JPS6011401A - Agricultural and horticultural fungicide containing alpha- cyanoketone derivative as active component - Google Patents
Agricultural and horticultural fungicide containing alpha- cyanoketone derivative as active componentInfo
- Publication number
- JPS6011401A JPS6011401A JP11688483A JP11688483A JPS6011401A JP S6011401 A JPS6011401 A JP S6011401A JP 11688483 A JP11688483 A JP 11688483A JP 11688483 A JP11688483 A JP 11688483A JP S6011401 A JPS6011401 A JP S6011401A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- group
- alkyl
- agricultural
- 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.)
- Pending
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は下記の一般式で表わされるα−シアノケトン類
及び誘導体を有効成分として含有する農園芸用殺菌剤に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an agricultural and horticultural fungicide containing α-cyanoketones and derivatives represented by the following general formula as active ingredients.
一般式
(但し、(1) 、 (II)共に、Rがアルキル基か
芳香族基でありしかも、RがC!、以上のアルキル基、
アラルキル基、芳香族基あるいは複素環基である化合物
および、Rが複素環基、置換フェノキシ基、置換チオフ
ェノキシ基のいづれかであシ、シかも、R2が水素、ア
ルキル基、芳香族基、複素環基のいずれかである化合物
を表し、Rはアルキル基、アシル基、カルバモイル基、
置換スルホニル基ヲ表−i。)本発明の化合物の例とし
て代表的なものを例示すれば、第1表に示すごときもの
が挙げられる。General formula (provided that in both (1) and (II), R is an alkyl group or an aromatic group, and R is C!, an alkyl group of the above,
Compounds where R is an aralkyl group, an aromatic group, or a heterocyclic group; Represents a compound that is any of a ring group, R is an alkyl group, an acyl group, a carbamoyl group,
Substituted sulfonyl group Table-i. ) Typical examples of the compounds of the present invention include those shown in Table 1.
尚、化合物の表示は前記一般式に於ける記号で示す。ま
た物性欄のNMRは核磁気共鳴スペクトル()内は溶媒
、mpは融点、η0は屈折率を示し、表示法は慣用の方
法に従った。In addition, the compound is indicated by the symbol in the above general formula. Further, in the physical properties column, NMR indicates the nuclear magnetic resonance spectrum () indicates the solvent, mp indicates the melting point, and η0 indicates the refractive index, and the display method was in accordance with the conventional method.
表1
本発明の化合物は次のようにして合成することができる
。Table 1 The compounds of the present invention can be synthesized as follows.
一般に、R’−CH2CNとR2とOC2H5とを塩基
性触媒で縮合することにより、(1)は得られる。R1
及びR2は体であり、(1)’を酸無水物、/・ロケ゛
ン化アルキル、イソシアネート類等と反応させることに
よシ得られる。Generally, (1) can be obtained by condensing R'-CH2CN, R2, and OC2H5 with a basic catalyst. R1
and R2 are bodies, which can be obtained by reacting (1)' with an acid anhydride, an alkyl fluoride, an isocyanate, or the like.
以下に代表的な合成例を示し、更に具体的に説明する。Typical synthesis examples are shown below and explained in more detail.
本発明化合物は広汎な農園芸作物の病害の防除に効果的
であり、その主なものを例示すれば以下のものが挙げら
れる。The compounds of the present invention are effective in controlling a wide range of diseases of agricultural and horticultural crops, and the main ones include the following.
水稲 いもち、ごま葉枯、紋枯、白葉枯病;麦 うどん
こ、斑点、さび、雪腐、菌核病;ジャガ芋 疫、裏皮、
黒あざ病;
豆類 褐斑、さび、斑点、べと、菌核病:タバコ 野火
、赤星、疫病:
茶 赤燐、もち、網もち、炭そ、輪斑病;ビート ベと
、褐斑、苗立枯病;
トマト かいよう、疫、灰色かび、葉かび、萎凋、菌核
、苗立枯、輪紋病;
キュウリ 灰色かび、べと、灰色疫、菌核、黒星、苗立
枯、炭そ、つる枯、つる割、うどんこ病;
大根 黒腐、軟腐、萎黄、黒斑、べと病;玉ネギ 軟腐
、べと、灰色腐敗、さび病;レタス 軟腐、菌核病;
カンキツ 灰色かび、かいよう、黒点、そうか病;リン
ゴ モニリア、黒星、斑点落葉病、うどんこ病;カキ
灰色かび、円層落葉、角斑落葉、炭そ病;ナシ 赤星、
黒星、黒斑病;
モモ 人里、黒星、フォモプレス腐敗、せん孔細菌病;
ブドウ ベと、黒痘、灰色かび、さび、うどんこ、晩腐
病等。Paddy rice: rice blast, sesame leaf blight, sheath blight, leaf blight; wheat: powdery mildew, spots, rust, snow rot, sclerotium; potato blight, back skin,
Black blight; Legumes Brown spot, rust, spot, downy mildew, Sclerotinia; Tobacco Wildfire, red star, late blight; Brown Red phosphorous, mochi, net mochi, anthracnose, ring spot; Beet Downy spot, downy mildew, seedlings Damping-off; Tomato: canker, blight, gray mold, leaf mold, wilt, sclerotia, seedling damping-off, ring spot disease; Cucumber Botrytis, downy mildew, gray blight, sclerotia, black star, seedling damping-off, anthracnose, Vine blight, vine splitting, powdery mildew; Radish black rot, soft rot, yellowing, black spot, downy mildew; Onion soft rot, mildew, gray rot, rust; Lettuce soft rot, sclerotia; Citrus gray mold, canker , black spot, scab; apple monilia, scab, leaf spot, powdery mildew; persimmon
Botrytis, round layer defoliation, horn spot defoliation, anthracnose; pear akaboshi,
Black star, black spot; peach, black star, fomopress rot, bacterial borer disease; grape downy mildew, black pox, gray mold, rust, powdery mildew, late rot, etc.
本発明の化合物は前述のごとく農園芸用殺菌剤として用
いられるが、そのまま或いは担体(希釈剤)と混合して
粉剤、粒剤、水利剤、乳剤、油剤その他農薬製剤上慣用
されている適当な剤として用いられる。この場合必要に
応じて展着剤、乳化剤、湿展剤、固着剤等が適宜用いら
れ、又他の種類の殺菌剤や殺虫剤除草剤、肥料等と併用
、混合することもできる。As mentioned above, the compound of the present invention can be used as a fungicide for agricultural and horticultural purposes, but it can be used as it is or mixed with a carrier (diluent) to form powders, granules, irrigation agents, emulsions, oils, and other suitable agrochemical preparations. used as an agent. In this case, spreading agents, emulsifiers, wetting agents, fixing agents, etc. are used as appropriate, and they can also be used in combination or mixed with other types of fungicides, insecticides, herbicides, fertilizers, etc.
実施例1 粉 剤
表中にある化合物 3部
クレー 40部
り″り 57部
実施例2 水和剤
表中にある化合物 75部
ホワイトカーぎン 16部
散布量については必ずしも制限はないが、通常は作物の
生育する圃場に散布する場合には有効成分化合物(A、
1.)として50〜1000,9/10a、また、土壌
中に施用する場合には2〜8 kgA、1./10a程
度が適当である。勿論、これは一つの目安であり、作物
の種類、病害の種類及び被害の程度、時期、天候、薬剤
の剤型等の要因を考慮して必要に応じて適宜加減される
。Example 1 Powder Compounds listed in the table 3 parts Clay 40 parts Literary powder 57 parts Example 2 Wettable powder Compounds listed in the table 75 parts White Cargin 16 parts There is no particular limit to the amount of spraying, but it is usually When spraying on fields where crops grow, active ingredient compounds (A,
1. ) as 50-1000, 9/10a, and 2-8 kgA, 1. /10a is appropriate. Of course, this is just a guideline, and it may be adjusted as necessary, taking into account factors such as the type of crop, the type and degree of damage, the season, the weather, and the dosage form of the drug.
以下、本発明化合物の効果を具体的に説明するため、代
表的な試験例を示す。但し、これらは単なる例示であり
本発明の適用例はこれらのみに限られないことは言うま
でもない。Hereinafter, typical test examples will be shown to specifically explain the effects of the compounds of the present invention. However, these are merely examples, and it goes without saying that the application examples of the present invention are not limited to these.
試験例−1植物病源菌に対する抗菌力試験く試験方法〉
所定の培地に培養した植物病源菌の分生胞子をPSA培
地に均一に混合し、所定の容器に一定量を流し込み均一
なプレートラつくる。固化した後に所定の濃度の薬剤の
一定量を吸収させ風乾させた直径81+++++の濾紙
をのせて48時間培養後に生じた阻止円の直径を測定す
る。Test Example-1 Test method for antibacterial activity against plant pathogenic bacteria> Conidia of plant pathogenic bacteria cultured in a specified medium are uniformly mixed in a PSA medium, and a certain amount is poured into a specified container to form a uniform plate. . After solidification, a filter paper with a diameter of 81+++++ which has absorbed a certain amount of a drug at a predetermined concentration and is air-dried is placed on it, and the diameter of the inhibition circle produced after 48 hours of culture is measured.
但し連数は2連とする。However, the number of stations shall be two.
試験例−2梨黒斑病菌に対する胞子発芽阻止試験く試験
方法〉
アンズ培地に7〜10日間培養したAl ternar
i akikuchianaの分生胞子と薬液全混合
し、顕微鏡100倍1視野当り約20個になるように調
整する。Test Example-2 Spore germination inhibition test against pear black spot fungus Test method> Al ternar cultured on apricot medium for 7 to 10 days
The conidia of I. akikuchiana and the drug solution are mixed together and adjusted so that the number of conidia is about 20 per field of view under a microscope at 100x magnification.
スライドグラス上に、この混合懸濁液を0.02m1滴
下し、温度27℃、湿度100%に20時間保った後に
検鏡して、胞子発芽の有無を調査する。A drop of 0.02 ml of this mixed suspension is placed on a slide glass, kept at a temperature of 27° C. and a humidity of 100% for 20 hours, and examined under a microscope to check for spore germination.
いずれも2反覆とし、約200個の胞子の発芽の有無程
度を調べる。Each test was repeated twice, and the presence or absence of germination of about 200 spores was examined.
く試験結果〉
試゛験例−3カンキツ黒点病菌に対する胞子発芽阻止試
験
く試験方法〉
カンキツ枯枝に培養したDiaporthe citr
iの分生胞子と薬液を混合し、顕微鏡100倍1視野当
り約20個になるように調整する。Diaporthe citr cultured on dead citrus branches
Mix the conidia of conidia i and the drug solution, and adjust to about 20 conidia per field of view under a microscope at 100x magnification.
スライドグラス上に、この混合懸濁液を0.02m1滴
下し、温度27℃、湿度lOOチに20時間保った後に
、検顕して胞子発芽の有無を調査する。A drop of 0.02 ml of this mixed suspension was placed on a slide glass, kept at a temperature of 27° C. and a humidity of 100° C. for 20 hours, and then subjected to microscopic examination to examine the presence or absence of spore germination.
いずれも2反覆とし、約200個の胞子の発芽の有無程
度を調べる。Each test was repeated twice, and the presence or absence of germination of about 200 spores was examined.
〈試験結果〉<Test results>
Claims (1)
(II)で示される、(1)のトートマーの誘導体を有
効成分として含有する農園芸用殺菌剤。 一般式 (但し、(1) 、 (II)共に R1がアルキル基
か芳香族基でありしかも、RがC6以上のアルキル基、
アラルキル基、芳香族基あるいは複素環基である化合物
および、R1が複素環基、置換フェノキシ基、置換チオ
フェノキシ基のいづれかであり、L ’Iy’ Mt
、R2が水素、アルキル基、芳香族基、複素環基のいず
れかである化合物を弄し、Rはアルキル基、アシル基、
カルバモイル基、置換スルホニル基を表す。)Claims: An agricultural and horticultural fungicide containing α-cyanoketones represented by the general formula (1) and a tautomer derivative (1) represented by the general formula (II) as active ingredients. General formula (provided that both (1) and (II) R1 is an alkyl group or an aromatic group, and R is a C6 or more alkyl group,
Compounds that are an aralkyl group, aromatic group, or heterocyclic group, and R1 is a heterocyclic group, substituted phenoxy group, or substituted thiophenoxy group, and L 'Iy' Mt
, R2 is hydrogen, an alkyl group, an aromatic group, a heterocyclic group, and R is an alkyl group, an acyl group,
Represents a carbamoyl group or substituted sulfonyl group. )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11688483A JPS6011401A (en) | 1983-06-30 | 1983-06-30 | Agricultural and horticultural fungicide containing alpha- cyanoketone derivative as active component |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11688483A JPS6011401A (en) | 1983-06-30 | 1983-06-30 | Agricultural and horticultural fungicide containing alpha- cyanoketone derivative as active component |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6011401A true JPS6011401A (en) | 1985-01-21 |
Family
ID=14698021
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11688483A Pending JPS6011401A (en) | 1983-06-30 | 1983-06-30 | Agricultural and horticultural fungicide containing alpha- cyanoketone derivative as active component |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6011401A (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5006563A (en) * | 1989-12-14 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones |
JPH03199441A (en) * | 1989-12-28 | 1991-08-30 | Mitsubishi Materials Corp | Electrically conductive yarn |
US5177111A (en) * | 1989-12-14 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones and pharmaceutical compositions thereof |
WO1998035935A1 (en) * | 1997-02-14 | 1998-08-20 | Ishihara Sangyo Kaisha Ltd. | Acrylonitrile compounds, process for their production and pesticides containing them |
US5891897A (en) * | 1995-04-27 | 1999-04-06 | Nissan Chemical Industries, Ltd. | Oxopropionitrile derivative and vermin controlling agent |
US6063734A (en) * | 1996-04-25 | 2000-05-16 | Nissan Chemical Industries, Ltd. | Etylene derivatives and pesticides containing said derivatives |
EP1338589A1 (en) * | 2000-11-02 | 2003-08-27 | Nippon Soda Co., Ltd. | Organic compound having cyano group and insecticides/miticides |
US6642234B1 (en) | 1998-12-25 | 2003-11-04 | Nissan Chemical Industries, Ltd. | Acrylonitrile compounds |
US6899886B2 (en) | 2000-08-11 | 2005-05-31 | Otsuka Chemical Co., Ltd. | Acylacetonitriles, process for preparation thereof and miticides containing the same |
JP2008001715A (en) * | 1996-04-25 | 2008-01-10 | Nissan Chem Ind Ltd | Ethylene derivative and pesticide |
-
1983
- 1983-06-30 JP JP11688483A patent/JPS6011401A/en active Pending
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5177111A (en) * | 1989-12-14 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones and pharmaceutical compositions thereof |
US5300527A (en) * | 1989-12-14 | 1994-04-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Alkylamino-and alkylamino alkyl diarylketones |
US5006563A (en) * | 1989-12-14 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones |
JPH03199441A (en) * | 1989-12-28 | 1991-08-30 | Mitsubishi Materials Corp | Electrically conductive yarn |
US5891897A (en) * | 1995-04-27 | 1999-04-06 | Nissan Chemical Industries, Ltd. | Oxopropionitrile derivative and vermin controlling agent |
US7037880B2 (en) | 1996-04-25 | 2006-05-02 | Nissan Chemical Industries, Ltd. | Ethylene derivatives and pesticides containing said derivatives |
US6063734A (en) * | 1996-04-25 | 2000-05-16 | Nissan Chemical Industries, Ltd. | Etylene derivatives and pesticides containing said derivatives |
US6462049B1 (en) | 1996-04-25 | 2002-10-08 | Nissan Chemical Industries, Ltd. | Ethylene derivatives and pesticides containing said derivatives |
USRE38188E1 (en) | 1996-04-25 | 2003-07-15 | Nissan Chemical Industries, Ltd. | Ethylene derivatives and pesticides containing said derivatives |
US7566683B2 (en) | 1996-04-25 | 2009-07-28 | Nissan Chemical Industries, Ltd. | Ethylene derivatives and pesticides containing said derivatives |
JP2008001715A (en) * | 1996-04-25 | 2008-01-10 | Nissan Chem Ind Ltd | Ethylene derivative and pesticide |
WO1998035935A1 (en) * | 1997-02-14 | 1998-08-20 | Ishihara Sangyo Kaisha Ltd. | Acrylonitrile compounds, process for their production and pesticides containing them |
US6642234B1 (en) | 1998-12-25 | 2003-11-04 | Nissan Chemical Industries, Ltd. | Acrylonitrile compounds |
US6899886B2 (en) | 2000-08-11 | 2005-05-31 | Otsuka Chemical Co., Ltd. | Acylacetonitriles, process for preparation thereof and miticides containing the same |
US6987112B2 (en) | 2000-11-02 | 2006-01-17 | Nippon Soda Co., Ltd. | Organic compound having cyano group and insecticides/miticides |
EP1338589A4 (en) * | 2000-11-02 | 2004-03-17 | Nippon Soda Co | Organic compound having cyano group and insecticides/miticides |
EP1338589A1 (en) * | 2000-11-02 | 2003-08-27 | Nippon Soda Co., Ltd. | Organic compound having cyano group and insecticides/miticides |
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