JPH0655704B2 - Acylaminopropionitrile derivatives, method for producing the same, herbicides and agricultural / horticultural fungicides containing them - Google Patents
Acylaminopropionitrile derivatives, method for producing the same, herbicides and agricultural / horticultural fungicides containing themInfo
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- JPH0655704B2 JPH0655704B2 JP14453685A JP14453685A JPH0655704B2 JP H0655704 B2 JPH0655704 B2 JP H0655704B2 JP 14453685 A JP14453685 A JP 14453685A JP 14453685 A JP14453685 A JP 14453685A JP H0655704 B2 JPH0655704 B2 JP H0655704B2
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- acylaminopropionitrile
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は一般式(I) (式中、Rは水素原子、ハロゲン原子、低級アルキル基
または低級アルコキシ基を示し、nは1ないし5の整数
を示し、nが2以上の整数を示す場合はRは同一でも異
ってもよく、Xは酸素原子または硫黄原子を示す)で表
されるアシルアミノプロピオニトリル誘導体、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 Field of Application] The present invention provides compounds represented by general formula (I) (In the formula, R represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, n represents an integer of 1 to 5, and when n represents an integer of 2 or more, R may be the same or different. Often, X represents an oxygen atom or a sulfur atom), an acylaminopropionitrile derivative represented by the formula, a method for producing the same, and a herbicide for paddy fields or a fungicide for agricultural and horticultural use containing them as an active ingredient.
従来より農園芸上有用なアミド誘導体は非常に多くの研
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。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(メプロニル)などが知られている。
しかし、本発明で示されるようなアシルアミノプロピオ
ニトリル誘導体について生理活性を調べた報告はない。Many studies have been conducted on amide derivatives useful in agriculture and horticulture, and many compounds showing characteristic physiological activity have been found and put to practical use. For example, as a substituted benzamide derivative, ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionate (benzoylpropethyl) is used as a herbicide, and 2-methyl-N- (3 is used as a fungicide. -Isopropoxyphenyl) benzamide (mepronil) and the like are known.
However, there is no report of examining the physiological activity of the acylaminopropionitrile derivative as shown in the present invention.
ケミカル アブストラクツ(Chemical Abstracts)によ
れば本発明で示されるようなアシルアミノプロピオニト
リル誘導体と近縁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 オブ
ザ ケミカル ソサイエティ(J.Chem.Soc.),196
3、2143〜2150ページ、およびシンセシス(Sy
nthesis)、1972、11号、622〜624には2
−ベンゾイルアミノブチロニトリル、あるいはビュレタ
ン デ ラ ソシエテ シミーク ド フランセ(Bul
l.Soc.Chim.Fr.)、1969、11号、4108〜41
11ページ、およびユスタス リービッヒ アンナーレ
ン デル ヘミー(Justus Liebigs Ann.Chem.),19
72、764、69〜93ページには2−ベンゾイルア
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。According to Chemical Abstracts, there are only a few examples of the synthesis of acylamino saturated aliphatic derivatives closely related to the acylaminopropionitrile derivative as shown in the present invention. For example, Journal of
The Chemical Society (J.Chem.Soc.), 196
3 , pages 2143 to 2150, and synthesis (Sy
nthesis), 1972 , No. 11, 622-624 is 2
-Benzoylaminobutyronitrile, or buretane de la Societe de France (Bul
l.Soc.Chim.Fr.), 1969 , No. 11, 4108-41.
Page 11, and Justus Liebigs Ann.Chem., 19
72, 764 , pp. 69-93 exemplify the synthesis of 2-benzoylaminopropionitrile. However, these references do not mention the physiological activity 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。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。Conventionally, many herbicides such as amide compounds, thiol carbamate compounds, and diphenyl ether compounds have been developed and put to practical use as herbicides for paddy fields, but their performance is still insufficient. The amide compound butachlor is used before and after rice planting, but the chemical damage to rice caused by temperature conditions and the like has always been a problem. The use of thiol carbamate compound molinate is regulated due to the problem of fish toxicity. Bench-o-curve poses a problem of phytotoxicity to paddy rice under reducing conditions of soil. Although diphenyl ether compounds are used immediately after rice planting like butachlor, their activity becomes extremely low when the treatment time 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く普及し、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 are widely used in practice because they have excellent performance in one aspect, and are used, but defects and problems are gradually becoming apparent,
There is a strong demand for new herbicides for paddy fields that have superior performance and are easier to use.
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ル、TPN、キャプタ
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、治療的な効果は全く期待できない。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。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。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−(2,6−ジメチルフェニル)−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。On the other hand, compounds having various chemical structures have been put to practical use as agricultural and horticultural fungicides, but captafol, TPN, captan or dithiocarbamate drugs are widely used for plague and downy mildew of various crops. It is commonly used and has contributed to increased crop production. However, all of these compounds have a prophylactic effect against plague and downy mildew, and no therapeutic effect can be expected at all. Therefore, there is a big drawback that a sufficient effect cannot be expected already when the occurrence of disease is recognized. Considering the actual application of chemicals for controlling crop diseases, the chemicals will be applied more or less after the occurrence of the disease, and complete disease control is difficult with these compounds. In addition, the concentration of the compound having a controlling effect is also extremely high, which is regarded as a problem from the safe use of the controlling agent. In order to improve these points, research on new control agents has been earnestly pursued, and at present, N-phenylalanine ester derivatives having excellent therapeutic effect, such as metalaxyl [N- (2,6-dimethylphenyl) -N- (, 2'-methoxyacetyl) alanine methyl ester] and the like have been developed and are being put to practical use worldwide. But these N-
As for the phenylalanine ester derivative, its drug-resistant bacterium has already been regarded as a problem.
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、その製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, a compound having extremely excellent properties as a herbicide for paddy fields and a fungicide for agricultural and horticultural use, its production method and harmful weed control agents containing them as active ingredients and harmful An object is to provide a microbial 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、魚毒性も低く、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 suitable period for paddy fields, has little phytotoxicity to paddy rice, and has low fish toxicity. As a fungicide, it has prophylactic and therapeutic effects against epidemics and downy mildews of various crops. A new compound having a broad application range, which has both of them and has an excellent control effect against soil diseases such as seedling wilting of various crops, a simple and high-yield method for producing the novel compound, and them. An object of the present invention is to provide a useful agrochemical composition containing
前記課題を解決するためアシルア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、アシルアミノプロピ
オニトリル誘導体が、前記先行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く、また水稲に対する薬害も少
なく魚毒性も低く、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。As a result of intensive studies on an acylaminoalkylnitrile derivative to solve the above-mentioned problems, an acylaminopropionitrile derivative has a physiological activity that cannot be predicted at all from the prior art, and as a paddy herbicide, It has a wide range of suitable periods, low phytotoxicity to paddy rice, and low fish toxicity. On the other hand, as a fungicide, it has both preventive and therapeutic effects against epidemics and downy mildews of various crops. The present invention has been completed by finding that it also exhibits an excellent control effect against soil diseases such as seedling wilt disease.
本発明に係るアシルアミノプロピオニトリル誘導体は一
般式(I) (式中、Rは水素原子、ハロゲン原子、低級アルキル基
または低級アルコキシ基を示し、nは1ないし5の整数
を示し、nが2以上の整数を示す場合はRは同一でも異
ってもよく、Xは酸素原子または硫黄原子を示す)で表
される新規な化合物である。The acylaminopropionitrile derivative according to the present invention has the general formula (I) (In the formula, R represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, n represents an integer of 1 to 5, and when n represents an integer of 2 or more, R may be the same or different. Often, X is a novel compound represented by an oxygen atom or a sulfur atom).
本発明はさらに前記一般式(I)で表されるアシルアミノ
プロピオニトリル誘導体の新規な製造法についても、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。Further, as a result of diligent studies on the novel method for producing an acylaminopropionitrile derivative represented by the general formula (I), the present invention has found a method for obtaining a target product in a high yield and completed the present invention.
すなわち、本発明に係るアシルアミノ誘導体であるアシ
ルアミノプロピオニトリル誘導体の製造法は一般式(II) (式中、Rおよびnは前記の意味を示す。)で表される
酸クロリドと一般式(III) (式中、Xは前記の意味を示す)で表されるα−アミノ
プロピオニトリル誘導体とを反応させることを特徴とす
る製造法である。That is, the method for producing an acylaminopropionitrile derivative which is an acylamino derivative according to the present invention has the general formula (II) (Wherein R and n have the above-mentioned meanings) and the acid chloride represented by the general formula (III) (In the formula, X has the above-mentioned meaning.) The production method is characterized by reacting with an α-aminopropionitrile derivative.
一般式(I)で表される本発明化合物の製造方法を反応図
式Aにより以下に説明する。The production method of the compound of the present invention represented by the general formula (I) will be described below by the reaction scheme A.
反応図式A (式中、R、nおよびXは前記の意味をしめす。) 一般式(VI)OHC-CH2XCH3(式中、Xは酸素原子または硫
黄原子を示す)で表されるアルデヒドをアンモニアおよ
びHCNの存在下にシュトレッカー反応条件下で反応さ
せてα−アミノプロピオニトリル(III)を得る。つい
で、これを酸受容体の存在下で酸クロリド(II)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、ピリジン等の有機塩基、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
酸化ナトリウム、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。ピリジンは容剤
と酸受容体の両方として用い得る。この反応は中間体の
α−アミノプロピオ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プロピオ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
および精製することが可能である。Reaction scheme A (In the formula, R, n and X have the above-mentioned meanings.) The aldehyde represented by the general formula (VI) OHC—CH 2 XCH 3 (wherein, X represents an oxygen atom or a sulfur atom) is converted into ammonia and The reaction is performed under the Strecker reaction condition in the presence of HCN to obtain α-aminopropionitrile (III). This is then reacted with acid chloride (II) in the presence of acid acceptor. Examples of acid acceptors include, but are not limited to, organic bases such as triethylamine, dimethylaniline, pyridine, and inorganic bases such as ammonia, potassium carbonate, sodium carbonate, sodium bicarbonate, sodium hydroxide, ammonium carbonate. Not a thing. This reaction is preferably carried out in a solvent or diluent. Pyridine can be used as both a bulking agent and an acid acceptor. This reaction is not desirable because the thermal stability of the intermediate α-aminopropionitrile is not good, and it is desirable to carry out it under cooling because it is an exothermic reaction. The desired acylaminopropionitrile derivative thus obtained can be easily isolated and purified by a conventional method such as recrystallization or 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
るアシルアミノプロピオ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。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、製剤の剤型、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0.1〜1
00gが適当であり、望ましくはアール当り0.5〜25
gである。その殺草活性はイネ科雑草に対して特徴的に
強いが、他の雑草に対しては枯殺させない場合でも強い
抑制効果を示す。こうした特性は場合によっては混合剤
またはタンクミックス等による混合施用を考えるとき極
めて有利に作用すると考えられる。特にカヤツリグサ科
の雑草たとえばタマガヤツリ、ホタイル等に対し、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。Further, the present invention provides a herbicide for paddy fields and an agricultural and horticultural fungicide characterized by containing the acylaminopropionitrile derivative represented by the general formula (I) according to the present invention as an active ingredient. Is. When the compound of the present invention is used as a herbicide for paddy fields, its application amount varies depending on the growth stage of weeds, the type of weeds, the dosage form of the formulation, the application method and various environmental conditions, etc., but is usually 0.1 to 1 per are.
00g is suitable, preferably 0.5 to 25 per are
It is g. Its herbicidal activity is characteristically strong against grass weeds, but it shows a strong inhibitory effect on other weeds even when they are not killed. In some cases, such characteristics are considered to be extremely advantageous when considering a mixed application such as an admixture or a tank mix. In particular, similar tendencies are observed with respect to weeds of Cyperaceae, such as cyperus edulis, phosteria, etc., and depending on the type of other weeds, although there are strengths.
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、使い易い雑草剤になりうる。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異るも
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。Further, the application period of the compound of the present invention varies widely from before the emergence of weeds to the growing season. Compared with the known amide-based compound butachrome and thiolcarbamate-based compound Benchiocarb, the compound of the present invention has a much wider suitable period of use, has excellent characteristics not present in the past, and has less restrictions on the treatment time, and can be used. Can be an easy weed pill. Although the herbicidal activity against Taenia japonicum naturally varies in practical dose depending on the treatment time, while Bentocarb and butachlor are not sufficiently effective in practical dose in 3.5 leaf stage Taenia japonica, the compound of the present invention It shows an activity that can withstand practical use at doses below the practical dose.
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 a very low phytotoxicity to transplanted paddy rice regardless of the treatment time.
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
病に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に対しても有効である。
しかも予防的、治療的効果を合せもつ。When the compound of the present invention is used as an agricultural and horticultural fungicide, it is not only effective against the plague and downy mildew of various crops caused by algae, but also against the diseases caused by other various plant pathogens. Also effective.
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、ブドウべ
と病、キュウリべと病、ホップべと病、シュンギクべと
病、あるいはアファノミセス属菌、ビシウム属菌等によ
る各種作物苗立枯病が挙げられる。Major diseases to be controlled are potato disease, tomato disease, tobacco disease, strawberry disease, adzuki bean disease, grape downy mildew, cucumber downy mildew, hop downy mildew, sungiku downy mildew, or Aphanomyces spp., Visium spp. Examples include various crop seedling blight caused by fungi.
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が適当であり、望
しくは50〜500ppmである。As a method of applying the compound of the present invention, seed disinfection, foliage spray,
Soil treatment and the like can be mentioned, but any application method usually used by those skilled in the art is sufficiently effective. The applied amount and applied concentration are target crop, target disease, degree of disease occurrence,
Depending on the formulation of the compound, application method and various environmental conditions, when sprayed, it is 5 to 200 g per are.
Is suitable, and is preferably 10 to 100 g per are. A suitable spray 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
たは肥効性物質との混合使用は勿論のこと、これらとの
混合製剤も可能である。Herbicides and agricultural and horticultural fungicides of the present invention include other fungicides and insecticides, herbicides, plant growth regulators and other pesticides, as well as mixed use with soil improvers or fertilizers, with these, Mixed preparations of 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。ここでいう担体とは、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 present invention may be applied as such, but are preferably applied in the form of a composition in admixture with a carrier including a solid or liquid diluent. As used herein, the term carrier means a synthetic or natural inorganic or organic substance that is formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transportation, 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、ケイソウ土、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, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, inorganic substances such as ammonium sulfate, soybean flour, sawdust, plant organic substances such as flour, and the like. Examples include 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、ケロシン、鉱油などのパラフィ
ン系炭化水素、四塩化炭素、クロロホルム、ジクロロエ
タンなどのハロゲン化炭化水素、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、プロパノール、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, paraffin hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloroethane, ketones such as acetone and methyl ethyl ketone. , Ethers such as dioxane and tetrahydrofuran, alcohols such as methanol, propanol and ethylene glycol, dimethylformamide, dimethylsulfoxide 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。Further, in order to enhance the efficacy of the compound of the present invention, the following auxiliary agents can be used alone or in combination according to the purpose in consideration of the dosage form of the preparation, the application scene and the like.
乳化、分散、拡展、湿潤、結合、安定化等の目的ではリ
グ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 lignin sulfonate, nonionic surfactants such as alkylbenzene sulfonate, alkyl sulfate, calcium stearate, wax etc. Lubricants, stabilizers such as isopropylhydrodiene phosphate, and others such as methyl cellulose, carboxymethyl cellulose, casein, and gum arabic. However, these components are not limited to the 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%、水和剤では
10〜90重量%、粒剤では0.1〜20重量%、フロワ
ブル剤では10〜90重量%である。The amount of the active ingredient in the composition of the compound of the present invention is usually 0 in powder.
5-20% by weight, 5-30% by weight for emulsions, 10-90% by weight for wettable powders, 0.1-20% by weight for granules, 10-90% by weight for flowable agents.
本発明に係る一般式(1)で表わされるアシルアミノプロ
ピオニトリル誘導体の代表例を表−1に示す。Representative examples of the acylaminopropionitrile derivative 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 described with reference to synthetic examples.
合成例1 2−ベンゾイルアミノ−3−メトキシプロピオニトリル
(化合物番号−1)の合成 塩化アンモニウム6.4g、シアン化ナトリウム5.4gを水
30mに溶解し、これにエチルエーテル15m、28
%アンモニア水10mを加えた。氷浴にて10℃に冷
却した。攪はん下にメトキシアセトアルデヒド(安定剤
として水13%を含む)6.9gを滴下し、さらに同温度
で24時間攪はんした。反応終了後エーテル層を分液
し、水層を3度エーテル抽出したのち、エーテル層をあ
わせ硫酸ナトリウムで乾燥した。エーテル層を減圧下に
濃縮し、残されたエチルエーテル100mを加え、0
〜5℃に冷却した。ついでトリエチルアミン5.1gを加
えた後、攪はん下にベンゾイルクロリド5.6gを滴下し
た。滴下終了後、さらに同温度で1時間攪はんした。水
50m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。残さをシリカゲルカラムクロマトグラフ
ィにより精製した。ヘキサン−酢酸エチル系より溶出
し、所望の2−ベンゾイルアミノ−3−メトキシプロピ
オニトリルを固体として2.8g得た。収率36.6% m.p.90〜92℃ 合成例2 2−(3,5−ジクロロベンゾイルアミノ)−3−メチ
ルチオプロピオニトリル(化合物番号−12)の合成 塩化アンモニウム6.4g、シアン化ナトリウム5.4gを水
30mに溶解し、これにエチルエーテル15m、28
%アンモニア水10mを加えた。氷浴にて10℃に冷
却した。攪はん下にメチルチオアセトアルデヒド9.0g
を滴下し、さらに同温度で24時間攪はんした。反応終
了後エーテル層を分液し、水層を3度エーテル抽出した
のち、エーテル層をあわせ硫酸ナトリウムで乾燥した。
エーテル層を減圧下に濃縮し、残さにエチルエーテル1
00mを加え、0〜5℃に冷却した。ついでトリエチ
ルアミン5.1gを加えた後、攪はん下に3,5−ジクロ
ロベンゾイルクロリド6.2gを滴下した。滴下終了後、
さらに同温度で1時間攪はんした。水50m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。残
さをシリカゲルカラムクロマトグラフィにより精製し
た。ヘキサン−酢酸エチル系より溶出し、所望の2−
(3,5−ジクロロベンゾイルアミノ)−3−メチルチ
オプロピオニトリルを固体として2.4g得た。収率28.0
% m.p.120〜125℃ 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。Synthesis Example 1 Synthesis of 2-benzoylamino-3-methoxypropionitrile (Compound No.-1) Ammonium chloride 6.4 g and sodium cyanide 5.4 g were dissolved in water 30 m, and ethyl ether 15 m, 28 was added thereto.
10m% aqueous ammonia was added. It was cooled to 10 ° C in an ice bath. 6.9 g of methoxyacetaldehyde (containing 13% of water as a stabilizer) was added dropwise under stirring, and the mixture was further stirred at the same temperature for 24 hours. After completion of the reaction, the ether layer was separated, the aqueous layer was extracted with ether three times, and the ether layers were combined and dried over sodium sulfate. The ether layer was concentrated under reduced pressure, the remaining 100 ml of ethyl ether was added, and
Cooled to ~ 5 ° C. Then, after adding 5.1 g of triethylamine, 5.6 g of benzoyl chloride was added dropwise with stirring. After the completion of dropping, the mixture was further stirred at the same temperature for 1 hour. 50m of water was added to dissolve the precipitated triethylamine hydrochloride. The ether layer was separated, washed with water, dried and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography. Elution with a hexane-ethyl acetate system gave the desired 2-benzoylamino-3-methoxypropionitrile as a solid, 2.8 g. Yield 36.6% mp 90-92 ° C Synthesis Example 2 Synthesis of 2- (3,5-dichlorobenzoylamino) -3-methylthiopropionitrile (Compound No.-12) 6.4 g of ammonium chloride and 5.4 g of sodium cyanide were dissolved in 30 m of water, and ethyl ether was added thereto. 15m, 28
10m% aqueous ammonia was added. It was cooled to 10 ° C in an ice bath. 9.0g of methylthioacetaldehyde under stirring
Was added dropwise, and the mixture was stirred at the same temperature for 24 hours. After completion of the reaction, the ether layer was separated, the aqueous layer was extracted with ether three times, and the ether layers were combined and dried over sodium sulfate.
The ether layer was concentrated under reduced pressure and ethyl ether 1 was added to the residue.
00 m was added and cooled to 0-5 ° C. Then, after adding 5.1 g of triethylamine, 6.2 g of 3,5-dichlorobenzoyl chloride was added dropwise with stirring. After the dropping is completed,
Further, the mixture was stirred at the same temperature for 1 hour. 50m of water was added to dissolve the precipitated triethylamine hydrochloride. The ether layer was separated, washed with water, dried and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography. Elute from the hexane-ethyl acetate system to give the desired 2-
2.4 g of (3,5-dichlorobenzoylamino) -3-methylthiopropionitrile was obtained as a solid. Yield 28.0
% Mp120-125 ℃ Next, the method for producing the paddy field herbicide or agricultural / horticultural fungicide of the present invention will be described with reference to 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「重量部」をあらわす。The active ingredient compounds are shown by the compound numbers in Table 1 above.
"Part" means "part by weight".
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10
0部を得た。Formulation Example 1 Dust Compound (1): 3 parts, diatomaceous earth: 20 parts, white clay: 30 parts and talc: 47 parts are uniformly pulverized and mixed to obtain Dust 10
I got 0 copies.
製剤例2 水和剤 化合物(2):30部、、ケイソウ土:44部、白土:2
0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
混合して水和剤100部を得た。Formulation Example 2 Wettable powder Compound (2): 30 parts, diatomaceous earth: 44 parts, clay: 2
0 parts, sodium ligninsulfonate: 1 part and sodium alkylbenzenesulfonate: 2 parts were uniformly pulverized and mixed to obtain 100 parts of a wettable powder.
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部およびソルボール(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 sorbole (surfactant manufactured by Toho Kagaku Co., Ltd.) 20 parts 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:78部、タルク:2
0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: 78 parts, talc: 2
0 parts and 1 part of sodium lignin sulfonate were mixed, an appropriate amount of water was added and kneaded, and then granulated by an ordinary method using an extrusion granulator and dried to obtain 100 parts of granules.
製剤例5 粒剤 化合物(10):7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:3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): 7 parts, polyethylene glycol nonylphenyl ether: 1 part, polyvinyl alcohol: 3 parts and clay: 89 parts are uniformly mixed, hydrolyzed and dried to obtain 100 parts of granules. It was
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 Dust Compound (6): 2 parts, calcium carbonate: 40 parts and clay: 58 parts were uniformly mixed to obtain 100 parts of a powder.
製剤例7 水和剤 化合物(5):50部、タルク: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, talc: 40 parts, sodium lauryl phosphate: 5 parts, sodium alkylnaphthalenesulfonate: 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:25部を
混合粉砕し、水和剤100部を得た。Formulation Example 8 Wettable powder Compound (6): 50 parts, sodium lignin sulfonate:
10 parts, sodium alkylnaphthalene sulfonate: 5
Parts, white carbon: 10 parts, and diatomaceous earth: 25 parts were mixed and pulverized to obtain 100 parts of a wettable powder.
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:3
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: 3
Parts, sodium lignin sulfonate: 2 parts, dioctyl sulfosuccinate sodium salt: 1 part and water 54 parts by wet grinding with a sand grinder to give a flowable agent 100.
I got a part.
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 an agricultural / horticultural fungicide will be described with reference to Test Examples. In the test examples, the following compounds were used as controls.
対照化合物 A:2−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 C:2−クロロ−2′,6′−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:ジエチルチノカルバミド酸S−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)〔ジネ
ブ〕 F:テトラクロロイソフタロニトリル〔TPN〕 対照化合物A、およびBは前出文献にて公知の化合物で
あり、C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、
キュウリべと病等の防除剤として市販の薬剤である。Control compound A: 2-benzoylaminopropionitrile B: 2-benzoylaminobutyronitrile C: 2-chloro-2 ', 6'-diethyl-N- (butoxymethyl) acetanilide [butachlor] D: diethyltinocarbamic acid S-p-chlorobenzyl [benchocarb] E: zinc ethylene bis (dithiocarbamate) [dineb] F: tetrachloroisophthalonitrile [TPN] Control compounds A and B are compounds known in the above literature, and C Is a pre-emergence treatment D is a commercially available herbicide for paddy field treatment for growing season. E and F are potato epidemics,
It is a drug commercially available as a control agent for cucumber downy mildew and the like.
試験例1 水田発生前除草試験 アール/5000ワグネルポットに土壌を詰め、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
て調製した粒剤を用いて湛水下に処理した。処理30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 Pre-emergence weeding test Earl / 5000 Wagner pots were filled with soil, and seeds of rice barley, broad-leaved weeds (Cygnus serrata, azena, eel, etc.), firefly, Heraomodaka, and Tamagaya periwinkle were sown,
It was flooded. Two paddy rice seedlings (2 to 3 leaf stage) that had been raised in advance were used as one strain, and the two strains were transplanted and grown in a greenhouse. One day after the transplantation of paddy rice and before the emergence of weeds, a predetermined amount of the test compound was treated under flooding with the granules prepared according to the method described in Formulation Example 5 above. After 30 days from the treatment, the occurrence of weeds and the 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
場合の風乾重と比較し、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 phytotoxicity against crops and the herbicidal effect against weeds were expressed according to the following evaluation criteria by comparing the generation or growth state of crops or weeds with the wind dry weight in the case of no treatment. The test compounds are shown by the 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: 〃 11〜40% 4: 〃 6〜10% 5: 〃 0〜5% 試験例2 水田生育期除草試験 アール/5000ワグネルポットに土壌を詰め、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
温室内に生育させた。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製剤例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30
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 criteria 0: Survival rate 91 to 100 in terms of air-dry weight ratio to untreated plot
% 1: 〃 71 to 90% 2: 〃 41 to 70% 3: 〃 11 to 40% 4: 〃 6 to 10% 5: 〃 0 to 5% Test Example 2 Paddy field weeding weeding test Earl / 5000 Wagner pots were filled with soil, and seeds of Taenia japonicus, broad-leaved weeds (European grass, Azena, Konagi, etc.), fireflies, Heraomodaka, and Tamagaya periwinkle were sown,
It was flooded. Two rice seedlings (2 to 3 leaf stage) that had been raised in advance were used as one strain, and the two strains were transplanted and grown in a greenhouse. During the weed growth period 12 days after transplanting the paddy rice, a predetermined amount of the test compound was treated under flooding with the granules prepared according to the method described in Formulation Example 4 above. Processing 30
The day after day, we investigated the occurrence of weeds and phytotoxicity to paddy rice. 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 phytotoxicity to crops and the growth state of weeds are shown 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
理でも、またこれまで除草効果が発揮され難かった生育
期処理でも幅広い除草活性を示し、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 Table 2 and Table 3, the compound group of the present invention has a wide range of pre-emergence treatment against various harmful weeds that are problematic in paddy fields, and treatment in the growing season where the herbicidal effect has been difficult to be exerted until now. It is clear that it is an excellent compound that exhibits herbicidal activity and has 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あるいは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, 2 described in the above-mentioned literature, which has a relatively similar chemical structure
Almost no herbicidal effect was observed with -benzoylaminopropionitrile, 2-benzoylaminobutyronitrile, etc., and it is clear that the compound of the present invention has excellent properties that cannot be predicted from any knowledge so far.
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の方法に準じて水和剤となし、これを水で所定濃
度に希釈したもの)をスプレーガン(1.0kg/cm2)を使
用して3鉢当り50m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17〜1
9℃、湿度95%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 epidemic control test Potato (variety: baron, plant height of about 25 cm) grown in a pot in a greenhouse was prepared with a drug having a predetermined concentration (test compound was made into a wettable powder according to the method of the above Preparation Example 8). Was diluted with water to a predetermined concentration) and sprayed with 50 m for 3 pots using a spray gun (1.0 kg / cm 2 ) and air dried. A zoospore suspension was prepared from potato blight that had been previously cultured on potato slices for 7 days. This suspension was spray-inoculated onto the potato plants sprayed with chemicals to give 17 to 1 test plants.
After being kept at 9 ° C. and a humidity of 95% or more for 6 days, the degree of formation of lesions 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り病度を求めた。The lesion area ratio was observed and evaluated for each leaf to determine the disease severity index, and the disease severity was determined for each plot by the following formula.
なお、評価基準は次のとおりである。 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% 〃 4: 〃 51%以上 n0:発病程度指数0の葉数 n1: 〃 1 〃 n2: 〃 2 〃 n3: 〃 3 〃 n4:発病程度指数4の葉数 N=n0+n1+n2+n3+n4 結果を表−4に示した。Disease severity index 0: Disease area ratio 0% 〃 1: 〃 1-5% 〃 2: 〃 6-25% 〃 3: 〃 26-50% 〃 4: 〃 51% or more n 0 : Disease severity index 0 Number of leaves n 1 : 〃 1 〃 n 2 : 〃 2 〃 n 3 : 〃 3 〃 n 4 : Number of leaves with disease severity index 4 N = n 0 + n 1 + n 2 + n 3 + n 4 The results are shown in Table-4. .
試験例4 キュウリべと病防除試験 温室内でポットに育生したキュウリ(品種:相摸半白、
本葉2枚展開)に所定濃度の薬剤(供試化合物を前記製
剤例8の方法に準じて水和剤となし、これを水で所定濃
度に希釈したもの)をスプレーガン(1.0kg/cm2)を使
用して3鉢当り30m散布し風乾した。べと病にり病
したキュウ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。接種したポ
ットは直ちに18〜20℃、湿度95%以上の状態に2
4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。 Test Example 4 Cucumber downy mildew control test Cucumbers grown in pots in a greenhouse (variety: Aijihanshiro,
A spray gun (1.0 kg / cm) with a predetermined concentration of a drug (the test compound was made into a wettable powder according to the method of the above Preparation Example 8 and diluted to a predetermined concentration with water) was spread on two true leaves. 2 ) was used to spray 30 m per 3 pots and air dried. Downy mildew fungi were collected from the spotted cucumber leaf spots affected by downy mildew, a spore suspension was prepared with demineralized water, and spray-inoculated. Immediately place the inoculated pot in a condition of 18 to 20 ° C and humidity of 95% or higher.
After keeping it for 4 hours, move it to a greenhouse (room temperature 18-27 ° C),
After 7 days, the degree of lesion formation was investigated.
評価基準およびり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 the method for displaying the degree of disease are the same as those described 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、キュウリべと病等、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。また、化学構造が比較的近似してい
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リル等
で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。 From the results shown in Table-4 and Table-5, the compounds of the present invention are compared to commercially available fungicides which have been widely used against plant diseases caused by algae such as potato epidemic, cucumber downy mildew, and the like. It is clear that it has a very high control effect. Further, 2-benzoylaminopropionitrile or 2-benzoylaminobutyronitrile or the like described in the above-mentioned literature, which has a relatively similar chemical structure, shows almost no disease control effect, and the compound of the present invention has been obtained so far. It is clear that it has excellent properties that cannot be predicted from any of the above findings.
以上の説明より明らかなように、本発明に係るアシルア
ミノプロピオニトリル誘導体は、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士壌病
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
ミノプロピオ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 acylaminopropionitrile derivative according to the present invention exhibits an excellent herbicidal effect as a paddy herbicide with a wide suitable period, which cannot be expected with conventional herbicides. Further, as a fungicide for agricultural and horticultural use, it has an excellent control effect against various diseases caused by algae of various crops including Shilomu disease, at a low dose and a low concentration that cannot be expected to be achieved by conventional commercially available agents. The pesticide containing the acylaminopropionitrile derivative according to the present invention is useful as a herbicide and a fungicide for agricultural and horticultural use because it has excellent properties.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 稲見 俊一 神奈川県横浜市戸塚区飯島町2070 (72)発明者 北條 祥賢 神奈川県横浜市戸塚区飯島町2882 (72)発明者 榊原 昌弘 神奈川県鎌倉市台4−5―45 審査官 西川 和子 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Shunichi Inami 2070 Iijima-cho, Totsuka-ku, Yokohama-shi, Kanagawa (72) Inventor Yoshinori Hojo 2882 Iijima-cho, Totsuka-ku, Yokohama-shi, Kanagawa (72) Inventor Masahiro Sakakibara Kamakura, Kanagawa 4-5-45 Ichidai Kazuko Nishikawa, Examiner
Claims (3)
または低級アルコキシ基を示し、nは1ないし5の整数
を示し、nが2以上の整数を示す場合はRは同一でも異
ってもよく、Xは酸素原子または硫黄原子を示す)で表
されるアシルアミノプロピオニトリル誘導体。1. A general formula (I) (In the formula, R represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, n represents an integer of 1 to 5, and when n represents an integer of 2 or more, R may be the same or different. Often, X represents an oxygen atom or a sulfur atom), and is an acylaminopropionitrile derivative.
または低級アルコキシ基を示し、nは1ないし5の整数
を示し、nが2以上の整数を示す場合はRは同一でも異
ってもよい)で表される酸クロリドと式(III) (式中、Xは酸素原子または硫黄原子を示す)。 で表されるα−アミノプロピオニトリル誘導体と反応さ
せることを特徴とする一般式(I) (式中、RおよびXは前記の意味を示す)で表されるア
シルアミノプロピオニトリル誘導体の製造法。2. General formula (II) (In the formula, R represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, n represents an integer of 1 to 5, and when n represents an integer of 2 or more, R may be the same or different. Acid chloride represented by formula (III) (In the formula, X represents an oxygen atom or a sulfur atom). The general formula (I) characterized by reacting with an α-aminopropionitrile derivative represented by (In the formula, R and X have the above meanings) A process for producing an acylaminopropionitrile derivative.
または低級アルコキシ基を示し、nは1ないし5の整数
を示し、nが2以上の整数を示す場合はRは同一でも異
ってもよく、Xは酸素原子または硫黄原子を示す)で表
されるアシルアミノプロピオ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。3. General formula (I) (In the formula, R represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, n represents an integer of 1 to 5, and when n represents an integer of 2 or more, R may be the same or different. Often, X represents an oxygen atom or a sulfur atom), and a paddy field herbicide and an agricultural / horticultural fungicide containing an acylaminopropionitrile derivative represented by the formula (I) as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14453685A JPH0655704B2 (en) | 1985-07-03 | 1985-07-03 | Acylaminopropionitrile derivatives, method for producing the same, herbicides and agricultural / horticultural fungicides containing them |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14453685A JPH0655704B2 (en) | 1985-07-03 | 1985-07-03 | Acylaminopropionitrile derivatives, method for producing the same, herbicides and agricultural / horticultural fungicides containing them |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS625948A JPS625948A (en) | 1987-01-12 |
JPH0655704B2 true JPH0655704B2 (en) | 1994-07-27 |
Family
ID=15364589
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14453685A Expired - Lifetime JPH0655704B2 (en) | 1985-07-03 | 1985-07-03 | Acylaminopropionitrile derivatives, method for producing the same, herbicides and agricultural / horticultural fungicides containing them |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0655704B2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108017557B (en) * | 2017-12-06 | 2020-11-24 | 中国科学院兰州化学物理研究所苏州研究院 | Cyanidation method for preparing nitrile compound |
-
1985
- 1985-07-03 JP JP14453685A patent/JPH0655704B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPS625948A (en) | 1987-01-12 |
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