JPH07610B2 - Novel isoquinoline derivative - Google Patents
Novel isoquinoline derivativeInfo
- Publication number
- JPH07610B2 JPH07610B2 JP13976286A JP13976286A JPH07610B2 JP H07610 B2 JPH07610 B2 JP H07610B2 JP 13976286 A JP13976286 A JP 13976286A JP 13976286 A JP13976286 A JP 13976286A JP H07610 B2 JPH07610 B2 JP H07610B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- isoquinoline
- disease
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 [産業上の利用分野] この発明は新規なイソキノリン誘導体に関するものであ
る。そして、この化合物は農園芸用殺菌剤又はその中間
体として有用である。TECHNICAL FIELD The present invention relates to a novel isoquinoline derivative. And this compound is useful as an agricultural / horticultural germicide or its intermediate.
[従来の技術] イソキノリン四級塩の1位での付加反応としては種々の
報告、例えば、N−ベンゾイルイソキノリン四級塩(W.
E.McEwen etal.,Chem.Rev.,55,511(1955))、N−ベン
ジルイソキノリン四級塩(F.Brohnke,etal.,Chem.Ber.,
90,227(1957))あるいはN−メチルイソキノリン四級塩
(N.J.Leon ard etal.,J.Am.Chem.Soc.,71,3405(194
9))等が知られているが、N−アルキルイソキノリン四
級塩に関しては上記N−メチルの場合を除いてほとんど
知られていない。[Prior Art] Various reports on the addition reaction at the 1-position of an isoquinoline quaternary salt, for example, N-benzoylisoquinoline quaternary salt (W.
E.McEwen et al., Chem. Rev., 55 , 511 (1955)), N-benzylisoquinoline quaternary salt (F. Brohnke, et al., Chem. Ber.,
90, 227 (1957)) or N- methyl isoquinoline quaternary salt (NJLeon ard etal., J.Am.Chem.Soc. , 71, 3405 (194
9)) and the like are known, but little is known about N-alkylisoquinoline quaternary salts except for the above N-methyl.
また、特開昭59-219,203号公報は1,2,3,4−テトラヒド
ロイソキノリン誘導体を、また、特開昭59-219,204号公
報は1,2,3,4−テトラヒドロイソキノリニウム塩誘導体
をそれぞれ開示しているが、そのいずれもイソキノリン
の1−置換体を開示するものではない。Further, JP-A-59-219,203 discloses a 1,2,3,4-tetrahydroisoquinoline derivative, and JP-A-59-219,204 discloses a 1,2,3,4-tetrahydroisoquinolinium salt derivative. However, none of them discloses 1-substituted isoquinoline.
[発明が解決しようとする問題点] 本発明は、上記特開昭59-219,203号及び特開昭59-219,2
03号の各公報に記載されているようなイソキノリン誘導
体がある種の細菌や糸状菌による病害に対して有効性を
有するという知見に基いて創案されたもので、農園芸用
殺菌剤又はその中間体として有用な新規なイソキノリン
誘導体を提供することを目的とするものであり、特にイ
ソキノリン骨格の1−位にインドール骨格が付加した新
規なイソキノリン化合物を提供することを目的とするも
のである。[Problems to be Solved by the Invention] The present invention relates to the above-mentioned JP-A-59-219,203 and JP-A-59-219,2.
It was created based on the finding that the isoquinoline derivative as described in each of the 03 publications is effective against disease caused by certain bacteria and filamentous fungi. It is an object of the present invention to provide a novel isoquinoline derivative useful as a body, and particularly to provide a novel isoquinoline compound having an indole skeleton added to the 1-position of the isoquinoline skeleton.
[問題点を解決するための手段] すなわち、本発明は、下記一般式(I)又は(II)(但
し、式中Xはアルキル基、ハロゲン又はニトロ基を示
し、Yはアルキル基、ハロゲン、ニトロ基、アミノ基、
ヒドロキシ基又はカルボキシ基を示し、Rはアルキル基
を示し、m及びnは0〜2の整数である。) で表されるイソキノリン誘導体である。[Means for Solving Problems] That is, the present invention provides the following general formula (I) or (II) (wherein X represents an alkyl group, a halogen or a nitro group, and Y represents an alkyl group, a halogen, Nitro group, amino group,
It represents a hydroxy group or a carboxy group, R represents an alkyl group, and m and n are integers from 0 to 2. ) It is an isoquinoline derivative represented by.
本発明のイソキノリン誘導体において、上記一般式
(I)及び(II)中の置換基Xはそれがハロゲンである
場合塩素又は臭素が好ましく、それがアルキル基である
場合メチル基が好ましく、また、その置換位置について
はイソキノリン骨格の3〜8位であり、さらに、この置
換基Xはそれが2個存在する場合互いに同じ置換基であ
っても、異なる置換基であってもよい。また、置換基Y
については、それがアルキル基である場合メチル基が好
ましく、ハロゲンである場合塩素又は臭素が好ましく、
また、その置換位置についてはインドール骨格の2−位
及び/又は4〜7位であり、さらに、置換基Yはそれが
2個存在する場合互いに同じ置換基であっても、異なる
置換基であってもよい。さらに、置換基Rは好ましくは
炭素数1〜20のアルキル基であり、このアルキル基につ
いてはその置換基中にヒドロキシ基、アルコキシ基等の
酸素含有基を含むものであってもよく、またエチレン結
合等の不飽和結合を含むものであってもよい。In the isoquinoline derivative of the present invention, the substituent X in the above general formulas (I) and (II) is preferably chlorine or bromine when it is a halogen, and is preferably a methyl group when it is an alkyl group. The substitution position is 3 to 8 positions of the isoquinoline skeleton, and when two substituents X are present, they may be the same or different substituents. In addition, the substituent Y
For, a methyl group is preferred when it is an alkyl group, chlorine or bromine is preferred when it is a halogen,
Further, the substitution position is 2-position and / or 4- to 7-position of the indole skeleton, and when two substituents Y are present, they may be the same substituent or different substituents. May be. Further, the substituent R is preferably an alkyl group having 1 to 20 carbon atoms, and the alkyl group may have an oxygen-containing group such as a hydroxy group and an alkoxy group in the substituent, and ethylene. It may contain an unsaturated bond such as a bond.
上記一般式(I)及び(II)で示される本発明の化合物
は、例えば、以下の方法によって製造することができ
る。The compounds of the present invention represented by the above general formulas (I) and (II) can be produced, for example, by the following method.
すなわち、先ずイソキノリンの核窒素原子をアルキルハ
ライド等のアルキル化剤でアルキル化してN−アルキル
イソキノリニウム塩を製造し、このN−アルキルイソキ
ノリニウム塩をアルカリの存在下にインドールと反応さ
せ、得られた反応混合物有機溶剤で抽出し、水洗して未
反応物を除去した後、乾燥し溶剤を除去して目的物であ
る一般式(II)の化合物を得る。That is, first, a nuclear nitrogen atom of isoquinoline is alkylated with an alkylating agent such as an alkyl halide to produce an N-alkylisoquinolinium salt, and the N-alkylisoquinolinium salt is reacted with indole in the presence of an alkali. Then, the obtained reaction mixture is extracted with an organic solvent, washed with water to remove unreacted materials, and then dried to remove the solvent to obtain the desired compound of the general formula (II).
次に、このようにして得られた一般式(II)の化合物を
例えばナトリウムボロハイドライドによる水素化や白金
触媒の存在下での接触水素化により水素化し、目的物の
一般式(I)で示される化合物を製造する。Next, the compound of the general formula (II) thus obtained is hydrogenated by, for example, hydrogenation with sodium borohydride or catalytic hydrogenation in the presence of a platinum catalyst to give the compound represented by the general formula (I). To produce the compound.
このようにして得られた本発明のイソキノリン誘導体
は、農業や園芸等における作物栽培上多大な被害を与え
ている種々の病原菌に対して有効である。本発明化合物
によって防除される病害としては、多くの病害を挙げる
ことができるが、代表的には細菌性病害であるみかん潰
瘍病(Xanthomonas citri)、稲白葉枯病(Xanthomonas
oryzae)、きゅうり斑点細菌病(Pseudomonas lachrym
-ans)、カンラン軟腐病(Erwinia aroideae)等や、糸
状菌性病害である稲ごま葉枯病(Cochlioboluamiyabean
ua)、稲いもち病(Piricularia oryzae)、みかん黒点
病(Diaporthe citri)、りんご斑点枯葉病(Alternari
a mali)、きゅうり疫病(Phytophthora parasitic
a)、トマト炭そ病(Glomerella phomoides)等を挙げ
ることができる。なかでも、本発明化合物は、みかんの
重要病害であって同時に防除することが困難な細菌性み
かん潰瘍病と糸状菌性みかん黒点病とに対して同時に著
効を奏し、個々の病害に対して別個に薬剤散布を行う必
要がなくなり、作業簡易化の面から極めて有用である。
なお、本発明化合物は、殺ダニ剤等の殺虫剤としての作
用も有するので、この目的で使用することもできる。The isoquinoline derivative of the present invention obtained in this manner is effective against various pathogenic bacteria which cause great damage in crop cultivation in agriculture, horticulture and the like. As the disease controlled by the compound of the present invention, many diseases can be mentioned, but typically, tangerine ulcer disease (Xanthomonas citri), which is a bacterial disease, and rice leaf blight (Xanthomonas)
oryzae), cucumber spot bacterial disease (Pseudomonas lachrym)
-ans), kanlan soft rot (Erwinia aroideae), etc., and rice sesame leaf blight (Cochliobolua miyabean), which is a filamentous fungal disease.
ua), rice blast (Piricularia oryzae), mandarin orange spot (Diaporthe citri), apple spot blight (Alternari)
a mali), Cucumber plague (Phytophthora parasitic)
a) and tomato anthracnose (Glomerella phomoides). Among them, the compound of the present invention is a significant disease of mandarin oranges, and it is difficult to control at the same time, and simultaneously exerts a remarkable effect against bacterial mandarin orange ulcer disease and filamentous fungal mandarin orange spot disease, and against individual diseases. It is not necessary to separately spray the medicine, which is extremely useful in terms of work simplification.
Since the compound of the present invention also has an action as an insecticide such as acaricide, it can be used for this purpose.
本発明化合物は、これを農業用殺菌剤として使用する場
合、界面活性剤、溶剤、希釈剤、分散剤、乳化剤、湿潤
剤、接着剤、シックナー、肥料、その他の液体又は固体
の担体と共に製剤することにより、農薬として使用し易
い製剤形態にして使用できるもので、この製剤形態とし
ては、例えば、水和剤、乳剤、水溶剤、粉剤、水面拡散
性油剤、粒剤等を挙げることができ、いずれの製剤形態
であっても使用できるものである。When used as an agricultural fungicide, the compounds of the present invention are formulated with surfactants, solvents, diluents, dispersants, emulsifiers, wetting agents, adhesives, thickeners, fertilizers and other liquid or solid carriers. As a result, it can be used in the form of a formulation that is easy to use as an agricultural chemical, and examples of the form of the formulation include wettable powders, emulsions, water solvents, powders, water-diffusing oils, granules, and the like. Any formulation form can be used.
[実施例] 以下、実施例、製剤例及び試験例に基いて、本発明を説
明する。[Examples] The present invention will be described below based on Examples, Formulation Examples and Test Examples.
I.実施例 実施例1 〔一般式(II)で示される化合物の製造〕 第1表に示すイソキノリン類(39mmole)と第1表に示
すアルキルハライド(43mmole)とをジメチルホルムア
ミド5ml中に溶解し、150℃で5時間反応させた。ガラス
チューブオーブンを使用して反応混合物中のジメチルホ
ルムアミドを減圧留去し、残留分をイソプロピルエーテ
ルで洗浄して第1表に示す収率でアルキルイソキノリニ
ウム塩を得た。I. Examples Example 1 [Production of compounds represented by the general formula (II)] Isoquinolines (39 mmole) shown in Table 1 and alkyl halides (43 mmole) shown in Table 1 were dissolved in 5 ml of dimethylformamide. The mixture was reacted at 150 ° C for 5 hours. Dimethylformamide in the reaction mixture was distilled off under reduced pressure using a glass tube oven, and the residue was washed with isopropyl ether to obtain an alkylisoquinolinium salt in a yield shown in Table 1.
得られたアルキルイソキノリニウム塩3gと精製インドー
ル(対アルキルイソキノリニウム塩モル比0.9)とをア
セトニトリル30ml中に溶解し、室温ないし水冷下で攪拌
しながらアルキルイソキノリニウム塩に対して等モルの
10wt%−水酸化カリウム水溶液を滴下し、30〜60分間反
応させた後、反応混合物を分液ロートに移し、上層のア
セトニトリル層と下層の水層との間に遊離した油層を分
取し、これをジクロルメタン又はクロロホルムに溶解し
て水洗し、次いで硫酸ソーダで乾燥した後、40℃以下の
温度で溶媒を除去し、目的物の一般式(II)で示される
生成物を得た。得られた生成物はそのいずれも赤褐色の
粘稠なグリース状であった。また、この一般式(II)で
示される生成物の粗収率及び純度並びにイソキノリン骨
格の2−位のN原子に結合したアルキル基のメチレン水
素の1H‐NMRのケミカルシフト(δ:ppm)を第1表に示
す。3 g of the obtained alkylisoquinolinium salt and purified indole (to a molar ratio of alkylisoquinolinium salt of 0.9) were dissolved in 30 ml of acetonitrile, and the mixture was stirred at room temperature or under water cooling with respect to the alkylisoquinolinium salt. Equimolar
10 wt% -potassium hydroxide aqueous solution was added dropwise, and after reacting for 30 to 60 minutes, the reaction mixture was transferred to a separating funnel, and an oil layer separated between the upper acetonitrile layer and the lower aqueous layer was separated, This was dissolved in dichloromethane or chloroform, washed with water, dried over sodium sulfate, and then the solvent was removed at a temperature of 40 ° C. or lower to obtain the desired product of the general formula (II). Each of the obtained products was a reddish brown viscous grease. Further, the crude yield and purity of the product represented by the general formula (II) and the chemical shift (δ: ppm) of 1 H-NMR of methylene hydrogen of the alkyl group bonded to the N atom at the 2-position of the isoquinoline skeleton Is shown in Table 1.
さらに、上記第1表に示された化合物No.4と11とについ
て、より詳細な1H‐NMR、13C‐NMR及びマススペクトル
による分析結果を第2表に示す。なお、この第2表にお
いて、1H‐NMR及び13C‐NMRにおけるαはイソキノリン
骨格のN原子に結合した炭素の位置を、はイソキノリ
ン骨格の1−位を、はイソキノリン骨格の3−位を、
はイソキノリン骨格の4−位を、また、′はインド
ール骨格の2−位をそれぞれ示す。Further, Table 2 shows more detailed 1 H-NMR, 13 C-NMR and mass spectrum analysis results of the compounds Nos. 4 and 11 shown in Table 1 above. In Table 2, α in 1 H-NMR and 13 C-NMR is the position of the carbon bonded to the N atom of the isoquinoline skeleton, is the 1-position of the isoquinoline skeleton, and is the 3-position of the isoquinoline skeleton. ,
Indicates the 4-position of the isoquinoline skeleton, and ′ indicates the 2-position of the indole skeleton.
また、アルキルイソキノリニウム塩としてラウリルイソ
キノリニウムクロライドを使用し、精製インドールに代
えて第3表に示すインドール誘導体を使用し、また、生
成物を四塩化炭素で抽出してクロマト分離した後、常温
蒸溜後減圧乾燥して精製した以外は、上記と同様にして
一般式(II)で示される化合物を製造した。得られた生
成物の収率とその性状を第3表に示す。Also, laurylisoquinolinium chloride was used as the alkylisoquinolinium salt, the indole derivative shown in Table 3 was used in place of the purified indole, and the product was extracted with carbon tetrachloride for chromatographic separation. Then, a compound represented by the general formula (II) was produced in the same manner as above, except that the compound was distilled at room temperature and then dried under reduced pressure for purification. The yield of the obtained product and its properties are shown in Table 3.
実施例2 〔一般式(I)で示される化合物の製造〕 第4表に示すアルキル基RのN−アルキルイソキノリニ
ウムハライドと精製インドールとをメタノール又はアセ
トニトリル中に溶解し、この溶液中に28wt%‐CH3ONaメ
タノール溶液又は10%‐KOH水溶液を加え、約2日間反
応させた。得られた反応混合物から溶媒を留去し、残分
をアンバーリスト処理し、次いでNaBH4で還元した。そ
の後、反応生成物をシリカゲルカラム(溶離液クロロホ
ルム)で精製し、第4表に示す置換基X、Y及びRの一
般式(I)化合物を得た。得られた生成物はそのいずれ
も黄褐色オイル状であり、その収率及び性状を第4表
に、また、化合物No.22及び23のものについての13C‐NM
R及びマススペクトルによる分析結果を第5表にそれぞ
れ示す。なお、13C‐NMRのデータにおけるα、、及
びは第2表の場合と同じであり、また、′はインド
ール骨格の3−位の位置を示す。 Example 2 [Production of Compound Represented by General Formula (I)] N-alkylisoquinolinium halide of alkyl group R shown in Table 4 and purified indole were dissolved in methanol or acetonitrile, and dissolved in this solution. A 28 wt% CH 3 ONa methanol solution or a 10% KOH aqueous solution was added, and the reaction was carried out for about 2 days. The solvent was distilled off from the resulting reaction mixture, the residue was amberlysted and then reduced with NaBH 4 . Then, the reaction product was purified by a silica gel column (eluent chloroform) to obtain a compound of the general formula (I) having the substituents X, Y and R shown in Table 4. The obtained products were all in the form of yellowish brown oils, and the yields and properties are shown in Table 4. Also, 13 C-NM of compound Nos. 22 and 23 were used.
The results of analysis by R and mass spectra are shown in Table 5, respectively. In the 13 C-NMR data, α, and are the same as in Table 2, and ′ indicates the 3-position of the indole skeleton.
II.製剤例 (1)乳剤 No.1の化合物 10.0重量部 キシロール 86.5重量部 エマルゲン909 (花王石鹸(株)製商品名) 2.0重量部 ネオペレックスC70 (花王石鹸(株)製商品名) 1.5重量部 上記各薬剤を均一に攪拌混合して乳剤を調製し、使用に
際しては水で希釈しあるいはそのまま使用する。 II. Formulation Example (1) Emulsion No. 1 compound 10.0 parts by weight Xylol 86.5 parts by weight Emulgen 909 (Kao Soap Co., Ltd. trade name) 2.0 parts by weight Neoperex C70 (Kao Soap Co., Ltd. trade name) 1.5 parts by weight Parts The above agents are uniformly mixed with stirring to prepare an emulsion, which is diluted with water or used as it is.
(2)水和剤 No.11の化合物 20.0重量部 ネオペレックスNo6F (花王石鹸(株)製商品名) 3.0重量部 ソルポール8070 (東邦化学(株)製商品名) 4.0重量部 ホワイトカーボン 5.0重量部 クレー 68.0重量部 上記薬剤を均一に粉砕混合して水和剤を調製し、使用に
際しては水で希釈して施してもよく、また、土壌と混合
して使用してもよい。(2) Wettable powder No. 11 compound 20.0 parts by weight Neoperex No6F (Kao Soap Co., Ltd. product name) 3.0 parts by weight Solpol 8070 (Toho Chemical Co., Ltd. product name) 4.0 parts by weight White carbon 5.0 parts by weight Clay 68.0 parts by weight The above chemicals may be uniformly pulverized and mixed to prepare a wettable powder, which may be diluted with water before use, or may be mixed with soil before use.
(3)粉剤 No.15の化合物 5.0重量部 タルク 95.0重量部 上記各薬品を均一に粉砕混合して粉剤を調製し、使用に
際してはそのままあるいは土壌と混合して使用する。(3) Powder No. 15 compound 5.0 parts by weight Talc 95.0 parts by weight The above chemicals are uniformly pulverized and mixed to prepare a powder, which is used as it is or after mixing with soil.
III.試験例 (No.−1)稲ごま葉枯病苗鉢試験 1,000ppm濃度の薬液を稲(品種:トネワセ)苗鉢に充分
散布し、風乾1日後に稲ごま葉枯病菌の胞子懸濁液(胞
子濃度(倍率150倍):1視野当り6〜8個)を噴霧して
接種し、25℃の湿室内で24時間放置し、1週間後に1葉
当りの病斑数を数え、A:抑制率95%以上、B:抑制率50〜
95%及びC:抑制率50%以下の3段階で評価した。結果を
第6表に示す。III. Test example (No.-1) Rice sesame leaf blight disease seedling test A 1000ppm concentration drug solution is filled and dispersed in rice (cultivar: Tonawase) seedlings, and one day after air-drying, spore suspension of rice sesame leaf blight fungus A liquid (spore concentration (magnification: 150 times): 6 to 8 per field of view) is sprayed and inoculated, left in a humid chamber at 25 ° C for 24 hours, and one week later, the number of lesions per leaf is counted. : Suppression rate 95% or more, B: Suppression rate 50 ~
95% and C: Suppression rate was 50% or less. The results are shown in Table 6.
(No.−2)きゅうり疫病葉片試験 1,000ppm濃度の薬液をきゅうり(品種:相模半白)の葉
裏に充分散布し、風乾1日後に予めきゅうり果実で培養
したきゅうり疫病菌の遊走子のう10,000個/mlを1葉当
り2箇所に滴下して接種し、28℃の暗湿室内に保持して
2日後に調査し、A:菌の侵入認められず、B:接種部分の
一部で菌の侵入が認められるが、病斑は拡大せず、C:接
種部分全域で菌の侵入が認められるが、非接種部分への
病斑の拡大は認められず、及び、D:病斑が非接種部分ま
で拡大し、無処理の場合と同等である、の4段階で評価
した。結果を第6表に示す。(No.-2) Cucumber epidemic leaf piece test A zoospore of a cucumber epidemic bacterium, which is prepared by cultivating a 1,000 ppm-concentrated drug solution on the underside of cucumber (cultivar: Sagamihanjiro) and culturing the cucumber fruit in advance one day after air-drying. Inoculate 10,000 leaves / ml at 2 spots per leaf, incubate in a dark room at 28 ° C and inspect 2 days later. A: No invasion of fungus was observed, B: Part of inoculated part Bacterial invasion is observed, but lesions do not spread, C: Bacterial invasion is observed throughout the inoculated area, but no lesions spread to non-inoculated areas, and D: lesions It was expanded to the non-inoculated part and evaluated in four stages, which is equivalent to the case of no treatment. The results are shown in Table 6.
(No.−3)かんきつ黒点病鉢試験 予めせん定を行って新葉を出させた夏柑実生苗鉢に1,00
0ppm濃度の薬液を充分散布し、風乾1日後にかんきつ黒
点病菌の胞子懸濁液(胞子濃度(倍率150倍):1視野当
り200個)を噴霧して接種し、27℃の接種箱に24時間入
れた後温室内で管理し、2〜3週間後に病斑数を数え、
発病葉率及び1葉当りの病斑数を求めてA:抑制率95%以
上、B:抑制率50〜95%及びC:抑制率50%以下の3段階で
評価した。結果を第6表に示す。(No.-3) Citrus sunspot mortar test 1,00 in a summer citrus seedling seedling that had been pruned beforehand to produce new leaves
A 1 ppm solution of 0 ppm concentration was applied and dispersed, and one day after air-drying, a spore suspension of citrus black spot spores (spore concentration (magnification: 150 times): 200 per field) was sprayed and inoculated. After putting in the time, manage in the greenhouse, count the number of lesions after 2-3 weeks,
The diseased leaf rate and the number of lesions per leaf were obtained and evaluated in three stages: A: inhibition rate of 95% or more, B: inhibition rate of 50 to 95%, and C: inhibition rate of 50% or less. The results are shown in Table 6.
(No.−4)稲ごま葉枯病苗鉢試験 第7表に示す濃度の薬液を稲(品種:トネワセ)苗鉢に
充分散布し、風乾1日後に稲ごま葉枯病菌の胞子懸濁液
(胞子濃度(倍率150倍):1視野当り6〜8個)を噴霧
して接種し、25℃の湿室内で24時間放置し、1週間後に
1葉当りの病斑数を数え、A:抑制率95%以上、B:抑制率
50〜95%及びC:抑制率50%以下の3段階で評価した。結
果を第7表に示す。(No.-4) Rice sesame leaf blight disease seedling test A chemical solution having the concentration shown in Table 7 was applied to rice (cultivar: Tonawase) seedlings and dispersed, and after 1 day of air drying, a spore suspension of rice sesame leaf blight fungus. (Spore concentration (magnification: 150 times): 6 to 8 per field of view) is sprayed and inoculated, left in a humid chamber at 25 ° C for 24 hours, and one week later, the number of lesions per leaf is counted, and A: Suppression rate 95% or more, B: Suppression rate
50 to 95% and C: Inhibition rate was 50% or less. The results are shown in Table 7.
(No.−5)かんきつ潰瘍病鉢試験 予めせん定を行って新葉を出させた夏柑実生苗鉢に第7
表に示す濃度の薬液を充分散布し、風乾1日後にかんき
つ潰瘍病菌の懸濁液(濃度:2×108cells/ml)を噴霧し
て接種し、27℃の湿室に24時間入れた後温室内で管理
し、2〜3週間後に病斑数を数え、発病葉率及び1葉当
りの病斑数を求めた。結果を第7表に示す。(No.-5) Citrus ulcer disease pot test No. 7 was applied to the summer seedling seedling pots that had been pruned beforehand to produce new leaves.
A solution of the concentration shown in the table was applied and dispersed, and after 1 day of air-drying, a suspension of citrus ulcer disease (concentration: 2 × 10 8 cells / ml) was sprayed and inoculated, and placed in a humid chamber at 27 ° C. for 24 hours. After management in a greenhouse, the number of lesions was counted 2 to 3 weeks later, and the diseased leaf rate and the number of lesions per leaf were determined. The results are shown in Table 7.
[発明の効果] 本発明の新規なイソキノリン誘導体は、そのままである
いは所定の製剤形態にして、農園芸用の殺菌剤、殺虫剤
等として使用することができるか、あるいは、その中間
体として使用することができ、極めて有用な化合物であ
る。 [Effects of the Invention] The novel isoquinoline derivative of the present invention can be used as it is or in a predetermined formulation form as a fungicide for agricultural and horticultural use, as an insecticide, or as an intermediate thereof. It is a very useful compound.
Claims (1)
示し、Yはアルキル基、ハロゲン、ニトロ基、アミノ
基、ヒドロキシ基又はカルボキシ基を示し、Rはアルキ
ル基を示し、m及びnは0〜2の整数である。)で表さ
れる新規なイソキノリン誘導体。1. The following general formula (I) or (II) (Wherein X represents an alkyl group, a halogen or a nitro group, Y represents an alkyl group, a halogen, a nitro group, an amino group, a hydroxy group or a carboxy group, R represents an alkyl group, and m and n are 0. Is an integer of 2).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13976286A JPH07610B2 (en) | 1986-06-16 | 1986-06-16 | Novel isoquinoline derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13976286A JPH07610B2 (en) | 1986-06-16 | 1986-06-16 | Novel isoquinoline derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62294679A JPS62294679A (en) | 1987-12-22 |
JPH07610B2 true JPH07610B2 (en) | 1995-01-11 |
Family
ID=15252797
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP13976286A Expired - Lifetime JPH07610B2 (en) | 1986-06-16 | 1986-06-16 | Novel isoquinoline derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH07610B2 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT1736471E (en) * | 2004-01-23 | 2014-03-25 | Mitsui Chemicals Agro Inc | 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines |
EP1723105B1 (en) | 2004-03-03 | 2013-05-15 | Eli Lilly And Company | Bicyclic substituted indole-derivative steroid hormone nuclear receptor modulators |
JP5208966B2 (en) * | 2007-12-26 | 2013-06-12 | 日本曹達株式会社 | Nitrogen-containing heterocyclic compounds and agricultural and horticultural fungicides |
EP3334715B1 (en) * | 2015-08-12 | 2019-05-22 | Syngenta Participations AG | Microbiocidal heterobicyclic derivatives |
BR112018002709B1 (en) * | 2015-08-12 | 2022-07-05 | Syngenta Participations Ag | COMPOUNDS, COMPOSITION AND METHOD OF COMBAT, PREVENTION OR CONTROL OF PHYTOPATOGENIC DISEASES INCLUDING SUCH COMPOUND |
-
1986
- 1986-06-16 JP JP13976286A patent/JPH07610B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPS62294679A (en) | 1987-12-22 |
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