JPS6084287A - Quinoxalinone derivative, its preparation and fungicide for agricultural and horticultural use - Google Patents
Quinoxalinone derivative, its preparation and fungicide for agricultural and horticultural useInfo
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- JPS6084287A JPS6084287A JP19274683A JP19274683A JPS6084287A JP S6084287 A JPS6084287 A JP S6084287A JP 19274683 A JP19274683 A JP 19274683A JP 19274683 A JP19274683 A JP 19274683A JP S6084287 A JPS6084287 A JP S6084287A
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Abstract
Description
【発明の詳細な説明】
本発明は新規キノキザリノン誘導体、その製造法及びそ
れ全有効成分として含有する農園芸用殺菌剤に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel quinoxalinone derivative, a method for producing the same, and an agricultural and horticultural fungicide containing the same as all active ingredients.
イネいもち病は稲（Ｃとって最大の病害でありこれを防
除するための薬剤は従来より強く要望さ扛ている。現在
いもち病防除剤としては水面施用による薬剤が比較的長
期間薬効が持続すること及び散布が容易なことから多く
使用されている。このような水面施用による薬剤にめら
れる性能としては、施用後すみやかに扇体に吸収されて
効果全発現し、その効果が長期間持続することがめられ
る。また、同じ薬剤を繰返し使用すると耐性菌出現の可
能性もあるので何種かの薬剤をローテーションして使用
する方法も望まれるが、このためにはタイプの異なる多
種類の薬剤が必要である。これらの要求に関して現在知
られているいもち病防除剤はまだ完成の域ｖｃ ｉｔ達
［７ていない。Rice blast is the biggest disease of rice (C), and there has been a strong demand for agents to control it.Currently, as blast control agents, agents applied to the water surface have a relatively long-lasting medicinal effect. It is widely used because it is easy to spray and spray.The characteristics of such water-applied chemicals are that they are quickly absorbed into the fan body after application, exhibiting their full effect, and their effects last for a long time. In addition, if the same drug is used repeatedly, there is a possibility that resistant bacteria will emerge, so it is desirable to use several types of drugs in rotation. The currently known blast control agents that meet these requirements are still far from being completed [7].
このような状況ＶＣｍみ本発明者らは各棟化会物のイイ
・いもち病防除作用について広範な試験４行い１本発明
のキノキザリノン誘導体がイネいもち病に対して水面施
用法で卓効を示すことを兄出した。Under such circumstances, the present inventors conducted extensive tests on the blast control action of various rice blast plants and found that the quinoxalinone derivatives of the present invention are highly effective against rice blast by surface application. My brother told me about it.
本発明は、一般式（Ｉ）；
（式中、ＲＩ″ｉ水素原子、低級アルギル基、ハロゲン
１献ｒま友はトリフルオロメチル基金、ｎば１捷たｎ、
２を１ｍは０または１を表す。）で表されるキノキザリ
ノン、誘導体、その製造法および農園芸用殺菌剤に関す
るものである。The present invention relates to the general formula (I);
2 to 1m represents 0 or 1. ), its derivatives, its production method, and agricultural and horticultural fungicides.
（二記一般式（Ｉ）で表される本発明化合物は、３壌性
構造？有するキノギザリノン誘導体であり。(The compound of the present invention represented by the general formula (I) is a quinogyzarinone derivative having a ternary structure.
文献未載の新規化合物である。従来、公知のキノキザリ
ノン誘導体としては、ジャーナル・オブ・ザ・ケミカル
−ソサイエティ［： Ｊｔ）ｕｒｎａｌ ｏｆ ｔｂｑ
（コｈｅｍｉｃａｌＳＯＣ１’３ｔｙ１８０４頁（１
９５５）］に記載されている化合物が知られているが、
それに比べて１本発明化合物は優れた生理活性を有し、
特に稲の主要な病害であるイネいもち病に卓越した効力
全示し２作業の容易な施用方法１例えば水面施用などに
使用が可能であり、長期間残効性を示す性能を有するも
のである。This is a new compound that has not been published in any literature. Conventionally, known quinoxalinone derivatives are listed in the Journal of the Chemical Society [: Jt)urnal of tbq
(ChemicalSOC1'3ty1804 page (1
955)] are known, but
In comparison, the compound of the present invention has excellent physiological activity,
In particular, it exhibits excellent efficacy against rice blast, a major rice disease, and can be used in two easy application methods, such as water surface application, and has a long-lasting residual effect.
次に、一般式（１）で表される本発明化合物の製造法に
ついて１反応式で示すと次の通りである。Next, the method for producing the compound of the present invention represented by the general formula (1) is shown in one reaction formula as follows.
但し、一般式（ＩＩＩ）および一般式（ＩＶ’）で表さ
れる化合物は、一般式（１）で表される本発明化合物に
包含されるものである。However, the compounds represented by the general formula (III) and the general formula (IV') are included in the compound of the present invention represented by the general formula (1).
（ＩＩ） （ＩＩＤ （反応式中、［（ニ水索原子、低級アルギル基。(II) (IID (In the reaction formula, [(dihydrocarbon atom, lower argyl group.
ハロゲン原子またはトリフルオロメチル基を表し、ｎは
１または２を表す。）
上記反応式〔Ａｌ ｖｃおいて、一般式（ＩＩＩ’）で
表される化合物は、インドリン（２，３−ジヒドロイン
ドール）あるいは１．２． ！ｌ、 ４−テトラヒドロ
キノリ／誘導体にジケテンを反応させることにより製造
できる。It represents a halogen atom or a trifluoromethyl group, and n represents 1 or 2. ) In the above reaction formula [Al vc, the compound represented by the general formula (III') is indoline (2,3-dihydroindole) or 1.2. ! It can be produced by reacting diketene with l, 4-tetrahydroquinolite/derivative.
ジケテンの伺加及び閉環の反応はワンボｙ Ｉ・で行う
ことができる。っ−まり一般式（Ｉ］）で表されるイン
ドリン（２，５−ジヒドロインドール）或いｌｌｄ １
．２．３．４−テトラヒドロキシリン誘導体全適当な溶
媒、たとえばベンゼン、トルエン。The diketene addition and ring closure reactions can be carried out in one boiler. Indoline (2,5-dihydroindole) represented by the general formula (I) or lld 1
．． 2.3.4-Tetrahydroxyphosphorus derivatives All suitable solvents such as benzene, toluene.
エーテル、ジメチルホルムアεド、ジオキサンあるいは
それらの混合溶媒中で適当な塩基剤たとえばピリジン、
トリエチルアミン等の触媒存在下、ジケテンを滴下し適
当な温度たとえば０〜１５０℃で０．５〜１５時間攪拌
し１次に適当な温度たとえば０〜１５０℃にてアルカリ
処理する仁とにより行う。A suitable base agent such as pyridine, ether, dimethylformamide, dioxane or a mixed solvent thereof.
In the presence of a catalyst such as triethylamine, diketene is added dropwise and stirred at a suitable temperature, for example 0 to 150°C, for 0.5 to 15 hours, followed by alkali treatment at a suitable temperature, for example 0 to 150°C.
ま之、上記反応式（Ｂ’）において、一般式債）で表さ
れる化合物は、一般式（ＩＩＩ）で表されるキノキザリ
ノン誘導体を還元または低級アルキル化またはハロゲン
化することにより製造することができる。However, in the above reaction formula (B'), the compound represented by the general formula (III) can be produced by reducing, lower alkylating or halogenating the quinoxalinone derivative represented by the general formula (III). can.
還元反応は一般式（１「）で表されるキノキザリノン誘
導体を適当な溶媒たとえばベンゼン、エーテル、エタノ
ール、メタノール、ジオキサン或いはそれらの混合溶媒
中で適当な還元剤たとえば水素化ホウ素ナトリウム、ハ
イドロサルファイドに代表されるＭ、ｓ、０．塩、亜鉛
、アルミニウムに代表される両性金属、亜硫酸及び亜硫
酸ナトリウムに代表されるＭ、Ｓｏ、塩、ヒドラジン−
ライ・−ニッケル或いはパラジウムカーボン。The reduction reaction is carried out by reacting the quinoxalinone derivative represented by the general formula (1) in a suitable solvent such as benzene, ether, ethanol, methanol, dioxane or a mixed solvent thereof with a suitable reducing agent such as sodium borohydride or hydrosulfide. M, s, 0. Salt, zinc, amphoteric metal represented by aluminum, M, So, salt represented by sulfite and sodium sulfite, hydrazine-
Lie - nickel or palladium carbon.
う羊−ニッケル触媒ドの水素添加等を用いて行う。It is carried out using hydrogenation of a sheep-nickel catalyst, etc.
低級アルキル化反応は、一般式（１■）で表されるキノ
キザリノンｄ導体を適当な溶媒たとえばベンゼン、トル
エン、エーテル、エタノール。In the lower alkylation reaction, the quinoxalinone d conductor represented by the general formula (1) is mixed with a suitable solvent such as benzene, toluene, ether, or ethanol.
メタノール、ジオキサン或いはそれらの混合溶媒中で適
当なアルキル化剤たとえばアセト酢酸エチルエステルに
代表される一般式（Ｖ）；０Ｈ，ｎｏ（ＥＦＴ（：！Ｏ
，Ｒ，（ｖ）（式中、Ｒ１は水素原子、低級アルキル基
または１・’） ７ ／ｌ／ オロメチル基全示し Ｒ
１は低級アルギル基を表す。）
で表される化合物全塩基たとえばピリジン、トリエチル
アミン２モルホリン、ピペリジン、ピロリジン等存在下
反応させ１次にアルカリ処理する仁とにより行う。In methanol, dioxane or a mixed solvent thereof, a suitable alkylating agent such as the general formula (V) represented by acetoacetic acid ethyl ester; 0H, no (EFT (:!O
, R, (v) (in the formula, R1 is a hydrogen atom, a lower alkyl group, or 1.') 7 /l/ All olomethyl groups R
1 represents a lower argyl group. ) is reacted in the presence of a total base such as pyridine, triethylamine, 2-morpholine, piperidine, pyrrolidine, etc., and then treated with an alkali.
−・ａゲン化反応ぽ、一般式硼）で表されるキノキザリ
ノン誘等体を適当な溶媒たとえばベンゼン、トルエン等
或いは無溶媒で適当々ハロゲン化剤たとえば塩化チオニ
ル、オキシ塩化リン。-.a Genation reaction The quinoxalinone derivative represented by the general formula 硼) is treated with a suitable solvent such as benzene, toluene, etc. or without a solvent with a suitable halogenating agent such as thionyl chloride or phosphorus oxychloride.
ホスゲン等全使用して行う。Perform using all phosgene etc.
これらの反応は適当な温度範囲としては、たとえば０〜
１５０℃また反応時間としては［１５〜１５時間が望ま
しい。The appropriate temperature range for these reactions is, for example, 0 to
The reaction time is preferably 150°C and 15 to 15 hours.
このようにして上記反応において得られた生成物が結晶
化する化合物のときはそのまま濾過後乾燥して、目的化
合物を得る。When the product thus obtained in the above reaction is a compound that crystallizes, it is directly filtered and dried to obtain the target compound.
また、生成物が結晶化し々い場合には、水に加えた後適
当な溶媒で抽出し、乾燥後濾過し溶媒分留去後目的とす
る化合物を得る。これらの目的化合物は、再結晶、蒸留
、カラムクロマトグラフィーなどで精製できる。If the product tends to crystallize, it is added to water, extracted with a suitable solvent, dried and filtered, and the solvent is distilled off to obtain the desired compound. These target compounds can be purified by recrystallization, distillation, column chromatography, etc.
本発明化合物をａ園芸用殺菌剤として使用する場合は直
接原体のままで使用してもよく、あるいは通常使用され
ている形態、すなわち粒剤。When the compound of the present invention is used as a horticultural fungicide, it may be used directly as a raw material, or in a commonly used form, ie, granules.
粉剤、微粒剤、水利剤、乳剤、油剤などいずれの製剤形
態で使用してもよい。各種製剤はその目的によって適宜
使いわけることが望ましい。It may be used in any formulation form such as powder, fine granules, aqueous solution, emulsion, or oil solution. It is desirable to use various preparations as appropriate depending on their purpose.
これらの製剤を作成するに当って担体は固体。In preparing these formulations, the carrier is solid.
膜体のいずれでもよい。そのような担体としては、植物
性担体、樹脂、粘土類、その他無機鉱物、水、溶剤類な
どがある。また、界面活性剤としては、アルキル硫酸エ
ステル類、アルキルアリールスルホン酸塩、ボリエ゛チ
レングリコールエーテル類、多価アルコールエステルＭ
ｌ’が固着剤１分散剤としては、カゼイン、ゼラチ７、
ＣＭＣ，アラビアゴムなどがあげられる。Any membrane body may be used. Examples of such carriers include vegetable carriers, resins, clays, other inorganic minerals, water, and solvents. In addition, as surfactants, alkyl sulfates, alkylaryl sulfonates, polyethylene glycol ethers, polyhydric alcohol esters M
l' is a fixing agent 1 and a dispersing agent is casein, gelatin 7,
Examples include CMC and gum arabic.
次に実施例によって本発明をさらに詳しく説明するが２
本発明はこれらの実施例のみに限定されるものではない
。Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited only to these examples.
実施例１
で表される化合物の製造
８−ニトロ−１，２，３，４−テトラヒドロキノリン１
１．６ｆ（６５ｍｍｏｔＬピリジン０，５２をトルエン
溶液２００ｄＫ溶解し、攪拌下５．４６９（６５ｍｍｏ
ｔ）のジケテンを滴下した。ジケテン滴下後、徐々に昇
温し、６０℃にて６時間攪拌した。放冷後、５Ｎ水酸化
す） ＩＪウム溶液１０〇−を加え３０分間攪拌を行ら
た。次に、希塩酸を用い、水層を酸性にした後、さらに
１０分間攪拌を行った。静置後トルエン層を分離し、水
洗、乾燥後溶媒全留去し、得られた粗結晶をベンゼン−
ｎ−へキサン混合溶媒にて攪拌化洗浄することにより目
的の化合物Ｍ１を得た。Example 1 Preparation of the compound represented by 8-nitro-1,2,3,4-tetrahydroquinoline 1
1.6f (65 mmotL) Pyridine 0.52 was dissolved in 200 dK of toluene solution and 5.469 (65 mmot
The diketene of t) was added dropwise. After dropping the diketene, the temperature was gradually raised and stirred at 60°C for 6 hours. After cooling, 100% of 5N hydroxide solution was added and stirred for 30 minutes. Next, the aqueous layer was made acidic using diluted hydrochloric acid, and then stirred for an additional 10 minutes. After standing still, the toluene layer was separated, washed with water, dried, and then the solvent was completely distilled off.
The desired compound M1 was obtained by stirring and washing with an n-hexane mixed solvent.
収量９．２ Ｏｆ （収率７０Ｘ）
実施例２
で表される化合物の製造
実施例１で得られた化合物（胚１）１．５ ？ （７，
４５ｍｍｏｔ）をメタノール−水（１：２混合溶媒）５
０ローに溶解させ、室温下１２Ｘ水素化ホウ素ナトリウ
ム溶液１．１８ ｔ （五７２ ｍｍｏｔ）を徐々に滴
下した。室温にて２０分間攪拌後減圧下メタノールを留
去することにより結晶を析出した。結晶をν別後水洗、
乾燥することにより目的の化合物Ｍ２全得た。Yield: 9.2 Of (yield: 70X) Example 2 Production of the compound represented by Example 1 Compound (embryo 1) obtained in Example 1: 1.5 ? (7,
45 mmot) in methanol-water (1:2 mixed solvent) 5
1.18 t (572 mmot) of 12X sodium borohydride solution was gradually added dropwise at room temperature. After stirring at room temperature for 20 minutes, methanol was distilled off under reduced pressure to precipitate crystals. After separating the crystals, wash with water.
By drying, the target compound M2 was completely obtained.
収量１．０９ ｔ （収率７９Ｘ）
実施例３
で表される化合物の製造
実施例１で得られ几化合物（％１）１．７５ｒ（ａ ６
６ ｍｍｏｔ）Ｙ＜エタノール１００ゴに溶解させアセ
ト酢酸エチルｉ、 ６８ ｔ （１２，９ｍｍｏｔ）及
びピペリジン２．６ｍｊｉ加え２．０時間還流する。Yield 1.09 t (Yield 79X) Example 3 Production of the compound represented by
6 mmot) Y < 100 g of ethanol, 68 t (12.9 mmot) of ethyl acetoacetate and 2.6 mji of piperidine were added, and the mixture was refluxed for 2.0 hours.
情冷祷１０％ＫＯ１４索溶液５０ｉｄを常温にて加ｊ３
０分間攪拌した。エタノールを減圧下留去後次に水５０
ｍｇ１加え、希塩酸を用いｐ［（を３に調節することに
より結晶が析出した。結晶をＦ別除去後ｐ液を希水酸化
カリウム溶液を用いｐＦ（１０以上とし減圧下、水を部
分的に除去することにより結晶が析出した。結晶をＦ別
分離後。Add 50 id of 10% KO14 solution at room temperature j3
Stirred for 0 minutes. After distilling off the ethanol under reduced pressure, 50% of water was added.
Crystals were precipitated by adjusting p[( to 3) using dilute hydrochloric acid. After removing the crystals separately from F, the p solution was adjusted to pF (at least 10) using dilute potassium hydroxide solution and water was partially removed under reduced pressure. Upon removal, crystals precipitated. After separating the crystals by F.
水洗、乾燥し１次にベンゼン−ｎ−ヘキサン混合浴はに
て洗浄することにより目的化合物Ｍ３を得た。 収ｉｉ
１．１０１Ｆ（収率６５Ｘ）実施例４
で表される化付物の製造
実施例１で得られた化合物（４１）１．０ｆ（４゜９５
ｍｍｏｔ）Ｋオキシ塩化り７１５ Ｉｆ加え２．０時間
還流した。放冷抜水水中に注入することにより黒色ター
ル状の物質が分離した。The target compound M3 was obtained by washing with water, drying, and then washing with a benzene-n-hexane mixed bath. Collection ii
1.101F (yield 65X) Example 4 Preparation of compound represented by Compound (41) obtained in Example 1 1.0f (4°95
mmot) K oxychloride 715 If was added and refluxed for 2.0 hours. A black tar-like substance was separated by injecting the water into the drained water.
氷水ヲデカンテーションにて分離除去後、夕一ル状の物
質をアセトンＫＭ解させ、活性炭にて処理した。減圧下
、アセトンを部分的に除去する°ことにより結晶が析出
した。結晶’ｒＰ別分離後エーテルにて洗浄、乾燥する
ことにより目的化合物Ｍ４を得た。After separation and removal using ice water decantation, the pellet-like substance was dissolved in acetone KM and treated with activated carbon. Crystals were precipitated by partially removing acetone under reduced pressure. After separation of the crystal 'rP, the target compound M4 was obtained by washing with ether and drying.
収量０．７３ｔ （収率６７Ｘ）
実施例１−４及び同様にして得られた化合物の融点、赤
外線吸収スペクトル及びマススペクトルデータを第１表
に示す。Yield: 0.73t (yield: 67X) Table 1 shows the melting points, infrared absorption spectra, and mass spectra data of Examples 1-4 and the compounds obtained in the same manner.
第１表
また、第２表に示す化合物も前記実施例と同様にして製
造できる。The compounds shown in Table 1 and Table 2 can also be produced in the same manner as in the above examples.
第 ２ 表
次に１本発明のｉＡ園芸用殺菌剤の配合例を具体的に挙
げて説明する。但し、これらのみに限定されるものでは
ない。以下の部は重址部を示す。Table 2 Next, formulation examples of the iA horticultural fungicide of the present invention will be specifically listed and explained. However, it is not limited to these only. The following section shows the heavy site section.
配合例１ 乳 剤
本発明化合物５０部、キシレン２５部、ソルボール２６
８０（東邦化手製：非イメーン性界面活性Ａｌｌとアニ
オン性界面活性剤との混合へ勿）５部及びジメチルホル
ムアミド２０部を混合して乳剤とする。Formulation Example 1 Emulsion 50 parts of the compound of the present invention, 25 parts of xylene, 26 parts of Sorbol
An emulsion was prepared by mixing 5 parts of 80 (manufactured by Toho Chemical Co., Ltd.: a mixture of non-image surfactant All and anionic surfactant) and 20 parts of dimethylformamide.
配合例２ 粉 剤
本発明化合物５部とクレー９５部とをよく粉砕混合して
有効成分含有せ５％の粉剤を得る。Formulation Example 2 Powder 5 parts of the compound of the present invention and 95 parts of clay are thoroughly ground and mixed to obtain a powder containing 5% of the active ingredient.
配合例３ 水和剤
本発明化合物２５部、ジ−クライトＡ（カオリン系クレ
ー：ジ−クライト工業Ｇ）商品名）６９部、ツルポール
５０３９（東邦化学製：非イオン性界面活性剤とアニオ
ン性界面活性剤と）混合物）５部、カープレックス（固
結防止剤）６部を混合粉砕して水和剤とする。Formulation Example 3 Wettable powder: 25 parts of the compound of the present invention, 69 parts of Zikryte A (kaolin clay: Zikryte Industries G, trade name), Tsurupol 5039 (manufactured by Toho Chemical Co., Ltd.: nonionic surfactant and anionic interface) A wettable powder is prepared by mixing and pulverizing 5 parts of the active agent mixture) and 6 parts of Carplex (an anti-caking agent).
配合例４ 粒 剤
本発明化合物１０部、ベントナイト２０部及びタルク７
０部を水と混合して押出した造粒機で造粒し、乾燥して
粒剤とする。なお、製斉１１中の種類及び混合割合或い
は本発明化合物の害１合は上記の各製剤例に限定される
ことなく、広い範囲で変更可能である。Formulation Example 4 Granules: 10 parts of the compound of the present invention, 20 parts of bentonite, and 7 parts of talc
0 part is mixed with water, granulated using an extrusion granulator, and dried to form granules. Incidentally, the type and mixing ratio in Preparation Formula 11, or the degree of harm of the compound of the present invention are not limited to the above-mentioned formulation examples, and can be varied within a wide range.
次に試験例により本発明化合物のイネいもち病防除作用
を明らかにする。Next, the rice blast control action of the compound of the present invention will be clarified through test examples.
試験例１ イネいもち病防除試験（蓮華散布試験）（予
防的散布）
径７αのポットに栽培した稲（日本晴；４〜５葉期）に
乳剤形態の本発明化合物をスプレーガンを用いて１５ｇ
ｔ／ｉポットの割合で散布した。散布１日後稲いもち病
病原菌（Ｐｙｒｉｃｕｌａｒｉ、ａｏｒｙｚ−＋ｑ ）
の胞子懸濁液を稲に噴霧接種し、２４〜２６℃、湿度９
０％以上の恒温室内に静置後さらに温室内にて病斑を出
現させた。病原菌接種５日後に一葉当りの病斑数を調査
し防除効果を調べた。Test Example 1 Rice blast control test (Lotus spraying test) (preventive spraying) 15 g of the present compound in emulsion form was applied to rice (Nipponbare; 4-5 leaf stage) grown in a pot with a diameter of 7α using a spray gun.
Sprayed at a ratio of t/i pot. 1 day after spraying Rice blast pathogen (Pyriculari, aoryz-+q)
A spore suspension of
After being left in a constant temperature room at 0% or higher, lesions were allowed to appear in a greenhouse. Five days after inoculation with the pathogen, the number of lesions per leaf was investigated to determine the control effect.
結果を第３表に示す。なお防除価は次式により算出した
。The results are shown in Table 3. The control value was calculated using the following formula.
４Ｘ印の対照化合物は、ジャーナル・オブ・ザ・ケミカ
ル・ンｔエティｒＪｏｕｒｒ＋ａｌ ｏｆ ｔｂｅ（ｌ
ｈｅｍｊｃａｌ ５ｏｃｉｅｔｙ １８０４頁（１９５
に記載されている化合物。The control compounds marked 4X are listed in the Journal of the Chemical Industry.
hemjcal 5ociety 1804 pages (195
Compounds listed in .
本＊ｒｌの柑叩什ｌ＋働け、市販のイネいもち病防除剤
。Book *rl's Kantakutenl + Work, a commercially available rice blast control agent.
第３表から明らかなとおり３環性化合物である本発明化
合物は防除価が１００Ｘとなり、イネいもち病菌を完全
に防除することができた。As is clear from Table 3, the compound of the present invention, which is a tricyclic compound, had a control value of 100X and was able to completely control the rice blast fungus.
これに対して対照化合物である本発明外のキノ１名
キザリノン誘導体では６０にの勧除価しか得られず１本
発明化合物よりはるかに効果が劣っていた。また、従来
優れたイネいもち病防除剤であるとされている従来化合
物も防除価が９５Ｘで本発明化合物より劣っていた。On the other hand, the control compound, a compound of the present invention, which is a compound of the present invention, quinolinone, gave a recommendation value of only 60, which was far inferior to the compound of the present invention. Furthermore, the conventional compound, which has been considered to be an excellent rice blast control agent, had a control value of 95X, which was inferior to the compound of the present invention.
試験例２
イネいもち病防除試鹸（薬剤土壌施用試験）径７ｃ！ｎ
のポットに栽培した稲（日本晴；６〜４葉期）に乳剤形
態の本発明化合物を土壌施用した。乳剤は水で希釈した
溶液を１ポット当り有効成分せが５グになるように土壌
表面に均一に施用した。施用７日後にイネいもち病病原
菌（Ｐｙｒｉｃｕ、Ｌｑ、ｒｉａ ｏｒｙｚａｅ ）の
胞子液を稲に噴霧接種し°４２４〜２６℃、湿度９０Ｘ
以上の恒温室に静置５）〕
後、さらに温室内にて病斑が出現するのを待った。病原
菌接種５日後に一葉当りの病斑数を調存し防除効果を調
べた。Test Example 2 Rice blast control test soap (chemical soil application test) Diameter 7c! n
The compound of the present invention in the form of an emulsion was applied to rice (Nipponbare; 6-4 leaf stage) grown in pots. The emulsion was diluted with water and applied uniformly to the soil surface so that each pot contained 5 grams of the active ingredient. Seven days after application, the spore liquid of the rice blast pathogen (Pyricu, Lq, ria oryzae) was sprayed and inoculated onto rice at 424-26°C and humidity 90X.
After leaving the specimens in the thermostatic chamber described above 5), the specimens were further kept in the greenhouse to wait for the appearance of lesions. Five days after inoculation with the pathogen, the number of lesions per leaf was recorded to examine the control effect.
結果を第４衣に示す。なお、防除価は試験例１と同様に
してめた。The results are shown in Figure 4. In addition, the control value was determined in the same manner as in Test Example 1.
第 ４ 表 ＊および＊＊印の対照化合物は前記と同じ。Table 4 Control compounds marked * and ** are the same as above.
第４表から明らかなとおり、３現性化合物である本発明
化合物は防除価が１００Ｘとなり。As is clear from Table 4, the compound of the present invention, which is a ternary compound, has a control value of 100X.
イネいもち病を完全に防除することができた。It was possible to completely control rice blast.
これに対して対照化合物である本発明外のキノギザリノ
ン誘導体では防除価が７５Ｘにすぎずはるかに効果が劣
っていた。また、従来のイネいもち防除剤でも８５Ｘの
防除価しか得られなかった。On the other hand, the control compound, a quinogyzarinone derivative other than the present invention, had a control value of only 75X, and was far less effective. Furthermore, even with conventional rice blast control agents, only a control value of 85X was obtained.
このように本発明のキノキザリノン誘導体は扇体に直接
散布した時も或いは土壌中に散布した時もイネいもち病
に対して著しい卓効を有することから明らかとなり１種
々の施用法が可能であり、目的に応じて最適な施用法を
選択できる。捷た。上記試験例において施用後７日月に
病原菌を感染させてもとの感染を完全に防除したことか
らも明らかなとおり本発明のキノキザリノン誘導体は薬
効の持続期間も長い非常に有効な薬剤である。As described above, it is clear that the quinoxalinone derivative of the present invention is extremely effective against rice blast both when it is applied directly to the fan or when it is applied to the soil, and various methods of application are possible. The most suitable application method can be selected depending on the purpose. I cut it. As is clear from the fact that in the above test example, the original infection was completely controlled when infected with pathogenic bacteria 7 days after application, the quinoxalinone derivative of the present invention is a very effective drug with a long-lasting medicinal effect.
特許出願人 日産化学工業株式会社 第１頁の続きPatent applicant: Nissan Chemical Industries, Ltd. Continuation of page 1
Claims (1)
またはト１１フルオロメチＡ４’を表し、ｎは１または
２を９ｍは０またば１を表す。） で表されるキノキザリノ／誘導体。 （２） 次式（旧； （式中、ｎは１または２を表す。） で表されるインドリン（２，５−ジヒドロインドール）
威いｔよ１．２．３．４−テトラヒドロキノリ７９４体
とジ゛ケテンとを反応させることを特徴とする一般弐Ｏ
ｕ）； （式中、ｎば１′！！たは２を表す。）で表されるギノ
キザリノン誘導体の製造法。 （３）次式ＱＩＩ）； ｃ式中、ｎは１ま九は２を表す。） で表されるキノキザリノン誘導体を、還元または低級ア
ルキル化またはハロゲン化するととｆｔ！＋！ｆ徴とす
る一般式（Ｖ）：（式中、Ｒは水素原子、低級アルキル
基、ハロゲン原子またはトリフルオロメチル基ヲ表し、
ｎは１または２を表す。） で表さ−れるキノキザリノ／誘導体の製造法。 （４） 一般式 （■）： （０）□ （式中、Ｒは水素原子、低級アルキル基、・・ロゲン原
子またはトリフルオロメチル基を表し５口は１またＴｆ
ｉ２を９ｍは０または１全表す。） で表されるキノキザリノン誘導体の１種また、は２種以
上全有効成分として含有することを特徴とする農園芸用
殺菌剤。[Scope of Claims] (1) General formula (1); (wherein, R represents a hydrogen atom, a lower argyl group, a halogen atom, or 11fluoromethyl A4', n is 1 or 2, 9m is 0 or 1) Quinoxalino/derivative represented by. (2) Indoline (2,5-dihydroindole) represented by the following formula (old; (in the formula, n represents 1 or 2)
General 2 O characterized by reacting 1.2.3.4-tetrahydroquinol 794 and diketene
u); (In the formula, n represents 1'!! or 2.) A method for producing a gynoxalinone derivative. (3) Following formula QII); In formula c, n represents 1 or 2. ) When the quinoxalinone derivative represented by is reduced, lower alkylated or halogenated, ft! +! General formula (V) having the f-character: (wherein R represents a hydrogen atom, a lower alkyl group, a halogen atom or a trifluoromethyl group,
n represents 1 or 2. ) A method for producing a quinoxalino/derivative represented by: (4) General formula (■): (0)□ (In the formula, R represents a hydrogen atom, a lower alkyl group, a rogen atom, or a trifluoromethyl group, and 5 points are 1 or Tf
9m for i2 represents all 0 or 1. An agricultural and horticultural fungicide characterized by containing one or more of the following quinoxalinone derivatives as total active ingredients.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19274683A JPS6084287A (en) | 1983-10-14 | 1983-10-14 | Quinoxalinone derivative, its preparation and fungicide for agricultural and horticultural use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19274683A JPS6084287A (en) | 1983-10-14 | 1983-10-14 | Quinoxalinone derivative, its preparation and fungicide for agricultural and horticultural use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6084287A true JPS6084287A (en) | 1985-05-13 |
Family
ID=16296362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19274683A Pending JPS6084287A (en) | 1983-10-14 | 1983-10-14 | Quinoxalinone derivative, its preparation and fungicide for agricultural and horticultural use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6084287A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009532423A (en) * | 2006-04-06 | 2009-09-10 | グラクソ グループ リミテッド | Pyrrolo-quinoxalinone derivatives as antibacterial agents |
-
1983
- 1983-10-14 JP JP19274683A patent/JPS6084287A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009532423A (en) * | 2006-04-06 | 2009-09-10 | グラクソ グループ リミテッド | Pyrrolo-quinoxalinone derivatives as antibacterial agents |
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