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 thereof

Info

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
Application number
JP3611185A
Other languages
Japanese (ja)
Inventor
Hiroyuki Nakanishi
弘幸 中西
Mitsuru Kajioka
梶岡 充
Kuniaki Yanaka
谷中 国昭
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nihon Nohyaku Co Ltd
Original Assignee
Nihon Nohyaku Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd
Priority to JP3611185A priority Critical patent/JPS61197566A/en
Publication of JPS61197566A publication Critical patent/JPS61197566A/en
Pending legal-status Critical Current

Links

Abstract

NEW MATERIAL:1-(2-Fluoro-5-nitrophenyl)-3-methyl-DELTA<2>-1,2,4-triazolin- 5-one of formula I. USE:Intermediate for the production of agricultural chemicals, especially herbicides. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II (R is lower alkyl; X is O or S) with 2-fluoro-5- nitrophenylhydrazine in the presence or absence of a base such as triethylamine.

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)

【特許請求の範囲】[Claims] (1)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。
(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.
(2)一般式(II): ▲数式、化学式、表等があります▼(II) (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。)で表 わされる化合物と2−フルオロ−5−ニトロフェニルヒ
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.
JP3611185A 1985-02-25 1985-02-25 1-(2-fluoro-5-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and production thereof Pending JPS61197566A (en)

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)

Similar Documents

Publication Publication Date Title
US4129656A (en) Thiazolidine derivatives, salidiuretic compositions and methods of effecting salidiuresis employing them
EP0109575A2 (en) Benzoic-acid derivatives, process and means for its production
JPS61197566A (en) 1-(2-fluoro-5-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and production thereof
EP1685098B1 (en) Ortho-substituted pentafluoride sulfanyl-benzenes, method for the production thereof and the use thereof in the form of valuable synthesis intermediate stages
US4087451A (en) 2,3-Dihalo-1,4-dithiocyano-2-butenes and their homologs
US3801588A (en) Certain perfluoroalkylsulfon-amidothiazoles
JPS62240670A (en) Delta2-1,2,4-triazolin-5-one derivative and its production
US3751462A (en) Process for preparation of substituted fluoromethanesulfonanilides
JP2000503993A (en) Method for producing N- (3-amino-4-chlorophenyl) acylamide
JPS5840546B2 (en) 2- Benzimidazole carbamic acid alkyl ester
JPS6051180A (en) Preparation of 1,2,4-triazolin-5-one
JPS606944B2 (en) Method for producing new uracil derivatives
JPS61197567A (en) 1-(2-fluoro-5-nitrophenyl)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one and production thereof
JPS62265274A (en) Delta2-1,2,4-triazolin-5-one derivative and production thereof
JPS61112056A (en) Imidazole derivative and production thereof
JPS61197569A (en) 1-(2-fluoro-5-hydroxyphenyl)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one and production thereof
US4071547A (en) 3-Bromo-2,2-bis(bromomethyl)propyl bromomethanesulfonate
KR800001133B1 (en) Process for preparing 5-sulfamoyl benzoic acid substituted by heterocyclic compound
JPS58964A (en) Synthesis of 6-aminonicotic acid nicotinyl ester
AT364836B (en) METHOD FOR PRODUCING NEW O-SUBSTITUTED DERIVATIVES OF (+) - CYANIDAN-3-OLS AND THE SALTS THEREOF
JPS5913513B2 (en) Shinkitsu Fuenki Kagobutsu no Seizouhou
JPS6048974A (en) 1-(3-nitrophenyl)-3-methyl-delta2-1,2,4-triazolin-5-one and its preparation
JPS62106064A (en) Production of diethylene glycol ester
DE102004043937A1 (en) Ortho-substituted pentafluorosulfurane-benzenes, processes for their preparation and their use as synthesis intermediates
JPS62263166A (en) 1,2,4-triazolin-5-one derivative and production thereof