JPS6016978A - Triazolone derivative and fungicide - Google Patents
Triazolone derivative and fungicideInfo
- Publication number
- JPS6016978A JPS6016978A JP12439983A JP12439983A JPS6016978A JP S6016978 A JPS6016978 A JP S6016978A JP 12439983 A JP12439983 A JP 12439983A JP 12439983 A JP12439983 A JP 12439983A JP S6016978 A JPS6016978 A JP S6016978A
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- test
- formula
- benzyl
- fungicide
- Prior art date
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Abstract
Description
【発明の詳細な説明】
ン誘導体及び該化合物全有効成分として含有する殺菌剤
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a bactericidal agent containing a derivative of the present invention and the compound as all active ingredients.
−Z
〔式中R,は水素原子寸たはメチル基であシ、R2は水
素原子またはアルキル基またはベンジル基を示し、Zは
炭素原子数1ないし4のアルキルカルバモイル基、塩素
ないしはメチル基で置換されたフェニルカルバモイル基
、又は、塩素ないしはメチル基で置換されたベンゾイル
基を示す〕本発明化合物の例として代表的なものを例示
すわば、表1に示すごときものが挙げられ、る。-Z [In the formula, R is a hydrogen atom or a methyl group, R2 is a hydrogen atom, an alkyl group, or a benzyl group, and Z is an alkylcarbamoyl group having 1 to 4 carbon atoms, chlorine or a methyl group. A substituted phenylcarbamoyl group or a benzoyl group substituted with chlorine or methyl group] Typical examples of the compounds of the present invention include those shown in Table 1.
尚、化合物の表示u二前記一般式に於ける記号で示す。The compounds are indicated by the symbols in the general formula above.
表1
(3)
本化合物は公知の方法(Arch Pharm 196
830](II)827〜9)に拠υ合成された4−ヒ
ドロキシ−L2+4− ト!Jアゾロンー5−オンをノ
オキザン、ジメチルホルムアミド等の溶謀に溶角イ、又
は、けんだくさせこれにイソシアネートを作用させるか
、あるいはトリエチルアミン、ピリジン等の脱塩化水素
剤の共存下、カルバミン酸ハライド、安息香酸ハライド
を作用させることにより得られる。Table 1 (3) This compound was prepared using a known method (Arch Pharm 196
830] (II) 4-hydroxy-L2+4- synthesized based on 827-9)! JAzolon-5-one is melted or suspended in a solvent such as nooxane or dimethylformamide, and isocyanate is applied thereto, or in the presence of a dehydrochlorination agent such as triethylamine or pyridine, carbamic acid halide, Obtained by reacting with benzoic acid halide.
以下に代表的な合成例全示し更に具体的に説明する。All typical synthesis examples are shown below and will be explained in more detail.
4−ヒドロキシ−1,2,4−)リアゾール−5−オy
0.05mole (5,0!i’)’eジオキサ”/
30m1にけんだくさせ、メチルイソシアネー)4g−
’i加えて3時間加熱還流した。室温まで冷却後生成物
をろ集した。得られた結晶をエチルアルコールから再結
晶し、融点170°(分解)の白色結晶1.91全得た
。4-Hydroxy-1,2,4-)lyazole-5-oy
0.05mole (5,0!i')'edioxa'/
Suspended in 30ml, 4g of methyl isocyanate
'i and heated under reflux for 3 hours. After cooling to room temperature, the product was collected by filtration. The obtained crystals were recrystallized from ethyl alcohol to obtain 1.91 white crystals with a melting point of 170° (decomposition).
(5)
IR−ヌ被りトルデータ
3320 cnr ’(−NT−I−)、1.790
cm−1,17,10m−m−1(−C=
O)N (CDCt3+DMSO−c16)2、70〜
2.80 ppm(d、3H)、8.07 ppm(s
、H()、同(b、1.H)、]、 1.90 ppm
(b、1.H)合成例23−メチル−4−メチルカルバ
モイルオキシ−1,2,4−)リアゾール−5−オン
4−ヒドロキシ−3−メチル−1,2,4−トリアゾー
ル−5−オフ1.5ffノオキサy 10 rnlsメ
チルイソシアネート1 mlとともに還流下2時間加熱
した。室温まで放冷後減圧下溶媒を留去し残滓をエチル
アルコールよシ再結晶し、融点141゜(分解)の白色
結晶1.41を得た。(5) IR-Nu overlap torque data 3320 cnr' (-NT-I-), 1.790
cm-1,17,10m-m-1(-C=O)N (CDCt3+DMSO-c16)2,70~
2.80 ppm (d, 3H), 8.07 ppm (s
, H(), same(b, 1.H), ], 1.90 ppm
(b, 1.H) Synthesis Example 23-Methyl-4-methylcarbamoyloxy-1,2,4-)riazol-5-one 4-hydroxy-3-methyl-1,2,4-triazol-5-off The mixture was heated under reflux for 2 hours with 1 ml of methyl isocyanate. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl alcohol to obtain 1.41 white crystals with a melting point of 141° (decomposed).
NMRヌ被りトル(DMso−a6) ;δ値、2.0
7 ppm(s、3H)、2.65〜2.75 ppm
(d、3H)、8.2 ppm(b、1.H)、]−1
,,67ppm(b、H()合成例34−(o−メチル
ベンゾイルオキシ)−1,,2,4−)リアゾール−5
−オン(6)
4−ヒドロキシ−1,2,4−)リアゾール−5−オy
5.0jlj’iツメチルホルムアミド3 Q ml
(C溶解し、こわ、にトリエチルアミン5.0!?’(
z加え、さらに室温下オルソトルイル酸クロリド7.7
Pffi加えると、激しく発熱する。−夜放置後反応液
を水300 ml中に注ぎ込み、得られた結晶全メタノ
ールより再結晶すると融点]78℃(分解)の微かっ色
の結晶5.09−が得られたO
NMRスペクトルデータ(DMSO−d6)2、59
ppm(s、3I()、7.3〜8.2 ppm(m、
4H)、8、43 pprn(s、IH)、]、 2.
25 ppm(b、11.T()IRスペクトルデータ
] 770 tyn−’、1.728 cm−’ (−
C=O)合成例41−ベンジルー4−メチルカッl/
/<モイルオキシ−1,2,4−トリアゾルルー5−オ
ン
水酸化カリウム3.3P’を水30m1メタノール30
rnlに溶解し、こわ、に4−ヒドロキシ−1,2,
4−トリアゾール−5−オン5.OL!−を添加する。NMR overlap (DMso-a6); δ value, 2.0
7 ppm (s, 3H), 2.65-2.75 ppm
(d, 3H), 8.2 ppm (b, 1.H), ]-1
,,67ppm(b,H() Synthesis Example 34-(o-methylbenzoyloxy)-1,,2,4-)riazole-5
-one (6) 4-hydroxy-1,2,4-)lyazol-5-oy
5.0ml methylformamide 3Q ml
(C dissolved, stiff, triethylamine 5.0!?'(
Add z and further add orthotoluylic acid chloride 7.7 at room temperature.
When Pffi is added, it generates intense heat. -After standing overnight, the reaction solution was poured into 300 ml of water, and the resulting crystals were recrystallized from all methanol to give pale brown crystals with a melting point of 78°C (decomposition).O NMR spectrum data ( DMSO-d6) 2, 59
ppm(s, 3I(), 7.3-8.2 ppm(m,
4H), 8, 43 pprn(s, IH), ], 2.
25 ppm (b, 11.T() IR spectrum data] 770 tyn-', 1.728 cm-' (-
C=O) Synthesis Example 41-benzyl-4-methylkat/
/<Moyloxy-1,2,4-triazol-5-one Potassium hydroxide 3.3P' water 30ml methanol 30
Dissolved in rnl, stiff, 4-hydroxy-1,2,
4-triazol-5-one5. OL! − is added.
冷却下攪拌しながら、ベンジルブロマイド9.4. !
i”(r滴下し、滴下後−夜装置する。生じた結、晶を
ろ集し、融点125°の1−ベンジル−4−ヒドロキシ
−1,2,4−トリアゾール−5−オン白色結晶751
を得た。While stirring under cooling, add benzyl bromide 9.4. !
i''(r) was added dropwise, and the apparatus was heated overnight after the addition. The resulting crystals were collected by filtration to give 751 white crystals of 1-benzyl-4-hydroxy-1,2,4-triazol-5-one with a melting point of 125°.
I got it.
IR1710crn−1
NMR(DMso−d6)
5、18 ppm(8−2H)、7.42 ppm(s
、5H)8.0 ppm(s、1.H)、11.75
ppm(b 、 ]、IH■−ベンジル〜4−ヒドロキ
シー1.2./1−トリアゾール−5−オン481をジ
オキサン1.5m7!に溶解し、l・リエチルアミン4
滴を加え、さらにメチルイソシアネー1−2.0 Pを
加えると、直ちに結晶が析出する。これをろ集して融点
147°の1−ベンジル−4−メチルカル/6モイルオ
キシー1.2.4−トリアゾール−5−オンの結晶5.
2g’を得た。IR1710crn-1 NMR (DMso-d6) 5, 18 ppm (8-2H), 7.42 ppm (s
, 5H) 8.0 ppm (s, 1.H), 11.75
ppm (b, ], IH■-benzyl~4-hydroxy-1.2./1-triazol-5-one 481 was dissolved in 1.5 m7! of dioxane, and l.ethylamine 4
When a drop of 1-2.0 P of methyl isocyanate is added, crystals immediately precipitate. This was collected by filtration to crystallize 1-benzyl-4-methylcal/6moyloxy-1.2.4-triazol-5-one with a melting point of 147°5.
2g' was obtained.
本発明化合物は床机な農園芸作物の病害の防除に効果的
でちり、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 diseases of agricultural and horticultural crops, and the main ones include the following.
水稲 ごま葉枯;
豆類 褐斑、菌核病;
トマト 疫、灰色かび、葉かび、輪紋病;キュウリ 灰
色かび、べと、灰色疫、黒星、苗立枯、っる割;レタス
菌核病;
カンキツ 黒色、そうか病;
リンゴ モニリア、黒星、斑点落葉病:ナシ 黒星、黒
斑病;
モモ 灰層、黒星、フォモプレス腐敗、菌病;ブドウ
ベと、黒疫、晩腐病。Paddy rice Sesame leaf blight; Beans brown spot, sclerotia; Tomato blight, gray mold, leaf mold, ring spot blight; cucumber gray mold, downy mildew, gray blight, black star, seedling die-off, sclerotinia; lettuce sclerotium blight ; Citrus black, scab; Apple monilia, black star, leaf spot; Pear black star, black spot; Peach gray layer, black star, fomopress rot, fungal disease; grapes
Bae, black plague, and late rot.
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、水利剤、乳剤、油剤その他農薬製剤上慣用
されている適当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、又他の種類の殺菌剤や殺虫剤除草剤、肥料等と併用
、混合することもできる。As mentioned above, the compound of the present invention can be used as a fungicide for agricultural and horticultural purposes, but it can be used as it is or mixed with a carrier (diluent) to form powders, granules, irrigation agents, emulsions, oils, and other suitable agrochemical preparations. used as an agent. In this case, spreading agents, emulsifiers, wetting agents, fixing agents, etc. are used as appropriate, and they can also be used in combination or mixed with other types of fungicides, insecticides, herbicides, fertilizers, etc.
実施例1 粉 剤
表中にある化合物 3部
クレー 40部
タルク 57部
(9)
実施例2 水和剤
表中にある化合物 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
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、
、L)として100〜1500.1i’/IQa。Example 1 Powder Compounds listed in the table 3 parts Clay 40 parts Talc 57 parts (9) Example 2 Compounds listed in the wettable powder table 75 parts Polyoxyethylene alkyl allyl ether 9 parts White carbon 16 parts Regarding the amount of spraying Although there is no particular restriction, when spraying on fields where crops are usually grown, active ingredient compounds (A,
, L) from 100 to 1500.1i'/IQa.
また、土壌中に施用する場合には1〜8 kf? A、
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。Also, when applying into soil, 1 to 8 kf? A,
1. /10a is appropriate. Of course, this is just a guideline, and it depends on the type of crop, the type of disease, the degree of damage,
The dosage may be adjusted as necessary, taking into consideration factors such as the season, weather, and drug dosage form.
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アシ
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。Hereinafter, typical test examples will be shown to specifically explain the effects of the compounds of the present invention. 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梨黒斑病菌に対する胞子発芽阻止試験
〈試験方法〉
アンズ培地に7〜10日間培養したAlternari
a(lO)
Kikuchiana の分生胞子と薬液を混合し、顕
微鏡100倍1視野当り約20個になるように調整する
。Test Example-1 Spore germination inhibition test against pear black spot fungus <Test method> Alternari cultured on apricot medium for 7 to 10 days
a(lO) Kikuchiana conidia and a drug solution are mixed and adjusted to about 20 conidia per field of view under a microscope at 100x magnification.
スライドグラス上に、この混合懸濁液をo、o2m1滴
下し、温度27℃、湿度1. OO%に20時間保った
後に検鏡して、胞子発芽の有無を調査する。This mixed suspension was dropped onto a slide glass at a temperature of 27°C and a humidity of 1.2ml. After keeping it at OO% for 20 hours, examine it under a microscope to check for spore germination.
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.
試験例−2カンキツ黒点病菌に対する胞子発芽阻止試験
〈試験方法〉
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1視野当
り約20個になるように調整する。Test Example-2 Spore germination inhibition test against citrus black spot fungus <Test method> Diaporthe citr cultured on dead citrus branches
Mix the conidia of conidia i and the drug solution, and adjust to about 20 conidia per field of view under a microscope at 100x magnification.
スライドグラス」二に、この混合懸濁液を0.02鮮滴
下し、温度27℃、湿度100チに20時間保った後に
、検顕j〜で胞子発芽の有無を調査する。0.02 drop of this mixed suspension was placed on a slide glass, kept at a temperature of 27° C. and a humidity of 100° C. for 20 hours, and the presence or absence of spore germination was examined using a microscopic microscope.
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.
〈試験結果〉
試験例−3梨黒斑病効力試験
〈試験方法〉
梨(品種ユニ十世紀)の展開葉に、所定濃度に希釈した
薬液を葉5枚当り20罰噴霧散布し、室内で風乾した。<Test Results> Test Example-3 Pear Black Spot Efficacy Test <Test Method> A chemical solution diluted to a specified concentration was sprayed at 20 times per 5 leaves on the unfolded leaves of pears (variety: Uni Jussei), and air-dried indoors. did.
風乾後、アンズ培地で培養したAlternaria
Kikuchianaの分生胞子を噴霧接種し、1亘ち
に25℃、湿度100係の条件下に3日間静置し、3日
後に発病面積を調査した。Alternaria cultured in apricot medium after air drying
Conidia of Kikuchiana were spray inoculated and left to stand for 3 days at 25° C. and humidity of 100%, and the diseased area was examined after 3 days.
但し、連数は5連とする。However, the number of runs shall be 5.
〈試験結果〉
試験例−4かんきつ黒点病効力試験
〈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た後に温室内で
風乾した。みかん枯枝で培養したDiaporthe
citriの分生胞子を噴霧接種した後直ちに、温度2
3℃、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。<Test Results> Test Example-4 Citrus Black Spot Efficacy Test <Test Method> When the new shoots of potted mandarin oranges (variety: Natsukan) were developing, a sufficient amount of a chemical solution diluted to a specified concentration was sprayed and then air-dried in a greenhouse. . Diaporthe cultivated on mandarin orange branches
Immediately after spray inoculation with conidia of C. citri, temperature 2.
It was kept in the dark at 3°C and 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、連数は3連とする。However, the number of runs shall be three.
(13)
発病程度 病斑数7葉
0
1 1〜3
2 4〜6
3 7〜10
4 11〜
〈試験結果〉
試験例−5犬根萎黄病効力試験
〈試験方法〉
犬根萎黄病菌(Fusariuw oxysporum
f、 rophani)の厚膜胞子により人工的に汚
染させた土壌を直径(14)
15m+の素焼鉢につめる。表面にあらかじめ発芽させ
た大根の種子(品種:青首宮重)を鉢当910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。(13) Disease severity Number of lesions 7 leaves 0 1 1-3 2 4-6 3 7-10 4 11- <Test results> Test example-5 Canine root wilt efficacy test <Test method> Canine root wilt yellow disease fungus (Fusariuw) oxysporum
Clay pots with a diameter of (14) 15 m+ are filled with soil artificially contaminated with chlamydospores of F. rophani). 910 radish seeds (variety: Aokubi Miyaju) that have been germinated in advance are sown on the surface of the pot, and the soil is covered with contaminated soil. Immediately, a chemical solution diluted to a predetermined concentration is uniformly applied to the surface, and then lightly sprinkled with water. after that,
Leave the pot in the greenhouse and water as needed.
処理60日後に発病の有無、程度を以下の規準に従がい
調査する。60 days after treatment, the presence or absence of disease onset and its severity are investigated according to the following criteria.
但し、連数は5連とする。However, the number of runs shall be 5.
試験例−6キーウリ苗立詰病効力試駄
〈試験方法〉
キュウリ苗立枯病菌(Pythium apharid
ermatum)で人工的に汚染させた土壌を直径15
mの素焼鉢につめる。表面にあらかじめ発芽させたキュ
ウリの種子(品種:相撲半白)を鉢当シ20粒播種した
後に、汚染土で覆土し、直ちに所定の濃度に希釈した薬
液の317m2相当量を表面に均一に潅注する。潅注後
軽く潅水し温室内に放置した。試験中は適宜潅水し、処
理14日後に発芽本数、倒伏本数を調べ、次の様に防除
価を算定した。Test Example-6 Efficacy Test for Pythium Seedling Blight (Test Method) Pythium apharid
ermatum) in a diameter of 15 mm.
Pour into an M clay pot. After sowing 20 pre-germinated cucumber seeds (variety: Sumo Hanshiro) on the surface, cover the soil with contaminated soil, and immediately sprinkle the equivalent of 317 m2 of a chemical solution diluted to the specified concentration uniformly over the surface. do. After irrigation, the plants were lightly watered and left in the greenhouse. During the test, the plants were watered appropriately, and 14 days after the treatment, the number of germinated plants and the number of lodging plants were examined, and the control value was calculated as follows.
〈試験結果〉
試験例−7豆類菌核病効力試験
〈試験方法〉
インケゝン豆(品種:マスターピース)の初生葉に所定
の濃度に水で希釈した薬液の2葉に対し10m/(相当
量を噴霧散布した。風乾後、PDA培、地で培養した豆
類菌核病菌(Sclerotiria sclerot
iorum)の菌そうをコルクポーラ−で打ち抜き葉面
上に接種した。接種後、直ちに、温度23℃湿度100
チの暗黒条件下においた。接種3日後に病斑面積(17
)
を調査した。<Test Results> Test Example-7 Bean Sclerotinia Disease Efficacy Test <Test Method> A chemical solution diluted with water to a specified concentration was applied to the first leaves of Japanese bean (variety: Masterpiece) at 10 m/(equivalent amount) per two leaves. After air-drying, the legume sclerotia fungus (Scleroteria sclerotide) cultured on PDA medium was sprayed.
iorum) was punched out with a cork polar and inoculated onto the leaf surface. Immediately after inoculation, the temperature is 23℃ and the humidity is 100℃.
The samples were placed under dark conditions. Three days after inoculation, the lesion area (17
) investigated.
但し、連数は5連とする。However, the number of runs shall be 5.
〈試験結果〉 (18)<Test results> (18)
Claims (1)
素原子またはアルギル基またはベンジル基ヲ示し、Zは
炭素原子数1ないし4のアルキルカルバモイル基、塩素
ないしはメチル基で置換されたフェニルカルバモイル基
、又は、塩素ないしはメチル基で置換されたベンゾイル
基を示す〕で示されるトリアシロン誘導体。 2)一般式 (1) 〔式中R11d:水素原子脣たはメチル基でちゃ、R2
は水素原子またはアルキル基またはベンジル基を示し、
2は炭素原子数1ないし4のアルキルカル・ぐモイル基
、塩素ないしはメチル基で置換されたフェニルカルバモ
イル基、又は、塩素ないしはメチル基で置換されたベン
ゾイル基を示す〕で示されるトリアシロン誘導体を有効
成分として含有する殺菌剤。[Scope of Claims] 1) General formula [wherein R1 is a hydrogen atom or a methyl group, R2 is a hydrogen atom, an argyl group or a benzyl group, and Z is an alkylcarbamoyl group having 1 to 4 carbon atoms] a phenylcarbamoyl group substituted with chlorine or methyl group, or a benzoyl group substituted with chlorine or methyl group]. 2) General formula (1) [In the formula, R11d: hydrogen atom or methyl group, R2
represents a hydrogen atom, an alkyl group or a benzyl group,
2 represents an alkylcar-gumoyl group having 1 to 4 carbon atoms, a phenylcarbamoyl group substituted with chlorine or methyl group, or a benzoyl group substituted with chlorine or methyl group]. A disinfectant contained as an ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12439983A JPS6016978A (en) | 1983-07-07 | 1983-07-07 | Triazolone derivative and fungicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12439983A JPS6016978A (en) | 1983-07-07 | 1983-07-07 | Triazolone derivative and fungicide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6016978A true JPS6016978A (en) | 1985-01-28 |
Family
ID=14884472
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP12439983A Pending JPS6016978A (en) | 1983-07-07 | 1983-07-07 | Triazolone derivative and fungicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6016978A (en) |
-
1983
- 1983-07-07 JP JP12439983A patent/JPS6016978A/en active Pending
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