JPS61197566A - 1-(2-fluoro-5-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and production thereof - Google Patents
1-(2-fluoro-5-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and production thereofInfo
- Publication number
- JPS61197566A JPS61197566A JP3611185A JP3611185A JPS61197566A JP S61197566 A JPS61197566 A JP S61197566A JP 3611185 A JP3611185 A JP 3611185A JP 3611185 A JP3611185 A JP 3611185A JP S61197566 A JPS61197566 A JP S61197566A
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- nitrophenyl
- methyl
- formula
- triazolin
- 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.)
- Pending
Links
Abstract
Description
【発明の詳細な説明】
本発明は、構造式（１）：
テ表ワされる１−（２−フルオロ−５−ニトロフェニル
）−３−メチル−Δ”１，２．４−トリアゾリン−５−
オン及びその製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a compound having the structural formula (1): −
This invention relates to on and its manufacturing method.
本発明の上記式（１１で表わされる化合物は文献未記載
の新規化合物であり、農薬、特に除草剤として有用な化
合物を製造するための重要な中間体である。また、本発
明は式（１１で表わされる化合物の製造方法をも提供す
るものである。The compound represented by the above formula (11) of the present invention is a novel compound that has not been described in literature, and is an important intermediate for producing compounds useful as agricultural chemicals, especially herbicides. The present invention also provides a method for producing a compound represented by:
本発明の製法を例えば図式的に示すと、次の如く表わ嘔
れる。For example, the manufacturing method of the present invention can be shown diagrammatically as follows.
（［１（１）
（但し、式中、
Ｒは低級アルキル基を示し、
Ｘは酸素原子又は硫黄原子を示す。）
即ち、一般式（Ｉｌｌで表わされる化合物と２−フルオ
ロ−５−二トロフェニルヒトラシントヲ適当な溶媒の存
在下及び塩基の存在下又は不存在下で反応させることに
より構造式（１１で表わされル１−（２−フルオロ−５
−二トロフェニル）−３−メチル−Δ２−１．２．４−
）リアシリ／−５−オンを得ることができる。([1(1) (However, in the formula, R represents a lower alkyl group, and X represents an oxygen atom or a sulfur atom.) That is, a compound represented by the general formula (Ill and 2-fluoro-5-nitro By reacting phenylhytracine in the presence of a suitable solvent and the presence or absence of a base, 1-(2-fluoro-5
-nitrophenyl)-3-methyl-Δ2-1.2.4-
) can be obtained.
上記一般式（［１中の２個のＲは同−又は異なってもよ
い。The above general formula ([2 R's in 1 may be the same or different.
本発明の上記製法で使用できる溶媒としては、この種の
反応の進行を著しく阻害しないものであれば艮く、例え
ばベンゼン、トルエン、キシレン等の芳香族炭化水素類
；メタノール、エタノール、プロパツール、グリコール
等のアルコール類；酢酸エステル等の低級脂肪酸エステ
ル類、ジメチルホルムアミド、ジメチルアセトアミド等
の低級脂肪酸アミド類；水、ジメチルスルホキシド等を
挙げることができる。これらの溶媒は、単独で又は混合
物として使用される。Solvents that can be used in the above production method of the present invention include those that do not significantly inhibit the progress of this type of reaction, such as aromatic hydrocarbons such as benzene, toluene, and xylene; methanol, ethanol, propatool, Examples include alcohols such as glycol; lower fatty acid esters such as acetate; lower fatty acid amides such as dimethylformamide and dimethylacetamide; water, dimethyl sulfoxide, and the like. These solvents are used alone or in mixtures.
使用できる塩基としては、例えば炭酸す） ＩＪウム、
水素化ナトリウム、炭酸カリウム、炭酸水素ナトリウム
、炭酸水素カリウム、水酸化ナトリウム、水酸化カリウ
ム及びアルカリ金属のアルコラード等の無機塩基、ピリ
ジン、トリノチルアミン、トリエチルアミン、：）エチ
ルアニリン、１，８−ジアザビシクロ−（５，４，０）
−７−ウンデセン等の有機塩基を挙げることができる
。Examples of bases that can be used include carbonic acid, IJium,
Inorganic bases such as sodium hydride, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium hydroxide, potassium hydroxide and alkali metal alcoholades, pyridine, trinotylamine, triethylamine, :) ethylaniline, 1,8-diazabicyclo -(5,4,0)
Organic bases such as -7-undecene can be mentioned.
゛反応は一般に加熱下で行われ、反応温度は４０乃至１
５０℃の範囲から適宜選択すれば良い。゛The reaction is generally carried out under heating, and the reaction temperature is 40 to 1
It may be selected appropriately from the range of 50°C.
本発明の反応は等モル反応であるので、各反応成分を等
モル使用することによって行れるが、またいづれか一方
の反応成分を過剰に使用しても艮い。Since the reaction of the present invention is an equimolar reaction, it can be carried out by using equimolar amounts of each reaction component, but it is also permissible to use an excess of any one of the reaction components.
反応時間は１乃至１０時間の範囲から適宜選択すれば艮
い。The reaction time may be appropriately selected from the range of 1 to 10 hours.
反応終了後、富法に従い反応液を処理し泪的物を単離す
れば良い。After the reaction is completed, the reaction solution may be treated according to the Fu method to isolate the oxidative substance.
以下に若干の実施例を挙げるが本発明はこれらに限定さ
れるものではない。Some examples are listed below, but the present invention is not limited thereto.
実施例１
２−フルオロ−５−ニトロフェニルヒドラジノ１．０１
’（（１００６モル）及ヒエトキシメチレンウレタン０
．９６９ （α００６モル）をキシレン２０ｄ中に懸濁
させ、６０〜７０℃で５時間反応させた後、トリエチル
アミンＣＬ６４ｆ／Ｃα００６３モル）を加え、再び８
０℃で１時間反応させた。反応終了後、放冷し、塩酸水
溶液で中和した後、目的物を酢酸エチルで抽出した。次
いでこの抽出液を無水硫酸マグネシウムで乾燥した後、
溶媒を減圧留去し、得られた結晶をｎ−へキサンで洗浄
して目的物でめる１−（２−フルオロ−５−二トロフェ
ニル）−６−メチル−Δ”−１，２，４−トリアゾリン
−５−オンα７２りを得た。Example 1 2-Fluoro-5-nitrophenylhydrazino 1.01
'((1006 mol) and hyethoxymethylene urethane 0
．． 969 (α006 mol) was suspended in xylene 20d and reacted at 60-70°C for 5 hours, then triethylamine CL64f/Cα0063 mol) was added and 8
The reaction was carried out at 0°C for 1 hour. After the reaction was completed, the mixture was allowed to cool, neutralized with an aqueous hydrochloric acid solution, and then the target product was extracted with ethyl acetate. After drying this extract with anhydrous magnesium sulfate,
The solvent was distilled off under reduced pressure, and the obtained crystals were washed with n-hexane to obtain the desired product, 1-(2-fluoro-5-nitrophenyl)-6-methyl-Δ''-1,2, 4-triazolin-5-one α72 was obtained.
融点１８ａ２℃、収率５１１３％。Melting point: 18a2°C, yield: 5113%.
実施例２
２−フルオロ−５−二トロフェニルヒトラシン２．５７
ｆ（１０１５モル）及びエトキシメチレンウレタン１５
９１（００２２５モル）ヲエタノール５、ローに溶解し
、６５時間加熱還流した。放冷後、反応液に水を加え、
塩酸水溶液で中和した後、析出し、た結晶をＰＩし、ｎ
−へキサンで洗浄して１−（２−フルオロ−５−ニトロ
フェニル） ３ ＋’メチルーΔ”−１，２，４−）
リアゾリン−５−オン五２４ｆを得た。Example 2 2-Fluoro-5-nitrophenylhytracine 2.57
f (1015 mol) and ethoxymethylene urethane 15
91 (0.0225 mol) was dissolved in 5.0 ml of ethanol and heated under reflux for 65 hours. After cooling, water was added to the reaction solution.
After neutralization with an aqueous hydrochloric acid solution, the precipitated crystals were subjected to PI, and
-washed with hexane to form 1-(2-fluoro-5-nitrophenyl) 3 +'methyl-Δ”-1,2,4-)
Ryazolin-5-one 524f was obtained.
収率９ＣＬ８チ。Yield 9CL8chi.
特許出願人 日本農薬株式会社 （ほか１名）Patent applicant: Nihon Nohyaku Co., Ltd. (1 other person)
Claims (2)
）−５−メチル−Δ＾２−１，２，４−トリアゾリン−
５−オン。(1) Structural formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼1-(2-fluoro-5-nitrophenyl)-5-methyl-Δ^2-1,2, represented by (I) 4-Triazoline-
5-on.
ドラジンとを塩基の存在下又は不存在下で反応させるこ
とを特徴とする構造式（ I ）： ▲数式、化学式、表等があります▼（ I ） で表わされる１−（２−フルオロ−５−ニトロフェニル
）−５−メチル−Δ＾２−１，２，４−トリアゾリン−
５−オンの製造方法。(2) General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (However, in the formula, R represents a lower alkyl group, and X represents an oxygen atom or a sulfur atom.) Represented by Structural formula (I) characterized by reacting a compound with 2-fluoro-5-nitrophenylhydrazine in the presence or absence of a base: ▲There are mathematical formulas, chemical formulas, tables, etc.▼Represented by (I) 1-(2-fluoro-5-nitrophenyl)-5-methyl-Δ^2-1,2,4-triazoline-
Method for producing 5-one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3611185A JPS61197566A (en) | 1985-02-25 | 1985-02-25 | 1-(2-fluoro-5-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3611185A JPS61197566A (en) | 1985-02-25 | 1985-02-25 | 1-(2-fluoro-5-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61197566A true JPS61197566A (en) | 1986-09-01 |
Family
ID=12460658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3611185A Pending JPS61197566A (en) | 1985-02-25 | 1985-02-25 | 1-(2-fluoro-5-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61197566A (en) |
-
1985
- 1985-02-25 JP JP3611185A patent/JPS61197566A/en active Pending
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