JPS6016435B2 - Coumarin derivatives and agricultural and horticultural fungicides containing coumarin derivatives - Google Patents
Coumarin derivatives and agricultural and horticultural fungicides containing coumarin derivativesInfo
- Publication number
- JPS6016435B2 JPS6016435B2 JP15147776A JP15147776A JPS6016435B2 JP S6016435 B2 JPS6016435 B2 JP S6016435B2 JP 15147776 A JP15147776 A JP 15147776A JP 15147776 A JP15147776 A JP 15147776A JP S6016435 B2 JPS6016435 B2 JP S6016435B2
- Authority
- JP
- Japan
- Prior art keywords
- coumarin derivatives
- parts
- agricultural
- horticultural fungicides
- fungicides containing
- 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
Links
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrane Compounds (AREA)
Description
【発明の詳細な説明】 本発明は新規なクマリン誘導体に関する。[Detailed description of the invention] The present invention relates to novel coumarin derivatives.
更に具体的には本発明は下記一般式（式中Ｘは低級アル
キル基を示しそしてｎは１又は２の整数を示す）で表わ
されるクマリン誘導体及び該クマリン誘導体を含有する
農園芸用殺菌剤に関する。More specifically, the present invention relates to a coumarin derivative represented by the following general formula (wherein X represents a lower alkyl group and n represents an integer of 1 or 2) and an agricultural and horticultural fungicide containing the coumarin derivative. .
本発明にかかるクマＩＪン誘導体は文献未戦の新規な化
合物であり、農園芸用殺菌剤、殊にキュウリ等のうどん
こ病防除用薬剤として極めて有用なものである。The Kuman IJ derivative according to the present invention is a novel compound that has not yet been published in the literature, and is extremely useful as a fungicide for agricultural and horticultural purposes, particularly for controlling powdery mildew on cucumbers and the like.
これらの誘導体は４−ヒドロキシー３一（Ｎ−モノまた
はジアルキル置換フェニル−チオカルバモィル）クマリ
ンと総称できる。本発明のクマリン誘導体は次の反応式
に示す方法により容易に製造することができる。反応式
（式中×及びｎの定義は前記と同意義を示す）前記クマ
リン議導体の製造の一例（一般式においてＸ＝３一Ｃ比
およびｎ＝１の場合）を次に示す。These derivatives can be collectively referred to as 4-hydroxy-3-(N-mono- or dialkyl-substituted phenyl-thiocarbamoyl)coumarins. The coumarin derivative of the present invention can be easily produced by the method shown in the following reaction formula. An example of the production of the coumarin conductor (in the general formula, when X=31C ratio and n=1) is shown below.
４ーヒドロキシクマリン３．５夕およびｍートリルイソ
チオシアナート３．５夕をジメチルホルムアミド２０の
上に溶解させ、トリェチルアミン３滴を添加し、８０〜
９０ｏｏで１即時間加熱蝿拝した。3.5 mm of 4-hydroxycoumarin and 3.5 mm of m-tolyl isothiocyanate are dissolved over 20 mm of dimethylformamide, 3 drops of triethylamine are added, and 80 ~
I heated it for 1 hour at 90oo.
次に反応液を放冷後、少量の水を添加して希釈し析出物
を炉取し、次いでエタノールで洗浄後ジメチルホルムア
ミドと水との混合溶媒により再結晶し所望の生成物を黄
色微粒状晶４．５夕として得た。融点１１９〜１２００
０。この化合物の質量スペクトルデータは次のとおりで
ある。Next, the reaction solution was left to cool, diluted with a small amount of water, and the precipitate was collected in a furnace. After washing with ethanol, the desired product was recrystallized with a mixed solvent of dimethylformamide and water to form yellow fine particles. Obtained as crystal 4.5 yen. Melting point 119-1200
0. The mass spectral data of this compound is as follows.
前記製造例に従って製造されるクマリン誘導体の代表例
は次のとおりである。Representative examples of coumarin derivatives produced according to the above production examples are as follows.
第１表
次に本発明のクマリン誘導体の有用性を試験例をもって
説明する。Table 1 Next, the usefulness of the coumarin derivative of the present invention will be explained using test examples.
試験例
キュウリのウドンコ病防除効果試験
士耕ポット栽培したキュウリ（品種 相模半白）の第一
藁期苗に所定濃度の供試薬液を１０叫づつ散布して一夜
放置後うどんこ病菌胞子懸濁液をスプレーガンを用いて
圧力ｌｋ９／肌で贋霧接種した。Test Example Powdery Mildew Control Effect on Cucumber Tester A test chemical solution of a prescribed concentration was sprayed 10 times at a time on the first straw stage seedlings of cucumbers (variety: Sagami Hanshiro) grown in pots, and after being left overnight, powdery mildew spores were suspended. The solution was inoculated using a spray gun at a pressure of lk9/skin.
接種１０日後に薬剤散布葉の病斑面積歩合（％）を調査
し、無散布区との対比で防除価（％）を算出した。なお
本試験は１区３蓮制で行つた。その試験結果は次の表の
とおりである。Ten days after inoculation, the lesion area ratio (%) on the chemically sprayed leaves was investigated, and the control value (%) was calculated in comparison with the non-sprayed area. This test was conducted using a 1-ward, 3-lot system. The test results are shown in the table below.
尚比較薬剤はＳ，Ｓ−６ーメチルキノキサリン−２，３
ージイルージチオカーボネ−ト（商品名モレスタン）を
使用した。The comparative drug is S,S-6-methylquinoxaline-2,3
-diyldithiocarbonate (trade name Molestane) was used.
本発明のクマリン誘導体を農園芸用殺菌剤として使用す
る場合は粉剤、水和剤、乳剤、粒剤、微粒剤およびその
他の一般に行なわれる形態の薬剤として使用することが
可能である。When the coumarin derivative of the present invention is used as a fungicide for agriculture and horticulture, it can be used as a powder, wettable powder, emulsion, granule, fine granule, or other commonly used forms.
本発明において使用される担体は固体または液体のいず
れでも良く、また特定の担体に限定されるものではない
。固体担体としては例えば種々の粘土類、カオリン、ク
レー、けいそう土、タルク、シリカ等が挙げられ、液体
挺体としては本発明に係る有効成分化合物に対して溶媒
となるものおよび非溶媒であっても補助剤により容易に
本発明の有効成分化合物を分散または溶解し得るものな
らば使用できる。例えばベンゼン、キシレン、トルヱン
、ケロシン、アルコール類、ケトン類、ジメチルスルホ
オキサィド、ジメチルホルムアミド等が挙げられる。こ
れに適当な界面活性剤、その他の補助剤例えば展着剤、
固着剤等を混合し、水溶性あるいは乳剤として使用でき
る。また本発明にかかる有効成分化合物は省力化および
防除効果を確実にするためにその他の殺菌剤、殺虫剤、
除草剤、植物生長調節剤などと混合して使用することも
可能である。次に本発明の製剤例を若干示すが、主要化
合物および添加物は本実施例に限定されるものではない
。The carrier used in the present invention may be either solid or liquid, and is not limited to a specific carrier. Examples of the solid carrier include various clays, kaolin, clay, diatomaceous earth, talc, silica, etc., and examples of the liquid carrier include those that serve as a solvent and non-solvent for the active ingredient compound according to the present invention. Any material can be used as long as it can easily disperse or dissolve the active ingredient compound of the present invention with an adjuvant. Examples include benzene, xylene, toluene, kerosene, alcohols, ketones, dimethyl sulfoxide, and dimethylformamide. Suitable surfactants and other auxiliary agents such as spreading agents,
It can be mixed with a fixing agent and used as a water-soluble or emulsion. In addition, the active ingredient compound according to the present invention may be used in combination with other fungicides, insecticides, etc. to ensure labor-saving and pest control effects.
It can also be used in combination with herbicides, plant growth regulators, etc. Next, some formulation examples of the present invention will be shown, but the main compounds and additives are not limited to these examples.
製剤例 １
（粉剤）
４ーヒドロキシ−３−（Ｎ−３−メチルフエニルーチオ
カルバモィル）クマリン〔前記化合物Ｍ．｛１’に相当
）２部およびクレー９８部を均一に混合粉砕すれば有効
成分２％を含有する粉剤を得る。Formulation Example 1 (Powder) 4-Hydroxy-3-(N-3-methylphenylthiocarbamoyl)coumarin [the above compound M. By uniformly mixing and pulverizing 2 parts {corresponding to 1') and 98 parts of clay, a powder containing 2% of the active ingredient is obtained.
このものを使用する場合は１０アール当り１回に１〜６
ｋ９をそのまま徹粉機にて植物に散布する。製剤例 ２
（水和剤）
前記化合物Ｍ．（１｝３礎部、リグニンスルホン酸カル
シウム２部、アルキルベンゼンスルホン酸カルシウム３
部、ポリオキシェチレンノニルフェニルェーテル５部お
よび白土６の部を均一に混合して微細に粉砕し、均一組
成の微粉末状の有効成分３０％を含有した水和剤を得る
。When using this product, 1 to 6 times per 10 ares.
Spray K9 directly onto the plants using a powder filter. Formulation example 2
(Wettable powder) The compound M. (1) 3 parts of the base, 2 parts of calcium lignin sulfonate, 3 parts of calcium alkylbenzenesulfonate
1 part, 5 parts of polyoxyethylene nonyl phenyl ether, and 6 parts of clay are uniformly mixed and finely ground to obtain a wettable powder containing 30% of the active ingredient in the form of a fine powder with a uniform composition.
このものを使用する場合は水で１０００〜４００の音‘
こ希釈して植物に散布する。製剤例 ３（乳剤）
前記化合物船．【１１３の都、ポリオキシェチレンノニ
ルフェニルェ−テル１７部およびキシレン５３部を混合
して溶解すれば有効成分３０％を含有する乳剤を得る。When using this product, make a sound of 1000 to 400 with water.
Dilute this and spray on plants. Formulation Example 3 (Emulsion) The above compound vessel. By mixing and dissolving 17 parts of polyoxyethylene nonyl phenyl ether and 53 parts of xylene, an emulsion containing 30% of the active ingredient is obtained.
このものを使用する場合は水で希釈して６００〜１００
針昔溶液にして植物に散布する。製剤例 ４（粒剤）
前記化合物Ｍ．【１１５部、ラウリルサルフェート１．
５部、リグニンスルホン酸カルシウム１．５部、ベント
ナィト２５部および白土６７部に水１５部を加えて混練
機で混練した後造粒機にて造粒し、流動乾燥機で乾燥す
ると５％粒剤が得られる。When using this product, dilute it with water to give a concentration of 600 to 100.
Make a needle solution and spray it on plants. Formulation Example 4 (Granules) The compound M. [115 parts, lauryl sulfate 1.
5 parts of calcium ligninsulfonate, 1.5 parts of calcium ligninsulfonate, 25 parts of bentonite, and 67 parts of clay were mixed with 15 parts of water in a kneader, then granulated in a granulator, and dried in a fluidized dryer to obtain 5% grains. agent is obtained.
Claims (1)
の整数を示す）で表わされるクマリン誘導体。 ２ 一般式 ▲数式、化学式、表等があります▼ （但し式中Ｘは低級アルキル基を示しそしてｎは１又
は２の整数を示す）で表わされるクマリン誘導体を有効
成分としてなることを特徴とする農園芸用殺菌剤。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (However, X represents a lower alkyl group and n is 1 or 2
Coumarin derivative represented by (integer of ). 2. It is characterized by containing a coumarin derivative represented by the general formula ▲ mathematical formula, chemical formula, table, etc. ▼ (wherein X represents a lower alkyl group and n represents an integer of 1 or 2) as an active ingredient. Fungicide for agriculture and horticulture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15147776A JPS6016435B2 (en) | 1976-12-18 | 1976-12-18 | Coumarin derivatives and agricultural and horticultural fungicides containing coumarin derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15147776A JPS6016435B2 (en) | 1976-12-18 | 1976-12-18 | Coumarin derivatives and agricultural and horticultural fungicides containing coumarin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5377065A JPS5377065A (en) | 1978-07-08 |
| JPS6016435B2 true JPS6016435B2 (en) | 1985-04-25 |
Family
ID=15519354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15147776A Expired JPS6016435B2 (en) | 1976-12-18 | 1976-12-18 | Coumarin derivatives and agricultural and horticultural fungicides containing coumarin derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6016435B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0022961D0 (en) * | 2000-09-19 | 2000-11-01 | Zeneca Ltd | Fungicidal coumarin derivatives |
-
1976
- 1976-12-18 JP JP15147776A patent/JPS6016435B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5377065A (en) | 1978-07-08 |
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