JPH064592B2 - Pyrazolcarboxamide compound and fungicide containing the same as an active ingredient - Google Patents
Pyrazolcarboxamide compound and fungicide containing the same as an active ingredientInfo
- Publication number
- JPH064592B2 JPH064592B2 JP12194785A JP12194785A JPH064592B2 JP H064592 B2 JPH064592 B2 JP H064592B2 JP 12194785 A JP12194785 A JP 12194785A JP 12194785 A JP12194785 A JP 12194785A JP H064592 B2 JPH064592 B2 JP H064592B2
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- Prior art keywords
- compound
- dimethylindan
- parts
- active ingredient
- present
- 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.)
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Description
【発明の詳細な説明】 本発明は、一般式〔Ｉ〕 〔式中、Ｒは水素原子、ハロゲン原子またはメチル基を
表わす。〕 で示されるピラゾールカルボキサミド化合物 （以下本発明化合物と記す）およびそれを有効成分とす
る殺菌剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention has the general formula [I] [In the formula, R represents a hydrogen atom, a halogen atom or a methyl group. ] It is related with the pyrazole carboxamide compound (it is hereafter described as this invention compound) shown by these, and the bactericidal agent which makes it an active ingredient.
本発明者らは、ピラゾールカルボキサミド化合物につい
て鋭意検討を重ねた結果、上記一般式〔Ｉ〕で示される
本発明化合物が、多くの植物病原菌特に担子菌類に属す
る微生物に対して予防的、治療的あるいは浸透移行殺菌
効力を有することを見出し、本発明を完成させた。The present inventors have conducted extensive studies on pyrazole carboxamide compounds, and as a result, the compounds of the present invention represented by the above general formula [I] are prophylactically, therapeutically or against various plant pathogenic bacteria, particularly microorganisms belonging to basidiomycetes. The present invention has been completed by finding out that it has an osmotic transfer bactericidal effect.
本発明化合物が優れた効力を有する植物病害としては、
例えばイネの紋枯病(Rhizoctonia solani)、擬似紋枯病
(Rhizoctonia oryzae,Rhizoctonia solani IIIＢ型）、
ムギ類のさび病(Puccinia striiformis,P.graminis,P.r
econdita,P.hordei)、雪腐病(Typhula incarnata,T.ish
ikariensis)、裸黒穂病(Ustilago tritici,U.nuda)、ナ
シの赤星病(Gymnosporangium haraenum)、各種作物の立
枯病(Rhizoctonia solani)、白絹病(Corticium rolfsi
i)、ジャガイモ、ビートのリゾクトニア病(Rhizoctonia
solani)、牧草、芝生等の葉腐病(Rhizoctonia solan
i)、白絹病(Corticium rolfsii)、葉さび病(Uromyces t
rifolii)、雪腐病(Typhula incarnata,T.ishikariensi
s)などが挙げられる。As a plant disease for which the compound of the present invention has excellent efficacy,
For example, rice blight (Rhizoctonia solani), pseudo-blight blight
(Rhizoctonia oryzae, Rhizoctonia solani IIIB type),
Rust of wheat (Puccinia striiformis, P. graminis, Pr
econdita, P.hordei), Snow rot (Typhula incarnata, T.ish
ikariensis), naked smut (Ustilago tritici, U.nuda), pear scab (Gymnosporangium haraenum), wilt of various crops (Rhizoctonia solani), white silkworm (Corticium rolfsi)
i), potato, beet Rhizoctonia
leaf rot (Rhizoctonia solan)
i), White silkworm (Corticium rolfsii), Leaf rust (Uromyces t)
rifolii), snow rot (Typhula incarnata, T. ishikariensi
s) and the like.
従って、本発明化合物は水田、畑地、果樹園、牧草地、
芝生地等の殺菌剤の有効成分として用いることができ
る。Therefore, the compound of the present invention is used in paddy fields, upland fields, orchards, meadows,
It can be used as an active ingredient of a bactericide such as lawn.
本発明化合物としては次のようなものが挙げられる。Examples of the compound of the present invention include the following.
Ｎ−（１，１−ジメチルインダン−４−イル）−１，３
−ジメチルピラゾール−４−カルボキサミド Ｎ−（１，１−ジメチルインダン−４−イル）−１，
３，５−トリメチルピラゾール−４−カルボキサミド Ｎ−（１，１−ジメチルインダン−４−イル）−５−フ
ルオロ−１，３−ジメチルピラゾール−４−カルボキサ
ミド Ｎ−（１，１−ジメチルインダン−４−イル）−５−ク
ロロ−１，３−ジメチルピラゾール−４−カルボキサミ
ド Ｎ−（１，１−ジメチルインダン−４−イル）−５−ブ
ロモ−１，３−ジメチルピラゾール−４−カルボキサミ
ド Ｎ−（１，１−ジメチルインダン−４−イル）−５−ヨ
ード−１，３−ジメチルピラゾール−４−カルボキサミ
ド 本発明化合物は、例えば下記に示す方法により製造する
ことができる。N- (1,1-dimethylindan-4-yl) -1,3
-Dimethylpyrazole-4-carboxamide N- (1,1-dimethylindan-4-yl) -1,
3,5-Trimethylpyrazole-4-carboxamide N- (1,1-dimethylindan-4-yl) -5-fluoro-1,3-dimethylpyrazole-4-carboxamide N- (1,1-dimethylindan-4 -Yl) -5-chloro-1,3-dimethylpyrazole-4-carboxamide N- (1,1-dimethylindan-4-yl) -5-bromo-1,3-dimethylpyrazole-4-carboxamide N- ( 1,1-Dimethylindan-4-yl) -5-iodo-1,3-dimethylpyrazole-4-carboxamide The compound of the present invention can be produced, for example, by the method shown below.
〔式中、Ａｒは を表わす。〕 即ち、まずアセチルアセトンを１，１−ジメチルインダ
ン−４−イルイソシアネートと反応させて、３−（１，
１−ジメチルインダン−４−イルカルバモイル）ペンタ
ン−２，４−ジオンを得、これにメチルヒドラジンを反
応させることにより、上記の本発明化合物を得る方法。 [In the formula, Ar is Represents That is, first, acetylacetone is reacted with 1,1-dimethylindan-4-ylisocyanate to give 3- (1,
A method for obtaining the above-mentioned compound of the present invention by obtaining 1-dimethylindan-4-ylcarbamoyl) pentane-2,4-dione and reacting this with methylhydrazine.
〔式中、Ａｒは前記と同一の意味を表わす。〕即ち、ま
ず１，３−ジメチルピラゾリン−５−オンを１，１−ジ
メチルインダン−４−イルイソシアネートと反応させ
て、１，３−ジメチル−５−オキソ−Ｎ−（１，１−ジ
メチルインダン−４−イル）−４，５−ジヒドロピラゾ
ール−４−カルボキサミドを得、これにオキシ塩化リン
を反応させることにより、上記の塩素置換ピラゾールカ
ルボキサミド化合物を得、該化合物を例えばパラジウム
−炭素などを触媒として接触還元するか、該化合物にフ
ッ化カリウム、フッ化セシウムなどのフッ素化剤を作用
させる通常の塩素／フッ素交換反応により上記の本発明
化合物を得る方法。 [In the formula, Ar represents the same meaning as described above. That is, first, 1,3-dimethylpyrazolin-5-one is reacted with 1,1-dimethylindan-4-ylisocyanate to prepare 1,3-dimethyl-5-oxo-N- (1,1-dimethyl Indan-4-yl) -4,5-dihydropyrazole-4-carboxamide, which is reacted with phosphorus oxychloride to obtain the above-mentioned chlorine-substituted pyrazolecarboxamide compound. A method for obtaining the above-mentioned compound of the present invention by catalytic reduction as a catalyst or by an ordinary chlorine / fluorine exchange reaction in which a fluorinating agent such as potassium fluoride or cesium fluoride is allowed to act on the compound.
次に本発明化合物の製造法につき参考例で詳しく説明す
る。Next, the production method of the compound of the present invention will be described in detail in reference examples.
参考例１ アセチルアセトン６００mg（６．０mmol）および１，１
−ジメチルインダン−４−イルイソシアネート１．１２
ｇ（６．０mmol）のトルエン１０ml溶液に、攪拌下室温
でトリエチルアミン７３０mg（７．２mmol）を滴加し、
さらに室温で１２時間攪拌した後、反応溶液を減圧下に
濃縮し、粗３−（１，１−ジメチルインダン−４−イル
カルバモイル）ペンタン−２，４−ジオンを得た。次
に、得られた粗３−（１，１−ジメチルインダン−４−
イルカルバモイル）ペンタン−２，４−ジオンをエタノ
ール１０mlに溶かし、その溶液にメチルヒドラジン２７
６mg（６．０mmol）を加え、６時間室温で攪拌し、さら
に１時間加熱還流下に攪拌した。放冷後、溶媒を減圧留
去し、残渣をメタノールで再結晶して、Ｎ−（１，１−
ジメチルインダン−４−イル）−１，３−トリメチルピ
ラゾール−４−カルボキサミド１．２５ｇを得た。Reference Example 1 600 mg (6.0 mmol) of acetylacetone and 1,1
-Dimethylindan-4-yl isocyanate 1.12
730 mg (7.2 mmol) of triethylamine was added dropwise to a 10 ml solution of g (6.0 mmol) in toluene at room temperature with stirring.
After further stirring at room temperature for 12 hours, the reaction solution was concentrated under reduced pressure to obtain crude 3- (1,1-dimethylindan-4-ylcarbamoyl) pentane-2,4-dione. Then, the obtained crude 3- (1,1-dimethylindan-4-
Ilcarbamoyl) pentane-2,4-dione was dissolved in 10 ml of ethanol, and the solution was mixed with methylhydrazine 27
6 mg (6.0 mmol) was added, and the mixture was stirred for 6 hours at room temperature, and further stirred for 1 hour while heating under reflux. After allowing to cool, the solvent was evaporated under reduced pressure, the residue was recrystallized from methanol, and N- (1,1-
1.25 g of dimethylindan-4-yl) -1,3-trimethylpyrazole-4-carboxamide was obtained.
ｍｐ １５１．６℃ 参考例２ １，３−ジメチルピラゾリン−５−オン１．１２ｇ（１
０mmol）を、トリエチルアミン１．１１ｇを含むトルエ
ン１０mlに懸濁させ、そこへ１，１−ジメチルインダン
−４−イルイソシアネート１．８７ｇのトルエン２ml溶
液を、攪拌下室温で滴加し、さらに室温で１２時間攪拌
した。その後、その反応混合物を水で３回抽出し、水層
を濃塩酸で酸性にして氷冷し、生成した沈澱をろ取し、
風乾することによって、１，３−ジメチル−５−オキソ
−Ｎ−（１，１−ジメチルインダン−４−イル）−４，
５−ジヒドロピラゾール−４−カルボキサミド１．８１
ｇ（mp１４１．４℃）を得た。次に、オキシ塩化リン５
mlおよびＮ，Ｎ−ジエチルアニリン９０７mgの混合物に
得られた１，３−ジメチル−５−オキソ−Ｎ−（１，１
−ジメチルインダン−４−イル）−４，５−ジヒドロピ
ラゾール−４−カルボキサミドを加え、その混合物を
１．５時間、加熱還流下に攪拌した。得られた反応混合
物を氷水に注入し、クロロホルムで３回抽出し、クロロ
ホルム層を水洗し無水硫酸、マグネシウムで乾燥した
後、溶媒を減圧留去し、残渣をエタノールで再結晶して
Ｎ−（１，１−ジメチルインダン−４−イル）−５−ク
ロロ−１，３−ジメチルピラゾール−４−カルボキサミ
ド0.96ｇを得た。mp 151.6 ° C. Reference Example 2 1,3-Dimethylpyrazolin-5-one 1.12 g (1
0 mmol) was suspended in 10 ml of toluene containing 1.11 g of triethylamine, and a solution of 1.87 g of 1,1-dimethylindan-4-ylisocyanate in 2 ml of toluene was added dropwise thereto at room temperature with stirring, and further at room temperature. It was stirred for 12 hours. Then, the reaction mixture was extracted three times with water, the aqueous layer was acidified with concentrated hydrochloric acid and ice-cooled, and the formed precipitate was collected by filtration.
By air-drying, 1,3-dimethyl-5-oxo-N- (1,1-dimethylindan-4-yl) -4,
5-dihydropyrazole-4-carboxamide 1.81
g (mp 141.4 ° C.) were obtained. Next, phosphorus oxychloride 5
ml of 1,3-dimethyl-5-oxo-N- (1,1 obtained in a mixture of ml and 907 mg of N, N-diethylaniline.
-Dimethylindan-4-yl) -4,5-dihydropyrazole-4-carboxamide was added and the mixture was stirred for 1.5 hours with heating under reflux. The obtained reaction mixture was poured into ice water, extracted three times with chloroform, the chloroform layer was washed with water and dried over anhydrous sulfuric acid and magnesium, the solvent was evaporated under reduced pressure, and the residue was recrystallized with ethanol to give N- ( 0.96 g of 1,1-dimethylindan-4-yl) -5-chloro-1,3-dimethylpyrazole-4-carboxamide was obtained.
mp １７５．２℃ 参考例３ 参考例２で得られたＮ−（１，１−ジメチルインダン−
４−イル）−５−クロロ−１，３−ジメチルピラゾール
−４−カルボキサミド２７０mgをエタノール６mlに溶か
し、無水酢酸ナトリウム１５０mgの存在下、Pd/c(5%)４
０mgを触媒として用いて、接触還元を行なった。反応
後、触媒および沈澱物をセライトろ過し、溶媒を減圧留
去した後、残渣をシリカゲルカラムクロマトグラフィー
に処しＮ−（１，１−ジメチルインダン−４−イル）−
１，３−ジメチルピラゾール−４−カルボキサミド１５
６mgを得た。mp 175.2 ° C. Reference Example 3 N- (1,1-dimethylindane-obtained in Reference Example 2
4-yl) -5-chloro-1,3-dimethylpyrazole-4-carboxamide (270 mg) was dissolved in ethanol (6 ml), and Pd / c (5%) 4 was added in the presence of anhydrous sodium acetate (150 mg).
Catalytic reduction was carried out using 0 mg as catalyst. After the reaction, the catalyst and the precipitate were filtered through Celite, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain N- (1,1-dimethylindan-4-yl)-.
1,3-Dimethylpyrazole-4-carboxamide 15
6 mg was obtained.
mp １４６．８℃ 参考例４ フッ化カリウム粉末１．０ｇ、スルホラン15mlおよびト
ルエン２０mlを反応容器に入れ、加熱還流させながら、
モレキラーシーブスで系内の水分を除去した後トルエン
を留去し冷却した。次いで、これに、参考例２で得られ
たＮ−（１，１−ジメチルインダン−４−イル）−５−
クロロ−１，３−ジメチルピラゾール−４−カルボキサ
ミド３１８mgを加えて、窒素雰囲気下、１８０〜２００
℃で１６時間加熱した。冷却後、反応液に水およびエー
テルを加えて分液し水層をエーテル抽出し、エーテル層
を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し
た後、溶媒を留去し、残渣をシリカゲルカラムクロマト
グラフィーに処し、５−フルオロ−１，３−ジメチル−
Ｎ−（１，１−ジメチルインダン−４−イル）−ピラゾ
ール−４−カルボキサミド１４０mgを得た。mp 146.8 ° C. Reference Example 4 Potassium fluoride powder (1.0 g), sulfolane (15 ml) and toluene (20 ml) were placed in a reaction vessel and heated under reflux.
After removing water in the system with molecular sieves, toluene was distilled off and the system was cooled. Then, to this was added N- (1,1-dimethylindan-4-yl) -5-obtained in Reference Example 2.
Chloro-1,3-dimethylpyrazole-4-carboxamide (318 mg) was added, and the mixture was heated to 180-200 under a nitrogen atmosphere.
Heat at 16 ° C. for 16 hours. After cooling, water and ether were added to the reaction solution for partitioning, the aqueous layer was extracted with ether, the ether layer was washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by a silica gel column. Subjected to chromatography, 5-fluoro-1,3-dimethyl-
140 mg of N- (1,1-dimethylindan-4-yl) -pyrazole-4-carboxamide was obtained.
mp １３８．５℃１９ Ｆ−ＮＭＲスペクトル 測定溶媒：ＣＤＣｌ３ 外部標準：ＣＦ３ＣＯ２Ｈ ４８ppm（ＣＦ３ＣＯ２Ｈに対し、高磁場側） このような製造法によって製造できる本発明化合物を第
１表に示す。mp 138.5 ° C. 19 F-NMR spectrum Measurement solvent: CDCl 3 External standard: CF 3 CO 2 H 48 ppm (high magnetic field side relative to CF 3 CO 2 H) The compound of the present invention which can be produced by such a production method is The results are shown in Table 1.
本発明化合物を殺菌剤の有効成分として用いる場合は、
他の何らの成分も加えずそのまま用いてもよいが、通常
は、固体担体、液体担体、界面活性剤その他の製剤用補
助剤と混合して、乳剤、水和剤、懸濁剤、粒剤、粉剤、
液剤等に製剤して用いる。 When the compound of the present invention is used as an active ingredient of a bactericide,
Although it may be used as it is without adding any other component, it is usually mixed with a solid carrier, a liquid carrier, a surfactant or other auxiliary agents for formulation to prepare an emulsion, a wettable powder, a suspension, a granule. , Powder,
Used as a liquid formulation.
これらの製剤中の有効成分として本発明化合物の含量
は、重量比で１．０〜９５％、好ましくは２．０〜８
０．０％である。The content of the compound of the present invention as an active ingredient in these preparations is 1.0 to 95% by weight, preferably 2.0 to 8%.
It is 0.0%.
上述の固体担体としては、カオリンクレー、アッタパル
ジャイトクレー、ベントナイト、酸性白土、パイロフィ
ライト、タルク、珪藻土、方解石、トウモロコシ穂軸
粉、クルミ殻粉、尿素、硫酸アンモニウム、合成含水酸
化珪素等の微粉末あるいは粒状物が挙げられ、液体担体
としては、キレシン、メチルナフタレン等の芳香族炭化
水素、イソプロパノール、エチレングリコール、セロソ
ルブ等のアルコール、アセトン、シクロヘキサノン、イ
ソホロン等のケトン、大豆油、綿実油等の植物油、ジメ
チルスルホキシド、アセトニトリル、水等が挙げられ
る。乳化、分散、湿展等のために用いられる界面活性剤
としては、アルキル硫酸エステル塩、アルキル（アリー
ル）スルホン酸塩、ジアルキルスルホコハク酸塩、ポリ
オキシエチレンアルキルアリールエーテルリン酸エステ
ル塩、ナフタレンスルホン酸ホルマリン縮合物等の陰イ
オン界面活性剤、ポリオキシエチレンアルキルエーテ
ル、ポリオキシエチレンポリオキシプロピレンブロック
コポリマー、ソルビタン脂肪酸エステル、ポリオキシエ
チレンソルビタン脂肪酸エステル等の非イオン界面活性
剤等が挙げられる。製剤用補助剤としては、リグニンス
ルホン酸塩、アルギン酸塩、ポリビニルアルコール、ア
ラビアガム、ＣＭＣ（カルボキシメチルセルロース）、
ＰＡＰ（酸性リン酸イソプロピル）等が挙げられる。Examples of the solid carrier include kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic silicon oxide hydroxide. Examples of the liquid carrier include powders or granules.Clecine, aromatic hydrocarbons such as methylnaphthalene, alcohols such as isopropanol, ethylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil. , Dimethyl sulfoxide, acetonitrile, water and the like. Surfactants used for emulsification, dispersion, wet extension, etc. include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate ester salts, naphthalene sulfonic acid. Examples thereof include anionic surfactants such as formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, nonionic surfactants such as sorbitan fatty acid esters and polyoxyethylene sorbitan fatty acid esters. As a formulation auxiliary agent, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose),
PAP (acidic isopropyl phosphate) etc. are mentioned.
次に製剤例を示す。なお、本発明化合物は第１表の化合
物番号で示す。部は重量部を表わす。Formulation examples are shown below. The compounds of the present invention are shown by the compound numbers in Table 1. Parts represent parts by weight.
製剤例１ 本発明化合物(1)〜(4)５０部、リグニンスルホン酸カル
シウム３部、ラウリル硫酸ナトリウム２部および合成含
水酸化珪素４５部をよく粉砕混合して水和物を得る。Formulation Example 1 50 parts of the present compounds (1) to (4), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain a hydrate.
製剤例２ 本発明化合物(1)〜(4)１０部、ポリオキシエチレンスチ
リルフェニルエーテル１４部、ドデシルベンゼンスルホ
ン酸カルシウム６部およびキシレン７０部をよく混合し
て乳剤を得る。Formulation Example 2 Emulsions are obtained by thoroughly mixing 10 parts of the compounds (1) to (4) of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzene sulfonate and 70 parts of xylene.
製剤例３ 本発明化合物(2)２部、合成含水酸化珪素１部、リグニ
ンスルホン酸カルシウム２部、ベントナイト３０部およ
びカオリンクレー６５部をよく粉砕混合し、水を加えて
よく練り合せた後、造粒乾燥して粒剤を得る。Formulation Example 3 2 parts of the compound (2) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay were well pulverized and mixed, and after adding water and kneading well, Granulate and dry to obtain granules.
製剤例４ 本発明化合物(1)２５部、ポリオキシエチレンソルビタ
ンモノオレエート３部、ＣＭＣ３部および水６９部を混
合し、有効成分の粒度が５ミクロン以下になるまで湿式
粉砕して懸濁剤を得る。Formulation Example 4 25 parts of the compound (1) of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water are mixed and wet pulverized until the particle size of the active ingredient becomes 5 microns or less, and a suspension agent. To get
製剤例５ 本発明化合物(2)２部、カオリンクレー８８部およびタ
ルク１０部をよく粉砕混合して粉剤を得る。Formulation Example 5 2 parts of the compound (2) of the present invention, 88 parts of kaolin clay and 10 parts of talc are well pulverized and mixed to obtain a powder.
製剤例６ 本発明化合物(3)１０部、ポリオキシエチレンスチリル
フェニルエーテル１部および水８９部を混合し、液剤を
得る。Formulation Example 6 10 parts of the compound (3) of the present invention, 1 part of polyoxyethylene styryl phenyl ether and 89 parts of water are mixed to obtain a liquid preparation.
これらの製剤は、そのままであるいは水で希釈して、茎
葉散布するか、土壤に散粉、散粒して混和するか、ある
いは土壤施用する等の種々の形態で使用する。また、他
の殺菌剤と混合して用いることにより、殺菌効力の増強
を期待できる。さらに、殺虫剤、殺ダニ剤、殺線虫剤、
除草剤、植物生長調節剤、肥料、土壤改良剤と混合して
用いることもできる。These preparations are used as they are or after diluted with water, and are applied in various forms such as foliage spraying, powdering and mixing in soil, mixing, or application in soil. In addition, it is expected to enhance the bactericidal effect by mixing with other bactericides. In addition, insecticides, acaricides, nematicides,
It can also be used as a mixture with a herbicide, a plant growth regulator, a fertilizer, and a soil improvement agent.
本発明化合物を殺菌剤の有効成分として用いる場合、そ
の施用量は通常１アールあたり１〜１００ｇであり、乳
剤、水和剤、懸濁剤、液剤等を水で希釈して施用する場
合、その施用濃度は０．００５〜０．５％であり、粒
剤、粉剤等はなんら希釈することなくそのまま施用す
る。When the compound of the present invention is used as an active ingredient of a bactericide, its application amount is usually 1 to 100 g per are, and when an emulsion, a wettable powder, a suspending agent, a liquid agent or the like is diluted with water and applied, The application concentration is 0.005 to 0.5%, and granules, powders and the like are applied as they are without any dilution.
次に、本発明化合物が殺菌剤の有効成分として有用であ
ることを試験例で示す。なお、本発明化合物は第１表の
化合物番号で示し、比較対照に用いた化合物は第２表の
化合物記号で示す。Next, it is shown in Test Examples that the compound of the present invention is useful as an active ingredient of a bactericide. The compounds of the present invention are shown by the compound numbers in Table 1, and the compounds used for comparison and control are shown by the compound symbols in Table 2.
また防除効力は、調査時の供試植物の発病状態すなわち
葉、茎等の菌叢、病班の程度を肉眼観察し、菌叢、病班
が全く認められなければ「５」、１０％程度認められれ
ば「４」、３０％程度認められれば「３」、５０％程度
認められれば「２」、７０％程度認められれば「１」、
それ以上で化合物を供試していない場合の発病状態と差
が認められなければ「０」として、６段階に評価し、そ
れぞれ５、４、３、２、１、０、で示す。 The control efficacy is "5", 10% if the disease state of the test plant at the time of the survey, that is, the flora of leaves, stems, etc. If it is recognized, "4", if 30% is recognized, "3", if 50% is recognized, "2", if 70% is recognized, "1",
If there is no difference from the onset state when the compound is not tested further, it is evaluated as "0" on a scale of 6 and shown as 5, 4, 3, 2, 1, 0, respectively.
試験例１ イネ紋枯病予防効果試験 プラスチックポットに砂壤土を詰め、イネ（近畿３３
号）を播種し、湿温内で８週間育成した。６〜７葉が展
開したイネに、製剤例２に準じて乳剤にした供試化合物
を水で希釈して所定濃度にし、それを葉面に充分付着す
るように茎葉散布した。散布後イネ紋枯病菌の含菌寒天
片を貼付接種した。接種後２８℃、多湿下で４日間育成
し、防除効力を調査した。その結果を第３表に示す。Test Example 1 Prevention of rice blight blight Disease A plastic pot is filled with sandstone, and rice (Kinki 33
No.) was sowed and grown in a humid temperature for 8 weeks. To the rice having 6 to 7 leaves developed, the test compound emulsified according to Formulation Example 2 was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface. After spraying, agar-containing agar pieces of rice wilt fungus were applied and inoculated. After inoculation, the plant was grown at 28 ° C. under high humidity for 4 days, and the control efficacy was investigated. The results are shown in Table 3.
試験例２ イネ紋枯病残効効果試験 プラスチックポットに砂壤土を詰め、イネ（近畿３３
号）を播種し、温室内で８週間育成した。６〜７葉が展
開したイネに、製剤例１に準じて水和剤にした供試化合
物を水で希釈して所定濃度にし、それを葉面に充分付着
するように茎葉散布した。散布後７日間温室内で育成し
イネ紋枯病菌の含菌寒天片を貼付接種した。接種後２８
℃、多湿下で４日間育成し、防除効力を調査した。その
結果を第４表に示す。 Test Example 2 Rice scab blight residual effect effect test A plastic pot was filled with sandstone soil, and rice (Kinki 33
No.) was sowed and grown in a greenhouse for 8 weeks. To the rice with 6 to 7 leaves spread, the test compound made into a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface. After spraying, the plant was grown in a greenhouse for 7 days, and agar-containing agar pieces of rice wilt fungus were applied and inoculated. 28 after vaccination
It was grown for 4 days at ℃ and high humidity, and the control effect was investigated. The results are shown in Table 4.
試験例３ イネ紋枯病浸透移行効果試験 １３０ml容のプラスチックポットに砂壤土を詰め、イネ
（近畿３３号）を播種し、温室内で８週間育成した。６
〜７葉が展開したイネに、製剤例２に準じて乳剤にした
供試化合物を水で希釈し、その所定量を土壤に灌注し
た。灌注後７日間温室内で育成し、イネ紋枯病菌の含菌
寒天片を貼付接種した。接種後２８℃、多湿下で４日間
育成し、防除効力を調査した。その結果を第５表に示
す。 Test Example 3 Permeation transfer effect test of rice blight blight The sand pot was filled in a plastic pot of 130 ml, and rice (Kinki No. 33) was sown and grown in a greenhouse for 8 weeks. 6
To the rice with ~ 7 leaves spread, the test compound, which was made into an emulsion according to Formulation Example 2, was diluted with water, and a predetermined amount thereof was irrigated into the soil. After irrigation, the plants were grown in a greenhouse for 7 days, and agar-containing agar pieces of rice wilt disease bacteria were applied and inoculated. After inoculation, the plant was grown at 28 ° C. under high humidity for 4 days, and the control efficacy was investigated. The results are shown in Table 5.
試験例４ コムギ赤さび病治療効果試験 プラスチックポットに砂壤土を詰め、コムギ（農林７３
号）を播種し、温室内で１０日間育成した。第２〜３葉
が展開したコムギの幼苗に、コムギ赤さび病菌を散粉接
種した。接種後２３℃、多湿下で１日育成し、製剤例１
に準じて水和剤にした供試化合物を水で希釈して所定濃
度にし、それを葉面に充分付着するように茎葉散布し
た。散布後２３℃照明下で７日間育成し、防除効力を調
査した。その結果を第６表に示す。 Test Example 4 Wheat leaf rust therapeutic effect test A plastic pot was filled with sandstone soil, and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 10 days. The wheat seedlings on which the second to third leaves were developed were inoculated with the wheat leaf rust fungus by dusting. After inoculation, it was grown at 23 ° C. in high humidity for 1 day, and then Preparation Example 1
The test compound, which was made into a wettable powder according to the above, was diluted with water to a predetermined concentration, and the foliage was sprayed so that it adhered sufficiently to the leaf surface. After spraying, the seedlings were grown for 7 days under illumination at 23 ° C., and the control efficacy was investigated. The results are shown in Table 6.
試験例５ インゲン白絹病予防効果試験 ２５０ml容プラスチックポットにあらかじめふすま培地
で培養した白絹病原菌を砂壤土とよく混合しを詰めた。
その上にインゲン（大正金時）を播種した。製剤例１に
準じて水和剤にした供試化合物を水で希釈し、その所定
量を土壤に灌注した。灌注後３週間温室内で育成し、地
際部の茎の発病程度により防除効力を調査した。その結
果を第７表に示す。 Test Example 5 Test for Preventing White Silkworm Disease in White Beans A 250 ml plastic pot was filled with sand silk soil in which white silk pathogens previously cultivated in a bran medium were well mixed.
Beans (Taisho Kintoki) were sown on it. The test compound, which was made into a wettable powder according to Formulation Example 1, was diluted with water, and a predetermined amount thereof was irrigated into the soil. After the irrigation, the plants were grown in a greenhouse for 3 weeks, and the control efficacy was investigated by the degree of disease on the stems at the edge. The results are shown in Table 7.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 松尾 憲忠 兵庫県宝塚市高司４丁目２番１号 住友化 学工業株式会社内 (72)発明者 前田 清人 兵庫県宝塚市高司４丁目２番１号 住友化 学工業株式会社内 (72)発明者 井上 悟 兵庫県宝塚市高司４丁目２番１号 住友化 学工業株式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kenzo Matsuo 4-2-1 Takashi Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Kiyoto Maeda 4-2-1 Takashi Takarazuka-shi, Hyogo No. Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Satoru Inoue 4-2-1 Takashi Takarazuka, Hyogo Prefecture Sumitomo Kagaku Kogyo Co., Ltd.
Claims (2)
表わす。〕 で示されるピラゾールカルボキサミド化合物。1. A general formula [In the formula, R represents a hydrogen atom, a halogen atom or a methyl group. ] The pyrazole carboxamide compound shown by these.
表わす。〕 で示されるピラゾールカルボキサミド化合物を有効成分
とすることを特徴とする殺菌剤。2. General formula [In the formula, R represents a hydrogen atom, a halogen atom or a methyl group. ] A fungicide characterized by comprising a pyrazole carboxamide compound represented by the following as an active ingredient.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12194785A JPH064592B2 (en) | 1985-06-05 | 1985-06-05 | Pyrazolcarboxamide compound and fungicide containing the same as an active ingredient |
| DE8585905236T DE3575296D1 (en) | 1984-10-29 | 1985-10-22 | PYRAZOLIC CARBOXAMIDE COMBINATIONS, THE PRODUCTION THEREOF AND THE BACTERIA-KILLING AGENTS CONTAINING THEM. |
| US06/852,967 US4742074A (en) | 1984-10-29 | 1985-10-22 | Pyrazolecarboxamide derivative and fungicide containing it as active ingredient |
| KR1019860700406A KR920003893B1 (en) | 1984-10-29 | 1985-10-22 | Pyrazolecarboxamide derivatives |
| EP85905236A EP0199822B1 (en) | 1984-10-29 | 1985-10-22 | Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients |
| PCT/JP1985/000591 WO1986002641A1 (en) | 1984-10-29 | 1985-10-22 | Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients |
| BR8506974A BR8506974A (en) | 1984-10-29 | 1985-10-22 | PIRAZOLCARBOXAMIDE DERIVATIVE, PROCESS FOR ITS PREPARATION AND FUNGICIDE CONTAINING THE SAME AS AN ACTIVE SUBSTANCE |
| CA000496744A CA1262735A (en) | 1985-06-05 | 1985-12-03 | Pyrazolecarboxamide derivative and fungicide containing it as active ingredient |
| MYPI87000679A MY100073A (en) | 1984-10-29 | 1987-05-19 | Pyrazolecarboxamide derivative, a method for preparing the same and fungicide containing it as active ingredient. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12194785A JPH064592B2 (en) | 1985-06-05 | 1985-06-05 | Pyrazolcarboxamide compound and fungicide containing the same as an active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61280480A JPS61280480A (en) | 1986-12-11 |
| JPH064592B2 true JPH064592B2 (en) | 1994-01-19 |
Family
ID=14823855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12194785A Expired - Lifetime JPH064592B2 (en) | 1984-10-29 | 1985-06-05 | Pyrazolcarboxamide compound and fungicide containing the same as an active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH064592B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5857513B2 (en) | 2010-08-10 | 2016-02-10 | 住友化学株式会社 | Plant disease control composition and use thereof |
-
1985
- 1985-06-05 JP JP12194785A patent/JPH064592B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61280480A (en) | 1986-12-11 |
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