JPS6048965A - 3-methyl-4-difluoromethyl-delta2-1,2,4-triazolen-5-one and its preparation - Google Patents
3-methyl-4-difluoromethyl-delta2-1,2,4-triazolen-5-one and its preparationInfo
- Publication number
- JPS6048965A JPS6048965A JP15761783A JP15761783A JPS6048965A JP S6048965 A JPS6048965 A JP S6048965A JP 15761783 A JP15761783 A JP 15761783A JP 15761783 A JP15761783 A JP 15761783A JP S6048965 A JPS6048965 A JP S6048965A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- difluoromethyl
- formula
- reaction
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- 239000012442 inert solvent Substances 0.000 abstract description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、
一般式(IJ
(但し、式中Rは低級アルキル基又はプロパルギル基を
示す。)
で表わされる6−メチル−4−ジフルオロメチル−Δ2
−1.2.4−トリアゾリン−5−オン類、並びに
構造式(II)
で表わされる1−(S−ヒドロキシフェニル)−5−メ
チル−4−ジフルオロメチル−Δ2−12.4−)リア
シリ/−5−オンに
一般式(III)
R4備
(但し、式中Rは低級アルキル基又はプロパルギル基を
示し、Xはハロゲン原子を示す。)で表わされる化合物
を反応させることを特徴とする一般式(11で表わされ
る化合物の製造方法に関する。Detailed Description of the Invention The present invention provides 6-methyl-4-difluoromethyl-Δ2 represented by the general formula (IJ (in the formula, R represents a lower alkyl group or a propargyl group))
-1.2.4-triazolin-5-ones and 1-(S-hydroxyphenyl)-5-methyl-4-difluoromethyl-Δ2-12.4-)riasilyl/ -5-one is reacted with a compound represented by the general formula (III) R4 (wherein R represents a lower alkyl group or a propargyl group, and X represents a halogen atom). (Regarding the method for producing the compound represented by 11.
本発明の化合物は文献未記載の新規化合物であシ、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装
な中間体である。本発明はまた、前記式(1)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 compounds of the present invention are novel compounds that have not been described in the literature and are important intermediates for the production of compounds useful as pesticides, especially herbicides. The present invention also provides a method for producing the compound represented by formula (1).
本発明の製造方法を例えば図式的に示すと次の如く表わ
される。For example, the manufacturing method of the present invention can be diagrammatically expressed as follows.
(1) (1)
(但し、式中R及びXは前記と同じ意味を表わす。)
即ち、構造式(Illで表わされる1−(6−ヒドロキ
シフェニル)−3−メチル−4−ジフルオロメチル−Δ
”−1,2,4−)リアゾリン−5−オンと一般式(B
で表わされる化合物とを塩基の存在下、不活性溶媒中に
て反応させることによシ一般式(1)で示される3−メ
チル−4−ジフルオロメチル−7112−1,2,4−
)リアゾリン−5−オン類を得ることができる。(1) (1) (However, in the formula, R and X have the same meanings as above.) That is, 1-(6-hydroxyphenyl)-3-methyl-4-difluoromethyl- Δ
”-1,2,4-) riazolin-5-one and general formula (B
3-Methyl-4-difluoromethyl-7112-1,2,4- represented by the general formula (1) by reacting with the compound represented by the formula (1) in an inert solvent in the presence of a base.
) riazolin-5-ones can be obtained.
゛本発明で使用できる不活性溶媒としては、この種の反
応を著しく阻害しないものであれば良<、IHJlf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。Inert solvents that can be used in the present invention include aromatic hydrocarbons such as benzene, toluene, and xylene; methanol and ethanol, as long as they do not significantly inhibit this type of reaction.
プロハノール、クリコール等のアルコール類;ジエチル
エーテル、テトラヒドロフラン、ジオキサン等のエーテ
ル類;アセトン、メチルエチルケトン、シクロヘキサノ
ン等のケトン類:酢酸エチ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
級脂肪族アミド類、水、ジメチルスルホキシド等を挙げ
ることができる。Alcohols such as prohanol and glycol; ethers such as diethyl ether, tetrahydrofuran, and dioxane; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; lower fatty acid esters such as ethyl acetate; lower aliphatic amides such as dimethylformamide and dimethylacetamide , water, dimethyl sulfoxide and the like.
これらの溶媒は、単独で、または混合物として使用する
ことができる。These solvents can be used alone or in mixtures.
本発明の反応で使用することの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
す) IJ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、トリメチルアミン
、トリエチルアミン、ジエチルアニリン、1.8−ジア
ザビシクロ−(5,4,O〕−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 in the reaction of the present invention include sodium carbonate, sodium hydride, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, potassium hydroxide, potassium hydroxide, and alkali metals. Examples include inorganic bases such as alcolade, and organic bases such as pyridine, trimethylamine, triethylamine, diethylaniline, and 1,8-diazabicyclo-(5,4,O]-7-undecene.
又、トリエチルベンジルアンモニウムクロライド等の相
聞移動触媒も使用することができる。Phase transfer catalysts such as triethylbenzylammonium chloride can also be used.
本発明反応は加熱下に行なわれ、反応温度は40乃至1
50℃の範囲から適宜選択される。又、反応時間は1乃
至6時間の範囲から選択される。The reaction of the present invention is carried out under heating, and the reaction temperature is 40 to 1
The temperature is appropriately selected from the range of 50°C. Further, the reaction time is selected from the range of 1 to 6 hours.
本発明反応は等モル反応であるので、各反応成分を等モ
ル使用して行われるが、またいずれか一方の成分を過剰
に使用しても良い。Since the reaction of the present invention is an equimolar reaction, it is carried out using equimolar amounts of each reaction component, but one of the components may be used in excess.
反応終了後、常法に従い処理すれば目的とする式(υで
表わされる化合物を得ることができる。After completion of the reaction, the desired compound represented by the formula (υ) can be obtained by processing according to a conventional method.
構造式(Inで表わされる1−(5−ヒドロキシフェニ
ル)−6−メチル−4−ジフルオロメチル−Δ2−トリ
アゾリンー5−オンは例えば下記に図示する方法で合成
するとと示できる。1-(5-hydroxyphenyl)-6-methyl-4-difluoromethyl-Δ2-triazolin-5-one represented by the structural formula (In) can be synthesized, for example, by the method illustrated below.
(IX) (■ (支)
(V) (IV) (旬
(但し、式中Rは低級アルキル基を示し、2はハロゲン
原子を示す。)
構造式(■で表わされるヒドラジンと一般式(■)で表
わされる化合物とを不活性溶媒中に加熱下で閉環反応を
行い構造式(■)で表わされる1−(3−ニトロフェニ
ル)−3−メチル−Δ2−1゜2.4−)リアゾリン−
5−オンとし、この式(■)で表わされる化合物を不活
性溶媒中で一般式(W)で表わされる化合物と反応させ
構造式(■で表わされる1−(5−ニトロフェニル)−
6−メチル−4−ジフルオロメチル−Δ2−1.2.4
− )リアゾリン−5−オンとし、この化合物(■を還
元剤の存在下、還元することにより構造式(財)で表わ
される1−(3−アミノフェニル)−3−メチル−4−
ジフルオロメチル−Δ2−1.2.4−トリアゾリン−
5−オンとし、この化合物(fV)をジアゾ化、次いで
熱分解することによって構造式(II)で表わされる1
−(5−ヒドロキシフェニル>−5−メfルー4−ジフ
ルオロメ−f−に一Δ2−1.2.4−)リアゾリン−
5−オンを得ることができる。(IX) (■ (branch) (V) (IV) (However, in the formula, R represents a lower alkyl group, and 2 represents a halogen atom.) Hydrazine represented by the structural formula (■) and the general formula (■ ) in an inert solvent under heating to form a 1-(3-nitrophenyl)-3-methyl-Δ2-1゜2.4-) liazoline represented by the structural formula (■). −
5-one, and the compound represented by the formula (■) is reacted with the compound represented by the general formula (W) in an inert solvent to obtain 1-(5-nitrophenyl)- represented by the structural formula (■).
6-Methyl-4-difluoromethyl-Δ2-1.2.4
1-(3-aminophenyl)-3-methyl-4- by reducing this compound (■) in the presence of a reducing agent.
Difluoromethyl-Δ2-1.2.4-triazoline-
5-one, and this compound (fV) is diazotized and then thermally decomposed to obtain 1 represented by the structural formula (II).
-(5-Hydroxyphenyl>-5-Mef-4-difluorome-f-to-Δ2-1.2.4-)Ryazoline-
5-one can be obtained.
以下に本発明化合物の代表例を第1表に示すが本発明は
これに限定されるものではない。Representative examples of the compounds of the present invention are shown in Table 1 below, but the present invention is not limited thereto.
第 1 表 以下に本発明の実施例の若干を示す。Table 1 Some examples of the present invention are shown below.
実施例1
l−(5−ヒドロキシフェニル)−3−メf−ルー4−
ジフルオロメチル−Δ2−1.2.4− )リアゾリン
−5−オン28.5f (0,12モル)、プロパルギ
ルプロミド14.39(α12モル)、炭ffiカリウ
ム16.5f(α12モル)及びアセトン150m1の
混合物を還流下4時間反応を行う。反応終了後、反応液
を冷却し、析出した塩を濾過することによシ除き、f液
から溶媒を留去することにより結晶を得る。得られた結
晶をイソブロノくノールから再結することによ#)3[
L!Is’の1−(3−プロパルギルオキシフェニル)
−3−メチル−4−ジフルオロメチル−Δ2−1.2.
4− )リアゾリン−5−オンを得る。Example 1 l-(5-hydroxyphenyl)-3-meth-4-
difluoromethyl-Δ2-1.2.4-) liazolin-5-one 28.5f (0.12 mol), propargyl bromide 14.39 (α 12 mol), charcoal ffipotassium 16.5f (α 12 mol) and acetone 150 ml of the mixture is reacted for 4 hours under reflux. After the reaction is completed, the reaction solution is cooled, the precipitated salt is removed by filtration, and the solvent is distilled off from the solution f to obtain crystals. By recrystallizing the obtained crystals from isobrophenol,
L! Is' 1-(3-propargyloxyphenyl)
-3-Methyl-4-difluoromethyl-Δ2-1.2.
4-) Riazolin-5-one is obtained.
融点99〜101℃ 収率 91.8%実施例2
l−(5−ヒドロキシフェニル)−2−メチル−4−ジ
フルオロメチル−Δ!−1,2,4−)リアゾリン−5
−オン24.0SF(α1モル)及び水酸化ナトリウム
4.29 (0,1モル)をエタノール150耐に溶解
し、この溶液に室温下プロパルギルクロリドa2f(1
,11モル)を加え、還流下4時間反応を行う。反応終
了後、反応液を冷却し、水を加えて析出する結晶を濾過
採取し、イングロバノールから再結することによシ2!
1.87の1− (5−プロパルギルオキシフェニル)
−3−メチル−4−ジフルオロメチル−Δ2−1゜2.
4−トリアゾリン−5−オンを得る。Melting point: 99-101°C Yield: 91.8% Example 2 l-(5-hydroxyphenyl)-2-methyl-4-difluoromethyl-Δ! -1,2,4-) riazoline-5
-one 24.0SF (α1 mol) and sodium hydroxide 4.29 (0.1 mol) were dissolved in ethanol 150 resistant, and this solution was added to propargyl chloride a2f (1 mol) at room temperature.
, 11 mol) and the reaction was carried out under reflux for 4 hours. After the reaction is completed, the reaction solution is cooled, water is added, the precipitated crystals are collected by filtration, and re-crystallized from inglobanol.
1.87 1-(5-propargyloxyphenyl)
-3-Methyl-4-difluoromethyl-Δ2-1゜2.
4-triazolin-5-one is obtained.
実施例3
l−(3−ヒドロキシフェニル)−5−メチル−4−ジ
フルオロメチル−Δ2−1.2.4−トリアゾリン−5
−オン2a5S’ (112モル)、インプロピルプロ
ミド1tay(o、12モル)、炭酸カリウム1tsy
(α12モル)及びアセトン15011Ilの混合物
を還流下4時間反応を行う。Example 3 l-(3-hydroxyphenyl)-5-methyl-4-difluoromethyl-Δ2-1.2.4-triazoline-5
-one 2a5S' (112 mol), inpropylbromide 1tay (o, 12 mol), potassium carbonate 1tsy
A mixture of (α12 mol) and 15011 Il of acetone is reacted for 4 hours under reflux.
反応終了後、反応液を冷却し、析出した塩をf別し、f
液から溶媒を留去することによシ油状物として1−(3
−インプロポキシフェニル)=3−メチル−4−ジフル
オロメチル−Δ2−1゜2.4−トリアゾリン−5−オ
ン19.6S’を得る。After the reaction is completed, the reaction solution is cooled, the precipitated salt is separated by f, and f
By distilling off the solvent from the solution, 1-(3
-inpropoxyphenyl)=3-methyl-4-difluoromethyl-Δ2-1°2.4-triazolin-5-one 19.6S' is obtained.
収率6αl
NMRacDCIs 1.4〜ts(d、6H)、z、
4s(S、3H)MS
4.5〜4.8 (m、 IH) 6.05〜7.98
(t、 IH)6.6〜6.85 (m、 IH)
7.1〜7.5 (m、3H)特許出願人 日本農薬株
式会社
518−Yield 6αl NMRacDCIs 1.4~ts (d, 6H), z,
4s (S, 3H) MS 4.5-4.8 (m, IH) 6.05-7.98
(t, IH) 6.6-6.85 (m, IH)
7.1-7.5 (m, 3H) Patent applicant Nihon Nohyaku Co., Ltd. 518-
Claims (2)
示す。) で表わされる3−メチル−4−ジフルオロメチル−Δ2
−1.2.4− )リアゾリン−5−オン類。(1) 3-methyl-4-difluoromethyl-Δ2 represented by general formula (I): (wherein R represents a lower alkyl group or a propargyl group)
-1.2.4-) Riazolin-5-ones.
チル−4−ジフルオロメチル−/−1,2,4−)リア
ゾリン−5−オンに一般式(110: %式%() (但し、式中Rは低級アルキル基又はプロパルギル基を
示し、Xはハロゲン原子を示す。)で表わされる化合物
を反応させることを特徴とする一般式(1) (但し、式中Rは前記と同じ意味を表わt)で表わされ
る3−メチル−4−ジフルオロメチル−Δ!−1,2,
4−、)リアゾリン−5−オン類の製法。(2) Structural formula (■): The general formula (110: General formula (1) characterized by reacting a compound represented by the formula %() (wherein R represents a lower alkyl group or a propargyl group, and X represents a halogen atom) (however, the formula R represents the same meaning as above; 3-methyl-4-difluoromethyl-Δ!-1,2,
4-,) Method for producing riazolin-5-ones.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15761783A JPS6048965A (en) | 1983-08-29 | 1983-08-29 | 3-methyl-4-difluoromethyl-delta2-1,2,4-triazolen-5-one and its preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15761783A JPS6048965A (en) | 1983-08-29 | 1983-08-29 | 3-methyl-4-difluoromethyl-delta2-1,2,4-triazolen-5-one and its preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6048965A true JPS6048965A (en) | 1985-03-16 |
Family
ID=15653640
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP15761783A Pending JPS6048965A (en) | 1983-08-29 | 1983-08-29 | 3-methyl-4-difluoromethyl-delta2-1,2,4-triazolen-5-one and its preparation |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6048965A (en) |
-
1983
- 1983-08-29 JP JP15761783A patent/JPS6048965A/en active Pending
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