JPH0725840A - Amide compound and plant disease injury controlling agent containing the same as active ingredient - Google Patents
Amide compound and plant disease injury controlling agent containing the same as active ingredientInfo
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- JPH0725840A JPH0725840A JP17519793A JP17519793A JPH0725840A JP H0725840 A JPH0725840 A JP H0725840A JP 17519793 A JP17519793 A JP 17519793A JP 17519793 A JP17519793 A JP 17519793A JP H0725840 A JPH0725840 A JP H0725840A
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- compound
- amide compound
- alkyl
- methyl
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はアミド化合物およびそれ
を有効成分とする植物病害防除剤に関する。TECHNICAL FIELD The present invention relates to an amide compound and a plant disease controlling agent containing the amide compound as an active ingredient.
【従来の技術】従来、特開平 3-246268 号公報等に、あ
る種のアミド化合物が植物病害防除剤として使用し得る
ことが記載されている。2. Description of the Related Art Heretofore, JP-A-3-246268 discloses that certain amide compounds can be used as a plant disease controlling agent.
【発明が解決しようとする課題】しかしながら、これら
の化合物の植物病害防除剤としての効力は必ずしも常に
満足すべきものとは言い難い。However, the efficacy of these compounds as plant disease controlling agents is not always satisfactory.
【０００２】[0002]
【課題を解決するための手段】本発明者らは、この様な
状況に鑑み、植物病害に対する優れた効力を有する化合
物を開発すべく、鋭意検討した結果、下記一般式 化２
で示されるアミド化合物が、各種の植物病害に対して優
れた効力を有することを見出し、本発明に至った。すな
わち、本発明は一般式 化２In view of such a situation, the inventors of the present invention have made earnest studies to develop a compound having excellent efficacy against plant diseases, and as a result, have shown the following general formula:
It was found that the amide compound represented by the formula (3) has excellent efficacy against various plant diseases, and the present invention has been completed. That is, the present invention has the general formula
【化２】 〔式中、Ｒ1 はＣ1 −Ｃ4 アルキル基を表わし、Ｒ2 お
よびＲ3 は同一または相異なり水素原子またはＣ1 −Ｃ
4 アルキル基を表わす。Ｒ4 はメチル基またはエチル基
を表わす。ＸはＣ1 −Ｃ4 アルキル基、Ｃ2 −Ｃ4 アル
ケニル基、Ｃ2 −Ｃ4 アルキニル基、Ｃ1 −Ｃ4 ハロア
ルキル基、Ｃ1 −Ｃ4 アルコキシ基、Ｃ3−Ｃ4 アルケ
ニルオキシ基、Ｃ3 −Ｃ4 アルキニルオキシ基、Ｃ1 −
Ｃ4 ハロアルコキシ基、Ｃ1 −Ｃ4 アルキルチオ基、Ｃ
1 −Ｃ4 ハロアルキルチオ基、Ｃ3−Ｃ8 シクロアルキ
ル基またはハロゲン原子を表わす。ｎは０〜３の整数を
表わす。ｎが２または３を表わすとき、Ｘは同一でも相
異なっていてもよい。〕で示されるアミド化合物（以
下、本発明化合物と記す。）およびそれを有効成分とす
る植物病害防除剤を提供するものである。[Chemical 2] [In the formula, R 1 represents a C 1 -C 4 alkyl group, R 2 and R 3 are the same or different and are a hydrogen atom or C 1 -C
4 represents an alkyl group. R 4 represents a methyl group or an ethyl group. X is C 1 -C 4 alkyl group, C 2 -C 4 alkenyl group, C 2 -C 4 alkynyl group, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, C 3 -C 4 alkenyloxy group , C 3 -C 4 alkynyloxy group, C 1-
C 4 haloalkoxy group, C 1 -C 4 alkylthio group, C
1 -C 4 haloalkylthio group, a C 3 -C 8 cycloalkyl group or a halogen atom. n represents an integer of 0 to 3. When n represents 2 or 3, X may be the same or different. ] The amide compound shown by these (henceforth compound of this invention) and the plant disease controlling agent which uses it as an active ingredient are provided.
【０００３】一般式 化２において、Ｃ1 −Ｃ4 アルキ
ル基としては、メチル基、エチル基、ｎ−プロピル基、
iso−プロピル基、tert−ブチル基、ｎ−ブチル基、 s
ec−ブチル基等があげられ、Ｃ2 −Ｃ4 アルケニル基と
してはアリル基等が挙げられ、Ｃ2 −Ｃ4 アルキニル基
としてはプロパルギル基等が挙げられ、Ｃ1 −Ｃ4 ハロ
アルキル基としてはトリフルオロメチル基等が挙げら
れ、Ｃ1 −Ｃ4 アルコキシ基としてはメトキシ基、エト
キシ基、 iso−プロポキシ基等が挙げられ、Ｃ3−Ｃ4
アルケニルオキシ基としてはアリルオキシ基等が挙げら
れ、Ｃ3 −Ｃ4 アルキニルオキシ基としてはプロパルギ
ルオキシ基等が挙げられ、Ｃ1 −Ｃ4 ハロアルコキシ基
としてはトリフルオロメトキシ基、 1,1,2,2−テトラフ
ルオロエトキシ基、 2,2,2−トリフルオロエトキシ基、
ジフルオロメトキシ基等が挙げられ、Ｃ1 −Ｃ4 アルキ
ルチオ基としてはメチルチオ基、エチルチオ基等が挙げ
られ、Ｃ1 −Ｃ4 ハロアルキルチオ基としてはトリフル
オロメチルチオ基等が挙げられ、Ｃ3 −Ｃ8 シクロアル
キル基としてはシクロプロピル基、シクロペンチル基、
シクロヘキシル基等が挙げられ、ハロゲン原子としては
フッ素原子、塩素原子、臭素原子等が挙げられる。本発
明化合物のうち、Ｒ1 ，Ｒ3 およびＲ4 がメチル基であ
り、Ｒ2 が水素原子であるものが好ましく、その化合物
の中でも、ＸがＣ1 −Ｃ4 アルキル基、フッ素原子、塩
素原子またはトリフルオロメチル基であり、ｎが０〜２
の整数であるものが好ましい。また、Ｘの置換位置は３
位および／または４位が好ましい。本発明化合物は部分
構造として２つの非対称二重結合（Ｃ＝ＮおよびＣ＝
Ｃ）を有することから、本発明化合物には合計４つの異
性体（（Ｅ）−（Ｅ）、（Ｅ）−（Ｚ）、（Ｚ）−
（Ｅ）および（Ｚ）−（Ｚ））が存在するが、本発明に
は各々の異性体およびそれらの混合物が含まれる。（こ
こで用いた、（Ｅ）および（Ｚ）という用語は、広く知
られたカーン−インゴールド−プレログ系により定義さ
れたものである。）In the general formula 2, the C 1 -C 4 alkyl group is a methyl group, an ethyl group, an n-propyl group,
iso-propyl group, tert-butyl group, n-butyl group, s
Examples include an ec-butyl group and the like, examples of the C 2 -C 4 alkenyl group include an allyl group, examples of the C 2 -C 4 alkynyl group include a propargyl group, and examples of the C 1 -C 4 haloalkyl group. Examples thereof include a trifluoromethyl group, examples of the C 1 -C 4 alkoxy group include a methoxy group, an ethoxy group, an iso-propoxy group, etc., and a C 3 -C 4 group.
The alkenyloxy group includes an allyloxy group and the like, the C 3 -C 4 alkynyloxy group includes a propargyloxy group and the like, and the C 1 -C 4 haloalkoxy group includes a trifluoromethoxy group, 1,1,2 , 2-tetrafluoroethoxy group, 2,2,2-trifluoroethoxy group,
Examples thereof include a difluoromethoxy group, examples of the C 1 -C 4 alkylthio group include a methylthio group and ethylthio group, examples of the C 1 -C 4 haloalkylthio group include a trifluoromethylthio group, and a C 3 -C group. 8 cycloalkyl groups as cycloalkyl groups, cyclopentyl groups,
Examples thereof include a cyclohexyl group, and examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom. Of the compounds of the present invention, those in which R 1 , R 3 and R 4 are methyl groups and R 2 is a hydrogen atom are preferred, and among these compounds, X is a C 1 -C 4 alkyl group, a fluorine atom, chlorine An atom or a trifluoromethyl group, n is 0 to 2
Is preferably an integer. The substitution position of X is 3
Position and / or position 4 are preferred. The compound of the present invention has two asymmetric double bonds (C = N and C =
Since it has C), the compound of the present invention has a total of four isomers ((E)-(E), (E)-(Z), (Z)-).
(E) and (Z)-(Z)) are present, but the present invention includes each isomer and mixtures thereof. (As used herein, the terms (E) and (Z) are defined by the well-known Kahn-Ingold-Prelog system.)
【０００４】本発明化合物は、種々の植物病害に対し、
予防効果、治療効果、浸透移行効果を示す。本発明化合
物により防除可能な植物病害としては、イネのいもち病
（Pyricularia oryzae）、ごま葉枯病（Cochliobolus m
iyabeanus)、紋枯病（Rhizoctonia solani）、ムギ類の
うどんこ病（Erysiphe graminis, f. SP. hordei, f.S
P. tritici）、赤かび病（Gibberella zeae) 、さび病
（Puccinia striiformis, P. graminis, P. recodita,
P. hordei)、雪腐病（Typhhula sp., Micronectriella
nivalis)、裸黒穂病（Ustilago tritici, U. nuda)、な
まぐさ黒穂病（Tilletia caries)、眼紋病（Pseudocerc
osporella herpotrichoides)、雲形病（Rhynchosporium
secalis) 、葉枯病（Septoria tritici）、 ふ枯病
（Leptosphaeria nodorum)、カンキツの黒点病（Diapor
the citri)、そうか病（Elsinoe fawcetti) 、果実腐敗
病（Penicillium digitatum, P. italicum) 、リンゴの
モニリア病（Sclerotinica mail)、腐らん病（Valsa ma
li) 、うどんこ病（Podpsphaera leucotricha)、斑点落
葉病（Alternaria mali)、黒星病（Venturia inaequali
s)、ナシの黒星病（Venturia nashicola, V. pirina)、
黒斑病（Alternaria kikuchiana)、赤星病（Gymnospora
ngium haraeanum)、モモの灰星病（Sclerotinia cinere
a)、黒星病（Cladosporium carpophilum) 、フォモプシ
ス腐敗病（Phomopsis sp.)、ブドウの黒とう病（Elsino
e ampelina) 、晩腐病（Glomerella cingulate) 、うど
んこ病（Uncinula necator) 、さび病（Phakopsora amp
elopsidis)、ブラックロット病（Guignardia bidwelli
i) 、べと病（Plasmopara viticola)、カキの炭そ病（G
loeosporium kaki)、落葉病（Cercosporakaki, Mycosph
aerella nawae) 、ウリ類の炭そ病（Colletotrichum la
genarium)、うどんこ病（Sphaerotheca fuliginea) 、
つる枯病（Mycosphaerella melonis）、べと病（Pseudo
peronospora cubensis) 、疫病（Phytophthora sp.) 、
トマトの輪紋病（Alternaria solani)、葉かび病（Clad
osporium fulvum)、疫病（Phytophthora infestans) 、
ナスの褐紋病（Phomopsis vexans) 、うどんこ病（Erys
iphe cichoracearum) 、アブラナ科野菜の黒斑病（Alte
rnaia japonica) 、白斑病（Cercosporella brassica
e)、ネギのさび病（Puccinia allii) 、ダイズの紫斑病
（Cercospora kikuchii)、黒とう病（Elsinoe glycine
s) 、黒点病（Diaporthe phaseolorum var. sojae) 、
インゲンの炭そ病（Colletotrichum lindemthianum) 、
ラッカセイの黒渋病（Mycosphaerella personatum)、褐
斑病（Cercospora arachidicola)、エンドウのうどんこ
病（Erysiphe pisi)、ジャガイモの夏疫病（Alternaria
solani)、疫病（Phytophthora infestans) 、イチゴの
うどんこ病（Sphaerotheca humuli)、チュの網もち病
（Exobasidium reticulatum)、白星病（Elsinoe leucos
pila) 、タバコの赤星病（Alternaria longipes)、うど
んこ病（Erysiphe cichoracearum) 、炭そ病（Colletot
richum tabacum) 、べと病（Peronospora tabacina) 、
疫病（Phytophthora nicotianae)、テンサイの褐斑病
（Cercospora beticola)、バラの黒星病（Diplocarpon
rosae)、うどんこ病（Sphaerotheca pannosa) 、キクの
褐斑病（Septoria chrysanthemi-indici) 、白サビ病
（Pucciniahoriana) 、種々の作物の灰色かび病（Botry
tis cinerea) 、菌核病（Sclerotinia sclerotiorum)
等があげられる。The compounds of the present invention are effective against various plant diseases.
It shows preventive, therapeutic and osmotic effects. Plant diseases which can be controlled by the compound of the present invention include rice blast ( Pyricularia oryzae ) and sesame leaf blight ( Cochliobolus m.
iyabeanus) , blight ( Rhizoctonia solani ), and powdery mildew of wheat ( Erysiphe graminis, f . SP. hordei , fS
P. tritici ), Fusarium head blight ( Gibberella zeae) , Rust ( Puccinia striiformis, P. graminis, P. recodita,
P. hordei) , snow rot ( Typhhula sp., Micronectriella)
nivalis) , naked smut ( Ustilago tritici, U. nuda ) , linseed smut ( Tilletia caries) , eye spot ( Pseudocerc )
osporella herpotrichoides) , cloud disease ( Rhynchosporium
secalis ), leaf blight ( Setoria tritici ), wilt ( Leptosphaeria nodorum) , citrus black spot ( Diapor)
the citri) , scab ( Elsinoe fawcetti ), fruit rot ( Penicillium digitatum, P. italicum ) , monili disease of apple ( Sclerotinica mail) , rot ( Valsa ma)
li ), powdery mildew ( Podpsphaera leucotricha) , leaf spot disease ( Alternaria mali) , scab ( Venturia inaequali)
s) , pear scab ( Venturia nashicola, V. pirina) ,
Black spot ( Alternaria kikuchiana) , Red scab ( Gymnospora )
ngium haraeanum) , Peach scab ( Sclerotinia cinere)
a) , scab ( Cladosporium carpophilum ), Phomopsis sp. ( phomopsis sp.) , black rot of grape ( Elsino
e ampelina ), late rot ( Glomerella cingulate ), powdery mildew ( Uncinula necator ), rust ( Pakopsora amp)
elopsidis) , Black Rot disease ( Guignardia bidwelli
i ), downy mildew ( Plasmopara viticola) , anthracnose of oyster ( G
loeosporium kaki) , leaf blight ( Cercosporakaki, Mycosph
aerella nawae ), anthracnose of cucumber ( Colletotrichum la)
genarium) , powdery mildew ( Sphaerotheca fuliginea ),
Blight ( Mycosphaerella melonis ), downy mildew ( Pseudo
peronospora cubensis ), plague ( Phytophthora sp. ),
Alternaria solani on tomato, leaf mold ( Clad
osporium fulvum) , plague ( Phytophthora infestans ),
Eggplant brown leaf spot ( Phomospsis vexans ), powdery mildew ( Erys )
iphe cichoracearum ), black spot of cruciferous vegetable ( Alte
rnaia japonica ), White spot ( Cercosporella brassica)
e) , green onion rust ( Puccinia allii ), soybean purpura ( Cercospora kikuchii) , black rot ( Elsinoe glycine)
s ), Black spot ( Diaporthe phaseolorum var. sojae ),
Green Bean Anthracnose ( Colletotrichum lindemthianum ),
Black peanut Shibu disease (Mycosphaerella personatum), brown spot disease (Cercospora arachidicola), pea powdery mildew (Erysiphe pisi), potato early blight (Alternaria
solani) , plague ( Phytophthora infestans ), strawberry powdery mildew ( Sphaerotheca humuli) , Chu net blast ( Exobasidium reticulatum) , white scab ( Elsinoe leucos)
pila), tobacco gymnosporangium (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletot
richum tabacum ), downy mildew ( Peronospora tabacina ),
Plague ( Phytophthora nicotianae) , brown spot of sugar beet ( Cercospora beticola) , black scab of rose ( Diplocarpon)
rosae) , powdery mildew ( Sphaerotheca pannosa ), brown spot of chrysanthemum ( Setoria chrysanthemi-indici ), white rust ( Pucciniahoriana ), gray mold of various crops ( Botry)
tis cinerea ), Sclerotinia sclerotiorum
Etc.
【０００５】次に、本発明化合物の製造法について詳し
く説明する。本発明化合物は、たとえば一般式 化３Next, the method for producing the compound of the present invention will be described in detail. The compound of the present invention has, for example, the general formula:
【化３】 〔式中、Ｒ1 、Ｒ2 およびＲ3 は前記と同じ意味を表わ
す。〕で示されるフェノール誘導体と、一般式 化４[Chemical 3] [In the formula, R 1 , R 2 and R 3 have the same meanings as described above. ] And a phenol derivative represented by the general formula:
【化４】 〔式中、Ｒ4 、Ｘおよびｎは前記と同じ意味を表わす。
Ｙはハロゲン原子（塩素原子、臭素原子、ヨウ素原子
等）を表わす。〕で示されるハロゲン化合物とを塩基の
存在下に反応させる事により得ることができる。この反
応において、塩基としては、水酸化ナトリウム、水酸化
カリウム等のアルカリ金属水酸化物、炭酸ナトリウム、
炭酸カリウム等のアルカリ金属炭酸塩、水素化ナトリウ
ム等のアルカリ金属水素化物、ナトリウムメチラート、
ナトリウムエチラート等のアルカリ金属アルコキシド
（たとえば、Ｃ1 −Ｃ4 アルコキシド）等あるいはそれ
らの混合物が通常使用される。反応に供される試剤の量
は、一般式 化３で示されるフェノール誘導体１モルに
対して、通常、一般式 化４で示されるハロゲン化合物
は１〜２モルの割合、塩基は１〜３の割合である。反応
温度および反応時間の範囲は通常、それぞれ−１０℃〜
溶媒の沸点または約１５０℃および約１０分〜５時間で
ある。上記反応においては、必ずしも溶媒は必要ではな
いが、通常反応は溶媒中で行われる。使用しうる溶媒と
しては、使用する塩基の種類によっても異なるが、例え
ばジエチルエーテル、ジイソプロピルエーテル、ジオキ
サン、テトラヒドロフラン等のエーテル類、ホルムアミ
ド、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、ヘ
キサン、ヘプタン等の脂肪族炭化水素類、ベンゼン、ト
ルエン等の芳香族炭化水素類、クロロホルム、四塩化炭
素、ジクロロベンゼン等のハロゲン化炭化水素類、アセ
トン等のケトン類、アセトニトリル等のニトリル類、メ
タノール、エタノール等のアルコール類、ピリジン類、
ジメチルスルホキシド、スルホラン等、水およびそれら
の混合物があげられる。反応終了後の反応液は、抽出等
の通常の後処理を行い、必要に応じてクロマトグラフィ
ー、再結晶等の操作によって精製することにより、目的
とする本発明化合物を得ることが出来る。[Chemical 4] [In the formula, R 4 , X and n have the same meanings as described above.
Y represents a halogen atom (chlorine atom, bromine atom, iodine atom, etc.). ] It can be obtained by reacting the halogen compound represented by the following in the presence of a base. In this reaction, as the base, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate,
Alkali metal carbonates such as potassium carbonate, alkali metal hydrides such as sodium hydride, sodium methylate,
Alkali metal alkoxides such as sodium ethylate (eg C 1 -C 4 alkoxides) and the like or mixtures thereof are usually used. The amount of the reagent used in the reaction is usually 1 to 2 mol of the halogen compound represented by the general formula 4 and 1 to 3 mol of the base with respect to 1 mol of the phenol derivative represented by the general formula 3. It is a ratio. The reaction temperature and the reaction time are usually in the range of -10 ° C to
The boiling point of the solvent or about 150 ° C. and about 10 minutes to 5 hours. In the above reaction, a solvent is not always necessary, but the reaction is usually performed in the solvent. The solvent that can be used varies depending on the type of base used, but examples thereof include ethers such as diethyl ether, diisopropyl ether, dioxane and tetrahydrofuran, acid amides such as formamide and N, N-dimethylformamide, hexane and heptane. Aliphatic hydrocarbons, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as chloroform, carbon tetrachloride and dichlorobenzene, ketones such as acetone, nitriles such as acetonitrile, methanol, ethanol, etc. Alcohols, pyridines,
Examples include dimethyl sulfoxide, sulfolane, water, and a mixture thereof. After completion of the reaction, the reaction solution is subjected to usual post-treatments such as extraction and, if necessary, purified by operations such as chromatography and recrystallization to obtain the desired compound of the present invention.
【０００６】本発明化合物の例を表１および表２に示
す。（一般式 化２で示される化合物の各置換基を示
す。）なお、ｃ−Ｃ6 Ｈ11はシクロヘキシル基を表す。Examples of the compounds of the present invention are shown in Tables 1 and 2. (Represented by the general formula of 2 shows the respective substituents of the compound.) Incidentally, c-C 6 H 11 represents a cyclohexyl group.
【表１】 [Table 1]
【表２】 [Table 2]
【０００７】本発明化合物を製造する際の原料化合物で
ある一般式 化３で示されるフェノール誘導体は、例え
ば下記のスキーム 化５により製造することができる。The phenol derivative represented by the general formula (3), which is a starting compound for producing the compound of the present invention, can be produced, for example, by the following scheme (5).
【化５】 〔式中、Ｒ1 、Ｒ2 およびＲ3 は前記と同じ意味を表わ
し、Ｒ5 は低級アルキル基（メチル基、エチル基等）を
表わし、Ｚ1 は臭素原子またはヨウ素原子を表わし、ｃ
ａｔはピリジニウムｐ−トルエンスルホネート等の酸触
媒等を表す。〕[Chemical 5] [In the formula, R 1 , R 2 and R 3 have the same meanings as described above, R 5 represents a lower alkyl group (methyl group, ethyl group, etc.), Z 1 represents a bromine atom or an iodine atom, and c
at represents an acid catalyst such as pyridinium p-toluenesulfonate. ]
【０００８】一般式 化４で示されるハロゲン化合物
は、例えば下記のスキーム 化６により製造することが
できる。The halogen compound represented by the general formula 4 can be produced, for example, by the following scheme 6.
【化６】 〔式中、Ｒ4 、Ｘ、ｎおよびＹは前記と同じ意味を表わ
し、Ｚ2 は塩素原子、臭素原子またはヨウ素原子を表わ
す。〕[Chemical 6] [In the formula, R 4 , X, n and Y have the same meanings as described above, and Z 2 represents a chlorine atom, a bromine atom or an iodine atom. ]
【０００９】本発明化合物を植物病害防除剤の有効成分
として用いる場合、他に何らの成分も加えずそのまま用
いてもよいが、通常は固体担体、液体担体、界面活性剤
その他の製剤用補助剤と混合して、乳剤、水和剤、懸濁
剤、粉剤、粒剤等に製剤して用いる。この場合、有効成
分である本発明化合物の製剤中での有効成分含有量は重
量比で 0.1〜９５％、好ましくは１〜８０％である。上
述の固体担体としては、カオリンクレー、アッタパルジ
ャイトクレー、ベントナイト、酸性白土、パイロフィラ
イト、タルク、珪藻土、方解石、トウモロコシ穂軸粉、
クルミ殻粉、尿素、硫酸アンモニウム、合成含水酸化珪
素等の微粉末あるいは粒状物があげられ、液体担体とし
ては、キシレン、メチルナフタレン等の芳香族炭化水
素、イソプロパノール、エチレングリコール、エトキシ
エタノール等のアルコール、アセトン、シクロヘキサノ
ン、イソホロン等のケトン、大豆油、綿実油等の植物
油、ジメチルスルホキシド、アセトニトリル、水等があ
げられる。乳化、分散、湿展のために用いられる界面活
性剤としては、アルキル硫酸エステル塩、アルキルスル
ホン酸塩、アルキルアリールスルホン酸塩、ジアルキル
スルホコハク酸塩、ポリオキシエチレンアルキルアリー
ルエーテルリン酸エステル塩、ナフタレンスルホン酸ホ
ルマリン縮合物等の陰イオン界面活性剤、ポリオキシエ
チレンアルキルエーテル、ポリオキシエチレンポリオキ
シプロピレンブロックコポリマー、ソルビタン脂肪酸エ
ステル、ポリオキシエチレンソルビタン脂肪酸エステル
等の非イオン界面活性剤等があげられる。製剤用補助剤
としては、リグニンスルホン酸塩、アルギン酸塩、ポリ
ビニルアルコール、アラビアガム、ＣＭＣ（カルボキシ
メチルセルロース）、ＰＡＰ（酸性リン酸イソプロピ
ル）等があげられる。本発明化合物を植物病害防除剤の
有効成分として用いる場合、その有効成分の施用量は、
１アールあたり通常 0.01 〜１０００ｇ、好ましくは0.
1 〜１００ｇであり、乳剤、水和剤、懸濁剤等を水で希
釈して施用する場合は、その施用濃度は、0.0001〜 0.5
（W/V)％、好ましくは0.0005〜 0.2（W/V)％であり粉
剤、粒剤等はなんら希釈することなくそのまま施用す
る。本発明化合物の施用方法としては、茎葉散布、土壌
処理、種子消毒等が挙げられるが、通常の当業者が利用
できるどのような施用方法も用いることができる。本発
明化合物は他の殺菌剤と混合して用いることにより殺菌
効力の増強を期待できる。さらに、殺虫剤、殺ダニ剤、
殺線虫剤、除草剤、植物生長調節剤、肥料と混合して用
いることもできる。When the compound of the present invention is used as an active ingredient of a plant disease controlling agent, it may be used as it is without adding any other component, but it is usually a solid carrier, a liquid carrier, a surfactant or other auxiliary agent for formulation. It is mixed with and used as a formulation such as an emulsion, a wettable powder, a suspension, a powder and a granule. In this case, the content of the active ingredient in the preparation of the compound of the present invention as the active ingredient is 0.1 to 95% by weight, preferably 1 to 80%. As the above solid carrier, kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder,
Walnut shell powder, urea, ammonium sulfate, fine powder or granules such as synthetic hydrous silicon oxide, and the liquid carrier, xylene, aromatic hydrocarbons such as methylnaphthalene, alcohols such as isopropanol, ethylene glycol, ethoxyethanol, Examples thereof include ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile and water. Surfactants used for emulsification, dispersion and wet extension include alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate ester salts, naphthalene. Examples thereof include anionic surfactants such as sulfonic acid formalin condensates, nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters and polyoxyethylene sorbitan fatty acid esters. Examples of the auxiliaries for formulation include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate) and the like. When the compound of the present invention is used as an active ingredient of a plant disease controlling agent, the application amount of the active ingredient is
Usually 0.01 to 1000 g per are, preferably 0.1.
1 to 100 g, and when the emulsion, wettable powder, suspending agent, etc. are diluted with water and applied, the application concentration is 0.0001 to 0.5.
(W / V)%, preferably 0.0005 to 0.2 (W / V)%, and powders, granules, etc. are applied as they are without any dilution. Examples of the application method of the compound of the present invention include foliar application, soil treatment, seed disinfection, etc., but any application method that can be used by a person skilled in the art can be used. The compound of the present invention can be expected to enhance the bactericidal effect by mixing with the other bactericide. In addition, insecticides, acaricides,
It can also be used as a mixture with nematicides, herbicides, plant growth regulators and fertilizers.
【００１０】[0010]
【実施例】以下、本発明を製造例、製剤例および試験例
等により、さらに詳しく説明するが、本発明はこれらの
例のみに限定されるものではない。まず、製造例を示
す。 製造例 （Ｅ）−Ｎ−メチル−２−（２−ヒドロキシフェニル）
−２−メトキシイミノ酢酸アミド１ｇを乾燥Ｎ，Ｎ−ジ
メチルホルムアミド３０mlに溶解し、炭酸カリウム0.67
ｇおよび（Ｅ）−１−クロロ−３−（ｐ−トリル）−ブ
ト−２−エン0.87ｇを加え、室温で３時間攪拌した。反
応液に水（１００ml）を加え、エーテル（１００ml×
２）で抽出し、有機層を無水硫酸マグネシウムで乾燥し
た後、減圧濃縮して油状残渣を得た。これをシリカゲル
カラムクロマトグラフィー（ヘキサン：酢酸エチル＝
４：１〜２：１(v/v))に付し、得られた結晶性残渣を２
−プロパノールから再結晶して、（Ｅ）−Ｎ−メチル−
２−［２−((Ｅ）−３−（ｐ−トリル）−ブト−２−エ
ニル）−オキシフェニル］−２−メトキシイミノ酢酸ア
ミド（本発明化合物（４)) 0.93ｇを得た。 ｍｐ １２４〜１２５℃ 上記製造例に準じて製造した本発明化合物の例を表３に
示す。（一般式 化２で示される化合物の各置換基を示
す。）The present invention will be described in more detail below with reference to production examples, formulation examples, test examples, etc., but the present invention is not limited to these examples. First, a production example is shown. Production Example (E) -N-methyl-2- (2-hydroxyphenyl)
1 g of 2-methoxyiminoacetic acid amide was dissolved in 30 ml of dry N, N-dimethylformamide, and potassium carbonate 0.67
g and (E) -1-chloro-3- (p-tolyl) -but-2-ene 0.87 g were added, and the mixture was stirred at room temperature for 3 hours. Water (100 ml) was added to the reaction solution, and ether (100 ml x
After extraction in 2), the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain an oily residue. This is subjected to silica gel column chromatography (hexane: ethyl acetate =
4: 1 to 2: 1 (v / v)), and the resulting crystalline residue was added to 2
Recrystallized from propanol to give (E) -N-methyl-
0.93 g of 2- [2-((E) -3- (p-tolyl) -but-2-enyl) -oxyphenyl] -2-methoxyiminoacetic acid amide (the present compound (4)) was obtained. mp 124 to 125 ° C. Table 3 shows examples of the compound of the present invention produced according to the above Production Example. (The respective substituents of the compound represented by the general formula 2 are shown.)
【表３】 物性 (1) ｍｐ １２４〜１２６℃ (2) ｍｐ １０
４〜１０６℃ (3) ｍｐ １０７〜１０８℃ (4) ｍｐ １２
４〜１２５℃ (5) viscous oil (6) viscous oil (7) ｎD 26.5 1.5552 (8) ｎD 24 1.55
71 (9) ｍｐ ９４〜９９℃ (10) ｍｐ １３
２〜１３６℃ (11) ｍｐ ８０〜８３℃ (12) ｍｐ １０
０〜１０２℃ (13) ｎD 24.5 1.5317[Table 3] Physical properties (1) mp 124-126 ° C (2) mp 10
4 to 106 ° C (3) mp 107 to 108 ° C (4) mp 12
4-125 ° C (5) viscous oil (6) viscous oil (7) n D 26.5 1.5552 (8) n D 24 1.55
71 (9) mp 94-99 ° C (10) mp 13
2 to 136 ° C (11) mp 80 to 83 ° C (12) mp 10
0 ~ 102 ℃ (13) n D 24.5 1.5317
【００１１】次に本発明化合物を製造する際の原料化合
物の製造例を参考例として示す。 参考例１ （Ｅ）−Ｎ−メチル−２−（２−ヒドロキシフェニル）
−２−メトキシイミノ酢酸アミドの製造 a) ｏ−ブロモフェノール５０ｇ、３，４−ジヒドロピ
ラン36.4ｇをジクロロメタン２００mlに溶解した。これ
にピリジニウムｐ−トルエンスルホネート3.64ｇを加
え、室温で一夜攪拌した。反応液を減圧濃縮し、得られ
た油状残渣にエーテル５００mlを加え、不溶物を濾去し
た後、再び減圧濃縮してオイル状残渣を得た。これに無
水テトラヒドロフラン（ＴＨＦ）３００mlを加え、−７
０℃に冷却し、1.6M ｎ−ブチルリチウムヘキサン溶液
２４０mlを−７０℃〜−６０℃で加えた。３０分間−７
０℃で攪拌の後、反応液にシュウ酸ジメチル６８ｇを加
え、１時間−７０℃で攪拌し、その後室温まで放冷し
た。反応液を水５００mlに注加し、エーテル５００ml×
２で抽出し、無水硫酸マグネシウムで乾燥した後、減圧
濃縮して油状残渣を得た。これをメタノール２００mlに
溶解し、メトキシアミン塩酸塩36.2ｇを加え、３時間加
熱還流した。反応液を放冷後、減圧濃縮し、得られた油
状残渣をシリカゲルカラムクロマトグラフィー（ヘキサ
ン：酢酸エチル＝４：１〜２：１(v/v))に付し、（Ｚ）
−メチル−２−（２−ヒドロキシフェニル）−２−メト
キシイミノアセテート31.5ｇおよび（Ｅ）−メチル−２
−（２−ヒドロキシフェニル）−２−メトキシイミノア
セテート16.4ｇをそれぞれ得た。 b) （Ｅ）−メチル−２−（２−ヒドロキシフェニル）
−２−メトキシイミノアセテート１０ｇをメチルアミン
の４０％メタノール溶液１００mlに溶解した。３０分
後、減圧濃縮して結晶状残渣を得た。これをヘキサンで
洗浄して（Ｅ）−Ｎ−メチル−２−（２−ヒドロキシフ
ェニル）−２−メトキシ酢酸アミド１０ｇを得た。 参考例２ （Ｅ）−１−クロロ−３−（ｐ−トリル）−ブト−２−
エンの製造 a) ４−ブロモトルエン１０ｇをＴＨＦ５０mlに溶解
し、−４０℃に冷却した。これに1.6M ｎ−ブチルリチ
ウムヘキサン溶液３８mlを加えた。反応液を一旦、０℃
にまで上昇させた後、−７０℃に冷却し、３０分間攪拌
した。これにメチルビニルケトン 4.5ｇを滴下した。そ
の後、−７０℃で３０分攪拌の後、室温まで放冷した。
反応液に１Ｎ塩酸１２５mlを加え、エーテル（２００ml
×２）で抽出し、無水硫酸マグネシウムで乾燥した後、
減圧濃縮し、油状残渣として３−ヒドロキシ−３−（ｐ
−トリル）−ブト−１−エンの粗製品 8.7ｇを得た。 b) 得られた粗３−ヒドロキシ−３−（ｐ−トリル）−
ブト−１−エン 8.7ｇに濃塩酸３０mlを加え、１時間室
温で攪拌した。反応液を放冷の後、水１００mlを加え、
エーテル（１００ml×２）で抽出し、エーテル層を水
洗、無水硫酸マグネシウムで乾燥した後、減圧濃縮して
オイル状残渣を得た。これを減圧濃縮して（Ｅ）−１−
クロロ−３−（ｐ−トリル）−ブト−２−エンを 7.9ｇ
得た。Next, a production example of a starting material compound for producing the compound of the present invention will be shown as a reference example. Reference Example 1 (E) -N-methyl-2- (2-hydroxyphenyl)
Preparation of 2-methoxyiminoacetic acid amide a) 50 g of o-bromophenol and 36.4 g of 3,4-dihydropyran were dissolved in 200 ml of dichloromethane. To this was added 3.64 g of pyridinium p-toluenesulfonate, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, 500 ml of ether was added to the obtained oily residue, the insoluble material was filtered off, and the residue was concentrated under reduced pressure again to give an oily residue. To this, 300 ml of anhydrous tetrahydrofuran (THF) was added, and -7
After cooling to 0 ° C, 240 ml of 1.6M n-butyllithium hexane solution was added at -70 ° C to -60 ° C. 30 minutes-7
After stirring at 0 ° C, 68 g of dimethyl oxalate was added to the reaction solution, stirred at -70 ° C for 1 hour, and then allowed to cool to room temperature. The reaction solution was poured into 500 ml of water, and 500 ml of ether was added.
Extraction with 2, drying over anhydrous magnesium sulfate, and concentration under reduced pressure gave an oily residue. This was dissolved in 200 ml of methanol, 36.2 g of methoxyamine hydrochloride was added, and the mixture was heated under reflux for 3 hours. The reaction solution was allowed to cool and then concentrated under reduced pressure, and the obtained oily residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 4: 1 to 2: 1 (v / v)), (Z).
-Methyl-2- (2-hydroxyphenyl) -2-methoxyiminoacetate 31.5 g and (E) -methyl-2
16.4 g of-(2-hydroxyphenyl) -2-methoxyiminoacetate was obtained. b) (E) -methyl-2- (2-hydroxyphenyl)
10 g of 2-methoxyiminoacetate was dissolved in 100 ml of a 40% methanol solution of methylamine. After 30 minutes, concentration under reduced pressure gave a crystalline residue. This was washed with hexane to obtain 10 g of (E) -N-methyl-2- (2-hydroxyphenyl) -2-methoxyacetic acid amide. Reference Example 2 (E) -1-chloro-3- (p-tolyl) -but-2-
Production of ene a) 10 g of 4-bromotoluene was dissolved in 50 ml of THF and cooled to -40 ° C. To this was added 38 ml of 1.6 M n-butyllithium hexane solution. Once the reaction solution is 0 ℃
After the temperature was raised to 1, the mixture was cooled to -70 ° C and stirred for 30 minutes. 4.5 g of methyl vinyl ketone was added dropwise to this. Then, after stirring at -70 ° C for 30 minutes, the mixture was allowed to cool to room temperature.
125 ml of 1N hydrochloric acid was added to the reaction solution, and ether (200 ml) was added.
X2) and after drying over anhydrous magnesium sulfate,
Concentrate under reduced pressure to give 3-hydroxy-3- (p
8.7 g of crude product of -tolyl) -but-1-ene were obtained. b) Obtained crude 3-hydroxy-3- (p-tolyl)-
30 ml of concentrated hydrochloric acid was added to 8.7 g of but-1-ene, and the mixture was stirred at room temperature for 1 hour. After cooling the reaction solution, add 100 ml of water,
The mixture was extracted with ether (100 ml × 2), the ether layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an oily residue. This is concentrated under reduced pressure to (E) -1-
7.9 g of chloro-3- (p-tolyl) -but-2-ene
Obtained.
【００１２】次に製剤例を示す。なお部は重量部を表わ
す。 製剤例１ 本発明化合物（１）〜（13）の各々５０部、リグニンス
ルホン酸カルシウム３部、ラウリル硫酸ナトリウム２部
および合成含水酸化珪素４５部をよく粉砕混合して各々
の水和剤を得る。 製剤例２ 本発明化合物（１）〜（13）の各々２５部、ポリオキシ
エチレンソルビタンモノオレエート３部、ＣＭＣ３部お
よび水６９部を混合し、有効成分の粒度が５ミクロン以
下になるまで湿式粉砕して各々の懸濁剤を得る。 製剤例３ 本発明化合物（１）〜（13）の各々２部、カオリンクレ
ー８８部およびタルク１０部をよく粉砕混合して各々の
粉剤を得る。 製剤例４ 本発明化合物（１）〜（13）の各々２０部、ポリオキシ
エチレンスチリルフェニルエーテル１４部、ドデシルベ
ンゼンスルホン酸カルシウム６部、およびキシレン６０
部をよく混合して各々の乳剤を得る。 製剤例５ 本発明化合物（１）〜（13）の各々２部、合成含水酸化
珪素１部、リグニンスルホン酸カルシウム２部、ベント
ナイト３０部およびカオリンクレー６５部をよく粉砕混
合し、水を加えてよく練り合わせた後、造粒乾燥して各
々の粒剤を得る。 製剤例６ 本発明化合物（１）〜（13）の各々１０部をキシレン３
５部およびジメチルホルムアミド３５部に溶解し、ポリ
オキシエチレンスチリルフェニルエーテル１４部、ドデ
シルベンゼンスルホン酸カルシウム６部を加え、よく攪
拌混合して各々の１０％乳剤を得る。Next, formulation examples are shown. The parts are parts by weight. Formulation Example 1 50 parts of each of the compounds (1) to (13) of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain each wettable powder. . Formulation Example 2 25 parts of each of the compounds (1) to (13) of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water are mixed and wet until the particle size of the active ingredient is 5 microns or less. Grind to obtain each suspension. Formulation Example 3 2 parts of each of the compounds (1) to (13) of the present invention, 88 parts of kaolin clay and 10 parts of talc are well pulverized and mixed to obtain each powder. Formulation Example 4 20 parts of each of the compounds (1) to (13) of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and xylene 60.
The parts are mixed well to obtain each emulsion. Formulation Example 5 2 parts of each of the compounds (1) to (13) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are well pulverized and mixed, and water is added. After thoroughly kneading, granulate and dry to obtain each granule. Formulation Example 6 10 parts of each of the compounds (1) to (13) of the present invention was mixed with xylene 3
After dissolving in 5 parts and 35 parts of dimethylformamide, 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzene sulfonate are added and mixed well with stirring to obtain 10% emulsions of each.
【００１３】次に本発明化合物が植物病害防除剤として
有用であることを試験例で示す。なお本発明化合物は表
３の化合物番号で示し、比較対照に用いた化合物は表４
の化合物記号で示す。Next, it is shown in Test Examples that the compound of the present invention is useful as a plant disease controlling agent. The compounds of the present invention are shown by the compound numbers in Table 3, and the compounds used for comparison and control are shown in Table 4.
The compound symbol is shown.
【表４】 また防除効力は、調査時の供試植物の発病状態すなわち
葉、茎等の菌叢、病斑の程度を肉眼観察し、菌叢、病斑
が全く認められなければ「５」、１０％程度認められれ
ば「４」、３０％程度認められれば「３」、５０％程度
認められれば「２」、７０％程度認められれば「１」、
それ以上で化合物を供試していない場合の発病状態と差
が認められなければ「０」として、６段階に評価し、そ
れぞれ５、４、３、２、１、０で示す。[Table 4] Moreover, the control efficacy is "5", about 10% if the disease state of the test plant at the time of the survey, that is, the flora of leaves, stems, etc. If it is recognized, "4", if 30% is recognized, "3", if 50% is recognized, "2", if 70% is recognized, "1",
If there is no difference from the diseased state when the compound is not tested above that level, it is evaluated as "0" and evaluated on a scale of 6 and shown as 5, 4, 3, 2, 1, 0, respectively.
【００１４】試験例１ コムギ眼紋病防除試験（予防効
果） プラスチックポットに砂壌土を詰め、コムギ（農林７３
号）を播種し、温室内で１０日間育成した。製剤例４に
準じて乳剤にした供試薬剤を水で希釈して所定濃度に
し、それを前記コムギの幼苗の葉面に充分付着するよう
に茎葉散布した。散布後、前記コムギの幼苗の株元に眼
紋病菌の胞子懸濁液を接種した。接種後、１５℃、暗
黒、多湿下で２日間置いた後、照明、多湿下で１４日間
生育し、防除効力を調査した。その結果を表５および表
６に示す。Test Example 1 Wheat Eyebrush Control Test (Preventive Effect) A plastic pot was filled with sandy loam and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 10 days. The reagent solution emulsified according to Formulation Example 4 was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface of the wheat seedling. After spraying, the seedlings of the wheat seedlings were inoculated with a spore suspension of eye-spotting fungi. After inoculation, the mixture was left for 2 days at 15 ° C. in the dark and in high humidity, and then grown for 14 days in lighting and high humidity, and the control efficacy was investigated. The results are shown in Tables 5 and 6.
【表５】 [Table 5]
【表６】 [Table 6]
【００１５】試験例２ コムギうどんこ病防除試験（治
療効果） プラスチックポットに砂壌土を詰め、コムギ（農林７３
号）を播種し、温室内で１０日間育成した。第２葉が展
開したそのコムギの幼苗にコムギうどんこ病菌の胞子を
ふりかけて接種した。接種後１５℃のグロースルームで
２日間育成したのち、製剤例４に準じて乳剤にした供試
化合物を水で希釈して所定濃度にし、それを前記コムギ
の葉面に充分付着するように茎葉散布した。散布後、１
５℃のグロースルームで６日間育成し防除効力を調査し
た。その結果を表７に示す。Test Example 2 Wheat Powdery Mildew Control Test (Therapeutic Effect) A plastic pot was filled with sandy loam and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 10 days. The wheat seedlings developed by the second leaf were sprinkled with spores of wheat powdery mildew and inoculated. After inoculation, the plant was grown in a growth room at 15 ° C. for 2 days, and then the test compound, which was made into an emulsion according to Formulation Example 4, was diluted with water to a predetermined concentration, and the leaves were stalked so as to adhere sufficiently to the leaf surface of the wheat. Sprayed. After spraying, 1
It was grown in a growth room at 5 ° C for 6 days, and the control efficacy was investigated. The results are shown in Table 7.
【表７】 [Table 7]
【００１６】試験例３ コムギさび病防除試験（予防効
果） プラスチックポットに砂壌土を詰め、コムギ（農林７３
号）を播種し、温室内で１０日間育成した。製剤例６に
準じて乳剤にした供試化合物を水で希釈して所定濃度に
し、第２葉が展開したそのコムギの幼苗に茎葉散布し
た。風乾後、コムギさび病菌の胞子を接種し、２３℃、
暗黒、多湿条件で１昼夜保ち、次いで２３℃照明下で６
日間育成したのち、防除効力を調べた。その結果を表８
に示す。Test Example 3 Wheat Rust Control Control Test (Preventive Effect) A plastic pot was filled with sandy loam and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 10 days. The test compound emulsified according to Formulation Example 6 was diluted with water to a predetermined concentration and sprayed on the wheat seedlings on which the second leaves had spread. After air-drying, inoculate with spores of wheat rust disease, 23 ℃,
Keep in the dark and high humidity for one day and night, then 6 at 23 ℃.
After growing for a day, the control efficacy was examined. The results are shown in Table 8
Shown in.
【表８】 [Table 8]
【００１７】試験例４ コムギ葉枯病防除試験（予防効
果） プラスチックポットに砂壌土を詰め、コムギ（農林７３
号）を播種し、温室内で８日間育成した。製剤例６に準
じて乳剤にした供試薬剤を水で希釈して所定濃度にし、
それをそのコムギの幼苗の葉面に充分付着するように茎
葉散布した。散布後、葉枯病菌の胞子懸濁液を噴霧接種
した。接種後、１５℃、暗黒、多湿下で３日間置き、さ
らに１５℃照明下で１８日間生育させて、防除効力を調
査した。その結果を表９および表１０に示す。Test Example 4 Wheat Leaf Blight Control Test (Preventive Effect) A plastic pot was filled with sandy loam and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 8 days. Emulsifying the test reagent according to Formulation Example 6 is diluted with water to a predetermined concentration,
The foliage was sprayed so that it adhered sufficiently to the leaf surface of the wheat seedling. After spraying, a spore suspension of leaf blight fungus was spray-inoculated. After inoculation, the plant was left for 3 days at 15 ° C. in the dark and in high humidity, and further grown for 18 days under illumination at 15 ° C., and the control efficacy was investigated. The results are shown in Tables 9 and 10.
【表９】 [Table 9]
【表１０】 [Table 10]
【００１８】試験例５ ブドウうどんこ病防除試験（予
防効果） プラスチックポットに砂壌土を詰め、ブドウ（ベリー
Ａ）を播種し、温室内で１ケ月半育成した。製剤例２に
準じて懸濁剤にした供試薬剤を水で希釈して所定濃度に
し、それをそのブドウの幼苗の葉面に充分付着するよう
に茎葉散布した。散布後、植物を風乾し、うどんこ病菌
の胞子懸濁液を噴霧接種した。接種後、２５℃の温室で
１４日間育成し、防除効力を調査した。その結果を表１
１に示す。Test Example 5 Grape Powdery Mildew Control Test (Preventive Effect) A plastic pot was filled with sandy loam soil, seeded with grape (berry A), and grown in a greenhouse for one and a half months. The reagent solution made into a suspension according to Formulation Example 2 was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface of the seedling of the grape. After spraying, the plants were air-dried and spray-inoculated with a spore suspension of powdery mildew. After inoculation, the plants were grown in a greenhouse at 25 ° C for 14 days, and the control efficacy was investigated. The results are shown in Table 1.
Shown in 1.
【表１１】 [Table 11]
【００１９】試験例６ トマト疫病防除試験（予防効
果） プラスチックポットに砂壌土を詰め、トマト（ポンテロ
ーザ）を播種し、温室内で２０日間栽培した。製剤例２
に準じて懸濁剤にした供試薬剤を水で希釈して所定濃度
にし、それをそのトマトの幼苗の葉面に充分付着するよ
うに茎葉散布した。散布後トマト疫病菌の胞子を接種
し、２０℃の湿室に１日保ち、次いで温室で５日間保っ
た後、防除効力を調べた。その結果を表１２および表１
３に示す。Test Example 6 Tomato Late Blight Control Test (Preventive Effect) A plastic pot was filled with sandy loam soil, seeded with tomato (ponterosa), and cultivated in a greenhouse for 20 days. Formulation example 2
The reagent solution prepared as a suspension according to 1. was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface of the tomato seedlings. After spraying, spores of Phytophthora infestans were inoculated, kept in a humid chamber at 20 ° C. for 1 day, and then kept in a greenhouse for 5 days, and then the control efficacy was examined. The results are shown in Table 12 and Table 1.
3 shows.
【表１２】 [Table 12]
【表１３】 [Table 13]
【００２０】[0020]
【発明の効果】本発明化合物は優れた植物病害防除効果
を示す。The compound of the present invention exhibits an excellent effect of controlling plant diseases.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 高野 仁孝 兵庫県宝塚市高司４丁目２番１号 住友化 学工業株式会社内 (72)発明者 松永 礼 兵庫県宝塚市高司４丁目２番１号 住友化 学工業株式会社内 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Yoshitaka Takano 4-2-1 Takashi Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Rei Matsunaga 4-2-1 Takashi Takarazuka-shi, Hyogo Prefecture Sumitomo Chemical Co., Ltd.
Claims (3)
よびＲ3 は同一または相異なり水素原子またはＣ1 −Ｃ
4 アルキル基を表わす。Ｒ4 はメチル基またはエチル基
を表わす。ＸはＣ1 −Ｃ4 アルキル基、Ｃ2 −Ｃ4 アル
ケニル基、Ｃ2 −Ｃ4 アルキニル基、Ｃ1 −Ｃ4 ハロア
ルキル基、Ｃ1 −Ｃ4 アルコキシ基、Ｃ3−Ｃ4 アルケ
ニルオキシ基、Ｃ3 −Ｃ4 アルキニルオキシ基、Ｃ1 −
Ｃ4 ハロアルコキシ基、Ｃ1 −Ｃ4 アルキルチオ基、Ｃ
1 −Ｃ4 ハロアルキルチオ基、Ｃ3−Ｃ8 シクロアルキ
ル基またはハロゲン原子を表わす。ｎは０〜３の整数を
表わす。ｎが２または３を表わすとき、Ｘは同一でも相
異なっていてもよい。〕で示されるアミド化合物。1. A general formula: ## STR1 ## [In the formula, R 1 represents a C 1 -C 4 alkyl group, R 2 and R 3 are the same or different and are a hydrogen atom or C 1 -C
4 represents an alkyl group. R 4 represents a methyl group or an ethyl group. X is C 1 -C 4 alkyl group, C 2 -C 4 alkenyl group, C 2 -C 4 alkynyl group, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, C 3 -C 4 alkenyloxy group , C 3 -C 4 alkynyloxy group, C 1-
C 4 haloalkoxy group, C 1 -C 4 alkylthio group, C
1 -C 4 haloalkylthio group, a C 3 -C 8 cycloalkyl group or a halogen atom. n represents an integer of 0 to 3. When n represents 2 or 3, X may be the same or different. ] The amide compound shown by these.
Ｒ2 が水素原子であり、ＸがＣ1 −Ｃ4 アルキル基、フ
ッ素原子、塩素原子またはトリフルオロメチル基であ
り、ｎが０〜２の整数である、請求項１記載のアミド化
合物。2. R 1 , R 3 and R 4 are methyl groups,
The amide compound according to claim 1, wherein R 2 is a hydrogen atom, X is a C 1 -C 4 alkyl group, a fluorine atom, a chlorine atom or a trifluoromethyl group, and n is an integer of 0 to 2.
効成分として含有することを特徴とする植物病害防除
剤。3. A plant disease controlling agent comprising the amide compound according to claim 1 or 2 as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17519793A JPH0725840A (en) | 1993-07-15 | 1993-07-15 | Amide compound and plant disease injury controlling agent containing the same as active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17519793A JPH0725840A (en) | 1993-07-15 | 1993-07-15 | Amide compound and plant disease injury controlling agent containing the same as active ingredient |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0725840A true JPH0725840A (en) | 1995-01-27 |
Family
ID=15991997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17519793A Pending JPH0725840A (en) | 1993-07-15 | 1993-07-15 | Amide compound and plant disease injury controlling agent containing the same as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0725840A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003014066A3 (en) * | 2001-08-06 | 2003-11-27 | Bayer Cropscience Ag | Method for producing 2-(hydroxyphenyl)-2-(alkoxyimino)-n-methylacetamide derivatives |
-
1993
- 1993-07-15 JP JP17519793A patent/JPH0725840A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003014066A3 (en) * | 2001-08-06 | 2003-11-27 | Bayer Cropscience Ag | Method for producing 2-(hydroxyphenyl)-2-(alkoxyimino)-n-methylacetamide derivatives |
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