JPH0116805B2 - - Google Patents
Info
- Publication number
- JPH0116805B2 JPH0116805B2 JP60281140A JP28114085A JPH0116805B2 JP H0116805 B2 JPH0116805 B2 JP H0116805B2 JP 60281140 A JP60281140 A JP 60281140A JP 28114085 A JP28114085 A JP 28114085A JP H0116805 B2 JPH0116805 B2 JP H0116805B2
- Authority
- JP
- Japan
- Prior art keywords
- control agent
- rice
- catechins
- leaf blight
- crop disease
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- Agricultural Chemicals And Associated Chemicals (AREA)
Description
［産業上の利用分野］
本発明は作物病害防除剤に関し、詳しくはイネ
いもち病やイネごま葉枯病等に対して有効な防除
剤に関する。
［従来の技術および発明が解決しようとする問題
点］
イネいもち病およびイネごま葉枯病は重要な農
作物病害である。従来、これら病害の防除には有
機合成殺菌剤、抗生物質剤などが使用されていた
が、最近これら薬剤に対する耐性菌の発生が認め
られ、薬剤防除の効率が低下する傾向にある。
この耐性菌の発生も回避するためには、従来の
防除剤とは構造が異なり、作用機構が相違する薬
剤を組合せて使用することが必要である。このよ
うな理由から、作用機構の異なる新規な病害防除
剤の開発が望まれている。
一方、農薬の環境汚染あるいは農薬の残留問題
に対する社会的関心は高く、この面からは環境中
において生物分解性の高い天然物起源の農薬の出
現が強く期待されている。
［問題点を解決するための手段］
本発明者らは上記の要求を満足する新規な作物
病害防除剤を開発すべく研究を重ねた。その過程
で、茶葉に多量に含まれるカテキン類の生理活性
について検討し、茶葉より抽出、分離した４種の
カテキン、すなわち（−）―エピカテキン（以
下、ECと略記する。）、（−）―エピガロカテキン
（以下、EGCと略記する。）、（−）―エピカテキ
ンガレート（以下、ECGと略記する。）および
（−）―エピガロカテキンガレート（以下、
EGCGと略記する。）の水酸基をすべてメチル化
したメチル化カテキン類がいずれもイネいもち病
菌、イネごま葉枯病菌に対して顕著な生育抑制効
果を示すことを見出し、かかる知見に基いて本発
明を完成するに至つた。
すなわち本発明は、メチル化カテキン類を有効
成分とする作物病害防除剤である。
本発明に用いるメチル化カテキン類は上記の
EC，EGC，ECGおよびEGCGの水酸基のすべて
をメチル化した化合物であり、以下の式で表わさ
れる。
上記式［］〜［］で表わされるメチル化カ
テキン類は単独で用いてもよく、２種以上を組合
せて用いてもよい。
茶葉からカテキン類を抽出、分離するには既知
の手法を適用すればよく、たとえば特公昭56−
38591号公報に記載された方法などにより行なう
ことができる。１例を示すと、茶葉を熱水もしく
は酢酸エチル等の有効溶媒を用いて抽出したの
ち、セフアデツクスLH20あるいはODSなどを利
用した液体クロマトグラフイーにより分離、精製
することができる。
このようにして分離したカテキン類をメチル化
する方法としては、たとえば箱守法（J.
Biochem.，55，205（1964））に準拠して行なうこ
とができる。すなわち、カテキン類（EG，
EGC，ECG，EGCG）をそれぞれ約50倍量のジ
メチルスルホキシドに溶解し、これに計算量より
過剰の水素化ナトリウムとヨウ化メチルを加え、
40℃にて１時間撹拌を続けた後、生成物をベンゼ
ンで抽出し、水で数回洗浄したのち、溶媒を除去
することにより目的とするメチル化物を得る。メ
チル化カテキン類の精製は各種クロマトグラフイ
ーなどにより行なうことができる。
合成されたメチル化カテキン類は、マススペク
トロメトリー（EI法、直接導入）によつて確認
を行なうことができ、それぞれの化合物の主要な
マスフラグメントは以下の通りである。
EC―Ｍ：ｍ／ｚ（相対強度）360（28，M+），209
（14），195(12)，194（100），179（15），
151(6)
EGC―Ｍ：ｍ／z390（31，M+），358(5)，224
（100），209（48），181(10)，151(4)
ECG―Ｍ：ｍ／z540（２，M+），356(11)，342
（24），329（20），328（100），195（90），
151(11)
EGCG―Ｍ：ｍ／z570（３，M+），372（20），359
（22），358（100），343（15），327（14），
195（58）
メチル化カテキン類の抗菌活性については、イ
ネいもち病菌に対してはECG―Ｍ，EGCG―Ｍが
EC―Ｍ，EGC―Ｍに比較して強く、イネごま葉
枯病菌に対しては逆にEC―ＭやEGC―Ｍの方が
抗菌活性が強い傾向が認められる。作物病害防除
剤として使用する際のこれら有効成分の濃度は対
象作物などを考慮して決定すればよいが、通常は
300〜1000ppmの範囲で使用する。また、メチル
化カテキン類は使用目的を考慮して適当に製剤す
ることができ、そのために既知の補助成分を任意
に用いることができる。たとえば、鉱物質粉末な
どの固体担体、増量剤や有機溶媒などの液体希釈
剤、乳化剤、分散助剤等を用いて常法にしたがつ
て粉剤、水和剤、粒剤、乳剤等に製剤することが
できる。
［発明の効果］
本発明で使用する有効成分はイネいもち病，イ
ネごま葉枯病等の病原菌に対して抗菌活性を有す
るばかりでなく、有機リン殺菌剤であるIBP（チ
オリン酸ｏ，ｏ―ジイソプロピルＳ―ベンジル）
に対して中度の耐性を示すイネいもち病菌Ｃ―13
などに対しても抗菌力を持つなど既知の殺菌剤と
は異なる病害防除作用を有している。
しかも、この有効成分は長年にわたつて人類が
飲料として利用してきた茶葉中に多量に含まれる
天然成分を起源としているため、毒性、環境汚染
等の面から人畜に及ぼす影響が少なく、実用性の
高いものである。
［実施例］
次に、本発明を実施例により詳しく説明する。
試験例
メチル化カテキン類の所定量を含有する寒天培
地にイネいもち病菌（P.oryzae）またはイネご
ま葉枯病（C.miyabeanus）を接種し、27℃でイ
ネいもち病菌では７日間、イネごま葉枯病菌では
４日間培養したときの生育状況を観察した。結果
を第１表および第２表に示す。なお、参考のため
メチル化カテキン類の代りにカテキン類を使用し
た場合の結果も示す。
[Industrial Application Field] The present invention relates to a crop disease control agent, and more particularly to a control agent effective against rice blast, rice sesame leaf blight, and the like. [Prior art and problems to be solved by the invention] Rice blast disease and rice sesame leaf blight are important agricultural crop diseases. Conventionally, organic synthetic fungicides, antibiotics, and the like have been used to control these diseases, but recently the emergence of bacteria resistant to these drugs has been observed, and the efficiency of drug control tends to decrease. In order to avoid the development of resistant bacteria, it is necessary to use a combination of drugs that have different structures and mechanisms of action from conventional control agents. For these reasons, the development of new disease control agents with different mechanisms of action is desired. On the other hand, there is a high level of social concern about the environmental pollution caused by pesticides and the problem of pesticide residues, and from this perspective, there are strong expectations for the emergence of pesticides derived from natural products that are highly biodegradable in the environment. [Means for Solving the Problems] The present inventors have conducted extensive research to develop a novel crop disease control agent that satisfies the above requirements. In the process, we investigated the physiological activities of catechins, which are abundant in tea leaves, and extracted and separated four types of catechins from tea leaves: (-)-epicatechin (hereinafter abbreviated as EC), (-)- -Epigallocatechin (hereinafter abbreviated as EGC), (-)-epicatechin gallate (hereinafter abbreviated as ECG), and (-)-epigallocatechin gallate (hereinafter abbreviated as ECG).
Abbreviated as EGCG. It was discovered that methylated catechins in which all the hydroxyl groups of Ivy. That is, the present invention is a crop disease control agent containing methylated catechins as an active ingredient. The methylated catechins used in the present invention are those listed above.
It is a compound in which all of the hydroxyl groups of EC, EGC, ECG, and EGCG are methylated, and is represented by the following formula. The methylated catechins represented by the above formulas [] to [] may be used alone or in combination of two or more. To extract and separate catechins from tea leaves, known methods can be applied; for example,
This can be carried out by the method described in Japanese Patent No. 38591. For example, tea leaves can be extracted using hot water or an effective solvent such as ethyl acetate, and then separated and purified by liquid chromatography using Sephadex LH20 or ODS. For example, the Hakomori method (J.
Biochem., 55 , 205 (1964)). That is, catechins (EG,
EGC, ECG, EGCG) were each dissolved in about 50 times the volume of dimethyl sulfoxide, and to this was added sodium hydride and methyl iodide in excess of the calculated amount.
After continued stirring at 40° C. for 1 hour, the product was extracted with benzene, washed several times with water, and the solvent was removed to obtain the desired methylated product. Methylated catechins can be purified by various chromatography methods. The synthesized methylated catechins can be confirmed by mass spectrometry (EI method, direct introduction), and the main mass fragments of each compound are as follows. EC-M: m/z (relative intensity) 360 (28, M + ), 209
(14), 195(12), 194(100), 179(15),
151(6) EGC-M: m/z390 (31, M + ), 358(5), 224
(100), 209 (48), 181 (10), 151 (4) ECG-M: m/z540 (2, M + ), 356 (11), 342
(24), 329 (20), 328 (100), 195 (90),
151(11) EGCG-M: m/z570 (3, M + ), 372 (20), 359
(22), 358 (100), 343 (15), 327 (14),
195(58) Regarding the antibacterial activity of methylated catechins, ECG-M and EGCG-M are effective against rice blast fungi.
It is stronger than EC-M and EGC-M, and conversely, EC-M and EGC-M tend to have stronger antibacterial activity against the rice sesame leaf blight fungus. The concentration of these active ingredients when used as a crop disease control agent can be determined by considering the target crop, etc., but usually
Use in the range of 300-1000ppm. In addition, methylated catechins can be appropriately formulated in consideration of the purpose of use, and known auxiliary ingredients can be optionally used for this purpose. For example, it is formulated into powders, wettable powders, granules, emulsions, etc. using a solid carrier such as mineral powder, a liquid diluent such as a filler or an organic solvent, an emulsifier, a dispersion aid, etc. in a conventional manner. be able to. [Effects of the Invention] The active ingredient used in the present invention not only has antibacterial activity against pathogenic bacteria such as rice blast and rice sesame leaf blight, but also has antibacterial activity against pathogenic bacteria such as rice blast and rice sesame leaf blight. diisopropyl S-benzyl)
The rice blast fungus C-13 shows moderate resistance to
It also has antibacterial activity against other germs, which is different from known fungicides. Moreover, since this active ingredient originates from natural ingredients contained in large amounts in tea leaves, which have been used as a beverage by humans for many years, it has little impact on humans and livestock in terms of toxicity and environmental pollution, and is of practical use. It's expensive. [Examples] Next, the present invention will be explained in detail by examples. Test example Rice blast fungus (P.oryzae) or rice sesame leaf blight (C.miyabeanus) is inoculated onto an agar medium containing a predetermined amount of methylated catechins. The growth status of the leaf blight fungus was observed after culturing for 4 days. The results are shown in Tables 1 and 2. For reference, results obtained when catechins were used instead of methylated catechins are also shown.
【表】【table】
【表】
表から明らかなように、カテキン類では上記病
原菌に対しほとんど生育阻害が認められないが、
メチル化カテキン類では著しい生育阻害が認めら
れた。しかも、メチル化カテキン類はイネいもち
病防除に使用されている有機リン殺菌剤IBPに対
して中度の耐性を示す耐性菌Ｃ―13に対しても強
い阻害効果を発揮する。
実施例
メチル化カテキン類の代表とてEGC―Ｍを用
いて下記の処方により乳剤と水和剤を調製した。
乳 剤
有効成分（EGC―Ｍ） 30％
有機溶媒（トルエン） 55％
乳化剤（ツイーン80） 15％
水和剤
有効成分（EGC―Ｍ） 10％
カオリン 85％
界面活性剤 ５％
（エマゾール1130：1.67％
エマルゲン106：3.33％）
上記薬剤の希釈液をイネ苗（３〜５葉期）に噴
霧し、風乾後常法によりイネいもち病菌またはイ
ネごま葉枯病菌の胞子を噴霧接種してこれらの病
菌を感染させ、EGC―Ｍのイネいもち病菌およ
びイネごま葉枯病菌に対する防除効果を調べた。
すなわち、病原菌を感染させてイネいもち病菌で
は７日後、イネごま葉枯病菌では４日後にイネ苗
を対照区たる薬剤無処理のイネ苗と病斑数を比較
し、防除価を病斑数の減少率（％）として求め
た。結果を第３表に示す。[Table] As is clear from the table, catechins hardly inhibit the growth of the above pathogenic bacteria.
Significant growth inhibition was observed with methylated catechins. Furthermore, methylated catechins also exert a strong inhibitory effect on C-13, a resistant bacterium that is moderately resistant to the organophosphorus fungicide IBP used to control rice blast. Example Emulsions and wettable powders were prepared using EGC-M as a representative of methylated catechins according to the following formulations. Emulsion active ingredient (EGC-M) 30% Organic solvent (toluene) 55% Emulsifier (Tween 80) 15% Wettable powder active ingredient (EGC-M) 10% Kaolin 85% Surfactant 5% (Emazol 1130: 1.67 % Emulgen 106: 3.33%) A diluted solution of the above drug was sprayed on rice seedlings (3-5 leaf stage), and after air-drying, spores of rice blast fungus or rice sesame leaf blight fungus were sprayed and inoculated using the usual method to eliminate these pathogens. was infected, and the control effect of EGC-M against rice blast fungus and rice sesame leaf blight fungus was investigated.
In other words, after 7 days for the rice blast fungus and 4 days for the rice sesame leaf blight fungus after infecting the rice seedlings with the pathogen, the number of lesions was compared with that of the rice seedlings that were not treated with the chemical as a control, and the control value was calculated based on the number of lesions. It was calculated as a reduction rate (%). The results are shown in Table 3.
Claims (1)
物の少くとも１種のメチル化カテキン類を有効成
分とする作物病害防除剤。 ２ 作物病害防除剤がイネいもち病防除剤または
イネごま葉枯病防除剤である特許請求の範囲第１
項記載の作物病害防除剤。 ３ 作物病害防除剤がイネいもち病防除剤または
イネごま葉枯病防除剤である特許請求の範囲第１
項記載の作物病害防除剤。[Scope of Claims] 1. A crop disease control agent containing at least one methylated catechin compound represented by the following formulas [] to [] as an active ingredient. 2 Claim 1 in which the crop disease control agent is a rice blast control agent or a rice sesame leaf blight control agent
The crop disease control agent described in Section 1. 3 Claim 1 in which the crop disease control agent is a rice blast control agent or a rice sesame leaf blight control agent
The crop disease control agent described in Section 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60281140A JPS62142102A (en) | 1985-12-16 | 1985-12-16 | Blight controlling agent for crop |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60281140A JPS62142102A (en) | 1985-12-16 | 1985-12-16 | Blight controlling agent for crop |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62142102A JPS62142102A (en) | 1987-06-25 |
| JPH0116805B2 true JPH0116805B2 (en) | 1989-03-27 |
Family
ID=17634920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60281140A Granted JPS62142102A (en) | 1985-12-16 | 1985-12-16 | Blight controlling agent for crop |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62142102A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01272615A (en) * | 1988-04-25 | 1989-10-31 | Matsushita Electric Works Ltd | Production of solid melamine resin |
| JPH03195716A (en) * | 1989-12-25 | 1991-08-27 | Matsushita Electric Works Ltd | Production of melamine resin |
| JP2005272337A (en) * | 2004-03-24 | 2005-10-06 | Kao Corp | Exterminator composition against arthropod or mollusc |
| JP7817749B2 (en) * | 2023-07-07 | 2026-02-19 | 国立大学法人 筑波大学 | Plant growth promoter and method for growing grasses |
-
1985
- 1985-12-16 JP JP60281140A patent/JPS62142102A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62142102A (en) | 1987-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |