JP2743441B2 - Cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivative - Google Patents
Cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivativeInfo
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- JP2743441B2 JP2743441B2 JP1049330A JP4933089A JP2743441B2 JP 2743441 B2 JP2743441 B2 JP 2743441B2 JP 1049330 A JP1049330 A JP 1049330A JP 4933089 A JP4933089 A JP 4933089A JP 2743441 B2 JP2743441 B2 JP 2743441B2
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は新規なシクロペンタ〔1,2−Ｃ〕−３−ピラ
ゾールカルボン酸およびそのエステル類に関する。詳し
くは、医薬、農薬、特に殺虫、殺ダニ剤および殺菌剤の
中間体として有用な化合物に関するものである。Description: TECHNICAL FIELD The present invention relates to a novel cyclopenta [1,2-C] -3-pyrazolecarboxylic acid and its esters. In particular, it relates to compounds useful as intermediates for pharmaceuticals, pesticides, especially insecticides, acaricides and fungicides.
ピラゾール系化合物は、医薬、農薬として有用な化合
物であり、その優れた薬効が、近年、注目されている。
特に、ピラゾール環の種々の置換基を導入することによ
り、薬効を改良することが検討されている。Pyrazole compounds are useful as pharmaceuticals and agricultural chemicals, and their excellent medicinal properties have recently been attracting attention.
In particular, it has been studied to improve the drug efficacy by introducing various substituents on the pyrazole ring.
しかしながら、各種薬剤として有効に利用し得るピラ
ゾール系化合物は、入手が困難であり、これまでそのよ
うな目的で製造または利用された化合物は、ほとんど知
られていない。However, pyrazole-based compounds that can be effectively used as various drugs are difficult to obtain, and compounds produced or used for such purposes have not been known so far.
本発明者らは、上記課題に鑑み、鋭意検討した結果、
有用な新規中間体であるピラゾールカルボン酸誘導体を
見出し、本発明を完成するに至った。In view of the above problems, the present inventors have conducted intensive studies,
The present inventors have found a useful novel intermediate, a pyrazolecarboxylic acid derivative, and have completed the present invention.
すなわち本発明の要旨は、下記一般式（Ｉ）で表され
るシクロペンタ〔1,2−Ｃ〕−３−ピラゾールカルボン
酸誘導体に存する。That is, the gist of the present invention resides in a cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivative represented by the following general formula (I).
（上記式中、R1はC1〜C4のアルキル基を示し、R2は水素
原子またはC1〜C3のアルキル基を示し、R3は水素原子ま
たはメチル基を示し、R4は水素原子またはC1〜C4のアル
キル基を示す。ただし、R1がメチル基またはエチル基で
あり、且つR2とR3が共に水素原子である場合、R4はC2〜
C4のアルキル基を示す。） 以下、本発明を詳細に説明する。 (In the above formula, R 1 represents a C 1 -C 4 alkyl group, R 2 represents a hydrogen atom or a C 1 -C 3 alkyl group, R 3 represents a hydrogen atom or a methyl group, and R 4 represents A hydrogen atom or a C 1 to C 4 alkyl group, provided that when R 1 is a methyl group or an ethyl group, and R 2 and R 3 are both hydrogen atoms, R 4 is a C 2 to C 4
C 4 represents an alkyl group. Hereinafter, the present invention will be described in detail.
一般式（Ｉ）においてR1はメチル基、エチル基、ｎ−
プロピル基、イソプロピル基、ｎ−ブチル基、イソブチ
ル基、sec−ブチル基、ｔ−ブチル基等のC1〜C4の直鎖
または分岐鎖アルキル基を示す。R2は水素原子；メチル
基、エチル基、ｎ−プロピル基、イソプロピル基等のC1
〜C3の直鎖または分岐鎖アルキル基を示す。R3は水素原
子またはメチル基を示す。R4は水素原子；メチル基、エ
チル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル
基、イソブチル基、sec−ブチル基、ｔ−ブチル基等のC
1〜C4の直鎖または分岐鎖アルキル基を示す。但し、R1
がメチル基またはエチル基であり、且つR2とR3が共に水
素原子である場合、R4はエチル基、ｎ−プロピル基、イ
ソプロピル基、ｎ−ブチル基、イソブチル基、sec−ブ
チル基、ｔ−ブチル基等のC2〜C4の直鎖または分岐鎖ア
ルキル基である。In the general formula (I), R 1 is a methyl group, an ethyl group, n-
Propyl group, an isopropyl group, n- butyl group, isobutyl group, sec- butyl group, a linear or branched alkyl group of C 1 -C 4 in a t- butyl group and the like. R 2 is a hydrogen atom; C 1 such as methyl, ethyl, n-propyl, isopropyl, etc.
-C 3 represents a linear or branched alkyl group. R 3 represents a hydrogen atom or a methyl group. R 4 is a hydrogen atom; methyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, etc.
A linear or branched alkyl group having 1 -C 4. Where R 1
Is a methyl group or an ethyl group, and when R 2 and R 3 are both hydrogen atoms, R 4 is an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a straight-chain or branched-chain alkyl group of C 2 -C 4 for a t- butyl group and the like.
前記一般式（Ｉ）で表される本発明の化合物のうちエ
ステル類（I a）およびカルボン酸類（I b）は、例えば
下記反応式に従って製造することができる。Among the compounds of the present invention represented by the general formula (I), the esters (Ia) and the carboxylic acids (Ib) can be produced, for example, according to the following reaction formula.
（上記反応式中、R1、R2およびR3は前記一般式（Ｉ）で
定義したとおりであり、ＺはC1〜C4のアルキル基を示
す） すなわち、上記一般式（II）で表される化合物とヒド
ラジン類を水またはメタノール、エタノール、イソプロ
パノール等のアルコール溶媒中、10〜50℃、好ましくは
20〜30℃で反応させることにより、上記一般式（I a）
の化合物を容易に得ることができる。 (In the above reaction formula, R 1 , R 2 and R 3 are as defined in the above general formula (I), and Z represents a C 1 -C 4 alkyl group.) That is, in the above general formula (II) The compound and hydrazines represented by water or methanol, ethanol, alcoholic solvent such as isopropanol, 10 ~ 50 ° C., preferably
By reacting at 20 to 30 ° C., the above-mentioned general formula (Ia)
Can be easily obtained.
また、上記一般式（I a）で表されるエステル類をア
ルカリの存在下、水中またはメタノール、エタノール等
のアルコール中もしくはアルコールと水の混合溶媒中、
20〜100℃で加水分解することにより、上記一般式（I
b）で表されるカルボン酸類を得ることができる。アル
カリとしては、水酸化ナトリウム、水酸化カリウム、炭
酸ナトリウム、炭酸カリウム等が使用される。Further, the ester represented by the above general formula (Ia) in the presence of an alkali in water or in an alcohol such as methanol, ethanol or a mixed solvent of alcohol and water,
By hydrolysis at 20 to 100 ° C., the above-mentioned general formula (I
The carboxylic acids represented by b) can be obtained. As the alkali, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like are used.
上記一般式（I a）で表される化合物は、下記反応式
に従っても製造することができる。The compound represented by the above general formula (Ia) can also be produced according to the following reaction formula.
（上記反応式中、R1、R2およびR3は前記一般式（Ｉ）で
定義したとおりであり、ＺはC1〜C4のアルキル基を示
す） すなわち、上記一般式（II）の化合物とヒドラジンヒ
ドラートを水またはメタノール、エタノール、イソプロ
パノール等のアルコール溶媒中、０〜50℃、好ましくは
10〜30℃で反応させることにより、上記一般式（III）
で表される化合物を得ることができる。得られた上記一
般式（III）で表される化合物とアルキル化剤を塩化メ
チレン、クロロホルム、四塩化炭素、1,2−ジクロロエ
タン等のハロゲン化炭化水素；ベンゼン、トルエン、キ
シレン等の芳香族炭化水素;N,N−ジメチルホルムアミ
ド、Ｎ−メチルピロリドン、ジメチルスルホキシド等の
溶媒中、または無溶媒中で10〜100℃、好ましくは20〜5
0℃で反応させることにより、上記一般式（I a）で表さ
れる化合物を容易に得ることができる。アルキル化剤と
しては、ジメチル硫酸、ジエチル硫酸、ジプロピル硫
酸、ジブチル硫酸、臭化メチル、臭化エチル、臭化プロ
ピル、臭化ブチル、ヨウ化メチル、ヨウ化エチル、ヨウ
化プロピル、ヨウ化ブチル、塩化メチル、塩化エチル、
塩化プロピル、塩化ブチル等が使用可能である。 (In the above reaction formula, R 1 , R 2 and R 3 are as defined in the above general formula (I), and Z represents a C 1 -C 4 alkyl group) That is, in the above general formula (II) Compound and hydrazine hydrate in water or an alcohol solvent such as methanol, ethanol, isopropanol, 0 to 50 ° C., preferably
By reacting at 10 to 30 ° C., the above general formula (III)
Can be obtained. The obtained compound represented by the above general formula (III) and an alkylating agent are combined with a halogenated hydrocarbon such as methylene chloride, chloroform, carbon tetrachloride, and 1,2-dichloroethane; and an aromatic hydrocarbon such as benzene, toluene and xylene. Hydrogen; in a solvent such as N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, or without a solvent, at 10 to 100 ° C., preferably 20 to 5 ° C.
By reacting at 0 ° C., the compound represented by the general formula (Ia) can be easily obtained. As the alkylating agent, dimethyl sulfate, diethyl sulfate, dipropyl sulfate, dibutyl sulfate, methyl bromide, ethyl bromide, propyl bromide, butyl bromide, methyl iodide, ethyl iodide, propyl iodide, butyl iodide, Methyl chloride, ethyl chloride,
Propyl chloride, butyl chloride and the like can be used.
なお、上記一般式（II）で表される化合物は、Org.Sy
nth.,２,531に記載の方法に準じて容易に合成すること
ができる。The compound represented by the above general formula (II) is a compound represented by Org.Sy
nth., 2 , 531.
次に本発明を更に具体的に説明するが、本発明はその
要旨を越えない限り、以下の例に限定されるものではな
い。Next, the present invention will be described more specifically, but the present invention is not limited to the following examples as long as the gist is not exceeded.
実施例１ 2,6−ジメチルシクロペンタ〔1,2−Ｃ〕−３−ピラゾー
ルカルボン酸エチルエステルの製造 ２−ケトシクロペンチルグリオキザル酸エチルエステ
ル46.1gのエタノール100ml溶液に20〜25℃でメチルヒド
ラジン12.7gを滴下し、同温度で５時間撹拌し、減圧下
濃縮した。次いでトルエンで抽出後、水洗した。トルエ
ン層を濃縮し、ヘキサンを加え10℃まで冷却し、副生析
出結晶を別した。液を濃縮後、蒸留しbp113〜115℃
/0.7mmHgの表−１記載の化合物（No.3）24.5gを得た。
得られた化合物のNMRおよびIRスペクトラムを以下に示
す。Example 1 Preparation of ethyl 2,6-dimethylcyclopenta [1,2-C] -3-pyrazolecarboxylate In a solution of 46.1 g of ethyl 2-ketocyclopentylglyoxalate in 100 ml of ethanol, methylhydrazine was added at 20 to 25 ° C. 12.7 g was added dropwise, the mixture was stirred at the same temperature for 5 hours, and concentrated under reduced pressure. Next, the mixture was extracted with toluene and washed with water. The toluene layer was concentrated, hexane was added and the mixture was cooled to 10 ° C., and the by-product precipitated crystals were separated. After concentrating the liquid, distill it by bp 113 to 115 ° C.
24.5 g of the compound (No. 3) described in Table 1 was obtained at a pressure of 0.7 mmHg.
The NMR and IR spectra of the obtained compound are shown below.
1H−NMR（CDCl3）δppm;1.29（ｄ）3H,1.37（ｔ）3H,
1.8〜3.3（ｍ）5H,4.15（ｓ）3H,4.33（ｑ）2H IR（NaCl）;1720cm-1 実施例２ 2,6−ジメチルシクロペンタ〔1,2−Ｃ〕−３−ピラゾー
ルカルボン酸の製造 2,6−ジメチルシクロペンタ〔1,2−Ｃ〕−３−ピラゾ
ールカルボン酸エチルエステル19.6gと水酸化ナトリウ
ム8.0gの40ml水溶液を１時間加熱還流した。室温に冷却
後、塩酸で酸性にし析出物を取した。減圧下50℃で乾
燥し表−１記載の化合物（No.2）15.1g、mp171〜173℃
を得た。得られた化合物のNMRおよびIRスペクトラムを
以下に示す。 1 H-NMR (CDCl 3 ) δ ppm; 1.29 (d) 3 H, 1.37 (t) 3 H,
1.8-3.3 (m) 5H, 4.15 (s) 3 H, 4.33 (q) 2 H IR (NaCl); 1720 cm -1 Example 2 2,6-dimethylcyclopenta [1,2-C] -3-pyrazolecarboxylic acid Preparation of 19.6 g of ethyl 2,6-dimethylcyclopenta [1,2-C] -3-pyrazolecarboxylate and 8.0 g of sodium hydroxide in a 40 ml aqueous solution were heated under reflux for 1 hour. After cooling to room temperature, the mixture was acidified with hydrochloric acid and the precipitate was collected. Dried at 50 ° C under reduced pressure, 15.1 g of the compound (No. 2) described in Table 1, mp 171-173 ° C
I got The NMR and IR spectra of the obtained compound are shown below.
1H−NMR（CDCl3）δppm;1.25（ｄ）3H,1.95（ｍ）1H,
2.4〜3.0（ｍ）3H,3.15（ｍ）1H,4.15（ｓ）3H IR（KBr）;1710cm-1 実施例３ ２−メチルシクロペンタ〔1,2−Ｃ〕−３−ピラゾール
カルボン酸エチルエステルの製造 ２−ケトシクロペンチルグリオキザル酸エチルエステ
ル18.4gのエタノール100ml溶液中にヒドラジンヒドラー
ト5.0gを滴下し１時間撹拌後、析出物を別した。液
を濃縮後、残渣をトルエンで抽出した水洗した。減圧下
トルエンを留去し油状物を得た。次に本油状物中にジメ
チル硫酸25.2gを40℃で滴下した。40〜50℃で３時間撹
拌後、室温に冷却し、氷水中に注ぎ、炭酸ナトリウムを
加えpHを８〜９にした。油状物を酢酸エチルで抽出し、
水洗後濃縮した。残渣をシリカゲムカラムクロマトグラ
フィーで精製し、表−１記載の化合物（No.1）90g、mp4
8〜49℃を得た。得られた化合物のNMRおよびIRスペクト
ラムを以下に示す。 1 H-NMR (CDCl 3 ) δ ppm; 1.25 (d) 3 H, 1.95 (m) 1 H,
2.4-3.0 (m) 3 H, 3.15 (m) 1 H, 4.15 (s) 3 H IR (KBr); 1710 cm -1 Example 3 2-methylcyclopenta [1,2-C] -3-pyrazolecarboxylic acid ethyl ester Preparation of 5.0 g of hydrazine hydrate was dropped into a solution of 18.4 g of 2-ketocyclopentylglyoxalic acid ethyl ester in 100 ml of ethanol, and the mixture was stirred for 1 hour. After concentration, the residue was washed with water extracted with toluene. The toluene was distilled off under reduced pressure to obtain an oil. Next, 25.2 g of dimethyl sulfate was added dropwise to the oil at 40 ° C. After stirring at 40 to 50 ° C. for 3 hours, the mixture was cooled to room temperature, poured into ice water, and adjusted to pH 8 to 9 by adding sodium carbonate. Extract the oil with ethyl acetate,
After washing with water, the mixture was concentrated. The residue was purified by silica gem column chromatography, and 90 g of the compound (No.
8-49 ° C was obtained. The NMR and IR spectra of the obtained compound are shown below.
1H−NMR（CDCl3）δppm;1.35（ｔ）3H,2.3〜2.95（m,
6H）,4.1（ｓ）3H,4.35（ｑ）2H IR（KBr）;1710cm-1 実施例４ 実施例１〜３と同様にして表−１記載の化合物を得
た。 1 H-NMR (CDCl 3 ) δ ppm; 1.35 (t) 3 H, 2.3 to 2.95 (m,
6H), 4.1 (s) 3 H, 4.35 (q) 2 H IR (KBr); 1710 cm -1 Example 4 The compounds described in Table 1 were obtained in the same manner as in Examples 1 to 3.
なお、表−１に記載した一部の化合物につき、そのNM
RおよびIRスペクトラムを以下に示す。 In addition, for some compounds described in Table 1, their NM
The R and IR spectra are shown below.
No.4 1H−NMR（CDCl3）δppm;1.1〜1.6（ｍ）9H,2.1〜2.3
（ｍ）2H,2.6〜3.4（ｍ）2H,4.1（ｓ）3H,4.35（ｑ）2H IR（NaCl）;1710cm-1 No.8 1H−NMR（CDCl3）δppm;1.2〜1.5（ｍ）6H,2.4（ｍ）
2H,2.7（ｍ）4H,4.25（ｑ）2H,4.45（ｑ）2H IR（NaCl）;1720cm-1 No.9 1H−NMR（CDCl3）δppm;1.35（ｍ）9H,2.15〜2.90
（ｍ）6H,4.3（ｑ）2H,5.5（ｍ）1H IR（NaCl）;1706cm-1 No.10 1H−NMR（CDCl3）δppm;1.5（d,6H）,2.3〜2.95
（ｍ）6H,5.45（ｍ）1H,8.05（bs）1H IR（KBr）;1705cm-1 No.11 1H−NMR（CDCl3）δppm;0.9（ｔ）3H,1.4（ｍ）5H,1.
5〜1.9（ｍ）2H,2.2〜2.9（ｍ）6H,4.15〜4.6（ｍ）4H IR（NaCl）;1716cm-1 No.12 1H−NMR（CDCl3）δppm;0.95（ｔ）3H,1.1〜2.0
（ｍ）4H,2.3〜3.0（ｍ）6H,4.5（ｔ）2H,7.8（bs）1H IR（KBr）;1719cm-1 No.13 1H−NMR（CDCl3）δppm;1.4（ｔ）3H,1.6（ｓ）9H,3.
05〜2.4（ｍ）6H,4.45（ｑ）2H IR（NaCl）;1725cm-1 No.15 1H−NMR（CDCl3）δppm;1.0（ｔ）3H,1.25（ｄ）3H,
1.5〜2.1（ｍ）3H,2.4〜2.9（ｍ）3H,3.15（ｍ）1H,4.1
5（ｓ）3H,4.2（ｔ）2H IR（NaCl）;1720cm-1 No.16 1H−NMR（CDCl3）δppm;1.2〜1.4（ｍ）9H,1.7〜2.3
（ｍ）1H,2.3〜2.9（ｍ）3H,3.15（ｍ）1H,4.1（ｓ）3
H,5.15（ｍ）1H IR（NaCl）;1710cm-1 No.17 1H−NMR（CDCl3）δppm;0.95（ｔ）3H,1.2（ｄ）3H,
1.1〜2.1（ｍ）5H,2.65（ｍ）3H,3.05（ｍ）1H,4.05
（ｓ）3H,4.2（ｔ）2H IR（NaCl）;1720cm-1 No.18 1H−NMR（CDCl3）δppm;0.95（ｔ）3H,1.15〜1.4
（ｍ）6H,1.4〜2.2（ｍ）3H,2.2〜2.85（ｍ）3H,3.05
（ｍ）1H,4.05（ｓ）3H,4.95（m,1H） IR（NaCl）;1715cm-1 No.19 1H−NMR（CDCl3）δppm;1.2（ｄ）3H,1.5（ｓ）9H,1.
9（ｍ）1H,2.3〜2.75（ｍ）3H,3.0（ｍ）1H,4.0（ｓ）3
H IR（NaCl）;1710cm-1 〔発明の効果〕 本発明のシクロペンタ〔1,2−Ｃ〕−３−ピラゾール
カルボン酸誘導体は、ピラゾール系殺虫、殺ダニ剤およ
び殺菌剤の中間体として有用であり、その工業的価値は
高い。No. 41 1 H-NMR (CDCl 3 ) δ ppm; 1.1 to 1.6 (m) 9H, 2.1 to 2.3
(M) 2H, 2.6~3.4 (m ) 2H, 4.1 (s) 3H, 4.35 (q) 2H IR (NaCl); 1710cm -1 No.8 1 H-NMR (CDCl 3) δppm; 1.2~1.5 (m ) 6H, 2.4 (m)
2H, 2.7 (m) 4H, 4.25 (q) 2H, 4.45 (q) 2H IR (NaCl); 1720cm -1 No.9 1 H-NMR (CDCl 3) δppm; 1.35 (m) 9H, 2.15~2.90
(M) 6H, 4.3 (q) 2 H, 5.5 (m) 1H IR (NaCl); 1706 cm -1 No. 10 1 H-NMR (CDCl 3 ) δ ppm; 1.5 (d, 6H), 2.3 to 2.95
(M) 6H, 5.45 (m) 1H, 8.05 (bs) 1H IR (KBr); 1705 cm -1 No. 11 1 H-NMR (CDCl 3 ) δ ppm; 0.9 (t) 3 H, 1.4 (m) 5 H, 1 .
5~1.9 (m) 2H, 2.2~2.9 ( m) 6H, 4.15~4.6 (m) 4H IR (NaCl); 1716cm -1 No.12 1 H-NMR (CDCl 3) δppm; 0.95 (t) 3H, 1.1-2.0
(M) 4H, 2.3~3.0 (m ) 6H, 4.5 (t) 2H, 7.8 (bs) 1H IR (KBr); 1719cm -1 No.13 1 H-NMR (CDCl 3) δppm; 1.4 (t) 3H , 1.6 (s) 9H, 3.
05~2.4 (m) 6H, 4.45 ( q) 2H IR (NaCl); 1725cm -1 No.15 1 H-NMR (CDCl 3) δppm; 1.0 (t) 3H, 1.25 (d) 3H,
1.5 ~ 2.1 (m) 3H, 2.4 ~ 2.9 (m) 3H, 3.15 (m) 1H, 4.1
5 (s) 3H, 4.2 ( t) 2H IR (NaCl); 1720cm -1 No.16 1 H-NMR (CDCl 3) δppm; 1.2~1.4 (m) 9H, 1.7~2.3
(M) 1H, 2.3 to 2.9 (m) 3H, 3.15 (m) 1H, 4.1 (s) 3
H, 5.15 (m) 1 H IR (NaCl); 1710 cm -1 No. 17 1 H-NMR (CDCl 3 ) δ ppm; 0.95 (t) 3 H, 1.2 (d) 3 H,
1.1 ~ 2.1 (m) 5H, 2.65 (m) 3H, 3.05 (m) 1H, 4.05
(S) 3 H, 4.2 (t) 2 H IR (NaCl); 1720 cm -1 No. 18 1 H-NMR (CDCl 3 ) δ ppm; 0.95 (t) 3 H, 1.15 to 1.4
(M) 6H, 1.4-2.2 (m) 3H, 2.2-2.85 (m) 3H, 3.05
(M) 1 H, 4.05 (s) 3 H, 4.95 (m, 1 H) IR (NaCl); 1715 cm -1 No. 19 1 H-NMR (CDCl 3 ) δ ppm; 1.2 (d) 3 H, 1.5 (s) 9 H, 1.
9 (m) 1H, 2.3-2.75 (m) 3H, 3.0 (m) 1H, 4.0 (s) 3
HIR (NaCl); 1710 cm -1 [Effect of the Invention] The cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivative of the present invention is useful as an intermediate for pyrazole insecticides, acaricides and fungicides. Yes, its industrial value is high.
Claims (1)
〔1,2−Ｃ〕−３−ピラゾールカルボン酸誘導体。 （上記式中、R1はC1〜C4のアルキル基を示し、R2は水素
原子またはC1〜C3のアルキル基を示し、R3は水素原子ま
たはメチル基を示し、R4は水素原子またはC1〜C4のアル
キル基を示す。ただし、R1がメチル基またはエチル基で
あり、且つR2とR3が共に水素原子である場合、R4はC2〜
C4のアルキル基を示す。）1. A cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivative represented by the following general formula (I). (In the above formula, R 1 represents a C 1 -C 4 alkyl group, R 2 represents a hydrogen atom or a C 1 -C 3 alkyl group, R 3 represents a hydrogen atom or a methyl group, and R 4 represents A hydrogen atom or a C 1 to C 4 alkyl group, provided that when R 1 is a methyl group or an ethyl group, and R 2 and R 3 are both hydrogen atoms, R 4 is a C 2 to C 4
C 4 represents an alkyl group. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1049330A JP2743441B2 (en) | 1989-03-01 | 1989-03-01 | Cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1049330A JP2743441B2 (en) | 1989-03-01 | 1989-03-01 | Cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02229171A JPH02229171A (en) | 1990-09-11 |
| JP2743441B2 true JP2743441B2 (en) | 1998-04-22 |
Family
ID=12827979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1049330A Expired - Fee Related JP2743441B2 (en) | 1989-03-01 | 1989-03-01 | Cyclopenta [1,2-C] -3-pyrazolecarboxylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2743441B2 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861777A (en) * | 1987-09-11 | 1989-08-29 | Mitsubishi Kasei Corporation | Pyrazole derivative and insecticidal and miticidal composition containing the derivative as active ingredient |
-
1989
- 1989-03-01 JP JP1049330A patent/JP2743441B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02229171A (en) | 1990-09-11 |
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