JPS604164A - Cyanodithioacetate derivative and agricultural and horticultural fungicide - Google Patents
Cyanodithioacetate derivative and agricultural and horticultural fungicideInfo
- Publication number
- JPS604164A JPS604164A JP11104083A JP11104083A JPS604164A JP S604164 A JPS604164 A JP S604164A JP 11104083 A JP11104083 A JP 11104083A JP 11104083 A JP11104083 A JP 11104083A JP S604164 A JPS604164 A JP S604164A
- Authority
- JP
- Japan
- Prior art keywords
- group
- cyanodithioacetate
- agricultural
- compound
- horticultural fungicide
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は下記一般式を有するシアノジチオアセテート誘
導体及び該化合物を有効成分とする農園芸用殺菌剤に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a cyanodithioacetate derivative having the following general formula and an agricultural and horticultural fungicide containing the compound as an active ingredient.
水素又は塩素原子、R2はアルキル基(オキソ基を含ん
でも良い)、ベンジル基、アルキルカルバモイル基(環
化したアルキル基を含んでも良い)、アルキリル基、ア
ルコキシカルボニル基又はジエトキシチオフオスフオリ
ル基を表わす。)上記一般式にて表わされる化合物につ
いて代表的なものを表−1に例示する。尚、化合物の表
示は上記一般式に於けるR、、FL2の置換基にて表わ
す、また、物性の欄の”NMRは核磁気共鳴スペクトル
、括弧内は溶媒を示し、表示法は慣用の方法に従つた□
J Itは赤外線吸収スペクトル、括弧内は測定法を示
(7、主紫なヒータの波数のみを表示した。Hydrogen or chlorine atom, R2 is an alkyl group (which may contain an oxo group), a benzyl group, an alkylcarbamoyl group (which may contain a cyclized alkyl group), an alkyl group, an alkoxycarbonyl group, or a diethoxythiophosphoryl group. represents a group. ) Representative examples of the compounds represented by the above general formula are shown in Table 1. In addition, the display of the compound is expressed by the substituents R, FL2 in the above general formula, and in the column of physical properties, "NMR" indicates the nuclear magnetic resonance spectrum, and the number in parentheses indicates the solvent, and the display method is the conventional method. I followed□
J It is an infrared absorption spectrum, and the measurement method is shown in parentheses (7, only the wave number of the main purple heater is shown.
本発明の化合物を得るには、例えば、メチル−2−(f
fi換フェニル)−2−シアノジチオアセテートとイン
シアナート、酸クロリド、クロロホルメート、カルバモ
イルクロリド、ジエチルチオリン酸クロリド等の目的と
する化合物に対応する反応試薬を、例えば、エタノール
、テトラヒドロフラン、ベンゼン等の適当な溶媒中で、
必要に応じて、例えば、トリエチルアミン、ナトリウム
アルコラード、炭酸カリウム等の適当な塩基の存在下に
)室温又は加温下に1時間〜数日反応させる方法等によ
り合成することができる。To obtain the compounds of the invention, for example, methyl-2-(f
A reaction reagent corresponding to the desired compound such as fi-substituted phenyl)-2-cyanodithioacetate and incyanate, acid chloride, chloroformate, carbamoyl chloride, diethylthiophosphoric acid chloride, etc., is mixed with an appropriate reaction agent such as ethanol, tetrahydrofuran, benzene, etc. in a solvent,
If necessary, it can be synthesized by a method of reacting for one hour to several days at room temperature or with heating (in the presence of an appropriate base such as triethylamine, sodium alcoholade, potassium carbonate, etc.).
以下に代表的な合成例を示し更に具体的に説明する。Typical synthesis examples will be shown below and explained in more detail.
合成例
S−(パラクロロ−2−シアノ−1−メチルチオ)スチ
リル(N−メチル)チオカーバメートの合成。Synthesis Example S-Synthesis of (parachloro-2-cyano-1-methylthio)styryl (N-methyl)thiocarbamate.
メチル 2−(パラクロロフェニル)−2−シアノジチ
オアセテ−)3.6gをシクロヘキサン及びベンゼンに
とかし、メチルイソシアネート10gトリエチルアミン
3滴加え、室温にて4日放置する。溶媒をデカントし、
析出し′九結晶を集め、ベンゼンにて洗い、目的物の透
明結晶を3g得る。Dissolve 3.6 g of methyl 2-(parachlorophenyl)-2-cyanodithioacetate in cyclohexane and benzene, add 10 g of methyl isocyanate and 3 drops of triethylamine, and let stand at room temperature for 4 days. Decant the solvent and
The nine precipitated crystals were collected and washed with benzene to obtain 3 g of transparent crystals of the desired product.
本発明化合物は広汎な農園芸作物の病害の防除に効果的
であり、その主なものを例示すれば以下のものが挙げら
れる。The compounds of the present invention are effective in controlling a wide range of diseases of agricultural and horticultural crops, and the main ones include the following.
水稲 いもぢ病、ごま葉枯病;豆類 褐斑病;果樹 り
んご 黒星、モニリア病、うどんと病;かんきつ 黒点
、そうか病;梨 赤星、黒星病;桃 細葉、黒星、灰星
病;茶 炭そ、もち、綱もち病;柿 炭そ、落葉、うど
んと病;野菜 きゅうり べと、炭素、黒星、灰色かび
、うどんと病、つる割病;とまと 疫、葉かび、灰色か
び病;大根 萎黄病;ビート 褐斑病;ジャガ芋 疫病
;メロン 炭そ、つる枯病等。Paddy rice: potato leaf blight, sesame leaf blight; beans: brown spot; fruit trees: apples: black spot, monilia disease, powdery mildew; citrus: black spot, scab; pear: red star, scab; peach: thin leaf, black star, scab; brown Anthrax, mochi, rope blast; persimmon anthracnose, defoliation, powdery mildew; vegetables cucumber downy mildew, carbon, black star, gray mold, powdery mildew, vine warp; tomato blight, leaf mold, gray mold; radish Yellow blight; beet brown spot; potato late blight; melon anthracnose, vine blight, etc.
散布量については必ずしも制限はないが、通常は作物の
生育する圃場に散布する場合には有効成分化合物(A、
1.)として50〜1000V■Oaまた、土壌中に施
用する場合には2〜8 kgA、 1./10a 程度
が適当である。勿論、これは一つの目安であり、作物の
種類、病害の種類及び被害の程度、時期、天候、薬剤の
剤型等の要因を考慮して必要に応じて適宜加減される。There are no restrictions on the amount of spraying, but when spraying on fields where crops are grown, the amount of active ingredient compounds (A,
1. ) as 50 to 1000V Oa, and 2 to 8 kgA when applied to soil; 1. /10a is appropriate. Of course, this is just a guideline, and it may be adjusted as necessary, taking into account factors such as the type of crop, the type and degree of damage, the season, the weather, and the dosage form of the drug.
本発明の化合物は前述のごとく農園芸用殺菌剤として用
いられるが、そのまま或いは担体(希釈剤)と混合して
粉剤、粒剤、水和剤、乳剤、油剤串
その他農薬製剤上慣用されている適宜な剤として用いら
れる。この場合、必要に応じて展着剤、乳化剤、湿展剤
、固着剤等が適宜用いられ、又、他の殺菌剤や殺虫剤、
除草剤、肥相等と併用、混合することもできる。As mentioned above, the compound of the present invention is used as a fungicide for agriculture and horticulture, but it is also commonly used as it is or mixed with a carrier (diluent) in powders, granules, wettable powders, emulsions, oil skewers, and other agrochemical preparations. It is used as an appropriate agent. In this case, spreading agents, emulsifiers, wetting agents, fixing agents, etc. are used as appropriate, and other fungicides, insecticides,
It can also be used or mixed with herbicides, fertilizers, etc.
実施例1 粉剤
有効成分として表中の化合物 3部
クレー 40部
タルク 57部
実施例2 水和剤
表中化合物 75部
ポリオキシエチレンアルキルアリルエーテル 9部ホワ
イトカーボン 16部
以下、本発明化合物の効果を具体的に説明するため、代
表的な試験例を示す。但し、これらは単なる例示であり
、本発明の適用例はこれらのみに限られないことは言う
までもない。Example 1 Powder Compounds listed in the table as active ingredients: 3 parts Clay 40 parts Talc 57 parts Example 2 Wettable powder Compounds listed in the table 75 parts Polyoxyethylene alkyl allyl ether 9 parts White carbon 16 parts Below, the effects of the compounds of the present invention were evaluated. For concrete explanation, typical test examples are shown. However, these are merely examples, and it goes without saying that the application examples of the present invention are not limited to these.
試験例1 稲いもち病効力試験
〈方法〉
鉢植えの稲(品種:土石)の3葉期に、所定濃度の薬液
の2001J/102相当量を噴霧散布する。風乾後に
培養した稲いもち病菌(Pyricularia or
yzae)の分生胞子を顕微鏡100倍1視野当り40
個になるように調整した懸濁液を噴霧接種した。Test Example 1 Rice Blast Efficacy Test <Method> An amount equivalent to 2001J/102 of a predetermined concentration of a chemical solution is sprayed onto potted rice plants (variety: Doishi) at the 3-leaf stage. Rice blast fungus (Pyricularia or
yzae) conidia at 40 per field of view under a microscope at 100x magnification.
The suspension was prepared by spray inoculation.
接種後直ちに、温度23°C1湿度100%の暗黒条件
下に48時間保った後に温室内に放置し、接種10日後
に以下の規準で発病程度を調べ、発病度を算定した。但
し連数は3連とする。Immediately after inoculation, the plants were kept under dark conditions at a temperature of 23° C. and 100% humidity for 48 hours, and then left in a greenhouse. Ten days after inoculation, the degree of disease onset was determined using the following criteria. However, the number of runs shall be three.
f:発病程度側指数
N:調査葉数
発病程度別指数 1葉当り病斑数
00
1
2 2〜5
3 6〜10
4 11へ
試験例2 太根萎黄病効力試験
〈方法〉
大根参賀病菌(Fusariurn oxysqoru
m 1. raptlani)の厚膜胞子により人工的
に汚染させた土壌を直径15Crnの素焼鉢につめる。f: Index of disease severity N: Number of investigated leaves Number of lesions per leaf 00 1 2 2-5 3 6-10 4 To 11 Test Example 2 Efficacy test for thick root yellowing disease <Method> Radish Sanga fungus ( Fusariurn oxysqoru
m1. Clay pots with a diameter of 15 Crn are filled with soil artificially contaminated with chlamydospores of A. raptlani.
表面にあらかじめ発芽させた大根の種子(品種:青首宮
重)を針当10粒播種し汚染土で覆土する。直ちに、所
定の濃度に希釈した薬液を表面に均一に潅注した後に、
軽く潅水する。その後、鉢を温室内に放置し、適宜潅水
する。10 seeds of radish (variety: Aokubi Miyaju) that have been germinated in advance are sown on the surface, and the soil is covered with contaminated soil. Immediately, after uniformly irrigating the surface with a chemical solution diluted to a predetermined concentration,
Water lightly. The pots are then left in the greenhouse and watered accordingly.
処理60日後に発病の有無・程度を以下の基準に従がい
調査する。60 days after treatment, the presence/absence and severity of disease onset is investigated according to the following criteria.
但し、連数は5連
試験例3 かんきつ黒点病効力試験
〈方法〉
鉢植えのみかん(品種:夏柑)の新芽の展開時に、所定
濃度に希釈した薬液を充分量噴霧散布し後に温室内で風
乾した。みかん枯枝で培養したDiaportbe c
itriの分生胞子を噴霧接種した後直ちに、温度Z3
’C,湿度100%の暗黒下に2日間保った。2日後
に温室内に放置し、接種30日後に発病程度を調査した
。However, the number of rows is 5.Test Example 3 Citrus black spot efficacy test <Method> When the new shoots of potted mandarin oranges (variety: Natsukan) develop, a sufficient amount of the chemical solution diluted to the specified concentration is sprayed and then air-dried in a greenhouse. did. Diaportbe c cultured on mandarin orange branches
Immediately after spray inoculation with conidia of T. itri, temperature Z3
'C, kept in darkness with 100% humidity for 2 days. Two days later, the plants were left in a greenhouse, and the degree of disease onset was investigated 30 days after inoculation.
但し、連数け3連とする。However, the number of runs shall be three.
n:発病程度別葉数
N:調査船葉数
0
1 1〜3
2 4〜6
3 7〜10
4 月〜
く結果〉
試験例4 カンキツ黒点病菌に対する胞子発芽阻止試験
く方法〉
カンキツ枯枝に培養したDiaporthe citr
iの分生胞子と薬液を混合し、顕微鏡100倍l視野当
り約20個になるように調整する。n: Number of leaves by severity of disease N: Number of leaves investigated 0 1 1-3 2 4-6 3 7-10 April Results> Test Example 4 Method for spore germination inhibition test against citrus black spot fungus> On citrus dead branches Cultured Diaporthe citr
Mix the conidia of conidia i and the drug solution, and adjust to about 20 conidia per 1 field of view of a 100x microscope.
スライドグラス上に、この混合懸濁液を0.02 m1
滴下し、温度27°C1湿度100チに20時間保った
後に、検顕して胞子発芽の有無を調査する。Place 0.02 ml of this mixed suspension on a slide glass.
After dropping the solution and keeping it at a temperature of 27° C. and a humidity of 100° C. for 20 hours, it is examined for spore germination by microscopic examination.
いずれも2反覆とし、約200個の胞子の発芽の有無・
程度を調べる。Both were repeated twice, and the presence or absence of germination of approximately 200 spores was determined.
Check the degree.
〈結果〉<result>
Claims (1)
含んでも良い)、ベンジル基、アルキルカルバモイル基
(環化したアルキル基を含んでも良い)、アルキリル基
、アルコキシカルボニル基又はジエトキシチオフォスフ
ォリル基を表わす。)にて表わされるシアノジチオアセ
テート誘導体。 は水素又は塩素原子、几、はアルキル基(オキソ基を含
んでも良い)、ベンジル基、アルキ−ルカルバモイル基
(環化したアルキル基を含んでも良い)、アルキリル基
、アルコキシカルボニル基又はジエトキシチオフオスフ
オリル基を表わす。)にて表わされるシアノジチオアセ
テート誘導体を有効成分とする農園芸用殺菌剤。[Claims] is a hydrogen or chlorine atom, d: an alkyl group (which may include an oxo group), a benzyl group, an alkylcarbamoyl group (which may include a cyclized alkyl group), an alkyl group, an alkoxycarbonyl group. or diethoxythiophosphoryl group. ) Cyanodithioacetate derivative represented by. is a hydrogen or chlorine atom, 几 is an alkyl group (which may contain an oxo group), a benzyl group, an alkylcarbamoyl group (which may contain a cyclized alkyl group), an alkyl group, an alkoxycarbonyl group, or a diethoxythiophyl group Represents an osphoryl group. ) An agricultural and horticultural fungicide containing a cyanodithioacetate derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11104083A JPS604164A (en) | 1983-06-22 | 1983-06-22 | Cyanodithioacetate derivative and agricultural and horticultural fungicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11104083A JPS604164A (en) | 1983-06-22 | 1983-06-22 | Cyanodithioacetate derivative and agricultural and horticultural fungicide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS604164A true JPS604164A (en) | 1985-01-10 |
JPH04978B2 JPH04978B2 (en) | 1992-01-09 |
Family
ID=14550878
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11104083A Granted JPS604164A (en) | 1983-06-22 | 1983-06-22 | Cyanodithioacetate derivative and agricultural and horticultural fungicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS604164A (en) |
-
1983
- 1983-06-22 JP JP11104083A patent/JPS604164A/en active Granted
Non-Patent Citations (1)
Title |
---|
JOURNAL OF CHEMICAL SOCIETY PERKIN TRANS 1=1978 * |
Also Published As
Publication number | Publication date |
---|---|
JPH04978B2 (en) | 1992-01-09 |
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