JPS6210987B2 - - Google Patents
Info
- Publication number
- JPS6210987B2 JPS6210987B2 JP11816179A JP11816179A JPS6210987B2 JP S6210987 B2 JPS6210987 B2 JP S6210987B2 JP 11816179 A JP11816179 A JP 11816179A JP 11816179 A JP11816179 A JP 11816179A JP S6210987 B2 JPS6210987 B2 JP S6210987B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound
- formula
- trichloropropyl
- present
- 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 3
- 150000001875 compounds Chemical class 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 bromopropyl Chemical group 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002994 raw material 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UPTGDTIXYFULAB-UHFFFAOYSA-N 1-(1,3,3,3-tetrachloropropoxy)butane Chemical compound CCCCOC(Cl)CC(Cl)(Cl)Cl UPTGDTIXYFULAB-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Indole 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〔１〕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 [1].
〔式中R1は低級アルキル基、Ｘはハロゲン原
子およびＡはＣ＝Ｏ基またはSO2基を夫々示
す。〕
上記一般式〔１〕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 represents a lower alkyl group, X represents a halogen atom, and A represents a C═O group or an SO 2 group, respectively. ] The compound of the present invention represented by the above general formula [1] has antibacterial activity, particularly shows excellent bactericidal activity against various plant pathogenic fungi, and has almost no risk of phytotoxicity, and is useful in agriculture and horticulture. It is useful as a fungicide.
上記一般式〔１〕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、弗素、沃素および
臭素原子が包含される。 In the above general formula [1], examples of the lower alkyl group include methyl, ethyl, propyl, isopropyl, butyl, and tert-butyl groups.
Furthermore, halogen atoms include chlorine, fluorine, iodine and bromine 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.
ΓＮ―（１―エトキシ―３，３，３―トリクロロ
プロピル）フタルイミド
ΓＮ―（１―ｎ―ブトキシ―３，３，３―トリク
ロロプロピル）フタルイミド
ΓＮ―（１―イソブトキシ―３，３，３―トリブ
ロモプロピル）フタルイミド
ΓＮ―（１―メトキシ―３，３，３―トリクロロ
プロピル）―Ｏ―スルホベンゾイミド
ΓＮ―（１―ｎ―ブトキシ―３，３，３―トリフ
ルオロプロピル）―Ｏ―スルホベンゾイミド
ΓＮ―（１―イソプロポキシ―３，３，３―トリ
クロロプロピル）―Ｏ―スルホベンゾイミド
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
に一般式
〔式中Ａは上記に同じ〕
で表わされる公知のベンゾヘテロ環化合物を反応
させることにより製造される。ΓN-(1-ethoxy-3,3,3-trichloropropyl)phthalimide ΓN-(1-n-butoxy-3,3,3-trichloropropyl)phthalimide ΓN-(1-isobutoxy-3,3,3-trichloropropyl) bromopropyl) phthalimide ΓN-(1-methoxy-3,3,3-trichloropropyl)-O-sulfobenzimide ΓN-(1-n-butoxy-3,3,3-trifluoropropyl)-O-sulfobenzo Imide ΓN-(1-isopropoxy-3,3,3-trichloropropyl)-O-sulfobenzimide The compound of the present invention can be prepared, for example, by the following general formula: [In the formula, R 1 and X are the same as above] 3-alkoxy-1,1,1,3-
Using tetrahalopropane as a raw material, the general formula [In the formula, A is the same as above] It is produced by reacting a known benzoheterocyclic compound represented by the following formula.
上記一般式〔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 above general formula [2] 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, ECStump, JOC
29 , 1198 (1964), U.S. Patent No. 2560219 and C.
A., 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〕で表わされる化合物と一般式
〔３〕で表わされる化合物との反応は、より具体
的には次の如くして行なわれる。即ち例えばアセ
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等のエーテル類、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、エタノール等のアルコール類、
ジメチルスルホキシド、ジメチルホルムアミド等
の適当な不活性溶媒中で、例えば炭酸カリウム、
炭酸ナトリウム、ナトリウムメチラート、ナトリ
ウムエチラート、水酸化カリウム、水酸化ナトリ
ウム、水素化ナトリウム、トリエチルアミン、ナ
トリウムアミン、ジメチルアニリン等、好ましく
は水酸化カリウム、水酸化ナトリウム、ナトリウ
ムエチラート等の塩基性化合物を脱酸剤として利
用するか又は用いることなく、一般式〔２〕の化
合物と一般式〔３〕の化合物とを０〜100℃好ま
しくは０〜50℃下に１〜５時間通常１〜２時間程
度反応させることにより行なわれる。一般式
〔２〕の化合物に対する一般式〔３〕の化合物の
使用量は通常等モル以上好ましくは等モル〜1.5
倍モル程度とすればよい。また脱酸剤は通常一般
式〔２〕の化合物に対して等モル以上好ましくは
等モル〜1.5倍モル程度用いるのが適当である。 More specifically, the reaction between the compound represented by the above general formula [2] and the compound represented by the general formula [3] is carried out as follows. That is, for example, ketones such as acetone and methyl ethyl ketone, ethers such as diglyme and tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene and xylene, alcohols such as methanol and ethanol,
For example, potassium carbonate,
Basic compounds such as sodium carbonate, sodium methylate, sodium ethylate, potassium hydroxide, sodium hydroxide, sodium hydride, triethylamine, sodium amine, dimethylaniline, etc., preferably potassium hydroxide, sodium hydroxide, sodium ethylate, etc. The compound of general formula [2] and the compound of general formula [3] are heated at 0 to 100°C, preferably 0 to 50°C, for 1 to 5 hours, usually for 1 to 2 hours, with or without using as a deoxidizing agent. This is carried out by allowing the reaction to take place for about an hour. The amount of the compound of general formula [3] to be used with respect to the compound of general formula [2] is usually equal to or more than equimolar, preferably equimolar to 1.5
The amount may be about double the molar amount. Further, the deoxidizing agent is usually used in an amount equal to or more than the amount of the compound represented by the general formula [2], preferably about 1 to 1.5 times the amount of the compound represented by the general formula [2].
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 50g 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. As a fraction of 74-75℃ under 2mmHg, 3
-118 g of n-butyloxy-1,1,1,3-tetrachloropropane is obtained.
実施例 １
フタルイミドカリウム塩1.71ｇを水５mlに溶解
し、アセトン50ml中に激しい撹拌下に添加する。
３―ｎ―ブチルオキシ―１，１，１，３―テトラ
クロロプロパン2.56ｇを加え、室温下に２時間撹
拌する。反応終了後不溶物を別し減圧乾固す
る。Example 1 1.71 g of phthalimide potassium salt are dissolved in 5 ml of water and added to 50 ml of acetone under vigorous stirring.
Add 2.56 g of 3-n-butyloxy-1,1,1,3-tetrachloropropane and stir at room temperature for 2 hours. After the reaction is complete, insoluble materials are separated and dried under reduced pressure.
残渣を石油エーテル100ml中に取り出し加熱溶
解し不溶物を別し、液を冷却して、無色粉末
結晶のＮ―（１―ｎ―ブチルオキシ―３，３，３
―トリクロロプロピル）フタルイミド0.8ｇを得
る。 The residue was taken out in 100 ml of petroleum ether, heated and dissolved, the insoluble matter was separated, the liquid was cooled, and colorless powder crystals of N-(1-n-butyloxy-3,3,3
- 0.8 g of trichloropropyl) phthalimide is obtained.
融点 97〜97.5℃
核磁気共鳴スペクトル分析
δ＝7.7〜7.2ppm（ｍ，4H）
6.2ppm（ｔ，1H）
3.7〜3.2ppm（ｍ，4H）
1.8〜0.7ppm（ｍ，7H）
実施例 ２
上記実施例１と同様にして無色粉末結晶のＮ―
（１―ｎ―ブトキシ―３，３，３―トリクロロプ
ロピル）―Ｏ―スルホベンゾイミドを得る。 Melting point 97-97.5°C Nuclear magnetic resonance spectroscopy δ = 7.7-7.2ppm (m, 4H) 6.2ppm (t, 1H) 3.7-3.2ppm (m, 4H) 1.8-0.7ppm (m, 7H) Example 2 Above Colorless powder crystal N-
(1-n-butoxy-3,3,3-trichloropropyl)-O-sulfobenzimide is obtained.
融点 80〜81℃ Melting point 80~81℃
Claims (1)
子およびＡはＣ＝Ｏ基またはSO2基を夫々示
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 represents a lower alkyl group, X represents a halogen atom, and A represents a C═O group or an SO 2 group, respectively. ] A trihalopropane derivative characterized by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11816179A JPS5643265A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11816179A JPS5643265A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5643265A JPS5643265A (en) | 1981-04-21 |
| JPS6210987B2 true JPS6210987B2 (en) | 1987-03-10 |
Family
ID=14729604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11816179A Granted JPS5643265A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5643265A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63196389U (en) * | 1987-05-29 | 1988-12-16 |
-
1979
- 1979-09-13 JP JP11816179A patent/JPS5643265A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63196389U (en) * | 1987-05-29 | 1988-12-16 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5643265A (en) | 1981-04-21 |
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