° C. for 4 days, and then the control effect was investigated. As a result, the lesion area on the plant of the above-mentioned compound-treated group was 10% or less of the lesion area of the untreated group.

Test Example 3: Cucumber Nuclear Disease Control Effect Test A plastic pot was stuffed with sand loam, seeded with cucumber (Sagamihanjiro), and grown in a greenhouse for 12 days. The flowable formulations of the present compounds 1 to 5 obtained according to Formulation Example 6 were each diluted with water to a predetermined concentration (500 ppm) and sprayed so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of cucumber sclerotia was placed on the cucumber leaf surface. After inoculation, the specimen was placed at 18 ° C. under high humidity for 4 days, and then the control effect was examined. As a result, the lesion area on the plant of the above-mentioned compound-treated group was 10% or less of the lesion area of the untreated group.

The compound of the present invention has an excellent plant disease control effect and is useful.

Claims (11)

Formula (I)

[In the formula, A represents an aromatic cyclic group which may have a hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom, and the aromatic cyclic group is a carbonyl group in the formula (I). The position adjacent to the position bonded to the group is substituted with R ¹ and may be further substituted with a C1-C4 alkyl group which may be substituted with a halogen atom and / or a halogen atom. R ¹ represents a C1-C4 alkyl group which may be substituted with a halogen atom or a halogen atom. ]
A phenethylamide compound represented by: In the formula (I), A is the following A1 to A7

[R ¹ represents the same meaning as described above,
R ² represents a C1-C4 alkyl group which may be substituted with a halogen atom,
R ³ represents a C1-C4 alkyl group optionally substituted with a halogen atom, a halogen atom or a hydrogen atom,
R ⁴ represents a C1-C4 alkyl group optionally substituted with a halogen atom, a halogen atom or a hydrogen atom. ]
The phenethyl amide compound according to claim 1, which is any group represented by the formula: The phenethyl amide compound according to claim 1, wherein A in the formula (I) is a group represented by A1. The phenethylamide compound according to claim 1, wherein A in the formula (I) is a group represented by A2. The phenethylamide compound according to claim 1, wherein A in the formula (I) is a group represented by A3. The phenethylamide compound according to claim 1, wherein A in the formula (I) is a group represented by A4. Phenethylamide compound as claimed in any of claims 1 to 6 R ¹ is a chlorine atom. Phenethylamide compound as claimed in any of claims 1 to 6 R ¹ is a trifluoromethyl group. In the formula (I), A represents 2-trifluoromethylphenyl group, 1-methyl-3-trifluoromethylpyrazol-4-yl group, 5-methyl-2-trifluoromethylfuran-3-yl group, 2- The phenethylamide compound according to claim 1, which is a chloropyridin-3-yl group or a 3-chloro-1,5-dimethylpyrazol-4-yl group. A plant disease control agent comprising the phenethylamide compound according to any one of claims 1 to 9 as an active ingredient. A method for controlling plant diseases, which comprises applying the phenethylamide compound according to any one of claims 1 to 9 to a plant or soil in which the plant grows.