JPS6237626B2 - - Google Patents
Info
- Publication number
- JPS6237626B2 JPS6237626B2 JP11816279A JP11816279A JPS6237626B2 JP S6237626 B2 JPS6237626 B2 JP S6237626B2 JP 11816279 A JP11816279 A JP 11816279A JP 11816279 A JP11816279 A JP 11816279A JP S6237626 B2 JPS6237626 B2 JP S6237626B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- trichloropropyl
- carbon tetrachloride
- examples
- 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.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- -1 1-(1-n-butoxy-3,3,3-trichloropropyl)pyridinium chloride Chemical compound 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 本発明はトリハロプロパン誘導体に関する。[Detailed description of the invention] The present invention relates to trihalopropane derivatives.
本発明のトリハロプロパン誘導体は新規な化合
物であり、下記一般式〔〕で表わされる。 The trihalopropane derivative of the present invention is a novel compound and is represented by the following general formula [].
〔式中R1は低級アルキル基およびＸはハロゲ
ン原子を示す〕
上記一般式〔〕で表わされる本発明化合物
は、抗菌活性を有し、殊に各種の植物病原性真菌
類に対して優れた殺菌活性を示し、また薬害のお
それもほとんどなく、農園芸用殺菌剤として有用
である。 [In the formula, R 1 is a lower alkyl group and It exhibits bactericidal activity and has little risk of phytotoxicity, making it useful as a fungicide for agriculture and horticulture.
上記一般式〔〕において低級アルキル基とし
ては例えばメチル、エチル、プロピル、イソプロ
ピル、ブチル、tert−ブチル基等を例示できる。
またハロゲン原子には、塩素、沃素、臭素および
弗素原子が包含される。 In the above general formula [], examples of lower alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, and tert-butyl groups.
Furthermore, halogen atoms include chlorine, iodine, bromine and fluorine atoms.
以下本発明化合物の代表例を示す。 Representative examples of the compounds of the present invention are shown below.
Γ １−（１−ｎ−ブトキシ−３，３，３−トリ
クロロプロピル）ピリジニウムクロライド
Γ １−（１−エトキシ−３，３，３−トリクロ
ロプロピル）ピリジニウムブロマイド
Γ １−（１−イソプロポキシ−３，３，３−ト
リフルオロプロピル）ピリジニウムクロライド
Γ １−（１−メトキシ−３，３，３−トリクロ
ロプロピル）ピリジニウムクロライド
Γ １−（１−イソブトキシ−３，３，３−トリ
クロロプロピル）ピリジニウムクロライド
本発明化合物は、例えば下記一般式
〔式中R1及びＸは上記に同じ〕
で表わされる３−アルコキシ−１，１，１，３−
テトラハロプロパンを原料として、これに適当な
不活性溶媒中、脱酸剤の存在下もしくは不存在下
にピリジン〔３〕を反応させることにより製造さ
れる。Γ 1-(1-n-butoxy-3,3,3-trichloropropyl)pyridinium chloride Γ 1-(1-ethoxy-3,3,3-trichloropropyl)pyridinium bromide Γ 1-(1-isopropoxy-3 ,3,3-trifluoropropyl)pyridinium chloride Γ 1-(1-methoxy-3,3,3-trichloropropyl)pyridinium chloride Γ 1-(1-isobutoxy-3,3,3-trichloropropyl)pyridinium chloride Book The invention compound has, for example, the following general formula: [In the formula, R 1 and X are the same as above] 3-alkoxy-1,1,1,3-
It is produced by using tetrahalopropane as a raw material and reacting it with pyridine [3] in an appropriate inert solvent in the presence or absence of a deoxidizing agent.
上記において一般式〔２〕で表わされる原料化
合物は公知化合物であり、例えば次式に示すよう
にして合成される〔M.Laevas，Ann.Chem.
〔12〕，７，697（1952）、P.Tarrant，E.C.
Stump，J.O.C.29，1198（1964）、米国特許第
2560219号及びC.A.，46，1023（1952）〕。 The raw material compound represented by the general formula [2] above is a known compound, and is synthesized, for example, as shown in the following formula [M. Laevas, Ann. Chem.
[12], 7 , 697 (1952), P. Tarrant, EC
Stump, JOC 29 , 1198 (1964), U.S. Pat.
No. 2560219 and CA, 46 , 1023 (1952)].
〔式中R1及びＸは上記に同じ〕
即ち上記一般式〔４〕で表わされる化合物と一
般式〔５〕で表わされる化合物とを光射照するか
又はラジカル開始剤例えばベンゾイルパーオキサ
イド、アゾビスイソブチロニトリル等の存在下に
50〜100℃の温度下に加熱して反応させることに
より容易に収得できる。 [In the formula, R 1 and In the presence of bisisobutyronitrile etc.
It can be easily obtained by heating and reacting at a temperature of 50 to 100°C.
上記一般式〔２〕で表わされる原料化合物とピ
リジンとの反応は無溶媒または適当な溶媒中で実
施される。溶媒としては例えばアセトン、メチル
エチルケトン等のケトン類、ジグライム、テトラ
ヒドロフラン、ジエチルエーテル等のエーテル
類、四塩化炭素、クロロホルム、塩化メチレン等
のハロゲン化炭化水素類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類等を使用できる。
反応は通常室温〜100℃好ましくは室温〜50℃程
度の温度下に１〜10時間通常１〜２時間程度で行
なわれる。一般式〔２〕の化合物に対するピリジ
ンの使用量は、通常等モル以上好ましくは等モル
〜1.1倍モル程度とするのが適当である。 The reaction between the raw material compound represented by the above general formula [2] and pyridine is carried out without a solvent or in a suitable solvent. Examples of solvents include ketones such as acetone and methyl ethyl ketone, ethers such as diglyme, tetrahydrofuran, and diethyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, and methylene chloride, benzene, toluene,
Aromatic hydrocarbons such as xylene can be used.
The reaction is usually carried out at a temperature of about room temperature to 100°C, preferably about room temperature to 50°C, for about 1 to 10 hours, usually about 1 to 2 hours. The amount of pyridine to be used relative to the compound of general formula [2] is usually about 1 mole or more, preferably about 1 mole to 1.1 times the mole.
かくして一般式〔１〕で表わされる本発明のト
リハロプロパン誘導体を収得する。得られる化合
物は、反応終了後常法に従いカラムクロマトグラ
フイーや溶媒抽出法、再結晶法等により単離精製
できる。 In this way, the trihalopropane derivative of the present invention represented by general formula [1] is obtained. After completion of the reaction, the resulting compound can be isolated and purified by column chromatography, solvent extraction, recrystallization, etc. in accordance with conventional methods.
以下本発明化合物の製造に用いる原料化合物の
製造例を参考例として挙げ、次いで本発明化合物
の製造例を実施例として挙げる。 Hereinafter, production examples of raw material compounds used for production of the compounds of the present invention will be listed as reference examples, and then production examples of the compounds of the present invention will be listed as examples.
参考例 １
四塩化炭素150mlにアゾビスイソブチロニトリ
ル300mgを加え還流する。滴下斗よりｎ−ブチ
ルビニルエーテル50ｇを少量づつ滴下し、更に１
時間還流後四塩化炭素を減圧下に除去し、減圧蒸
留する。２mmHg下に74〜75℃の留分として、３
−ｎ−ブチルオキシ−１，１，１，３−テトラク
ロロプロパン118ｇを得る。Reference Example 1 Add 300 mg of azobisisobutyronitrile to 150 ml of carbon tetrachloride and reflux. Add 50 g of n-butyl vinyl ether little by little from the dropping funnel, and add 1
After refluxing for a period of time, carbon tetrachloride is removed under reduced pressure and distilled under reduced pressure. 3 as a fraction of 74-75℃ under 2mmHg
118 g of -n-butyloxy-1,1,1,3-tetrachloropropane are obtained.
実施例 １
ピリジン0.79ｇ及び３−イソブチルオキシ−
１，１，１，３−テトラクロロプロパン2.54ｇを
室温下に混合し、２時間放置する。その後四塩化
炭素20mlを加え撹拌し、四塩化炭素可溶部を分別
除去する。四塩化炭素不溶部を減圧濃縮して、淡
褐色油状の１−（１−イソブチルオキシ−３，
３，３−トリクロロプロピル）ピリジニウムクロ
ライド2.3ｇを得る。Example 1 0.79 g of pyridine and 3-isobutyloxy-
2.54 g of 1,1,1,3-tetrachloropropane is mixed at room temperature and left for 2 hours. Thereafter, 20 ml of carbon tetrachloride is added and stirred, and the carbon tetrachloride soluble portion is separated and removed. The carbon tetrachloride insoluble portion was concentrated under reduced pressure to obtain a light brown oily 1-(1-isobutyloxy-3,
2.3 g of 3,3-trichloropropyl)pyridinium chloride are obtained.
屈折率ｎ２５ Ｄ＝1.5325
核磁気共鳴スペクトル分析
δ＝9.70ppm（ｄ，1H）
8.72ppm（ｄ，1H）
8.30ppm（ｔ，2H）
7.80ppm（b.s，1H）
7.00ppm（ｔ，2H）
3.80ppm（ｍ，2H）
3.20ppm（ｍ，2H）
2.00ppm（sextet，1H）
0.90ppm（ｄ，6H）
実施例 ２
上記実施例１と同様にして、１−（１−ｎ−ブ
トキシ−３，３，３−トリクロロプロピル）ピリ
ジニウムクロライドを得る。 Refractive index n 25 D = 1.5325 Nuclear magnetic resonance spectroscopy δ = 9.70ppm (d, 1H) 8.72ppm (d, 1H) 8.30ppm (t, 2H) 7.80ppm (bs, 1H) 7.00ppm (t, 2H) 3.80 ppm (m, 2H) 3.20ppm (m, 2H) 2.00ppm (sextet, 1H) 0.90ppm (d, 6H) Example 2 1-(1-n-butoxy-3, 3,3-trichloropropyl)pyridinium chloride is obtained.
屈折率ｎ２５ Ｄ＝1.5502 Refractive index n 25 D = 1.5502
Claims (1)
ン原子を示す〕 で表わされることを特徴とするトリハロプロパン
誘導体。[Claims] 1. General formula [In the formula, R 1 is a lower alkyl group and X represents a halogen atom] A trihalopropane derivative represented by the following formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11816279A JPS5643267A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11816279A JPS5643267A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5643267A JPS5643267A (en) | 1981-04-21 |
| JPS6237626B2 true JPS6237626B2 (en) | 1987-08-13 |
Family
ID=14729630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11816279A Granted JPS5643267A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5643267A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0718035U (en) * | 1992-10-20 | 1995-03-31 | 株式会社猫田電機 | Slip clutch |
-
1979
- 1979-09-13 JP JP11816279A patent/JPS5643267A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0718035U (en) * | 1992-10-20 | 1995-03-31 | 株式会社猫田電機 | Slip clutch |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5643267A (en) | 1981-04-21 |
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