JPS6216453A - Acylaminovaleronitrile derivative, production thereof, herbicide and agricultural and horticultural fungicide containing same - Google Patents
Acylaminovaleronitrile derivative, production thereof, herbicide and agricultural and horticultural fungicide containing sameInfo
- Publication number
- JPS6216453A JPS6216453A JP15512385A JP15512385A JPS6216453A JP S6216453 A JPS6216453 A JP S6216453A JP 15512385 A JP15512385 A JP 15512385A JP 15512385 A JP15512385 A JP 15512385A JP S6216453 A JPS6216453 A JP S6216453A
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- Prior art keywords
- group
- formula
- substituted
- compound
- acylaminovaleronitrile
- 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.)
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- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は一般式（１）
（式中、Ａはフェニル基、置換フェニル基、ピリジル基
、置換ピリジル基、フリル基、置換フリル基、チェニル
基、置換チェニル基またはナフチル基を示す）で表され
るアシルアミノバレロニトリル誘導体、その製造法およ
びそれらを有効成分として含有する水田用除草剤または
農園芸用殺菌剤に関するものである。Detailed Description of the Invention [Industrial Application Field] The present invention relates to the general formula (1) (wherein A is a phenyl group, substituted phenyl group, pyridyl group, substituted pyridyl group, furyl group, substituted furyl group, chenyl group) The present invention relates to acylaminovaleronitrile derivatives represented by the following formulas (representing a substituted chenyl group, a substituted chenyl group, or a naphthyl group), a method for producing the same, and a herbicide for paddy fields or a fungicide for agricultural and horticultural purposes containing these as active ingredients.
従来より農園芸上有用なアミド誘導体は非常に多（の研
究がなされており、特徴ある生理活性を示す化合物が多
数見出され、実用に供されている。A large number of amide derivatives useful in agriculture and horticulture have been studied, and many compounds exhibiting characteristic physiological activities have been discovered and put into practical use.
例えば置換ベンズアミド誘導体として、除草剤としては
エチル−Ｎ−ベンゾイル−Ｎ−（３，４−ジクロロフェ
ニル〕−２−アミノプロピオネート〔ベンゾイルプロッ
プエチル〕、殺菌剤としては２−メチル−Ｎ−（３−イ
ソプロポキシフェニル）ベンズアミド（メブロニル〕な
どが知られている。For example, substituted benzamide derivatives include ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate [benzoylprop-ethyl] as a herbicide, and 2-methyl-N-(3-aminoprop-ethyl) as a fungicide. -isopropoxyphenyl)benzamide (mebronyl) and the like are known.
しかし、本発明で示されるようなアシルアミノバレロニ
トリル誘導体およびそれらの生理活性については知られ
ていない。However, acylaminovaleronitrile derivatives and their physiological activities as shown in the present invention are not known.
ケミカル・アブストラクツ（Ｃｈｅｍｉｃａｌ Ａｂｓ
ｔｒａｃｔｓ ）によれば本発明で示されるようなアシ
ルアミノブテニルニトリル誘導体と近緑のアシルアミノ
飽和脂肪族誘導体の合成の例がわずかにみられる。例え
ば、ジャーナル・オフーザ・ケミカルツサイエテイ（Ｊ
、Ｏｈｅｍ、Ｓｏｃ、 ）、 １９６５．２１４５〜２
１５０ページ、およびシンセシＸ （８ｙｎｔｈｅｓｉ
ｓ ） 、 １９７２ 。Chemical Abs
tracts), there are a few examples of the synthesis of acylaminobutenyl nitrile derivatives and near-green acylamino saturated aliphatic derivatives as shown in the present invention. For example, the Journal of the Chemical Society (J
, Ohem, Soc, ), 1965.2145-2
150 pages, and 8ynthesi
s), 1972.
１１号、６２２〜６２４ページには２−ベンゾイルアミ
ツブテロニトリル、あるいはビニレタン・デ・う・ソシ
エテー、１ミーク・ド・７ランセ（Ｂｕｌｌ、 Ｓｏｃ
、Ｏｈｉｍ、 Ｆｒ。No. 11, pp. 622-624, 2-benzoylamitubuteronitrile, or vinylethane des sociétés, 1 mique de 7 lances (Bull, Soc.
, Ohim, Fr.
）、１９６９．１１号、４１０８〜４１１１ページ、お
よびユスタス・リービッヒ・アンナーレン・チル・ヘミ
−（、ｒｕｓｔｕｓＬｉｅｂｉｇｓＡｎｎ、Ｏｈｅｍ、
）、 １９７２． ７６４゜６９〜９３ページには２
−ペアシイルアミノプロピオニトリルの合成例が例示さ
れている。しかしこれらの文献では記載された化合物の
生理活性については全く触れられていない。), No. 1969.11, pp. 4108-4111, and Justus Liebigs Ann, Ohem,
), 1972. 764° 2 on pages 69-93
- An example of the synthesis of pacylaminopropionitrile is illustrated. However, these documents do not mention at all the physiological activities of the compounds described.
従来、水田用除草剤としてはアミド系化合物、チオール
カーバメート系化合物、ジフェニルエーテル系化合物等
多くの除草剤が開発され実用に供されているが、まだま
だその性能は十分とはいえない。アミド系化合物ブタク
ロールは田植前後に使用されているが、温度条件等によ
り発生する稲に対する薬害が常に問題となっている。チ
オールカーバメート系化合物モリネートは魚毒性が問題
となり使用規制されている。またベンチオカーブは土壌
の還元条件下における水稲に対する薬害が問題となって
いる。Conventionally, many herbicides such as amide compounds, thiol carbamate compounds, and diphenyl ether compounds have been developed and put into practical use as herbicides for paddy fields, but their performance is still not sufficient. The amide compound butachlor is used before and after rice planting, but chemical damage to rice caused by temperature conditions has always been a problem. The use of the thiol carbamate compound molinate is regulated due to fish toxicity. Furthermore, Benthiocarb poses a problem of phytotoxicity to paddy rice under reducing soil conditions.
ジフェニルエーテル系化合物はブタクロール同様田植直
後に使用されているものの、処理時期が遅れると極端に
活性がおちる。Diphenyl ether compounds, like butachlor, are used immediately after rice planting, but their activity decreases dramatically if treatment is delayed.
これらの除草剤はいずれもある一面では優れた性能を有
する故に現実には広（普及し、使用されているものであ
るが、次第に欠点および問題点が顕在化してきており、
新たなより使い易い優れた性能を有する水田用除草剤が
強く望まれている。All of these herbicides have excellent performance in some respects, so in reality they are widely used and used, but their shortcomings and problems have gradually become apparent.
There is a strong need for a new herbicide for rice fields that is easier to use and has superior performance.
一方、農園芸用殺菌剤としては従来から様々の化学構造
を有する化合物が実用に供されているが各種作物の疫病
およびべと病に対してはカプタホＡ／、ＴＰＮ１キャブ
タン、あるいはジチオカーバメート系薬剤が広く一般に
使用され、作物増産に寄与してきた。しかしこれらの化
合物はいずれも疫病およびべと病に対して予防的な効果
が主であり、治療的な効果は全（期待できない。その為
、病害の発生が認められたときには既に十分な効果が期
待できないという大きな欠点を有している。On the other hand, compounds with various chemical structures have been put into practical use as agricultural and horticultural fungicides. has been widely used and has contributed to increased crop production. However, all of these compounds mainly have a preventive effect against late blight and downy mildew, and cannot be expected to have any therapeutic effect. Therefore, by the time disease outbreaks are observed, the sufficient effect has already been achieved. It has the major drawback of being unpredictable.
現実に作物病害防除の為の薬剤散布を考えると多かれ少
かれ病害発生後に散布することになり、これらの化合物
では完全な病害防除は困難である。In reality, when considering the spraying of chemicals to control crop diseases, they are more or less sprayed after the disease has appeared, and it is difficult to completely control the disease with these compounds.
また防除効果を示す化合物の濃度も極めて高く、防除薬
剤の安全使用からも問題視されている。こうした点を改
良すべく新たな防除剤の研究が鋭意続けられ、現在では
治療効果にも優れた効果を示すＮ−フェニルアラニンエ
ステル誘導体、例えばメタラキシル（Ｎ−（２，（Ｓ−
ジメチルフェニルノーＮ−（２’−メトキシアセチル〕
アラニンメチルエステル〕等が開発され、世界的に実用
に供されつつある。しかし、これらＮ−フェニルアラニ
ンエステル誘導体は既にその薬剤耐性菌が問題視されて
いる。Furthermore, the concentration of compounds that exhibit pesticidal effects is extremely high, which is also viewed as a problem in terms of the safe use of pesticides. In order to improve these points, research into new insecticides has continued, and currently N-phenylalanine ester derivatives, such as metalaxyl (N-(2, (S-
Dimethylphenyl no N-(2'-methoxyacetyl)
Alanine methyl ester], etc. have been developed and are being put into practical use worldwide. However, these N-phenylalanine ester derivatives have already become a problem due to their drug-resistant bacteria.
本発明は上に記載した従来技術の欠点を克服し、水田用
除草剤および農園芸用殺菌剤として極めて優れた特性を
有する化合物、その型造法およびそれらを有効成分とす
る有害雑草防除剤並びに有害微生物防除剤を提供するこ
とを課題とする。The present invention overcomes the drawbacks of the prior art described above and provides a compound having extremely excellent properties as a herbicide for paddy fields and a fungicide for agriculture and horticulture, a molding method thereof, and a noxious weed control agent containing the compound as an active ingredient. The objective is to provide a harmful microorganism control agent.
つまり、除草剤としては水田用として適期幅が広く、ま
た水稲に対する薬害も少く、魚毒性も低（、殺閑剤とし
ては各種作物の疫病、べと病等に対しては予防的、治療
的効果の両方を合わせもち、また各種作物の苗立枯病等
土壌病害に対しても優れた防除効果を有する適用範囲の
広い新規化合物、簡易で、かつ高収率なそれら新規化合
物の製造法、およびそれらを含有する有用な農薬組成物
を提供することを課題とする。In other words, as a herbicide, it has a wide range of suitable periods for use in paddy fields, and has little toxicity to paddy rice and low toxicity to fish. A new compound with a wide range of applications that has both effects and also has an excellent control effect on soil diseases such as seedling damping-off of various crops, a simple and high-yielding method for producing these new compounds, It is an object of the present invention to provide a useful agrochemical composition containing the same.
〔課題を解決するための手段および作用〕前記課題を解
決するためアシル了ミノアルキルニトリル誘導体につい
て鋭意研究した結果、アシルアミノバレロニトリル誘導
体が、前記売先技術からは全く予測することのできない
生理活性を有するものであり、水田用除草剤としては適
期幅が広（、また水稲に対する薬害も少な（、魚毒性も
低く、一方、殺菌剤としては各種作物の疫病、べと病等
に対しては予防的、治療的効果の両方を合せもち、また
各種作物の苗立枯病等土壌病害に対しても優れた防除効
果を示すことを見出し本発明を完成した。[Means and effects for solving the problem] In order to solve the above problem, as a result of intensive research on acylaminovaleronitrile derivatives, it was found that acylaminovaleronitrile derivatives have physiological activities that could not be predicted from the customer's technology. As a herbicide for paddy fields, it has a wide range of suitable periods (and is less harmful to paddy rice (and has low toxicity to fish).On the other hand, as a fungicide, it is effective against late blight, downy mildew, etc. of various crops. We have completed the present invention by discovering that it has both preventive and therapeutic effects, and also exhibits an excellent control effect against soil diseases such as seedling damping-off of various crops.
本発明に係るアシルアミノバレロニトリル誘導体は一般
式（１）
（式中、人はフェニル基、置換フェニル基、ピリジル基
、置換ピリジル基、フリル基、置換フリル基、チェニル
基、置換チェニル基またはナフチル基を示す）で表され
る新規な化合物である。The acylaminovaleronitrile derivative according to the present invention has the general formula (1) (wherein, phenyl group, substituted phenyl group, pyridyl group, substituted pyridyl group, furyl group, substituted furyl group, chenyl group, substituted chenyl group or naphthyl group) This is a novel compound represented by (indicating a group).
本発明はさらに前記一般式（１）で表されるアシルアミ
ノバレロニトリル誘導体の新規な型造法についても鋭意
検討した結果、高収率で目的物を得る方法を見出し本発
明を完成した。In the present invention, as a result of intensive study on a new method for molding the acylaminovaleronitrile derivative represented by the general formula (1), the present invention was completed by discovering a method for obtaining the desired product in high yield.
すなわち、本発明に係るアシルアミノ誘導体であるアシ
ルアミノバレロニトリル誘導体の型造法は一般式（ｎ）
Ａ −ａｏａｇ （Ｉ［）
（式中、Ａは前記の意味を示す。）で表される酸クロリ
ドと式（１）
で表されるα−アミノバレロニトリルとを反応させるこ
とを特徴とする一般式（１）で表されるアシルアミノバ
レロニトリル誘導体の型造法である。That is, the molding method for the acylaminovaleronitrile derivative, which is an acylamino derivative according to the present invention, is an acid represented by the general formula (n) A -aoag (I[) (wherein A has the above meaning). This is a method for producing an acylaminovaleronitrile derivative represented by the general formula (1), which is characterized by reacting chloride with α-aminovaleronitrile represented by the formula (1).
一般式（１）で表される本発明化合物の製造方法を反応
図式により以下に説明する。The method for producing the compound of the present invention represented by general formula (1) will be explained below using a reaction scheme.
反応図式
（式中、Ａは前記の意味を示す。）
ｎ−ブチルアルデヒドをＨＯＮと反応し、α−ヒ）”ｏ
キシバレロニトリルとし、サラにアンモニアで処理する
ことによりα−アミノバレロニトリルを得る。ついで、
これを酸受容体の存在下で酸クロリド（Ｉｆ）と反応さ
せる。酸受容体の例には、例えばトリエチルアミン、ジ
メチルアニリン、ピリジ／等の有機塩基、アンモニア、
炭酸カリウム、炭酸ナトリウム、炭酸水素ナトリウム、
水酸化すトリウム、炭酸アンモニウムなどの無機塩基が
あるが、これらに限定されるものではない。この反応は
溶剤または希釈剤中で行うのが好ましい。ピリジノは溶
剤と酸受容体の両方として用い得る。Reaction scheme (in the formula, A indicates the above meaning) n-butyraldehyde is reacted with HON, α-H)”o
α-aminovaleronitrile is obtained by converting it into xyvaleronitrile and then treating the mixture with ammonia. Then,
This is reacted with acid chloride (If) in the presence of an acid acceptor. Examples of acid acceptors include organic bases such as triethylamine, dimethylaniline, pyridine, ammonia,
potassium carbonate, sodium carbonate, sodium bicarbonate,
Inorganic bases include, but are not limited to, thorium hydroxide and ammonium carbonate. This reaction is preferably carried out in a solvent or diluent. Pyridino can be used both as a solvent and as an acid acceptor.
この反応は中間体のα−アミノバレロニトリルの熱安定
性がよくないため、あまり高温下での反応は望ましくな
く、また、発熱反応であるため冷却下に行うことが望ま
しい。かくして得た所望のアシルアミノバレロニトリル
誘導体は再結晶、カラムクロマトグラフィ等常法によっ
て容易に単離およびｔＩ羨することが可能である。Since the intermediate α-aminovaleronitrile in this reaction has poor thermal stability, it is not desirable to react at too high a temperature, and since it is an exothermic reaction, it is desirable to carry out the reaction under cooling. The desired acylaminovaleronitrile derivative thus obtained can be easily isolated and subjected to tI analysis by conventional methods such as recrystallization and column chromatography.
さらに、本発明は本発明に係る前記一般式（Ｉ）で表さ
れるアシルアミノバレロニトリル誘導体を有効成分とし
て含有することを特徴とする水田用除草剤および農園芸
用殺菌剤を提供するものである。Furthermore, the present invention provides a herbicide for rice fields and a fungicide for agriculture and horticulture, which contain the acylaminovaleronitrile derivative represented by the general formula (I) according to the present invention as an active ingredient. be.
本発明化合物を水田用除草剤として使用する場合は、雑
草の生育段階や雑草の種類、調剤の剤型、施用方法およ
び各種環境条件等によってその施用量は変化するが、通
常アール当り０．１〜１００ｇが適当であり、望ましく
はアール当り０．５〜２５Ｉである。その殺草活性はイ
ネ科雑草に対して特徴的に強く、また他の雑草に対して
も強いものであり、たとえ枯殺させない場合でも強い抑
制効果を示す。このような特性は、逆にイネ科雑草に弱
ヤツリグサ科の雑草、たとえばタマガヤツリ、ホタルイ
等に対し、また、他の雑草の種類によって強弱はあるが
同様の傾向が認められる。When the compound of the present invention is used as a herbicide for paddy fields, the application amount varies depending on the growth stage of the weed, the type of weed, the dosage form of the preparation, the application method, various environmental conditions, etc., but is usually 0.1 per area. ˜100 g is suitable, preferably 0.5 to 25 I per are. Its herbicidal activity is characteristically strong against gramineous weeds, and is also strong against other weeds, and shows a strong suppressive effect even when not killed. On the contrary, such characteristics are weak against weeds of the Poaceae family, but similar tendencies are observed for weeds of the family Cyperaceae, such as Cyperus japonica and bulrushes, and other weeds, although their strength varies depending on the type of weed.
また本発明化合物の施用時期は、雑草の発生前から生育
期まで幅が広い。公知のアミド系化合物ブタクロールや
チオールカーバメート系化合物ベンチオカーブと比較し
て、本発明化合物は、はるかに使用適期幅が広く、従来
にない優れた特徴を有するものであり、処理時期の制約
の少い、使い易い除草剤になりうる。タイヌビエに対す
る除草活性は処理時期によってその実用薬量は当然具る
ものの、３．５葉期のタイヌビエに対してベンチオカー
ブやブタクロールが実用薬量で効果不十分であるのに対
して、本発明化合物はそれらの実用薬量以下の薬量で実
用に十分耐えうる活性を示す。Moreover, the timing of application of the compound of the present invention is wide ranging from before the emergence of weeds to the growing season. Compared to the known amide compound butachlor and the thiol carbamate compound bentiocarb, the compound of the present invention has a much wider range of suitable use periods and has excellent characteristics not found in the past. It can be an easy-to-use herbicide. Although the practical amount of herbicidal activity against Japanese millet naturally varies depending on the treatment period, bentiocarb and butachlor are insufficiently effective at practical doses against Japanese millet at the 3.5-leaf stage, whereas the compounds of the present invention They exhibit sufficient activity for practical use at doses lower than their practical doses.
本発明化合物はいずれの処理時期に使用しても、移植水
稲に対しては極めて薬害の小さい化合物である。The compound of the present invention has extremely low phytotoxicity to transplanted paddy rice no matter when it is used at any time of treatment.
本発明化合物を農園芸用殺菌剤として使用する場合は、
藻菌類によってひきおこされる各種作物の疫病およびべ
と病忙有効であるばかりでなく、他の種々の植物病原菌
類によってひきおこされる病害に対しても有効である。When using the compound of the present invention as an agricultural and horticultural fungicide,
It is effective not only against late blight and downy mildew of various crops caused by algal fungi, but also against diseases caused by various other plant pathogenic fungi.
しかも、予防的、治療的効果を合せもつ。Moreover, it has both preventive and therapeutic effects.
主な防除対象病害としてはジャガイモ疫病、トマト疫病
、タバコ疫病、イチゴ疫病、アズキ茎疫病、プドウベと
病、キエウリベと病、ホップベと病、シーンギクベと病
、あるいはアクアノミセス属菌、ピシウム属菌等による
各種作物苗立枯病等が挙げられる。The main diseases to be controlled include potato late blight, tomato late blight, tobacco late blight, strawberry late blight, adzuki bean stem blight, pudobe blight, kiewribe blight, hopbe blight, sheen gikube blight, Aquanomyces sp., Pythium blight, etc. Examples include damping-off of various crop seedlings caused by this disease.
本発明化合物の施用方法としては種子消毒、茎葉散布、
土壌処理等が挙げられるが、通常当業者が利用するどの
ような施用方法にても十分な効力を発揮する。施用量お
よび施用濃度は対象作物、対象病害、病害の発生程度、
化合物の剤型、施用方法および各種環境条件等によって
変動するが、散布する場合にはアール当り５〜２００ｇ
が適当であり、望しくはアール当り１０〜１００ｇであ
る。散布濃度としては２０〜１．０００ｐｐｍが適当テ
あり、望ましくは５０〜５００ ｐｐｍである。Methods for applying the compound of the present invention include seed disinfection, foliage spraying,
Examples include soil treatment, but any application method commonly used by those skilled in the art will exhibit sufficient efficacy. The application amount and concentration will depend on the target crop, target disease, degree of disease occurrence,
It varies depending on the dosage form of the compound, application method, various environmental conditions, etc., but when spraying, the amount is 5 to 200 g per area.
is appropriate, preferably 10 to 100 g per are. A suitable spraying concentration is 20 to 1,000 ppm, preferably 50 to 500 ppm.
本発明の除草剤および農園芸用殺菌剤は他の殺菌剤や殺
虫剤、除草剤、植物成長調節剤等の農薬、土壌改良剤ま
丸は肥効性物質との混合使用は勿論のこと、これらとの
混合調剤も可能である。The herbicides and agricultural and horticultural fungicides of the present invention can of course be used in combination with other fungicides, insecticides, herbicides, agricultural chemicals such as plant growth regulators, soil conditioners, and fertilizing substances. Mixed formulations with these are also possible.
本発明の化合物は、そのまま施用してもよいが固体また
は液体の希釈剤を包含する担体と混合した組成物の形で
施用するのが好ましい。ここでぃう担体とは、処理すべ
き部位へ有効成分の到達を助け、また有効成分化合物の
貯蔵、輸送、取扱いを容易にするために配合される合成
または天然の無機または有機物質を意味する。The compounds of the invention may be applied neat or preferably in the form of a composition mixed with a carrier, including solid or liquid diluents. Carrier here means an inorganic or organic substance, synthetic or natural, which is incorporated to aid in the delivery of the active ingredient to the area to be treated and to facilitate storage, transport and handling of the active ingredient compound. .
適当な固体担体としてはモンモリロナイト、カオリナイ
トなどの゛粘土類、ケイソウ士、白土、タルク、バーミ
キュライト、石膏、炭酸カルシウム、シリカゲル、硫安
などの無機物質、大豆粉、鋸屑、小麦粉などの植物性有
機物質および尿素などがあげられる。Suitable solid carriers include clays such as montmorillonite and kaolinite, inorganic substances such as diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, and ammonium sulfate, and vegetable organic substances such as soybean flour, sawdust, and wheat flour. and urea.
適当な液体担体としてはトルエン、キシレン、クメンな
どの芳香族炭化水素、ケロシｙ、鉱油などのパラフィン
系炭化水素、四塩化炭素、りＣ！ロホルム、ジクロロエ
タンなどのノ・ロゲン化炭化水素、アセトン、メチルエ
チルケトンなどのケトン類、ジオキサン、テトラヒドロ
フランなどのエーテル類、メタノール、プロパツール、
エチレングリコールなどのアルコール類、ジメチルホル
ムアミド、ジメチルスルホキシド、水などがあげられる
。Suitable liquid carriers include aromatic hydrocarbons such as toluene, xylene, and cumene, paraffinic hydrocarbons such as kerosene, mineral oil, carbon tetrachloride, and C! Logenated hydrocarbons such as roform and dichloroethane, ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, methanol, propatool,
Examples include alcohols such as ethylene glycol, dimethylformamide, dimethyl sulfoxide, and water.
さらに本発明化合物の効力を増強するために、製剤の剤
型、適用場面等を考慮して目的に応じてそれぞれ単独に
、または組合わせて以下のような補助剤を使用すること
もできる。Furthermore, in order to enhance the efficacy of the compound of the present invention, the following adjuvants may be used individually or in combination depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.
乳化、分散、拡展、湿潤、結合、安定化等の目的ではり
ゲニンスルホン酸塩などの水溶性塩基、アルキルベンゼ
ンスルホン酸塩、アルキル硫酸エステル等の非イオン性
界面活性剤、ステアリン酸カルシウム、ワックス等の滑
剤、イソプロピルヒドロジエンホスフェート等の安定剤
、その他メチルセルロース、カルボキシメチルセルロー
ス、カゼイン、アラビアゴム等があげられる。しかし、
これらの成分は以上のものに限定されるものではない。For the purpose of emulsification, dispersion, spreading, wetting, binding, stabilization, etc., water-soluble bases such as genin sulfonate, nonionic surfactants such as alkylbenzene sulfonate, alkyl sulfate, calcium stearate, wax, etc. lubricants, stabilizers such as isopropylhydrodiene phosphate, and others such as methylcellulose, carboxymethylcellulose, casein, and gum arabic. but,
These components are not limited to those mentioned above.
本発明化合物の組成物の有効成分量は、通常粉剤では０
．５〜２０重量％、乳剤では５〜３０重量％、水利剤で
は１０〜９０重量％、粒剤では０１〜２０重量％、フロ
ワブル剤では１０〜９０重量％である。The amount of active ingredient in the composition of the compound of the present invention is usually 0 when used as a powder.
．． The content is 5 to 20% by weight, 5 to 30% by weight for emulsions, 10 to 90% by weight for aquariums, 01 to 20% by weight for granules, and 10 to 90% by weight for flowable preparations.
本発明に係る一般式（１）で表わされるアシルアミノバ
レロニトリル誘導体の代表例を表−１に示す。Representative examples of the acylaminovaleronitrile derivatives represented by the general formula (1) according to the present invention are shown in Table-1.
次に本発明化合物の製造方法を合成例をあげて具体的に
説明する。Next, the method for producing the compound of the present invention will be specifically explained by giving a synthesis example.
合成例１
２−（３−ジクロロベンゾイルアミン〕バレロニトリル
（化合物番号−２）の合成
１−１．α−アミノバレロニトリルの合成ｎ−ブチルア
ルデヒド２５０ｇに酢酸ナトリウム０．１８１を加え、
水浴にて０〜５℃に冷却した。Synthesis Example 1 Synthesis of 2-(3-dichlorobenzoylamine]valeronitrile (compound number-2) 1-1. Synthesis of α-aminovaleronitrile 0.181 of sodium acetate was added to 250 g of n-butyraldehyde.
Cooled to 0-5°C in a water bath.
攪拌下にＨＯＮ１５３１ｎＩ！を約１時間を要して滴下
し、更に１２時間、同温度で攪拌を続げた。窒素ガスを
一昼夜導入し、過剰のＨＯＮを追い出した後、メタノー
ル８００ｍ／を加え、ドライアイス−メタノール浴にて
内温を一１０℃に冷却し、液体アンモニア４００ｄを加
えた。０〜５℃にて４時間攪拌した。減圧下に過剰のア
ンモニアおよびメタノールを除去し、粗α−アミノバレ
ロニトリル２８６ｇを得た。これはさらに精製操作を行
うことなく、次の反応に用いた。HON1531nI under stirring! was added dropwise over about 1 hour, and stirring was continued at the same temperature for an additional 12 hours. After introducing nitrogen gas all day and night to drive out excess HON, 800 m/m of methanol was added, the internal temperature was cooled to -10°C in a dry ice-methanol bath, and 400 m/m of liquid ammonia was added. The mixture was stirred at 0-5°C for 4 hours. Excess ammonia and methanol were removed under reduced pressure to obtain 286 g of crude α-aminovaleronitrile. This was used in the next reaction without further purification.
１−２．２−（５−クロロベンゾイルアミツノバレロニ
トリル（化合物番号−２）の合成
１−１で得たα−アミノバレロニトリル５．０９をエチ
ルエーテル５０ｍ／に溶解し、０〜５℃に冷却した。ト
リエチルアミン６．１１を加えた後、攪拌下にｍ−クロ
ロベンゾイルクロリド８．８１を滴下した。滴下終了後
、さらに同温度で１時間攪拌した。水５０１ｎｌを加え
析出したトリエチルアミン塩酸塩を溶解した。エーテル
層を分液し、水洗、乾燥の後溶媒を減圧下に留去した。1-2. Synthesis of 2-(5-chlorobenzoylamitunovaleronitrile (Compound No.-2) After adding 6.11 ml of triethylamine, 8.81 ml of m-chlorobenzoyl chloride was added dropwise while stirring. After the addition was completed, the mixture was further stirred at the same temperature for 1 hour. 501 nl of water was added and triethylamine hydrochloride precipitated. The ether layer was separated, washed with water, dried, and the solvent was distilled off under reduced pressure.
残渣をシリカゲルカラムクロマトグラフィーにより精製
した。The residue was purified by silica gel column chromatography.
ヘキサン−酢酸エチル系より溶出し、所望の２−（３−
クロロベンゾイルアミツノバレロニトリルを固体として
６．７ｇ得た。収率５６．６％。Elute from hexane-ethyl acetate system to obtain the desired 2-(3-
6.7 g of chlorobenzoylamitunovaleronitrile was obtained as a solid. Yield 56.6%.
合成例２
２−（３−メトキシベンゾイルアミノコバレロニトリル
（化合物番号−２０〕の合成
１−１で得たα−アミノバレロニトリジル、ｏｙをテト
ラヒドロ７ラン１ＤＱｍｌに溶解し、０〜５℃に冷却し
た。炭酸カリウム１０．０ｇを加え、攪拌下にｍ−メト
キシベンゾイルクロリド８．５１を滴下した。滴下終了
後、さらに３時間攪拌した。Synthesis Example 2 α-Aminovaleronitridyl, oy obtained in Synthesis 1-1 of 2-(3-methoxybenzoylaminocovaleronitrile (Compound No.-20)) was dissolved in 1DQml of tetrahydro7ran and heated to 0 to 5°C. After cooling, 10.0 g of potassium carbonate was added, and 8.51 g of m-methoxybenzoyl chloride was added dropwise while stirring. After the dropwise addition was completed, the mixture was further stirred for 3 hours.
析出した結晶をＰ別し、ｒ液を減圧下蒸留して溶媒を留
去した。残渣をシクロヘキサンにより再結晶し、所望の
２−（３−メトキシベンゾイルアミノコバレロニトリル
を白色固体として７．２９得た。The precipitated crystals were separated from P, and the r liquid was distilled under reduced pressure to remove the solvent. The residue was recrystallized from cyclohexane to obtain 7.29 g of the desired 2-(3-methoxybenzoylaminocovaleronitrile as a white solid).
収率６２．０チ。Yield: 62.0 cm.
次に本発明の水田用除草剤または農園芸用殺菌剤の製造
法を製剤例により説明する。Next, the method for producing the herbicide for paddy fields or the fungicide for agriculture and horticulture of the present invention will be explained using formulation examples.
有効成分化合物は前記表−１の化合物番号で示す。「部
」は「重着部」をあられ丁。The active ingredient compounds are shown by compound numbers in Table 1 above. ``Part'' means ``heavy-duty part''.
製剤例１ 粉 剤
化合物（１）：３部、ケイソウ土＝２０部、白土：３０
部およびタルク：４７部を均一に粉砕混合して、粉剤１
００部を得た。Formulation Example 1 Powder Compound (1): 3 parts, diatomaceous earth = 20 parts, white clay: 30
1 part and 47 parts of talc were uniformly ground and mixed to make powder 1.
I got 00 copies.
製剤例２ 水和剤
化合物（２） ： ５０部、ケイソウ土：４４部、白土
：２０部、リグニンスルホン酸ナトリウム：１部および
アルキルベンゼンスルホン酸ナトリウム＝２部を均一に
粉砕混合して水利剤１００部を得た。Formulation Example 2 Wettable powder compound (2): 50 parts, diatomaceous earth: 44 parts, clay: 20 parts, sodium ligninsulfonate: 1 part, and sodium alkylbenzenesulfonate = 2 parts were uniformly ground and mixed to make an irrigation agent of 100 parts. I got the department.
製剤例３ 乳 剤
化合物（３） ： ２０部、シクロヘキサノン：１０部
、キシレン：５０部およびツルポール（東邦化学製界面
活性剤）２０部を均一に溶解混合し、乳剤１００部を得
た。Formulation Example 3 Emulsion Compound (3): 20 parts, cyclohexanone: 10 parts, xylene: 50 parts and 20 parts of Tulpol (surfactant manufactured by Toho Chemical Co., Ltd.) were uniformly dissolved and mixed to obtain 100 parts of an emulsion.
製剤例４ 粒 剤
化合物（４）：１部、ベントナイトエフ８部、タルク：
２０部、およびリグニンスルホン酸ナトリウム：１部を
混合し、適量の水を加えて混練した後、押し出し造粒機
を用いて通常の方法により造粒し乾燥後、粒剤１００部
を得た。Formulation Example 4 Granules Compound (4): 1 part, bentonite F 8 parts, talc:
After mixing 20 parts and 1 part of sodium ligninsulfonate, adding an appropriate amount of water and kneading, the mixture was granulated by a conventional method using an extrusion granulator, and after drying, 100 parts of granules were obtained.
製剤例５ 粒 剤
化合物（１０）ニア部、ポリエチレングリコールノニル
フェニルエーテル＝１部、ポリビニルアルコール＝５部
およびクレー＝８９部を均一混合し、加水造粒後、乾燥
し粒剤１００部を得た。Formulation Example 5 Granules Compound (10) Nia part, polyethylene glycol nonylphenyl ether = 1 part, polyvinyl alcohol = 5 parts and clay = 89 parts were uniformly mixed, and after hydrogranulation, it was dried to obtain 100 parts of granules. .
製剤例６ 粉 剤
化合物（６）：２部、炭酸カルシウム＝４０部およびク
レー：５８部を均一に混合し、粉剤１００部を得た。Formulation Example 6 Powder 2 parts of compound (6), 40 parts of calcium carbonate, and 58 parts of clay were uniformly mixed to obtain 100 parts of a powder.
製剤例７ 水和剤
化合物（５） ： ５０部、メルク：４０部、ラウリル
リン酸ナトリウム：５部、アルキルナフタレンスルホン
酸ナトリウム＝５部を混合し、水和剤１００部を得た。Formulation Example 7 Wettable powder Compound (5): 50 parts, Merck: 40 parts, sodium lauryl phosphate: 5 parts, and sodium alkylnaphthalene sulfonate = 5 parts were mixed to obtain 100 parts of a wettable powder.
製剤例８ 水和剤
化合物（６） ： ５０部、リグニンスルホン酸ナトリ
ウム＝１０部、アルキルナフタレンスルホン酸ナトリウ
ム：５部、ホワイトカーボン：１０部、ケイソウ土＝２
５部を混合粉砕し、水利剤１００部を得た。Formulation Example 8 Wettable powder compound (6): 50 parts, sodium ligninsulfonate = 10 parts, sodium alkylnaphthalenesulfonate: 5 parts, white carbon: 10 parts, diatomaceous earth = 2
5 parts were mixed and ground to obtain 100 parts of an irrigation agent.
製剤例９ フロワブル剤
化合物（７） ： ４０ 部、カルボキシメチルセルロ
ース＝５部、リグニンスルホン酸ナトリウム＝２部、ジ
オクチルスルホサクシネートナトリウム塩＝１部および
水５４部をサンドグラインダーで湿式粉砕し、フロワブ
ル剤１００部を得た。Formulation Example 9 Flowable agent Compound (7): 40 parts, carboxymethyl cellulose = 5 parts, sodium ligninsulfonate = 2 parts, dioctyl sulfosuccinate sodium salt = 1 part and 54 parts of water were wet-pulverized with a sand grinder to form a flowable agent. Got 100 copies.
次に本発明化合物の除草剤および農園芸用殺菌剤として
の効力を試験例によって説明する。なお、試験例におい
て以下の化合物を対照として用いた。Next, the efficacy of the compound of the present invention as a herbicide and a fungicide for agricultural and horticultural purposes will be explained using test examples. In addition, the following compounds were used as controls in the test examples.
対照化合物
Ａ：ベンゾイルアミノプロピオニトリルＢ：２−ベンゾ
イルアミノブチロニトリルＯ：２−クロロ−４６′−ジ
エチル−Ｎ−（ブトキシメチル〕アセトアニリド〔ブタ
クロール〕Ｄニジエチルチオカルバミド酸５−ｐ−クロ
ロベンジル〔ベンチオカーブ〕
Ｅ：ジンクエチレンビス（ジチオカーバメートノ〔ジネ
ブ〕
Ｐ：テトラクロロイソフタロニトリル（ＴＰＮ］対照化
対照化合物上びＢは前出文献にて公知の化合物であり、
０は発生前処理用の、Ｄは生育期処理用の水田用除草剤
として市販の薬剤。ＥおよびＦはジャガイモ疫病、キー
ウリベと病等の防除剤として市販の薬剤である。Control compound A: benzoylaminopropionitrile B: 2-benzoylaminobutyronitrile O: 2-chloro-46'-diethyl-N-(butoxymethyl)acetanilide [butachlor] Dnidiethylthiocarbamic acid 5-p-chloro Benzyl [benthiocarb] E: zinc ethylene bis(dithiocarbamateno[zineb]) P: tetrachloroisophthalonitrile (TPN) Control compound and B are compounds known in the above-mentioned literature,
0 is a commercially available herbicide for paddy fields for pre-emergence treatment and D is for growing season treatment. E and F are commercially available agents for controlling potato late blight, chyme blight, and the like.
試験例１ 水田発生前除草試験
ア−＃／ ５０００ワグネルポツトに土壌を詰め、タイ
ヌビエ、広葉雑草（キカシグサ、アゼナ、コナギ等〕、
ホタルイ、ヘラオモダカ、タマガヤツリの種子を播種し
、湛水状態とした。これにあらかじめ育苗しておいた水
稲苗（２〜３葉期）２本、を１株とし、その２株を移植
して温室内で生育させた。水稲移植１日後の雑草発生前
に供試化合物の所定量を前記製剤例５に記載した方法に
準じて調型した粒剤を用いて湛水下に処理した。処理３
０日後に雑草の発生状況および水稲に対する薬害を調査
した。結果を表−２に示した。Test Example 1 Paddy field pre-emergence weeding test A-#/5000 Wagner pots were filled with soil, and weeds such as Japanese millet, broad-leaved weeds (Kikashigusa, Azena, Japanese azalea, etc.),
Seeds of firefly, Heraomodaka and Tamagayatsuri were sown, and the area was flooded. Two paddy rice seedlings (2-3 leaf stage) that had been raised in advance were used as one plant, and the two plants were transplanted and grown in a greenhouse. One day after transplanting paddy rice and before the emergence of weeds, a predetermined amount of the test compound was submerged in water using granules prepared according to the method described in Formulation Example 5 above. Processing 3
After 0 days, weed growth status and chemical damage to paddy rice were investigated. The results are shown in Table-2.
表中、作物に対する薬害程度および雑草に対する除草効
果は、作物または雑草の発生ないし生育の状態を無処理
の場合の風乾型と比較し、下記の評価基準に従って表し
た。供試化合物は前記表−１の化合物番号によって示し
た（以下同様）。In the table, the degree of chemical damage to crops and the herbicidal effect on weeds are expressed by comparing the emergence or growth of crops or weeds with that of the untreated air-dried type according to the evaluation criteria below. The test compounds were indicated by compound numbers in Table 1 above (the same applies hereinafter).
評価基準
０：対無処理区風乾重比で示した生存率 ９１〜１００
％１ ： ７１〜
９０％２： ４１
〜７０％３： １
１〜４０チ４：
６〜１０チ５：
０〜５チ試験例２ 水田生育期除草試験
アール７’５０００ワグネルポツトに土壌を詰め、タイ
ヌビエ、広葉雑草（キカシグサ、アゼナ、コナギ等）、
ホタルイ、ヘラオモダカ、タマガヤツリの種子を播種し
、海氷状態とした。これにあらかじめ育苗しておいた水
稲苗（２〜３葉期）２木を１株とし、その２株を移植し
て温室内で生育させた。水稲移植１２日後の雑草生育期
に供試化合物の所定量を前記層剤例４に記載した方法に
準じて調製した粒剤を用いて湛水下に処理した。処理３
０日後に雑草の発生状況および水稲に対する薬害を調査
した。結果を表−３に示した。Evaluation standard 0: Survival rate shown by air dry weight ratio vs. untreated area 91-100
%1: 71~
90%2: 41
~70%3:1
1-40chi 4:
6-10chi 5:
0 to 5ch test example 2 Rice paddy growing season weeding test Fill a 7'5000 Wagner pot with soil, remove grass weeds, broad-leaved weeds (Kikashigusa, Azena, Prunus japonicus, etc.).
Seeds of firefly, yellowtail, and cypress were sown, and sea ice conditions were established. Two paddy rice seedlings (2-3 leaf stage) that had been raised in advance were used as one plant, and the two plants were transplanted and grown in a greenhouse. During the weed growth period 12 days after transplanting paddy rice, a predetermined amount of the test compound was submerged in water using granules prepared according to the method described in Layer Form Example 4 above. Processing 3
After 0 days, weed growth status and chemical damage to paddy rice were investigated. The results are shown in Table-3.
表中、作物に対する薬害程度および雑草の生育状態は試
験例１で示した方法に従って表した。In the table, the degree of chemical damage to crops and the growth state of weeds are expressed according to the method shown in Test Example 1.
表２および表３に示した結果より、本発明化合物群は水
田で問題となっている各種の有害雑草に対して発生前処
理で幅広い除草活性を示し、またこれまで除草効果が発
揮され難かった生育期処理でも除草活性を示し、かつ水
稲に対する薬害のほとんどない優れた化合物であること
が明らかである。From the results shown in Tables 2 and 3, the compound group of the present invention shows a wide range of herbicidal activity against various harmful weeds that are a problem in rice fields in pre-emergence treatment, and it has been difficult to demonstrate herbicidal effects until now. It is clear that it is an excellent compound that exhibits herbicidal activity even when treated during the growing season and causes almost no phytotoxicity to paddy rice.
また、化学構造が比較的近似である前出文献に記載の２
−ベンゾイルアミノプロピオニトリル、アルいは２−ベ
ンゾイルアミノブチロニトリル等では除草効果はほとん
ど認められず、本発明化合物はこれまでの公知事実から
は予想できない優れた特性を有することは明らかである
。In addition, the two compounds described in the above-mentioned document whose chemical structures are relatively similar
- Benzoylaminopropionitrile, Al or 2-benzoylaminobutyronitrile, etc. have almost no herbicidal effect, and it is clear that the compounds of the present invention have excellent properties that could not be expected from known facts. .
試験例３ ジャガイモ疫病防除試験
温室内でポットに育生したジャガイモ（品種：男爵、草
丈２５ｃｍ程度）に所定濃度の薬剤（供試化合物を前記
製剤例８の方法にて水利剤となし、これを水で所定濃度
に希釈したもの〕をスプレーガン（１，Ｏｋｐ／Ｃｍ”
）を使用して３鉢当りｓｏｍｚ散布し風乾した。あらか
じめジャガイモ切片上にて７日間培養したジャガイモ疫
病菌より遊走子浮遊液を調製した。この浮遊液を薬剤散
布したジャガイモ植物体上に噴霧接種し、被検植物を１
７〜１９℃、湿度９５チ以上で６日間保った後、病斑の
形成程度を調査した。Test Example 3 Potato Phytophthora control test Potatoes (variety: Baron, plant height approximately 25 cm) grown in pots in a greenhouse were treated with a prescribed concentration of drug (the test compound was used as an irrigation agent using the method of Formulation Example 8 above, and this was applied to water). diluted to the specified concentration] with a spray gun (1, Okp/Cm”
), somz was sprayed on three pots and air-dried. A zoospore suspension was prepared from potato Phytophthora blight that had been previously cultured on potato sections for 7 days. This suspension was sprayed and inoculated onto the potato plants sprayed with the drug, and the test plants were inoculated once.
After being kept at 7-19°C and humidity of 95 degrees or higher for 6 days, the degree of lesion formation was investigated.
各葉ごとに病斑面積割合を観察評価し発病度指数を求め
、それぞれの区について次式により罹病度を求めた。The disease severity index was determined by observing and evaluating the lesion area ratio for each leaf, and the disease severity was determined for each plot using the following formula.
なお、評価基準は次のとうりである。The evaluation criteria are as follows.
発病程度指数 ０： 病斑面積割合 ０％１：
１〜５％
２： ６〜２５％
３： ２６〜５０チ
４： ５１チ以上
ｎｏ：発病程度指数０の葉数
ｎＸ： １ 。Disease severity index 0: Lesion area ratio 0%1:
1-5% 2: 6-25% 3: 26-50chi 4: 51chi or more No: Number of leaves with disease severity index 0 nX: 1.
ｎ、 ＋１ ２ ＃ ｎ、： ３１ ｎ、： ４＃ Ｎ” ’ｏ ＋ｎｌ−１−ｎ２−１−ｎ３−）−ｎ。n, +1 2 ＃ n,: 31 n,: 4# N'' 'o +nl-1-n2-1-n3-)-n.
結果を表−４に示した。The results are shown in Table-4.
表−４ジャガイモ疫病防除試験
試験例４ キーウリベと病防除試験
温室内でポットに育生したキュウリ（品種：相撲半日、
木葉２枚展開）に所定濃度の薬剤（供試化合物を前記製
剤例８の方法にて水利剤となし、これを水で所定濃度に
希釈したもの〕をスプレーガン（ｔ ａ ｉｃｙ／ｃａ
ｌ ）を使用して３鉢当９３０ゴ散布し風乾した。べと
病に罹病したキ為つリ葉病斑部よりべと病菌を採取し、
脱塩水で胞子浮遊液を調製し、それを゛噴霧接種した。Table 4 Potato late blight control test Test example 4 Cucumber and disease control test Cucumbers grown in pots in a greenhouse (variety: Sumo half-day,
A spray gun (taicy/ca.
1) was used to spray 930 ml per 3 pots and air-dried. Downy mildew bacteria were collected from the diseased spots on the leaves of Kitametsuri infected with downy mildew.
A spore suspension was prepared with demineralized water and inoculated by spraying.
接種したポットは直に１８〜２０℃、湿度９５チ以上の
状態に２４時間保ったのち、温室（室温１８〜２７℃〕
に移し、７日後、病斑の形成程度を調査した。The inoculated pots were immediately kept at 18-20°C and a humidity of 95°C or higher for 24 hours, and then placed in a greenhouse (room temperature 18-27°C).
After 7 days, the degree of lesion formation was examined.
評価基準および罹病度表示方法は試験例３に示したとう
りである。The evaluation criteria and disease severity display method were as shown in Test Example 3.
結果を表−５に示した。The results are shown in Table-5.
表−４および表−５に示した結果より本発明化合物群は
、ジャガイモ疫病、キーウリベと病等、藻菌類が引き起
こす植物病害に対して従来より広く使用されてきている
市販の殺菌剤に比べ、極めて高い防除効果を示している
ことは明らかである。The results shown in Tables 4 and 5 show that the compound group of the present invention is more effective than commercially available fungicides that have been widely used in the past against plant diseases caused by algal fungi, such as late blight of potato and mildew. It is clear that it has an extremely high pesticidal effect.
また、化学構造が比較的近似である前出文献に記載の２
−ベンゾイルアミノプロピオニトリル、あるいは２−ベ
ンゾイルアミノブチ゛ロニトジル等テは病害防除効果は
ほとんど認められず、本発明化合物はこれまでのいかな
る知見からも予想できない優れた特性を有することは明
らかである。In addition, the two compounds described in the above-mentioned document whose chemical structures are relatively similar
-benzoylaminopropionitrile or 2-benzoylaminobutyronitrile, etc., have almost no disease control effect, and it is clear that the compounds of the present invention have excellent properties that could not be predicted based on any previous knowledge. be.
以上の説明より明らかなように、本発明に係るアシルア
ミノバレロニトリル誘導体は、水田用除草剤としてはこ
れまでの除草剤では期し得なかった適期幅の広い優れた
除草効果を示す。また農園芸用殺菌剤としては土壌病害
を含む各種作物の藻菌類による各種病害に対して、従来
の市販薬剤では効果が期待できないような低薬量、低濃
度で優れた防除効果を有する。本発明に係るアシルアミ
ノバレロニトリル誘導体を含有する農薬は除草剤および
農園芸用殺菌剤として優れた特性を具備し有用である。As is clear from the above description, the acylaminovaleronitrile derivative according to the present invention exhibits an excellent herbicidal effect with a wide range of suitable periods, which was not expected with conventional herbicides as a herbicide for rice fields. Furthermore, as a fungicide for agriculture and horticulture, it has excellent control effects against various diseases caused by algae and fungi on various crops, including soil diseases, at a low dose and concentration, which is not expected to be effective with conventional commercially available drugs. The agricultural chemical containing the acylaminovaleronitrile derivative according to the present invention has excellent properties and is useful as a herbicide and a fungicide for agriculture and horticulture.
Claims (4)
、置換ピリジル基、フリル基、置換フリル基、チエニル
基、置換チエニル基またはナフチル基を示す）で表され
るアシルアミノバレロニトリル誘導体。(1) General formula (I) ▲Mathematical formula, chemical formula, table, etc.▼(I) (In the formula, A is a phenyl group, substituted phenyl group, pyridyl group, substituted pyridyl group, furyl group, substituted furyl group, thienyl group , a substituted thienyl group or a naphthyl group).
級アルキル基、低級ハロアルキル基、低級アルコキシ基
、メチレンジオキシ基、ニトロ基またはシアノ基の一種
以上で置換されたフェニル基、またはハロゲン原子もし
くは低級アルキル基で置換されていてもよいピリジル基
、フリル基またはチエニル基である特許請求の範囲第１
項記載のアシルアミノバレロニトリル誘導体。(2) In general formula (I), A is a phenyl group substituted with one or more of a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a methylenedioxy group, a nitro group, or a cyano group, or a halogen atom or a pyridyl group, furyl group or thienyl group which may be substituted with a lower alkyl group.
The acylaminovaleronitrile derivative described in .
、置換ピリジル基、フリル基、置換フリル基、チエニル
基、置換チエニル基またはナフチル基を示す）で表され
る酸クロリドと式（III）▲数式、化学式、表等があり
ます▼（III） で表されるα−アミノバレロニトリルと反応させること
を特徴とする一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （式中、Ａは前記の意味を示す）で表されるアシルアミ
ノバレロニトリル誘導体の製造法。(3) General formula (II) A-COCl(II) (wherein A is a phenyl group, substituted phenyl group, pyridyl group, substituted pyridyl group, furyl group, substituted furyl group, thienyl group, substituted thienyl group or naphthyl group) The general formula (I) is characterized by reacting the acid chloride represented by the formula (III) with α-aminovaleronitrile represented by the formula (III) There are mathematical formulas, chemical formulas, tables, etc.▼(I) A method for producing an acylaminovaleronitrile derivative represented by (in the formula, A indicates the above meaning).
、置換ピリジル基、フリル基、置換フリル基、チエニル
基、置換チエニル基またはナフチル基を示す）で表され
るアシルアミノバレロニトリル誘導体を有効成分として
含有することを特徴とする水田用除草剤および農園芸用
殺菌剤。(4) General formula (I) ▲Mathematical formula, chemical formula, table, etc.▼(I) (In the formula, A is a phenyl group, substituted phenyl group, pyridyl group, substituted pyridyl group, furyl group, substituted furyl group, thienyl group , a substituted thienyl group or a naphthyl group) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15512385A JPH0655705B2 (en) | 1985-07-16 | 1985-07-16 | Acylaminovaleronitrile derivatives, a method for producing the same, herbicides and agricultural / horticultural fungicides containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15512385A JPH0655705B2 (en) | 1985-07-16 | 1985-07-16 | Acylaminovaleronitrile derivatives, a method for producing the same, herbicides and agricultural / horticultural fungicides containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6216453A true JPS6216453A (en) | 1987-01-24 |
| JPH0655705B2 JPH0655705B2 (en) | 1994-07-27 |
Family
ID=15599061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15512385A Expired - Lifetime JPH0655705B2 (en) | 1985-07-16 | 1985-07-16 | Acylaminovaleronitrile derivatives, a method for producing the same, herbicides and agricultural / horticultural fungicides containing them |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0655705B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5041601A (en) * | 1989-10-06 | 1991-08-20 | Virginia Tech Intellectual Properties, Inc. | Preparation of acyclic bis (reissert compounds) |
| JP2009029799A (en) * | 2007-06-29 | 2009-02-12 | Sumitomo Chemical Co Ltd | Plant disease-controlling agent and method for controlling plant disease |
| JP2009029798A (en) * | 2007-06-29 | 2009-02-12 | Sumitomo Chemical Co Ltd | Plant disease control agent, and plant disease control method |
| EP2179651A1 (en) * | 2007-06-29 | 2010-04-28 | Sumitomo Chemical Company, Limited | Plant disease control agent, and plant disease control method |
-
1985
- 1985-07-16 JP JP15512385A patent/JPH0655705B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5041601A (en) * | 1989-10-06 | 1991-08-20 | Virginia Tech Intellectual Properties, Inc. | Preparation of acyclic bis (reissert compounds) |
| JP2009029799A (en) * | 2007-06-29 | 2009-02-12 | Sumitomo Chemical Co Ltd | Plant disease-controlling agent and method for controlling plant disease |
| JP2009029798A (en) * | 2007-06-29 | 2009-02-12 | Sumitomo Chemical Co Ltd | Plant disease control agent, and plant disease control method |
| EP2179651A1 (en) * | 2007-06-29 | 2010-04-28 | Sumitomo Chemical Company, Limited | Plant disease control agent, and plant disease control method |
| EP2179651A4 (en) * | 2007-06-29 | 2012-07-11 | Sumitomo Chemical Co | Plant disease control agent, and plant disease control method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0655705B2 (en) | 1994-07-27 |
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